Homes with Pools for Sale in Winter Garden, FL

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NEW 23 HRS AGO3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Winter Garden, FL:
This is a rare opportunity to find a popular Roseland floorplan loaded with upgrades, perfectly located on a quiet cul-de-sac on a private lot with no rear neighbors and extra space on this oversized lot! Best of all, you can enjoy picturesque views of Johns Lake right from the front yard! Inside, you are greeted with a beautiful double glass door entry, soaring dramatic ceilings, and elevated light fixtures that create an immediate sense of openness and grandeur. Luxury vinyl plank floors throughout bring warmth to the home. To the right, you have an oversized flex room with French doors, making a perfect home office, play area, or home gym. The formal dining room provides a great space to

$1,200,000

5 beds5 baths4,396 sq ft

4817 Fair Winds Ct, Winter Garden, FL 34787

Private lot • Quiet cul-de-sac • No rear neighbors

EARLY ACCESSCOMPASS COMING SOON

$350,000

3 beds3 baths1,625 sq ft

1017 Priory Cir, Winter Garden, FL 34787

Garage • Pool • Built 2008

NEW 9 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Winter Garden, FL:
Own your piece of the Orlando vacation market at The Grove Resort & Water Park! Located on the 4th floor of Building 3, near the water park, this fully furnished 2-bedroom, 2-bath condo offers the perfect combination of a personal vacation retreat and investment opportunity. The Grove is a Walt Disney World Good Neighbor Hotel located just minutes from the parks, with complimentary shuttle service to Walt Disney World. Owners and guests enjoy resort-style amenities including Surfari Water Park with a lazy river, water slides and FlowRider surf simulator, multiple pools, spa, fitness center, mini golf, arcade, and on-site restaurants and bars. With an on-site rental management program

$180,000

2 beds2 baths1,265 sq ft

14501 Grove Resort Ave #3403, Winter Garden, FL 34787

Lazy river • Water slides • Water park

NEW 11 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Winter Garden, FL:
Under Construction. Step into the Mystique, a single-story new construction home situated just a short walk away from the community amenities offering 2 spacious bedrooms, 2 beautifully appointed bathrooms, an enclosed flex room—perfect for a home office or quiet retreat, and a 2-car garage with additional tandem storage space. The open-concept layout seamlessly connects the gourmet kitchen, café, and gathering room, creating an airy atmosphere. The many windows bathe the entire space in natural light, elevating the overall feeling of openness. The heart of the home is the chef-inspired kitchen, where 42” soft-close cabinetry meets luxurious quartz countertops and a decor

$775,000

2 beds2 baths1,889 sq ft

13056 Sandcastle Dr, Winter Garden, FL 34787

Enclosed flex room • Gourmet kitchen • Owner's suite

NEW 12 HRS AGOFLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Winter Garden, FL:
Imagine having the West Orange Trail practically in your backyard. .. talk about Florida Lifestyle. Located in the beautiful gated Preserve at Crown Point, this meticulously maintained home sits on a premier homesite with a lush conservation setting behind it and the West Orange Trail literally right out your front door and trailing behind your home. Think morning walks, bike rides and evening strolls. Inside, the home feels bright, spacious, and beautifully cared for. The open kitchen and living areas were made for gathering, with an oversized quartz island, 42” cabinetry, stainless steel appliances, farmhouse sink, upgraded lower cabinet drawers, and a dedicated coffee station. The

$579,900

4 beds3 baths2,501 sq ft

2333 Farnham Dr, Ocoee, FL 34761

Large screened lanai • Paver patio • 7,047 sq ft lot

Property at 17882 Adrift Rd, Winter Garden, FL 34787, 4 beds, 3 baths

$879,999

4 beds3 baths2,931 sq ft

17882 Adrift Rd, Winter Garden, FL 34787

Property at 14075 Lochend Way, Winter Garden, FL 34787, 4 beds, 3 baths

$490,000

4 beds3 baths2,197 sq ft

14075 Lochend Way, Winter Garden, FL 34787

Property at 15526 Mango Isle St, Winter Garden, FL 34787, 4 beds, 3 baths

$777,000

4 beds3 baths2,117 sq ft

15526 Mango Isle St, Winter Garden, FL 34787

Property at 2039 Harbor Cove Way, Winter Garden, FL 34787, 4 beds, 3 baths

$730,000

4 beds3 baths2,643 sq ft

2039 Harbor Cove Way, Winter Garden, FL 34787

Property at 9982 Beach Port Dr, Winter Garden, FL 34787, 4 beds, 3.5 baths

$825,000

4 beds3.5 baths2,921 sq ft

9982 Beach Port Dr, Winter Garden, FL 34787

Property at 5887 Cypress Hill Rd, Winter Garden, FL 34787, 3 beds, 2.5 baths

$450,000

3 beds2.5 baths1,810 sq ft

5887 Cypress Hill Rd, Winter Garden, FL 34787

Property at 16795 Turtle Hatch Dr, Winter Garden, FL 34787, 5 beds, 5 baths

$1,249,990

5 beds5 baths3,615 sq ft

16795 Turtle Hatch Dr, Winter Garden, FL 34787

Property at 10625 Atwater Bay Dr, Winter Garden, FL 34787, 4 beds, 3 baths

$590,000

4 beds3 baths2,477 sq ft

10625 Atwater Bay Dr, Winter Garden, FL 34787

Property at 2108 Tillman Ave, Winter Garden, FL 34787, 5 beds, 4 baths

$849,000

5 beds4 baths3,078 sq ft

2108 Tillman Ave, Winter Garden, FL 34787

Property at 12728 Charmed Dr, Winter Garden, FL 34787, 5 beds, 4.5 baths

$835,000

5 beds4.5 baths3,231 sq ft

12728 Charmed Dr, Winter Garden, FL 34787

Property at 8001 Pond Apple Dr, Winter Garden, FL 34787, 5 beds, 3 baths

$785,000

5 beds3 baths3,289 sq ft

8001 Pond Apple Dr, Winter Garden, FL 34787

Property at 15680 Panther Lake Dr, Winter Garden, FL 34787, 5 beds, 5 baths

$1,950,000

5 beds5 baths4,329 sq ft

15680 Panther Lake Dr, Winter Garden, FL 34787

Property at 7921 Iceland Gull St, Winter Garden, FL 34787, 3 beds, 2.5 baths

$510,000

3 beds2.5 baths2,193 sq ft

7921 Iceland Gull St, Winter Garden, FL 34787

Property at 14501 Grove Resort Ave #3534, Winter Garden, FL 34787, 3 beds, 2 baths

$199,000

3 beds2 baths1,396 sq ft

14501 Grove Resort Ave #3534, Winter Garden, FL 34787

Property at 526 First Cape Coral Dr, Winter Garden, FL 34787, 4 beds, 4 baths

$1,089,000

4 beds4 baths2,701 sq ft

526 First Cape Coral Dr, Winter Garden, FL 34787

Property at 11156 Hanlon Terrace Aly, Winter Garden, FL 34787, 3 beds, 2.5 baths

$410,000

3 beds2.5 baths1,868 sq ft

11156 Hanlon Terrace Aly, Winter Garden, FL 34787

Property at 15124 Lemon Peel Aly, Winter Garden, FL 34787, 4 beds, 3.5 baths

$627,500

4 beds3.5 baths2,496 sq ft

15124 Lemon Peel Aly, Winter Garden, FL 34787

Property at 1374 Viscaya Cove Blvd, Winter Garden, FL 34787, 4 beds, 3.5 baths

$545,000

4 beds3.5 baths2,492 sq ft

1374 Viscaya Cove Blvd, Winter Garden, FL 34787

Property at 7025 Twilight Bay Dr, Winter Garden, FL 34787, 3 beds, 3 baths

$435,000

3 beds3 baths2,024 sq ft

7025 Twilight Bay Dr, Winter Garden, FL 34787

Property at 2420 Balforn Tower Way, Winter Garden, FL 34787, 3 beds, 2 baths

$619,900

3 beds2 baths1,572 sq ft

2420 Balforn Tower Way, Winter Garden, FL 34787

Property at 3049 Armstrong Ave, Clermont, FL 34714, 3 beds, 2 baths

$410,000

3 beds2 baths1,432 sq ft

3049 Armstrong Ave, Clermont, FL 34714

Property at 9467 Cinzel Aly, Winter Garden, FL 34787, 3 beds, 2.5 baths

$455,000

3 beds2.5 baths1,814 sq ft

9467 Cinzel Aly, Winter Garden, FL 34787

Property at 17425 Water Hemlock Rd, Winter Garden, FL 34787, 4 beds, 3 baths

$814,990

4 beds3 baths2,869 sq ft

17425 Water Hemlock Rd, Winter Garden, FL 34787

Property at 5355 Haven View Dr, Clermont, FL 34714, 3 beds, 2 baths

$407,490

3 beds2 baths1,875 sq ft

5355 Haven View Dr, Clermont, FL 34714

Property at 17937 Lake Star Rd, Winter Garden, FL 34787, 4 beds, 3.5 baths

$889,990

4 beds3.5 baths3,066 sq ft

17937 Lake Star Rd, Winter Garden, FL 34787

Property at 1315 Eastern Pecan Pl #202, Winter Garden, FL 34787, 1 bed, 1 bath

$212,000

1 bed1 bath942 sq ft

1315 Eastern Pecan Pl #202, Winter Garden, FL 34787

Property at 109 Windtree Ln Unit N, Winter Garden, FL 34787, 2 beds, 2 baths

$224,900

2 beds2 baths918 sq ft

109 Windtree Ln Unit N, Winter Garden, FL 34787

Property at 17943 Lake Star Rd, Winter Garden, FL 34787, 5 beds, 5 baths

$949,990

5 beds5 baths3,825 sq ft

17943 Lake Star Rd, Winter Garden, FL 34787

Property at 17419 Water Hemlock Rd, Winter Garden, FL 34787, 5 beds, 4 baths

$939,990

5 beds4 baths3,610 sq ft

17419 Water Hemlock Rd, Winter Garden, FL 34787

Property at 431 Southern Pecan Cir #101, Winter Garden, FL 34787, 3 beds, 2 baths

$284,995

3 beds2 baths1,340 sq ft

431 Southern Pecan Cir #101, Winter Garden, FL 34787

Property at 17431 Water Hemlock Rd, Winter Garden, FL 34787, 4 beds, 3 baths

$789,990

4 beds3 baths2,908 sq ft

17431 Water Hemlock Rd, Winter Garden, FL 34787

Property at 17322 Beachgrass Aly, Winter Garden, FL 34787, 4 beds, 3.5 baths

$669,990

4 beds3.5 baths2,791 sq ft

17322 Beachgrass Aly, Winter Garden, FL 34787

Property at 2716 Gorst Rd, Winter Garden, FL 34787, 5 beds, 5 baths

$859,000

5 beds5 baths3,935 sq ft

2716 Gorst Rd, Winter Garden, FL 34787

Property at 1009 Spring Loop Way, Winter Garden, FL 34787, 3 beds, 2 baths

$475,000

3 beds2 baths1,497 sq ft

1009 Spring Loop Way, Winter Garden, FL 34787

Property at 2031 Wintermere Pointe Dr, Winter Garden, FL 34787, 4 beds, 2 baths

$550,000

4 beds2 baths2,048 sq ft

2031 Wintermere Pointe Dr, Winter Garden, FL 34787

Property at 2204 Romanum Dr, Winter Garden, FL 34787, 4 beds, 3 baths

$549,000

4 beds3 baths2,032 sq ft

2204 Romanum Dr, Winter Garden, FL 34787

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Based on information submitted to the MLS GRID as of Tue Sep 08 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Homes with Pools for Sale in Winter Garden

There are currently 555 homes with pools for sale in Winter Garden at a median listing price of $600K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winter Garden stay on the market for 66 days and receive 1 offers. Popular neighborhoods include Lake Avalon Groves, Stoneybrook West, Bella Collina, Waterside, and Tucker Oaks. This map is refreshed with the newest listings in Winter Garden every 15 minutes.

In the past month, 55 homes have been sold in Winter Garden. In addition to houses in Winter Garden, there were also 40 condos, 38 townhouses, and 0 multi-family units for sale in Winter Garden last month. Winter Garden is a minimally walkable city in Orange County with a Walk Score of 30. Winter Garden is home to approximately 33,581 people and 9,677 jobs. Find your dream home in Winter Garden using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winter Garden are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winter Garden. Our Winter Garden real estate stats and trends will give you more information about home buying and selling trends in Winter Garden. If you're looking to sell your home in the Winter Garden area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winter Garden with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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