Winter Garden Real Estate

Winter Garden Real Estate

Winter Garden is a charming city located in Orange County, Florida. Situated in the heart of the Sunshine State, Winter Garden offers residents a unique blend of small-town charm and modern amenities. With its rich history, beautiful landscapes, and vibrant community, it's no wonder why Winter Garden is a sought-after destination for both locals and newcomers alike.

One of the highlights of Winter Garden is its historic downtown area. Here, you'll find cobblestone streets lined with quaint shops, cafes, and restaurants. The city takes great pride in preserving its heritage, and many of the buildings in the downtown area date back to the early 1900s. Strolling through the streets, you'll feel like you've stepped back in time.

In addition to its historic charm, Winter Garden also offers a variety of recreational opportunities. The city is home to numerous parks and green spaces, providing residents with ample opportunities for outdoor activities. From hiking and biking trails to community sports leagues, there's something for everyone to enjoy.

For those who prefer a more urban lifestyle, Winter Garden is conveniently located near major highways, making it easy to commute to nearby cities like Orlando. The city also boasts excellent schools, making it an ideal place to raise a family.

Whether you're looking for a place to settle down or just visiting, Winter Garden has something for everyone. With its rich history, vibrant community, and convenient location, it's no wonder why this city continues to attract people from all walks of life.

Newest Listings in Winter Garden

3 Beds ⋅ 3 Baths ⋅ O6433944 MLS ⋅ 00 BLDG.

Storey Grove ** 2023 built ** Open floorplan **BACKS TO GREENSPACE!!** Beautiful wood ceramic tile entire 1st floor ** Attractive tv wall wood accent inlay in the family room ** White kitchen cabinetry with quartz counters and large cooking island ** All bedrooms are on the 2nd floor ** Nice size +/-16x20 brick paver patio area and 2 car detached garage ** Great RING security system, RING cameras, doorbell and door and window sensors ** Tesla EV power outlet is already in place in the garage ** Overhead storage racks in the garage are included ** Storey Grove community amenities include a huge resort style community pool, fitness center, basketball courts, children's playground and green space area. Room measurements are from builder floor plan. Buyers to verify all room measurements.

10648 Words Drive, Winter Garden

4 Beds ⋅ 4 Baths ⋅ O6432972 MLS

This beautiful 4 bedroom, 3 1/2 bath home features an open layout with designer finishes that are light and bright throughout. There are 2 master bedroom one on the first floor and in the second floor Perfect for families. Large great room downstairs, bonus room/loft upstairs with vaulted ceiling and a beautiful backyard. Upgraded just like the model. Quartz counter top throughout, upgraded light cabinets, wood plank, tile floor. Upgraded GE Profile appliances and complete Smart Home Package with smart thermostats, smart switches Wireless range extenders built in Alexa smart home controls. Storey Grove is beautiful picturesque community with pool, fitness center, parks, playgrounds and more. It's a perfect location just minutes from Disney, Shopping, Dining, New Hamlin retail and theaters, Easy Access to 429 Expressway, and zoned for A rated schools . Come and check personally .

15163 Book Club Road, Winter Garden

2 Beds ⋅ 1 Baths ⋅ G5116347 MLS ⋅ 25 BLDG.

Beautifully refreshed and ready to move in today, this charming 2-bedroom, 1-bath corner condo offers an inviting combination of modern updates, natural light, and exceptional community amenities. The bright, crisp interior is filled with loads of natural light and features fresh paint throughout, brand-new carpet, new door handles, and stylish modern finishes. All appliances are included, making this home truly move-in ready. The attached garage has also been washed and painted, creating a clean and functional space for parking and storage. And when it comes to value, this one is hard to beat. This is currently the most aggressively priced 2-bedroom condo with an attached garage on the market, making it a rare opportunity for a buyer looking for the combination of price, updates, and convenience. The A/C system was newly installed in June 2026, adding another significant update and valuable peace of mind. The community offers an impressive lineup of amenities designed to enhance everyday living, including a resort-style pool and relaxing hot tub, fully equipped fitness center, indoor basketball and racquetball courts, tennis court, and a convenient car wash area. Conveniently located near 429 and the Florida Turnpike, this home provides easy access to shopping, dining, major roadways, and a short drive to Orlando's theme parks and either coastline. With its desirable corner-unit location, attached garage, extensive updates, incredible amenities, and unmatched price point, this is a rare find that won't be easy to duplicate. If you're looking for a move-in-ready 2-bedroom with an attached garage at the best value currently available, this one deserves a look!

233 Southern Pecan Circle Unit 101, Winter Garden

3 Beds ⋅ 2 Baths ⋅ O6433388 MLS

Set on a quiet cul-de-sac near the heart of Winter Garden, this updated single-story home pairs an easy, open layout with an unusually spacious backyard. Inside, 3 bedrooms and 2 bathrooms are arranged across 1,307 square feet, with vaulted ceilings and ceramic tile connecting the kitchen, dining area, and living room. The refreshed kitchen features white cabinetry, quartz countertops, a glossy subway-style backsplash, a deep undermount sink with a pull-down faucet, modern lighting, and a peninsula with breakfast-bar seating. Sliding glass doors extend the living space directly to the backyard. The primary suite offers tile flooring, a feature wall, private patio access, an en-suite bath, and a true walk-in closet. Two additional bedrooms and a second full bath provide flexible space for guests, an office, or everyday living. Fresh interior paint, updated light fixtures, ceiling fans, and a functional split-bedroom design complete the interior. Outside, the fully fenced 0.23-acre lot is a standout. A roofed pergola creates a generous shaded patio and room for outdoor dining and lounging. Beyond it, the broad lawn leads to a defined circular firepit area and a 10-by-20 storage shed, with ample open space for recreation, gardening, and outdoor hobbies. Aerial views highlight the depth and usability of the yard, while the attached two-car garage adds everyday storage and convenience. With no HOA and no CDD, the property offers flexibility in an established neighborhood close to the West Orange Trail, local parks, Lake Apopka, and the shops, dining, Plant Street Market, and brewery district of downtown Winter Garden. Enjoy an evening downtown, a weekend bike ride, or a relaxed night around the backyard firepit, all from a well-located home with room to make it your own.

1312 Corsino St, Winter Garden

4 Beds ⋅ 3 Baths ⋅ O6432899 MLS

Virtually Staged. Welcome to this beautifully renovated golf-front home in the gated community of Stoneybrook West. Offering over 2,800 square feet of living space, this home combines a spacious and flexible floor plan with a fantastic setting overlooking the 6th hole and no rear neighbors. Recent improvements include a newer roof and A/C, fresh exterior and interior paint, renovated kitchen, bathrooms, and flooring. The main level offers multiple living and dining spaces, while the kitchen features stone countertops, stainless steel appliances and abundant cabinetry. Upstairs, the spacious primary suite includes a tray ceiling, walk-in closet and private bath with dual vanities and a beautifully remodeled walk-in shower. The oversized loft provides plenty of flexibility for a second living area, media room, playroom or home office. Step outside to a large backyard with expansive golf course views and plenty of room to enjoy the outdoor living. Stoneybrook West offers an impressive collection of amenities, including a community pool, golf, clubhouse, tennis and basketball courts, playgrounds and walking paths. Ideally located near Winter Garden Village, historic Downtown Winter Garden, shopping, dining and major roadways, this home offers a great combination of space, improvements, amenities and community.

15081 Masthead Landing Circle, Winter Garden

3 Beds ⋅ 3 Baths ⋅ O6433686 MLS ⋅ 0662 BLDG.

Under Construction. Waterleigh presents the Sandhill. This spacious townhome features 3 bedrooms and 2.5 baths. As you enter the foyer you are welcomed with powder room, spacious kitchen with bar seating, dining area and a living room overlooking a covered patio. This popular townhome features a single car garage at the rear of the home. This community has upgraded stainless steel appliances and quartz countertops making cooking and cleaning a breeze. As we head upstairs, you are greeted with a loft area. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity. The second floor is complete with two guest bedrooms, an additional bathroom, along with laundry room. Like all homes in Waterleigh, the Sandhill includes a Smart home technology package which allows you to control your home with your smart device while near or away. Your new townhome will always have fantastic curb appeal while allowing you time to do the activities your family enjoys most. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

16534 Barbours Creek Way, Winter Garden

4 Beds ⋅ 3 Baths ⋅ O6433669 MLS

Welcome to 5743 Thomas Square Drive, an exceptional single-story pool home located in the lakefront community of The Cove at Hamlin in Winter Garden. Built in 2018, this beautifully upgraded Jamestown model offers 4 bedrooms, 2.5 bathrooms, 2,917 square feet, and a thoughtfully designed split floor plan that combines comfort, style, and effortless Florida living. Inside, engineered hardwood floors, custom archways, high ceilings, and abundant natural light lead into an expansive open-concept living space. The kitchen serves as the heart of the home with quartz countertops, stainless steel appliances, generous cabinetry, and seamless flow into the dining and living areas. One of the home's most impressive features is the massive owner's suite. Offering an exceptional amount of space rarely found in homes of this size, the suite easily accommodates a full bedroom setup with room for a sitting area, additional furnishings, or a private retreat within the room. A spacious owner's bath and generous custom closet complete the suite, while three additional bedrooms provide flexibility for family, guests, or a home office. Step outside to an extended screened lanai overlooking the private saltwater pool and beautifully landscaped fenced backyard. Solar and natural gas pool heating, built-in lighting, a fire pit, and a gas connection for an outdoor grill create a backyard designed for entertaining and enjoying the Florida lifestyle year-round. Lake views complete the setting, along with the opportunity to enjoy nightly Disney fireworks from home. Beyond the home, one of the biggest draws is the incredible Hamlin lifestyle just minutes from your front door. Spend an evening putting at PopStroke, catch a movie from a luxury recliner at Cinépolis, grab dinner at Ford's Garage or Agave Bandido, meet friends at Home State Brewing Co., or start the morning with coffee and breakfast at Toastique. Hamlin continues to offer an exciting mix of restaurants, entertainment, shopping, fitness, community events, and everyday conveniences, making it easy to enjoy a night out without traveling far from home. The Cove at Hamlin offers its own impressive collection of amenities, including a resort-style community pool, clubhouse, fitness center, splash pad, playgrounds, dog park, walking trails, outdoor gathering spaces, and private access to Lake Hancock with a community boat ramp and dock. With easy access to SR 429, Walt Disney World, Hamlin Town Center, and everything Horizon West has to offer, 5743 Thomas Square Drive is more than a beautiful pool home. It offers the opportunity to live in the heart of one of Central Florida's most exciting and rapidly growing communities.

5743 Thomas Square Drive, Winter Garden

2 Beds ⋅ 2 Baths ⋅ S5155653 MLS ⋅ 3 BLDG.

Located on the second floor of Building 3, closest to the Safari Water Park, this fully furnished, two-bedroom, two-bathroom condo offers fantastic pond views and excellent proximity to resort amenities. This property is perfect for vacation home buyers seeking a true resort experience. Owners will enjoy resort-style living with access to multiple pools, a water park, a full-service spa, on-site restaurants, a state-of-the-art fitness center, and a large game room. For investors, this unit presents a compelling opportunity in Central Florida's booming tourism market. Located just minutes from Walt Disney World, Universal Studios, SeaWorld, upscale shopping, and diverse dining, this property promises strong rental potential and the flexibility to generate income while serving as a personal escape.

14501 Grove Resort Avenue Unit 3215, Winter Garden

3 Beds ⋅ 3 Baths ⋅ O6433682 MLS ⋅ 0664 BLDG.

Under Construction. Waterleigh presents the Ibis. This spacious townhome features 3 bedrooms and 2.5 baths. As you enter the foyer you are welcomed with an open concept a spacious kitchen with bar seating, dining area and a living room overlooking a covered patio. This popular townhome features a single car garage and powder room at the rear of the home. This community has upgraded stainless steel appliances and quartz countertops making cooking and cleaning a breeze. As you head up to the second floor you are greeted with all 3 bedrooms and 2 bathrooms. The bedroom one suite impresses with double bowl vanity, walk in closet and spacious shower space. The second floor is complete with two guest bedrooms, an additional bathroom, along with laundry room. Like all homes in Waterleigh, the Ibis includes a Smart home technology package which allows you to control your home with your smart device while near or away. Your new townhome will always have fantastic curb appeal while allowing you time to do the activities your family enjoys most. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

16546 Barbours Creek Way, Winter Garden

Discover an exceptional opportunity to build a custom lakefront residence on Lot 45 in Briley Farm Phase 1B. Located at 552 Walker Street in Oakland, this approximately 0.82-acre homesite offers beautiful Lake Apopka views, direct lake frontage and generous space to create a personalized retreat exclusively with Element Home Builders. With no predetermined floor plan, buyers can collaborate with Element to create a custom design subject to applicable approvals. Briley Farm offers a peaceful setting near downtown Winter Garden, the West Orange Trail, shopping, dining and major roadways. Public water, public sewer, electricity and natural gas are available within the community. The list price is for the homesite only and does not include home construction. The purchaser must build with Element Home Builders; outside builders are not permitted.

552 Walker Street, Winter Garden

3 Beds ⋅ 3 Baths ⋅ O6433451 MLS

Welcome to this beautifully maintained home in the highly sought after Watermark at Horizon West community! This spacious two story residence offers 3 bedrooms, 2.5 bathrooms, and over 2,000 square feet of thoughtfully designed living space. The open concept floor plan is perfect for both everyday living and entertaining, featuring wood tile flooring throughout the main level, abundant natural light, and a modern kitchen complete with built in appliances, ample cabinetry, generous counter space, and a large island overlooking the living and dining areas. Upstairs, you'll find a versatile loft that makes an ideal home office, media room, or play area, along with a spacious primary suite featuring a walk in closet and an en-suite bath. Two additional bedrooms, a full bath, and an upstairs laundry room complete the second floor. Enjoy Florida living from the welcoming front porch while taking advantage of the home's rear entry two car garage and low maintenance yard. Residents of Watermark enjoy resort style amenities including a community pool, fitness center, tennis courts, playground, parks, walking trails, and beautifully maintained common areas. You’re also within close distance to restaurants and just a short drive to Disney, shopping, and everything Winter Garden and Horizon West have to offer. If you’re looking for a clean, move in ready home in a great location with a strong lifestyle, this one checks all the boxes!

14543 Golden Harbor Lane, Winter Garden

3 Beds ⋅ 3 Baths ⋅ O6433563 MLS ⋅ N/A BLDG.

Priced to sell! Great location and highly desired community! Located in the highly sought-after Hawksmoor community in Winter Garden, this beautifully maintained townhome offers exceptional value and an incredible lifestyle. The location is unbeatable, close to top-rated schools, major highways, shopping, dining, and world-class theme parks. Situated just minutes from Hamlin, you’ll enjoy easy access to one of Central Florida’s most dynamic and fast-growing areas, with a wide variety of shopping, dining, and entertainment options, including Publix, Cinépolis Luxury Cinemas, and popular restaurants. Hawksmoor offers an impressive selection of top-tier amenities, including a resort-style zero-entry pool, splash pad, shaded pavilion, clubhouse with outdoor kitchen, fitness center, scenic walking trails, yoga lawn, and multiple playgrounds and parks. The community also provides quick access to the 429 expressway, making commutes to Downtown Orlando, Walt Disney World, and other major attractions convenient and easy. The property is currently tenant occupied, with the tenant in place since October 2025, making this an excellent opportunity for investors looking for a property in a highly desirable and growing area. Priced to sell! Don’t miss the opportunity to own a townhome in one of Winter Garden’s most desirable communities. This is more than a home—it’s a lifestyle!

16306 Prairie School Drive, Winter Garden

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