Location: Maitland , 32751
Do Not Show Listings
2462 CAROLTON RD, MAITLAND, FL 32751
$769,0005 Days on yellowkey MLS ID: O6422673
Bed: 6 Bath: 3.0 Liv Area Sq Ft: 2654 Built: 1969 Tax: $3,231 (2025)Community: English Estates Unit 3Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,231
Elementary School: English Estates Elementary
High School: Lake Howell High
Tax Year: 2025
Middle School: None
Remarks: HONEY STOP THE CAR! This Maitland POOL home has EVERYTHING you need and MORE under one roof! Welcome to one of Maitland's most desirable neighborhoods English Estates. This 6 Bedroom, 3 Bathroom estate offers over 2,600 square feet of living space with a Split Bedroom Floor Plan and a Private Pool. This home is Move-In ready and provides comfort with modern style and top of the line updates by offering the perfect combination of luxury and space which is ideal for Large Families, Multi-Generational households, and working professionals seeking a premium residence. Once you step inside, you'll find an Open Concept showcasing the Kitchen, Living Room, and Dining Room with lots of natural light down to the fine details of Wainscoting and Crown Molding. The Kitchen is the Heart of the Home and this Kitchen is surely that! Great space for the whole family to enjoy and gather around the Extra Large Island. The Kitchen comes equipped with Real Wood Cabinets, Granite Countertops, and all major Stainless Steel Appliances including a Gas Stove with Hood Vent, Dishwasher, Fridge, and Microwave. Located off the Kitchen, the Living Room opens up to the Florida Room that leads out to your own Private Pool with Screen Enclosure. The Split Bedroom Floor Plan in this home features 3 Bedrooms on each side of the home, a true even split, giving you a thoughtful layout for everyday living, entertaining, and working from home. The ROOF and AC by Trane with Nest Thermostat are all from 2021. This home comes with Natural Gas at the Stove, Tankless Water Heater, and Dryer. The Extra Long Driveway with Additional Parking on the side provides ample parking for all your vehicles, boats, RV's and toys. Residents enjoy access to A-Rated Schools and a voluntary low-cost HOA. This location is ideal and conveniently located near 1792 which is a short distance to Maitland Community Park and Maitland City Centre where there are local dining spots and recreation activities. This home is also close to Winter Park, Rollins College, AdventHealth, and 10 minutes to Downtown Orlando. Whether you're looking for more space or a new lifestyle, this home delivers! Come enjoy one of Maitland's most established sought-after neighborhoods.
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Joanna Browning (407-453-3000)
2494 CASTLEWOOD RD, MAITLAND, FL 32751
$570,00019 Days on yellowkey MLS ID: O6419597
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2482 Built: 1971 Tax: $3,375 (2025)Community: English WoodsSpa: NoSingle Family
Taxes:$3,375
Middle School: South Seminole Middle
Remarks: 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)
1000 WINDERLEY PL #141, MAITLAND, FL 32751
$300,00025 Days on yellowkey MLS ID: O6417569
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1275 Built: 1982Monthly Fee: $523 Tax: $2,725 (2025)Community: Sun Bay Club Condo Ut 1Condo
Taxes:$2,725
Elementary School: Lake Sybelia Elem
High School: Edgewater High
Middle School: Lockhart Middle
Remarks: 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)
726 FOREST GLEN CT, MAITLAND, FL 32751
$559,90015 Days on yellowkey MLS ID: O6420590
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1801 Built: 1973 Tax: $2,879 (2025)Community: Forest Brook 5Th SecSpa: NoSingle Family
Taxes:$2,879
Remarks: 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.
Listing is courtesy of: FLORIDA REALTY OF MIAMI CORP (305-598-5488)
Listing Agent: Janet Garay (786-355-7514)
2040 GERONIMO TRL, MAITLAND, FL 32751
$749,900123 Days on yellowkey MLS ID: O6390221
REDUCED by $49,100 (6.1%) on 05/11/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2375 Built: 1963 Tax: $3,301 (2025)Community: Highland Park EstsSingle Family
Taxes:$3,301
Elementary School: Dommerich Elem
High School: Winter Park High
Middle School: Maitland Middle
Remarks: Virtually Staged. Set on one of the most sought-after streets in Dommerich, this completely renovated home combines the solid construction of a 1963 block home with thoughtful modern updates throughout. From the moment you arrive, the circular driveway, classic brick accents, and welcoming front porch set the tone. Inside, a bright foyer opens to beautiful solid maple wood floors and a light, airy feel that carries throughout the home. To the right, the formal living room features built-in shelving and a striking brick wood-burning fireplace, while the adjoining formal dining room connects directly to the kitchen and can be closed off with pocket doors if you want a little separation. The eat-in kitchen is truly the heart of the home, showcasing rich solid cherry cabinetry, unique man-made glass countertops, a large farmhouse sink, and top-of-the-line stainless Bosch appliances including a built-in oven and gas cooktop. A generous peninsula overlooks the oversized family room, where French doors open to a stunning Florida room that fills the home with natural light. This space is a showstopper—large, lined with windows, and finished with soaring shiplap ceilings—creating the kind of room you’ll use year-round, with direct access to the backyard. The primary suite is spacious and refined with crown molding, a built-in closet plus a walk-in, and a beautifully renovated bath featuring matching glass countertops, a Kohler vanity, and a glass shower with both a large rain head and handheld fixture. Two additional bedrooms are generously sized and share an updated hall bath with a large vanity, classic subway tile, and a soaking tub. The interior also includes a well-equipped laundry room with cabinetry, a cedar storage closet, and access to the two-car garage. Out back, the fully fenced private yard offers plenty of room for entertainment, recently re-sodded with irrigation and enclosed with a brand new wood fence installed in 2025—leaving ample space for a future pool or patio if desired. Additional upgrades include smooth flat ceilings with recessed lighting throughout, new drywall, plantation shutters, updated windows and doors, and an energy-efficient hybrid water heater. Beyond the home itself, the location is hard to beat—just a short walk to Dommerich Elementary, Maitland Middle School, and Maitland Community Park offering tennis courts, indoor racquetball, and playgrounds. Zoned for highly regarded Winter Park High School. Call today to schedule your private showing!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Maria Van Warner (407-256-8066)
1440 LAKE SHADOW CIR #8201, MAITLAND, FL 32751
$184,90030 Days on yellowkey MLS ID: O6416664
REDUCED by $14,100 (7.1%) on 07/11/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1111 Built: 2000Monthly Fee: $532 Tax: $3,298 (2025)Community: Visconti West CondoCondo
Taxes:$3,298
Remarks: 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)
1100 S ORLANDO AVE #956, MAITLAND, FL 32751
$795,000182 Days on yellowkey MLS ID: O6367405
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1685 Built: 1973 Tax: $5,844 (2024)Community: West CoveCondo
Taxes:$5,844
Elementary School: None
Tax Year: 2024
Remarks: LAKEFRONT - Enjoy condo living at its finest from the top-floor Lake Maitland penthouse with million-dollar water and above treetop views, and beautiful panoramic sunrises from multiple rooms. This 9th-floor, 1,685 SF residence features 2 bedrooms, 2 baths, 2 multi-purpose rooms, and an open-concept kitchen, dining, and living area. Centered on the west cove of Lake Maitland, the largest of the Winter Park Chain of Lakes. The primary suite offers a spacious bath with an oversized walk-in shower and walk-in closet. The second bedroom includes guest bath access and a 6-ft soaking tub. Interior features include engineered wood flooring, plantation shutters, grand crown molding, and custom built-ins, display areas and doors. Three sets of French doors open to two balconies overlooking the lake. Balcony features electric hurricane shutters and a private 6’x5’ storage closet. A place of serenity, peace and beauty; with an energy of quiet, expansiveness and closeness to nature. Community amenities include resort-style pool and spa, boat docks, kayak racks, fitness center, clubhouse, and on-site management. Walk to Enzian Theater, Lake Lily Park, community center, library, dining, farmers market; minutes to Park Ave, Whole Foods, Winter Park Village, and major roads.
Listing is courtesy of: BECK REALTY LLC (407-256-6369)
Listing Agent: Joann Beck (407-256-6369)
1065 GREGORY DR, MAITLAND, FL 32751
$519,00046 Days on yellowkey MLS ID: O6411336
0 Days Off yellowkey (back on 7/10/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1929 Built: 1958 Tax: $5,684 (2025)Community: Druid Hills Estates 1St AddSingle Family
Taxes:$5,684
Elementary School: Lake Orienta Elementary
High School: Lyman High
Middle School: Milwee Middle
Remarks: 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!
1140 S ORLANDO AVE #F11, MAITLAND, FL 32751
$325,000129 Days on yellowkey MLS ID: O6388276
REDUCED by $24,000 (6.9%) on 07/10/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 816 Built: 1969 Tax: $3,419 (2025)Community: Lake Maitland Terrace AptsCondo
Taxes:$3,419
Remarks: This luxury condominium is in the established complex of Lake Maitland Terrace which sits on the shores of Lake Maitland, Winter Park Chain of Lakes. This immaculately maintained complex includes 11, 2-story, mid-century modern buildings sprawled across several acres, creating beautiful green space and picturesque views across the lake. This unit is special. A complete renovation with every detail accounted for, it is turnkey with enduring design. Warm wood floors are carried through spaces, kitchen has been opened to living room and flanked with windows allowing natural light to shine. Kitchen features white 42-inch shaker style cabinetry, quartz counters, subway tile backsplash, open shelving and stainless appliances. Counter seating is inviting and creates great kitchen function with loads of counter space for the aspiring chef. Primary suite is spacious with large closet storage, and renovated bath. Secondary bedroom and additional bath add to the flexibility of the unit, a guest room or home office. Indoor laundry makes this lock-and-go lifestyle even more appealing. Custom window treatments, closet system storage, updated HVAC, and fresh paint throughout. The location is pristine with walkability to the Enzian independent theatre, Lake Lily Park with a recreational trail and park, and home to community events, many restaurants and more. A short distance to Winter Park Village and Park Avenue and zoned for incredible schools with Dommerich Elementary, Maitland Middle & Winter Park Highschool. Complex is amenity-rich with sidewalks, community pool, generous dock, shuffleboards and more. Make this rare opportunity yours to own a little slice of this Maitland treasure.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Alison Mosley (407-304-6458)
1741 LYNDALE BLVD, MAITLAND, FL 32751
$719,99042 Days on yellowkey MLS ID: O6410524
REDUCED by $10,000 (1.4%) on 06/19/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1495 Built: 1943 Tax: $7,227 (2025)Community: Dixie TerraceSingle Family
Taxes:$7,227
Remarks: 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)
1010 WINDERLEY PL #149, MAITLAND, FL 32751
$429,90024 Days on yellowkey MLS ID: O6417777
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1651 Built: 1999Monthly Fee: $375 Tax: $4,525 (2025)Community: Villas Lake DestinyTownhouse
Taxes:$4,525
Remarks: 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)
1140 S ORLANDO AVE #K15, MAITLAND, FL 32751
$420,0004 Days on yellowkey MLS ID: O6423880
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 816 Built: 1966Monthly Fee: $546 Tax: $3,419 (2025)Community: Lake Maitland Terrace AptsCondo
Remarks: Welcome to Lake Maitland Terrace, where this beautifully renovated condominium offers a rare opportunity to enjoy Chain of Lakes living. Included with the property is a leased boat dock on the Winter Park Chain of Lakes, paid through 7/31/2027, with the lease transferable to the new owner and renewable. This stunning 2-bedroom, 1.5-bath residence features picturesque lake views from both bedrooms as well as the screened front porch. The screened-in front porch is the perfect place to relax while overlooking the expansive lakefront campus, complete with a sparkling pool, fishing dock, putting green, and shuffleboard courts. From the moment you step inside, you'll appreciate the exceptional quality of the modern renovation, thoughtfully designed with both style and function in mind. The beautifully updated kitchen is ideal for entertaining, featuring premium finishes, generous workspace, and a party-size ice maker. It flows seamlessly into the dining area, where abundant built-in storage provides both convenience and organization. The spacious primary suite serves as a private retreat, complete with a walk-in closet, an updated half bath, and tranquil lake views to wake up to each morning. Whether you're looking for a full-time residence or a weekend escape, this move-in-ready home offers an exceptional lifestyle in one of Winter Park's most desirable waterfront communities. This is a rare opportunity you won't want to miss.
Listing Agent: Michael Ford (407-808-3598)
51 OAKLEIGH LN, MAITLAND, FL 32751
$1,110,00089 Days on yellowkey MLS ID: O6399404
REDUCED by $25,000 (2.2%) on 07/08/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4149 Built: 1972 Tax: $5,558 (2025)Community: Oakleigh Third AddSpa: NoSingle Family
Taxes:$5,558
High School: None
Remarks: Come see 51 Oakleigh Ln, a functional residence arranged for everyday practicality. A comfortable living space features a fireplace. The kitchen includes an accent backsplash and all stainless steel appliances. The primary bedroom has a walk in closet, and its bathroom features double sinks and a separate tub and shower. Outside, a patio connects to an in ground pool within a fenced in backyard. This property is a must-see for comfort and outdoor living. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
1140 S ORLANDO AVE #H3, MAITLAND, FL 32751
$419,90025 Days on yellowkey MLS ID: O6415783
REDUCED by $20,000 (4.5%) on 07/07/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 816 Built: 1964Monthly Fee: $546 Tax: $2,530 (2025)Community: Lake Maitland Terrace AptsCondo
Taxes:$2,530
Remarks: 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)
499 JULIAN LN, MAITLAND, FL 32751
$455,00057 Days on yellowkey MLS ID: O6408583
REDUCED by $4,000 (0.9%) on 06/17/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1596 Built: 1997Monthly Fee: $79 Tax: $2,495 (2025)Community: Brittany GardensSingle Family
Taxes:$2,495
Remarks: Location, Location, Location. Welcome to your new home in Maitland! This conviently located gated community home is a charming dwelling place featuring a cozy fireplace to uplift the ambiance of your living space. The home benefits from a tasteful neutral color paint scheme throughout, providing a welcoming canvas for your interior design aspirations. The kitchen is a cook's paradise, complete with a natural gas range, a stunning accent backsplash that truly makes the room pop and new applicances. Enjoy the luxury of a generous walk-in closet in the primary bedroom, perfect for all your storage needs. The primary bathroom offers the convenience of double sinks, making morning routines smooth and efficient. The shower in the primary bathroom add an opulent touch to your personal spa-like retreat. Relax or entertain with ease with a patio for outdoor gatherings. The fenced-in backyard promises privacy for all your outdoor activities. The home benefits from a newer roof, new AC, new hot water tank, ensuring peace of mind for years to come. The appeal of the property is enhanced by fresh interior paint and fresh exterior paint to the entire home. The comfort features continue with new flooring throughout, ensuring all areas of the home are updated. Take advantage of this home's remarkable attributes and turn this dwelling place into your personal sanctuary. Some pictures virtually staged.
Listing is courtesy of: SAND DOLLAR REALTY GROUP INC (407-389-7318)
Listing Agent: Charles Munk (407-417-7709)
550 FLEMMING WAY #100, MAITLAND, FL 32751
$129,00038 Days on yellowkey MLS ID: O6412669
0 Days Off yellowkey (back on 7/9/2026)
REDUCED by $10,000 (7.2%) on 07/06/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1051 Built: 1973Monthly Fee: $448 Tax: $2,287 (2025)Community: Carrington Park A CondoCondo
Taxes:$2,287
Remarks: Under contract-accepting backup offers. 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)
2517 CAPER LN #205, MAITLAND, FL 32751
$120,000250 Days on yellowkey MLS ID: O6358434
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 550 Built: 1973 Tax: $1,789 (2025)Community: Carrington Park A CondoCondo
Taxes:$1,789
Remarks: **ATTENTION INVESTORS** Take advantage of this great opportunity and Add this income producing property to your portfolio with tenant in place. Corner unit 1 bed 1 bath condo with new laminate floors and granite countertops. This second floor unit means there is no one above you and has a pool view located steps away. The mailbox and pool are only a few steps away. Location is walking distances to Publix, Starbucks and many other stores. It is also just a 10 min drive to Full Sail University and a 30 minute drive to the parks. Best location in Orlando! Best Return available!
Listing is courtesy of: MAYOLET REALTY LLC (407-491-4893)
Listing Agent: Mayolet Bornas Moreira (407-491-4893)
873 CRANES CT, MAITLAND, FL 32751
$1,224,900105 Days on yellowkey MLS ID: O6394418
REDUCED by $25,000 (2.0%) on 06/18/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3902 Built: 1996Monthly Fee: $199 Tax: $9,081 (2025)Community: Lake Sybelia Cove Ph 01Single Family
Taxes:$9,081
Remarks: Beautifully Maintained Original-Owner Pool Home in Gated Lake Sybelia Cove. Pride of ownership shines throughout this beautifully maintained original-owner home tucked away on a quiet cul-de-sac in the gated community of Sybelia Cove. Offering 4 bedrooms, 4 bathrooms, a side-entry 3-car garage, and 3,902 square feet, this spacious residence blends timeless design with thoughtful updates in one of Maitland’s most desirable locations. Inside, soaring ceilings and expansive windows fill the home with natural light, while the family room fireplace and wood flooring throughout the main entertaining spaces adds warmth and character. The functional floor plan features a private downstairs primary suite along with a dedicated office, creating flexibility for both everyday living and working from home. Upstairs, a spacious loft is accompanied by three additional bedrooms and bathrooms. Fresh carpeting in select areas enhances comfort throughout the home. The kitchen has been updated with refreshed cabinetry, countertops, and GE Café stainless steel appliances, flowing seamlessly into the main living spaces designed for entertaining and gathering. Step outside to a screened-in pool and outdoor living area designed for year-round enjoyment while taking advantage of breezes from nearby Lake Sybelia located just behind the home. A brand-new roof (2024) provides additional peace of mind. Located just moments from downtown Maitland’s shops, dining, and parks, this home offers the privacy of gated living with exceptional walkability and convenience. Call today for your private showing.
Listing is courtesy of: CREEGAN GROUP (407-622-1111)
Listing Agent: Chris Creegan (407-622-1111)
1010 WINDERLEY PL #127, MAITLAND, FL 32751
$329,900104 Days on yellowkey MLS ID: O6395028
REDUCED by $2,600 (0.8%) on 07/09/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1563 Built: 1997Monthly Fee: $375 Tax: $4,625 (2025)Community: Villas Lake DestinyTownhouse
Taxes:$4,625
Remarks: Back on the market through no fault of the property. Recently appraised at $340,000 and inspections were completed without issue. A great opportunity for a qualified buyer seeking a smooth transaction and quick closing. Tucked into one of Maitland's most coveted lakefront enclaves, this beautifully updated townhome sits within a quietly maintained, tree-lined setting with direct access to Lake Destiny, a private community boat ramp, resort-style pool, and tennis courts, all just minutes from I-4, the 414, RDV Sportsplex, and the dining and shopping corridors of Maitland Center. First impressions set a private and secluded tone with a wrought-iron gated courtyard leads to a covered entry porch before you reach the front door. Inside, soaring vaulted ceilings and a dramatic arched transom window above the sliding glass doors flood the main level with natural light, creating an airy, open feel that far exceeds the square footage on paper. Wide-plank tile flooring runs throughout the main living areas, connecting the open living and dining spaces to a thoughtfully updated kitchen featuring white shaker cabinetry with crown accents, solid stone countertops, stainless steel appliances including a French door refrigerator and built-in microwave, pendant lighting above the breakfast bar peninsula, and a subway tile backsplash. The sliding doors open directly to a private screened patio framed by mature landscaping, creating the kind of indoor-outdoor flow that defines Florida living at its best. Upstairs, three generously sized bedrooms each offer ceiling fans, ample closet space, and brand new carpet and paint. The primary suite stands out with a 26ft footprint, two closets including a walk-in, and an ensuite bath featuring dual vanities, a full-wall vanity mirror, and a walk-in shower. Two additional bedrooms and a full bath complete the upper level, with the layout providing genuine separation and privacy between spaces. Back on the main floor, a versatile 9x9 bonus room with indoor laundry handles the day-to-day, and the full-size washer and dryer convey. The big-ticket items are handled: 30-year tile roof replaced in 2023, HVAC installed in 2020, and brushed nickel fixtures updated throughout. The one-car garage with additional driveway parking and the gated courtyard entry give this unit a sense of privacy and security rare in townhome living. Whether you are looking for a low-maintenance primary residence, a lock-and-leave second home, or a smart investment in a well-managed community with real amenities and a lakefront address, this one makes an easy case.
Listing is courtesy of: DON HARKINS REALTY LLC (321-377-0341)
Listing Agent: Donald Harkins, Iii (321-377-0341)
1783 SUNNYSIDE DR, MAITLAND, FL 32751
$849,90013 Days on yellowkey MLS ID: O6420390
0 Days Off yellowkey (back on 7/8/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2055 Built: 1986 Tax: $4,197 (2025)Community: Dixie TerraceSpa: NoSingle Family
Taxes:$4,197
Remarks: Under contract-accepting backup offers. 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.
Listing Agent: Wendy Williams Crumit (321-356-8590)
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