Location: Winter Garden
Keyword(s): West Orange High
Keyword(s) High School: West Orange High
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13527 DANIELS LANDING CIR, WINTER GARDEN, FL 34787
$335,00034 Days on yellowkey MLS ID: O6408480
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1365 Built: 2004Monthly Fee: $320 Tax: $3,745 (2025)Community: Daniels Lndg A-JTownhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,745
Elementary School: SunRidge Elementary
High School: West Orange High
Tax Year: 2025
Middle School: SunRidge Middle
Remarks: Beautiful maintained 3 bedroom 2.5 bath townhome located in the highly desirable DANIELS LANDING community in WINTER GARDEN. This property features recent mayor updates including brand new carpet. Rooms on second floor. It has a screened porch to enjoy the afternoons with family and friends. Spacious layout, ideal location and low maintenance living make this property a standout. Top rated schools. Community amenities included gated access, pool, a clubhouse, fitness center and a playground. Conveniently located near Winter Garden Villages that offers shopping and gathering opportunities for everyone needs! Close to Mayor highways Turnpike, 429 and I-4. Minutes from Disney World and many other attractions! Great as a primary home or investment opportunity. A must see today!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Julieta Kraponick (407-432-5102)
2154 OAKINGTON ST, WINTER GARDEN, FL 34787
$469,90049 Days on yellowkey MLS ID: O6402495
0 Days Off yellowkey (back on 5/15/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1585 Built: 2002Monthly Fee: $243 Tax: $5,166 (2025)Community: Stoneybrook WestSingle Family
Taxes:$5,166
Elementary School: Whispering Oak Elem
Remarks: Welcome to this beautifully maintained, single-story home that perfectly blends comfort, style, and functionality. From the moment you arrive, the manicured front yard and inviting entry to set the tone for what’s inside. Step into a bright, open living space filled with natural light from large windows. The formal living and dining area offers the perfect setting for entertaining guests or enjoying quiet evenings at home. The kitchen is updated and designed with both style and convenience in mind, featuring modern appliances, generous storage, and a breakfast bar ideal for casual meals. Just beyond, the spacious family room provides plenty of seating for gatherings, movie nights, or simply relaxing with friends and family. This home offers a desirable split floor plan with a primary suite, complete with an ensuite bathroom and a full-size soaking tub—perfect for unwinding at the end of the day. Two additional bedrooms share a well-appointed full bathroom, making it ideal for families or guests. Step outside to your own private back yard fully fenced yard features a covered, screened-in patio—perfect for enjoying Florida year-round. The home has a New Roof and A/C in 2023.
Listing is courtesy of: REAL LIVING R E SOLUTIONS (407-253-1377)
Listing Agent: Tony Marino (407-468-2004)
131 SOUTHERN PECAN CIR #201, WINTER GARDEN, FL 34787
$235,00084 Days on yellowkey MLS ID: O6393946
REDUCED by $15,000 (6.0%) on 04/14/2026
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 738 Built: 2005Monthly Fee: $309 Tax: $2,176 (2025)Community: Southern Pines CondoCondo
Taxes:$2,176
Remarks: Welcome to Southern Pines in the heart of Winter Garden. This well-maintained 1-bedroom, 1-bath upper-level condo offers a bright and functional layout with abundant natural light. The kitchen features granite countertops, ample cabinetry, and a practical layout that connects to the living and dining areas, creating a comfortable flow for everyday living. The open layout and high ceilings help maximize the space and give the unit an airy feel. The bedroom is comfortable and well-sized, offering a quiet and private retreat. This unit also includes an attached 1-car garage and additional storage, a valuable feature within the community. Southern Pines is a gated community with resort-style amenities including a pool, fitness center, tennis courts, basketball, racquetball, sand volleyball, playground, and clubhouse. The HOA covers lawn care, water, cable, and internet for added convenience. Ideally located near Winter Garden Village, Historic Downtown Winter Garden, and the West Orange Trail, with easy access to SR-429, Florida Turnpike, SR-408, and SR-50. Daily conveniences are just minutes away, including Publix (approx. 3 minutes) and Costco (approx. 8 minutes). Make this property your home today.
Listing is courtesy of: EC REAL ESTATE INVEST.& RENTAL (954-217-8649)
Listing Agent: Eloisa Armas Camacho (954-217-8649)
16077 BARKLY RIDGE CT, WINTER GARDEN, FL 34787
$2,000,00090 Days on yellowkey MLS ID: O6391901
REDUCED by $200,000 (9.1%) on 05/06/2026
Bed: 6 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 5524 Built: 2024Monthly Fee: $225 Tax: $8,585 (2025)Community: Avalon RdgSingle Family
Taxes:$8,585
Elementary School: Hamlin Elementary
Middle School: Hamlin Middle
Remarks: THE BEST OF AVALON RIDGE. FULLY UPGRADED. DESIGNER-CURATED. UNMATCHED. Welcome to one of the most exceptional residences in Avalon Ridge, a 2024-built estate that sets the standard for luxury living. Offered at $2,000,000, this is not just another home in the neighborhood, it is the benchmark: the most upgraded, most refined, and most thoughtfully designed. Spanning a grand two-story layout, this residence offers 6 bedrooms, 5 full baths, and 2 half baths, seamlessly blending modern sophistication with elevated functionality. From the moment you enter, you’re met with striking architectural presence, enhanced by custom high-end carpentry, bespoke built-ins, designer vanities, and fully customized walk-in closets; every inch curated with intention. The home is grounded by premium upgraded flooring throughout and anchored by a true gourmet kitchen, a showpiece space designed for both everyday living and elevated entertaining. Flowing effortlessly into expansive open-concept living areas, this home was built to impress and perform. The main-level primary suite is a private sanctuary, featuring a spa-inspired bath, dual vanities, and an oversized custom closet. Floor-to-ceiling sliding glass doors flood the home with natural light and open to a generous backyard, complete with approved plans for a future resort-style pool, offering the opportunity to create a true private oasis. Upstairs, the lifestyle continues with a spacious loft featuring a built-in wet bar, perfect for entertaining or unwinding. Four additional bedrooms include a well-designed Jack-and-Jill layout, while a dedicated bonus/media room provides flexibility for a theater, game room, or lounge. ADDITIONAL HIGHLIGHTS INCLUDE: Dual laundry rooms (both levels for ultimate convenience) * Two EV charging stations * Designer lighting and custom window treatments throughout * Extensive built-ins and upgraded finishes that convey. For those seeking a fully turnkey experience, select designer furnishings may be available, making this one of the most compelling move-in-ready opportunities in Winter Garden. This is more than a home, it’s the crown jewel of Avalon Ridge. A rare opportunity to own the best-renovated, best-designed, and best-presented property in the community.
Listing is courtesy of: DOUGLAS ELLIMAN (561-655-8600)
Listing Agent: Dianna Desboyaux (407-920-4601)
12513 SCARLETT SAGE CT, WINTER GARDEN, FL 34787
$875,00057 Days on yellowkey MLS ID: O6393138
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3570 Built: 2001Monthly Fee: $104 Tax: $9,264 (2025)Community: Cambridge Crossing Ph 01A 45/21Single Family
Taxes:$9,264
Elementary School: Lake Whitney Elem
Remarks: Beautifully updated home featuring an open-concept layout with soaring high ceilings and tile flooring throughout the main living areas. The bedrooms are upgraded with luxury vinyl flooring, while the spacious loft showcases elegant bamboo flooring. The gourmet kitchen is a true showpiece, equipped with premium Thermador appliances, including a built-in refrigerator, cooktop, hood, oven, and microwave. A massive cook’s island with abundant storage underneath makes this space perfect for cooking and entertaining. This home offers 5 bedrooms and 3 full bathrooms, including a stunning primary suite with a double shower head and a separate soaking tub, separate vanities. Step outside to a private outdoor patio ideal for relaxing, grilling, or enjoying Florida evenings with family and friends. Located in the highly desirable Cambridge Crossing community, this home is zoned for excellent schools, including Lake Whitney Elementary, SunRidge Middle School, and West Orange High School. The neighborhood offers a prime Winter Garden location just minutes from Winter Garden Village, downtown Winter Garden, major highways, and an abundance of shopping, dining, and entertainment options. A rare gem to find. **This property is staged.
Listing is courtesy of: KARDOSH REALTY (407-499-4466)
Listing Agent: Noah Araujo (407-728-4224)
15976 CITRUS KNOLL DR, WINTER GARDEN, FL 34787
$909,00057 Days on yellowkey MLS ID: O6399342
1 Days Off yellowkey (back on 5/13/2026)
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2953 Built: 2015Monthly Fee: $235 Tax: $11,413 (2025)Community: Hickory Hammock Ph 1DSpa: NoSingle Family
Taxes:$11,413
Remarks: Under contract-accepting backup offers. FULLY FURNISHED, HEATED POOL HOME IN A GATED COMMUNITY WITH TOP-RATED SCHOOLS AND RESORT-STYLE AMENITIES — A TRUE TURNKEY OPPORTUNITY. This stunning one-story home, located in the highly desirable gated community of Hickory Hammock in Winter Garden, is loaded with upgrades. Situated on a premium corner lot, the property features a fully fenced yard with a heated saltwater pool, travertine deck, and a versatile basketball court, all surrounded by additional green space—perfect entertaining, kids and pets. Inside, the open-concept layout centers around an oversized Silestone kitchen island, creating a seamless flow between the main living areas. The home offers a thoughtfully designed floor plan with generous living, ideal for keeping the family connected and hosting. Designer upgrades throughout include engineered hardwood flooring, crown molding, upgraded lighting, window treatments, motorized shades, and a 4-zone A/C system allowing customized temperature control across the home. Additional features include a security system, outdoor surround sound, and a termite bond for added peace of mind. This home is being sold fully furnished and truly turnkey, featuring high-quality pieces from Z-Gallerie, Pottery Barn, Sealy, Samsung, Sony, LG, GE, and Char-Broil. Residents of Hickory Hammock enjoy resort-style amenities, including a clubhouse, community pool, fitness center, tennis and volleyball courts, playgrounds, walking trails, dog park, and fishing pier. Conveniently located near Downtown Winter Garden, shopping, dining, Disney, major highways, and Orlando International Airport, and zoned for top-rated schools, this home offers the best of Central Florida living. A full list of upgrades is available in the attachments.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Mariana Cezar Ovalle (407-427-3559)
225 SOUTHERN PECAN CIR #208, WINTER GARDEN, FL 34787
$288,900106 Days on yellowkey MLS ID: O6383422
REDUCED by $1,000 (0.3%) on 05/13/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1264 Built: 2005 Tax: $3,728 (2025)Community: Southern Pines CondoCondo
Taxes:$3,728
Remarks: Beautiful 2-bedroom, 2-bathroom condo just under 1,300 sq ft in one of the most desirable areas of Winter Garden. Both bedrooms feature large walk-in closets, and the layout is exceptionally well designed, making the home feel spacious and comfortable. The unit COMES WITH A 1-CAR GARAGE, a rare and valuable feature. All appliances are BRAND NEW, including refrigerator, microwave, stove, and dishwasher. A washer and dryer are also included. The flooring has been completely renovated to elegant wood flooring throughout. The main living area offers a separate flex space that is PERFECT for a home office or a kids’ play area. Conveniently located next to the community car wash, with resort-style amenities that include an amazing clubhouse, pool area with barbecue grills, fully equipped gym, tennis courts, basketball courts, and more.
Listing is courtesy of: JOHN SILVA REALTY & ASSOCIATES (407-420-7908)
Listing Agent: John Silva (407-420-7908)
1040 MAXEY DR, WINTER GARDEN, FL 34787
$225,00089 Days on yellowkey MLS ID: O6391395
REDUCED by $25,000 (10.0%) on 05/10/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1184 Built: 1968 Tax: $1,671 (2025)Community: Bay St ParkSingle Family
Taxes:$1,671
Elementary School: Dillard Street Elem
Middle School: Lakeview Middle
Remarks: Some properties check a box. This one opens a door. This 3-bed, 2-bath home in the heart of Winter Garden is more than a place to live. It's a wealth-building opportunity sitting in plain sight. The floor plan sets up beautifully for a duplex conversion: a 1/1 in the front and a 2/1 in the back. Live in one side and let your tenant cover the mortgage, or rent both and start building cash flow from day one. At approximately 1,184 sq ft, the footprint is manageable, the concept is proven, and the location makes it work. You're minutes from historic downtown Winter Garden, major shopping corridors, top dining, and highway access. The kind of address that attracts reliable tenants and holds long-term value in one of Orange County's strongest markets. House hacking, buy-and-hold, or straight investment play. However you run the numbers, this one makes sense. ROOF is 2020, WATER HEATER 2021 and HVAC 2016
Listing Agent: Phat Nguyen (407-452-8751)
15200 LAKE CLAIRE OVERLOOK DR, WINTER GARDEN, FL 34787
$1,325,00057 Days on yellowkey MLS ID: O6401205
1 Days Off yellowkey (back on 5/10/2026)
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3904 Built: 2016Monthly Fee: $235 Tax: $8,218 (2025)Community: Hickory HammockSpa: YesSingle Family
Taxes:$8,218
Remarks: Under contract-accepting backup offers. Tucked away on a Private Street within a quiet cul-de-sac in the highly sought-after Gated community of Hickory Hammock, this exceptional 5 Bedroom, 4 Bathroom residence offers 3,908 sqft of thoughtfully designed living space with captivating views of Lake Burnett. Perfectly positioned to capture both Lake and Conservation Vistas, this home delivers the rare combination of Privacy, Comfort, and an Elevated Lifestyle in one of Winter Garden’s Most Desirable Neighborhoods. From the moment you enter, soaring 20-foot Ceilings in the foyer create a grand sense of arrival, complemented by a Formal Dining Room and immediate Sightlines to the Sparkling Pool and Tranquil Lake beyond, an unforgettable first impression that sets the tone for the entire home. Designed for both everyday living and entertaining, the first floor features Wood Plank tile throughout and an open, functional layout. The kitchen serves as the heart of the home, appointed with New Quartz Countertops, Stainless Steel Appliances, a Double Oven, abundant cabinetry, and an expansive Walk-in Pantry just off the Butler’s Pantry, complete with a JennAir Beverage and Wine Fridge. Thoughtful Lighting throughout enhances the warmth and livability of each space. Step outside to your Private Outdoor Retreat, where a Covered and Screened Lanai frames Peaceful Lake and Conservation Views. The Saltwater Pool with a Baja Shelf and Heated (electric) Spa invites year-round enjoyment, while the Spacious Backyard offers Plenty of Room for Kids or Pets to play, all while enjoying Stunning SUNSET VIEWS each evening over Lake Burnett and the Johns Lake Conservation area. A First-Floor Bedroom with a Full Bath provides flexibility for guests or multi-generational living. Upstairs, a generous Bonus Room offers endless possibilities for a media room, playroom, or additional living space. The Primary Suite is a true retreat, featuring Double Tray Ceilings and a Private Screened Balcony overlooking Lake Burnett, offering the perfect setting to take in breathtaking Sunset Views each evening. Secondary Bedrooms are well-appointed with Walk-in Closets, including one bedroom with an Ensuite Bathroom, while the remaining 2 Bedrooms share a well-designed bath. The tandem 3-Car Garage provides ample space for vehicles and storage, complemented by a spacious first-floor Laundry Room featuring New Quartz Countertops, a Sink, ample Cabinetry, and a Walk-in Closet. Residents of Hickory Hammock enjoy an impressive array of amenities including a Clubhouse, Fitness Center, Resort-style Pool, Fishing Pier, Tennis Courts, Sand Volleyball Courts, Dog Park, Playground, Walking Trails, and Golf-Cart-friendly streets. Conveniently located near Downtown Winter Garden, Winter Garden Village, major highways, Top-Rated Schools, and approximately 20 miles to Orlando International Airport. This home offers the Perfect Blend of Space, Functionality, and Desirable Water View Living - schedule your private showing TODAY.
Listing is courtesy of: CLOCK TOWER REALTY (407-832-7332)
Listing Agent: Denise Gregorie (407-463-0080)
17224 OLD COUNTRY LN, WINTER GARDEN, FL 34787
$1,999,999113 Days on yellowkey MLS ID: O6384075
REDUCED by $200,001 (9.1%) on 04/16/2026
Bed: 6 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3629 Built: 1980 Tax: $9,822 (2024)Community: Lake Avalon Groves RepSingle Family
Taxes:$9,822
Tax Year: 2024
Remarks: A rare opportunity for a completely renovated home in rural Avalon Groves and no HOA. Situated on 2.5 private acres, this beautifully remodeled farmhouse inspired estate offers peaceful country living with modern comfort and thoughtful design throughout. This spacious home features 6 bedrooms and 3.5 bathrooms and has been extensively updated within the last year. New septic tank added (now making 2 septic tanks in 2026). New roof. Tankless hot water heater. Brand new gates and fencing. The interior offers open living spaces filled with natural light, high quality finishes, and top of the line appliances throughout. Every detail has been carefully selected to create a warm and welcoming atmosphere while maintaining functionality for everyday living. The primary suite serves as a private retreat, highlighted by an expansive bathroom that is comparable in size to a bedroom. Designed for comfort and relaxation, this space offers both luxury and privacy. Outdoors, the property continues to impress with a private pool and generous acreage providing flexibility for a variety of uses. Dedicated boat and RV storage offers added convenience for those who enjoy an active lifestyle. Two separate private gated entrances provide enhanced accessibility and privacy. This property presents a rare opportunity to enjoy acreage living while still benefiting from modern updates and refined finishes in the Rural Avalon Groves area, while being only 5 minutes away from all your shopping, restaurants and groceries.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Kerstin Crow (615-428-7046)
15558 SANDFIELD LOOP, WINTER GARDEN, FL 34787
$765,00084 Days on yellowkey MLS ID: O6393987
REDUCED by $30,000 (3.8%) on 05/08/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4307 Built: 2014Monthly Fee: $114 Tax: $5,670 (2025)Community: Reserve/Carriage Pointe Ph 1Single Family
Taxes:$5,670
Remarks: One or more photo(s) has been virtually staged. Welcome to 15558 Sandfield Loop, a refreshed residence offering a turn-key lifestyle within one of Winter Garden’s most exclusive and hard-to-find GATED community. This house has been freshly updated from top to bottom, including new interior and exterior paint that makes the whole place feel brand new. The first thing you'll notice when you walk in is the massive, two-story high ceiling in the living area—it brings in tons of natural light and gives the home a great, airy feel. The kitchen has been fully redone with modern two-tone cabinets and beautiful quartz countertops. Throughout the home, you will find fresh paint and new flooring that perfectly complement the contemporary aesthetic. Situated within a highly-rated school zone, this MOVE IN READY property combines the security of a premier gated community with grand architectural features and stylish updates.
Listing is courtesy of: ORLANDO HIGHLAND REALTY LLC (561-385-7610)
Listing Agent: Xiaoli Lin (561-385-7610)
13705 GOLDEN RUSSET DR, WINTER GARDEN, FL 34787
$359,90095 Days on yellowkey MLS ID: O6390740
0 Days Off yellowkey (back on 5/7/2026)
REDUCED by $10,000 (2.7%) on 04/16/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1590 Built: 2007Monthly Fee: $333 Tax: $4,756 (2025)Community: Orchard A1-A26 B1 B2 C D1-D4Townhouse
Taxes:$4,756
Remarks: Under contract-accepting backup offers. Welcome to The Orchard, a tidy gated community of townhomes in sought-after Winter Garden. This residence blends modern comfort with low-maintenance living, offering a bright, open layout that feels inviting from the moment you step inside. Thoughtful upgrades elevate every space—stylish flooring, fresh finishes, and a contemporary color palette create a clean, move-in-ready atmosphere. The kitchen serves as the heart of the home, featuring new appliances, fine cabinetry, sleek countertops, and a functional layout ideal for everyday living. The open-concept living and dining areas flow seamlessly to a private outdoor space, perfect for morning coffee or unwinding at the end of the day. Upstairs, spacious bedrooms provide comfort and flexibility, while the primary suite offers a peaceful retreat with generous closet space and an updated en-suite bath. A dedicated laundry area and attached garage add convenience to the home’s thoughtful design. Residents of The Orchard enjoy gated security, a tranquil pool area and playground, and a prime Winter Garden location just minutes from shopping, dining, top-rated schools, and the charm of downtown Winter Garden. Tastefully updated, well-maintained, and ideally located—this townhome is the perfect blend of style and convenience.
Listing is courtesy of: LAKEFIELD REALTY GROUP LLC (407-383-6497)
Listing Agent: Drew Ross (407-383-6497)
1164 PRADO LN, WINTER GARDEN, FL 34787
$2,210,00043 Days on yellowkey MLS ID: O6403024
0 Days Off yellowkey (back on 5/6/2026)
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 4204 Built: 2026Monthly Fee: $150 Tax: $399 (2025)Community: Grove/OaklandSingle Family
Taxes:$399
Elementary School: Tildenville Elem
Remarks: Pre-Construction. To be built. Welcome to one of the most anticipated new builds at Grove at the Harvest District — the Sunburst Plan by Davila Homes, a luxury new construction masterpiece designed for those who prioritize space, style, and lifestyle. Spanning 4,204 livable square feet with 5,665 total square feet, this stunning 5-bedroom, 5.5-bath estate is thoughtfully designed from the ground up to blend elevated living with effortless entertaining. Every inch reflects Davila Homes' signature commitment to superior craftsmanship, custom finishes, and exceptional attention to detail. Step inside and discover a floor plan built for the way you actually live — an executive office for focused work, a versatile loft for flexible living, and a gracious layout that flows naturally from the heart of the home to the outdoors. The second-floor covered terrace invites year-round relaxation with a front-row view of your private retreat below, where a custom pool and fully equipped summer kitchen set the stage for unforgettable gatherings. The three-car garage rounds out a home that delivers on every level — from daily functionality to that rare feeling of arriving somewhere truly special. Located within the coveted Grove at the Harvest District, this is more than a home — it's a legacy address in one of Central Florida's new communities.
Listing is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)
Listing Agent: Alexis Anderson (561-670-5901)
143 SOUTHERN PECAN CIR #206, WINTER GARDEN, FL 34787
$279,90051 Days on yellowkey MLS ID: S5148778
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1276 Built: 2005 Tax: $3,705 (2025)Community: Southern Pines CondoCondo
Taxes:$3,705
Remarks: Stunning 2-bedroom, 2-Bath condo on the second floor, 1276 sq ft, with new carpet in the bedrooms and stairs. All Appliances updated in the last few years, and the A/C is just a little over a year old. Walk to the pool, enjoy views of the retention pond, and be close to all the community amenities. Don't miss this gem?
Listing is courtesy of: HOMESMART (407-476-0451)
Listing Agent: Maria Lloret (407-929-1994)
4230 REX DR, WINTER GARDEN, FL 34787
$2,500,000504 Days on yellowkey MLS ID: O6274608
0 Days Off yellowkey (back on 3/26/2026)
Bed: 9 Bath: 6.0 Gar: 5 Liv Area Sq Ft: 7505 Built: 2003 Tax: $16,471 (2024)Community: Lake Avalon Grvs 2Nd RepSpa: YesSingle Family
Taxes:$16,471
Remarks: Under contract-accepting backup offers. **A RARE OPPORTUNITY YOU WON’T WANT TO MISS!!** 9.75 PRIME ACRES IN THE HEART OF WINTER GARDEN ~ MAIN HOME CUSTOM BUILT BY HANNIGAN HOMES 5BD/4BA/3-CAR- 5,423 SQFT, INCLUDING AN ABOVE GARAGE APARTMENT WITH 1/BD/1/BA/+KITCHENETTE ~ SECOND HOME ON PROPERTY INCLUDES 4BD/2BA/2-CAR - 2,082SQFT ~ 10-STALL + TACKROOM HORSE BARN - 2,592 SQFT, 3 PASTURES ~ FENCED IN RIDING RING AND MUCH MORE! This countryside estate is an exclusive opportunity to own two homes, a horse barn, an adorable chicken coop, Koi pond, paver fire pit, built-in playground and so much more in the heart of the sought-after Winter Garden! Bring your horses and enjoy all that this massive CORNER LOT has to offer and being just minutes from the 429 gives you easy access to every convenience including neighboring HORIZON WEST and DISNEY THEME PARKS. Being sold all as one gives you endless opportunities in the ADDITIONAL SINGLE FAMILY HOME with the main home ready with charm for a family to make it their own. The long covered front porch welcomes you home and gives you front row seats to the riding ring. Built by Hannigan Homes, the main home was modeled after Disney’s Grand Floridian, and the thoughtful and unique features throughout are the perfect blend of comfort and quiet luxury. The roof was updated in 2019, the office space can serve as an additional bedroom, light and bright with views of the property, there is a movie/media room currently being used as an indoor trampoline park, WALK-IN WINE CELLAR for the adults, a fun HIDDEN WALK-IN PANTRY for ample kitchen storage and an energy saving SOLAR WATER HEATER. The new owner will absolutely fall in love with the PRIVATE PRIMARY SUITE that takes up the entirety of the second floor with sweeping views overlooking your estate, large WALK-IN CLOSET and well appointed ensuite bath. The additional bedrooms on the main floor give room to grow, and the additional home and garage apartment graciously allow for multi-general living. This gorgeous property is best experienced in person (stunning sunsets included!) so it can speak for itself - call today to schedule your private tour today!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
236 DONALD DR, WINTER GARDEN, FL 34787
$465,00055 Days on yellowkey MLS ID: O6401940
2 Days Off yellowkey (back on 4/30/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1080 Built: 1930 Tax: $410 (2025)Community: Showalter ParkSingle Family
Taxes:$410
Remarks: Under contract-accepting backup offers. Calling all buyers, builders, and investors, this is a rare opportunity to secure land with no HOA in the heart of Downtown Winter Garden. Located within the highly sought after Golf Cart District, just 0.5 miles from the iconic Plant Street Market, seconds from the West Orange Trail, and with convenient access to the Florida's Turnpike, this spacious quarter acre lot offers the ultimate combination of freedom, location, and connectivity. Set on a private street, this property is the perfect canvas to build your custom dream home without restrictive guidelines or additional monthly fees. With an existing structure already on site, electricity, water, and essential utilities are already in place, making the building process significantly easier, faster, and more cost effective. Whether you envision a modern custom estate, a charming bungalow, or an investment opportunity, the flexibility here is unmatched. Enjoy the ability to walk, bike, or golf cart to everything downtown has to offer, while being positioned in an area experiencing exciting growth with new dining, retail, and commercial development continuing to expand throughout Winter Garden. Opportunities like this, a no HOA quarter acre lot in the Golf Cart District with prime access and growth around it, rarely come available. This is your chance to build exactly what you have been dreaming of in one of Central Florida’s most desirable and rapidly evolving communities.
Listing is courtesy of: GLOBAL FLORIDA REALTY (407-380-3030)
Listing Agent: Lauren Bouchard (352-978-6837)
14372 SUNBRIDGE CIR, WINTER GARDEN, FL 34787
$745,000229 Days on yellowkey MLS ID: O6356579
REDUCED by $30,000 (3.9%) on 04/29/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3468 Built: 2016Monthly Fee: $166 Tax: $5,745 (2023)Community: Bradford Crk Ph IiSingle Family
Taxes:$5,745
Tax Year: 2023
Remarks: This is a unique opportunity to live in the highly sought-after gated community of Bradford Creek in Winter Garden. Impeccably maintained and lightly lived in, this waterfront oasis with no rear neighbors is a masterpiece of luxury living. Every inch of this 4-bedroom, 4 1/2-bath home reflects thoughtful upgrades and meticulous attention to detail. The innovative 3-way split bedroom plan ensures both privacy and functionality. Step into the expansive great room, complemented by a kitchen that will well exceed your expectations. Boasting wood look plank tile flooring, soft-close cabinetry, and Bosch stainless steel appliances, this culinary haven includes a massive quartz island perfect for both meal preparation and dining. Indulge in the elegant dining room adorned with a coffered ceiling, welcoming family and friends for memorable festive gatherings. The primary suite is an oversized sanctuary with coffered ceilings, custom California Closets, a luxurious newly installed Jacuzzi tub, and a rejuvenating shower. The 2nd bedroom is an oversized private bedroom suite with a full bath which is ideal for second primary bedroom, fitness room or playroom. The strategically located middle 3rd bedroom, featuring French doors, is an ideal space for a home office. The private 4th bedroom is en-suite and completes the first floor. The upstairs bonus room, complete with a powder room, offers versatility for home theater entertainment, game room or relaxation. Just a few minutes' walk to Winter Garden Village for shopping, dining and numerous events throughout the year, major commuter routes close by, walking, biking, and jogging trails. Just under a mile from downtown Historic Winter Garden, where the ever-popular Farmer's Market takes place every Saturday and of course, the well-known West Orange Trail that runs down the middle of the town. Bring your most discerning buyer – this home is a true delight that surpasses expectations!
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Julie Bettosini, Pa (321-689-9594)
64 N PARK AVE, WINTER GARDEN, FL 34787
$1,095,000114 Days on yellowkey MLS ID: O6385285
REDUCED by $54,000 (4.7%) on 04/22/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2225 Built: 2023Monthly Fee: $325 Tax: $15,104 (2025)Community: 30 North ParkTownhouse
Taxes:$15,104
Remarks: Welcome to 30 North Park, an exceptional townhome located in the heart of Historic Downtown Winter Garden — directly on the West Orange Trail and just steps from Plant Street Market, Crooked Can Brewery, local dining, shopping, and the weekly Farmer’s Market. This modern farmhouse-style residence offers four spacious bedrooms, each with a private en-suite bathroom and custom-fitted closets, providing comfort, privacy, and flexibility for guests, multigenerational living, or work-from-home needs. A first-floor bedroom serves as an ideal guest retreat, office, or flex space. The second level features an open-concept living area anchored by a designer kitchen complete with Bosch natural gas appliances, a large island, quartz countertops, farmhouse sink, artisan tile backsplash, and floor-to-ceiling windows showcasing views toward downtown and the West Orange Trail. A secondary bedroom with dramatic custom windows adds abundant natural light. On the third floor, dual primary suites offer spacious layouts, oversized windows, powered blinds, spa-inspired walk-in showers, and quartz-finished baths. Thoughtful upgrades throughout include warm wood flooring, patterned tile accents, modern black lighting fixtures, and extensive storage. Built with an STC soundproofing rating of 69, the home provides a quiet interior environment while remaining in one of Central Florida’s most vibrant walkable districts. Enjoy balcony views overlooking the trail and experience low-maintenance living with unmatched proximity to Historic Winter Garden’s amenities. Experience refined, walkable living in the heart of Winter Garden — schedule your private showing today.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Steve Healy (407-230-1441)
16669 VARONE COVE CT, WINTER GARDEN, FL 34787
$1,399,900136 Days on yellowkey MLS ID: O6375749
Bed: 7 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 5613 Built: 2016Monthly Fee: $185 Tax: $15,548 (2024)Community: TwinwatersSpa: NoSingle Family
Taxes:$15,548
Remarks: Discover Unmatched Elegance in the Coveted Twinwaters Subdivision! Welcome to your dream home, a breathtaking Winter Garden pool residence built in 2016, offering the perfect fusion of sophistication, luxury, and prime convenience. This property isn’t just a house – it’s your personal sanctuary. Grand Entrance That Stuns: Be greeted by an impressive 14-foot foyer adorned with a dazzling crystal chandelier. A beautifully crafted wooden staircase with iron balusters sets the tone for the home’s elevated style. From the moment you step inside, the open-concept layout invites you to explore spaces designed for both comfort and entertainment. Exquisite Interiors: Every detail exudes elegance. Stunning wood plank accent walls, gleaming 30-inch marble tiles, intricate tray ceilings, and granite countertops throughout create a refined yet warm atmosphere. Whether hosting friends or enjoying quiet family moments, this home is the ultimate setting. First Floor Features: Luxurious Master Suite: Tray ceiling, serene ambiance, and ample space for relaxation. Versatile Guest Suite: Ideal for guests or teens, offering privacy and comfort. Functional Spaces: A large and cozy family room, private office, formal living and dining areas, plus a service pantry with wine storage and a separate laundry room. Gourmet Kitchen: A chef’s paradise with a granite island and seating, deep basin sink, custom 50” solid wood cabinets with glass accents, glass tile backsplash, built-in oven and microwave, and a walk-in pantry. Second Floor Highlights: Expansive Upper Lounge: Large windows fill the space with natural light, making it perfect for relaxation. Bonus Room: Create your dream space—whether a music studio, movie theater, gym, or private office. Second Master Suite: Spacious and serene, with luxurious finishes. Four additional bedrooms, each offering comfort and versatility. Outdoor Oasis: Your backyard is a private paradise! A covered lanai overlooks lush landscaping, a pristine vinyl fence, and a sparkling pool. It’s the perfect retreat for relaxation or entertainment. Modern Conveniences: Solar-powered electricity for energy efficiency Whole-home water purification system Tankless water heater Crown molding throughout Tray ceilings and architectural enhancements that elevate the aesthetic Over 25k in Curtain Work Prime Location & Community Perks: Located in the sought-after Twinwaters community, enjoy access to a community pool and recreation area. Nearby, explore Winter Garden Village, Historic Downtown Winter Garden, Walt Disney World, and top-rated schools. Central Florida’s major highways, shopping, dining, and entertainment are all just minutes away. This home is truly one-of-a-kind.
Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)
Listing Agent: Tony Bardy Assis (407-796-7777)
2205 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787
$819,000125 Days on yellowkey MLS ID: O6380281
REDUCED by $30,000 (3.5%) on 04/06/2026
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3747 Built: 2000Monthly Fee: $90 Tax: $10,152 (2025)Community: Wintermere PointeSpa: NoSingle Family
Taxes:$10,152
Remarks: Welcome to beautiful Winter Garden. Check out this exceptional 5-bedroom, 3-bathroom home is located in a gated community that blends comfort with a friendly neighborhood atmosphere. Thoughtfully designed, the home features four bedrooms upstairs and a flexible downstairs bedroom ideal for guests or a home office. The spacious primary suite serves as a private escape, complete with a soaking tub, separate shower, and ample room to relax. Upstairs, two expansive loft areas provide endless possibilities—perfect for a home gym, media room, play space, or additional living area. The main level boasts formal living and dining rooms, along with a large family room that opens through sliding doors to a private pool retreat with two paved seating areas, ideal for entertaining or unwinding. An open floor plan, elegant dual-entry wooden staircase, and stainless steel appliances add to the home’s appeal. Offering generous space, charming details, and a peaceful yet convenient location, this home captures the best of Florida living—schedule your showing before it’s gone.
Listing is courtesy of: HP GLOBAL REALTY LLC (407-925-6780)
Listing Agent: Heron Patel (407-925-6780)
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