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.

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$430,000

14501 GROVE RESORT AVE AVENUE
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
6Picture(s)
1,396Sqft
Great commissions and easy to show!! Come One, Come All! This is perfect for a family or anyone looking to use as an investment home. This beautiful home comes FULLY FURNISHED with really thought-out details to make you feel right at home.

$697,000

15062 LAKE BESSIE LOOP
WINTER GARDEN, Florida

5Bedroom(s)
3Bathroom(s)
37Picture(s)
3,099Sqft
Welcome to your dream home in the Lakeside/Hamlin neighborhood, where luxury meets living. Built in 2023, this stunning 5-bedroom, 3.5-bathroom residence offers an array of amenities. The open concept floor living and dining area seamlessly flows into the gourmet kitchen complete with an island, breakfast bar, eye-catching plenty of space cabinetry, and state-of-the-art stainless-steel appliances.

$733,995

9463 EMERALD BERRY DRIVE
WINTER GARDEN, Florida

4Bedroom(s)
3Bathroom(s)
8Picture(s)
2,923Sqft
Pre-Construction. To be built. Summerlake Reserve is an intimate community of 41 homesites, nestled in a tranquil setting, with the convenience of being close to everything Horizon West has to offer; A rated schools, shopping, dining, & entertainment! The Baldwin - A home that harmonizes with your every need - space, style, and versatility - is the epitome of good living.

$845,441

18416 OLIVER TWIST WAY
WINTER GARDEN, Florida

4Bedroom(s)
3Bathroom(s)
41Picture(s)
2,866Sqft
Under Construction. Amazing Floor plan and great location inside our Waterleigh community! This Brand new Cresswell home will be completed soon. Open bright design perfect for entertaining and everyday enjoyment.

$545,990

11151 SOUND SHORE DRIVE
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
35Picture(s)
2,027Sqft
Under Construction. The CORDALE, in the Waterleigh community, is great for entertaining with the cafe just off the kitchen for casual dining. The master bedroom conveniently located on the first floor with a bathroom that features double sink with granite tops.

$359,000

14501 GROVE RESORT AVENUE
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
58Picture(s)
1,396Sqft
Discover your dream investment opportunity and retreat in the heart of Orlando at the Grove Resort! This exquisite condo hotel unit on the 5th floor offers 3 expansive bedrooms and 2 modern bathrooms and is surrounded by serene tree-lined vistas for a truly relaxing stay.

$779,000

351 FLORAL DRIVE
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
25Picture(s)
1,722Sqft
Welcome to a prime corner lot property in Historic Downtown Winter Garden. While the home has been in the seller's family for three generations, it was fully remodeled in 2019 and updated again in 2023 with Smart Home Technology, A/C and irrigation. This home sits on 1/3 acre in the highly coveted North Side of Downtown.

$930,995

14090 LOCHEND WAY
WINTER GARDEN, Florida

5Bedroom(s)
4Bathroom(s)
3Picture(s)
3,256Sqft
Under Construction. Brand New home. Move-in late spring, early summer Five bedroom 4 bath home. Primary suite down stairs. Two story foyer with open stair railing on first and second floor . Other features include over size master suite, gourmet kitchen, large loft area, extended lanai and vaulted ceilings.

$1,150,000

7808 FREESTYLE LANE
WINTER GARDEN, Florida

4Bedroom(s)
2Bathroom(s)
20Picture(s)
2,572Sqft
Welcome to this stunning home located in the gated community of Isles of Lake Hancock. The beautiful waterski community offers the perfect opportunity to indulge in waterskiing on Lake Hancock. Residents can make use of the community boat ramp and also have access to a professional waterski school.

$539,000

14501 GROVE RESORT AVENUE
WINTER GARDEN, Florida

2Bedroom(s)
2Bathroom(s)
6Picture(s)
1,265Sqft
Great commissions and easy to show!! Come One, Come All! This is perfect for a family or anyone looking to use as an investment home. This beautiful home comes with really thought-out details to make you feel right at home. The Community also offers TONS of recreational items to choose from: You can choose from relaxing at the spa, working out in one or both of the two fitness centers provided.

$312,000

14501 GROVE RESORT AVENUE
WINTER GARDEN, Florida

2Bedroom(s)
2Bathroom(s)
7Picture(s)
1,265Sqft
Beautiful unit at the desired Grove Resort and Spa in the constant growing Winter Garden. Water Park, dual water slides, pools, splash pads,boat dock with paddle boats and canoes available for rent, mini golf, fitness center. The Grove is fully equipped with restaurant dinning, bar, coffee bar, sandwich shop and convenience store. Conveniently located 3 miles from Walt Disney World.

$1,695,000

7507 GREEN MOUNTAIN WAY
WINTER GARDEN, Florida

5Bedroom(s)
3Bathroom(s)
74Picture(s)
4,096Sqft
One or more photos have been virtually staged. Welcome to luxury living in the heart of Hamlin in Winter Garden. Near beautiful Lake Hancock in the sought-after community of Overlook at Hamlin, the Encanto floorplan by Taylor Morrison has stunning architecture.

$470,000

11139 HANLON TERRACE ALLEY
WINTER GARDEN, Florida

4Bedroom(s)
3Bathroom(s)
27Picture(s)
2,037Sqft
Immerse yourself in contemporary elegance with this distinguished 4-bedroom, 3-bathroom townhome nestled in Winter Garden's coveted Winding Bay Preserve. Meticulously designed, this residence boasts an open-concept layout, accentuating a seamless blend of modern aesthetics and practical functionality.

$339,900

13801 GOLDEN RUSSET DRIVE
WINTER GARDEN, Florida

2Bedroom(s)
2Bathroom(s)
3Picture(s)
1,604Sqft
***INCREDIBLE WINTER GARDEN LOCATION / NEED I SAY... SCHOOLS, SCHOOLS, SCHOOLS *** This well priced beautiful townhome is located in the best area of Winter Garden. Minutes to great shopping at Winter Garden Village, and Downtown Historic Winter Garden. Close and convenient to the turnpike, 429, and major highways.

$799,000


WINTER GARDEN, Florida

4Bedroom(s)
3Bathroom(s)
23Picture(s)
2,840Sqft
The house has a large backyard, It towards a retention pond and a lake. Waterleigh is located in Winter Garden/Horizon West area and has a Lakefront Clubhouse with the best resort-style amenities including pool, splash pad, miniature golf course, beach volleyball, fitness centers, BBQ grills, picnic areas, water-view recreational trails and a bark park for pets.

$1,375,000

16189 JOHNS LAKE OVERLOOK DRIVE
WINTER GARDEN, Florida

5Bedroom(s)
4Bathroom(s)
71Picture(s)
4,479Sqft
NEWLY PRICED!!! Welcome to John's Lake Overlook Drive and experience a luxurious Florida lifestyle in the Gated-Community of Hickory Hammock with this spectacular Screened-In POOL & POND-VIEW residence built in 2015.

$675,000

3318 CURRENT AVENUE
WINTER GARDEN, Florida

5Bedroom(s)
3Bathroom(s)
21Picture(s)
2,916Sqft
Step into the captivating charm of Winter Garden with this exquisite property, now temptingly priced at $675,000 for a swift sale. Located at 3318 Current Ave, this inviting home spans 2,916 sq ft and features five spacious bedrooms and three full bathrooms, offering ample space for family life and entertaining.

$3,575,000

900 PLANT STREET
WINTER GARDEN, Florida

7Bedroom(s)
6Bathroom(s)
74Picture(s)
7,704Sqft
Welcome to 900 W Plant St! A once in a lifetime, privately gated, 1.6 acre paradise that is truly a rare find! Custom built, offering the ultimate multi-generational living, or endless opportunites for work, live and play - the lifestlye offered here is second to none.

$399,900

14501 GROVE RESORT AVENUE
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
6Picture(s)
1,396Sqft
Great commissions and easy to show!! Come One, Come All! This is perfect for a family or anyone looking to use as an investment home. This beautiful home comes FULLY FURNISHED with really thought-out details to make you feel right at home.

$1,945,000

7128 TICKLEGRASS STREET
WINTER GARDEN, Florida

6Bedroom(s)
5Bathroom(s)
39Picture(s)
4,878Sqft
Priced to sell! LAKEFRONT (Ski Lake) 3 car garage home in Independence (Hamlin area). Live two exits from Disney. Lake Hancock is a spring-fed lake that boasts over 480 acres. *Private lake for residents only * Oversized lot with breathtaking views from the moment you walk through the door.

$230,000

14200 AVALON ROAD
WINTER GARDEN, Florida

2Bedroom(s)
2Bathroom(s)
40Picture(s)
1,203Sqft
This marvelous condominium is in search of its new owner! Situated within the picturesque Palisades Resort Community, this spacious condo unit is ideal for short-term or long-term rental market. Boasting 2 bedrooms and 2 bathrooms, the residence offers remarkable features like a split bedroom floorplan and tile flooring in the kitchen and bathrooms, along with an expansive dining/living area.

$369,000

14501 GROVE RESORT AVENUE
WINTER GARDEN, Florida

3Bedroom(s)
3Bathroom(s)
35Picture(s)
1,544Sqft
Welcome to paradise at The Grove Resort in the beautiful Winter Garden, Florida. This spacious 3-bedroom, 3-bathroom corner unit on the 1st floor, boasting an impressive 1544 square feet of living space, offers the epitome of resort-style living. This property is a dream come true with a prime location, incredible amenities, and proximity to Disney World.

$787,101

18410 OLIVER TWIST WAY
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.

$585,000

16721 ALPACA ALLEY
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
25Picture(s)
2,014Sqft
Welcome to Waterleigh, an esteemed residential enclave within the sought-after Horizon West community. Presenting the Cordale model, strategically positioned on a prime parcel within Waterleigh, this residence exemplifies refined living with its 3 bedrooms and 2.5 baths.
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Erica Diaz - Winter Garden Realtor

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.