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
O6418221 - 1501 DRUID ISLE RD, MAITLAND, FL 32751 Just Added on 06/25/2026 9:21AM
$4,950 | Single Family Home | 3 beds | 2.0 baths | 2 gar
LAKESIDE LIVING in Maitland, Florida! Nestled canal front with direct access to Lake Charity, this vintage block home is built like a fortress with all the modern luxuries of today. A unique home for those who desire authenticity in both design and quality. A side entry garage leads to a courtyard like entrance with a marble path and asian influenced landscape. Double doors open into an expansive footprint with 3 large bedrooms, 2 baths and over 3,000 sq ft of living space. A 42 x 12 sunroom overlooking the water pays homage to the nostalgic Florida charm of this decade. No expense was spared when renovating this interior. Luxurious finishings and professional installation can make all the difference! Especially noted in the kitchen and baths! Upon entering, a Balsato Beige Porcelain fireplace wall anchors the space with plenty of areas to create conversational seating, a designer’s dream! The kitchen island is open to the entire living space with tons of storage and a double waterfall edge in Taj Mahal Quartzite. The perimeter counters are done in beautiful Bora Bora Quartz by Sharifstone. Real wood cabinetry in white dove compliments the earth tones giving a more transitional than modern vibe. Brushed gold hardware, lighting & plumbing fixtures are the perfect “jewelry” for the space! All new high end appliances convey. A brick fireplace graces the dining/living room wall (sounding like a song), yet another functional design opportunity to really create a home that works for YOU. There’s plenty of spots for an office, although not formally mentioned and the ability to use some of the square footage to create an additional “room” if needed. The primary suite closet takes the cake with all the fun features a dream closet should have! The ensuite bath has a lovely vanity with Quartz tops, dual sinks and a gorgeous shower with designer tile and a frameless glass door. Hardware is all in a matte black. The additional 2 bedrooms share a bath that has also had a complete remodel! This home is move in ready with a timeless style throughout. Flooring is a cohesive blend of tile and luxury vinyl plank. With ideal proximity to fine dining & shopping in Maitland, Winter Park’s infamous Park Avenue and the Theme Parks, you’ll find yourself “staycationing” a little more often! Also available to purchase.
Listing is courtesy of: LAKEFIELD REALTY GROUP LLC (407-383-6497)Listing Agent: Autumn Makin (352-455-0044)
O6419597 - 2494 CASTLEWOOD RD, MAITLAND, FL 32751 1 Day on yellowkey
$570,000 | Single Family Home | 4 beds | 2.0 baths | 2 gar
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.
Listing is courtesy of: LA ROSA REALTY CW PROPERTIES L (407-910-2168)Listing Agent: Neil Chetram (407-752-1597)
O6419531 - 551 FLEMMING WAY #201, MAITLAND, FL 32751 1 Day on yellowkey
$1,150 | Condo | 1 beds | 1.0 baths
Welcome home to this cozy and well-maintained 1-bedroom, 1-bathroom second-floor condo located in the desirable Carrington Park community. This charming unit features a spacious walk-in closet, an open and comfortable living area, and a convenient location within the community. The building is situated directly across from the laundry facility, with one of the community pools located just behind the building for easy access and enjoyment. Ideally located near Winter Park, Downtown Orlando, major highways, shopping malls, UCF, Valencia College, and Rollins College
Listing is courtesy of: PARKVIEW REAL ESTATE (407-312-6472)Listing Agent: Miranda Azer (407-312-6472)
O6419510 - 245 ORANGE PL, MAITLAND, FL 32751 1 Day on yellowkey
$675,000 | Single Family Home | 4 beds | 3.0 baths
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.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)Listing Agent: Jessica Lee (773-313-5099)
O6418917 - 1770 ALGONQUIN TRL, MAITLAND, FL 32751 3 Days on yellowkey
$3,800 | Single Family Home | 4 beds | 2.0 baths | 2 gar
Welcome to 1770 Algonquin Trail in Maitland, where modern updates meet an unbeatable location. This beautifully renovated 4-bedroom, 2-bath home offers the perfect combination of style, comfort, and convenience. Step inside to discover a stunning updated kitchen featuring solid wood cabinetry, quartz countertops, custom backsplash, and stainless steel appliances. Waterproof laminate flooring flows throughout the home, creating a clean, contemporary feel with easy maintenance. Both bathrooms have been tastefully renovated with modern finishes, while abundant natural light fills the spacious living areas. Major updates including a newer roof, updated AC system, energy-efficient dual-pane windows, updated plumbing and electrical systems provide peace of mind and energy savings. Outside, enjoy the impressive curb appeal with a paver driveway and a spacious yard perfect for relaxing, entertaining, or enjoying Florida's beautiful weather. Located in a desirable Maitland neighborhood with optional HOA and lake access, this home places you just minutes from shopping, dining, parks, major roadways, and everything Central Florida has to offer. Don't miss this opportunity to lease a move-in ready home in one of Maitland's most sought-after locations. Schedule your private showing today!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)Listing Agent: Ashley Fulford (407-580-9342)
O6418693 - 1615 KING ARTHUR CIR, MAITLAND, FL 32751 5 Days on yellowkey
$1,386,000 | Single Family Home | 4 beds | 3.0 baths | 2 gar
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......
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)Listing Agent: Dan Haber (321-624-0966)
S5152100 - 741 BROOKSIDE RD, MAITLAND, FL 32751 6 Days on yellowkey
$629,950 | Single Family Home | 4 beds | 2.0 baths | 2 gar
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.
Listing is courtesy of: TRANSCEND REALTY (407-518-7653)Listing Agent: Jacob Hara (407-933-5478)
O6417777 - 1010 WINDERLEY PL #149, MAITLAND, FL 32751 6 Days on yellowkey
$429,900 | Townhouse | 3 beds | 2.0 baths | 2 gar
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.
Listing is courtesy of: GENSTONE REALTY (407-237-0905)Listing Agent: Hafid Boujidi (407-729-3894)
O6415783 - 1140 S ORLANDO AVE #H3, MAITLAND, FL 32751 7 Days on yellowkey
$439,900 | Condo | 2 beds | 1.5 baths
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!
Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)Listing Agent: Christopher Schiffermiller, Llc (407-409-5702)
O6418229 - 195 CEDARWOOD DR, MAITLAND, FL 32751 7 Days on yellowkey
$800,000 | Single Family Home | 3 beds | 2.5 baths | 2 gar
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.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)Listing Agent: Chase Tate, Pllc (217-899-2619)
O6417569 - 1000 WINDERLEY PL #141, MAITLAND, FL 32751 7 Days on yellowkey
$300,000 | Condo | 2 beds | 2.0 baths
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!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)Listing Agent: Cece Wong (407-809-1440)
G5113516 - 1404 CARING CT, MAITLAND, FL 32751 7 Days on yellowkey
$659,900 | Single Family Home | 3 beds | 2.5 baths | 2 gar
"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!
Listing is courtesy of: ROCK SPRINGS REALTY, LLC (877-333-2811)Listing Agent: Joel Bornstein (407-252-8092)
O6409794 - 1911 BELFORD CT, MAITLAND, FL 32751 10 Days on yellowkey
$1,125,000 | Single Family Home | 4 beds | 4.0 baths | 3 gar
This elegant Mediterranean-inspired one-story residence is in the gated community of Maitland Club overlooking a tranquil pond. A well maintained 4 bedroom, 4 bath Plus home office with recent updates that include a new roof, hot water heater, pool heater, and a re-pipe. The home features a soft neutral interior palette throughout with an elegant formal living room filled with natural light featuring soaring ceilings and a dramatic wall of arched windows and French doors overlooking the outdoor living area. The dining room and home office are just off the entry foyer. The home office offers a warm workspace with hard wood flooring, custom bookcases and cabinetry. This room could be a temporary guest room it features a closet and is adjacent to the pool bath. The kitchen offers generous workspaces with extensive cabinetry, solid surface countertops, a center island, and a breakfast bar overlooking the family room. The open concept includes a planning desk and a casual dining space overlooking the pool. The spacious family room is designed for comfortable everyday living and effortless entertaining, featuring high ceilings, recessed lighting, and a fireplace framed by custom built-in audio-visual cabinetry. An oversized primary suite with a dramatic tray ceiling and expansive sitting area creates a true retreat-like atmosphere with an en-suite attached that features a large double vanity with dressing table, a relaxing garden tub and a large walk-in shower. On the opposite side of the home find three generous sized guest rooms and two full baths, laundry and hall to three car garage. The sparkling pool with tiered entry steps is surrounded by an expansive covered patio offering multiple seating and dining areas, all overlooking a lovely pond. Roof, Garage Floor and Pool heater warranties are available upon request.
Listing is courtesy of: ANNE ROGERS REALTY GROUP INC (407-649-4141)Listing Agent: Anne Rogers (407-649-4141)
O6416664 - 1440 LAKE SHADOW CIR #8201, MAITLAND, FL 32751 12 Days on yellowkey
$199,000 | Condo | 2 beds | 2.0 baths
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.
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)Listing Agent: Susan Schneider (407-461-1150)
O6416298 - 1000 WINDERLEY PL #128, MAITLAND, FL 32751 13 Days on yellowkey
$2,400 | Condo | 2 beds | 2.0 baths
Welcome to your own tropical retreat! This spacious 2-bedroom, 2-bath residence invites you in with warmth, light, and character. Rich cherry wood floors enhance the living and dining areas, while bathrooms feature elegant travertine stone finishes. The kitchen shines with granite countertops and stainless-steel appliances, while the open layout, cozy fireplace, and oversized sliding doors create the perfect balance between comfort and Florida living. Beyond your front door, discover one of the community’s best-kept secrets: a sparkling pool overlooking a serene lake, tennis courts, and lush tropical surroundings. Whether you’re enjoying your morning coffee by the water, catching a breathtaking sunset, or simply unwinding in the Adirondack chairs, every day feels like a getaway.
Listing is courtesy of: DOVER INTERNATIONAL CO., INC. (407-333-0711)Listing Agent: Roxana Barea (786-371-8691)
S5151824 - 1150 LAKE SHADOW CIR #3102, MAITLAND, FL 32751 13 Days on yellowkey
$1,700 | Apartment | 2 beds | 2.0 baths
Coming Up July 1st!!! Live the Florida Resort Life style at the Visconti Condominium. Gated community, community pool, playground, open parking. This 1st floor condo has ceramic flooring throughout, full laundry on site. Come and make this cozy condo your new home. Washer and Dryer are complementary appliances.
Listing is courtesy of: FUSION FLORIDA REALTY LLC (407-692-2590)Listing Agent: Jose Solano (407-717-5497)
O6414036 - 1781 TONTO TRL, MAITLAND, FL 32751 13 Days on yellowkey
$600,000 | Single Family Home | 4 beds | 2.0 baths | 2 gar
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.
Listing is courtesy of: EXP REALTY LLC (407-641-2808)Listing Agent: Todd Schroth, Pa (407-641-2808)
O6415928 - 255 W GEORGE AVE, MAITLAND, FL 32751 13 Days on yellowkey
$1,499,000 | Single Family Home | 5 beds | 4.0 baths | 2 gar
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.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)Listing Agent: Alison Mosley (407-304-6458)
O6414895 - 151 WHITE OAK CIR, MAITLAND, FL 32751 14 Days on yellowkey
$699,000 Reduced | Single Family Home | 4 beds | 2.5 baths | 2 gar
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!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)Listing Agent: Mary Colton (407-222-7388)
O6414837 - 2847 SHADOW VIEW CIR #2847, MAITLAND, FL 32751 14 Days on yellowkey
$210,000 | Condo | 2 beds | 2.0 baths | 2 gar
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.
Listing is courtesy of: MARKET CONNECT REALTY LLC (407-250-4708)Listing Agent: Brian Piekos (407-414-8230)
O6414213 - 830 LONGHAVEN DR, MAITLAND, FL 32751 15 Days on yellowkey
$675,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
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.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)Listing Agent: Ingrid Livingston (407-595-5972)
O6414229 - 1291 OXFORD RD, MAITLAND, FL 32751 15 Days on yellowkey
$419,000 Reduced | Single Family Home | 3 beds | 2.0 baths | 2 gar
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!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)Listing Agent: Fran Zvaigzne (407-754-8402)
O6414938 - 1149 CHARMING ST, MAITLAND, FL 32751 15 Days on yellowkey
$590,000 | Townhouse | 4 beds | 3.5 baths | 2 gar
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.
Listing is courtesy of: YOUNG REAL ESTATE (407-904-0069)Listing Agent: Ross Hudson (407-247-7288)
O6413925 - 738 LAKE HOWELL RD, MAITLAND, FL 32751 20 Days on yellowkey
$3,450 | Single Family Home | 4 beds | 2.0 baths | 2 gar
Fully furnished, beautifully maintained 4 bedroom. 2 bathroom pool home with flexible lease terms of 6 months or longer. Available July 1, 2026! Inside, you’ll find an open and inviting layout featuring no carpet throughout, making for easy maintenance and a clean, modern feel. The kitchen is equipped with stainless steel appliances, granite countertops, and ample cabinet space, perfect for everyday living and entertaining. Both bathrooms feature spacious walk-in showers, providing convenience and style. Step outside to enjoy your private backyard oasis, complete with a screened-in lanai, sparkling pool, and fully fenced backyard, ideal for relaxing, entertaining, or enjoying Florida living year-round. Lease terms are negotiable with a minimum 6-month commitment. Don’t miss this opportunity to make this beautiful pool home your next residence!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)Listing Agent: Kevin Asenjo (407-844-5252)
O6412669 - 550 FLEMMING WAY #100, MAITLAND, FL 32751 20 Days on yellowkey
$139,000 | Condo | 2 beds | 1.0 baths
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!
Listing is courtesy of: LOKATION (954-545-5583)Listing Agent: Brandy Ray (949-449-5652)
S5151303 - 2155 FENNELL ST, MAITLAND, FL 32751 20 Days on yellowkey
$489,900 | Single Family Home | 3 beds | 2.0 baths | 2 gar
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.
Listing is courtesy of: TCA REALTY, LLC (407-507-3982)Listing Agent: Deidre Rios (407-433-6238)
O6413768 - 1440 LAKE SHADOW CIR #8304, MAITLAND, FL 32751 20 Days on yellowkey
$1,550 | Condo | 2 beds | 2.0 baths
Beautiful 2-bedroom, 2-bathroom condo located in the highly sought-after, gated community of Visconti in Maitland. This bright and airy floor plan offers an exceptionally open layout designed to maximize natural light throughout. The kitchen overlooks a spacious living and dining area, creating a seamless flow that is perfect for both everyday living and entertaining. Step outside to your private balcony with additional storage, ideal for relaxing and enjoying the Florida lifestyle. Vaulted ceilings enhance the sense of space, adding to the home’s open and inviting feel. Residents of Visconti enjoy resort-style living with an impressive list of amenities, including: -Resort-style pool overlooking Lake Shadow -Wi-Fi access at the pool deck -Gated community with controlled access -Car wash area -On-site laundry facilities -Clubhouse -Fully equipped fitness center -Playground and more Experience the perfect blend of comfort, convenience, and lifestyle in one of Maitland’s most desirable communities. Pets Not Allowed! HOA Approval is required prior to move-in $100.00 HOA Application Fee each person HOA processing time is 30 days Tenant Liability Insurance **Required**
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)Listing Agent: Carissa Lawhun (407-207-2220)
O6413200 - 908 VERSAILLES CIR, MAITLAND, FL 32751 20 Days on yellowkey
$899,000 | Single Family Home | 4 beds | 2.0 baths | 2 gar
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.
O6414097 - 206 MOSELEY AVE, MAITLAND, FL 32751 20 Days on yellowkey
$449,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
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.
Listing is courtesy of: SYCHAR REALTY (407-921-0069)Listing Agent: Brianna Grant (407-764-8436)
O6414135 - 2640 LEGACY VILLAS DR, MAITLAND, FL 32751 20 Days on yellowkey
$1,845 | Condo | 2 beds | 2.0 baths | 2 gar
2/2, 2 Car Garage, Three Story Condominium, Living Room, Dining Room, Kitchen Appliances Included: Stove, Refrigerator, Disposal, Microwave and Dishwasher, Bonus Room, Inside Closet Utility Room with Washer and Dryer Hookups, Walk in Closets, Carpet and Tile Throughout Home, Gated Community with Community Pool, Clubhouse, Fitness Center, Playground, BBQ Grills, Pest Control Included by HOA, Pets Ok, NO SMOKING, Year Built: 2000/ 1280 Sqft.
Listing is courtesy of: LEGENDS REALTY (407-333-1010)Listing Agent: Tina Lopez (407-333-1010)
O6404670 - 1327 CHIPOLA TRL, MAITLAND, FL 32751 20 Days on yellowkey
$415,000 | Single Family Home | 4 beds | 2.0 baths | 2 gar
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.
Listing is courtesy of: ALPHA EQUITY REALTY & MANAGEMENT INC (407-789-1002)Listing Agent: Abbas Sultanali (407-435-9596)
O6414075 - 361 W LAKE FAITH DR #112, MAITLAND, FL 32751 21 Days on yellowkey
$2,400 | Condo | 3 beds | 2.0 baths | 1 car
Fabulous Lake Front, 3 bedroom, 2 bath condo beautifully renovated. Relax in the spacious great room or sit out on the large screen porch and enjoy the peace and quiet, looking over serene Lake Faith; or grab your canoe, kayak, and paddle board to be on the water. Awesome kitchen with stainless appliances, quartz tops, wood tile floors throughout, Dining room opens to 2nd balcony, great for cross breezes. Over 1700 sq ft, large bedrooms and walk-in closets/storage spaces and indoor laundry, all new baths with custom tile, custom painted doors and upgraded light fixtures throughout. Condo also has 1 covered Carport space with attached 5x5 storage closet. Tucked into Fabulous Maitland, this complex offers a private, tranquil atmosphere with terrific amenities including a gated entrance, clubhouse, and pool. And the location couldn’t be more convenient, with easy access to I-4 as well as a new retail and restaurant development within a short stroll. Come enjoy the beautiful Lake front lifestyle Lake Faith has to offer. Rare rental!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)Listing Agent: Theresa Kincaid (407-310-0339)
O6412788 - 2401 LEGACY LAKE DR #2401, MAITLAND, FL 32751 21 Days on yellowkey
$355,000 | Condo | 4 beds | 2.0 baths | 2 gar
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!
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)Listing Agent: Trace Christian, Iii (407-202-8135)
O6413431 - 1106 CHARMING ST, MAITLAND, FL 32751 21 Days on yellowkey
$490,000 | Townhouse | 3 beds | 2.5 baths | 2 gar
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.)
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)Listing Agent: Donna Bryant (407-509-8047)
O6413737 - 220 ADAMS DR, MAITLAND, FL 32751 21 Days on yellowkey
$1,995,000 | Single Family Home | 4 beds | 3.5 baths | 3 gar
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.
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)Listing Agent: Kelly Price (407-645-4321)
O6413581 - 1000 S ORLANDO AVE #A31, MAITLAND, FL 32751 21 Days on yellowkey
$300,000 | Condo | 2 beds | 2.0 baths | 1 car
Experience the best of lakeside living in this beautifully updated third-floor corner residence with panoramic views of Lake Maitland. Perfectly positioned along Orlando Avenue and adjacent to Fort Maitland boat ramp, the home combines convenience with a truly unique lifestyle just minutes from Winter Park’s shopping, dining, and cultural attractions. Inside, you’ll find luxury vinyl plank flooring throughout and a stunning kitchen designed for modern living, showcasing quartz countertops, sleek stainless steel appliances, custom cabinetry, and stylish finishes that create an inviting atmosphere for both cooking and entertaining. The spacious primary suite is highlighted by a custom-designed closet for optimal storage and comfort. Enjoy community amenities that make every day feel like a retreat, including a pool overlooking the lake and access to boat slips (via waitlist) on the highly coveted Winter Park Chain of Lakes. Whether you’re seeking a serene escape or a vibrant, connected lifestyle, this condo delivers the rare combination of location, water views, and thoughtful updates in one of Central Florida’s most desirable areas.
O6413652 - 200 MOSELEY AVE, MAITLAND, FL 32751 22 Days on yellowkey
$420,000 Reduced | Single Family Home | 3 beds | 2.0 baths | 2 gar
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.
S5151186 - 2075 HOWELL BRANCH RD #101, MAITLAND, FL 32751 22 Days on yellowkey
$1,450 Reduced | Condo | 2 beds | 1.0 baths
***Move-In Special! Sign a lease by July 15 and receive 25% OFF your second full month's rent!*** Available Now! This charming 2-bedroom, 1-bathroom end unit in Maitland is perfectly situated within walking distance to grocery stores, restaurants, and shopping—and just minutes from Downtown Winter Park, Full Sail University, Rollins College, Advent Health Winter Park, and so much more! This property is walkable to everyday conveniences, & quick access to major highways for easy commuting. Water, trash, and sewer are included in the rent—one less bill to worry about and no HOA approval required! No Pets. Contact us to schedule your showing today!
Listing is courtesy of: CENTRAL FLORIDA REALTY MANAGEMENT LLC (407-542-4403)Listing Agent: Kevan Patel (407-491-3559)
O6411330 - 916 ROBINHOOD CT, MAITLAND, FL 32751 22 Days on yellowkey
$2,199 Reduced | Half Duplex | 3 beds | 1.5 baths | 1 gar
Welcome home! This 3-bedroom, 1.5-bath DUPLEX is available for June 10th 2026. Includes a fenced-in backyard. Located conveniently in the desirable City of Maitland, this property is close to the shopping district, Hospital district, Winter Park shopping, and I-4. This property features a comfortable layout with well-apportioned bedrooms and bathrooms. Washer and dryer included. Act now! This one won’t last long! Pets over 50 pounds will be considered on a case-by-case basis. All applicants are required to do a credit and background check. Renters insurance is required. All residents are automatically enrolled in a master renters insurance policy for $11.95 per month. Residents can opt out of the master policy by providing proof of their own policy that meets minimum requirements.
Listing is courtesy of: 407 PROPERTIES (407-545-2594)Listing Agent: Steven Simpson (407-545-2594)
O6411314 - 914 ROBINHOOD CT, MAITLAND, FL 32751 22 Days on yellowkey
$2,049 Reduced | Half Duplex | 2 beds | 1.0 baths | 1 gar
Welcome home! This 2-bedroom, 1-bath DUPLEX is available for Jun 9th 2026. This property has been renovated from top to bottom and includes a new fenced-in backyard. Located conveniently in the desirable City of Maitland, this property is close to the shopping district, Hospital district, Winter Park shopping, and I-4. This property features a comfortable layout with well-apportioned bedrooms and bathrooms, a brand-new kitchen with lots of counter and cabinet space, and new appliances. Washer and dryer included. Act now! This one won’t last long! Pets over 50 pounds will be considered on a case-by-case basis. All applicants are required to do a credit and background check. Renters insurance is required. All residents are automatically enrolled in a master renters insurance policy for $11.95 per month. Residents can opt out of the master policy by providing proof of their own policy that meets minimum requirements.
O6412985 - 1507 LEGACY CLUB DR #1507, MAITLAND, FL 32751 23 Days on yellowkey
$1,495 | Condo | 1 beds | 1.0 baths | 1 gar
Exceptional 1 bedroom Town Home in resort style community of Visconti. This 3 level unit features an oversized 1 car garage, open living / dining room combo with laminate flooring & tile, a gourmet kitchen, large bedroom and stunning bathroom ! Community offers its residents a tropical pool, fitness, basket ball - tennis court, lake with dock and gorgeous club house. Best of all - water, sewer & trash removal is included in rent ! Available now. Call today !
Listing is courtesy of: KUNERT REALTY INC (407-745-0949)Listing Agent: Andreas Kunert (407-467-1830)
O6412922 - 1175 LAKE SHADOW CIR #4208, MAITLAND, FL 32751 23 Days on yellowkey
$2,350 | Condo | 4 beds | 2.0 baths
Stunning - fully remodeled 4 bed waterfront condo in resort style community of Visconti.Condo features all new vinyl plank flooring throughout, designer paint, a gourmet kitchen with brand new espresso cabinets, granite counters and stainless steel appliances.New bathrooms with custom tile, vanities and light fixtures. Screened in patio with outside storage overlooking the pond. Community offers its residents 2 swimming pools, gym, tennis - and basket ball court. Located within minutes to shopping, entertainment and Interstate 4. Call and schedule your viewing today !
O6410524 - 1741 LYNDALE BLVD, MAITLAND, FL 32751 24 Days on yellowkey
$719,990 Reduced | Single Family Home | 3 beds | 2.0 baths | 2 car
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!
Listing is courtesy of: D & D PROPERTY MANAGEMENT SOLUTIONS LLC (407-434-1693)Listing Agent: Allan Dion (407-434-1693)
O6411881 - 766 TERRA PL, MAITLAND, FL 32751 24 Days on yellowkey
$1,149,900 | Single Family Home | 4 beds | 4.5 baths | 2 gar
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.
Listing is courtesy of: CREEGAN GROUP (407-622-1111)Listing Agent: Chris Creegan (407-622-1111)
O6409154 - 245 ORANGE PL, MAITLAND, FL 32751 27 Days on yellowkey
$675,000 | Apartment | 3 beds
Location, location!! Discover a rare opportunity to own an income-producing triplex in the heart of Maitland, just steps from the iconic Enzian Theater and vibrant Downtown Maitland. 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 triplex features three separately units, each with its own separate electric meter and IN-UNIT washer and dryer - a highly sought-after feature for both tenants and owner-occupants alike. This property also has ample parking and an oversized storage shed. Unit 1 is a 2 Bed/1 Bath unit 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. Opportunities to own a triplex in such an unbeatable location rarely come to market.
O6411521 - 2697 QUEEN MARY PL, MAITLAND, FL 32751 27 Days on yellowkey
$520,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
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!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)Listing Agent: Beth Logullo (772-633-0670)
O6411525 - 1166 N LAKE SYBELIA, MAITLAND, FL 32751 28 Days on yellowkey
$3,100,000 | Single Family Home | 6 beds | 4.5 baths | 2 gar
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.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)Listing Agent: Joseph Sipp (407-820-7016)
O6410813 - 1191 WILLOWBROOK TRL, MAITLAND, FL 32751 28 Days on yellowkey
$765,000 | Single Family Home | 4 beds | 2.0 baths | 2 gar
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.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)Listing Agent: Marti Hornell (407-222-1443)
O6411336 - 1065 GREGORY DR, MAITLAND, FL 32751 28 Days on yellowkey
$519,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
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!
O6411069 - 341 CHERRYWOOD GARDENS DR #2, MAITLAND, FL 32751 28 Days on yellowkey
$185,000 | Condo | 2 beds | 2.0 baths
Under contract-accepting backup offers. Looking for an investment with passive income? This may be the answer to your goal! A 2-Bedroom, 2-Full Bath with tenants in place is ready for steal at Cherrywood Gardens! A quiet, small, and well- maintained community tucked in the heart of Maitland where most tenants stay long-term due to its strategic location and great features. Unit 341 has its own 2 reserved parking space right in front, plus available guests parking. This cozy unit with a covered front porch has its own closet laundry, a sliding door at the back end allowing natural lights indoor and overviewing the courtyard. The unit is beautifully maintained with updates: cabinets, countertops, lights and tile floorings. The community is also surrounded with mature trees and pathways on the sides of units with a small pool the occupants can enjoy. And, of course guests parking slots are also available.This is truly an investor’s dream. Tenants renewed for another year until January 31, 2027. The occupancy rate is very high at Cherrywood Gardens according to the Property Manager. Come and view the property before it’s gone in the market!
Listing is courtesy of: SPHERA REALTY LLC (951-454-6812)Listing Agent: Aurora Millado (951-454-6812)