Homes for Sale in Winter Garden

Whether you’re looking to move-up or downsize, Winter Garden has the perfect living space for you. Winter Garden’s active downtown, with an award-winning farmer’s market, bike trail, and brewery, has been a favorite of locals for years. Buyer’s can choose homes located next to the 22-mile West Orange trail, countless restaurants in the historic downtown or in new communities of the surrounding suburbs.

As Winter Garden’s top Buyer’s Agent, the Erica Diaz Team has the experience to find what you’re looking for; find your Winter Garden Home using the filter below, or explore what else Winter Garden has to offer.

Sort Option
  • Listing ID
  • Built up Area
  • Price
  • Pictures
  • Add date
  • Featured
Grid
List
Map

$1,090,000

1453 UNION CLUB DRIVE
WINTER GARDEN, Florida

5Bedroom(s)
4Bathroom(s)
69Picture(s)
2,691Sqft
Welcome home, nestled in the heart of Winter Garden’s Oakland Park community! This captivating residence offers 5 bedrooms, 4 bathrooms, a loft, balcony, and heated saltwater POOL! Prepare to be amazed by the extensive upgrades that have been meticulously incorporated into this remarkable property.

$699,000

741 CATERPILLAR RUN
WINTER GARDEN, Florida

7Bedroom(s)
4Bathroom(s)
65Picture(s)
4,700Sqft
Price reduction !!!!new eproxy garage floor new paint at the kitchen a. Energy-efficient gorgeous home is a beautiful upscale 2-story home with 7 bedrooms , 4 bathrooms including owner's suites and one guest room downstairs, formal dining room, living room, family room that adjoins a breakfast nook/cafe with Kitchen bar and island and oversized covered lanai.

$599,000

16012 MICELLI DRIVE
WINTER GARDEN, Florida

4Bedroom(s)
3Bathroom(s)
37Picture(s)
2,428Sqft
Nestled in the picturesque and family-friendly community of Winding Bay, Winter Garden, this exquisite 4-bedroom, 3-bathroom home is a true gem. With its prime location, spacious interior, and a host of delightful features, this property is a dream come true for those seeking the perfect blend of comfort, style, and convenience.

$1,200,000

16760 RUSTY ANCHOR ROAD
WINTER GARDEN, Florida

5Bedroom(s)
4Bathroom(s)
49Picture(s)
3,615Sqft
Step into a world of elegance and sustainability as you discover this captivating SOLAR POWERED - POOL home, where comfort meets LUXURY in perfect harmony, the SOLAR PANELS OFFSETS 100% of the electric bill. Nestled within the gorgeous GATED and WATERFRONT community of Waterside in Winter Garden, this residence shines as a true gem.

$899,999

15734 SWEET LEMON WAY
WINTER GARDEN, Florida

5Bedroom(s)
4Bathroom(s)
53Picture(s)
3,635Sqft
Captivating solar-powered 5-bedroom, 4 and a half bathroom pool home nestled in the charming Highlands at Sumerlake Groves Neighborhood. This exceptional residence boasts an impeccably designed open concept that exudes both elegance and comfort.

$235,000


WINTER GARDEN, Florida

3Bedroom(s)
1Bathroom(s)
15Picture(s)
925Sqft
Ideal Location! Steps away from downtown Winter Garden, offering easy access to shops, top-notch restaurants, the lively Farmer's Market, the scenic West Orange Trail, and the local library. Discover this charming 3-bedroom, 1.5-bathroom home boasting over 900 sq.ft. of well-designed living space and the convenience of a private master bathroom.

$419,900

531 9TH STREET
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
16Picture(s)
1,469Sqft
One or more photo(s) has been virtually staged. Be the FIRST OWNER of this beautiful NEW construction 3 bedroom/2.5 bath property in the heart of Winter Garden. Conveniently located close to the Downtown Winter Garden, Maxey Elementary, and the 91.

$560,000

9345 JAYWOOD ROAD
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
41Picture(s)
2,027Sqft
Welcome to your new home in the picturesque neighborhood of Winter Garden, Florida. This inviting residence boasts 3 spacious bedrooms and 2.5 modern baths, offering a perfect blend of comfort, style, and functionality.rnrnUpon arrival, you'll be captivated by the charming curb appeal and well-maintained landscaping that sets the tone for what lies within.

$1,050,000

9384 BRADLEIGH DRIVE
WINTER GARDEN, Florida

6Bedroom(s)
4Bathroom(s)
49Picture(s)
3,866Sqft
Experience true peace and tranquility with a relaxing view and no rear neighbors! Whether you prefer a quiet read by the pool or fireworks at night, this sublime home nestled within desirable Latham Park in Winter Garden has everything to offer, located less than two miles from Walt Disney World and within a short drive of new shops and restaurants.

$574,000

11115 FOLKLORE STREET
WINTER GARDEN, Florida

4Bedroom(s)
3Bathroom(s)
32Picture(s)
2,475Sqft
One or more photo(s) has been virtually staged. This inviting home offers a natural color palette and fresh interior paint throughout, creating a cozy and welcoming atmosphere. The kitchen is equipped with a center island and a stylish backsplash, making it the perfect spot for cooking and entertaining.

$540,000

16536 SEA GLASS STREET
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
25Picture(s)
2,014Sqft
This beautiful house appointed in the highly desirable Waterleigh lake filled community really has it all. This perfect home was build in 2021. This Home is in Excellent shape, this home a 3 bedrooms, 2.5 bathrooms. House features, tile thought the first floor, open floor plan, a gorgeous modern kitchen with back splash, granite countertops in the kitchen and bathrooms.

$698,000

15160 BOOK CLUB ROAD
WINTER GARDEN, Florida

5Bedroom(s)
3Bathroom(s)
52Picture(s)
3,295Sqft
Amazing Floor plan and great location, stunning two-story, offers 5 bed, 3 Baths home with 3 car garage, full of upgrades. NO CARPET AT ALL! FRESH INTERIOR PAINTING! Wood-plank tile flooring in all common areas, nice granite countertops, energy-efficient appliances, Gourmet Kitchen with 42" cabinets, and much more.

$1,195,000

4973 WILDWOOD POINTE ROAD
WINTER GARDEN, Florida

6Bedroom(s)
5Bathroom(s)
53Picture(s)
4,548Sqft
This spectacular home boasts over 4500 square feet under air with 6 bedrooms, 5.5 baths, a bonus room, a home theater, plus a dedicated office. Having only been used as a vacation home, the home shows like new. Interior features a custom coffered ceiling in the dining room along with a tray ceiling in the living room.

$539,400

10145 BEDTIME STORY DRIVE
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
27Picture(s)
2,124Sqft
This immaculate two-story home is a family-friendly haven located in highly desirable Storey Grove. The first floor offers a half bath and a flex space that is full of possibilities, a modern kitchen, with stainless steel appliances, quartz countertops and ceramic tile floors, that connects in an open-plan layout to an inviting nook and a family room ideal for entertaining.

$755,000

1479 SELBYDON WAY
WINTER GARDEN, Florida

6Bedroom(s)
3Bathroom(s)
22Picture(s)
3,661Sqft
Location, Luxury, Lifestyle directly on the 9th hole! This 6-bed, 3-bath pool home is nestled in Stoneybrook West, a highly sought after golf community with a security person gated entrance. The seller is motivated and accepting offers. This large home boasts a spacious and thoughtfully designed interior, with an open floor plan.

$769,999

320 MAIN STREET
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
33Picture(s)
1,850Sqft
NOW OFFERING $10K TOWARDS BUYERS CLOSING COST - READY TO CLOSE. Welcome to one of downtown Winter Gardens only new construction homes within the golf cart district. This home is walkable to Plant Street, West Orange Trail and the Farmers Market held every Saturday. Enjoy your 240 s.f. front porch that can fit plenty of furniture and family members.

$475,000

1220 BEULAH ROAD
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
22Picture(s)
1,658Sqft
Welcome Home! You do not want to miss your chance to own this meticulously maintained three bedroom two bathroom home on .46 acres in beautiful Winter Garden. This unique property also has rear access from Taratine Drive perfect for parking the boat and RV. Upon entry you will be amazed by the openness of this split floor plan.

$670,000

702 VALENCIA SHORES DRIVE
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
38Picture(s)
1,990Sqft
Welcome to your dream home in the heart of downtown Winter Garden, nestled within the coveted golf cart district! This beautiful pool home is located in the charming Valencia Shores community. This 3-bedroom 2.5-bathroom one story home sits on a 1/3 acre lot at the end of a Cul-De-Sac. The home has been extremely well maintained.

$460,000

14501 GROVE RESORT AVENUE
WINTER GARDEN, Florida

2Bedroom(s)
2Bathroom(s)
33Picture(s)
1,265Sqft
Great Palm Unit fully furnished and equipped two bedrooms, two bathrooms at The Grove Resort and Spa. This spacious unit is located in the Disney Vacation Homes area. The Grove Resort is an oasis of tranquility surrounded by nature in the beautiful Lake Austin conservation.

$1,150,000

15112 CANOE PL
WINTER GARDEN, Florida

5Bedroom(s)
4Bathroom(s)
90Picture(s)
4,089Sqft
WELCOME HOME TO LAKESHORE PRESERVE! This STUNNING, 5 Bedroom, 4.5 Bath TOLL BROTHERS-built, Gardenia Model, is located in one of Horizon West’s Newest and Most Sought-After Communities.

$529,900

12121 BRACCO STREET
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
43Picture(s)
1,668Sqft
Want a Ready to Move house? More than $12K in UPGRADES make this house very modern and comfortable. Spacious open-concept floor plan with abundant natural light, gourmet kitchen with high-end appliances and sleek countertops! Proximity to parks, golf courses, and recreational facilities for outdoor enthusiasts.

$1,680,000

15113 JOHNS LAKE POINTE BOULEVARD
WINTER GARDEN, Florida

5Bedroom(s)
4Bathroom(s)
100Picture(s)
5,501Sqft
This is a fantastic and majestic home with an excellent location in Johns Lake Winter Garden. It offers 5 bedrooms and over 5,000 square feet of living space, along with a 3 car garage. The front elevation features extensive stone accents, and there are numerous upgraded features throughout the house. This beautiful home must be seen in person to truly appreciate its beauty.

$674,376

17780 ADRIFT ROAD
WINTER GARDEN, Florida

4Bedroom(s)
3Bathroom(s)
30Picture(s)
2,113Sqft
Under Construction. Waterleigh presents the Bellmore. This all concrete block constructed, one-story layout features 4 bedrooms and 3 bathrooms. A beautiful patio welcomes you to a home that optimizes living space with an open concept kitchen overlooking the living area, dining room, and outdoor lanai.

$839,900

2420 DAHLGREN WAY
WINTER GARDEN, Florida

5Bedroom(s)
3Bathroom(s)
40Picture(s)
3,133Sqft
Here's your opportunity to own a spacious pool home in the Winter Garden area in the highly sought after Bronson's Landing. A quiet and double gated community with easy access to 429, the hospital, Winter Garden Village and downtown Winter Garden. The pool faces West so you can enjoy the magical sunsets that Winter Garden is famous for. This property is located in a very desirable school zone.
364 Results returned.Per Page

Who’s Your Winter Garden Buyer’s Agent?

Every home shopper should have a Buyer’s Agent – it’s free to the buyer. Agents at the Erica Diaz Team know Winter Garden best! They know how to help you negotiate a better deal, and close faster than the average Winter Garden Realtor. Ask us about the local neighborhoods, we’ll know where to find the best homes for your goals in each price range.