Location: Winter Garden
Keyword(s): West Orange High
Keyword(s) High School: West Orange High
Do Not Show Listings
330 SOUTHERN PECAN CIR #208, WINTER GARDEN, FL 34787
$298,000249 Days on yellowkey MLS ID: S5136841
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1453 Built: 2005Monthly Fee: $520 Tax: $3,625 (2024)Community: Southern Pines CondoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,625
Elementary School: SunRidge Elementary
High School: West Orange High
Tax Year: 2024
Middle School: SunRidge Middle
Remarks: Welcome to this amazing unit, nestled within the gated community of Southern Pines in the sought after area of Winter Garden , Florida; this beautiful 3 bedrooms 2 bathrooms condo is located in the second floor and has an open concept kitchen with a Dinning- living combo area, also an additional space for an office or a play area , the unit also has a split bedroom plan , with a spacious primary bedroom and an ensuite, also two additional bedroom at the other side of the unit, with an additional full bathroom . This incredible community has a so much in amenities; a real lifestyle for the residents , such as community pool and spa , a very well equipped fitness center, a club house with many areas for family entertainment, tennis court, playground, a car wash area and an indoor basketball / racquetball court. This condominium is located a short drive from the Winter Garden Village shopping area , as well as Downtown Winter garden, with easy access to all main Highways making the commute easier. The Disney World parks are just 9 miles away; this community is definitely a place where families will experience great enjoyment; don't miss the chance to call this unit your NEW HOME!!
Listing is courtesy of: HOME WISE REALTY GROUP, INC. (407-712-2000)
Listing Agent: Libia Rodriguez (407-952-7069)
13212 SOCIAL LN, WINTER GARDEN, FL 34787
$595,00068 Days on yellowkey MLS ID: O6398708
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2526 Built: 2005Monthly Fee: $100 Tax: $4,474 (2025)Community: Regency Oaks FSpa: NoSingle Family
Taxes:$4,474
Tax Year: 2025
Remarks: One or more photo(s) has been virtually staged. SEVERAL PHOTOS HAVE BEEN VIRTUALLY STAGED !Welcome to this beautifully updated 4-bedroom, 2.5-bath home in the highly sought-after Regency Oaks community. Thoughtfully upgraded for long-term peace of mind, this residence features a newly replaced roof, a 2023 HVAC system (both indoor and outdoor units), and a 2023 water heater—major improvements that add exceptional value and confidence for the next owner. Step inside to discover a bright, open floor plan with luxury vinyl flooring throughout, offering durability, modern style, and easy maintenance. The remodeled kitchen showcases sleek modern cabinetry and quartz countertops, creating a fresh, contemporary space perfect for everyday living and entertaining. The spacious primary suite provides a comfortable retreat, complemented by three additional bedrooms ideal for family, guests, or a home office. With two full bathrooms and a convenient half bath, the layout is designed for both functionality and comfort. Enjoy Florida living at its best with a screen-enclosed patio and a fully paved backyard, offering a low-maintenance outdoor oasis perfect for gatherings, grilling, or quiet relaxation. Located just 15 minutes from Universal Studios and Disney Parks and less than a 2-minute walk to AdventHealth, this home is perfectly positioned for both families and professionals. Regency Oaks offers resort-style amenities including a sparkling pool, clubhouse, tennis courts, playground, and a scenic park—enhancing the lifestyle experience beyond your front door. This move-in-ready home combines modern upgrades, unbeatable convenience, and exceptional community features—an outstanding opportunity to enjoy the best of Winter Garden and Orlando living.
Listing is courtesy of: PMI PRIME HOME (407-218-7598)
Listing Agent: Jianlin Shi (407-988-5057)
17422 CHANNEL WAY, WINTER GARDEN, FL 34787
$767,000119 Days on yellowkey MLS ID: G5108709
1 Days Off yellowkey (back on 6/8/2026)
REDUCED by $7,000 (0.9%) on 05/11/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3261 Built: 2019Monthly Fee: $215 Tax: $9,958 (2025)Community: Waterside On Johns LakeSpa: NoSingle Family
Taxes:$9,958
Elementary School: Hamlin Elementary
Middle School: Hamlin Middle
Remarks: Welcome to this beautifully maintained 5-bedroom, 3-bathroom home offering comfort, space, and versatility for modern living. With a thoughtfully designed floor plan, this home is perfect for families, multigenerational living, or anyone needing extra space for a home office or guest rooms. The open living areas are filled with natural light and provide a welcoming atmosphere for both everyday living and entertaining. The kitchen offers ample cabinetry and counter space, flowing seamlessly into the dining and living areas, ideal for gatherings and family meals. The primary suite features a private bathroom and generous closet space, creating a relaxing retreat. Additional bedrooms are well-sized and flexible, perfect for children, guests, or work-from-home needs. Three full bathrooms ensure comfort and convenience for everyone. Outside, enjoy a private backyard with plenty of room for outdoor entertaining, play, or relaxation. Whether you envision weekend barbecues, a garden, or a peaceful outdoor escape, this space delivers. Conveniently located near schools, shopping, dining, and major roadways, this home combines space, comfort, and location, ready for its next owner to make it their own. Serious buyers welcome. Schedule a showing today!
Listing is courtesy of: LIST NOW REALTY, LLC (352-385-7636)
Listing Agent: Matt Buttner (352-385-7636)
483 PENNSYLVANIA AVE, WINTER GARDEN, FL 34787
$339,90070 Days on yellowkey MLS ID: O6398208
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1008 Built: 1988 Tax: $2,702 (2025)Community: East Garden Manor Add 03Single Family
Taxes:$2,702
Elementary School: Maxey Elem
Middle School: Lakeview Middle
Remarks: Move in ready, completed renovated, property offers two bedrooms and 2 bathrooms, brand new bathrooms, brand new kitchen, new appliances, new windows, ceramic trough the house, new roff, new pluming, close to major roads, schools, minutes to Winter Garden dawn town.
Listing is courtesy of: STIRLING INTERNATIONAL REAL ES (407-250-1000)
Listing Agent: Rosa Rodriguez (407-832-1185)
205 SURPRISE DR, WINTER GARDEN, FL 34787
$1,200,000201 Days on yellowkey MLS ID: O6365188
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2171 Built: 1950 Tax: $3,406 (2024)Community: Winter Garden Shores RepSingle Family
Taxes:$3,406
Elementary School: Dillard Street Elem
Remarks: PRICE ADJUSTED to reflect recent appraisal, this four-lot parcel presents immediate value- with two vacant lots ready for expansion, additional income potential, or future development. Discover an exceptional property in the heart of highly desirable GOLF CART DISTRICT of Winter Garden. Situated on an expansive four-lot parcel totaling 3/4 of an acre, this unique estate offers unmatched space, charm and potential with NO HOA- all within short distance to the 22 mile long West Orange Trail, Winter Garden Farms Market, Plant Street dining, shopping and breathtaking sunsets over Lake Apopka. This beautifully maintained three-bedroom, two-bath home features an office with custom wood built-ins and a light-filled breezeway framed in windows, perfect for a sunroom or additional living space. Gorgeous hardwood floors flow throughout, and the newly renovated bathroom showcases modern, floor-to-ceiling tile for a luxurious touch. Storage is abundant, including an oversized two-car garage with a half bath, ideal for hobbyist or future conversion opportunities. Outside, the property transforms into a private oasis featuring a sparkling heated saltwater pool, outdoor fireplace and lush mature landscaping complete with fruit trees - all fully fenced for privacy. Two of the four lots are currently vacant, offering potential to subdivide, expand, or build. A large shed, rated as a detached garage, on the property provides additional space for a workshop or equipment storage. There is ample room for all your recreational toys; golf-cart, boat, and more. The current owners also have plans for a kitchen renovation and poolside wraparound porch, which they are willing to share with the buyer - opening the door to greater customization. Whether you're seeking a serene retreat, developmental potential, or the charm of downtown Winter Garden living, this property is truly one of a kind. This private paradise location is a convenient commute to Downtown Orlando, Disney and other Orlando attractions. You're dream estate awaits.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Alison Scorsone (321-689-3554)
914 TROWMAN ALY, WINTER GARDEN, FL 34787
$649,00028 Days on yellowkey MLS ID: O6410871
REDUCED by $26,000 (3.9%) on 06/02/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1642 Built: 2022Monthly Fee: $356 Tax: $6,421 (2025)Community: Oakland ParkSingle Family
Taxes:$6,421
Elementary School: Tildenville Elem
Remarks: One or more photo(s) has been virtually staged. Nestled in the highly sought-after Oakland Park community, this beautifully maintained 3-bedroom, 3-bath home is the definition of move-in ready living. Featuring desirable upgrades throughout, including gas appliances, elegant plantation shutters, and a turnkey design, this home offers the perfect blend of comfort, style, and convenience. Enjoy open-concept living spaces filled with natural light, spacious bedrooms, and a layout designed for modern living and entertaining. Pride of ownership shines in every detail, making this home truly stand out. Located in a charming golf cart community with resort-style amenities, residents enjoy access to parks, schools, walking trails, and more. Just minutes from vibrant Downtown Winter Garden, you'll love being close to the award-winning farmers market, lively festivals, boutique shopping, dining, and entertainment. This is your opportunity to own a well-maintained, upgraded home in one of Winter Garden's most desirable communities!
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
940 MARSH REED DR, WINTER GARDEN, FL 34787
$779,99071 Days on yellowkey MLS ID: O6397274
REDUCED by $20,000 (2.5%) on 05/13/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3493 Built: 2015Monthly Fee: $128 Tax: $10,543 (2025)Community: Johns Lake PointeSpa: NoSingle Family
Taxes:$10,543
Remarks: One or more photo(s) has been virtually staged. Welcome to 940 Marsh Reed Drive, a beautifully upgraded 5 bedroom, 3 bathroom, SOLAR HEATED POOL HOME offering just under 3,500 square feet of well-designed living space in the highly sought-after Johns Lake Pointe community! Additional OFFICE and LOFT / BONUS ROOM. Solar panels are paid off! From the moment you arrive, the home makes a strong impression with its tile roof, enhanced landscaping, and well manicured appearance, setting the tone for what’s inside. The interior opens to a bright, expansive layout with high ceilings, neutral finishes, and multiple living and dining areas designed for both everyday comfort and entertaining. The heart of the home is the open-concept kitchen, featuring abundant cabinetry, walk-in pantry, granite countertops, stainless steel appliances, extended butler's pantry style prep area, and a large center island that flows seamlessly into the main living area. Natural light fills the space, creating an inviting atmosphere that connects effortlessly to the indoor and outdoor living areas. The first floor dedicated office provides the ideal work-from-home setup or can easily function as a flex space to suit your needs. Upstairs, a spacious loft/bonus area offers additional versatility—perfect for a media room, playroom, or secondary living space. The primary suite is generously sized and features tray ceilings, large windows, and a relaxing, private feel. The en-suite bathroom includes dual vanities, a walk-in shower, walk-in closet, and ample storage, creating a comfortable retreat at the end of the day. Step outside to your private backyard oasis, where the SCREENED-IN POOL and covered lanai deliver the ultimate Florida lifestyle. The pool is equipped with SOLAR HEATING for year-round enjoyment and a NEW POOL PUMP for efficiency. A standout feature is the $7,000 integrated smart exterior lighting system, including the pool enclosure, creating a stunning nighttime ambiance perfect for entertaining. Additional upgrades include a new gutter drainage system and overhead garage storage racks, offering both convenience and functionality. Located in Johns Lake Pointe, residents enjoy access to resort-style amenities including a community pool, fitness center, playground, and sports courts, all while being just minutes from major highways, shopping, dining, Winter Garden's Historic Plant Street, and everything Central Florida has to offer. Only a short drive to Disney! Close to HIGH-RATED SCHOOLS. This is a rare opportunity to own a move-in ready home that combines space, upgrades, and lifestyle in one exceptional package. Call now for your private showing!
Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)
Listing Agent: Andrew Kincaid (407-304-0454)
15326 JOHNS LAKE POINTE BLVD, WINTER GARDEN, FL 34787
$1,385,00025 Days on yellowkey MLS ID: S5150851
1 Days Off yellowkey (back on 6/5/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3495 Built: 2014Monthly Fee: $128 Tax: $7,670 (2025)Community: Johns Lake PointeSpa: YesSingle Family
Taxes:$7,670
Remarks: Under contract-accepting backup offers. Welcome to luxury lakefront living on the shores of sought-after Johns Lake. Perfectly positioned with breathtaking west-facing sunset views, this fully upgraded waterfront residence offers the ultimate blend of elegance, comfort, and resort-style outdoor living in one of Winter Garden’s most desirable communities. Featuring nearly 3,500 square feet on 1 floor of thoughtfully designed living space, this exceptional home showcases 4 bedrooms, 3.5 bathrooms, a 3-car garage, premium hardwood flooring, and a gourmet chef’s kitchen with high-end finishes, upgraded cabinetry, and expansive entertaining space. Designed to maximize the waterfront lifestyle, the home seamlessly transitions outdoors to a private backyard retreat complete with a sparkling pool, oversized spa, outdoor kitchen, and stunning panoramic lake views — the perfect setting for sunset entertaining year-round. Additional highlights include a newer roof and HVAC systems (approximately 3 and 5 years old), luxurious updated interiors, spacious living areas. This rare Johns Lake opportunity combines elevated style with effortless move-in-ready convenience. With premium designer furnishings negotiable. Making this a possible true turnkey opportunity. Located within the highly sought-after Johns Lake Pointe community, residents enjoy proximity to historic downtown Winter Garden, top-rated schools, shopping, dining, major highways, and Orlando’s world-class attractions. Experience the best of Central Florida lakefront living in a home where every evening ends with unforgettable sunsets over Johns Lake.
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Carlos Facchinat (407-433-8109)
15187 HARROWGATE WAY, WINTER GARDEN, FL 34787
$435,00068 Days on yellowkey MLS ID: TB8497081
REDUCED by $10,000 (2.2%) on 06/06/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1296 Built: 2003Monthly Fee: $46 Tax: $5,808 (2025)Community: Stone CrkSingle Family
Taxes:$5,808
Elementary School: Whispering Oak Elem
Remarks: Location! Location! Welcome to this wel maintained 3 beds 2 bath single family home located in the desirable community of Stone Creek in Winter Garden. This home offers a spacious living room, dining area, spacious master bedroom with double sink and walking closet, 2 extra bedrooms and sharing bath, 2 car garage, screened porch and generous fenced back yard. This property is convenient located near shops, restaurants, and the highly rated Elementary School is located inside the community with walking distance. Also, near Winter Garden village Mall, Stonybrook West Golf Club, Tucker Ranch Wellness Park (in construction) And easy acces to the Highway and Airport.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Maria Howard (410-422-3518)
16746 TURTLE HATCH DR, WINTER GARDEN, FL 34787
$1,265,00034 Days on yellowkey MLS ID: O6406556
1 Days Off yellowkey (back on 6/6/2026)
Bed: 6 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4451 Built: 2018Monthly Fee: $215 Tax: $9,540 (2025)Community: Waterside/Johns Lk-Ph 1Single Family
Taxes:$9,540
Remarks: Behind the gates of the Waterside community in Winter Garden, this exceptional residence offers a rare blend of luxury, thoughtful design, and modern functionality. Built in 2018, this beautifully upgraded 6 bedroom, 4.5 bathroom home spans 4,451 square feet and includes a spacious 3 car garage, all positioned within one of Winter Garden’s most desirable gated communities. From the moment you enter through the charming front courtyard entrance, the home showcases refined finishes, expansive living spaces, and an open concept layout designed for both everyday comfort and upscale entertaining. A dramatic two story entry and soaring two story great room create an impressive first impression, while abundant natural light pours throughout the home enhancing the warm yet elegant atmosphere. Additional architectural details including crown molding, tray ceilings, and elegant rod iron stair railings further elevate the design. The gourmet kitchen serves as the centerpiece of the home featuring quartz countertops, a designer tile backsplash, vent hood, gas range, double convection ovens, oversized island, abundant cabinetry, built-in desk area, and an expansive eat in kitchen area ideal for both casual dining and entertaining family and guests. The thoughtfully designed first floor features a spacious primary suite highlighted by tray ceilings, ceiling fan, dual walk in closets, and a spa inspired ensuite bathroom complete with dual sinks, granite countertops, garden tub, and a luxurious walk-through shower with dual shower heads. A private guest suite with its own ensuite bath and tile glass enclosed walk in shower offers the perfect setup for visitors or multi generational living. A dedicated office with double door entry, elegant formal dining room with tray ceiling, expansive great room, convenient half bath, and exceptional storage throughout further enhance both the functionality and sophistication of the home. Upstairs, the second floor features four additional bedrooms, two additional bathrooms, and a spacious bonus room with double door entry complete with a private balcony overlooking the backyard, creating the perfect retreat for entertaining, relaxing, or family gatherings. Outdoor living is equally impressive with a covered rear patio featuring pavers and ceiling fan, offering the perfect place to relax or entertain while enjoying the privacy of having no rear neighbors. The property also offers ample space to create your dream pool and outdoor entertaining area. Additional highlights include a tankless water heater, window blinds throughout, crown molding, and the home is prewired for a future outdoor kitchen. Neighborhood amenities include a community pool, recreational facilities, and playground. Located within gated Waterside, residents enjoy a private and exclusive atmosphere while remaining just minutes from top rated schools, shopping, dining, Disney, downtown Winter Garden, and major roadways including the 429, Turnpike, and 408. This is more than a home, it is a lifestyle defined by space, craftsmanship, privacy, and location in one of Central Florida’s premier communities
Listing is courtesy of: CLOCK TOWER REALTY (407-832-7332)
Listing Agent: Jennifer Mitchell (803-414-1133)
14411 HAMPSHIRE BAY CIR, WINTER GARDEN, FL 34787
$895,00018 Days on yellowkey MLS ID: O6413972
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4010 Built: 2005Monthly Fee: $182 Tax: $11,924 (2025)Community: Bay Isle 48 17Spa: YesSingle Family
Taxes:$11,924
Remarks: Nestled within the prestigious gated enclave of Bay Isle, this distinguished Toll Brothers home offers a rare combination of sophisticated design, thoughtful craftsmanship, and resort-caliber amenities — all within walking distance of Winter Garden Village and AdventHealth. A soaring two-story foyer and grand living room welcome you with an abundance of natural light streaming through an exceptional array of windows — a hallmark of the home's open, airy character. At the heart of the home lies a commanding gourmet kitchen, completely updated in 2021 with quartz countertops, a handsome marble backsplash, and a professional-grade induction cooktop with custom hood vent. Rich cherry cabinetry, a wall oven, built-in microwave, generous center island, and extensive counter space are all finished with elegant crown molding — flowing seamlessly into the expansive family room with French doors opening to the outdoor living area. The main-level primary suite is a true sanctuary, featuring rich laminate flooring, serene pool and spa views, and architectural transom windows that elevate the abundant natural light. Two oversized walk-in closets with custom built-in organization systems flank a luxurious en-suite bath complete with a dual-sink vanity, deep soaking tub, and a spa-inspired walk-in shower. Upstairs, three additional bedrooms offer both privacy and connection. A private en-suite bedroom with generous walk-in closet is discreetly separated via a catwalk, while two additional bedrooms share a well-appointed Jack-and-Jill bath with individual vanity areas and a shared water closet and tub/shower. Your private home theater is fully equipped for the ultimate cinematic experience — theater seating, a 4K HD projector, Dolby surround sound, all convey with the home. The space also offers flexibility as a fifth bedroom. A loft game area and additional half bath complete the upper level's entertainment suite. Step outside to your private oasis: a sparkling pool and spa enclosed within an oversized screened lanai, complete with an outdoor shower and multiple seating areas ideal for effortless outdoor entertaining. An additional state of the art Clearlight 2 person infrared sauna provides relaxation, and rejuvenation. A three-car split garage — two bays connected to the main home, a third independently accessed — provides exceptional versatility for a workshop, boat storage, collector vehicles, or extra storage. A dedicated EV charging station is already in place. Eight-foot interior doors and extensive crown molding throughout reinforce the home's refined aesthetic. New roof (2019) · Pool pump (2018) · Full kitchen renovation (2021) Bay Isle's gated grounds feature a park, playground, walking trail, and a fishing pier on Black Lake — offering a tranquil, connected lifestyle just minutes from major roadways and every amenity Winter Garden has to offer.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Julie Bettosini, Pa (321-689-9594)
1651 AMSEL FALLS PARK TER, WINTER GARDEN, FL 34787
$1,080,00018 Days on yellowkey MLS ID: O6414027
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3881 Built: 2017Monthly Fee: $184 Tax: $6,540 (2025)Community: TwinwatersSingle Family
Taxes:$6,540
Remarks: Welcome home to this beautifully maintained 4-bedroom, 3 full bath, residence in sought-after Twinwaters. Featuring a designer kitchen with full-extension soft-close drawers and cabinets, 10-foot ceilings on the main level, 9-foot ceilings upstairs, crown molding, and central vacuum, this home offers both comfort and thoughtful upgrades throughout. Enjoy peaceful views of the expansive conservation area from your backyard with no rear neighbors, creating a private and relaxing setting. Professionally designed landscaping provides year-round color and fragrance, while local songbirds add to the natural charm. On clear evenings, catch a glimpse of Disney fireworks from home. Conveniently located just minutes from historic Downtown Winter Garden, shopping, dining, and premier golf destinations including Orange County National. Complete with a spacious 2-car garage, this warm and inviting home is ready for its next owner. Schedule your private showing today!
Listing is courtesy of: FOLIO REALTY LLC (407-917-0241)
Listing Agent: Jennifer Dollar (407-252-3762)
14755 MASTHEAD LANDING CIR, WINTER GARDEN, FL 34787
$580,00040 Days on yellowkey MLS ID: O6408082
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2258 Built: 2004Monthly Fee: $253 Tax: $8,397 (2025)Community: Stoneybrook WestSpa: NoSingle Family
Taxes:$8,397
Remarks: Located in the highly desirable Stoneybrook West community, this beautifully maintained 4-bedroom, 2-bath home offers the perfect blend on comfort, style, and convenience. Featuring a newer roof installed in 2019, brand-new 2025 central air conditioning system, newer refrigerator, new range/oven, and new dishwasher. The home welcomes you with abundant natural light, an open concept layout, and spacious living areas enhanced by attractive laminate flooring throughout. One of the home's standout features is the serene pond view from the screened lanai. With four bedrooms and versatile living spaces, this home easily accommodates families of all sizes.
Listing is courtesy of: SUSANA JORDAN STUTSMAN (321-278-0334)
Listing Agent: Susana Stutsman (321-278-0334)
2123 PORTCASTLE CIR, WINTER GARDEN, FL 34787
$389,00021 Days on yellowkey MLS ID: O6412643
0 Days Off yellowkey (back on 6/4/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1606 Built: 2006Monthly Fee: $46 Tax: $5,857 (2025)Community: Stone Creek Unit 4Single Family
Taxes:$5,857
Remarks: One or more photo(s) has been virtually staged. Welcome to your family's next home in the highly desirable Stone Creek community of Winter Garden. This spacious two-story residence features 4 bedrooms, 2.5 bathrooms, and a versatile upstairs loft, perfect for a home office, playroom, or additional living space. Step inside to an open-concept living and dining area with stylish flooring throughout—no carpet throughout! The thoughtfully designed floor plan offers all four bedrooms upstairs, providing privacy and separation from the main entertaining areas. The spacious primary suite features an en-suite bathroom with dual vanities and a walk-in closet. Conveniently located downstairs, you'll find the laundry room and a half bath for guests. Families will appreciate being zoned for Whispering Oak Elementary School, a National Blue Ribbon School and one of the highest-rated schools in the Orlando area. Enjoy an unbeatable location just minutes from Winter Garden Village, Hamlin Town Center, and historic Downtown Winter Garden, with easy access to State Road 429 and the Florida Turnpike. Plus, Disney World and Orlando's top attractions are only a short drive away. Don't miss this opportunity to own a beautiful home in one of Winter Garden's most sought-after communities.
241 N DILLARD ST, WINTER GARDEN, FL 34787
$1,499,999246 Days on yellowkey MLS ID: O6353975
REDUCED by $100,001 (6.3%) on 04/13/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 3507 Built: 1953 Tax: $2,959 (2024)Community: J L Dillard Sub 3Single Family
Taxes:$2,959
Remarks: Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden. Set on a lot boasting an expansive 214 feet of frontage, a rare and highly sought after feature that enhances both privacy and presence. Nestled beneath the shade of enchanting oak trees, this stately residence sits proudly on a rare triple lot in one of Central Florida’s most coveted locations — the Golf Cart District of Historic Downtown Winter Garden. Blending timeless character with modern comfort, this property captures the essence of classic Florida living just steps from the West Orange Trail, Lake Apopka, and all the boutiques, restaurants, and entertainment that make Plant Street so special. Step inside and you’ll immediately sense the warmth and natural light that fill every corner of this inviting home. Soaring windows and panoramic glass doors create an airy, open atmosphere, seamlessly connecting the indoors with the lush, private grounds outside. The layout offers three spacious bedrooms and three bathrooms perfectly designed for both daily living and entertaining. The primary bedroom is highlighted with a relaxing hot tub, creating a private retreat within this charming home. At the heart of the home, the oversized living and dining areas flow effortlessly into the kitchen and outdoor spaces, ideal for hosting gatherings under the canopy of mature oaks. Every room feels bright and welcoming, and you’ll always be reminded that you’re just moments away from all the charm, energy, and convenience of Downtown Winter Garden — one of the most desirable small-town destinations in Florida. The property’s expansive outdoor footprint sets it apart — a dream for anyone who values space, privacy, and possibility. The triple lot provides ample room for future additions, a pool, or a garden oasis, while a grandfathered-in workshop offers incredible flexibility for hobbies, storage, or creative endeavors. An additional extended driveway offers generous space to accommodate 2–3 vehicles comfortably, with ample room for a boat, RV, or guest parking — a rare find in this highly sought-after downtown location. Whether you’re arriving by car or golf cart, convenience is unmatched. Enjoy the best of Winter Garden living with shopping, dining, the Farmers Market, Plant Street Market, and the Garden Theatre all within minutes, plus easy access to major highways for seamless commutes. From its timeless curb appeal and breathtaking natural light to its unparalleled location and lot size, this property represents a truly rare offering in one of Florida’s most beloved communities. Opportunities like this simply don’t come around twice. Come see for yourself why this remarkable downtown retreat isn’t just a home — it’s a legacy waiting to be continued.
16783 TURTLE HATCH DR, WINTER GARDEN, FL 34787
$1,199,99946 Days on yellowkey MLS ID: O6404708
0 Days Off yellowkey (back on 6/5/2026)
REDUCED by $1 (0.0%) on 05/20/2026
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3513 Built: 2019Monthly Fee: $240 Tax: $13,161 (2025)Community: Waterside/Johns Lk-Ph 1Single Family
Taxes:$13,161
Remarks: An exceptional expression of refined living, this luxury estate is nestled within the exclusive gated enclave of Waterside at Johns Lake in Winter Garden. Boasting 5 bedrooms and 5.5 baths, this impeccably designed residence showcases a seamless blend of sophistication and comfort. The expansive open-concept layout is enhanced by elegant wood plank tile flooring throughout the main level and anchored by a chef-inspired gourmet kitchen, thoughtfully appointed for both everyday living and upscale entertaining. The lavish primary suite serves as a private sanctuary, featuring a spa-caliber bath and an oversized walk-in closet designed to impress. Step outside to your own resort-style retreat, where a screened-in pool and spa create the perfect setting for relaxation, complete with a dedicated pool bath for added convenience. The upper level offers a versatile bonus room along with a private guest suite, providing ideal accommodations for visitors or multigenerational living. Distinguished features include a 3-car garage, stately slate tile roof, charming courtyard entry, and a fully integrated irrigation system—every detail curated for both elegance and ease. Residents enjoy access to an array of resort-style amenities, including a clubhouse, state-of-the-art fitness center, community pool, fishing dock, scenic walking paths, parks, and playgrounds. Perfectly positioned just minutes from the charm of Historic Downtown Winter Garden, Winter Garden Village, Hamlin, and Horizon West, with convenient access to major thoroughfares and Central Florida’s premier attractions
Listing is courtesy of: SIERRA REALTY GROUP LLC (407-557-3119)
Listing Agent: Sylvester Harding (407-557-3119)
68 N PARK AVE, WINTER GARDEN, FL 34787
$1,799,00067 Days on yellowkey MLS ID: O6400066
REDUCED by $50,000 (2.7%) on 06/05/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3555 Built: 2021Monthly Fee: $325 Tax: $15,594 (2025)Community: 30 North ParkTownhouse
Taxes:$15,594
Remarks: Experience the ultimate in luxury urban living at 68 N Park Ave, a stunning 3-story townhome with rooftop deck located in the heart of Historic Downtown Winter Garden. This sophisticated 4-bedroom, 4.5-bathroom residence offers over 3,500 sq. ft. of meticulously designed space, seamlessly blending modern elegance with the charm of the historic district. The open-concept main level features soaring 11-foot ceilings, expansive industrial-style windows, and a chef’s dream kitchen equipped with an oversized quartz island, natural gas appliances, and custom artisan cabinetry. Accessibility is effortless with your own private elevator serving all floors. Retreat to the third-floor master suite, featuring a spa-inspired bath and massive walk-in closet, or host guests in the versatile first-floor bedroom suite. The "wow factor" continues on the 1,200 sq. ft. private rooftop terrace, offering panoramic views of the city skyline—the perfect spot for evening cocktails or watching local fireworks.Location is everything. Leave your car in the 2-car garage and embrace the golf-cart-friendly lifestyle. You are just steps away from: The award-winning Winter Garden Farmers Market, The vibrant Plant Street Market and Crooked Can Brewing Co, The world-class West Orange Trail for biking and running, Boutique shopping, fine dining, and the historic Garden Theatre. Don’t miss this rare opportunity to own a piece of downtown luxury. Schedule your private showing today!
Listing is courtesy of: VISTA CAY REALTY COMPANY (407-996-4656)
Listing Agent: Mauro Costa (321-231-6800)
1432 MARBLE CREST WAY, WINTER GARDEN, FL 34787
$824,50071 Days on yellowkey MLS ID: O6398054
4 Days Off yellowkey (back on 6/2/2026)
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3734 Built: 2005Monthly Fee: $243 Tax: $7,963 (2025)Community: Stoneybrook West 44/134Spa: YesSingle Family
Taxes:$7,963
Remarks: Under contract-accepting backup offers. GOLF COURSE POOL HOME + TILE ROOF + GUARD-GATED LIVING in one of Winter Garden’s most sought-after communities. Welcome to 1432 Marble Crest Way, located in the Fox Hunt section of Stoneybrook West, a 24-hour manned, guard-gated golf community known for its distinctive Mediterranean-style homes, mature landscaping, and resort-style amenities. This 5-bedroom, 3.5-bath home offers over 3,700 square feet of flexible living space with multiple living areas, a private office, and recent buyer-visible updates throughout. Designed for both everyday living and entertaining, the layout includes formal dining, two spacious first-floor living areas, and an oversized upstairs bonus room ideal for a media room, game room, fitness space, playroom, or secondary retreat. The private office offers flexibility for remote work, hobbies, or a quiet study space. The kitchen opens to the main family room, creating a comfortable flow for gathering and everyday living, while natural light fills the home throughout. Recent improvements include NEW UPSTAIRS FLOORING, FRESH INTERIOR PAINT in many rooms, and UPDATED FIXTURES, giving the home a refreshed and move-in-ready feel. Step outside to a SCREENED-IN POOL overlooking the golf course, complete with a BUILT-IN OUTDOOR KITCHENETTE and a RECENTLY REFINISHED POOL—perfect for relaxing evenings, entertaining, and enjoying Florida living year-round. Stoneybrook West offers an amenity-rich lifestyle including 24-hour guard-gated security, golf, clubhouse, fitness center, resort-style pool, tennis, pickleball, basketball, playgrounds, fishing dock, boat ramp with Black Lake access, and the Stoneybrook West Golf Club with SB Prime restaurant and bar. Ideally located just minutes from Winter Garden Village, downtown Winter Garden, SR-429, Disney, shopping, dining, and everyday conveniences.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
92 WINDTREE LN #201, WINTER GARDEN, FL 34787
$218,000168 Days on yellowkey MLS ID: O6371247
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 918 Built: 1984Monthly Fee: $300 Tax: $2,362 (2024)Community: Windtree Gardens Condo Ph 03Condo
Taxes:$2,362
Remarks: Don’t miss this great investment opportunity in the heart of Winter Garden. This 2-bedroom, 2-bath condo offers laminated floors and is already rented, generating income from day one. Home features updated plumbing with a complete repipe. Located just minutes from Downtown Winter Garden, with easy access to restaurants, shops, parks, and major highways. Not a gated community, offering easy access and low-maintenance living. Perfect for investors seeking a stable, income-producing property.
Listing is courtesy of: ROMAN'S PRO REALTY LLC (407-610-1970)
Listing Agent: Maria Perez (407-496-2336)
156 STANTON ESTATES CIR, WINTER GARDEN, FL 34787
$1,149,950110 Days on yellowkey MLS ID: O6384801
REDUCED by $50,050 (4.2%) on 06/03/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3170 Built: 2018Monthly Fee: $188 Tax: $7,979 (2024)Community: Stanton EstatesSingle Family
Taxes:$7,979
Remarks: **We've just introduced a significant price reduction, creating an exceptional opportunity for new owners. ** **Welcome to Golf Cart Life in Historic Downtown Winter Garden** Nestled within Stanton Estates — an exclusive enclave of just 45 luxury homes — this contemporary masterpiece places you in the heart of **Winter Garden’s vibrant Golf Cart District**, where every day feels like a getaway. Built in 2018, this one-story multigenerational estate offers 3,170 sq ft of refined living on a nearly 1/3-acre lot, just a quick golf cart ride from **Plant Street’s award-winning restaurants, live music, boutique shops, the famous Saturday Farmer’s Market, the Crooked Can Brewery, and the scenic West Orange Trail**. Take a look at Virtual Tour Link 2 to see all the exciting and fun things available to you in the downtown and historic area of Winter Garden. Inside, soaring 12-ft ceilings and natural light flow through an open, flexible layout with four bedrooms, four full baths, and a private office. The gourmet kitchen anchors the home with solid wood cabinetry, quartz countertops, an oversized island, walk-in pantry, and a full suite of KitchenAid Professional appliances with natural gas. The primary suite features a recessed ceiling, expansive custom walk-in closet, and a spa-inspired bath. Fully retractable sliders open to a covered lanai surrounded by mature, professionally designed landscaping and privacy fencing — your own private Florida retreat after a day of exploring downtown. Premium upgrades include smart-home technology, motorized shades, whole-home water filtration, 8-ft solid core doors, custom cabinetry, a three-car tandem garage with brick paver driveway, and a brand-new tankless gas water heater (2025). Just minutes from Disney, Universal, and SeaWorld, with seamless access to SR-429, the Turnpike, and 408, this address blends luxury living with the unbeatable charm and excitement of Downtown Winter Garden. Opportunities like this in Stanton Estates are rare. **Welcome to the lifestyle everyone wants**
Listing is courtesy of: FATHOM REALTY FL LLC (888-455-6040)
Listing Agent: Joe Thomas, Jr (813-724-1922)
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