Multiple Cities, Zip Codes, Addresses, Streets, Neighborhoods, MLS IDs
(separate each with the word OR)
Ex.Miami OR Coral Springs OR Boca Raton 33319 OR 33321 OR 33467
VISCONTI WEST CONDO - O6422624 - 1460 LAKE SHADOW CIR #7207, MAITLAND, FL 32751 1 Day on yellowkey
$245,000 | Condo 4 bedrooms, 2.0 bathroom
A rare 4 BR condo with A rated High School could be your next home. Visconti is a high end luxury community featuring a huge lakeside pool with beach entry, fitness center that rivals many commercial gyms, tennis courts, walking paths, and a fantastic clubhouse. The 2nd floor condo has an extremely functional layout that separates the master BR from the other 3 bedrooms. The kitchen is stunning with updated cabinets, solid surface counters and a gorgeous back splash. The common areas feature wood laminate floors with carpet in the bedrooms. Conveniently located in Maitland, this homes is just minutes away from restaurants, shops, I4, 414, and the Maitland business center. A fantastic choice for your main home, a 2nd home or an addition to a rental portfolio.
This listing is courtesy of: INFINITY REAL ESTATE GROUP
VISCONTI EAST - O6422110 - 1952 LEGACY COVE DR #1952, MAITLAND, FL 32751 6 Days on yellowkey
$199,000 | Townhouse 2 bedrooms, 2.0 bathroom, 1 car garage
Experience resort-style living in the heart of Maitland at the highly desirable gated community of Visconti. This beautifully maintained three-story townhome offers 1,280 square feet of thoughtfully designed living space plus an oversized attached garage, providing the perfect combination of comfort, functionality, and low-maintenance living. The open-concept main living level features luxury vinyl flooring, soaring ceilings, abundant natural light, and a spacious kitchen with stainless steel appliances, updated countertops, tile backsplash, breakfast bar seating, and generous cabinet space. The spacious primary suite offers a large walk-in closet and private bath, while the additional bedrooms provide flexibility for guests, a home office, or growing families. A full-size interior laundry room, ample storage, and neutral finishes make this home truly move-in ready. Visconti residents enjoy an impressive collection of amenities including a gated entrance, resort-style swimming pool, a state-of-the-art fitness center, playground, scenic walking paths, car wash station, and beautifully landscaped grounds shaded by mature oak trees. Conveniently located just minutes from I-4, Winter Park, Downtown Orlando, AdventHealth, RDV Sportsplex, shopping, dining, and entertainment, this home offers the perfect blend of convenience, lifestyle, and value.
This listing is courtesy of: OLDE TOWN BROKERS INC
DIXIE TERRACE - O6420390 - 1783 SUNNYSIDE DR, MAITLAND, FL 32751 8 Days on yellowkey
$849,900 | Single Family Home 3 bedrooms, 2.5 bathroom, 1 car garage
Perfectly positioned between Maitland and Winter Park, this beautifully maintained 3-bedroom, 2.5-bath pool home offers an exceptional combination of charm, character, and an unbeatable location just minutes from the shops and restaurants of Park Avenue. Warm hardwood floors flow throughout the home, while the impressive two-story family room showcases soaring ceilings and a wood-burning fireplace that creates a welcoming gathering space. Separate living and dining rooms provide flexibility for both everyday living and effortless entertaining. The kitchen is thoughtfully designed with newer stainless-steel appliances and opens to the family room. French doors invite you outside to a private backyard retreat, while the adjacent sunroom is the perfect place to enjoy morning coffee with peaceful views of the pool and lush landscaping. Upstairs, you'll find three spacious bedrooms and two beautifully renovated baths. The primary suite is filled with natural light from a charming bay window and features a spa-inspired bath with marble floors, quartz countertops, dual vanities, and timeless subway tile. Step outside to your own backyard oasis. The covered lanai, complete with a summer kitchen, overlooks a newer saltwater pool and an expansive brick patio, creating the ideal setting for year-round outdoor living, entertaining, or simply unwinding in a private, tranquil setting. Adding to its appeal, the home is located just one house from the Winter Park city limits and is zoned for highly acclaimed Dommerich Elementary, Maitland Middle, and Winter Park High School. Enjoy the convenience of nearby Lake Lily, Enzian Theater, Maitland City Centre, and the boutiques, dining, and vibrant lifestyle of Winter Park's famed Park Avenue. This home offers the rare opportunity to enjoy a peaceful neighborhood setting with the very best of Maitland and Winter Park just moments away.
This listing is courtesy of: FANNIE HILLMAN & ASSOCIATES
MAITLAND CLUB REP - O6420911 - 900 BRIGHTWATER CIR, MAITLAND, FL 32751 9 Days on yellowkey
$1,150,000 | Single Family Home 5 bedrooms, 3.5 bathroom, 2 car garage
Welcome to the Premier community of Maitland Club. The paver walkway and covered front patio lead you into the spacious foyer, featuring the elegant formal living and dining rooms with hardwood floors, crown molding and plantation shutters. The Kitchen features Granite countertops, 42” cabinets and lots of natural light. The warm and inviting family room area offers a woodburning fireplace with built-in shelving and an open floor plan. The 1st Floor Master has a Large Walk-in closet and master bathroom. Separate shower and Granite countertops. Upstairs boasts a Bonus Room, ample built-in storage, and a 5th Bedroom with a large Walk-in closet. Vaulted Ceilings throughout. The Screened Pool, Covered Lanai, and Large Fenced yard are great for entertaining. The community offers tennis and basketball courts and a 24-hour security guard. New roof in 2024 ($80,000 value). The carpet in the home was replaced in 2020.New A/C replacement in 2024.Termite bond which is transferable. TV's convey with the home in the living room. Pool has been resurfaced. The master bath and kitchen have been updated. This home is located within minutes of downtown Winter Park, Maitland Town Center, shopping, restaurants, hospitals, Genesis Health Club and easy access to I-4.
This listing is courtesy of: ENGEL & VOLKERS ORLANDO DR PHILLIPS
FOREST BROOK 5TH SEC - O6420590 - 726 FOREST GLEN CT, MAITLAND, FL 32751 10 Days on yellowkey
$559,900 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
This beautifully redesigned and renovated move in ready pool home sits on a quiet cul-de-sac in desirable Maitland. Inside, the open floor plan features a brand-new kitchen with quartz countertops, shaker cabinetry, waterfall island, and stainless-steel appliances. Luxury flooring, remodeled baths, and modern finishes run throughout. Major updates include a new roof, newer HVAC, newer water heater, and French doors that open to a large backyard oasis. A bonus room with a mini split AC offers flexibility for an office or gym. Enjoy the private pool, patio, and proximity to top schools, shopping, and dining.
This listing is courtesy of: FLORIDA REALTY OF MIAMI CORP
LAKEWOOD SHORES - O6420264 - 110 N LAKEWOOD CIR, MAITLAND, FL 32751 12 Days on yellowkey
$375,000 | Single Family Home 3 bedrooms, 2.0 bathroom , 2 car carport
Sensational ALL-Block Home in Maitland with NO HOA and Deeded Private Lake Access! Nestled within Lakewood Shores, a charming and welcoming enclave of 42 homes, this 3BR/2BA residence offers a leisurely lifestyle with deeded access to Lake of the Woods via private neighborhood boat ramp. Venture inside to discover an openly flowing traditional layout, soft natural light, well-equipped kitchen w/skylights, separate dining area, and a cozy living room with a wood-burning fireplace. Each bedroom is generously-sized, while the primary bedroom has an en suite w/step-in shower. Enjoy the entertaining possibilities of the screened-in lanai, as well as the fenced-in backyard boasting a shed with electricity connected. Other features: attached carport w/newly epoxy floors, indoor laundry area, new electrical service panel, updated windows/plumbing/water heater, cost-savings well sourced irrigation system, near Maitland Art Center, Lake Lily Park, and the Enzian Theater, close to Downtown Maitland, Park Avenue, Winter Park Village, I-4, and much more! Call and schedule your private showing today!
This listing is courtesy of: BESPOKE REAL ESTATE
DOMMERICH HILLS - O6418744 - 624 TUSCARORA TRL, MAITLAND, FL 32751 13 Days on yellowkey
$945,000 | Single Family Home 5 bedrooms, 3.0 bathroom, 2 car garage
Under contract-accepting backup offers. Welcome to this impressive 5-bedroom, 3-bath split-level POOL home in desirable Dommerich Hills, perfectly nestled on a generous 0.34-acre lot backing to a quiet creek and scenic green space.. Enjoy exceptional privacy and natural beauty with no rear neighbors, creating a peaceful backyard retreat. This remarkable residence offers almost 3400 square feet of living space, providing plenty of room for family living and entertaining. Thoughtfully designed, the home features expansive gathering areas, comfortable bedrooms, and inviting indoor-outdoor living spaces that take full advantage of the beautiful backyard setting. The stunning living room showcases cathedral ceilings with beautiful tongue-and-groove wood detailing, wood burning fireplace creating a warm and inviting atmosphere. French doors open to an expansive outdoor deck overlooking the large backyard and sparkling pool, seamlessly blending indoor and outdoor living. The well-equipped, efficient kitchen is designed for both everyday living and entertaining; appointed with custom shaker cabinetry, granite surfaces, and premium stainless steel appliances serves as the heart of the home. The kitchen boasts a separate breakfast room, with a large picture window capturing beautiful views of the backyard and pool, filling the space with natural light. The oversized primary suite serves as a private retreat, featuring French doors that open to the outdoor deck, an updated en-suite bath, and a large walk-in closet. The secondary bedrooms and guest bath on this level are generously sized and offer ample closet space, providing comfort and flexibility for family members or guests. Downstairs features a spacious family room with a cozy fireplace, two bedrooms, a full guest bath, and a convenient laundry room PLUS wonderful storage room. French doors open to a charming brick terrace overlooking a beautifully manicured backyard that backs onto a peaceful creek. The outdoor space also includes a large swimming pool and a life-size chess/checkerboard area, creating an ideal setting for relaxation and family fun! Recent improvements include windows replaced (2008, 2009), travertine and wood flooring, roof replaced in 2020, A/C' dates2022/2007, freshly painted exterior, and a new sewer connection completed in 2025. A detached two-car garage and long driveway provide abundant parking space, easily accommodating multiple vehicles and making it ideal for guests, recreational vehicles, or a growing family. Ideally located just a short bike ride from highly regarded Dommerich Elementary and Maitland Middle School. Conveniently located just minutes from downtown Maitland, Winter Park, premier shopping, dining, and major roadways, providing easy access to everything Central Florida has to offer. This one-of-a-kind property combines space, privacy, character, and convenience in one remarkable package. Schedule your private showing today and experience all this exceptional home has to offer.
ENGLISH WOODS - O6419597 - 2494 CASTLEWOOD RD, MAITLAND, FL 32751 14 Days on yellowkey
$570,000 | Single Family Home 4 bedrooms, 2.0 bathroom, 2 car garage
Welcome to 2494 Castlewood Road, a beautifully updated pool home situated on a spacious corner lot in one of Maitland's most established neighborhoods. This move-in-ready residence offers peace of mind with a newer roof, solar panels, updated HVAC, and extensive interior renovations throughout. Inside, you'll find an open and inviting floor plan featuring luxury vinyl flooring, updated bathrooms, modern fixtures, quartz countertops, and custom cabinetry. The spacious primary suite includes a walk-in closet and renovated en-suite bath, while the additional bedrooms provide flexibility for family, guests, or a home office. A large screened Florida room overlooks the backyard and creates the perfect space for year-round entertaining. Outside, enjoy the oversized swimming pool, expansive patio deck, fully fenced yard, and storage shed, offering plenty of room for recreation and outdoor living. Conveniently located just minutes from Downtown Maitland, Winter Park, Park Avenue, AdventHealth, shopping, dining, and major roadways including I-4, this home combines modern updates, energy-efficient features, and an exceptional location in the heart of Central Florida.
This listing is courtesy of: LA ROSA REALTY CW PROPERTIES L
ORANGEDALE PARK REP - O6419510 - 245 ORANGE PL, MAITLAND, FL 32751 15 Days on yellowkey
$675,000 | Single Family Home 4 bedrooms, 3.0 bathroom
Under contract-accepting backup offers. Location, location!! Discover a rare opportunity to own a single family home plus 2 ADUs, just steps from the iconic Enzian Theater and vibrant Downtown Maitland. This property features three separate units, each with three separate electric meters, water meters and IN-UNIT washer and dryers - a highly sought-after feature for both tenants and owner-occupants alike.With all exterior siding replaced in 2026 on all three units, newer roofs installed in 2026 and 2021, and updated kitchens already completed, this property offers an exceptional turnkey investment with major improvements already in place for long-term peace of mind. This property also has ample parking and an oversized storage shed. The main house is a spacious 2 Bed/1 Bath unit (currently rented for $1,950/month), Unit 2 is a 1 Bed/1 Bath rented for $1,500/month, and Unit 3 is a studio rented for $1,100/month. Current rents are currently below market value and all three units are occupied by long-standing tenants who provide dependable income and minimal turnover. All three leases are set to expire in July and August of 2026, providing future flexibility for an investor or owner-occupant, and two of the tenants have already indicated interest in extending their leases, offering continued income stability from day one. Whether you’re looking to expand your investment portfolio, take advantage of a house-hacking opportunity, or explore the potential for short-term rental income, this property offers exceptional versatility in one of Central Florida’s most sought-after locations. Live in one unit while generating income from the others, or maximize returns through a strategic blend of long-term and short-term rental options. Location truly sets this property apart. Enjoy being just minutes from Winter Park Village, offering endless shopping, dining, entertainment, and a movie theater, while also being a short drive from the charm and excitement of Park Avenue and everything Winter Park has to offer. Residents will love easy access to weekend farmers markets in both Maitland and Winter Park, nearby grocery stores, top-rated restaurants, local boutiques, and convenient commuter routes. The property is also located near Rollins College, adding even more appeal to the location.
This listing is courtesy of: ONE LUXURY INTERNATIONAL LLC
KINGS ROW - O6418693 - 1615 KING ARTHUR CIR, MAITLAND, FL 32751 18 Days on yellowkey
$1,386,000 | Single Family Home 4 bedrooms, 3.0 bathroom, 2 car garage
Beautifully updated pool home in the sought-after King's Row, Maitland community. This home blends timeless character with modern finishes. The corner lot residence features a three wide driveway, freshly updated landscaping and a commercial grade in ground basketball goal. Exterior paint (2026) creates warm curb appeal. Inside, new wood floors throughout lead to an open living space anchored by an updated kitchen and a classic painted brick wall. The renovated kitchen features quartz countertops, custom cabinetry, pendent lighting, stainless appliances and an updated Fisher Paykel refrigerator. A large island provides seating for four makes entertaining quick and simple. An updated hall pool bath provides easy access for guests both inside and out. Steps away the multi tasked laundry/utility drop/zone is conveniently located off the rear double garage entrance. A commercial grade Speed Queen washer in the laundry/utility room assures your clothes will be clean. Also, an adjacent wall of cabinetry increases the incredible storage in the home. Not only in the front but in the back the corner lot offers an ample spaced backyard retreat. Added is a screened and covered lanai perfect for outdoor parties and gatherings as does the oversized in-ground pool. Zoysia grass/lush landscaping and lighting continue the resort feel. A newer, horizontal stained wood fence adds privacy while maintaining charm. Back inside the living room, a rattan light fixture adds to the ambiance of this bright natural light space. Next to the living space, an office that features a set of French doors lends a place for quiet conversation. The generously sized family room with the afore mentioned painted brick wall is complete with large windows overlooking the sparkling pool and views of three whimsical palms. Down the hallway the newly installed designer wood flooring continues to all bedrooms. Every bedroom just received fresh paint, as well as the newly installed wood floors. All closets feature custom built-ins that add to the level of sophistication/quality in this home. The primary bedroom features another custom painted brick wall with updated sconce lighting. Still another set of French doors lead out to the pool and lanai. The owner's bath features a double vanity with stone counter-tops and updated lighting and faucets. A Mitered frameless glass shower is a great addition to the richness of the space. Zoned for Dommerich Elementary, Maitland Middle, Ninth Grade Center and Winter Park High the schools are highly desirable. A quick and easy close can be the start of your next chapter. This Move-in ready home awaits......
This listing is courtesy of: CORCORAN PREMIER REALTY
FOREST BROOK 5TH SEC - S5152100 - 741 BROOKSIDE RD, MAITLAND, FL 32751 19 Days on yellowkey
$629,950 | Single Family Home 4 bedrooms, 2.0 bathroom, 2 car garage
Welcome to 741 Brookside Road in the heart of Maitland! This beautifully updated 4-bedroom, 2-bath pool home offers the perfect blend of modern upgrades, spacious living, and an unbeatable location. No expense was spared during the home's extensive renovations, creating a truly move-in-ready property that combines quality craftsmanship with timeless style. The recently remodeled kitchen is a true showpiece, featuring solid wood cabinetry, elegant Taj Majal granite countertops, upgraded appliances, and abundant workspace for cooking and entertaining. Recent improvements throughout the home include fresh interior paint, a newly renovated guest bathroom, updated plumbing, and a new roof installed in 2024, providing peace of mind for years to come. At the heart of the home is an enormous Florida Room, offering exceptional space for gathering with family and friends while overlooking the tropical backyard retreat. Step outside to your private oasis, complete with a sparkling pool and fountain surrounded by lush landscaping that creates a serene, resort-style atmosphere. Situated on a large fenced corner lot with no HOA, this property offers both privacy and freedom. Its fantastic Maitland location places you just minutes from shopping, dining, parks, and major roadways, making everyday living both convenient and enjoyable. You will be hard-pressed to find another property in this location and price range that offers this level of attention to detail, quality of construction, and thoughtful upgrades throughout. Every improvement has been carefully selected to create a home that is as functional as it is beautiful. Move-in ready and loaded with updates, this rare opportunity combines comfort, style, and outdoor living in one exceptional package. Schedule your private showing today and discover everything this beautiful Maitland home has to offer! Square footage includes Florida Room of 336 square feet not included on tax records.
This listing is courtesy of: TRANSCEND REALTY
VILLAS LAKE DESTINY - O6417777 - 1010 WINDERLEY PL #149, MAITLAND, FL 32751 19 Days on yellowkey
$429,900 | Townhouse 3 bedrooms, 2.0 bathroom, 2 car garage
This beautifully positioned residence offers an open and inviting layout designed for easy living and entertaining. Enjoy peaceful water views of Lake Destiny with no rear neighbors, creating a private backdrop and a rare sense of space and tranquility. Whether relaxing indoors or stepping outside, the serene setting delivers a true sense of comfort and escape. The home also features a spacious 2-car garage, providing convenience and additional storage. Thoughtfully updated and move-in ready, this home offers valuable recent improvements including a new A/C unit (2022), water heater (2022), tile roof replacement (2022), updated paint and modern light fixtures (2023), and both bathrooms beautifully renovated in 2021. The kitchen is complemented by newer appliances, adding both style and functionality. Step outside and enjoy even more value with the outdoor deck currently being replaced, creating an enhanced outdoor living space to take in the beautiful lake setting. Residents enjoy access to exceptional community amenities including a pool, tennis courts, and access to Lake Destiny, all within a dog-friendly community designed to support an active and enjoyable lifestyle. Ideally located with quick access to major highways, dining, shopping, business centers, and everything Maitland and the greater Orlando area have to offer, this property delivers the perfect blend of lifestyle and accessibility. Whether enjoying your morning coffee overlooking Lake Destiny or coming home after a busy day, this residence offers the privacy, views, updates, and location today’s buyers are searching for.
This listing is courtesy of: GENSTONE REALTY
LAKE MAITLAND TERRACE APTS - O6415783 - 1140 S ORLANDO AVE #H3, MAITLAND, FL 32751 20 Days on yellowkey
$439,900 | Condo 2 bedrooms, 1.5 bathroom
Virtually Staged. RARE LAKEFRONT opportunity to Live right on LAKE MAITLAND! Sip your morning coffee with one of the most premier views in the entire community! BONUS: It's on the main FIRST floor, so NO STAIRS! Just a pure unencumbered view of Lake Maitland right from your living room! And only a few steps to the dock or community pool!! This unit has the EXTRA HALF BATHROOM and has been tastefully updated to accentuate it's incredible mid century modern original features, that are in immaculate condition! There may never be another unit quite like this one! The high end plantation shutters offer privacy when needed, but can stay wide open for that view! Enjoy the remodeled Community POOL & Clubhouse all on the stunning water front of Lake Maitland which is also connected to the Winter Park Chain of Lakes. Plenty of fishing, fun and relaxing to be had on the community dock, shuffleboard and putting green! So many amenities nestled amongst the towering shade trees and mature landscaping. The Mid Century Modern architecture is about as timeless of a look that you can find that fits the Maitland/Winter Park lifestyle. You couldn't ask for a better location at just minutes from downtown Winter Park, Park Ave, SunRail station and all the restaurants surrounding the 17/92 Maitland/Winter Park Corridor. All Units recently had metal roof replacement in 2025 and were just freshly painted as well. It's completely move in ready with all New Luxury Vinyl Plank Flooring, Kitchen and bathroom updates,. This unit has not been available for many years, so don't miss out on this view!
This listing is courtesy of: UNITED REAL ESTATE PREFERRED
LAKEWOOD SHORES 1ST ADD - O6418229 - 195 CEDARWOOD DR, MAITLAND, FL 32751 20 Days on yellowkey
$800,000 | Single Family Home 3 bedrooms, 2.5 bathroom, 2 car garage
Under contract-accepting backup offers. Nestled on the shores of skiable Lake of the Woods, this beautifully maintained 3-bedroom, 2 and a half bath waterfront residence offers over 105 feet of private lake frontage with breathtaking open-water views. Designed for those who embrace the lake lifestyle, the property features a private boat launch, two docks, and a solar-powered boat lift, providing effortless access to one of Central Florida's most desirable private lakes. Inside, vaulted ceilings and abundant natural light create an inviting atmosphere, while the updated kitchen opens seamlessly to the living and dining spaces, making everyday living and entertaining a pleasure. The primary suite enjoys peaceful water views, and the home's coastal-inspired finishes enhance the relaxed lakefront setting. A spacious rear deck overlooks the water and serves as the perfect place to enjoy sunrise coffee, sunset gatherings, and weekends on the lake. Additional highlights include a durable metal roof, wood floors, mature landscaping, generous outdoor living spaces, and a prime Maitland location convenient to shopping, dining, top-rated schools, Winter Park, and Downtown Orlando. Rarely does an opportunity arise to own a move-in ready waterfront home with this combination of frontage, amenities, and direct access to skiable waters.
This listing is courtesy of: COMPASS FLORIDA LLC
SUN BAY CLUB CONDO UT 1 - O6417569 - 1000 WINDERLEY PL #141, MAITLAND, FL 32751 20 Days on yellowkey
$300,000 | Condo 2 bedrooms, 2.0 bathroom
Updated GROUND-FLOOR condo in the secluded gated community of Sun Bay Club in Maitland, Florida overlooking Lake Destiny. Many units sit on lake fed ponds with fountains which offer a tranquil and peaceful atmosphere. Enjoy Florida life with a tennis court, a beautiful LAKE FRONT POOL, and LAKE ACCESS for residents to use boats and jet skis. The open-concept layout makes this 2 bedroom/2 bath condo feel so spacious. The LARGE KITCHEN (renovated 2023) features white kitchen cabinets, quartz countertops, a newer microwave (2024), and a 2025 dishwasher. Wood-look tile flooring flows through living areas connected to wood flooring throughout - no carpet! Extended sliding glass doors open to an ENCLOSED SUNROOM with windows and a peaceful pond view. Use it as a home office, reading room, or morning coffee retreat. Additionally, each bedroom has it's own screened in patio! The primary suite features double entry doors, access to both the enclosed sunroom and it’s own screened patio. It’s also equipped with a WALK-IN CLOSET with built-in shelving and an UPDATED 2026 ENSUITE BATHROOM with a new double sink vanity, modern mirrors, lighting, and a pocket door providing privacy to the shower and water closet room. The second bedroom offers DOUBLE CLOSETS with built-in shelving as well. HALLWAY BATHROOM UPDATED in 2026 with new vanity, mirror and lighting. HOA INCLUDES internet/cable and takes care of everything exterior including roof. Minutes from Maitland and Winter Park shopping, dining, and just a few minutes drive to highway I-4. Schedule a viewing today!
This listing is courtesy of: EXP REALTY LLC
ENCLAVE AT MAITLAND A-F - G5113516 - 1404 CARING CT, MAITLAND, FL 32751 20 Days on yellowkey
$659,500 Reduced | Single Family Home 3 bedrooms, 2.5 bathroom, 2 car garage
"RARE OPPORTUNITY" MOVE-IN READY 3-BED, 2.5-BATH SINGLE FAMILY HOME IN THE "EXCLUSIVE GATED COMMUNITY OF ENCLAVE AT MAITLAND", FL 32751. Nestled within the highly sought-after & gated community of Enclave at Maitland, Single Family Homes rarely come on the market and this home offers a Luxury Interior Footprint that's a perfect balance of privacy, elegance, and convenience. Fully updated & loaded with high-end finishes, the triple split-plan layout features separate Formal Dining & Family Rooms that maximize both entertaining and day-to-day privacy. Enter through a HUGE 21' Long Foyer into the Large Family Room which boasts a 14' High Tray Ceiling and the Centerpiece of the home. Just off the Family Room is the Formal Dining room, perfect for entertaining & family dinners. The Kitchen is perfectly designed for the Serious Chef, boasting Level 3, 42" Maple Cabinetry with Upper Crown Molding, Premium Granite, Center Island with a (3) Person Breakfast Bar, Stainless Appliance Package including Double Built-In Ovens, French Style Refrigerator, Flat-Top Range, Tons of Counter & Storage Space, Dual Stainless Sink, Custom Tile Backsplash, Pendant & Recessed Lighting, Closet Pantry and an adjoining Sunlit Dinette that provides the perfect spot for casual morning coffee. The Primary Suite is the Perfect Couples Retreat! The Bedroom is generous in size and will accommodate all of your oversized furniture & features a HUGE Tray Ceiling, Crown Molding, Laminate flooring, and Dual Walk-In Closets outfitted w/Custom Storage Organizers. The En-Suite Bathroom offers His-and-Her Maple Vanities w/Undermount Sinks, Granite Counters, Deep Garden Soaking Tub wrapped in Custom Tile, Large Walk-In Shower engineered with Dual Shower heads at opposite ends, Under-Cabinet Accent Lighting and a Glass Block Window for lots of natural lighting. On the opposite side of the residence, Two Additional Bedrooms share a beautifully appointed Full Bathroom, offering an ideal setup for Children & Guests. If you work from home or just looking for a quiet space, you'll enjoy the Private Office/Den located just off the Family Room. The Interior Laundry Room is highly functional and included Front-Load Washer & Dryer, Integrated Wash Tub/Sink & Upper Storage Cabinets. Your living space effortlessly expands outdoors through a Triple-Slider to the 12'x16' Covered Back Porch w/Premium Slate Tile flooring. Here, you can unwind against the peaceful backdrop of an unobstructed Lake View & Conservation Area. Additional Features: Prestigious Maitland Lifestyle, Low-Maintenance Luxury, Directly Across from the Pool, Block & Stucco, Barrell Tile Roof, Freshly Painted Inside & Out, High Ceilings Throughout, Carrier HVAC (2021), Vacuflo Central Vac System, GE Hybrid 50 Gal Water Heater (2016), Double-Paned Windows, 18x18 Tile Flooring Flowing Diagonally, Premium 8" Crown Molding, Elegant Custom Arches, Tray Ceilings, 8’ High Doors, Upgraded 6" Baseboards, Surround Sound Speaker & Prewire, Security System, Ceiling Fans/Light, Pre Plumbing for Summer Kitchen, Epoxy Coated Garage Floor and (2) Garage Door Openers, Custom Garage Storage, Paver Driveway, Beautiful Palms, Magnolias & Ivy, Private Mailbox, Irrigation System and more. Incredible location close to I-4, Downtown Maitland, Altamonte & Orlando, Shopping, Dining, Theme Parks, Turnpike, Beaches and all Central Florida has to offer. Call today for more info or schedule a private showing. This is Move-In Ready Perfection!
This listing is courtesy of: ROCK SPRINGS REALTY, LLC
VISCONTI WEST CONDO - O6416664 - 1440 LAKE SHADOW CIR #8201, MAITLAND, FL 32751 25 Days on yellowkey
$199,000 | Condo 2 bedrooms, 2.0 bathroom
If you are looking for a terrific property, look no further! You or your tenant can live the lifestyle deserved in this RESORT-STYLE, video-monitored GATED COMMUNITY located on beautiful Lake Shadow in the heart of Maitland Center. This two-bed/two-bath, 2nd-story, CORNER UNIT features an OPEN floor plan with a LIVING/DINING COMBO and 9-FOOT CEILINGS. The KITCHEN includes a breakfast bar, closet pantry, INSIDE UTILITY CLOSET with washer and dryer, and neutral tile. All appliances convey at closing. DOUBLE MASTERS each offer an en-suite bath and a walk-in closet. The 20 X 20 living area provides lots of sunlight and features a built-in nook with glass shelving you can use as you choose. In 2024, the interior was painted, and carpet was installed. Through sliders, you can unwind at the end of a busy day on the SCREEN-ENCLOSED tiled LANAI and enjoy a TRUE ESCAPE. If extra storage is needed, a patio closet awaits! This GORGEOUSLY LANDSCAPED and PET-FRIENDLY community offers two LAKESIDE POOLS with Wi-Fi access, a club-quality FITNESS CENTER, grand CLUB ROOM with CATERING KITCHEN, fully-equipped BUSINESS CENTER, lighted TENNIS courts, BASKETBALL court, car wash area, two laundry facilities, 24-HOUR MAINTENANCE, WATER, SEWER, and a Monday-Friday VALET WASTE REMOVAL SERVICE. The condo community boasts a newer tile roof, reflecting ongoing care and investment in the property. Located minutes away from SR 414, I-4, 429, Routes 434 and 436; it is a quick drive to downtown Orlando, Cranes Roost Park, and to the upscale shopping and dining at Altamonte Mall, Altamonte Towne Center, Winter Park Village, and Winter Park’s quaint Park Avenue. Enjoy Florida living at its best! This property may be under audio & visual surveillance.
This listing is courtesy of: COLDWELL BANKER REALTY
HIGHLAND PARK ESTATES FIRST ADD - R4911437 - 2491 LAUDER DR, MAITLAND, FL 32751 25 Days on yellowkey
$1,299,000 | Single Family Home 5 bedrooms, 4.0 bathroom, 2 car garage
Completely reimagined and renovated, this artfully crafted stunning 5-bedroom, 4-bath residence offers approximately 2,695 square feet of on a spacious corner lot in one of Maitland's most desirable established neighborhoods. The home features an exceptional blend of modern design, luxury finishes, and functional living spaces, including a sparkling pool and expansive outdoor entertaining areas. Step inside to discover an impressive open-concept floor plan highlighted by wide-plank luxury flooring, designer lighting, oversized windows, and a dramatic double-sided tiled fireplace that serves as the centerpiece of the main living areas. The gourmet kitchen has been thoughtfully designed with Kitchen-aid "Black-Ore" Professional series applainces, custom shaker cabinetry, quartz countertops, a large center island, designer backsplash, butlers pantry with wine fridge, and abundant storage, creating the perfect space for everyday living and entertaining. The spacious primary suite offers a private retreat with generous proportions, elegant finishes, and a beautifully appointed spa-inspired bathroom featuring dual vanities, custom cabinetry, a frameless glass walk-in shower, and designer fixtures. Additional bedrooms provide flexibility for family, guests, home offices, or multi-generational living. Outdoor living is equally impressive with a screened covered lanai overlooking the newly resurfaced pool and expansive paver deck, creating a resort-style setting ideal for entertaining year-round. The large fenced backyard offers plenty of room for recreation, pets, and outdoor enjoyment. Located just minutes from Park Avenue, Winter Park, Maitland City Centre, top-rated schools, dining, shopping, and major roadways, this turnkey residence offers luxury living in a prime Central Florida location. A rare opportunity to own a fully renovated pool home that combines timeless architecture with today's most sought-after finishes and amenities.
This listing is courtesy of: HOLSTON PROPERTIES & DEV., INC
DOMMERICH ESTATES 1ST ADD - O6414036 - 1781 TONTO TRL, MAITLAND, FL 32751 26 Days on yellowkey
$600,000 | Single Family Home 4 bedrooms, 2.0 bathroom, 2 car garage
Under contract-accepting backup offers. Welcome to 1781 Tonto Trail, a 4-bedroom home in one of Maitland's most desirable neighborhoods, offering just under 1,900 square feet of living space, a split bedroom floor plan, and access to the Winter Park Chain of Lakes. Located on a corner lot just under a quarter acre, this move-in ready residence combines functionality, comfort, and an exceptional Maitland location. Inside, you'll find a formal living room and formal dining room that provide flexible spaces for entertaining, working from home, or everyday living. The spacious family room serves as a central gathering area and connects seamlessly to the home's thoughtful layout. The private primary suite features an ensuite bathroom and double closets, creating a comfortable retreat. Bedrooms two and three offer large walk-in closets, providing abundant storage and flexibility for family, guests, or home office needs. The split bedroom design enhances privacy while maintaining a practical flow throughout the home. Residents of Dommerich Estates enjoy access to highly regarded schools including Dommerich Elementary, Maitland Middle School, and Winter Park High School. A voluntary low-cost HOA provides access to a private boat ramp on the Winter Park Chain of Lakes, creating opportunities for boating, fishing, paddleboarding, and waterfront recreation. The location places you short distance to the Maitland Community Park, Maitland Social, and Maitland City Centre, offering convenient access to local dining, recreation, events, and community amenities. Whether you're looking for more space, access to top-rated schools, or the lifestyle benefits of a lake-access community, this 4-bed home in Dommerich Estates delivers a rare opportunity to enjoy one of Maitland's most established and sought-after neighborhoods.
REPLAT BLK B POORS ADD - O6415928 - 255 W GEORGE AVE, MAITLAND, FL 32751 26 Days on yellowkey
$1,499,000 | Single Family Home 5 bedrooms, 4.0 bathroom, 2 car garage
A premier street offering an accessible lifestyle to Maitland’s vibrant downtown corridor, known for its community events, restaurants, Lake Lily Park, the beloved independent Enzian Theater and within view of Lake Sybelia. This custom home was completely rebuilt in 2007, adding significant square footage and incorporating a timeless transitional design. Five bedrooms, four baths, stretching across 4,814 square feet with bonus space, there are many ways to make it your own. Inspired by classic Charleston architecture with Florida influences, the exterior features French doors across the front and rear elevations, lantern-style lighting and a metal roof that enhance the home's charm while filling the interiors with natural light. Shutters and upper-level balconies at both sides of home complete the design. Enter inside to a sweeping staircase with elegant iron details, with neutral travertine flooring that flows throughout the main level and finished with volume ceilings. The kitchen, living and dining spaces blend seamlessly together, complemented by an additional sitting room with privacy doors that provide flexible living options. The kitchen features 42-inch custom cabinetry with glass-paneled doors, granite countertops, a farmhouse sink and high-end stainless-steel appliances. Generous laundry and pantry storage are bonus. The dining area showcases rich hardwood flooring, plantation shutters, built-in surround-sound speakers and direct access to outdoor living spaces. The first floor includes two bedrooms with a shared bath, along with an additional hallway guest bath. Upstairs, beautiful wood floors anchor the rooms, and the spacious primary retreat opens to a private balcony spanning across the back of home and with pool views. An expansive walk-in closet provides exceptional organization, while the primary bath features dual vanities, a rain shower with bench seating and a classic clawfoot tub. Additional upstairs laundry stack for convenience. Secondary bedrooms are spacious and full of light, and great closet storage and additional loft are a bonus. Outdoor living centers around a covered porch overlooking the pool, complete with travertine decking and dramatic fountain features. An additional pool house enhances the backyard and offers endless possibilities for guests, entertaining or a private workspace. Outdoor speaker system adds to the ambience. Additional improvements and features include a newer metal roof (2020), two HVACs (2021), water heater (tankless Rinnai installed by Maitland/Winter Park plumbing), plantation shutters throughout, a freshly painted interior, an extensive interior and exterior lighting package, and thoughtfully designed low-maintenance landscaping featuring front-yard turf, mature plantings and clean rock-bed borders. Exterior ceramic paint has a lifetime warranty. Main floor and primary suite have ceiling-installed concert speakers and outdoor speakers. Lower-floor speakers have individual room controls and are served by a pantry stereo system. This exceptional home offers a desirable location with convenient access to major roadways. Zoned for sought-after schools including Lake Sybelia Elementary, Maitland Middle School and Edgewater High School, a designated magnet school, Park Maitland elementary school, and JCC community center and school. A rare opportunity, this home is a standout in one of Maitland’s special neighborhoods.
This listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY
MAITLAND GROVE - O6414895 - 151 WHITE OAK CIR, MAITLAND, FL 32751 27 Days on yellowkey
$699,000 Reduced | Single Family Home 4 bedrooms, 2.5 bathroom, 2 car garage
Under contract-accepting backup offers. Offering endless possibilities in the highly sought-after Maitland Grove neighborhood, this spacious 4-bedroom, 2.5-bath pool home offers the perfect opportunity to create something truly special. Major improvements are already in place, including a newer roof (2023), A/C (2021), updated electrical panel (2026), also appears to have been replumbed, providing a strong foundation for future updates and personal touches. Outdoor living takes center stage with an oversized screened porch overlooking the swimming pool and expansive 12,528-square-foot lot, offering ample space for entertaining, recreation, or creating your own backyard retreat. Inside, the family room is anchored by a wood-burning fireplace and opens to the porch through French doors, creating a natural connection to the outdoors. The light-filled kitchen features a large picture window, breakfast bar, and seamless flow into the family room, making it an inviting space for everyday living and gathering with friends and family. Designed with entertaining in mind, the combined living and dining rooms extend to the screened porch through sliding glass doors, enhancing the home's spacious feel and creating an easy transition between indoor and outdoor living spaces. Additional features include an indoor laundry room and a side-entry two-car garage. Beyond the home, residents enjoy an exceptional location just a short stroll from Homer Hough Park at Lake Sybelia Point, where lakeside green spaces, a playground, fishing pier, picnic areas, and peaceful waterfront views provide the perfect setting for outdoor enjoyment. Lake Sybelia Elementary School and Orangewood Christian School are both within walking distance, adding everyday convenience to an already desirable setting. Ideally positioned near shopping, dining, I-4, and the Maitland Center business district, the home also offers easy access to the boutiques, restaurants, and cultural attractions of Winter Park. Combining a tranquil neighborhood setting with outstanding convenience, this residence offers the rare chance to create lasting value while making a home uniquely your own in one of Maitland's most established and coveted communities. Don't miss your chance to make it your own—call today to schedule your private showing!
VISCONTI EAST BLDG 27 - O6414837 - 2847 SHADOW VIEW CIR #2847, MAITLAND, FL 32751 27 Days on yellowkey
$210,000 | Condo 2 bedrooms, 2.0 bathroom, 2 car garage
Visconti Condo - Gated Community with lots of amenities only 8 miles from Downtown Orlando. This community situated on the north shore of Lake Shadow offers swimming pool, fitness center, clubhouse, tennis and basketball courts. Conveniently located close to I-4 and Maitland Blvd. Multi level home features an open floor plan with kitchen living/dining and office on main 2nd floor and 2 bedrooms 2 bathrooms on the 3rd floor. This home also features an attached 2 car garage with plenty of room for your vehicles or extra storage. HOA includes exterior maintenance, landscaping, valet trash, water, sewer and pest control.
This listing is courtesy of: MARKET CONNECT REALTY LLC
HIGHLAND PARK ESTATES FIRST ADD - O6414213 - 830 LONGHAVEN DR, MAITLAND, FL 32751 28 Days on yellowkey
$675,000 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
Under contract-accepting backup offers. Welcome to this beautifully maintained 3 bedroom, 2 bath pool home offering 2,229 square feet of living space in the highly sought-after Dommerich neighborhood of Maitland. The heart of the home is the spacious kitchen featuring knotty pine cabinetry, granite countertops, a gas range, stainless steel appliances, a breakfast bar, and an elegant tray ceiling. The kitchen opens seamlessly to the family room, where a stunning brick accent wall showcases a cozy fireplace and a unique alcove perfect for indoor grilling and entertaining. A separate living room offers additional gathering space with its own fireplace and custom built-in bookshelves. The formal dining room is highlighted by a beautiful chandelier. French doors lead you to a spacious bonus room built in 2025, which is filled with natural light from new windows, providing endless possibilities for a home office, playroom, or flex space. Step outside to your private backyard retreat featuring a sparkling 10-foot-deep pool surrounded by classic herringbone-style pavers, creating the perfect setting for relaxation and outdoor entertaining. An outdoor storage shed provides added convenience. Recent updates include a brand-new roof (2026), newer windows, attractive wood shutters throughout, AC (2015), and water heater (2015) and indoor laundry room. Located within the highly acclaimed Dommerich Elementary, Maitland Middle, and Winter Park High School districts, this home offers the perfect blend of character, comfort, and location—don't miss this rare opportunity to make it yours.
ENGLISH ESTATES UNIT 2 - O6414229 - 1291 OXFORD RD, MAITLAND, FL 32751 28 Days on yellowkey
$419,000 Reduced | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
Under contract-accepting backup offers. Virtually Staged. HUGE PRICE IMPROVEMENT!!! Move-In Ready Maitland Gem in English Estates! Welcome home to this charming 3-bedroom, 2-bath residence offering convenient one-story living in the highly desirable English Estates community. Blending modern updates with a touch of mid-century modern character, this home is truly turnkey. Step inside to find luxury vinyl plank and ceramic tile flooring throughout—no carpet anywhere. The updated kitchen features granite countertops, 42-inch cabinetry, stainless steel appliances, and a breakfast bar perfect for casual dining and entertaining. The spacious living room flows seamlessly into the dining area, creating an open and inviting atmosphere. The private primary suite includes an en-suite bathroom, while the generously sized secondary bedrooms provide flexibility for family, guests, or a home office. A separate den/family room offers additional living space and opens to a covered, screened porch overlooking the expansive fenced backyard—ideal for outdoor gatherings, pets, and play. Major updates provide peace of mind, including New Roof (2024) HVAC System (2021) Whole-House Repipe (2021) Irrigation System (2022) Septic Drain Field (2018) Double-Pane Windows, New Sod (2026) Additional features include a 2-car garage, paver driveway, covered front porch, and fresh paint. Conveniently located near shopping, dining, parks, and major roadways, with easy access to Winter Park and surrounding Central Florida attractions. Plus, enjoy the benefit of highly regarded Seminole County Public Schools. Beautifully updated, exceptionally maintained, and truly move-in ready—this is a home you won't want to miss!
ENCLAVE/MAITLAND A-F - O6414938 - 1149 CHARMING ST, MAITLAND, FL 32751 28 Days on yellowkey
$590,000 | Townhouse 4 bedrooms, 3.5 bathroom, 2 car garage
The Enclave at Maitland (Montacino), Beautifully Updated, First Floor Primary Bedroom, Oversized 20' x 26' Garage, Gated Community Living in the Enclave at Maitland which is highly sought-after, offering the perfect blend of style, comfort, and maintenance-free living. This fully updated Spanish-style townhome features 4 bedrooms, 3.5 bathrooms, a private paver courtyard, and an oversized attached two-car garage measuring approximately 20' x 26'—providing valuable extra space for storage, hobbies, a workshop area, or larger vehicles. One of the home's most desirable features is the spacious first-floor Primary Suite, offering privacy and convenience along with a beautifully updated en-suite bath featuring dual vanities, a soaking tub, separate shower, and walk-in closet. The thoughtfully designed floor plan is enhanced by soaring 9'8" ceilings on the main level, extensive crown molding, ceiling fans, and abundant natural light throughout. At the heart of the home is a stunning remodeled kitchen featuring 42-inch cabinetry with crown molding, granite countertops, stainless steel appliances, breakfast bar seating, and a cozy breakfast nook overlooking the private courtyard. The kitchen, all bathrooms, and even the laundry room have been tastefully updated, providing a move-in-ready experience for the next owner. You've got to see it! Upstairs you'll find a second private suite with its own updated bathroom, two additional bedrooms, another full bath, and a conveniently located laundry room. Closet organizer systems throughout the home provide exceptional storage and functionality. Residents enjoy access to a resort-style community pool overlooking picturesque Lake Charity, all within the security and convenience of a gated neighborhood. Ideally located near Maitland Boulevard and I-4, this exceptional location provides easy access to Downtowns of Orlando, Maitland and Winter Park, with premier shopping, dining, entertainment, and major employment centers. Offering a rare combination of updated finishes, flexible living space, oversized garage storage, and an unbeatable location, this exceptional townhome is ready to impress even the most discerning buyers.
This listing is courtesy of: YOUNG REAL ESTATE
CARRINGTON PARK A CONDO - O6412669 - 550 FLEMMING WAY #100, MAITLAND, FL 32751 33 Days on yellowkey
$129,000 Reduced | Condo 2 bedrooms, 1.0 bathroom
Bright and well maintained 2 bedroom, 1 bath condo located in a desirable shopping and dining area! This inviting home features abundant natural light, a spacious walk-in closet in the primary bedroom, and a relaxing enclosed patio perfect for additional living space or entertaining. The HOA includes water for added convenience. Residents also enjoy access to a community pool and low-maintenance living close to everything you need. Great opportunity for homeowners or investors alike!
This listing is courtesy of: LOKATION
WINFIELD - S5151303 - 2155 FENNELL ST, MAITLAND, FL 32751 33 Days on yellowkey
$489,900 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
Welcome to 2155 Fennell Street, a beautifully renovated pool home nestled in the desirable Maitland community. This move-in ready residence has undergone an extensive transformation, offering the perfect blend of modern elegance, functionality, and Florida lifestyle living. From the moment you arrive, you'll appreciate the brand-new roof, new driveway, fresh exterior paint, and impressive curb appeal. Inside, soaring vaulted ceilings and abundant natural light create a bright and inviting atmosphere. The open-concept floor plan features luxury vinyl plank flooring throughout, designer lighting, and fresh interior paint. The fully remodeled kitchen is the heart of the home, showcasing quartz countertops, custom cabinetry, stainless steel appliances, and a spacious breakfast bar overlooking the main living areas. The primary suite offers a private retreat with a beautifully updated ensuite bath featuring dual vanities, designer finishes, and a stunning walk-in shower. Additional bathrooms have been tastefully renovated with modern fixtures and custom tile work. Step outside to your private backyard oasis complete with a resurfaced swimming pool, screened lanai, and fully fenced yard—perfect for entertaining, relaxing, and enjoying year-round Florida sunshine. Conveniently located near shopping, dining, parks, major highways, and top area amenities, this exceptional property offers the rare opportunity to own a truly turnkey home in one of Maitland's most sought-after locations. Schedule your private showing today and experience this stunning home.
This listing is courtesy of: TCA REALTY, LLC
VERSAILLES - O6413200 - 908 VERSAILLES CIR, MAITLAND, FL 32751 33 Days on yellowkey
$899,000 | Single Family Home 4 bedrooms, 2.0 bathroom, 2 car garage
Under contract-accepting backup offers. Ideally in one of Maitland’s desired neighborhoods, Versailles, this fully renovated home blends timeless architecture with modern comfort. With sun-filled interiors, an open-concept layout, a serene primary suite and freshly landscaped grounds, every detail supports effortless living. This three-bed, two-bath home stretches over 2,151 square feet and is situated on 0.29 of an acre. This classic ranch style offers a split bedroom plan with endless function. A gracious foyer welcomes you into this serene space with blonde oak flooring, limewash accent walls, a vaulted ceiling with wood beam accents, fresh neutral tones, designer fixtures and ambient lighting that softens the spaces. This home features formal dining and a flex space that could be a fourth bedroom or office, offering many layout choices. The combined kitchen and living room showcases a wood-burning fireplace with a fluted marble surround as the focal point. The kitchen combines crisp, clean-lined cabinets and warm-wood-toned floor-to-ceiling storage cabinets finished with brushed-gold hardware. A waterfall center island with quartz counters that continue up the backsplash for a stylish design. Clear view sliders open to a covered porch with a tongue and groove ceiling feature and is part of a screened pool, making entertaining a breeze. Recently installed turf grass for ease of maintenance and keeps it all looking very fresh. The pool was recently refinished and a side-yard sauna rounds out this oasis. The primary suite is a private retreat with an oversized walk-in shower with beautiful vertical Zellige tile. Dual vanities with custom arched mirrors, sconce lighting and porcelain-marble floors add to the space. Built-in linen closets and dual bedroom closets make organization simple. Additional highlights include both baths completely renovated, new kitchen appliances (LG/GE stainless steel) induction range, new interior doors and hardware, new ceiling fans, new Pella front doors and Impervia slider doors across the back of the home, new Pella front windows, a new Hass garage door (2025), the whole yard professionally designed and landscaped (2026), a sauna (2024), a roof (approximately 2018) and a water heater (2023). This neighborhood enjoys a community lake lot with access to Lake Minnehaha, part of the Winter Park lake chain. Strategic location close to major roadways, short distance to the Sunrail and close to all amenities that make Maitland special. Zoned for some of the best Orange County schools: Lake Sybelia, Maitland Middle and Winter Park High, a nationally renowned school for its International Baccalaureate Program.
PINDAR SUB - O6414097 - 206 MOSELEY AVE, MAITLAND, FL 32751 33 Days on yellowkey
$449,000 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
Under contract-accepting backup offers. Inside, the home opens into a bright and airy open-concept living space highlighted by high tray ceilings, recessed lighting, oversized glossy tile flooring, and an abundance of natural light. The seamless flow between the living, dining, and kitchen areas creates the perfect setting for both entertaining and everyday luxury living.
This listing is courtesy of: SYCHAR REALTY
INDIAN HILLS UNIT 1 REP - O6404670 - 1327 CHIPOLA TRL, MAITLAND, FL 32751 33 Days on yellowkey
$415,000 | Single Family Home 4 bedrooms, 2.0 bathroom, 2 car garage
Under contract-accepting backup offers. Discover a beautifully transformed 4-bedroom, 2-bath Maitland gem, a turnkey showpiece that blends modern style, smart upgrades, and undeniable curb appeal. The home greets you with a fresh look, mature landscaping, manicured hedges, and a custom front deck with modern horizontal railing, creating a welcoming entry and the perfect spot to enjoy your morning coffee. Step inside to an open and airy layout with abundant natural light, wood-look flooring, updated lighting fixtures, and multiple living areas ideal for both everyday living and entertaining. The renovated kitchen features white shaker cabinetry, modern countertops, stylish backsplash details, stainless steel appliances, and ample cabinet space. The dishwasher and oven were recently updated between 2022 and 2024. The kitchen flows seamlessly into the dining and living areas, creating a functional and inviting layout. The home offers spacious bedrooms along with versatile flex spaces perfect for a home office, guest room, or additional living area. The primary suite includes an updated ensuite bathroom with a glass-enclosed walk-in shower and a custom-designed primary closet with built-in organization. Out back, enjoy a fully refreshed backyard featuring brand new sod, a brand new paver patio, and a covered, screened back porch ideal for relaxing or entertaining year-round. Additional upgrades include a brand new driveway, solar panels for energy efficiency (to be paid off in full by the sellers at closing upon an accepted offer), smart home features, updated bathrooms, and modern finishes throughout. Adding to the appeal, HOA membership is optional, offering buyers the freedom of homeownership without mandatory HOA dues or restrictions. Conveniently located near shopping, dining, parks, and major roadways, this beautifully maintained Maitland home combines comfort, functionality, and contemporary style in one of Central Florida's most desirable communities.
This listing is courtesy of: ALPHA EQUITY REALTY & MANAGEMENT INC
VISCONTI EAST - O6412788 - 2401 LEGACY LAKE DR #2401, MAITLAND, FL 32751 34 Days on yellowkey
$355,000 | Condo 4 bedrooms, 2.0 bathroom, 2 car garage
All roads lead to Visconti East! Located in Maitland, bordering nearby scenic Winter Park (Park Ave./ Rollins College) this distinctive 3 story, 4 Bed/2.5 Bath townhome is situated directly off of I-4 and SR414, within 10 minutes to Downtown Orlando, Park Avenue, and close access to SR429, Winter Garden, and North Orlando. This home offers a one-of-a-kind floor plan with the entry foyer, hall closet, half bath and uniquely set up two car garage on the first floor, living room/kitchen + primary bedroom/bath on the second floor, and 3 bedrooms/ full bathroom, large hallway closet on the third level. All bedrooms feature spacious walk-in closets. Situated next to two fountain ponds that are overlooked from both sides of the unit on 2nd/3rd floors. No need to worry about additional projects, this very special and unique townhouse is move-in ready with top-quality updated features and architectural design, including imported Bianca Antico granite countertops, Italian travertine flooring and showers, stylish arches, and a massive built in bookcase. Shopping, Entertainment and Major Retail are all within miles, including downtown Maitland and Winter Park Village. Premier luxury gyms Genesis Health Club and Lifetime Fitness minutes away for ice skating, pickleball, aquatics and wellness community. Beautiful and safe bike trails accessible just by a short walk/ride. Come see all that this home and community has to offer! Call today for your private showing!
ENCLAVE/MAITLAND A-F - O6413431 - 1106 CHARMING ST, MAITLAND, FL 32751 34 Days on yellowkey
$490,000 | Townhouse 3 bedrooms, 2.5 bathroom, 2 car garage
Under contract-accepting backup offers. Welcome to this beautifully maintained lakefront townhome in a highly desirable gated community in Maitland with almost 1900 square feet of thoughtfully designed living space. This 3-bedroom, 2.5-bath residence combines comfort, functionality, and picturesque lake views. Enjoy serene views of Lake Charity from the charming front porch, formal dining room, and two upstairs bedrooms. Soaring ceilings and abundant natural light create an airy, inviting atmosphere throughout the home. The spacious open-concept kitchen overlooks the family room and features ample counter seating for barstools, generous cabinetry, and a nice pantry. A private courtyard provides a welcoming outdoor retreat and leads to the oversized 2-car garage with abundant attic storage above. The separate dining room offers a perfect setting for entertaining while enjoying tranquil lake views. A convenient guest bathroom is located on the first floor as well. Upstairs, the massive Primary suite serves as a true retreat, featuring a custom walk-in closet and a spa-inspired en-suite bath with a soaking tub, separate shower, and dual vanities. Two additional bedrooms have stunning views of the lake. One includes a Murphy bed with beautiful built-ins and a custom closet. Another full bath, and a spacious laundry room with plenty of storage complete the second floor. The reasonable HOA fee includes use of the sparkling pool, the secure gate, all landscaping, all maintenance of the exterior of this townhome including the roof, repairs, and paint, and high-speed internet with cable TV, through Spectrum. Offering exceptional space, beautiful water views, and a sought-after gated location, this townhome is the ideal place to call home. *A complimentary complete one-year Home Warranty is provided for extra peace of mind. (A recent Lender's appraisal is also available.)
KINGS ROW - O6413737 - 220 ADAMS DR, MAITLAND, FL 32751 34 Days on yellowkey
$1,995,000 | Single Family Home 4 bedrooms, 3.5 bathroom, 3 car garage
Welcome to 220 Adams Drive — a breathtaking, completely remodeled single-story masterpiece nestled in the heart of Maitland's coveted Kings Row neighborhood. Thoughtfully reimagined from the studs out with exquisite craftsmanship and elevated design, this stunning home offers 4 bedrooms, a dedicated private office, 3.5 baths, and over 3,000 square feet of refined living on a fully fenced, oversized lot. The renovation is truly comprehensive — all-new plumbing, electrical, ductwork, and three separate AC units provide complete peace of mind. Spray foam insulation delivers exceptional energy efficiency, propane gas powers the chef's kitchen cooktop and tankless hot water heater, and Lutron touch-slide dimmers indoors plus automated Lutron outdoor lighting give the home a level of sophistication and control that is rarely found at any price. French drains round out a property that has been engineered as thoughtfully as it has been finished. Step through a charming covered front porch and into a bright, open-concept interior where elevated ceilings, rich wood floors, and designer recessed lighting create an effortlessly elegant atmosphere. The chef's kitchen is a showstopper — outfitted with high-end appliances including a gas cooktop, custom white cabinetry, clever appliance garages, and bespoke built-ins that marry beauty with function. The warm and inviting living room anchors the home with a wood-burning fireplace and seamless sliding doors to the pool beyond. The split-bedroom layout offers exceptional privacy for every member of the household. The oversized primary suite features a spa-inspired en suite with a double-sink vanity, walk-in glass shower, and soaking tub — plus a large walk-in closet with custom built-ins. The second bedroom enjoys its own private en suite with a walk-in shower, perfect for guests or multi-generational living. Bedrooms three and four share a well-appointed hall bath with a tub/shower combination. Outside, your private resort awaits. The saltwater pool with sunshelf is the perfect centerpiece, framed by a covered cabana with fireplace and a fully equipped outdoor kitchen. The Lutron automated lighting system extends seamlessly to the exterior, creating effortless ambiance day and night. The fully fenced yard offers privacy and room to breathe. The property features a two-car garage and a separate one-car garage — both finished with epoxy floors. The one-car garage is currently appointed as a private home gym with an adjacent storage room, offering flexible utility from day one. Located in a quiet, tucked-away neighborhood with a community park and playground, this home is just minutes from Winter Park, Park Avenue, the Winter Park Racquet Club, and scenic parks and trails. Zoned for top-rated Dommerich Elementary, Maitland Middle, and Winter Park High School. Homes of this caliber — fully rebuilt, impeccably finished, with every system new — are extraordinarily rare. Schedule your private showing today.
This listing is courtesy of: KELLY PRICE & COMPANY LLC
PINDAR SUB - O6413652 - 200 MOSELEY AVE, MAITLAND, FL 32751 35 Days on yellowkey
$410,000 Reduced | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
Every detail of this home was thoughtfully curated to offer timeless beauty, upscale finishes, and modern functionality. This exceptional property blends contemporary design with everyday comfort, creating the perfect living experiences. The oversized walk-in shower creates a true resort-style experience with floor-to-ceiling marble-inspired tile, frameless glass enclosure, rainfall showerhead, and designer pebble stone flooring that adds texture and tranquility. Natural light pours through the window, enhancing the bright, airy atmosphere while highlighting the glossy porcelain tile floors that flow seamlessly throughout the space. lastly this home has the perfect blend of modern elegance and functionality in this beautifully designed gourmet kitchen. Featuring stunning granite countertops, sleek custom gray shaker cabinetry, and premium stainless-steel appliances, this space was crafted with both style and everyday living in mind.
PARK LAKE VILLAS CONDO - O6412094 - 1507 GROVE ST, MAITLAND, FL 32751 36 Days on yellowkey
$231,000 Reduced | Condo 3 bedrooms, 2.0 bathroom
Welcome home to this beautifully maintained 3 bedroom, 2 bath, one-story condo offering 1,256 square feet of comfortable living space in one of Central Florida's most sought-after school districts, zoned for Dommerich Elementary and Maitland Middle School. This move-in-ready home features significant recent upgrades, including a brand-new roof (2024) , new HVAC system (2024), and new Electrical panel (2026), providing peace of mind and energy efficiency for years to come. Inside, you'll find a functional floor plan with spacious living and dining areas, generous bedrooms, and abundant natural light throughout. Step outside to your large, private, fully fenced back patio, ideal for entertaining, relaxing, or enjoying outdoor living. The patio offers direct access to the community pool, making it easy to enjoy Florida's year-round sunshine. Ideally located near shopping, dining, and major roadways, this home combines low-maintenance living with top-rated schools and outstanding community amenities.
DIXIE TERRACE - O6410524 - 1741 LYNDALE BLVD, MAITLAND, FL 32751 37 Days on yellowkey
$719,990 Reduced | Single Family Home 3 bedrooms, 2.0 bathroom , 2 car carport
Charming Newly Renovated Bungalow in Prime Maitland Location – Move-In Ready with Endless Potential! Discover this beautifully updated 3-bedroom, 2-bath bungalow at 1741 Lyndale Blvd, Maitland, FL 32751 – perfectly positioned on the edge of Winter Park for an unbeatable blend of tranquility and convenience. Freshly renovated and move-in ready, this home offers immediate comfort while situated in a sought-after neighborhood where many properties are being transformed into spacious, high-end residences. It's an ideal opportunity to enjoy modern luxury today and customize further tomorrow in one of Maitland's most desirable areas. Step into a bright, open floor plan where the family room integrates effortlessly with the dining area, anchored by a cozy fireplace – perfect for gatherings. The heart of the home is the fully renovated kitchen, featuring abundant cabinetry, sleek quartz countertops, and a large kitchen island with seating for four at the breakfast bar – ideal for casual meals or entertaining. Spacious primary suite with a custom walk-in closet and sliding doors opening to the back patio and fire pit area –your private oasis for relaxing in the backyard. The en-suite primary bathroom boasts dual sinks, quartz counters, and a walk-in shower with a nice rain showerhead. Two generously sized secondary bedrooms with ample closet space, sharing a beautifully updated hall bathroom with another walk-in shower and rain showerhead. Brand-new Jeld-Wen windows, updated water and electrical systems, new tankless water heater, and new efficient central A/C system. Luxury vinyl plank flooring flows seamlessly through the entire home, delivering durability and style. Nestled in a peaceful, family-friendly neighborhood, this home offers quick access to top-rated Orange County schools, including nearby Dommerich Elementary and strong feeders to Maitland Middle and Winter Park High. Enjoy a short drive or easy stroll to Scenic Lake Lily Park, with walking trails, picnic spots, playgrounds, and charming events; Maitland's vibrant cultural scene; excellent dining options; Premier golfcourses, boutique shopping, and the upscale charm of Park Avenue in Winter Park; and convenient proximity to major Orlando attractions, themeparks, airports, and employment hubs – all while enjoying Maitland's quiet, tree-lined streets. This move-in-ready gem combines modern finishes with tremendous upside in a rapidly appreciating location. Don't miss your chance to own in one of Central Florida's most desirable pockets!
This listing is courtesy of: D & D PROPERTY MANAGEMENT SOLUTIONS LLC
TERRA PLACE - O6411881 - 766 TERRA PL, MAITLAND, FL 32751 37 Days on yellowkey
$1,149,900 | Single Family Home 4 bedrooms, 4.5 bathroom, 2 car garage
Under contract-accepting backup offers. Virtually Staged. Private Pool Retreat with Two Primary Suites in Terra Place. Nestled in Terra Place, one of Maitland’s best-kept-secret neighborhoods, where every street ends in a cul-de-sac and a community park is just steps away, this custom one-story pool home offers space, privacy, and functionality—with no mandatory HOA. Soaring cathedral ceilings, including in the kitchen, and an abundance of windows fill the home with natural light. The open-concept layout flows seamlessly between the kitchen, dining, and living spaces, making everyday living and entertaining effortless. At the center of the home, the spacious kitchen offers casual bar-top seating, stainless steel appliances including a GAS RANGE, and an abundance of storage and workspace for effortless everyday living and entertaining. The kitchen also enjoys direct views of the backyard, covered patio, and saltwater pool, offering the kind of sight lines families love and making hosting feel effortless. With TWO PRIMARY SUITES and a highly-desirable THREE-WAY SPLIT floor plan allowing for maximum privacy, EACH BEDROOM features its own ENSUITE BATH. The spacious primary retreat offers a spa-like bath experience with dual sinks, private water closet, a large shower and soaking tub under a perfectly placed window. Large-format tile and wood flooring throughout (no carpet), generous room sizes, and thoughtfully designed spaces provide a clean, timeless backdrop ready for your personal style. This north-facing property provides soft, steady natural light year-round to enjoy whether you're under the covered patio, playing with the pets in the fully fenced backyard, or posting up on the sun shelf in the saltwater pool. An oversized two-car garage with an epoxy floor and mini split AC unit, NEW ROOF (2026) and SMART HOME (All Lutron light switches/fans, smart thermostats, door locks, alarm, and cameras) features add even more value and peace of mind. Boat Parking on the right side of the home through the double gate can accommodate all of your recreational vehicles. Enjoy walking or biking to Maitland Community Park, a 25-acre wooded park with tennis courts, basketball courts, playgrounds, trails, and pavilions. Conveniently located just minutes from downtown Maitland, Park Avenue in Winter Park, downtown Orlando, major roadways, area hospitals, and both executive and international airports. Zoned for highly regarded Lake Sybelia Elementary, Maitland Middle, and Winter Park High School, this exceptional home is a rare opportunity in one of Maitland’s most secluded and desirable neighborhoods. Call today for your private showing.
This listing is courtesy of: CREEGAN GROUP
BRITTANY GARDENS - O6411521 - 2697 QUEEN MARY PL, MAITLAND, FL 32751 40 Days on yellowkey
$520,000 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
Under contract-accepting backup offers. One or more photo(s) has been virtually staged. This gem is situated in the Brittney Gardens gated neighborhood in desirable Maitland. When you enter the home you are greeted by beautiful, rich wood floors and loads of natural light. The dining room flows seamlessly into the kitchen for ease when entertaining. The kitchen boasts quartz countertops, stainless-steel appliances, ample cabinet and counter space, breakfast bar & closet pantry. The kitchen overlooks the living room, which provides glass doors, complete with retractable screens, leading to the screened-in patio. The primary bedroom is a true private retreat and is on the opposite side of the home from the secondary bedrooms. The primary retreat includes a walk-in closet with a closet system and a spa-like ensuite bathroom with a dual sink vanity. The secondary bedrooms are across the home and share a hallway bathroom. The screened-in patio overlooks a rear paver patio which provides the perfect outdoor space to enjoy the Florida lifestyle. Other amenities and updates include a whole house generator, recently repainted interior, LED lights, new carpet in all the bedrooms, and a new tankless water heater. HVAC was installed in 2024. This home is close to several restaurants and shops and is just a short distance from both the newer Maitland City Center and famed Park Avenue in Winter Park. Welcome Home!
This listing is courtesy of: KELLER WILLIAMS WINTER PARK
LAKE SYBELIA SHORES - O6411525 - 1166 N LAKE SYBELIA, MAITLAND, FL 32751 41 Days on yellowkey
$3,100,000 | Single Family Home 6 bedrooms, 4.5 bathroom, 2 car garage
Welcome to luxury lakefront living at its absolute finest in the heart of Maitland, Florida. Nestled along the pristine shores of Lake Sybelia, this extraordinary three-story estate offers an unparalleled combination of elegance, comfort, and breathtaking waterfront views. Boasting 5,355 square feet of thoughtfully designed living space, this stunning residence features six spacious bedrooms, four and a half bathrooms, and an open-concept floor plan perfectly crafted for both entertaining and everyday living. Expansive walls of glass fill the home with natural light while showcasing panoramic lake views from nearly every room. The main living area seamlessly connects the gourmet kitchen, dining room, living room, and family room, all overlooking the sparkling waters of skiable Lake Sybelia. Designed with indoor-outdoor living in mind, each floor features a balcony spanning the entire width of the rear of the home, creating multiple spaces to relax and enjoy Florida’s spectacular sunsets. Step outside to your private resort-style oasis complete with a gorgeous pool, lush landscaping, and direct lake access with your own private boat dock and lift, perfect for boating, skiing, and waterfront recreation year-round. The upstairs retreat is anchored by an impressive primary suite featuring serene lake views and private balcony access. The upper level also includes a dedicated private office, ideal for working from home while enjoying stunning lakefront views. Two additional bedrooms share a beautifully designed Jack-and-Jill bathroom, while another flexible bedroom space can easily serve as a nursery, fitness room, or additional guest bedroom. Every level of the home has been carefully designed to maximize comfort, privacy, and functionality while maintaining a sophisticated and timeless aesthetic throughout. The lower level offers endless entertainment possibilities with a spacious game room, a full movie theatre, an additional guest bedroom, and a full bathroom ideal for visitors or multi-generational living. Completing this exceptional property is a beautiful temperature controlled wine cellar holding almost 2,000 wine bottles, a two-car garage with additional storage space, a large home generator, and countless luxury details throughout. This one-of-a-kind Lake Sybelia estate delivers the perfect balance of upscale living, modern convenience, and the ultimate waterfront lifestyle in one of Central Florida’s most desirable locations.
MAITLAND WOODS - O6410813 - 1191 WILLOWBROOK TRL, MAITLAND, FL 32751 41 Days on yellowkey
$765,000 | Single Family Home 4 bedrooms, 2.0 bathroom, 2 car garage
Under contract-accepting backup offers. Don't miss this rare opportunity to purchase your dream home in the established Maitland Woods neighborhood. This charming 4-bedroom, 2-bath home has been meticulously maintained and contains premium finishes throughout. The open floor plan includes a large family/great room, dining room, and an enclosed patio, perfect for entertaining. The updated kitchen features a handmade subway tile backsplash, quartzite countertops, stainless steel appliances, a coffee bar, and a versatile indoor laundry/ second office or crafting room. The primary bathroom has been completely renovated, with a double-sink marble vanity, large shower, and walk-in closet. The second full bathroom is centrally located, with additional access to the enclosed patio, making it also an optional (future) pool bath. This home includes a large (0.29-acre) fully fenced backyard, ideal for children and/or pets to play. Some notable exterior improvements include: a new front brick patio, a new firepit area for entertaining, a vegetable/flower garden and beautiful landscaping. Maitland Woods is conveniently located near I-4, making commuting to either downtown Orlando or Lake Mary a breeze. In addition, the home is within walking distance to Orangewood Christian School, Lake Sybelia Elementary, the shops and restaurants of downtown Maitland (home of a weekly farmer’s market), city events at Lake Lily, and Lake Sybelia’s very own Homer Hough Park. Homer Hough Park is the area’s best-kept secret, with a playground, fishing, and pavilions for family events. This home will not last, call to schedule your private showing today! Age of major components includes water heater 2022; NEW front patio 2026; roof 2016; HVAC 2024/2025; Replumb CPVC 2020; inside and outside electrical panels 2025; and double-pane windows 2016-2023 – with lifetime warranty.
This listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO
DRUID HILLS ESTATES 1ST ADD - O6411336 - 1065 GREGORY DR, MAITLAND, FL 32751 41 Days on yellowkey
$519,000 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
VIDEO/VIRTUAL TOUR AVAILABLE! This Maitland pool home features 3 bed/2 bath in the main house with a 4th room addition on the other side of the garage. The 4th room has it's own separate entrance and it's own rear door access to the pool! Use it as a home office, creative studio, home gym, or income-producing suite — with no HOA to answer to. The cozy fireplace, hardwood floors, and split bedroom floor plan makes it feel like home. The oversized rectangular pool and deck were recently resurfaced and a screen enclosure was added to make maintenance a breeze. There’s still plenty of backyard space to enjoy on the huge 0.28 acre lot equipped with a white vinyl fence and storage shed. Minutes from excellent Maitland private schools and the Winter Park private school corridor, you’ll love the area! It’s close to Trader Joe’s, Winter Park Shopping & Dining, Audubon Center for Birds of Prey, Maitland Art Center, Lake Lily Park, and Enzian Theater. The RDV Sportsplex Athletic Club — with 400+ monthly classes — is an incredible convenience as well! Highway I-4 is close by and the SunRail Maitland Station is only 1 mile away, making downtown Orlando just 24 min commute on the Sunrail. Downtown Maitland is walkable with acclaimed restaurants anchored by a weekly Farmers' Market and the annual Jazz & Blues Festival. Roof is 2020, and water heater is brand new 2026. To see more of the house, WATCH THE VIDEO/VIRTUAL TOUR!
DRUID HILLS ESTATES 1ST ADD - O6411422 - 1010 GREGORY DR, MAITLAND, FL 32751 42 Days on yellowkey
$520,000 | Single Family Home 4 bedrooms, 2.0 bathroom, 2 car garage
Nestled in the heart of highly desirable Maitland, this spacious 4-bedroom, 2-bath pool home offers the perfect blend of location, functionality, and outdoor living on an oversized .28-acre lot with more than 12,000 square feet of property. Surrounded by mature trees and established neighborhoods, this prime location places you just minutes from Downtown Maitland, Historic Winter Park, Downtown Orlando, world-class shopping, dining, entertainment, and Central Florida’s renowned attractions. Maitland is loved for its charming restaurants, weekend farmer’s market, beautiful lakes, and scenic tree-lined streets, all while bordering some of the most prestigious real estate in Central Florida.The backyard is truly the showstopper of this property, featuring a sparkling open pool, beautiful vinyl fencing, and an expansive yard that is far larger than many homes in the area. Recent landscaping enhancements include a hardscaped entertaining space and decorative stone half wall, creating the perfect setting for relaxing, hosting guests, or enjoying Florida outdoor living under the shade of the beautiful oak tree.Inside, the home features a desirable split-bedroom floor plan with formal living and dining rooms, plus a spacious family room offering plenty of flexibility for everyday living and entertaining. The galley-style kitchen is equipped with granite countertops and overlooks the living areas for easy functionality. Attractive laminate wood flooring and tile flow throughout the home, while all bedrooms have been updated with new ceiling fans. Additional improvements include electrical upgrades, new exterior doors, a new roof installed in 2020, and added attic insulation for enhanced energy efficiency. Built with sturdy concrete block construction, this home offers lasting durability and peace of mind. The indoor laundry room includes the washer and dryer for added convenience. This is a rare opportunity to own a pool home with a large backyard in one of Central Florida’s most established and desirable locations.
PARK LAKE TWNHS - O6411386 - 892 PARK LAKE CIR #69, MAITLAND, FL 32751 42 Days on yellowkey
$225,000 Reduced | Townhouse 2 bedrooms, 1.5 bathroom, 1 car garage
Maitland's Hidden Gem! Discover comfort, style, and convenience in this BEAUTIFULLY MAINTAINED 2-bedroom, 1.5-bath condo in the desirable Park Lake Townhouses community of Maitland with NEW A/C 2026 and NEW Water Heater 2026. Located minutes from Park Ave, Trader Joes, Lifetime Fitness and all Winter Park/Maitland has to offer! Offering the FEEL OF A TOWNHOME with two spacious levels, a private patio, and a one-car garage, this home is tucked away in a QUIET LOCATION with PEACEFUL GREEN SPACE VIEWS from the front. Step inside to find EASY-CARE TILE FLOORING throughout the main level and a bright, welcoming Living Room filled with NATURAL LIGHT from the large front window. A convenient half bath and SPACIOUS CLOSET are located just off the hallway before the home opens into the Dining and Kitchen areas. Perfect for both everyday living and entertaining, the Dining area features sliding glass doors leading to a PRIVATE FENCED PATIO, creating a wonderful outdoor space for morning coffee, grilling, or relaxing evenings. The patio also provides direct access to the ATTACHED ONE-CAR GARAGE. Just off the Dining area, you'll find a DEDICATED LAUNDRY ROOM complete with an included washer and dryer. The beautiful Kitchen is sure to impress with its abundance of cabinetry, GRANITE COUNTERTOPS, stainless steel appliances, CHIC TILE BACKSPLASH, and center island that adds both functionality and style. Upstairs, two generously sized bedrooms provide comfortable retreats. The Primary Bedroom features ATTRACTIVE HARDWOOD FLOORING, while the second bedroom is carpeted for added comfort. Both bedrooms offer DOUBLE MIRRORED CLOSET DOORS and share a well-appointed en suite bath. FROSTED GLASS-PANELED INTERIOR DOORS throughout the home add a modern and distinctive touch. Adding even more value and peace of mind, the home features a NEW AC SYSTEM and NEW WATER HEATER. Residents of Park Lake Townhouses enjoy a SPARKLING COMMUNITY POOL along with HOA-covered trash collection, lawn care and exterior maintenance, including the roof, making for a LOW-MAINTENANCE LIFESTYLE. Ideally located, you're just minutes from the boutiques, restaurants, and cafés of PARK AVENUE IN WINTER PARK, as well as CULTURAL DESTINATIONS such as Rollins College, Morse Museum of American Art, and Winter Park Scenic Boat Tour. Nearby shopping, dining, and entertainment options abound at MAITLAND CITY CENTRE, while commuters will appreciate EASY ACCESS to I-4, SR 414, and downtown Orlando. With its STYLISH UPDATES, private outdoor space, attached garage access, and EXCEPTIONAL LOCATION near some of Central Florida's most beloved destinations, this CHARMING residence is ready to welcome you home. Act quickly—this GEM won't last long!
This listing is courtesy of: WEMERT GROUP REALTY LLC
LAKE MAITLAND TERR - O6410595 - 1140 S ORLANDO AVE #I14, MAITLAND, FL 32751 45 Days on yellowkey
$325,000 | Condo 2 bedrooms, 1.5 bathroom
One or more photo(s) has been virtually staged. Where Maitland's pristine waters meet a modern lifestyle! This luxury condominium in the coveted Lake Maitland Terrace community offers a rare blend of elegance and convenience on the shores of Lake Maitland within the famed Winter Park Chain of Lakes. Nestled among lush green spaces, this impeccably maintained mid-century modern complex boasts easy access to boutique shops, upscale dining, and vibrant entertainment. This unit stands out with its unique two-bedroom, one-and-a-half-bath layout—a rare find in the community, where most units are built with just one bath. Sunlight floods in through large windows, and warm wood floors flow throughout. This charming efficiently designed kitchen, with light cabinetry with contrasting hardware, quartz counters, and stainless steel appliances, is perfect for entertaining. Beyond the comforts of the home, enjoy the exclusive opportunity to secure a boat slip—a prized amenity in this tranquil lakeside retreat. Complex is amenity-rich with sidewalks, a community pool where residents enjoy lake access with beautiful views. The amenities include a clubhouse with a full kitchen, kayak racks, a fishing pier, and a personal storage unit. Walk to Lake Lily Park’s events, the Enzian Theater, and be just minutes from Winter Park Village and Park Avenue. Zoned for top-rated schools—Dommerich Elementary, Maitland Middle, and Winter Park High—this is a chance to embrace the best of Maitland living. Don’t miss your chance to claim this exceptional retreat as your own.
PARK LAKE VILLAS CONDO - O6410478 - 616 VILLA CIR #536, MAITLAND, FL 32751 46 Days on yellowkey
$252,000 | Condo 2 bedrooms, 2.0 bathroom
Welcome home to this beautifully updated 2-bedroom, 2-bath condo offering 1,256 square feet of comfortable living in a quiet and well-maintained Central Florida community. With major upgrades already completed, this move-in-ready home combines modern style, energy efficiency, and low-maintenance living. Step inside, from your dedicated parking spot directly in front of the unit, to discover a stunning fully remodeled kitchen. Completed in 2025 and featuring granite countertops, soft-close cabinetry and drawers, recessed lighting, and an oversized island perfect for entertaining, meal prep, or casual dining. The open living space with upgraded bamboo flooring flows seamlessly through elegant French doors to a private fenced back patio and screened-in porch, creating the perfect indoor-outdoor retreat for relaxing year-round. The spacious primary suite includes a beautifully remodeled bathroom with updated shower tile and new ceramic tile flooring, completed in 2025. Additional recent upgrades provide peace of mind and long-term value, including upgraded energy-efficient windows, added insulation, a new electric panel, and a tankless hot water heater — all completed in 2025. The AC was replaced in 2020, the roof was replaced in 2024, and the exterior was freshly repainted in 2026. Enjoy the convenience of community amenities including a pool, just steps away from your front door, and exterior maintenance handled by the property management company, allowing for truly easy Florida living. Ideally located near restaurants, shopping, and major interstates, this home offers quick and convenient access throughout Central Florida while still being tucked away in a peaceful community setting. Schedule your private showing today and experience all this upgraded condo has to provide!
This listing is courtesy of: NESTA REAL ESTATE CONSULTANTS
MAITLAND CLUB - O6410494 - 1295 BLESSING ST, MAITLAND, FL 32751 46 Days on yellowkey
$415,000 | Townhouse 3 bedrooms, 2.5 bathroom, 1 car garage
Nestled within the exclusive gated lakeside community of Montacino, this impeccably maintained Spanish/Mediterranean-inspired townhome offers refined living surrounded by serene natural beauty. The sought-after two-story Barclay model features an elegant open-concept design, seamlessly blending the spacious great room, dining area, and well-appointed kitchen—thoughtfully designed for both everyday comfort and effortless entertaining. The chef-inspired kitchen showcases rich wood cabinetry, stainless steel appliances with upgraded microwave and dishwasher. The refrigerator and oven to be replaced with Stainless steel appliances by the sellers prior to closing. Expansive windows invite in abundant natural light while framing picturesque views of the lush green space beyond. Step outside to the covered rear patio and enjoy the rare privacy and tranquility of the only Barclay unit in the community backing directly onto this beautiful preserve-like setting, enhanced by custom patio pavers added in 2024. Thoughtful updates throughout the home create a move-in-ready experience. The interior was refreshed with modern gray paint, kitchen and bathroom cabinetry were updated. The Stone countertops were updated with a beautiful Carrera style epoxy in the kitchen and baths, and the primary shower frame was refinished. Smart-home enhancements include Alexa-compatible light switches in the kitchen and primary bedroom, an upgraded alarm system, and a Ring doorbell. All three toilets have been upgraded, along with updated bathroom fixtures including shower rods and accessories. Enhancing the home’s elevated design, the entire first floor features stunning premium oversized luxury vinyl plank flooring, offering both timeless style and durability. Upstairs, the expansive primary suite serves as a peaceful retreat, complete with a generous walk-in closet and a charming private balcony overlooking the greenery beyond. The luxurious en-suite bath features dual vanities and ample room to unwind. Two additional bedrooms, a full secondary bath, and a conveniently located laundry closet complete the second level. Additional highlights include a newer HVAC system, crown molding throughout, engineered hardwood flooring across the second floor, and a one-car garage. Residents of Montacino enjoy access to a sparkling resort-style pool and the scenic beauty of Lake Charity, all while being ideally located just minutes from I-4, premier dining, shopping, and the very best of Orlando living.
MINNEHAHA SHORES - O6410033 - 109 KYLE DR, MAITLAND, FL 32751 47 Days on yellowkey
$850,000 | Single Family Home 4 bedrooms, 2.0 bathroom, 2 car garage
A tropical retreat in Minnehaha Shores with deeded lake access to the Winter Park Chain of Lakes. Tree-lined streets welcome you to this beautifully reimagined four-bedroom, two-bath split-plan home with coastal influences throughout. Formal living, dining and family spaces blend seamlessly together, creating great flexibility in layout. French doors line the back of the home and open to the covered lanai, offering effortless indoor-outdoor entertaining. This home offers an outdoor living experience that feels exceptional. Carefully curated with Florida native plants, tropical palms and ambient landscape lighting, the private backyard surrounds a beautiful pool, fountain feature, fire pit lounge and hot tub, a property that has it all. The kitchen features solid 42-inch cabinetry, stainless steel appliances, exotic granite countertops and counter seating. A beautiful porcelain sink overlooks the outdoor oasis, bringing the beauty of the outdoors inside. The primary suite is privately situated on one side of the home, while the remaining bedrooms are grouped together on the opposite side. The renovated primary bath showcases a spacious walk-in shower, designer finishes and ambient lighting. Additional improvements include a 2022 roof, updated plumbing and electrical panels, designer wallpaper throughout, engineered wood flooring in select spaces, recessed lighting, upgraded rear windows, a pool pump (2024), a repoured driveway with an additional parking pad and room for a boat or RV with 30 amp electrical, a wood-burning fireplace and much more. This neighborhood is special. Minnehaha Park sits at the entrance to the community and features tennis courts, new pickleball courts, a playground and expansive green space. Enjoy easy access to downtown Maitland and Maitland Social, which host many planned community events throughout the year. Maitland is home to renowned restaurants, The Enzian Independent Theater with Annual Film Festival and Lake Lily Park with weekly farmer’s market. Maitland offers a quintessential Florida lifestyle. Minnehaha Shores is a quiet neighborhood with no cut-through streets and enjoys access to a shared lakefront lot with a boat ramp and green space for entertaining or simply enjoying a Florida sunset. Zoned for highly regarded Orange County Public Schools, including Lake Sybelia Elementary School, Maitland Middle School and Winter Park High School, home to the globally recognized International Baccalaureate Program.
RAVNDALS REP - O6406458 - 541 MANOR RD, MAITLAND, FL 32751 48 Days on yellowkey
$1,499,000 Reduced | Single Family Home 5 bedrooms, 2.5 bathroom , 2 car carport
Under contract-accepting backup offers. Tucked between the shores of Lake Nina and Lake Maitland, this beautifully reimagined California ranch blends modern design with effortless everyday living in one of Maitland’s most desirable locations. Completely remodeled in 2022, the home showcases a fresh, sophisticated aesthetic with thoughtfully curated finishes throughout. The light-filled interior offers seamless flow between living spaces, combining clean modern lines with warm, inviting character. The renovated kitchen features a brand-new range, oven, and microwave, creating a stylish and functional centerpiece for both entertaining and daily life. Custom closets throughout the home provide elevated organization and exceptional storage. In addition to the main living areas, a spacious bonus room offers incredible flexibility and can easily function as a second family room, home office, fitness studio, playroom, or media space to fit your lifestyle needs. Step outside to a private backyard retreat designed for entertaining, complete with a sparkling pool, expansive outdoor living space, and plenty of room for gatherings, dining, and relaxing under the Florida sunshine. The indoor-outdoor flow perfectly captures the essence of California-inspired living. Ideally positioned in a picturesque pocket of Maitland between two beautiful lakes, this home also benefits from zoning for top-rated schools while offering convenient access to dining, shopping, parks, and major roadways. A rare opportunity to enjoy modern California-inspired living in an exceptional location.
STONEWOOD - O6409383 - 457 FORESTWOOD LN, MAITLAND, FL 32751 49 Days on yellowkey
$849,000 | Single Family Home 4 bedrooms, 3.0 bathroom, 2 car garage
Under contract-accepting backup offers. From the moment you step inside, you’re welcomed by a stunning double-sided fireplace and a sought-after conversation pit — the perfect setting to unwind with your favorite vinyl record, a glass of wine, and great company. Beyond the fireplace, the home opens into an expansive open-concept living space designed for both everyday comfort and effortless entertaining. The chef-inspired kitchen is the centerpiece of the home, featuring premium Forno appliances, a massive 11-foot island with seating for six, and a 6-burner Forno gas range with electric oven. Vaulted ceilings enhance the sense of space, while thoughtful details like the pot filler, apron sink, designer backsplash, and elegant cabinet hardware elevate the entire experience. Adjacent to the kitchen, the butler’s pantry offers butcher block countertops, abundant cabinetry, and a wine fridge — ideal for hosting and extra prep space. A conveniently located full guest bathroom nearby provides privacy and easy access for visitors, separate from the primary and secondary bedrooms. Situated on beautiful Lake Ruby, the outdoor living is just as impressive along with beautiful sunsets. Spend evenings around the fire pit overlooking the water, relax in the screened-in patio, or host unforgettable gatherings in the spacious backyard. A dedicated grilling patio makes outdoor entertaining easy year-round and perfect for holidays, cookouts, and waterfront living at its finest.
DOMMERICH HILLS - O6408335 - 703 NICOMA TRAIL, MAITLAND, FL 32751 49 Days on yellowkey
$735,000 Reduced | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
Located in the sought-after Dommerich neighborhood, this pool home is just a short walk to top-rated Dommerich Elementary School and Maitland Middle School. Hardwood floors and an open floor plan create an easy flow for everyday living and entertaining, centered around a spacious kitchen with gas range, breakfast bar, and abundant gathering space. The home also features a wood-burning fireplace and indoor laundry room. Significant components have been updated and include the roof (4 years), HVAC (6 years), and water heater (less than 1 year), while the electrical and plumbing systems were updated in 2010 during the home’s cosmetic renovations. Outside, the large backyard is ready for summer with a pool, heated spa, and plenty of room to entertain. A welcoming covered front porch with pavers and tongue-and-groove ceiling adds to the home’s warmth and curb appeal.