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.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

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Newest Winter Garden Homes & Condos for Sale

12642 Dallington Terrace, Winter Garden image

12642 Dallington Terrace, Winter Garden $685,000

Welcome to your dream home! This spacious and open San Remo floor plan allows for an abundance of natural light throughout the house. It sits on an extra large corner lot...

4 Beds
4 Baths
Foxcrest A-N & P SubDv.
34787 Zip Code

8857 Sonoma Coast Drive, Winter Garden image

8857 Sonoma Coast Drive, Winter Garden $633,616

Under Construction. Located in our Waterleigh community, the Kenton is a spacious two story open floor plan with 4 bedrooms, 3 baths, 2 car garage. This home invites you ...

4 Beds
3 Baths
Waterleigh SubDv.
34787 Zip Code

488 Regal Downs Circle, Winter Garden image

488 Regal Downs Circle, Winter Garden $329,000

One or more photo(s) has been virtually staged. This is the one you’ve been looking for! Clean and move in ready! Freshly painted inside and out and brand new carpet from...

4 Beds
2 Baths
Regal Pointe Ph 01 43/129 SubDv.
34787 Zip Code

15500 Fountain Cove Court, Winter Garden image

15500 Fountain Cove Court, Winter Garden — Dh Horton $585,000

Gorgeous cul-de-sac corner home with premium lot. It has been professionally decorated. Lawn care and outside maintenance also are included.You will love spacious livin...

4 Beds
3 Baths
Waterleigh Ph 1a SubDv.
34787 Zip Code

7715 Summerlake Pointe Boulevard, Winter Garden image

7715 Summerlake Pointe Boulevard, Winter Garden $1,299,000

PERFECT LAKEFRONT HOME FOR BOATERS AND WATER SKIERS!Custom built 2014 Solar Paneled home on a premier elevated lot in the Summerlake/Hamlin community overlooking beautifu...

3 Beds
2 Baths
Summerlake Pd Ph 1b SubDv.
34787 Zip Code

14458 Prunningwood Place, Winter Garden image

14458 Prunningwood Place, Winter Garden — N/A $289,000

You can choose to live near all that Orlando has to offer - world famous theme parks, shopping and entertainment. This beautiful townhouse is located in the desired subdi...

2 Beds
2 Baths
Signature Lakes SubDv.
34787 Zip Code

9038 Sonoma Coast Drive, Winter Garden image

9038 Sonoma Coast Drive, Winter Garden $770,121

Under Construction. The NORTH HAVEN is a beautiful 5 bedroom 3.5 bath home and 3 car garage home. With a sense of entry with a formal dining room just off the wide foyer ...

5 Beds
3 Baths
Waterleigh SubDv.
34787 Zip Code

8661 Flagship Alley, Winter Garden image

8661 Flagship Alley, Winter Garden $474,495

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 convenien...

3 Beds
2 Baths
Waterleigh SubDv.
34787 Zip Code

15755 Cutter Sail Place, Winter Garden image

15755 Cutter Sail Place, Winter Garden $797,999

Welcome to 15755 Cutter Sail Place located in the Lakeshore Preserve Community in Horizons West. The Bavaro Model is one of the most sought after homes built by Toll Brot...

4 Beds
3 Baths
Lakeshore Preserve Ph 5 SubDv.
34787 Zip Code

8109 Red Crossbill Street, Winter Garden image

8109 Red Crossbill Street, Winter Garden $490,000

Welcome to Summerlake and 8109 Red Crossbill Street! This lovely home on a premium Corner Lot features THREE FULL EN-SUITE bedrooms with private bathrooms, two spacious f...

3 Beds
3 Baths
Summerlake Pd Ph 01a SubDv.
34787 Zip Code

5549 Myrtle Pine Lane, Winter Garden image

5549 Myrtle Pine Lane, Winter Garden $539,999

Welcome to 5549 Myrtle Pine Lane located in the beautiful Orchard Hills Community right here in highly desirable Winter Garden! This is a stunning very well maintained 2 ...

4 Beds
2 Baths
Orchard Hills Ph 3 SubDv.
34787 Zip Code

15798 Citrus Grove Loop, Winter Garden image

15798 Citrus Grove Loop, Winter Garden $540,000

***PROFESSIONAL PHOTOS COMING SOON*** Amazing opportunity to own this Beautiful corner lot, 3 Bedrooms, 2.5 Baths plus loft home in the desirable Gated community of Hicko...

3 Beds
2 Baths
Hickory Hammock SubDv.
34787 Zip Code

10100 Tawny Meadow Alley, Winter Garden image

10100 Tawny Meadow Alley, Winter Garden — N.A $390,990

Excellent end-unit townhouse like new (model Sandhill - built by DR Horton late 2019), located in one of the most desirable communities in the Winter Garden area. This pr...

3 Beds
2 Baths
Waterleigh Phase 2d 97/79 Lot 370 SubDv.
34787 Zip Code

521 First Cape Coral Drive, Winter Garden image

521 First Cape Coral Drive, Winter Garden $495,000

LAKE ACCESS, GATED COMMUNITY, GREAT AMMENITIES, NEW ROOF (Aug.2021) and LARGE FENCED YARD,STUNNING HOME, WOW!! Be prepared to be amazed when you enter this immaculately m...

4 Beds
2 Baths
Black Lake Park Ph 01 SubDv.
34787 Zip Code

2189 Standing Rock Circle, Oakland image

2189 Standing Rock Circle, Oakland $436,380

A Stunning Meritage Home awaits you in this upscale community of Oakland Trails. This elegant home was built in 2020 and has been used as the owners second home. As you e...

3 Beds
2 Baths
Oakland Trails SubDv.
34787 Zip Code

2515 Prairie View Drive, Winter Garden image

2515 Prairie View Drive, Winter Garden $545,000

Beautiful POOL home in the Highly SOUGHT AFTER, desirable GATED community of Wintermere Pointe. Ready NOW! SPLIT PLAN with 4 spacious BEDOOMS and 3 FULL BATHROOMS. TALL C...

4 Beds
3 Baths
Wintermere Pointe Ph 02 46/141 SubDv.
34787 Zip Code

226 Charlotte Street, Winter Garden image

226 Charlotte Street, Winter Garden $340,000

Just imagine how life will be once you are moved into your new place. The exterior was just painted this year! This property offers 3 bedrooms and 2 Baths. This fireplace...

3 Beds
2 Baths
East Garden Manor Rep SubDv.
34787 Zip Code

937 Bainbridge Loop, Winter Garden image

937 Bainbridge Loop, Winter Garden $385,000

Come visit this beautiful 3 bedroom 2 bathroom home located in Covington Park! The home features granite countertops, newer appliances, vaulted ceilings, split floorplan,...

3 Beds
2 Baths
Covington Park A B D E F G & J SubDv.
34787 Zip Code

10078 Salt Point Drive, Winter Garden image

10078 Salt Point Drive, Winter Garden — Ibis $368,740

Under Construction. The Ibis at Waterleigh is a spacious town home with 3 bedrooms, 2.5 baths with stainless steel appliances. This home invites you from the time you ent...

3 Beds
2 Baths
Waterleigh SubDv.
34787 Zip Code

571 E Cypress Street, Winter Garden image

571 E Cypress Street, Winter Garden $219,900

NO HOA!!! Huge back yard with a big carport on back to work on cars or store a boat. Plenty of space besides to store RV's if needed. Walking distance to downtown Winter ...

3 Beds
2 Baths
Overstreet Crate SubDv.
34787 Zip Code

15311 Calming Balsam Alley, Winter Garden image

15311 Calming Balsam Alley, Winter Garden — Enclave At Hamlin $629,000

Take a glimpse into the captivating Baldwin floor plan. Embrace this beauty and the peace of mind of knowing you have ample space to call home with 2,921 sq. ft., 4 bedr...

4 Beds
4 Baths
Enclave/Hamlin SubDv.
34787 Zip Code

10090 Salt Point Drive, Winter Garden image

10090 Salt Point Drive, Winter Garden — Sandhill $389,240

Under Construction. The Sandhill at Waterleigh is a spacious Town home with 3 bedrooms, 2.5 baths with stainless steel appliances. This home invites you from the time you...

3 Beds
2 Baths
Waterleigh SubDv.
34787 Zip Code

8837 Sonoma Coast Drive, Winter Garden image

8837 Sonoma Coast Drive, Winter Garden $612,351

Under Construction. The Arbor in Waterleigh is a spacious one story open floor plan with 3 bedrooms, 3 baths, 3 car garage. This home invites you in from the time you ent...

4 Beds
3 Baths
Waterleigh SubDv.
34787 Zip Code

15556 Mango Isle Street, Winter Garden image

15556 Mango Isle Street, Winter Garden $591,521

Under Construction. Located in our Waterleigh Community, This charming Bellmore Floorplan, 1 story 4 bedroom 3 bath home features a beautiful kitchen that opens to a spac...

4 Beds
3 Baths
Waterleigh SubDv.
34787 Zip Code

8848 Bismarck Palm Drive, Winter Garden image

8848 Bismarck Palm Drive, Winter Garden — 8848 $499,900

BEAUTIFUL and WELL MAINTAINED LUXURY TOWNHOME Shows better than the model! This meticulously designed Toll Brother's Dante model, has been upgraded inside with premium pl...