Winter Garden Real Estate

Winter Garden Real Estate

Welcome to Winter Garden, Florida – a charming city that beautifully blends historic charm with modern convenience. Nestled just 14 miles west of Orlando, Winter Garden boasts a vibrant downtown area filled with quaint shops, delightful eateries, and an array of local events that foster a strong sense of community.

The city's rich history is showcased in its preserved downtown district, where you can stroll along brick-paved streets lined with century-old buildings that now house unique boutiques and artisanal cafes. The Winter Garden Heritage Museum offers a glimpse into the past, celebrating the city’s agricultural roots and the role it played in the development of Central Florida.

Nature lovers will find plenty to adore in Winter Garden. With its proximity to the West Orange Trail, residents can enjoy miles of scenic paths perfect for walking, biking, or jogging. The lush parks and scenic lakes provide ample opportunities for outdoor recreation, whether you're picnicking under the shade of ancient oaks or enjoying a leisurely afternoon on the water.

Families will appreciate the top-rated schools and safe neighborhoods that make Winter Garden a great place to raise children. With a variety of housing options, from charming historic homes to modern developments, there’s something for everyone in this welcoming community.

As a thriving city with a strong sense of identity, Winter Garden is not just a place to live; it’s a place to call home. Explore the warmth and charm of Winter Garden, where every day feels like a celebration of life in sunny Florida!

Newest Listings in Winter Garden

5960 Flowering Cherry Bend, Winter Garden
$604,990
3 Beds ⋅ 2 Baths ⋅ Avalon Woods SubDv. ⋅ 34787 Zip Code
**Location, location, location!** This brand-new Dream Finders home is perfectly positioned in the highly desirable Hamlin area, just minutes from Hamlin schools, the Hamlin Town Center, shopping, dining, and quick access to State Road 429. From here, convenience is truly at your doorstep. While the location shines, this home packs an impressive amount of functionality into 1,772 square feet. The open-concept design features a spacious kitchen with quartz countertops, wood cabinetry, stainless-steel appliances, and a large island overlooking the living and dining areas. The split-bedroom layout offers a private primary suite on one side of the home, complete with dual sinks, a soaking tub, separate shower, and walk-in closet. Two additional bedrooms are tucked away in their own separate wing, creating a comfortable and flexible space for family, guests, or a home office. With modern finishes, a covered patio, backyard, and two-car garage, this move-in-ready home delivers big on comfort, convenience, and personality—all in one of Hamlin’s most sought-after locations.

5960 Flowering Cherry Bend, Winter Garden
1229 Winter Green Way, Winter Garden
$235,000
2 Beds ⋅ 2 Baths ⋅ Village Grove Ph 02 SubDv. ⋅ 34787 Zip Code
Virtually Staged. This charming 2-bed, 1.5-bath townhouse delivers peak Central Florida convenience. Step inside to discover a bright, open interior highlighted by high ceilings and a stylish kitchen finished with sleek granite countertops. Meticulously maintained and move-in ready, it serves as the perfect low-maintenance starter home or turnkey addition to an investment portfolio. Five minutes to historic downtown Winter Garden, and under 30 minutes to Disney. Easy highway access rounds out a truly prime location. Tour Today!

1229 Winter Green Way, Winter Garden
922 Marsh Reed Drive, Winter Garden
$679,000
5 Beds ⋅ 3 Baths ⋅ Johns Lake Pointe A & S SubDv. ⋅ 34787 Zip Code
Picture a Saturday here. Coffee at the kitchen island while the pool glistens under the Florida sun. Cannonballs by noon, burgers on the grill by five, and a movie night in the loft once everyone dries off. Welcome to 922 Marsh Reed Drive, a 5 bedroom, 3 full bath saltwater pool home in Johns Lake Pointe that has been cared for like a prized possession and is ready for its next chapter. The first impression sets the tone: tropical landscaping, a brick paver driveway, a three car garage, and a covered front porch with a cheery red door. Step inside and the tiled foyer opens to a formal dining room framed by tall windows and warm natural light, the kind of room that turns holiday dinners and Sunday suppers into traditions. Keep walking and the home opens up. The kitchen is the true gathering spot, with 42" espresso cabinets, granite counters, a tiled backsplash, stainless appliances, built-in double wall ovens, pendant lighting, and a large island where homework, snacks, and conversation all happen at once. A walk-in pantry with custom shelving keeps the grocery runs organized. The eat-in dining area sits right off the kitchen with sliding glass doors to the pool, so you can keep an eye on the swimmers while dinner comes together. The family room flows right alongside, finished with crown molding, plantation shutters, and wiring for surround sound. Game day, movie night, or a lazy Sunday nap, this room handles it all. Hosting overnight company? A first-floor bedroom next to a full bath makes a private guest retreat or a quiet home office away from the upstairs bustle. Head up the staircase with wrought iron spindles and you’ll find a huge loft that gives everyone room to spread out: game room, playroom, homework zone, or second living room. Three secondary bedrooms share a full bath, and the laundry room is right here on the second floor with custom cabinetry, which means no more hauling baskets up and down the stairs. The primary suite is split to its own side of the second floor, with windows on two sides and room for a reading chair. The en suite bath feels like a getaway, with dual sinks and granite counters, a frameless glass shower, a separate garden tub for long soaks, and two walk-in closets so nobody has to negotiate for hanger space. Then there’s the backyard, where this home really shines. The saltwater pool is heated by solar panels, extending swim season well beyond summer. An extended paver deck has room for a full grill lineup, a dining table, and lounge chairs, with an electric retractable awning for shade when you want it. Vinyl privacy fencing wraps the entire yard, giving you a private oasis with plenty of grass for playing catch or running through the sprinkler. Smart upgrades work quietly in the background: rain gutters around the entire home, French drains in the yard, whole-home water softening system, and a central vacuum in the garage. Life in Johns Lake Pointe adds even more to love, with a resort-style community pool, clubhouse, fitness center, tennis courts, playground, and walking trails. Bike the West Orange Trail, catch the Saturday farmers market in Historic Downtown Winter Garden, explore Tucker Ranch, or shop and dine at Winter Garden Village, all just minutes away. SR 429, SR 408, and the Florida Turnpike make commutes and theme park days easy. Homes like this don’t come along often. Schedule your private showing and see why this one is ready to feel like yours.

922 Marsh Reed Drive, Winter Garden
651 Autumn Oaks Loop, Winter Garden
$535,000
3 Beds ⋅ 2 Baths ⋅ Winter Oaks SubDv. ⋅ 34787 Zip Code
Live the Winter Garden lifestyle you've been dreaming of in the Winter Oaks community, with oak-lined streets and golf cart access to downtown. Situated in the Golf Cart District, this park-side residence overlooks majestic oaks and open green space. The 3-bedroom, 2-bath, 1,768 sq ft home features a 2021 ROOF, 2021 HVAC, UPDATED LIGHT FIXTURES, a GAS STOVE, a REAR-ENTRY 2-CAR GARAGE, and a RECENTLY PAINTED INTERIOR, with freshly painted bedrooms, baths and laundry room. As you walk in, you're greeted by natural light and an open, welcoming feel. A formal dining room and an open kitchen flow into the spacious family room, which leads out to a NEWLY RE-SCREENED back patio overlooking a beautifully manicured lawn and garden. The primary suite includes a spacious walk-in closet and a private bath with dual sinks, a soaking tub, and a separate shower. Winter Oaks offers a community pool, cabana, playground, and scenic pond. Hop in your golf cart to Plant Street for dinner, a show at the Garden Theatre, or the Saturday farmers market. Minutes from the West Orange Trail, Tucker Ranch, and Newton Park, Winter Garden Village with an easy drive to SR 429 and the Florida Turnpike. Convenient access to Disney, Universal, Epic Universe, and downtown Orlando. Schedule your private showing today!

651 Autumn Oaks Loop, Winter Garden
13728 Fox Glove Street, Winter Garden
$649,900
5 Beds ⋅ 4 Baths ⋅ Stoneybrook West Ut 04 48 48 SubDv. ⋅ 34787 Zip Code
Spacious 5-bedroom, 3.5-bath home with 3,391 square feet overlooking the 14th hole of the golf course in Stoneybrook West. The main floor features a primary suite, a second bedroom with its own en-suite bathroom, and a separate powder room. Upstairs are three additional bedrooms and a full bathroom. The home features high ceilings, an open floor plan, plenty of natural light, and a 2-car garage. Sliding glass doors open to a large covered patio and screened-in private pool with golf course views. Recent improvements include a new roof (2025), upstairs AC (2025), and downstairs AC (2022). Stoneybrook West is a 24-hour guard-gated community with a clubhouse, fitness center, community pool, tennis courts, playground, and access to Black Lake with a private boat ramp. Conveniently located near Winter Garden Village, downtown Winter Garden, and SR-429.

13728 Fox Glove Street, Winter Garden
949 Celadon Street, Winter Garden
$2,195,000
5 Beds ⋅ 5 Baths ⋅ Oakland Parka SubDv. ⋅ 34787 Zip Code
Discover exceptional custom craftsmanship in this J&J Builders home, located in a golf cart-friendly community just minutes from downtown Winter Garden and the West Orange Trail. Featuring 5 bedrooms and 4.5 bathrooms, this home offers a thoughtfully designed open floor plan with beautiful views of Lake Apopka. The spacious chef's kitchen is the heart of the home, featuring high-end Sub-Zero and Miele appliances and creating an ideal setting for everyday living and entertaining. A dedicated office offers the flexibility to serve as a potential sixth bedroom. The stunning upstairs primary suite is a true retreat, showcasing dramatic cathedral beamed ceilings and breathtaking lake views. An additional private suite downstairs offers flexibility for guests or multigenerational living, while two additional upstairs bedrooms share a bath. The home also features a separate in-law suite with its own kitchenette, providing even more versatility for extended family or visitors. Designed for comfortable living and effortless entertaining, the home seamlessly blends indoor and outdoor living. Step outside to your own private retreat, featuring a heated inground pool and spa, an inviting covered lanai, and a fully equipped outdoor kitchen with automatic retractable screens. Gather around the natural gas fire pit with included outdoor furnishings and enjoy beautiful Florida evenings. Additional highlights include a large garage attic storage room with convenient accordion-style metal access stairs, offering valuable extra storage space. Enjoy the best of Winter Garden living with custom craftsmanship, high-end finishes, versatile living spaces, resort-style outdoor amenities, and convenient access to the area's beloved shops, dining, and outdoor recreation!

949 Celadon Street, Winter Garden
8199 Gray Kingbird Drive, Winter Garden
$715,000
4 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 4b SubDv. ⋅ 34787 Zip Code
Welcome to a spacious and energy-conscious home offering flexible living spaces, exceptional storage and a convenient location just minutes from Hamlin. The open-concept main living area connects the kitchen, dining space and family room—perfect for both everyday living and entertaining. The kitchen features granite countertops, abundant cabinetry, stainless steel appliances, a gas range and a generous island with seating. The first-floor primary suite offers a comfortable retreat with an en-suite bath and two walk-in closets. Upstairs, you’ll find three spacious bedrooms and an oversized bonus room—currently used as a home gym and equally suited for a second living room, media room, playroom or home office. Plentiful closets provide storage throughout the home. Outside, the large fenced backyard offers plenty of room for pets, play and outdoor living. Additional highlights include a tankless gas water heater and fully paid solar panels. The seller reports average electric bills of approximately $50 per month; usage may vary. Enjoy easy access to Hamlin’s growing collection of restaurants, shopping, entertainment and community events.

8199 Gray Kingbird Drive, Winter Garden
15625 Murcott Harvest Loop, Winter Garden
$650,000
3 Beds ⋅ 3 Baths ⋅ Highlands At Summerlake Groves Phase 1 SubDv. ⋅ 34787 Zip Code
Beautifully appointed SINGLE-STORY home in the highly desirable Summerlake community of Horizon West! The GOURMET KITCHEN is sure to impress with a massive center island, stainless steel appliances, GAS COOKTOP, built-in wall oven and microwave, stunning backsplash, and walk in pantry. 8 FOOT DOORS, CROWN MOLDING, and Phillips Hue SMART LIGHTING are some of the additional design upgrades. You will love the open, inviting floor plan. The open office offers flexibility and can easily be converted into a 4TH BEDROOM. Enjoy energy efficiency and significant savings with SOLAR PANELS, which will be PAID IN FULL AT CLOSING, and an average electric bill of approximately $30 per month! Additional energy upgrades include a TANKLESS WATER HEATER and a NEW HIGH-EFFICIENCY AC SYSTEM with TWO UV FILTERS. Summerlake is a natural gas community offering an impressive array of amenities, including a clubhouse, RESORT-STYLE POOL, fitness center, tennis and basketball courts, playgrounds, parks, and miles of walking and biking paths, with scenic boardwalks connecting lakes and natural areas. The HOA also includes CABLE AND INTERNET! Conveniently located near Hamlin Town Center for shopping, dining, coffee shops, and entertainment, with additional shopping and restaurants at Winter Garden Village. Enjoy the charm of Historic Downtown Winter Garden, Plant Street Market, the weekly farmers market, and the West Orange Trail. Golf enthusiasts will appreciate nearby Orange County National Golf Center. Easy access to SR-429 puts Walt Disney World and the greater Orlando area within easy reach. This home offers the perfect combination of style, comfort, energy efficiency, and an outstanding Horizon West lifestyle!

15625 Murcott Harvest Loop, Winter Garden
906 Woodson Hammock Circle, Winter Garden
$550,000
4 Beds ⋅ 2 Baths ⋅ Fullers Crossing Ph 01 44/14 SubDv. ⋅ 34787 Zip Code
ONE-OWNER CAMBRIDGE-BUILT HOME WITH A POOL, SPA & PRIVATE FENCED BACKYARD! Pride of ownership shines throughout this well-maintained home featuring mature landscaping, a white vinyl privacy fence, and easy-care porcelain tile and engineered wood flooring throughout—no carpet! The traditional floor plan offers formal living and dining rooms, while the kitchen features stainless steel appliances, with ALL kitchen and laundry appliances included. Step outside and discover the perfect place to relax or entertain in the oversized screened patio overlooking an Artesian-built inground pool and spa. A utility shed provides additional storage, and the fully fenced backyard offers added privacy and room to enjoy the outdoors. Enjoy the outstanding lifestyle that Winter Garden has to offer, including popular shopping, dining, entertainment, golf cart-friendly accessibility, the West Orange Trail, and fishing and water sports on beautiful Lake Apopka. Convenient access to SR 429 and other major highways and toll roads makes commuting and reaching Central Florida's world-famous attractions a breeze. A wonderful opportunity to enjoy the Winter Garden lifestyle with the added bonus of your own private pool and spa!

906 Woodson Hammock Circle, Winter Garden
9953 Summerlake Groves Street, Winter Garden
$774,900
4 Beds ⋅ 4 Baths ⋅ Watermark Ph 4a SubDv. ⋅ 34787 Zip Code
Premium Corner Lot! Discover this beautiful two-story home in the sought-after Watermark community of Horizon West in Winter Garden! Situated on a desirable corner lot, this well-maintained home offers 4 spacious bedrooms, a den, a versatile bonus room, an office, 3.5 bathrooms, and an oversized two-car garage with epoxy flooring. Step inside to a bright and welcoming open floor plan featuring abundant natural light and a spacious layout designed for comfortable everyday living. The inviting living room connects seamlessly to the covered lanai, featuring an outdoor summer kitchen, creating a wonderful space for relaxing, entertaining, and enjoying Florida's beautiful weather. The gourmet kitchen features a large center island with a sink, generous space for preparing meals, and an adjoining dining area perfect for family gatherings. Upstairs, the primary suite provides a relaxing retreat with access to a private screened balcony, where you can enjoy your morning coffee or unwind in the evening. The additional bedrooms offer comfortable living spaces, while the versatile bonus room can easily serve as a playroom, media room, or additional entertainment area. This home also features a fully functional water softener system, hot and cold water connections, and sewer service, adding convenience and functionality to everyday living. Outside, the fully fenced backyard offers added privacy and plenty of space for outdoor activities and gatherings. The oversized two-car garage with epoxy flooring provides additional convenience and storage space. Residents of Watermark enjoy resort-style amenities, including a community pool, splash pad, playground, tennis courts, recreation center, and outdoor amphitheater. Conveniently located in the heart of Horizon West, this home is just minutes from Disney, shopping, restaurants, and entertainment, with easy access to SR-429 for convenient travel throughout Central Florida. With its premium corner lot, spacious interior, desirable features, fantastic community amenities, and excellent Winter Garden location, this home offers a wonderful opportunity to experience the best of Florida living!

9953 Summerlake Groves Street, Winter Garden
194 & 196 Mary Street, Winter Garden
$299,000
2 Beds ⋅ 2 Baths ⋅ Mary Jean Sub SubDv. ⋅ 34787 Zip Code
Welcome to 194 & 196 Mary Street, a beautifully refreshed duplex in the heart of charming Winter Garden! This solid block home offers 960 square feet of heated living space split into two units, each with one bedroom, so it’s an easy fit for investors, house hackers, or anyone looking to live in one side and let the other help pay the mortgage. Please note: the county tax records list the property as 194 Mary Street, but the units are addressed as 194 and 196 Mary Street, and that’s how they’re set up with the water and electric utilities. Step inside and you’ll find bright, freshly updated interiors with durable, water-resistant luxury vinyl plank flooring throughout, crisp white walls, and stylish modern lighting. The kitchens feature clean white cabinetry and sleek finishes, while the bathrooms impress with floor-to-ceiling marble-look tile and contemporary fixtures. Each unit also offers convenient in-unit washer and dryer hookups, a big plus for tenants and owners alike! Ductless mini-split A/C keeps every room comfortable all year long. Just minutes from downtown Winter Garden’s shops, restaurants, farmers market, and the West Orange Trail, this is a turnkey opportunity you won’t want to miss. Schedule your showing toda

194 & 196 Mary Street, Winter Garden
580 First Cape Coral Drive, Winter Garden
$675,000
4 Beds ⋅ 3 Baths ⋅ Black Lake Park Ph 01 SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to Black Lake Park, one of Winter Garden's sought-after gated communities, where spacious family living, fantastic amenities and an enviable location come together to create the perfect Florida lifestyle! Offering 4 SPACIOUS BEDROOMS, 2 1/2 BATHROOMS, AND HUGE LOFT AREA, this beautiful home provides the ideal combination of comfort, space and functionality. The welcoming open-plan layout creates an easy flow between living spaces, making everyday family life effortless, and entertaining a pleasure. With NO CARPETS THROUGHOUT, NEWLY PAINTED INTERIOR and a NEW ROOF – INSTALLED DECEMBER 2024, this home offers even more appeal and peace of mind, with a clean, practical and easy-to-maintain living environment. Whether hosting friends, enjoying family time or simply relaxing at home, with 2834 sq ft there's room for everyone. It does not stop there. Step outside and discover what Florida living is all about! Your private fully fenced backyard retreat, features a NEW FABULOUS SALTWATER SWIMMING POOL AND SPA – INSTALLED DECEMBER 2025! Imagine soaking up the sunshine, cooling off on warm afternoons or unwinding in the spa after a busy day. With plenty of room for lounging, outdoor dining and entertaining this is an outdoor space you'll love coming home to! Life in Black Lake Park is something special! This FABULOUS, GATED, FAMILY-FRIENDLY COMMUNITY offers an outstanding range of recreational facilities, making it a wonderful place for families and those who enjoy an active outdoor lifestyle. Amenities include TENNIS COURTS, BASKETBALL COURTS, BASEBALL FIELDS, A COMMUNITY SWIMMING POOL AND PLAYGROUND, along with lovely walking paths, and COMMUNITY DOCK AND BOAT RAMP. Whether enjoying a family game, taking a leisurely stroll, spending time at the park or heading out onto the water, there's something for everyone to enjoy. It's a community where outdoor living, family fun and a wonderful neighborhood atmosphere come together. This LOCATION is hard to beat. Simply wonderful! Just minutes from the charm of Historic Downtown Winter Garden, where you'll find an abundance of restaurants, cafés, boutique shopping and the much-loved Winter Garden Farmers Market. Winter Garden Village is also close by, offering an excellent choice of shopping, grocery stores and everyday conveniences. For commuters and those who love to explore, easy access to the 429, Florida Turnpike and Highway 50 makes traveling around Central Florida very convenient. Walt Disney World and the area's world-famous attractions are also within easy reach, making this a fantastic location for enjoying everything that is available in Central Florida. Whether you're searching for your next family home, the perfect place to entertain or simply somewhere to enjoy everything the Florida sunshine has, this is an opportunity not to be missed. THIS HOME IS MOVE IN READY! COME AND DISCOVER THE LIFESTYLE WAITING FOR YOU IN BLACK LAKE PARK.

580 First Cape Coral Drive, Winter Garden
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