Windermere Homes for Sale

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Single Family

4095 ISABELLA CIRCLE, WINDERMERE, Florida 34786

5Bedroom(s)
7Bathroom(s)
3Parking(s)
25Picture(s)
5,423Sqft
Enjoy a sophisticated, true Florida lifestyle in this transitional masterpiece located within guard-gated Casabella at Windermere. No detail was overlooked in this 5 bedroom, 5/2 bathroom, pool home with more than 5,400 SqFt of living space! Stepping into the impressive grand foyer you are instantly greeted by a striking 12 ft.
$1,879,000

Single Family

5317 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
7Bathroom(s)
3Parking(s)
25Picture(s)
6,189Sqft
Exquisitely set along Isleworth’s back nine behind the 18th tee, this grand estate offers views extending from the tee box down the fairway and overlooking beautiful Lake Louise. The traditional home spans more than 6,100 square feet and is nestled on a picturesque home site totaling 0.78 acres.
$2,700,000

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.
$2,649,000

Residential

5091 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
8Bathroom(s)
4Parking(s)
25Picture(s)
6,423Sqft
Positioned along the front nine of Isleworth’s famed championship golf course, this beautiful residence offers expansive views of the fourth fairway. Elegant and refined yet ideal for casual living, the estate encompasses more than 6,400 square feet of living space across a sprawling two-story floor plan.
$3,295,000

Single Family

5372 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, Florida 34786

8Bedroom(s)
9Bathroom(s)
3Parking(s)
10Picture(s)
13,230Sqft
Discover the very best in Isleworth living through this spectacular estate overlooking the serene waters of Hourglass Lake. The estate is a rich and fascinating masterpiece that inspires superior craftsmanship and exudes both sophistication and panache at every turn.
$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

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

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.
$3,199,000

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

Single Family

5318 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, Florida 34786

6Bedroom(s)
10Bathroom(s)
4Parking(s)
25Picture(s)
12,298Sqft
IMMEDIATELY IMPRESSIVE AND DRAMATIC! Golf-front custom built estate for current owner -the fulfillment of your dreams of owning a Florida estate in Orlando's most exclusive, gated, amenity-rich community- "Isleworth Golf and Country Club" - cited on an almost 2-acre golf-front lot, and beautifully embraced by a formal manicured landscape and flower gardens.
$6,750,000

Single Family

11035 SCHOONER WAY, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
2Parking(s)
6Picture(s)
3,517Sqft
Nestled among the Butler Chain of Lakes in the Town of Windermere, find tranquility in Marina Bay living. This homes warmth truly enhances the family experience and features many upgrades, a spacious floor plan and oversized lot. Home has no HOA with an added plus of RV/Boat station with electricity and water.
$785,000

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

6255 RIVER FRUIT COURT, WINDERMERE, Florida 34786

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,172Sqft
View this home - Anytime - 24 hours a day with our 3D virtual tours - Exciting opportunity to purchase a fantastic two-story home on a corner lot with New exterior paint, impressive imported DuChateau wood flooring, and park view.
$375,000

Townhouse

5669 SOMERSBY ROAD, WINDERMERE, Florida 34786

3Bedroom(s)
3Bathroom(s)
2Parking(s)
20Picture(s)
1,510Sqft
Precious two story 1510 sq. ft. corner townhome with 3 bedrooms and 2.5 baths in the picturesque Tennyson Park neighborhood of Summerport in Windermere. The home has a front porch and shade trees in yard and a screened brick patio next to a 2-car garage on driveway behind house. Family room with dining area, large kitchen with pantry, breakfast nook and washer/dryer closet.
$275,000

Single Family

13807 BLUEBIRD POND ROAD, WINDERMERE, Florida 34786

3Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
1,950Sqft
Home of PGA TOUR & prestigious Q-SCHOOL! Experience exciting and stress-free living in this absolutely stunning ranch-style home in the gorgeous Summerport community thats just 10 minutes from where world-renowned golfers play. Just a short walk to the tranquil community lake, this home also features lush & mature landscaping, an over-sized 2 car garage, and freshly painted interior walls.
$334,900

Single Family

8512 ABBOTSBURY DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,599Sqft
One or more photo(s) has been virtually staged. The Preserve at the Lakes of Windermere an INVITING established gated neighborhood located near Walt Disney? World will certainly delight you?! Gather around the community pool, playground, or grab a picnic table and fire up the bbq grill for a cookout. There is a gazebo, conservation pond and water fountain too.
$379,900

Single Family

11854 CAMDEN PARK DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,620Sqft
PROICE HAS JUST BEEN REDUCED BY $10,000 to $629,900. SELLERS ARE MOTIVATED! SELLERS HAVE SPENT OVER $40,0000 IN THE PAST 6 MONTHS ADDING A BRAND NEW ROOF IN SEPTEMBER 2020, BRAND NEW DUAL CARRIER HIGH EFFICIENCY AC SYSTEMS IN FEBRUARY 2020, AND A BRAND NEW REFRIGERATOR IN AUGUST 2020.
$629,900

Lots And Land

DOWN YONDER LANE, WINDERMERE, Florida 34786

25Picture(s)
3.76Acre
Build your Custom Home on the best lot available on the Windermere Chain. This huge lot features over 1.3 acres buildable land with nearly 600’ of Lakefront tucked away on a peninsula. Numerous large majestic Live Oaks are scattered evenly throughout the estate.
$1,350,000

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

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 entryway and a Decorative Fountain. No details were spared in this custom built home.
$1,380,000

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.
$1,495,000

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 Chain 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 expectation
$3,150,000

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

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.
$680,000

Single Family

13573 GORGONA ISLE DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,224Sqft
SPECTACULAR Carlisle model. This home is in mint condition! One owner home, lovingly cared for and loaded with upgrades! Starting with the Stacked stone elevation, tile roof and full front porch to the gorgeous glass front door. 8' interior doors and beautiful wood plank tile throughout living areas with carpet in bedrooms.
$425,000

Single Family

8512 ABBOTSBURY DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,599Sqft
One or more photo(s) has been virtually staged. The Preserve at the Lakes of Windermere is an INVITING established gated neighborhood located near Walt Disney World. The clubhouse is a great place to meet up with neighbors and socialize. Gather around the community pool, playground, or grab a picnic table and fire up the bbq grill for a cookout.
$379,900

Rental

9394 WOODBREEZE BOULEVARD, WINDERMERE, Florida 34786

3Bedroom(s)
2Bathroom(s)
2Parking(s)
13Picture(s)
1,723Sqft
Clean and maintained 3 bedroom, 2 bathrooms. Formal living and dining rooms. Kitchen opens to family room. Kitchen has had updates to cabinets and granite counter tops. Split bedroom floorplan. All ceramic tile flooring throughout the entire house. Both bathrooms have been updated. Indoor laundry room. Huge lot! 2 car garage. Windermere Elementary, Chain of Lakes Middle and Olympia High School.
$2,200

Residential

9053 RON DEN LANE, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
2Parking(s)
10Picture(s)
3,162Sqft
Relax on your 2nd floor balcony and enjoy beautiful views of Lake Down. This elevated .39 acre lot is treed and fenced. Very private in the rear. Sit out back by the fire pit and enjoy the sights and sounds of nature. Original hardwood flooring, walls and ceilings give the feeling of living in a cabin. Home features a huge 16x36ft living room and dining room combination.
$450,000

Single Family

9304 WOODBREEZE BOULEVARD, WINDERMERE, Florida 34786

3Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
2,155Sqft
Come and see this beautiful, turn key home in a highly desirable established quiet neighborhood that lies between Dr. Phillips to the east and Isleworth to the west. Can you say location?!! The home features 2155 sq ft with a split floor plan. The large open concept family room has vaulted ceilings. The beautiful porcelain tile floors are throughout the entire home.
$475,000

Single Family

4486 BLUE MAJOR DRIVE, WINDERMERE, Florida 34786

6Bedroom(s)
3Bathroom(s)
2Parking(s)
10Picture(s)
3,211Sqft
One or more photo(s) has been virtually staged. This immaculate house is presented pristinely with its upgrades, major renovations, pool and pond views. Located only miles from the famous Winter Garden and Disney entertaining complexes.
$539,900

Single Family

6126 GREATWATER DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
5Bathroom(s)
3Parking(s)
25Picture(s)
4,594Sqft
STUNNING KEENE'S POINTE GEM located on an oversized lot nestled on the 17th Fairway of the 18-hole Jack Nicklaus-designed signature golf course at the Golden Bear Club. This home has been meticulously, thoughtfully and lovingly remodeled with impressive upgrades and fabulous fixtures. As you enter this 4,594 Sq. Ft.
$1,275,000

Single Family

9316 ISLEWORTH GARDENS DRIVE, WINDERMERE, Florida 34786

3Bedroom(s)
5Bathroom(s)
3Parking(s)
25Picture(s)
4,089Sqft
Short Sale. Stunning 4089 sq.ft. Villa with water views has been carefully designed to blend effortlessly with the surrounding Mediterranean style residences in the gated community of “Gardens of Isleworth”. As the name implies, community is plush with grand Cypress trees, mature Oaks, rolling green grass, tropical flora and serene waterways.
$1,600,000

Single Family

6233 GREATWATER DRIVE, WINDERMERE, Florida 34786

6Bedroom(s)
8Bathroom(s)
3Parking(s)
25Picture(s)
7,757Sqft
Discover the ultimate in lakefront living at this custom family compound with not one but two detached guest residences, expansive indoor and outdoor living, complete with a well-appointed boat dock that is perfect for social distancing while keeping family and friends together. Built in 2002 by Goehring & Morgan, this classic estate is situated on 1.15 +/- high and dry acres with 146 ft.
$3,495,000

Single Family

11924 PERSPECTIVE DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
3,635Sqft
BACK ON MARKET/ HERE IS YOUR OPPORTUNITY TO OWN THIS BEAUTIFUL HOME!! It features 4 Bedrooms, 3 Baths, a bonus room, a spacious kitchen, a 2 Car Garage, and much more!! Home has a PARK VIEW! The formal dining features Coffered ceilings and the Kitchen features Granite Counters, Stainless Steel Appliances, and a Walk-in Pantry.
$455,000

Single Family

6416 LAKE BURDEN VIEW DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
4,425Sqft
Upon entering this Mediterranean inspired masterpiece you will notice all the attention to detail with an intricately placed wood ceiling as well as stately crown molding throughout the home. A five bedroom six bath estate with all the trimmings you would expect in a home built by the renowned Stonebridge Custom homes whom currently build at Disney’s elite community Golden Oaks.
$1,399,000

Lots And Land

5558 MARLEON DRIVE, WINDERMERE, Florida 34786

23Picture(s)
0.94Acre
FINAL OPPORTUNITY to build your dream home on one of the last remaining lots in Lake Cypress Cove.
$399,999

Single Family

9912 LAKE LOUISE DRIVE, WINDERMERE, Florida 34786

11Bedroom(s)
14Bathroom(s)
25Picture(s)
25,466Sqft
An exquisite waterfront estate within one of Orlando's most sought after golf community of Isleworth Country Club. This impressive mansion offers car enthusiasts a dream showcase garage that can accommodate collections of 40+ cars.
$23,000,000

Single Family

6409 LAKE BURDEN VIEW DRIVE, WINDERMERE, Florida 34786

6Bedroom(s)
8Bathroom(s)
3Parking(s)
25Picture(s)
8,078Sqft
This Custom French Chateau is a one-of-a-kind dream home, built using high quality materials, finishes and extraordinary craftsmanship throughout. This home is situated on a private corner lot in the Keenes Point subdivision with 270 degrees of amazing Golf & Water Views.
$2,695,000

Single Family

3352 WAX BERRY COURT, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,398Sqft
Meticulously maintained custom built four bedroom, three and one half bath pool home! This distinctive home is perfectly situated on a private cul-de-sac on over an acre of land in butler bay estates of Windermere. This jewel has many recent updates including new interior doors, new wall moldings throughout, and fresh interior/exterior paint.
$679,900

Single Family

13161 LAKE BUTLER BOULEVARD, WINDERMERE, Florida 34786

5Bedroom(s)
5Bathroom(s)
3Parking(s)
25Picture(s)
4,259Sqft
Extraordinary lake front opportunity in Windermere on 1.75 acres! This estate could house a family compound for the individual seeking security and privacy with it's own private gate. A grand entryway leads you to magnificent two story ceilings and welcomes you into a separate living and family room. The home offers 5 bedrooms 3 and 1/2 baths.
$1,675,000

Single Family

7474 FAIRGROVE AVENUE, WINDERMERE, Florida 34786

5Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
3,954Sqft
This five bedroom home is located in the desirable community of Windermere Sound, and looks out onto a large, natural pond. The upstairs features four bedrooms and two bathrooms, each with double sinks, granite counter tops, and shower/tub combo. The main feature of the upstairs is the over-sized open loft, measuring 21' x 26'.
$526,000

Single Family

11824 VINCI DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
4,949Sqft
MODERN ELEGANCE! Outstanding 5 bedrooms, 6 bath home at the reputable Keene's Pointe. It is a must-see property to realize the beauty of true Florida living. Master Bedroom plus 3 en-suites are located downstairs. One full en-suite is upstairs. Master has His and Hers Custom walk in closets.
$1,590,000

Single Family

8917 BLUE MESA DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,914Sqft
Enjoy Magic Kingdom's spectacle firework every night at your front porch in Windermere. This MOVE-IN READY stunning 5 bedrooms, 4 bathrooms, study/den, bonus room, media room with Pond View is your Home to be. This house features open gourmet kitchen with stainless steel appliances , large center island, huge walk-in pantry, Bulter's pantry pass through to the formal Dinning room.
$539,000

Single Family

12833 HOLDENBURY LANE, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,690Sqft
Stunning 4 bedroom Windermere Lakes home with granite kitchen counter tops, crown molding, tray ceilings and a conservation pond view! Enjoy the view from the oversized vaulted ceiling family room, screened porch, and huge master suite! Upgraded appliances and fixtures throughout. Washer and dryer convey.
$399,900

Single Family

9612 CASTLE WAY DR, WINDERMERE, Florida 34786

4Bedroom(s)
5Bathroom(s)
3Parking(s)
25Picture(s)
4,210Sqft
Exceptional custom-built single-story executive estate home with 4 bedrooms, den, bonus room, and spectacular screened pool and spa outdoor oasis. Situated on a premium oversized lot in the exclusive Reserve section of Windsor Hill, this stunningly beautiful and meticulously maintained residence boasts Florida living at its finest.
$1,025,000

Single Family

6705 DUNCASTER STREET, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,925Sqft
Why wait when this home is all you want and more!?!…NOW!!!...Updates,Upgrades and finishing touches dress up every corner of this house. Luxurious 4/3 plus Loft home at LAKES OF WINDERMERE.
$458,900

Single Family

9288 BLANCHE COVE DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
8Bathroom(s)
20Picture(s)
12,778Sqft
Under Construction.
$7,495,000

Single Family

2073 ROBERTS POINT DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
5,641Sqft
Perfectly positioned on a prime 1-acre corner lot in the guard-gated community of Waterford Pointe in Windermere, this exquisite estate stands supreme for its quality, finish, and location. Make a dramatic entrance through the double wooden doors to a showplace of majestic style and elegance. Living and entertaining areas are generous in size and built to impress.
$1,175,000
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