Search All Winter Garden Real Estate

The cozy community of Winter Garden, Florida, is an excellent place to buy a home, just fifteen miles from Orlando. Roughly forty thousand people reside in the city and enjoy its long list of advantageous features, services, and amenities. Though near Orlando and all of its hustle and bustle, Winter Garden has a relaxed, laid-back vibe, and the abundance of natural beauty contributes to its tranquility. Other appealing qualities include a charming historic downtown that is listed on the National Register of Historic Places. Moreover, Downtown Winter Garden encompasses a theatre, several museums, small shops, restaurants, and cafes.

Winter Garden residents also enjoy quick and convenient access to significant transportation routes, including the Western Beltway, County Road 545, and County Road 535. The area also offers recreation and leisure opportunities in multiple lovely parks, including Oakland Nature Preserve, Chapin Station, and one of the region's largest farmer's markets. These and other destination opportunities include scenic hiking and biking trails, wide-open green spaces, sports courts, playgrounds, and similar features. All of these spectacular options for recreation, entertainment, shopping, and dining contribute to the enduring appeal of Winter Garden real estate.

Real estate in Winter Garden includes residences of varying floor plans, including attached and detached homes. While these homes exist on a spectrum, the average Winter Garden home offers around three thousand five hundred square feet of living space. Homes for sale in Winter Garden are of varying architectural styles, including Modern, Traditional, and Mediterranean. Winter Garden properties are also of varying ages so you can just as easily find a historic home as new construction. We will happily answer all of your questions, so if you would like to learn more about currently listed properties in Winter Garden, Florida, please contact us as soon as it is convenient.

Our website features the best Winter Garden real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes.

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Newest Winter Garden Homes & Condos for Sale

16328 Wind View Lane, Winter Garden image

16328 Wind View Lane, Winter Garden $949,900

LUXURY POOL HOME on Oversized Home Site near DISNEY! PRIVATE Corner Lot in Popular Phase 1 of Waterleigh. This Kallan POOL HOME has 4 Bedrooms, 4.5 Baths, FLEX Room, Lo...

4 Beds
4.5 Baths
Waterleigh Ph 1b SubDv.
34787 Zip Code

16613 Point Rock Drive, Winter Garden image

16613 Point Rock Drive, Winter Garden $510,000

Motivated Seller. Two years old house in the nice Waterleigh community. Close to Disney and 429 express way. Waterleigh is a resort-style living community. This is th...

3 Beds
2 Baths
Waterleigh Ph 4a SubDv.
34787 Zip Code

9562 Meadow Hunt Way, Winter Garden image

9562 Meadow Hunt Way, Winter Garden $1,090,000

Carpet free! This stunning 4-bedroom, 4-bathroom home is located in the highly sought-after Watermark community in Winter Garden. Just a short walk to the clubhouse, gas...

4 Beds
3.5 Baths
Watermark SubDv.
34787 Zip Code

Winter Garden $790,000

The house is vacant, The house has a large backyard, It towards a retention pond and a lake. Water leigh is located in Winter Garden/Horizon West area and has a Lakefront...

4 Beds
3.5 Baths
Waterleigh Ph 3b 3c & 3d SubDv.
34787 Zip Code

16711 Otterchase Lane, Winter Garden image

16711 Otterchase Lane, Winter Garden $1,250,000

Welcome home to this pristine property nestled behind the charming gated entrance of Waterside on Johns Lake. You will be greeted by stunning curb appeal, featuring a Med...

6 Beds
4.5 Baths
Waterside/Johns Lk-Ph 1 SubDv.
34787 Zip Code

501 N Dillard Street, Winter Garden image

501 N Dillard Street, Winter Garden $1,250,000

Welcome to this stunning 4-bedroom, 3.5-bathroom residence that beautifully blends classic charm with modern luxury. Built in 2020 and nestled in the heart of Winter Gard...

4 Beds
3.5 Baths
Dillard Pointe SubDv.
34787 Zip Code

12863 Daughtery Drive, Winter Garden image

12863 Daughtery Drive, Winter Garden $535,000

The Perfect Home with an Outdoor Kitchen for Entertaining in a Desirable Location by the Winter Garden Village! Welcome to this beautiful single-story home with 4 bedr...

4 Beds
2 Baths
Grovehurst SubDv.
34787 Zip Code

14090 Lochend Way, Winter Garden — Toll Brothers $899,995

Move-in ready Toll Brothers 5 bedroom-4 bath home in beautiful Winter Garden. Only a few minutes away from Disney. This Grenada floor plan has over 3256 of living square...

5 Beds
4 Baths
Westhaven At Ovation 111/89 Lot 76 SubDv.
34787 Zip Code

164 Windtree Lane Unit 201, Winter Garden image

164 Windtree Lane Unit 201, Winter Garden — U $220,000

Location, Location, Location! Welcome to Windtree, renowned for its lush, well-maintained landscaping. Nestled in the charming community of Winter Garden, this second-fl...

2 Beds
2 Baths
Windtree Gardens Condo Ph 06 SubDv.
34787 Zip Code

15129 Sunrise Grove Court, Winter Garden image

15129 Sunrise Grove Court, Winter Garden — 15129 $495,780

Welcome to your new home! A corner unit townhome with an open green space/park in the back! As soon as you step inside, you'll notice the love and care that this home has...

3 Beds
2.5 Baths
Hickory Hammock Ph 2b SubDv.
34787 Zip Code

13613 Larsen Lane, Winter Garden $850,000

Welcome to the luxury living! Conveniently located in gated Glynwood II/Stone Crest you will find this charming home. Featuring 4 bedrooms, 4 baths, formal living and din...

4 Beds
4 Baths
Glynwood Ph 2 SubDv.
34787 Zip Code

704 Tangelo Court, Winter Garden $630,000

Welcome to this beautifully upgraded 3 bed, 2 bath ranch-style home, perfectly situated in the heart of historic downtown Winter Garden on a cul-de-sac. This charming one...

3 Beds
2 Baths
Valencia Shores SubDv.
34787 Zip Code

14384 Wabasso Loop, Winter Garden $849,000

Discover the charm and convenience of this stunning 5-bedroom, 3-bathroom house! Gated Community, 3,562 SqFt of open-concept design, with airy spaces and large windows eq...

5 Beds
3 Baths
Tilden Place SubDv.
34787 Zip Code

1226 Scarlet Oak Loop, Winter Garden image

1226 Scarlet Oak Loop, Winter Garden — - $355,000

Discover your new retreat in this delightful 3-bedroom, 2-bathroom townhome nestled within a gated community. The interior has been freshly painted and boasts new carpet ...

3 Beds
2.5 Baths
Villas/Tucker Oaks SubDv.
34787 Zip Code

1627 E Spring Ridge Circle, Winter Garden image

1627 E Spring Ridge Circle, Winter Garden $465,000

The WINTER GARDEN Golf Cart District welcomes a new home to market! This 3-bedroom, 2-bath FENCED home sits on nearly a quarter of an ACRE (.23) in one of the most sought...

3 Beds
2 Baths
Crown Point Spgs SubDv.
34787 Zip Code

6826 Point Hancock Drive, Winter Garden image

6826 Point Hancock Drive, Winter Garden $485,000

Independence ** Great one story living and floor plan & private fenced backyard ** Beautiful kitchen with NEW WHITE QUARTZ counters (Calcutta Quartzite), espresso cabinet...

3 Beds
2 Baths
Signature Lakes, Independence SubDv.
34787 Zip Code

2636 Bobcat Chase Boulevard, Oakland image

2636 Bobcat Chase Boulevard, Oakland $725,000

Prepare to be captivated by this stunning 4-bedroom, 2.5-bathroom POOL home located in the charming town of Oakland, Florida. Nestled in an unbeatable location, the commu...

4 Beds
2.5 Baths
Longleaf At Oakland SubDv.
34787 Zip Code

1817 Seatonham Street, Winter Garden image

1817 Seatonham Street, Winter Garden $450,000

Discover this move in ready, one-owner home featuring 1,828 heated square feet and an oversized 2-car garage. With four bedrooms and three baths, plus a convenient insid...

4 Beds
2.5 Baths
Stone Creek SubDv.
34787 Zip Code

10527 Spring Arbor Lane, Winter Garden image

10527 Spring Arbor Lane, Winter Garden — 10527 $465,000

One or more photo(s) has been virtually staged. Better than new! This stunning 3-bedroom, 2.5-bathroom townhome offers modern living with thoughtful design. The spacious ...

3 Beds
2.5 Baths
Winding Bay Preserve SubDv.
34787 Zip Code

9078 Wading Walk Lane, Winter Garden image

9078 Wading Walk Lane, Winter Garden — 9078 $485,000

Must see Move-in Ready Home!! Impressive Corner Townhome with the largest floor plan located in the highly desired community of Waterleigh. Walk through the front porch a...

3 Beds
2.5 Baths
Waterleigh Ph 3b 3c & 3d SubDv.
34787 Zip Code

2261 Standing Rock Circle, Oakland image

2261 Standing Rock Circle, Oakland $464,999

Check out this charming two-story Chandler Floor Plan from Meritage Homes, perfect for families who enjoy hosting guests of all ages! The open, spacious kitchen overlooks...

3 Beds
2.5 Baths
Oakland Trails SubDv.
34787 Zip Code

14912 Gaulberry Run, Winter Garden image

14912 Gaulberry Run, Winter Garden $785,000

Welcome to your dream home in Winter Garden’s highly sought-after Independence community! This stunning two-story property sits on a beautifully landscaped corner lot, of...

5 Beds
3 Baths
Signature Lks-Pcl 01d Ph 02 SubDv.
34787 Zip Code

15167 Shonan Gold Drive, Winter Garden image

15167 Shonan Gold Drive, Winter Garden $1,150,000

Discover this exquisite 6-bedroom, 3.5-bath home in the prestigious Overlook at Hamlin community nestled in booming Horizon West. With fresh, brand-new paint inside and o...

6 Beds
3.5 Baths
Overlook 2/Hamlin Ph 3 & 4 SubDv.
34787 Zip Code

13633 Daniels Landing Circle, Winter Garden image

13633 Daniels Landing Circle, Winter Garden — N/A $359,999

Do not miss out on this unique opportunity to see this property within the gated community of Daniels Landing! Steps from your front door is an HOA maintained fitness cen...

3 Beds
2.5 Baths
Daniels Landing A-J SubDv.
34787 Zip Code

15102 Stuttgart Alley, Winter Garden image

15102 Stuttgart Alley, Winter Garden $550,000

Emerson model by Meritage Homes. 4 bedroom 2.5 bathroom 2,204 sq ft home. First floor open plan family room, dining room and kitchen, half bath. 42" cabinets with stainle...