Windermere Homes for Sale

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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.
$3,099,000

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

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

13578 GORGONA ISLE DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,465Sqft
What a deal! Priced for a quick sale! Escape to the Sunshine State today! Be woken by the Disney train in the morning, watch the fireworks overhead every night.
$529,999

Townhouse

6542 MERRICK LANDING BOULEVARD, WINDERMERE, Florida 34786

3Bedroom(s)
3Bathroom(s)
2Parking(s)
12Picture(s)
1,343Sqft
Welcome to Merrick Landing in Windermere. This 3bedroom/3bath townhouse offers 2 master suites and plenty of room for the entire family. The HOA maintains the grounds, as well as, the roof and exterior of the property.
$249,900

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

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

Lots And Land

11811 LAKE BUTLER BOULEVARD, WINDERMERE, Florida 34786

20Picture(s)
1Sqft
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

11824 VINCI DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
4,949Sqft
MODERN ELEGANCE! Furnished 5 bedrooms, 6 bath home at the reputable GOLF community 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. Upstairs you will find 1 full en-suite and a large bonus room with wet bar, microwave and 2 wine coolers. Master has His and Hers Custom walk in closets.
$1,590,000

Lots And Land

12300 MONTALCINO CIRCLE, WINDERMERE, Florida 34786

1Picture(s)
3Acre
Rare opportunity to build your dream home on a lakefront Windermere lot! One of the last county-approved gated communities in Windermere, Casa del Lago ownership will offer more than a beautiful place to build the home of your dreams; it's a lifestyle that you can be proud to call your own.
$660,000

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

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.
$1,399,999

Lots And Land

5582 REMSEN CAY LANE, WINDERMERE, Florida 34786

10Picture(s)
1.94Acre
Eden Hammock * NEW PRICE 12/20/20 ** Beautiful lakefront lot 73' frontage on skiable Lake Speer * Next to park - greenspace area ** Wonderful amenities include lovely conservation with walking trails around ponds, pool, clubhouse area, tennis courts, basketball courts, a workout room, and many playgrounds thru-out the Summerport community ** Great location close to Publix, restaurants, stores, bus
$325,000

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

9288 BLANCHE COVE DRIVE, WINDERMERE, Florida 34786

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

Condominium

8168 BOAT HOOK LOOP, WINDERMERE, Florida 34786

3Bedroom(s)
2Bathroom(s)
25Picture(s)
1,442Sqft
Beautiful first floor condo, corner unit with all appliances and in excellent condition. This Condo is in a great location, just steps to the community pool, gym and rec area...The kitchen features 42" cherry kitchen cabinets, granite counter tops and recessed lighting. All appliances stay, including the washer & dryer.
$235,000

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.
$459,900

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.
$2,950,000

Single Family

6439 MONTCLAIR BLUFF LANE, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
3,080Sqft
Beautiful Large 3000+ sqf house in the exclusive Community of Glenmuir. The well maintained and Gated entrance welcomes you home to one of the finest communities in Windermere. This home boasts many upgrades including granite counter tops in the kitchen, butler pantry, stainless steel appliances. Epoxy/flaked painted garage floor. Huge laundry/utility room with sink.
$511,200

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

4654 RIVER GEM AVENUE, WINDERMERE, Florida 34786

6Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,995Sqft
With top rated schools, tennis, playgrounds, fitness center, fishing docks, lakes and ponds, with nearby shopping and restaurants, it is no wonder that Summerport is recognized as one of Windermere’s most family friendly communities. Your family will have just under 4,000 sq. ft., 6 bedrooms, 4 baths and a huge fenced in yard to entertain and enjoy with friends and family.
$525,000

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

8498 POWDER RIDGE TRAIL, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,393Sqft
Come see the only BUNGALOW of its kind for sale in Windermere Trails! This Corner LOT residence enjoyed many upgrades including a professionally designed outdoor area with a private pool.
$534,990

Single Family

11033 HAWKSHEAD COURT, WINDERMERE, Florida 34786

5Bedroom(s)
4Bathroom(s)
4Parking(s)
25Picture(s)
4,450Sqft
Custom estate home, beautifully appointed and located on a quiet cul-de-sac in sought after Lake Butler Sound. Situated on just under half an acre, this executive home features expansive views, a desirable open floor plan, and luxurious living. Curb appeal abounds with a picture perfect Mediterranean frontage, double wrought iron entry doors with glass insets, and lush tropical landscaping.
$975,000

Single Family

12318 MONTALCINO CIRCLE, WINDERMERE, Florida 34786

5Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
3,764Sqft
You will fall in love with this beautiful home featuring beautiful porcelain vertical tiles, wooden stair case with decorative metal railing and nice private view! Kitchen features beautiful 42 inch white cabinets, Quartz countertops, open eating bar area ,Gourmet kitchen with LG stainless steel appliances with built in oven, microwave and a beautiful Induction stove top as well as butlers pantry
$875,000

Single Family

11440 WILLOW GARDENS DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
5Bathroom(s)
3Parking(s)
25Picture(s)
3,690Sqft
Absolutely stunning elegantly upgraded custom built home with a ½ acre pond view lot in the highly sought Willows at Lake Rhea in the Town of Windermere! Once you walk through the handsome mahogany front doors, a soaring ceiling open to the 2nd floor and a view of the pool and pond beyond you will want to call this home! With all the details you want including unique Palladium windo
$799,000

Single Family

914 W 2ND AVENUE, WINDERMERE, Florida 34786

5Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
7,222Sqft
Stylish chic elegance accentuated by unobstructed, sweeping views of magnificent Lake Butler on the famed Butler Chain of Lakes. Offering arguably the best sights in Olde Windemere from the highly sought-after pristine Butler side of 2nd Ave, this contemporary-style residence features Italian influences, sleek design, and modern sophistication.
$2,899,000

Single Family

12513 BUTLER BAY COURT, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
4,700Sqft
One or more photo(s) has been virtually staged. Exceptional Custom-Built Home in Gated Windermere Club sited on a ½+ acre oversized Corner lot with lush landscaping offers 4700 sq.ft. of generous living area with No Rear neighbors.
$810,000

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

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.
$705,990

Townhouse

7763 FAIRGROVE AVENUE, WINDERMERE, Florida 34786

3Bedroom(s)
3Bathroom(s)
2Parking(s)
1,644Sqft
This is an opportunity you do not want to miss! Beautiful 3 Bedroom, 2.5 Bath townhome in the Lake Sawyer community of Windermere. The well-maintained building and manicured landscaping offers a charming curb-appeal that is sure to catch your eye as you make your way to the home.
$285,000

Condominium

11564 MIZZON DRIVE, WINDERMERE, Florida 34786

3Bedroom(s)
2Bathroom(s)
24Picture(s)
1,332Sqft
Light, bright and open, this 3/2 unit offers a split floor plan for plenty of privacy with a remodelled master closet. Kitchen has Stainless Steel appliances, Silestone countertops, and 42" wood cabinets for plenty of storage. All three bedrooms have new flooring and the bathrooms have been updated. Relax after work with a good book on your screened in balconey.
$225,000

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..
$420,000

Single Family

11456 MISTY OAK ALLEY, WINDERMERE, Florida 34786

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,191Sqft
Come see this beautiful home and it’s from Disney Springs to stories detached garage lots and lots of upgrades AC unit was just maintenance repainted and well-maintained. This property is also minutes from Publix restaurant shopping Center’s great location for a first time home buyer or family even as an investment property.
$379,900

Single Family

7023 KIWANO WAY, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
3,136Sqft
Pre-Construction. To be built. The Sanctuary at Lakes of Windermere is the perfect sanctuary for living in Central Florida’s most desired suburb. The Sanctuary is located in Windermere, FL, on Little Lake Sawyer where just about everything it borders is surrounded by pristine lakes and prestige.
$452,990

Single Family

7022 KIWANO WAY, WINDERMERE, Florida 34786

5Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
3,184Sqft
Pre-Construction. To be built. The Sanctuary at Lakes of Windermere is the perfect sanctuary for living in Central Florida’s most desired suburb. The Sanctuary is located in Windermere, FL, on Little Lake Sawyer where just about everything it borders is surrounded by pristine lakes and prestige.
$462,665

Single Family

7017 KIWANO WAY, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,890Sqft
Pre-Construction. To be built. The Sanctuary at Lakes of Windermere is the perfect sanctuary for living in Central Florida’s most desired suburb. The Sanctuary is located in Windermere, FL, on Little Lake Sawyer where just about everything it borders is surrounded by pristine lakes and prestige.
$442,485

Single Family

7046 KIWANO WAY, WINDERMERE, Florida 34786

3Bedroom(s)
2Bathroom(s)
2Parking(s)
15Picture(s)
2,058Sqft
Pre-Construction. To be built. The Sanctuary at Lakes of Windermere is the perfect sanctuary for living in Central Florida’s most desired suburb. The Sanctuary is located in Windermere, FL, on Little Lake Sawyer where just about everything it borders is surrounded by pristine lakes and prestige.
$389,490

Single Family

11055 BRIDGE HOUSE ROAD, WINDERMERE, Florida 34786

6Bedroom(s)
9Bathroom(s)
4Parking(s)
25Picture(s)
10,452Sqft
WATERFRONT MASTERPIECE ON THE FAMED BUTLER CHAIN OF LAKES! Showcasing grand scale living spaces, unprecedented finishes and resort-style grounds, this privately gated Rial Jones estate captivates at every turn.
$6,400,000

Single Family

11549 CENTER LAKE DRIVE, WINDERMERE, Florida 34786

3Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
2,110Sqft
IMMACULATE one-owner home in the beautiful Lake Burden South community directly facing Center Lake. That being said, let's skip the normal poetic descriptions Realtors are so well known for and jump right into everything you want to know--and nothing you don't. Extremely well taken care of and occupied ONLY by the current owner since new.
$419,000

Single Family

5717 W LAKE BUTLER ROAD, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,582Sqft
As you drive up to the stately two story lakefront traditional with it's mature oaks and lush lawn you know you're home. Situated in Kelso on Lake Butler this home offers the peace and quite of the country just minutes from the Winter Garden Village and other great shopping and restaurants.
$1,500,000

Single Family

11209 MACAW COURT, WINDERMERE, Florida 34786

6Bedroom(s)
7Bathroom(s)
3Parking(s)
25Picture(s)
5,609Sqft
This absolute immaculate 5,500 + square foot Unnerstall custom built home is located in the most desired Windermere community of Keenes Pointe! Perfectly situated overlooking the 4th hole of the Golden Bear Golf Club - Jack Nicklaus signature designed golf course, this home lacks nothing.
$2,100,000

Single Family

13225 ORANGE ISLE DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
2Bathroom(s)
2Parking(s)
14Picture(s)
2,156Sqft
Pre-Construction. To be built. The Sanctuary at Lakes of Windermere is the perfect sanctuary for living in Central Florida’s most desired suburb. The Sanctuary is located in Windermere, FL, on Little Lake Sawyer where just about everything it borders is surrounded by pristine lakes and prestige.
$414,180

Single Family

9615 WESTOVER CLUB CIRCLE, WINDERMERE, Florida 34786

5Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
3,650Sqft
$15k Price reduction!!!! Your search ends here!!! Beautiful 5 Bedrooms and 4 baths pool house featuring front and rear balconies. Breath taking water view in the back with outstanding heated pool/spa for your family enjoy and relax. Kitchen features 42" cabinets, stainless still appliances, work island and walk-in pantry.
$580,000

Lots And Land

11544 WILLOW GARDENS DRIVE, WINDERMERE, Florida 34786

16Picture(s)
2.71Acre
AMAZING OPPORTUNITY TO OWN A BEAUTIFUL WATERFRONT LOT WITH OVER 2 ACRES OF LAND IN THE WILLOWS! The extensive work has been completed to make this one of a kind lot ready to build on! Current owners have completed the Conservation Area Determination and received Conservation Area Authorization Permits from Orange County EPD.
$315,000

Condominium

14450 DESERT HAVEN STREET, WINDERMERE, Florida 34786

3Bedroom(s)
3Bathroom(s)
2Parking(s)
24Picture(s)
2,067Sqft
Beautiful and private end of street unit! Has a gorgeous outdoor oasis, ideal for enjoying the Florida sunshine and taking in a breath of fresh air. The first floor has a nice open floor plan. The master retreat located on the first level has an ensuite bathroom and an oversized closet.
$290,000

Condominium

14153 OASIS COVE BOULEVARD, WINDERMERE, Florida 34786

3Bedroom(s)
3Bathroom(s)
2Parking(s)
15Picture(s)
1,826Sqft
Resort Style Townhome Condominium Gated Community. This 3 Bedroom/2.5 Bath Townhome. There is a Loft/Bonus Room that can easily be used as an office or 4th Bedroom. This home has lots of space, Kitchen Pantry with appliances, inside laundry, upstairs Loft area and a 2 car attached garage. The back patio is covered with a fenced back yard for privacy.
$269,900
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