Windermere Homes for Sale

Sort Option
  • _score
  • Price ↓
  • Newest Listings First
  • Square Footage ↓
  • Year Built ↓
Grid
List
Map

Single Family

WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
3,931Sqft
Welcome to this Beautiful Pool home nestled in the Reserve at Lake Butler Sound. 24-hours guard-gated community. Located just minutes from fine dining, world-class shopping, and all the area theme parks. Located on a premium conservation lot in one of the most exclusive neighborhoods in Central Florida. Pool and spa have numerous lights, water features.
$864,900

Single Family

1542 Belfiore Way, WINDERMERE, Florida 34786

5Bedroom(s)
5Bathroom(s)
25Picture(s)
5,413Sqft
This majestic 2-story 5,413 sqft home features 5 BR/4.5 BA will impress you with magnificent views from the outdoor oasis !Decorative pavers lead up the oversized driveway to 3 car garage! Double door entry takes you into the formal living room with custom window treatments and formal dining with exquisite columns.
$949,000

Rental

5181 LATROBE DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
4Parking(s)
10Picture(s)
3,645Sqft
Set behind the manned gates of Central Florida’s most exclusive neighborhood and on the 4th hole of the Isleworth Golf Course, this executive pool home offers peace and privacy in a sought-after main phase location.
$9,800

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

5181 LATROBE DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
4Parking(s)
25Picture(s)
3,645Sqft
Set behind the manned gates of Central Florida’s most exclusive neighborhood and on the 4th hole of the Isleworth Golf Course, this executive pool home offers peace and privacy in a sought-after main phase location.
$1,295,000

Single Family

13455 BELLARIA CIRCLE, WINDERMERE, Florida 34786

5Bedroom(s)
7Bathroom(s)
4Parking(s)
25Picture(s)
5,825Sqft
Stunning Custom-Built Home in the luxurious gated community of Bellaria! This 5 Bedroom, 7 Bathroom home is sure to impress. Upon entering the home, you are greeted by the formal living room and dining room, featuring a wine cellar, beautiful tray ceiling, and polished travertine that runs throughout the downstairs living areas.
$1,585,000

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

13885 BLUEBIRD POND, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,786Sqft
Beautiful 4 bedroom, 3.5 bathroom, two-story home in the sought-after community of Summerport in Windermere. Upon entering this home one will immediately notice its dark floors, arch entryways, a study/office, and a formal dining room with tray ceilings.
$399,900

Single Family

11792 HAMPSTEAD STREET, WINDERMERE, Florida 34786

5Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,915Sqft
TURN KEY OPPORTUNITY AWAITS! Everything you have been looking for but haven't been able to find is waiting for you right now in the Enclave, one of Windermere's newest and most popular neighborhoods.
$695,000

Residential

953 LASCALA DR, WINDERMERE, Florida 34786

4Bedroom(s)
2Bathroom(s)
12Picture(s)
COME SEE THIS!!! Beautiful 2-story, 4-bedroom/2.5-bathroom home in the highly sought after, gated community of Belmere Village located in wonderful Windermere. The home features a double-door entry way, where you walk into a spacious living room that connects to the master bedroom, dining room, kitchen, and large family room.
$499,900

Single Family

1535 DINGENS AVENUE, WINDERMERE, Florida 34786

5Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
4,495Sqft
Incredible price reduction! Unbelievable value in the 34786. Live the Country Life in the heart of Town! French Farmhouse in the middle of Florida! Follow tree lined Dingens Ave in Gotha/Windermere all the way down to the cul de sac where you will find this European style custom home. Found on a large 1/2 acre lot this is the quiet country life everyone is dreaming of right now.
$775,000

Single Family

9304 ISLEWORTH GARDENS DRIVE, WINDERMERE, Florida 34786

3Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
5,840Sqft
Stately elegance and exceptional craftsmanship define luxury living from inside this graceful waterfront villa with 3-bedroom suites, Executive office, and private movie theater situated in the secluded Gardens of Isleworth.
$1,895,000

Single Family

6890 TRELLIS VINE LOOP, WINDERMERE, Florida 34786

5Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,463Sqft
Superbly maintained two story home in Windermere! Built in 2015, this 3,463 square foot home has 5 bedrooms, 3.5 baths, and an open floor plan. The gourmet kitchen features 42" cabinets, double ovens, a large center island, granite countertops, stainless steel appliances, and a walk-in pantry.
$579,000

Townhouse

14077 ANCILLA BOULEVARD, WINDERMERE, Florida 34786

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
1,642Sqft
Beautiful Summerport Townhouse move-in ready condition. First floor Master bedroom, brand new A/C unit, brand new maintenance-free quartz countertops in kitchen. Wood flooring throughout first floor except for master bedroom and bathrooms. Completely redone first floor half-bath. Sit on the front porch and watch the sunset over Ancilla Pond. Rear driveway with access road.
$255,000

Lots And Land

HARBOR ISLE DRIVE, WINDERMERE, Florida 34786

12Picture(s)
0.67Sqft
Final opportunity to build your dream home on this last remaining lot within the exclusive gated community of Harbor Isle, a private 32 home community located on the banks of the Butler Chain of Lakes. Bring your own builder, with no time limit to build. This 0.67 acre lot is surrounded by community common area that will not be built on. Minutes from Theme Parks, restaurant row, shopping.
$415,000

Lots And Land

7045 HORIZON CIRCLE, WINDERMERE, Florida 34786

21Picture(s)
1.41Acre
Prime 1+ acre Windermere waterfront lot. 100’ on the Butler Chain of Lakes conveniently located walking distance to restaurants, shopping and fitness. On the fringe, but still within the Town of Windermere where golf carts are common and quaint Main Street gives you the best of both worlds.
$1,500,000

Single Family

12220 GRANDMERE COURT, WINDERMERE, Florida 34786

5Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
3,156Sqft
Located within the gated community of Windermere Grande, this Meticulously maintained home sits on a private Cul-de-sac on an oversized Corner lot backing to a greenbelt. As you pull up to the home you notice the brick pavers lining the driveway with lush landscaping.
$769,000

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.
$1,160,000

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

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

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

3831 MCKINNON ROAD, WINDERMERE, Florida 34786

5Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
4,122Sqft
Private Estate Lakefront home in the heart of Windermere! This 4,122 Sq Ft, 5 bedrooms, 4 baths single family home is located on the highly coveted and prestigious Lake Buynak in Windermere, offering fishing and paddle boarding! You will be swept away by the gorgeous view, big lot size, over 2.70 acres and the serene nature and wildlife.
$1,200,000

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

5005 DOWN POINT LANE, WINDERMERE, Florida 34786

6Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
6,191Sqft
Absolutely stunning, completely remodeled Windermere home with a detached remodeled guest or in-law suite. Covered breezeway to garage and guest house. This 6 bedroom and 5 ½ bath home sits on .87 acre with spectacular lake views. Located in Sunset Bay, a community of upscale, custom built homes with deeded access to Lake Down.
$1,799,000

Single Family

12866 LAKE SAWYER LANE, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
3Parking(s)
10Picture(s)
3,458Sqft
WINDERMERE LAKEFRONT and NO HOA! Take advantage of the incredible opportunity to own this custom 4/3 home on huge lot with 100' of Little Lake Sawyer shoreline. Room to roam inside and out, it's the perfect combination of Olde Florida style complementing the comforts of today's lifestyle. This Cape Cod features block construction, inviting front porch, 3-car garage, and plenty of parking.
$829,000

Lots And Land

9732 CARILLON PARK DRIVE, WINDERMERE, Florida 34786

3Picture(s)
1.37Acre
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. This is a great opportunity for you to build your dream luxury custom home in the most desirable lakes in central Florida.
$1,595,000

Single Family

11231 CAMDEN PARK DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
3,814Sqft
Oversized corner lot. Commanding long water view down the Camden pound. What else? Over $200K worth of structural and cosmetic upgrades were added to the home. Walking distance from the Clubhouse, featuring pool, restaurant, gym and tennis courts.
$669,000

Single Family

9508 WINDY RIDGE ROAD, WINDERMERE, Florida 34786

6Bedroom(s)
14Bathroom(s)
18Picture(s)
51,000Sqft
This 18-acre private walled and gated compound is one of the most exceptional properties in Central Florida, unrivaled by its sheer size, ideal shape, remarkable topography and high elevation. The property offers over 600 feet of unobstructed views and access to one of Lake Bulter's cleanest lakes.
$30,000,000

Single Family

8288 TIBET BUTLER DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
6,745Sqft
Live like Rock star Royalty in this elegantly designed Rick Watson custom home on the shores of Lake Burden. Designed with timeless elegance this luxurious home was meant for entertaining . From the moment you walk up to the huge carved front entry doors with its iron mullions , you will be dazzled by this home, that immediately welcomes you in with dramatic water views that will blow you away.
$2,599,999

Single Family

12516 PARK AVENUE, WINDERMERE, Florida 34786

6Bedroom(s)
8Bathroom(s)
4Parking(s)
25Picture(s)
8,172Sqft
Experience Butler Chain living at its finest in this stunning Akers custom home, situated on a quiet cove of Lake Butler, within the gated community of Chaine du Lac! This home is filled with recent updates, such as a newly resurfaced pool, fresh paint throughout, refinished wood floors, and so much more! The stately curb appeal of this 6 bedroom, 6/2 bathroom, 8,887 sqft home sets high expectatio
$3,150,000

Single Family

2114 GROVE POINT LANE, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
3Parking(s)
25Picture(s)
2,805Sqft
Located in one of the most beautiful gated communities in Windermere, this fully remodeled Mediterranean style home sits on a gorgeous private 1.22 acre lot. As soon as you step foot into this beautiful home you can see that it is perfect for a family or large scale entertaining. This 4 Bedroom/3 Bath home has been fully renovated.
$750,000

Single Family

5318 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, Florida 34786

6Bedroom(s)
10Bathroom(s)
4Parking(s)
25Picture(s)
12,298Sqft
MOTIVATED SELLER! YOUR OFFER MAY BUY THIS STUNNING GOLF-FRONT ESTATE IN ISLEWORTH - SELLER CONSIDERING ALL OFFERS! Dramatic interior includes an interior custom designed, temperature-controlled, grand two-story Pavilion with stone flooring, skylights, a heated pool and spa, a bar, grilling/cooking area, dining area and lounging area - all of which is the absolute focal point of this stunning in
$6,600,000

Single Family

3000 BIRD LANE, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
3,848Sqft
Windermere 1-acre home site, COMPLETELY UPDATED, PRIVATE entry gate, over 3800 square feet PLUS pool! Rarely does a property this special come on the market, and lucky is the early bird to get the first look opportunity! This one-owner home has been completely updated and is in pristine move-in condition.
$1,075,000

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

Single Family

6207 CYPRESS CHASE DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
7Bathroom(s)
3Parking(s)
25Picture(s)
6,085Sqft
*** One of the BEST values in the neighborhood under 2M with its low price per square foot!! *** Welcome to ISLEWORTH, one of the most exclusive GATED communities in the WORLD! Private, luxurious, & inviting, known for its championship GOLF course. Access the renowned Butler Chain of Lakes for a day of boating & entertainment, or enjoy the amenities the Club has to offer.
$1,850,000

Single Family

11365 LEDGEMENT LANE, WINDERMERE, Florida 34786

5Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
2,822Sqft
Absolutely gorgeous 5 bed 3.5 bath pool home with 3 car garage located in the gated community of Glenmuir beautifully positioned on a large private and fenced corner lot. This beautiful home has a master bedroom and 2 ensuites. The very large master has a large and elegant master bath with solid wood cabinetry and granite.
$550,000

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

5045 DOWN POINT LANE, WINDERMERE, Florida 34786

5Bedroom(s)
5Bathroom(s)
3Parking(s)
25Picture(s)
5,636Sqft
RELOCATION, SELLER MOTIVATED! Surround yourself with privacy and Sunsets on Lake Down with all A-rated schools. Impressive home with its own gated private entryway and a Decorative Fountain. No details were spared in this custom Estate built home.
$1,380,000

Single Family

5372 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, Florida 34786

8Bedroom(s)
9Bathroom(s)
3Parking(s)
10Picture(s)
13,230Sqft
Auction Property. This breathtaking estate located within the main gates of Isleworth Golf & Country Club is the perfect place to work and play. Spacious and striking, its Mediterranean exterior and French Renaissance interior impress from first look. Step past the lush tropical greenery of the well-established gardens and through the home’s elegant front doors.
$7,400,000

Single Family

5120 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
7Bathroom(s)
3Parking(s)
10Picture(s)
7,070Sqft
This modern estate, featuring five bedrooms and six full and one half baths, rests on an acre overlooking the seventh fairway of Isleworth’s championship golf course and the beautiful Lake Bessie. The dynamic design makes full use of Art Deco geometry in the windows, doors and ceiling details.
$3,600,000

Residential

4812 LEWIS GARDEN COURT, WINDERMERE, Florida 34786

4Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
4,505Sqft
One or more photo(s) has been virtually staged. Under Construction. Completion May 2020. With a Spanish style and modern design, The Georgia by Goehring & Morgan combines open spaces with beautiful finishes for a breathtaking retreat within the Gardens of Isleworth. Beyond the circular motor court, an arched wooden door reveals the foyer with groin vault leading into the two-story home.
$2,498,000

Single Family

6186 LOUISE COVE DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
4,849Sqft
Within the gates of Isleworth West, this elegant estate is nestled on a large corner home site and spans more than 4,800 square feet of living space. Beautiful custom doors reveal a lovely formal living room with an expansive bay window that frames the sparkling open-air pool, spa and lush landscaping.
$1,500,000

Single Family

5056 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, Florida 34786

3Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
4,225Sqft
Offering a prime location within the gates of the renowned Isleworth Golf & Country Club, this beautifully updated golf-front estate sits along the front nine overlooking the 6th fairway. Completely reimagined both inside and out, the estate boasts exquisite, quality finishes at every turn.
$2,590,000

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.
$3,099,000

Single Family

13418 HOPKINTON COURT, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
2,745Sqft
Welcome home to the desirable gated Preserve at the Lakes of Windermere. Located on a quiet cul de sac, this beautiful two-story, 4 bedroom, 3 and ½ bath home has been immaculately cared for by the original owners. It is situated on an oversized, extensively landscaped corner lot and includes a spacious 3 car garage.
$469,900

Single Family

5305 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
7Bathroom(s)
5Parking(s)
25Picture(s)
7,463Sqft
GOLF AND LAKEFRONT! Situated on the 18th green at Isleworth Country Club and boasting stunning views of Lake Louise in the Butler Chain of Lakes, this Isleworth mansion is perfectly positioned in every way imaginable. Whether you want to lounge poolside and watch the golfers hit in or relax in the covered lanai and enjoy the summer kitchen while taking in the lake view, this home has it all.
$3,700,000

Single Family

5284 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
5Bathroom(s)
3Parking(s)
25Picture(s)
6,738Sqft
Poised on Isleworth Country Club Drive overlooking Eagle Pond and the 11th tee, this exquisite estate offers exceptional golf and water views within the gates of Central Florida's most iconic golf and country club community.
$3,400,000
92 Results returned.Per Page
Do NOT follow this link or you will be banned from the site!