Homes for Sale in Windermere

Windermere offers home buyers the exclusivity associated with some of Florida’s finest established communities, with a quaint historic downtown and easy access to Dr. Phillip’s world class dining and entertainment. The Erica Diaz Team offers tremendous insight into Windermere’s real estate market, offering unmatched knowledge and access to off-market homes.

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$2,395,000

73 OAKDALE ST
WINDERMERE, Florida

4Bedroom(s)
3Bathroom(s)
58Picture(s)
4,267Sqft
Discover the pure enjoyment of a Renaissance home handcrafted by artisans and nestled along the edges of Lake Down, one of the largest of the Butler Chain of Lakes, in the very quaint Town of Windermere.

$1,849,000

12224 MCKINNON ROAD
WINDERMERE, Florida

4Bedroom(s)
4Bathroom(s)
53Picture(s)
3,777Sqft
One acre of Windermere lakefront living, with no HOA! This home is perfect, and currently configured, for multi-generational living. Downstairs there is a master bedroom with en-suite master bathroom, along with large guest bedroom and hallway full bathroom. This together with classically appointed living room, dining room, Florida room, and open kitchen.

$6,474,000

6474 DEACON CIRCLE
WINDERMERE, Florida

6Bedroom(s)
5Bathroom(s)
67Picture(s)
5,859Sqft
New Price - Sellers have found another home, are motivated to sell and open to negotiating. rnStep into this updated waterfront estate situated along the shores of the famed Butler Chain of Lakes. The airy Mediterranean-style two-story is an ideal lakefront getaway for everyday living and to entertain family and friends.

$1,675,000

1230 KELSO BOULEVARD
WINDERMERE, Florida

4Bedroom(s)
3Bathroom(s)
54Picture(s)
3,563Sqft
Spectacular One of a Kind Estate in the highly sought after Kelso on Lake Butler Community in Windermere. Situated on just over an acre, this lushly landscaped property features private deeded access to the Butler Chain of Lakes - soaring cathedral ceilings - floor-to-ceiling windows - double master suites - beautiful pool and lanai and a multitude of unique architectural features.

$4,250,000

732 2ND AVENUE
WINDERMERE, Florida

5Bedroom(s)
4Bathroom(s)
60Picture(s)
5,685Sqft
Custom designed lakefront home with private guest apartment that takes in the beauty of Lake Butler and the Butler Chain of Lakes.

$885,000

2131 KANE PARK WAY
WINDERMERE, Florida

4Bedroom(s)
3Bathroom(s)
38Picture(s)
2,523Sqft
Executive Living awaits you in the TOWN of Windermere (an exclusive enclave of homes within approximately 2.2 sq miles) with access to its private boat ramp on the Pristine Butler Chain of Lakes! Perfectly positioned on over half an acre of land on a cul-de-sac in WILLOWS at LAKE RHEA is a 4 bedroom, 3 bathroom, 3 car garage, pool/spa NEWLY REMODELED AND RENOVATED custom home with over 2500 ft.

$1,695,000

6289 BLAKEFORD DRIVE
WINDERMERE, Florida

4Bedroom(s)
3Bathroom(s)
48Picture(s)
3,816Sqft
The perfect house! The perfect place! The perfect size and perfect price! Welcome! Classic design never goes out of style -- 4BR/3 BR/2HA baths PLUS office PLUS bonus room PLUS enormous enclosed pool, spa and summer kitchen on a gorgeous pond lot with large community park as your neighbor! All this located in the guard gated golf course country club community of Keene’s Pointe! Ref

$669,000

5006 RIVER GEM AVENUE
WINDERMERE, Florida

4Bedroom(s)
3Bathroom(s)
63Picture(s)
2,713Sqft
Stop in the name of love…because you will love this house! The most open floorplan and the highest elevation single story home located in Summerport. This picturesque home will be sure to check every box on the list. From the moment you step through the front door you will be greeted with natural light from the oversized windows.

$445,000

8655 COVENTRY PARK WAY
WINDERMERE, Florida

3Bedroom(s)
2Bathroom(s)
23Picture(s)
1,676Sqft
One or more photo(s) has been virtually staged. Come see this charming 3 bedroom, 2.5 bathroom home now on the market! You’ll enjoy preparing meals in the gorgeous kitchen with sleek counters, tiled backsplash, stainless appliances, and beautiful spacious cabinetry. Primary bathroom features a separate tub and shower, dual sinks and a spacious closet.

$2,750,000

2511 RESERVE WINDERMERE COURT
WINDERMERE, Florida

5Bedroom(s)
5Bathroom(s)
21Picture(s)
5,175Sqft
Pre-Construction. To be built. Introducing the "CHASE" constructed by ELEMENT HOME BUILDERS in the heart of Windermere in a small enclave of eight custom, estate homes. A five bedroom, office, game room, gym, loft , summer kitchen and pool with a three car garage will not disappoint. The home is detailed with a wine room, walk in pantry and fireplace.

$699,895

6207 RIVER FRUIT COURT
WINDERMERE, Florida

3Bedroom(s)
2Bathroom(s)
27Picture(s)
1,796Sqft
BEAUTIFUL HOME ON 1/4 ACRE CONSERVATION and POND VIEW LOT IN GATED EDEN ISLE! NO FRONT OR REAR NEIGHBORS, park/green space & gazebo across street! Home oozes curb appeal w/BEAUTIFUL landscaping, inviting front porch & covered entry, NEW exterior paint 2013 & architectural shingle roof! RELAX on LARGE EXTENDED SCREENED patio w/SLATE floors & WET BAR w/wood cabinets overlooking GORGE

$3,595,000

11000 BRIDGE HOUSE ROAD
WINDERMERE, Florida

6Bedroom(s)
7Bathroom(s)
57Picture(s)
9,046Sqft
Formerly featured on the Street of Dreams, this stunning home will make you feel like you’re at a luxury resort in Bermuda. Designed by Mark Nasralla and built by Ray Coudriet, this one-of-a-kind residence is perfectly positioned on over one acre in the 24-hour guard-gated community of Lake Butler Sound.

$2,674,480

2030 BELLAMERE COURT
WINDERMERE, Florida

5Bedroom(s)
6Bathroom(s)
7Picture(s)
5,097Sqft
Under Construction. Last opportunity to own a brand-new home in Windermere’s boutique Bella Vita neighborhood, a small enclave of just 11 half acre home sites.

$479,000

13742 CALERA ALLEY
WINDERMERE, Florida

3Bedroom(s)
2Bathroom(s)
54Picture(s)
1,912Sqft
This charming townhouse immediately impresses with a lovely brick paver lead walk and a spacious front porch. Inside, you’ll discover airy 9-ft. 4-in. ceilings along with a half bath and convenient laundry room on the first floor. The open concept kitchen features 42-in. upper cabinets, a bonus 12-in.

$589,999

4913 WINDERMERE AVENUE
KISSIMMEE, Florida

4Bedroom(s)
3Bathroom(s)
21Picture(s)
1,914Sqft
New with Tiled Flooring and an Upgraded Furniture Package, this Townhome boasts both class and fun including Flat Screen TV’s with cable in all bedrooms and a private Splash Pool.rnrnThe downstairs open floor plan offers a Dining area with seating for 6, Breakfast Bar seating for 4, reclined sofa, 55” Flat Screen Smart Tv, modern kitchen.

$1,574,999

13508 BELLARIA CIRCLE
WINDERMERE, Florida

4Bedroom(s)
4Bathroom(s)
68Picture(s)
3,769Sqft
Price drop! Welcome home to Bellaria, a small gated enclave in the heart of Windermere. Zoned for excellent schools and with quick access to everywhere. This Brierhill Custom Home offers a bright open, floorplan, all one one level, with space where you need it and plenty of storage. Found on 3/4 of an acre, and with a fully fenced Backyard this is definitely the home you have been waiting for.

$1,000,000

8336 VIVARO ISLE WAY
WINDERMERE, Florida

6Bedroom(s)
4Bathroom(s)
32Picture(s)
3,640Sqft
Located close to 429, Disney and Hamlin Shops, this beautiful 6 bedrooms, 4 bath home features a tile roof, wood-look tile flooring, large loft, and kitchen. Move-in ready pool home in Windermere Isle.The sliding glass door leads to a covered porch, custom built SALT WATER POOL with gas heater, screened enclosure and a fully fenced backyard.

$2,650,000

11502 WATERSTONE LOOP DRIVE
WINDERMERE, Florida

4Bedroom(s)
4Bathroom(s)
79Picture(s)
4,447Sqft
THIS IS IT! THE RARE GEM YOU HAVE BEEN WAITING FOR! ALL BEDROOMS ARE ON FIRST FLOOR! COME TOUR THIS GUARD GATED MAJESTIC WINDERMERE ESTATE ON THE BEST AND MOST LUXURIOUS STREET IN WATERSTONE WHERE ESTATES ARE SELLING FOR UPWARDS OF $12 MILLION DOLLARS. HOMES RARELY COME ON THE MARKET ON THIS STREET.

$1,250,000

3443 WILD MYRTLE COURT
WINDERMERE, Florida

5Bedroom(s)
3Bathroom(s)
40Picture(s)
2,918Sqft
Newly renovated executive home on 1.2 acre homesite in Old Windermere. This charming 5 bedroom 3 bath pool home has it all. In addition to the formal living room with whitewashed brick faced wood burning fireplace this plan offers a generous 26’x23’ family room and office.

$890,000

5944 CAYMUS LOOP
WINDERMERE, Florida

4Bedroom(s)
3Bathroom(s)
61Picture(s)
2,984Sqft
$30,000 Price Reduction, great one owner home located in the 24 HR Guard Gated community of Keenes Pointe, a sought after Jack Nicklaus Golf Course neighborhood and tucked adjacent to the Butler Chain of Lakes you will find this beauty. Owner takes great pride in this 4BR/3BTH estate.

$1,349,500

11040 CLIPPER COURT
WINDERMERE, Florida

4Bedroom(s)
4Bathroom(s)
25Picture(s)
3,545Sqft
Here is an exceptional opportunity to live in the established Town of Windermere! NO HOA! 4 bedroom, 4 bath, two story pool home with wood burning fireplace and vaulted ceiling on over an acre of land! Oversized master with 2 bathrooms! An enormous sitting area w/den that can also make the perfect family room or use the whole area as a one bedroom in-law suite.

$879,000

2106 WILLOW BRICK ROAD
WINDERMERE, Florida

4Bedroom(s)
3Bathroom(s)
67Picture(s)
2,545Sqft
If you enjoy gardening or simply enjoy the peace, quiet and privacy of beautiful gardens, then check out this incredible property with six patios and winding paths. Home is Move-In ready! Owner is transferring out of state.

$519,995

11619 BLACK RAIL STREET
WINDERMERE, Florida

3Bedroom(s)
2Bathroom(s)
12Picture(s)
1,828Sqft
This beautiful home is for sale in exclusive Windermere area! This is a high rated energy star house. This home is just minutes away from multiple lakes, sought after grade A schools, outdoor activities, and easy access to dining, shopping, and attractions. The house is a spacious 3 bedroom 2.

$1,034,000

1712 LAKE ROBERTS COURT
WINDERMERE, Florida

5Bedroom(s)
4Bathroom(s)
46Picture(s)
3,463Sqft
Gorgeous sunsets & tranquility are yours in this lake view beauty located in gated Windermere Club on Lake Roberts. Lushly landscaped very private .55 acre lot at end of cul de sac! Stunning 5/4.5 newly painted pool home has panoramic lake & serene sunset views from the large Master Suite, Liv Rm, KIT & Fam Rm. Paved front porch leads into bright Foyer, w/volume ceilings.
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