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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$704,055

10163 SALT POINT DRIVE
WINTER GARDEN, Florida

5Bedroom(s)
3Bathroom(s)
17Picture(s)
3,332Sqft
This expansive two-story Douglas is optimized for gracious living, providing abundant room to grow and entertain. A flex room is situated off the foyer, followed by an open-plan layout connecting the family room, kitchen and breakfast room. On the same level is a secluded study perfect for work-from-home assignments and a bedroom ideal for overnight guests.

$520,000

14708 MASTHEAD LANDING CIRCLE
WINTER GARDEN, Florida

4Bedroom(s)
2Bathroom(s)
39Picture(s)
2,190Sqft
Gated Community with 24/7 Guards. NEW ROOF 2021 14708 Masthead Landing is located in a Beautiful, well maintained, Family friendly, Golfing and Waterfront Community.

$469,777

1438 SHERBOURNE STREET
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
22Picture(s)
1,853Sqft
This inviting 3-bedroom, 2.5-bathroom home has a loft and offers 1,853 square feet of comfortable living space. The spacious back patio faces a pond view to the north where you can enjoy the shade as the sun sets. Inside, the kitchen shines with granite countertops, white cabinets, a spacious pantry, and stylish crushed coral crown molding.rnrnThe downstairs has wood-look tile throughout.

$574,990

1391 WILLIAMS ROAD
WINTER GARDEN, Florida

4Bedroom(s)
3Bathroom(s)
23Picture(s)
2,492Sqft
Welcome to this beautiful 4 bedroom, 3.5 bath home in Waterside Community! Located in Winter Garden with “A” Rate Schools, This Well-Maintained home only 2 Years old and with Solar panels which can save you Thousands in power bills.

$585,000

8812 BISMARCK PALM DRIVE
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
29Picture(s)
1,988Sqft
Welcome to your dream home! This luxurious townhome by Toll Brothers is nestled in the exclusive community of Lakeshore, offering the pinnacle of contemporary living. With an abundance of custom-designed features and an open, light-filled floorplan, this property is the epitome of elegance and style.

$225,000

1324 EAGLE LANE
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
17Picture(s)
984Sqft
Charming one-story, 3 Bedroom / 2 Bathroom Winter Garden Townhome. Westside Townhomes features a community pool, low HOA fees and a great location. Directly off Hwy 50 with easy access to the 429, 408 and the Historic Downtown Winter Garden shops, restaurants and an award-winning Farmer’s Market.

$345,000

14501 GROVE RESORT AVENUE
WINTER GARDEN, Florida

2Bedroom(s)
2Bathroom(s)
24Picture(s)
1,265Sqft
The Grove Resort & Spa is the perfect Orlando's vacation and family resort destination for your next getaway; less than 4 miles from Disney World and other area attractions. It has a full water park, game room, fitness center, on-site Spa amenities, Living Room, Full Kitchen, beautiful furnished over sized Suites, living Room, WiFi and lake .

$729,000

9572 WATERWAY PASSAGE DRIVE
WINTER GARDEN, Florida

4Bedroom(s)
3Bathroom(s)
60Picture(s)
2,840Sqft
MOTIVATED SELLER!!!! Don't miss your chance to own this HOME!!! WELCOME HOME to this BEAUTIFUL home inside a HIGHLY SOUGHT OUT Horizon West Neighborhood! Upon entering the home you have a large FLEX space that can easily be converted to another room or an office space. This home offers the perfect blend of luxury, comfort and style.

$555,000

711 CLIMBING OAKS COURT
WINTER GARDEN, Florida

4Bedroom(s)
3Bathroom(s)
30Picture(s)
2,836Sqft
***WOWZA*** Look at that price for a home in Winter Oaks in Winter Garden! Absolutely crazy from year's past! One of the closest neighborhoods to the Historic Downtown District and the famous Plant Street lifestyle that many residents love to enjoy. Available to you is a 4 bed, 3 full bath, 2,836 sqft solid 2 story home.

$599,000

15037 BLACK SCOTER DR
WINTER GARDEN, Florida

4Bedroom(s)
3Bathroom(s)
7Picture(s)
2,710Sqft
Exceptional 4-bedroom 3-bath Winter Garden home in the beautiful Summerlake community.

$695,000

4918 WILDWOOD POINTE ROAD
WINTER GARDEN, Florida

5Bedroom(s)
3Bathroom(s)
31Picture(s)
2,868Sqft
Step inside this light and bright 5 bedroom 3.5 bath SPLIT PLAN home with enough space for everyone. Upon entering you a greeted with a oversized dining space to one side and 2 bedrooms and a full bath to the other. As you proceed you'll notice another dinning/dinette space and half bathroom just before the home opens up to the gorgeous kitchen.

$570,000

5977 PAINTED LEAF DRIVE
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
26Picture(s)
2,128Sqft
Mattamy Newer Home, The Hamilton, 2 story Craftsman, Open floor plan, 3 Bedroom with a Loft, plus Office/Flex Room First Floor. Gourmet Kitchen with 42 inch White Cabinets, Gas stove, Huge Granite Island, Stainless appliances, Primary Bedroom with Ensuite, Dual sinks. Split Bedroom plan. Screened Lanai, Tankless Water Hear, Luxury Vinyl Downstairs.

$429,900

15375 AVENUE OF THE ARBORS
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
71Picture(s)
1,751Sqft
Independence ** Great END UNIT location CLEAN CLEAN CLEAN FORMER MODEL ** BRAND NEW 9/25/23 ATTRACTIVE LAMINATE FLOORING IN THE MAIN ROOMS-Family rm, living and dining rooms ** Beautiful kitchen with granite counters, 42" cabinets, attractive backsplash and pendant lighting over the breakfast bar ** All stainless steel kitchen applicances are included ** Full laundry room with white cabinetry and

$431,740

12620 CHARMED DRIVE
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
25Picture(s)
1,567Sqft
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.

$733,606

18345 OLIVER TWIST WAY
WINTER GARDEN, Florida

4Bedroom(s)
3Bathroom(s)
27Picture(s)
3,327Sqft
Under Construction. Located in our Waterleigh Community, The Sea Cliff home is a beautiful 4 bedroom 3.5 bath home with a spacious entry featuring tray ceilings. Formal dining room or possible flex space for entertaining. Gourmet kitchen features stainless steel appliances, stone counter tops, and glass tile back splash, as well a convenient butler’s pantry.

$424,999

1925 AMERICUS MINOR DRIVE
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
27Picture(s)
1,560Sqft
Welcome to your serene oasis! This beautiful 3-bedroom, 2-bathroom home boasts over 1,500 square feet of comfortable living space. Nestled on a picturesque lot with tranquil water and conservation views, this property offers a retreat from the everyday hustle and bustle.

$549,999

16025 PEBBLE BLUFF LOOP
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
55Picture(s)
2,220Sqft
Back on the market due to buyer unable to get financing! Built in 2018 this 3/2.5 with Flex Room in Waterleigh Is move-in ready! The 2-story home features Solar Panels, an open concept, and is located directly across the street from a park and playground. The Bellake floor plan by D.R.

$1,299,999

14838 SPEER LAKE DRIVE
WINTER GARDEN, Florida

4Bedroom(s)
3Bathroom(s)
61Picture(s)
3,056Sqft
Gorgeous lakefront home with private boat dock and lift! Enjoy the sunrise and the Disney fireworks right from your backyard! This remarkable 4 bedroom, 3.5 bath home is perfectly situated on Lake Speer in Winter Garden. Located on one of the most desirable streets in Independence, this home provides lakefront living with all the luxuries of this popular neighborhood.

$450,000

10103 MEMOIR AVENUE
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
30Picture(s)
1,657Sqft
Take advantage of your opportunity to own this beautiful townhome in Storey Grove, located in the highly sought-after Horizon West area. This elegant designer townhome is a two-story with three bedrooms, two and a half bathrooms, and a two-car garage.

$505,880

4730 ABBEYWOOD ALLEY
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
1Picture(s)
1,678Sqft
Pre-Construction. To be built. Brand new, energy-efficient home available by Feb 2024! An open, spacious kitchen overlooks the great room and dining area making it perfect for entertaining friends and family. The second-floor loft can be configured as a home office or a play area. Visit the Silverleaf Bungalow community and explore new single-family homes for sale in Winter Garden, FL.

$1,950,000

7573 GREEN MOUNTAIN WAY
WINTER GARDEN, Florida

4Bedroom(s)
3Bathroom(s)
70Picture(s)
3,388Sqft
Step into this extraordinary LAKEFRONT haven, nestled on a sprawling 1.26-acre expanse along the pristine shores of Lake Hancock, renowned as one of Central Florida's most coveted ski lakes. As you traverse through this enchanting abode, emotions swell within you, igniting a sense of wonder and delight that can only be found in a place like this.

$795,000

707 TANGELO COURT
WINTER GARDEN, Florida

4Bedroom(s)
3Bathroom(s)
25Picture(s)
2,400Sqft
This remodeled 4/3 located in the Golf Cart District of Historic Downtown Winter Garden boasts all the upgrades of a turn-key home. NEW ROOF, NEW PLUMBING, UPDATED ELECTRIC with partial new wiring, NEW STUCCO with NEW INTERIOR & EXTERIOR PAINT.

$596,755

17958 HITHER HILLS CIRCLE
WINTER GARDEN, Florida

4Bedroom(s)
3Bathroom(s)
28Picture(s)
2,361Sqft
Under Construction. Lake Apopka Sound presents the Destin. This spacious all concrete block construction single-family home features 4 bedrooms and 3 baths. As you enter the foyer, you are greeted with two bedrooms and a full bathroom. The well-appointed kitchen overlooks the dining room and features an island with bar seating, beautiful granite countertops and stainless steel appliances.

$625,000

909 MCKINNON SQUARE
WINTER GARDEN, Florida

3Bedroom(s)
2Bathroom(s)
27Picture(s)
1,772Sqft
Welcome Home to this Modern Bungalow located in the highly Desired McKinnon Square at Oakland Park.
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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.