Windermere Homes for Sale

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Lots And Land

WOODY DRIVE, WINDERMERE, Florida 34786

23Picture(s)
1.44Acre
If you’ve always wanted to build your dream home in a distinguished community, look no further. This nearly 1.5 acre treed lot is nestled adjacent to Windermere Downs, a well-established community of estate homes. With no deed restrictions, it would be perfect for your custom build.
$435,000

Single Family

5127 LATROBE DRIVE, WINDERMERE, Florida 34786

7Bedroom(s)
8Bathroom(s)
3Parking(s)
25Picture(s)
6,933Sqft
Contemporary vision inside Isleworth Country Club. Welcome to this modern golf front estate, featuring high quality craftsmanship and built. Perfectly situated on the 5th hole of Isleworth's world-renowned golf course, the inviting outdoor living space includes a pool bordered with stone, oversized spa, fire pit, summer kitchen, entertainment areas and plenty of dining space.
$2,700,000

Single Family

4213 ISABELLA CIRCLE, WINDERMERE, Florida 34786

5Bedroom(s)
8Bathroom(s)
3Parking(s)
25Picture(s)
5,353Sqft
Back On the Market Due to Buyers’ Inability to Sell Their Home. Great opportunity available again! Welcome Home "VILLA MILANO" can be yours! Located at luxury gated CASABELLA Windermere upscale community on a premium lot. The floor plan features 5 bedrooms,5 full bathrooms,3 half baths and a 3 car garage.
$1,879,000

Single Family

5085 LATROBE DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
5Bathroom(s)
3Parking(s)
25Picture(s)
4,024Sqft
Nestled along the front nine of Isleworth’s renowned championship golf course, this lovely golf-front residence offers a backdrop of beautiful views of the 5th hole. The single-story home boasts an open and airy interior spanning more than 3,800 square feet of living space, with elegant stone and hardwood floors throughout.
$1,549,000

Single Family

5145 LATROBE DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
4,512Sqft
Nestled along Isleworth’s famed championship golf course overlooking Hole 4, this beautiful golf-front estate spans more than 4,500 square feet and has been updated with modern finishes creating a true golfer’s paradise.
$2,250,000

Single Family

5139 LATROBE DRIVE, WINDERMERE, Florida 34786

3Bedroom(s)
3Bathroom(s)
3Parking(s)
25Picture(s)
3,942Sqft
Set along the front nine of Isleworth’s famed championship golf course, this beautiful estate is a true golf-front paradise overlooking the 4th hole and 5th tee. The interior spans nearly 4,000 square feet and has been updated extensively throughout with new flooring, finishes and modern appointments.
$1,840,000

Single Family

13244 BELLARIA CIRCLE, WINDERMERE, Florida 34786

5Bedroom(s)
7Bathroom(s)
3Parking(s)
25Picture(s)
5,471Sqft
One or more photo(s) has been virtually staged. "Casa Amare," built by Master Custom Builder Castleworks who is most known for their unique style and quality construction. This courtyard-style home, which embodies timeless modern design, is situated on a 3/4 acre lot within the prestigious 24-hour guard gated community of Bellaria.
$1,689,000

Single Family

13118 BELLARIA CIRCLE, WINDERMERE, Florida 34786

5Bedroom(s)
7Bathroom(s)
3Parking(s)
25Picture(s)
6,045Sqft
This Estate Home is located in Bellaria, a 24 hour guard gated community in the heart of Windermere. This stunning home was built by Stonebridge Homes with all of the finest touches and upgrades. The home boasts an expansive and open floor plan and shows like a model home.
$1,685,000

Single Family

6842 TRELLIS VINE LOOP, WINDERMERE, Florida 34786

6Bedroom(s)
5Bathroom(s)
2Parking(s)
25Picture(s)
3,767Sqft
Welcome Home! You have to see this beautiful 6 bedroom 4 1/2 bath home located in Windstone, a Windermere development perfectly situated close to shopping, high rated public and private schools as well as Walt Disney World®. This amazing former model home is awaiting its new owners.
$650,000

Single Family

3013 SEIGNEURY DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
5Bathroom(s)
3Parking(s)
25Picture(s)
5,130Sqft
Stylish and elegant with contemporary touches, welcome home to a magnificent and expansive retreat situated on a 1-acre lot, with full-size lighted sport court for tennis or basketball, set inside the gated enclave of Harbor Isle.
$1,500,000

Single Family

325 MAGNOLIA STREET, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
3,975Sqft
Best value on one of the largest lakefront properties on famed The Butler Chain of Lakes within The Town of Windermere. Watch the most beautiful sunrise and sunsets over lake Down, surrounded by the mature landscaping spread out over almost 3 acres. Be ready for all of your water sport activities. Major extensive renovations from the ground up in 2001 made this home like new construction.
$1,997,000

Single Family

1978 WINDERMERE ROAD, WINDERMERE, Florida 34786

5Bedroom(s)
7Bathroom(s)
25Picture(s)
4,484Sqft
Welcome to one of the most sought out opportunities in Windermere! This beautiful home sits on almost a full acre, is fully fenced, and has NO HOA! Windermere Rural is a quiet and loving community, not to mention the LOCATION LOCATION LOCATION! Your are conevniently located less than 20 minutes from Old Windermere Downtown and Winter Garden Villages, plus only 45 minutes from the beach! The curb a
$995,000

Single Family

9838 LAUREL VALLEY DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
8Bathroom(s)
5Parking(s)
25Picture(s)
10,843Sqft
Capturing majestic sunset views of beautiful Lake Butler, this fabulous lakefront estate is perfectly set between Lake Butler’s shoreline and the 15th hole of Isleworth’s renowned championship golf course. The three-story estate offers a nod to Mizner-inspired architecture and is stunning in both scale and contemporary style.
$6,300,000

Single Family

325 MAGNOLIA STREET, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
3,975Sqft
Best value on one of the largest lakefront properties on famed The Butler Chain of Lakes within The Town of Windermere. Watch the most beautiful sunrise and sunsets over lake Down, surrounded by the mature landscaping spread out over almost 3 acres. Be ready for all of your water sport activities. Major extensive renovations from the ground up in 2001 made this home like new construction.
$1,997,000

Single Family

4282 MCKINNON ROAD, WINDERMERE, Florida 34786

6Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
5,869Sqft
Price Adjustment! Two Story Custom 6 Bedrooms / 6 Baths, 1 Acre Estate Home in Windermere. As you enter the 8' French Doors of the property you are greeted by a Foyer that features a 21' Ceiling, Double Chandeliers, Double Crown Molding, and Wooden Staircase. The property has 10'-12' Ceilings and Crown Molding and 8' Doors throughout.
$1,125,000

Lots And Land

WINDY RIDGE ROAD, WINDERMERE, Florida 34786

3Picture(s)
2.50Acre
The old saying "LOCATION LOCATION LOCATION" is certainly not being overrated with this incredible vacant residential lot. This 2.5 acre lot is located in, beautiful, Windermere, Florida. Location is excellent - great school district, shopping/restaurants/banking, Lake Down Boat ramp (giving you access to the Butler Chain of Lakes), and all within 2 miles of your property.
$799,900

Single Family

5427 MONTERREY CLUB COURT, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
3,957Sqft
A one-of-a-kind residence within the gates of the renowned Isleworth Golf & Country Club, this remarkable estate offers impeccably designed interiors spanning more than 3,900 square feet. A contemporary masterpiece showcasing the pinnacle of modern styling, the property offers an ideal layout for stylish living and entertaining.
$2,350,000

Single Family

9560 Black Walnut Drive, GROVELAND, Florida 34786

5Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,601Sqft
Arborwood presents the Hayden, available to build in Groveland, Florida. This amazing all concrete block construction single-family home features 5 bedrooms and 3 bathrooms optimizing living space with an open concept feel. The kitchen overlooks the dining and great room, while having view to the covered lanai outside.
$0

Single Family

9560 Black Walnut Drive, GROVELAND, Florida 34786

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,432Sqft
Arborwood presents the Galen, available to build in Groveland, Florida. This amazing all concrete block construction single-family home features 4 bedrooms and 2.5 bathrooms optimizing living space with an open concept feel.
$0

Single Family

9560 Black Walnut Drive, GROVELAND, Florida 34786

5Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,807Sqft
Arborwood presents the Elle, available to build in Groveland, Florida. This amazing all concrete block construction single-family home features 5 bedrooms and 3.5 bathrooms optimizing living space with an open concept feel.
$0

Single Family

9560 Black Walnut Drive, GROVELAND, Florida 34786

3Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
1,672Sqft
Arborwood presents the Aria, available to build in Groveland, Florida. This all concrete block construction, one-story layout optimizes living space with an open concept kitchen overlooking the living area, dining room, and covered rear lanai. Entertaining is a breeze, as this popular single-family home features a spacious kitchen island, dining area and a ample sized pantry for extra storage.
$0

Single Family

9560 Black Walnut Drive, GROVELAND, Florida 34786

4Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
1,828Sqft
Arborwood presents the Cali, available to build in Groveland, Florida. This all concrete block constructed, one-story layout optimizes living space with an open concept kitchen overlooking the living area, dining room, and outdoor lanai. Entertaining is a breeze, as this popular single-family home features a spacious kitchen island, dining area and a spacious pantry for extra storage.
$0

Single Family

9560 Black Walnut Drive, GROVELAND, Florida 34786

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,725Sqft
Arborwood presents the McGraw, available to build in Tavares, Florida. This all concrete block constructed, two-story home is designed for todays families and built with your MutiGEN needs in mind. As you enter the foyer you are greeted with a separate suite including living space, bedroom, bathroom, and optional kitchenette; perfect for MultiGEN living or extended stay guests.
$0

Lots And Land

9736 CHESTNUT RIDGE DRIVE, WINDERMERE, Florida 34786

25Picture(s)
0.70Acre
Claim your piece of Isleworth lakefront paradise today. This remarkable property is located on picturesque Lake Bessie and is one of the last lakefront lots in Isleworth. It provides 131 feet of lake frontage and is nestled among beautiful old Florida foliage. From the elevated home site you can enjoy watercolor sunsets and golf course views across the lake.
$1,950,000

Single Family

6024 GREATWATER DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
6,370Sqft
The ultimate in entertaining and privacy; this custom built and one of a kind home is situated in a peaceful area on the 17th hole on the Golden Bear Golf course within sought after Keene’s Pointe. As you enter through the wrought iron gate and doorway you are welcomed into the private courtyard with surrounding balcony.
$2,190,000

Single Family

13957 FLORIGOLD DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
3,402Sqft
Beautiful family home in Eden Isle, gated community amazingly located in Windermere. When entering you enjoy the foyer that extends to the formal living and dining areas with a great open plan boasting tray ceilings and offering flexible space for family and friends gatherings. The kitchen showcases granite counters, cherry paneled cabinetry and tile flooring.
$630,000

Single Family

5318 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, Florida 34786

6Bedroom(s)
10Bathroom(s)
4Parking(s)
25Picture(s)
12,298Sqft
NEW PRICE! MOTIVATED SELLER OFFERS A $500,000. PRICE REDUCTION! WONDERFUL OPPORTUNITY TO PURHASE IN EXCLUSIVE GATED GOLF AND COUNTRY CLUB COMMUNITY, FULL-TIME GUARD-GATEHOUSE. CUSTOM BUILT! Stunning entrance. Pristine condition.
$6,100,000

Single Family

520 HALEY DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
4,883Sqft
Don't miss out on this gorgeous, fully remodeled home located in the Crescent Lakes Estates! This 4 bedrooms, 3.5 bathroom compound sits on a well manicured 1 acre lot with complete privacy. The home has received a full facelift with additions added plus top of the line finishes. You cannot beat this desired open floor plan with a kitchen/dining/family & game room combo.
$1,249,999

Single Family

6103 S HAMPSHIRE COURT, WINDERMERE, Florida 34786

6Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
5,696Sqft
Are you ready to experience the Keene’s Pointe Lifestyle from your Rick Watson custom built home? No expense was spared in the construction of this magnificent property.
$1,650,000

Lots And Land

7085 HORIZON VIEW CIRCLE, WINDERMERE, Florida 34786

12Picture(s)
2.44Acre
LAKE FRONT LOT ON BUTLER CHAIN!! Great opportunity to build dream custom home in the Town of Windermere on pristine Butler Chain of Lakes. The 2.44 acres 120' lakefront property is practically minutes away from the famous Restaurant-Row in Dr. Phillips/Bayhill area, essential offices, and local markets. LA Fitness Gym, Starbucks Coffee-Shop, Publix Super Market, U.
$1,545,000

Lots And Land

716 W 2ND AVENUE, WINDERMERE, Florida 34786

12Picture(s)
0.81Acre
Life doesn’t get any better than this in the Greater Orlando Area! The opportunity to build Your Dream Home on one of the Most Sought-After Streets in the entire Central Florida Area and on one of the Most Famed bodies of water in the state of Florida! This lot is .
$1,899,000

Single Family

5306 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
8Bathroom(s)
3Parking(s)
25Picture(s)
8,802Sqft
Nestled within the main gate of Isleworth Golf & Country Club along the back nine, this exquisite golf-front estate offers beautiful finishes and living spaces set against a backdrop of multiple golf and water views overlooking Holes 11 and 12 along Eagle Pond.
$5,950,000

Single Family

4071 ISABELLA CIRCLE, WINDERMERE, Florida 34786

5Bedroom(s)
8Bathroom(s)
4Parking(s)
25Picture(s)
6,752Sqft
Situated in the exclusive gated community of Casabella and only minutes from upscale dining & shopping, world famous attractions, and Butler Chain of Lakes, this property is surrounded by luxury mansions, and championship golf estates.
$2,399,000

Single Family

12616 PARK AVENUE, WINDERMERE, Florida 34786

5Bedroom(s)
7Bathroom(s)
4Parking(s)
10Picture(s)
7,620Sqft
Check the video tour! https://youtu.be/fKz59yCwhzk Picture perfect living awaits you on the serene shores of Lake Butler. Dreams come true in the gated community of Chaine du Lac in upscale Windermere. Nestled at the end of a charming brick stone path, this immaculate 7,620 sqft estate’s attractive stone exterior evokes a sense of storybook wonder, complete with ivy-scaled tower.
$2,950,000

Single Family

8431 GREENBANK BOULEVARD, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
2,792Sqft
Don't miss the opportunity to own this two story home in the sought out area of Windermere. Located in the gated The Preserve at the Lakes of Windermere community. Enjoy the beautiful Florida weather on the covered front porch or take a dip in the oversized screened in pool. When you walk inside you'll notice the high ceilings and natural light coming in giving this home a bright and open feel.
$479,900

Lots And Land

9732 CARILLON PARK DRIVE, WINDERMERE, Florida 34786

3Picture(s)
1.37Acre
SUPER MOTIVATED SELLER!!!!! FANTASTIC VALUE!!! 1.37 ACRE LAKEFRONT LOT WITH ACCESS TO THE BUTLER CHAIN. This MAGNIFICENT WATERFRONT LOT IS POSITIONED IN THE SPECTACULAR VILLAGE OF GROSVENOR POINTE IN KEENE'S POINTE. This large lot features 211 ft. of street frontage and breathtaking views of the lake.
$1,445,000

Single Family

9288 BLANCHE COVE DRIVE, WINDERMERE, Florida 34786

6Bedroom(s)
8Bathroom(s)
6Parking(s)
21Picture(s)
12,778Sqft
Under Construction. Under construction, with a small window of time to still make it your own.
$7,495,000

Single Family

6719 VALHALLA WAY, WINDERMERE, Florida 34786

4Bedroom(s)
6Bathroom(s)
4Parking(s)
25Picture(s)
4,771Sqft
Incredible French country home on the 16th Green and Lake Tibet. No expense was spared in the built of this solid home. Exposed stained beams, bricks and stone, and cathedral ceilings. A beautifully appointed kitchen offers ample space for entertaining with top-of-the-line Sub-Zero, Wolf and Miele appliances, custom solid wood cabinetry, and exotic granite counters.
$1,890,000

Lots And Land

2034 DOWN HOLLOW LANE, WINDERMERE, Florida 34786

25Picture(s)
4.77Acre
Here is the opportunity you’ve been waiting for to build your very own lakefront paradise! This 4.55 acre lot with DIRECT LAKE FRONTAGE on the highly sought after Butler Chain is located in a charming, private neighborhood close to downtown Windermere and Winter Garden Village. Enjoy stunning views and no time limit to build the home of your dreams.
$999,000

Lots And Land

11811 LAKE BUTLER BOULEVARD, WINDERMERE, Florida 34786

20Picture(s)
1Acre
A Rare & Exclusive Opportunity! This uniquely located homesite in Old Windermere's prime location offers the unique privilege of building your dream home in one of Central Florida's most desirable locations on one of the most desirable homesites available. This special opportunity allows you the freedom to design an exclusive estate home on a 1 acre parcel. This site measures 130 x 335 deep.
$785,000

Single Family

4721 INDIAN DEER ROAD, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,428Sqft
Come see this beautiful one-story 4/3 Pool Home located on a quiet street facing conservation in the very popular Windermere Community Summerport. This home's 3 way split floor plan makes for very comfortable living. This home has been lovingly cared, freshly painted and beautifully decorated with wide-plank luxury vinyl flooring 2018 and stainless steel appliances in the kitchen.
$456,000

Single Family

3324 S LAKE BUTLER BOULEVARD, WINDERMERE, Florida 34786

4Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
5,518Sqft
Discover the best of both worlds in this 4-bedroom, 5/1-bathroom lakefront masterpiece located on a tranquil bay off Lake Butler of the famed Butler Chain of Lakes! Built in 2017, and filled with custom features, the home is perfectly located just a short walk or golf cart ride to Town of Windermere’s shops, restaurants, and Friday Farmers Market.
$3,450,900

Lots And Land

4219 CLARICE ESTATES DRIVE, WINDERMERE, Florida 34786

2Picture(s)
1Acre
This property is build to suit at a minimum of 3,500 sf. Please contact seller for homes plans between 3,500 sf and 8,200 sf or bring your own plans. Amazing 1 acre in a 23 lot boutique subdivision in Windermere proper. Central pond with fountain. Not gated. Heavily treed, offers a unique opportunity for land and privacy on a full Acre lot not common for the area..
$475,000

Single Family

8304 LAKE BURDEN CIRCLE, WINDERMERE, Florida 34786

8Bedroom(s)
10Bathroom(s)
4Parking(s)
23Picture(s)
8,808Sqft
Unparalleled contemporary home within Windermere, Florida's distinguished Keene’s Pointe community featuring The Golden Bear Golf and Country Club. This home is currently the only contemporary property available in Keene's Pointe with lake access. Breathtaking water views and featuring 7-bedroom suites, personal elevator, private office, four spacious garage stalls, and guest quarters.
$3,649,000

Single Family

11069 CONISTON WAY, WINDERMERE, Florida 34786

5Bedroom(s)
5Bathroom(s)
3Parking(s)
25Picture(s)
5,637Sqft
Enter this exquisite 5 bedroom 5 bathroom half-acre Windermere estate located in the desirable 24-hour guard-gated Reserve at Lake Butler. A hand crafted iron gate and soothing fountain garden set the tone as you as you enter the home. Interior finishes include rich marble floors with custom inlays, beautiful ceiling details and soaring two-story ceilings in the spacious family room.
$1,420,000

Single Family

8450 VIVARO ISLE WAY, WINDERMERE, Florida 34786

5Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
3,619Sqft
THIS IS THE HOME YOU HAVE BEEN WAITING FOR! 5 BEDROOMS, BONUS ROOM with a first floor guest suite in an oversized corner lot. Fully upgraded with luxury finishes, you will find this stunning home nestled in a Florida's prime location, only 2 MILES AWAY FROM DISNEY WORLD with stunning POND and SUNSET VIEWS in a community surrounded by A BEAUTIFUL conservation area.
$699,990

Single Family

9053 RON DEN LN LANE, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
3,162Sqft
Totally renovated UNIQUE 3,162 sf custom house within 16,821 sf lot located in the luxurious Windermere area. Steps away from Lake Down of the famed Butler Chain of Lakes. Spectacular views and access to private community dock. Ample driveway that includes covered RV/Boat garage. Big private backyard. Four bedrooms being two of them Masters: one in upper floor and the other at ground level.
$765,000

Single Family

8236 PROCIDA ISLE LANE, WINDERMERE, Florida 34786

6Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
4,176Sqft
This home HAS IT ALL! Greeted by a welcoming brick paver front porch you step into light and bright foyer with office at front of the home wood tile floors flow throughout downstairs with a gorgeous gourmet kitchen with 42 inch cabinets, gas appliances light granite countertops, subway tile backsplash, a unique coffee bar nook with extra storage and walk in pantry with upgraded shelving.
$699,900
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Tony Johnson - Realtor - Greater Orlando FL Area Homes for Sale and Real Estate Listings