Homes for Sale in Windermere, Florida

Windermere, Florida

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Homes in Windermere, Florida

If you’re looking to buy a home in Winter Springs, call us today at 407-564-2758 or fill out the form below, and we will be in touch. We will answer all your questions and go on the hunt to find that perfect piece of Longwood, Florida real estate that you can call home.

Windermere, Florida Homes for Sale

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13242 ORANGE ISLE DRIVE

Windermere, Florida 34786

5Bedroom(s)
5Bathroom(s)
39Picture(s)
3,312Sqft
Visits:5
Welcome to this stunning residence in the sought-after community of The Sanctuary At Lakes Of Windermere! Nestled in an AMAZING LOCATION, this spacious home offers five bedrooms and five-and-a-half baths, providing ample space for comfortable living. As you approach, a charming front porch welcomes you, setting the tone for the elegance within.
$890,000

2508 HEMPEL COVE COURT

Windermere, Florida 34786

5Bedroom(s)
6Bathroom(s)
72Picture(s)
5,478Sqft
Visits:8
Discover this hidden luxurious Mediterranean inspired custom estate nestled behind a private double iron gate leading to a wide circular paved driveway on a 1.21 acre lot. Once you pass through the gates you will be greeted with a majestic double porte-cochere adding both convenience and style to the home.
$1,850,000

11918 OTTERBROOKE TRAIL

Windermere, Florida 34786

4Bedroom(s)
3Bathroom(s)
1Picture(s)
3,390Sqft
Visits:6
Welcome to your FULLY FURNISHED AND DECORATED dream home, a stunning 3,390 sq. ft. oasis of elegance and comfort, nestled in the prestigious Windermere Trails community. This meticulously designed 4-bedroom, 3.5-bathroom estate perfectly balances luxury and functionality, offering unmatched lifestyle.
$939,999

8260 TIBET BUTLER DRIVE

Windermere, Florida 34786

5Bedroom(s)
5Bathroom(s)
13Picture(s)
4,291Sqft
Visits:5
Welcome to your dream retreat in the highly sought-after Keenes Pointe neighborhood of Windermere, FL! This exquisite residence boasts five spacious en suite bedrooms, ensuring ultimate comfort and privacy for family and guests alike. With three of the bedrooms conveniently located on the first floor, this home is perfect for easy living.
$1,875,000

13701 BECKMAN DRIVE

Windermere, Florida 34786

3Bedroom(s)
2Bathroom(s)
29Picture(s)
2,091Sqft
Visits:7
GORGEOUS RECENTLY RENOVATED TOWN-HOME!!!!! . The property is a corner unit conveniently located close to dining, shopping and entertainment at downtown Windermere and Winter Garden Village. Property features includes kitchen, dining room and living room combo with an open concept.
$498,900

5174 VARDON DRIVE

Windermere, Florida 34786

6Bedroom(s)
7Bathroom(s)
100Picture(s)
10,701Sqft
Visits:5
... Move in ready custom home in the 24 hours guarded community... This is a 6 bedroom suites, 7 baths, 2 1/2 baths, and 4 car garage custom home that offers over 10,000 square feet of heated space back to the golf course. The grand marble foyer and curved staircase create the elegant feel for the home.
$5,500,000

8757 VIA TAVOLERIA WAY

Windermere, Florida 34786

3Bedroom(s)
2Bathroom(s)
35Picture(s)
1,974Sqft
Visits:8
One or more photo(s) has been virtually staged. Introducing your new home nestled in the heart of Windermere! This beautiful 3 bed 2.5 bath townhome is located in the picturesque neighborhood of Carrington right behind Disney World. Friendly neighbors and beautiful landscaping greet you as you enter the quiet community.
$490,000

715 MAGNOLIA STREET

Windermere, Florida 34786

5Bedroom(s)
4Bathroom(s)
54Picture(s)
3,390Sqft
Visits:6
A beautiful home located in the heart of downtown Windermere offering 4-bedrooms, 3-bathrooms, with a perfect blend of comfort and convenience. The house features hardwood floors throughout, living room with fireplace, and large sliders that open to a beautiful backyard. This is a great home for entertaining or relaxing.
$1,250,000

12663 HAWKSTONE DRIVE

Windermere, Florida 34786

4Bedroom(s)
3Bathroom(s)
26Picture(s)
3,919Sqft
Visits:6
Exquisite custom LAKEFRONT POOL HOME in desirable WINDERMERE on Lake Sawyer. This stunning beauty has 4 bedrooms and 3.5 baths, a separate office, a bonus room with a spectacular view of the lake, and a 3-car garage. The moment you enter this amazing residence, you will feel welcomed by its beautiful features, including ornate columns, crown molding, travertine floors, and engineered wood floors.
$1,850,000

6811 HELMSLEY CIRCLE

Windermere, Florida 34786

4Bedroom(s)
3Bathroom(s)
41Picture(s)
2,485Sqft
Visits:8
Welcome to 6811 Helmsley Circle, a modern 4-bedroom, 3-bathroom single-family home with an extra-large upstairs office, located in the charming community of Windermere. Boasting 2,485 sq. ft. of living space, this home blends luxury and comfort effortlessly. As you approach, the lush landscaping and inviting front porch welcome you, setting the stage for the peaceful lifestyle within.
$650,000

7736 RIGBY STREET

Windermere, Florida 34786

3Bedroom(s)
2Bathroom(s)
14Picture(s)
1,505Sqft
Visits:8
Fantastic 3-bedroom, 2.5-bath townhouse in the desirable Wickham Park community. The kitchen features solid surface countertops, stainless steel appliances, an island, and a breakfast bar. There's an enclosed area at the back, between the townhouse and garage, perfect for a garden or grilling. Close to Walt Disney World, Wickham Park offers amenities like a pool, parks, and a clubhouse.
$449,900

6143 CARTMEL LANE

Windermere, Florida 34786

4Bedroom(s)
5Bathroom(s)
65Picture(s)
4,582Sqft
Visits:8
Welcome to this breathtaking Mediterranean-inspired custom home in the prestigious Lake Butler Sound community. From the moment you arrive at the circular driveway, you'll be captivated by its exquisite design, featuring a classic turret and a timeless tile roof.
$2,395,000

8259 MARITIME FLAG STREET

Windermere, Florida 34786

3Bedroom(s)
2Bathroom(s)
39Picture(s)
1,460Sqft
Visits:9
Don’t miss the opportunity to make this beautiful 3 bedroom townhome your own! The sought out Windermere Lakeside Villas Community offers resort-style amenities including a fitness center, clubhouse, volleyball, tennis courts, playground, fire pit area, walking trails and a large pool. This inviting 3-bedroom, 2.
$350,000

9831 GROSVENOR POINTE CIR

Windermere, Florida 34786

5Bedroom(s)
5Bathroom(s)
74Picture(s)
5,320Sqft
Visits:12
Keene’s Pointe Beauty – Spectacular Custom Home located on one of the best lots on the 9th fairway of this Jack Nicklaus Signature Course with panoramic golf views, sunsets and water views to the front and back of this estate. Classic Architecture with commanding presence on the outside and a bright, glamourous open concept on the inside.
$2,859,000

14083 ANCILLA BOULEVARD

Windermere, Florida 34786

3Bedroom(s)
2Bathroom(s)
39Picture(s)
1,642Sqft
Visits:8
Located in the heart of Windermere, this charming 3-bedroom, 2.5-bathroom townhouse is truly the perfect place to call home. A bright and spacious main living area greets you as you enter through its front or rear entrance, leading to the updated kitchen which is adorned with granite counters, an island, a breakfast bar, and ample cabinet space for everyday storage.
$399,900

12055 SANDY SHORES DRIVE

Windermere, Florida 34786

5Bedroom(s)
3Bathroom(s)
80Picture(s)
3,104Sqft
Visits:15
Welcome to Central Florida's Resort-Style living on this fresh water private canal front property,90' wide lot with direct access to Lake Butler (chain of lakes) and no HOA! Hidden Gem on a personal dead-end street. Let's preview how the owners have enhanced this home's interior and exterior for living comfort and relaxation plus recreation.
$1,499,000

2925 BUTLER BAY DRIVE

Windermere, Florida 34786

5Bedroom(s)
4Bathroom(s)
80Picture(s)
4,100Sqft
Visits:7
This luxurious estate sits on an amazing lakefront lot on a private 187-acre spring-fed lake, offering breathtaking water views from every corner. Set on a spacious .64-acre lot with a grand circular paver driveway, this home is a true showcase of style.
$1,950,000

11761 BELLA MILANO COURT

Windermere, Florida 34786

5Bedroom(s)
4Bathroom(s)
32Picture(s)
2,844Sqft
Visits:10
For sale is a magnificent home in the very highly sought after Belmere neighborhood. In the famed City of Winderemere live in this beautiful gated community in this stunning 5 bedroom 4.5 bath home. Nestled in a cul-de-sac, virtually zero traffic in front of the house and with the privacy of a permanent conservation land behind, you cant get any position than this home.
$699,000

8544 GREENBANK BOULEVARD

Windermere, Florida 34786

4Bedroom(s)
3Bathroom(s)
44Picture(s)
2,610Sqft
Visits:11
Welcome to your dream home! This spacious 4-bedroom, 3.5-bathroom residence offers the perfect blend of luxury and comfort. Nestled on a desirable corner lot, this property ensures privacy with a full wrap-around fence, providing your own personal oasis. Inside, you'll find two generously sized en suite bedrooms, perfect for hosting guests or offering family members their own private retreats.
$675,000

11227 MACAW COURT

Windermere, Florida 34786

6Bedroom(s)
5Bathroom(s)
60Picture(s)
5,030Sqft
Visits:16
This amazing residence in Keene’s Pointe overlooking the picturesque 4th fairway of the Golden Bear Club has everything you could want or need in a custom home. This flexible floorpan allows the home to be a 6 bedroom with an office, or a 5 bedroom home with two offices.
$2,200,000

5181 LATROBE DRIVE

Windermere, Florida 34786

4Bedroom(s)
4Bathroom(s)
67Picture(s)
3,645Sqft
Visits:16
Welcome home to this beautifully renovated, villa-style retreat located in renowned guard gated Isleworth Golf & Country Club. This home exudes the ideal balance of unwavering luxury and comfort and features only the finest upgraded features and finishes. This meticulously designed home is ideally located along the 4th fairway of the famed Isleworth Golf Course.
$2,649,000

1514 LAKE WHITNEY DRIVE

Windermere, Florida 34786

4Bedroom(s)
5Bathroom(s)
10Picture(s)
6,978Sqft
Visits:14
Discover this luxurious Mediterranean Style Home with this stunning 4-bedroom, 5-bathroom estate, a 6,978 sq. ft. masterpiece nestled on nearly half an acre in the prestigious Reserve at Belmere, Windermere. With breathtaking views of Lake Whitney, this property offers elegance and sophistication at every turn.
$2,400,000

11434 JASPER KAY TERRACE

Windermere, Florida 34786

3Bedroom(s)
2Bathroom(s)
15Picture(s)
1,455Sqft
Visits:23
Beautiful Lakeside at Lakes of Windermere condominium - Third floor corner unit with screened balcony. This unit features an open floor plan that combines kitchen, living room, and dining room. The kitchen feature 42 inch wood cabinets and a breakfast bar. Spacious primary bedroom. The A/C was replaced in October 2020.
$365,000

5926 BLAKEFORD DRIVE

Windermere, Florida 34786

4Bedroom(s)
4Bathroom(s)
38Picture(s)
3,789Sqft
Visits:19
Keene's Pointe - 24-hour gated/attended community in Windermere, Florida. Location! Location! Location! This well maintained home is located on the 11th fairway of The Golden Bear Club a private golf club offering golf, tennis, fitness, swimming and dining. Featuring 3 bedrooms/3 baths, formal living and dining rooms, office/den, and spacious kitchen on the first floor.
$1,599,000
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