Windermere, FL Homes

/65
$2,999,999
- 5 Beds
- 4.5 Baths
- 5,005 Sq Ft
12923 Water Point Blvd, Windermere, FL 34786

Welcome to 12923 Water Point Blvd., a stunning lakefront estate nestled in the exclusive, man-guard gated community of Waterford Pointe in Windermere. This impressive residence offers over 5,000 square feet of luxurious living space with 4 bedrooms in the main home, including a spacious primary suite conveniently located on the first floor.Designed for both relaxation and entertaining,

Kevin Sullivan LAKESIDE REALTY WINDERMERE INC

12923 Water Point Blvd, Windermere, FL 34786
/2
$3,100,000 Sold Sep 02, 2025
- 3,923 Sq Ft
- $790/SF
- 58 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2001
11018 Lake Butler Blvd, Windermere, FL 34786

Under contract with contingencies and Backup Offers will be reviewed. Welcome to luxury on Lake Butler Blvd with stunning Wauseon Bay views. This estate spans nearly an acre of landscaped grounds, ideal for relaxation and entertainment. The property features a secondary oversized, air-conditioned garage that could be converted into a guest suite. The main home is a custom-built residence with

Toni Marie Cafferty COMPASS FLORIDA LLC

11018 Lake Butler Blvd, Windermere, FL 34786

/2
Est $704,865 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,201 Sq Ft
13124 Orange Isle Dr, Windermere, FL 34786

13124 Orange Isle Dr, Windermere, FL 34786

/13
$510,000
- 4 Beds
- 2.5 Baths
- 2,139 Sq Ft
11661 Black Rail St, Windermere, FL 34786

This 4 bedroom 2 bathroom house comes with a bonus room that can be used as an office or another bedroom as well. This property has a gorgeous outside area paved with brick, fenced in allowing you to have privacy, detached 2 car garage with a driveway to accommodate more cars. This very popular community has a large open park as well as a play area for kids and a community pool.

Mengshi Lu JOY ESTATE ENTERPRISE INC

11661 Black Rail St, Windermere, FL 34786
/2
$1,870,000 Sold Sep 02, 2025
- 4,351 Sq Ft
- $430/SF
- 20 Days On Market
- 5 Beds
- 5.5 Baths
- Built 2002
6149 Blakeford Dr, Windermere, FL 34786

Experience luxury, comfort, and timeless design in this spacious 5-bedroom, 5.5-bathroom pool home with an office, game room loft, and over 4,350 square feet of beautifully appointed living space. Perfectly positioned in the sought-after, guard-gated community of Keene’s Pointe, this residence offers privacy, prestige, and picture-perfect views.Step inside to an open-concept floor plan

Brynn Munro CORCORAN PREMIER REALTY

6149 Blakeford Dr, Windermere, FL 34786

/16
Est $320,803 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,512 Sq Ft
14214 Desert Haven St Unit 3604, Windermere, FL 34786

14214 Desert Haven St Unit 3604, Windermere, FL 34786

/9
$785,000
- Land
- 1.44 Acres
- $545,139 per Acre
0 Quail Cove Ct, Windermere, FL 34786

Welcome to Quail Cove Court—an exceptional opportunity to own 1.44 acres in the highly sought-after Windermere area. Nestled within the desirable Windermere Downs community yet not subject to an HOA, this homesite offers privacy, flexibility, and the freedom to design and build your dream residence with the builder of your choice.The property is well-positioned at the end of a quiet

Alexis Anderson REGENCY REAL ESTATE LLC

0 Quail Cove Ct, Windermere, FL 34786
/2
$5,150,000 Sold Aug 29, 2025
- 6,448 Sq Ft
- $799/SF
- 65 Days On Market
- 6 Beds
- 6.5 Baths
- Built 1989
1455 Kelso Blvd, Windermere, FL 34786

Discover 11,699 sqft of total luxury at 1455 Kelso Blvd, a stunning lakefront estate in Windermere’s Kelso on Lake Butler community. Set on nearly an acre with 119 feet of frontage on Lake Butler, this fully renovated 6-bedroom, 6.5-bath home offers over 6,448 sqft of living square footage. Features include a gourmet kitchen, first-floor primary suite with lake views, an attached in-law suite

Julie Sanchez THE REAL ESTATE COLLECTION LLC

1455 Kelso Blvd, Windermere, FL 34786

/60
Est $749,057 Not Listed For Sale
- 5 Beds
- 4 Baths
- 3,365 Sq Ft
13431 Swansea Ave, Windermere, FL 34786

13431 Swansea Ave, Windermere, FL 34786

/45
$938,000
- 4 Beds
- 3.5 Baths
- 3,315 Sq Ft
8724 Peachtree Park Ct, Windermere, FL 34786

Experience the magic of Windermere living at Peachtree Park a boutique enclave of just 28 homes, located directly across the street from Walt Disney World! This rare community blends exclusivity, charm, and convenience, offering the perfect setting for both everyday comfort and unforgettable moments. Crafted by Ashton Woods, this Bimini model radiates elegance and functionality at every turn.

Marcelo Machado LA ROSA REALTY LLC

8724 Peachtree Park Ct, Windermere, FL 34786
/2
$370,000 Sold Aug 29, 2025
- 2,067 Sq Ft
- $179/SF
- 102 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2013
14430 Desert Haven St Unit 4302, Windermere, FL 34786

WHAT A BEAUTIFUL TOWNHOME WITH NO REAR NEIGHBORS IN THE GORGEOUS COMMUNITY OF OASIS COVE. This home features three Bedrooms, two and a half bathrooms, a den, loft, two car garage and a brick paver patio. When entering into this beautiful townhome you will notice granite counter tops and dark cherry cabinets in the kitchen with stainless steel appliances, pendant lighting, can lighting and tile

Pam Eddy COLDWELL BANKER HUBBARD HANSEN

14430 Desert Haven St Unit 4302, Windermere, FL 34786

/61
Est $2,551,066 Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 4,953 Sq Ft
2516 Windermere Reserve Ct, Windermere, FL 34786

2516 Windermere Reserve Ct, Windermere, FL 34786

/47
$4,900,000
- 5 Beds
- 4.5 Baths
- 5,548 Sq Ft
5036 Latrobe Dr, Windermere, FL 34786

Within the gates of the renowned Isleworth Golf & Country Club, this beautiful lakefront estate captures the essence of timeless luxury and gracious living. Poised on the shores of Lake Bessie, the 5,548 square-foot residence unfolds across two levels, designed to frame sweeping water views and create effortless spaces for both grand entertaining and quiet retreat. The upper level greets guests

Monica Lochmandy ISLEWORTH REALTY LLC

5036 Latrobe Dr, Windermere, FL 34786
/2
$365,000 Sold Aug 29, 2025
- 1,826 Sq Ft
- $200/SF
- 84 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2007
8031 Enchantment Dr Unit GE, Windermere, FL 34786

MOTIVATED SELLER! Welcome to the GATED Windermere Community of Oasis Cove a first class community in Central Florida, founded in 2007, where residents live amidst the tranquil magic of our adventurous surroundings. 2 stories, 3-bedroom, 2.5-bath, and features a Loft and Flex Room Upstairs with the Primary Suite Downstairs. Downstairs, you will find an inviting Open Floor Plan with tile and

Sean Flatley KELLER WILLIAMS REALTY AT THE PARKS

8031 Enchantment Dr Unit GE, Windermere, FL 34786

/40
Est $763,803 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,304 Sq Ft
8705 Lookout Pointe Dr, Windermere, FL 34786

8705 Lookout Pointe Dr, Windermere, FL 34786

/73
$2,999,999
- 6 Beds
- 6.5 Baths
- 5,882 Sq Ft
12720 Jacob Grace Ct, Windermere, FL 34786

Tucked inside one of Windermere’s most exclusive guard-gated communities, this extraordinary custom-built estate is more than a home — it’s a destination. With almost 6000sq. ft., six bedrooms, six and a half baths, a detached in-law suite, and nearly two acres of pristine lakefront land, it represents the pinnacle of Central Florida luxury. Set on a quiet cul-de-sac, the residence blends

Irhelma Pieterse STOCKWORTH REALTY GROUP

12720 Jacob Grace Ct, Windermere, FL 34786
/2
$940,000 Sold Aug 29, 2025
- 3,318 Sq Ft
- $283/SF
- 174 Days On Market
- 4 Beds
- 4 Baths
- Built 2001
11474 Claymont Cir, Windermere, FL 34786

Exceptional Opportunity to own a David Weekley Home. Step into this stunning 4-bedroom, 4-bathroom home, featuring a spacious bonus room and a dedicated study. Located in the highly sought-after community of Keene's Pointe, this property offers both comfort and luxury. Upon entering, you’re greeted by a bright and open living/dining room combo, seamlessly flowing into the kitchen and breakfast

Gonzalo Senior IRM INVEST., REAL EST.& MGMT.

11474 Claymont Cir, Windermere, FL 34786

/2
Est $531,933 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,211 Sq Ft
7742 Brofield Ave, Windermere, FL 34786

7742 Brofield Ave, Windermere, FL 34786

/50
$2,850,000
- 5 Beds
- 6.5 Baths
- 6,248 Sq Ft
8402 Lake Burden Cir Unit 2, Windermere, FL 34786

Experience luxury waterfront living in the prestigious guard gated community of Keene's Pointe. This custom estate offers over 6,000 sq ft of elegant living space with 5-bedroom ensuites and a full pool bath with shower and powder room off of the Theater. A chef's kitchen with stainless-steel appliances, gas range with additional built-in oven and microwave. The gourmet kitchen opens to the

Toni Marie Cafferty COMPASS FLORIDA LLC

8402 Lake Burden Cir Unit 2, Windermere, FL 34786
/2
$889,288 Sold Aug 28, 2025
- 2,687 Sq Ft
- $331/SF
- 25 Days On Market
- 4 Beds
- 3 Baths
- Built 2025
14366 Crest Palm Ave, Windermere, FL 34786

One or more photo(s) has been virtually staged. Sample Images Arlington Floorplan – 2,687 Sq. Ft. | 4 Beds | 3 Baths | 2.5-Car Garage | Oversized Lot | Move-In Ready. Welcome to the Arlington – a thoughtfully designed, single-story home by Dream Finders Homes that perfectly blends luxury, functionality, and comfort. This brand new 2,687 square foot residence sits on an oversized lot, offering

Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

14366 Crest Palm Ave, Windermere, FL 34786

/20
Est $438,199 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,912 Sq Ft
13731 Beringer St, Windermere, FL 34786

13731 Beringer St, Windermere, FL 34786

/45
$739,000
- 5 Beds
- 3 Baths
- 2,972 Sq Ft
6965 Tettenhall Ln, Windermere, FL 34786

Welcome to own this beautiful home in lakes of windermere . 5 bedrooms 3 full bathrooms that has been remodeled . Marble floor through downstairs and laminate upstairs and a lot of upgrades throughout the house . The house is looking over a stunning view of a pond with a water fountain and looking everyday at the Disney fireworks . Perfectly situated minutes from all the attractions Disney ,

Nabil Chakrouni VISION HOME REAL ESTATE, LLC

6965 Tettenhall Ln, Windermere, FL 34786
/2
$680,000 Sold Aug 28, 2025
- 2,620 Sq Ft
- $260/SF
- 8 Days On Market
- 4 Beds
- 2.5 Baths
- Built 2006
4445 Blue Major Dr, Windermere, FL 34786

Stunning Pool Home with Water View and No Rear Neighbors in Sought-After Summerport in Windermere, FL. Welcome to your dream home in the heart of Windermere’s highly desirable Summerport community! This spacious 4-bedroom, 2.5-bathroom home offers 2,620 sq ft of beautifully updated living space and is perfectly situated on one of the most private lots in the neighborhood—with tranquil

Candace Tulensru WORTH CLARK REALTY

4445 Blue Major Dr, Windermere, FL 34786

/77
Est $654,636 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,224 Sq Ft
8355 Vivaro Isle Way, Windermere, FL 34786

8355 Vivaro Isle Way, Windermere, FL 34786

/40
$625,000
- 5 Beds
- 2.5 Baths
- 2,759 Sq Ft
6891 Northwich Dr, Windermere, FL 34786

One or more photo(s) has been virtually staged. Nestled within Lakes of Windermere sits a 5 bedroom, 2.5 bath Craftsman inspired home. The welcoming front yard with flowing ground cover, shade providing magnolias, and flowering plants is located just across from the community pool, recreational greenspace, and tennis court. The convenience and enjoyment of such amenities without the upkeep. You

Ashley Wilt TITAN REALTY GROUP LLC

6891 Northwich Dr, Windermere, FL 34786
/2
$1,122,346 Sold Aug 28, 2025
- 4,222 Sq Ft
- $266/SF
- 0 Days On Market
- 6 Beds
- 4 Baths
- Built 2025
14378 Crest Palm Ave, Windermere, FL 34786

Under Construction. Sample Image Experience the perfect blend of elegance, comfort, and practicality with this beautifully crafted new home in Windermere. Every element of this residence has been thoughtfully designed to create a space that feels both luxurious and inviting. With soaring ceilings—up to 10 feet on the first floor and 9 feet on the second (as per plan)—and luxury ceramic tile

Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

14378 Crest Palm Ave, Windermere, FL 34786

/34
Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,117 Sq Ft
6043 Savannah Oak Alley, Windermere, FL 34786

6043 Savannah Oak Alley, Windermere, FL 34786

/44
$575,000
- 4 Beds
- 2 Baths
- 2,063 Sq Ft
9056 Woodbreeze Blvd, Windermere, FL 34786

***NO REAR NEIGHBORS - POND VIEW - HUGE COVERED BACK PATIO - MASSIVE 2 CAR GARAGE - HUGE WHITE PORCELAIN TILES - NEXT TO TENNIS COURT!!Great opportunity to own this well-maintained 4-bedroom, 2-bath home with a 2-car garage in the desirable Silver Woods community. From the moment you arrive, you’ll notice the lush landscaping and paver walkway leading to the front entrance. Inside, the

Milton James COLDWELL BANKER RESIDENTIAL RE

9056 Woodbreeze Blvd, Windermere, FL 34786
/2
$850,000 Sold Aug 27, 2025
- 2,560 Sq Ft
- $332/SF
- 64 Days On Market
- 4 Beds
- 3 Baths
- Built 2002
6321 Clearmeadow Ct, Windermere, FL 34786

SALE FELL THROUGH - BACK ON MARKET - THEIR LOSS - YOUR GAIN! Stunning 4 Bed, 3 Bath Pool Home in Gated Glenmuir! Located on a quiet cul-de-sac, this beautifully updated single-story home features a 2025 primary bath remodel with marble floors, modern tile shower, double vanity, and light-up mirror. The home features a thoughtfully designed split floor plan with 4 spacious bedrooms, a private

Kiran Khan KELLER WILLIAMS CLASSIC

6321 Clearmeadow Ct, Windermere, FL 34786

/2
Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,168 Sq Ft
12514 Summer Port Beach Way, Windermere, FL 34786

12514 Summer Port Beach Way, Windermere, FL 34786

/67
$4,650,000
- 5 Beds
- 5.5 Baths
- 7,183 Sq Ft
12540 Park Ave, Windermere, FL 34786

Offering a prime lakefront location along the shores of Lake Butler in the esteemed gated community of Chaine du Lac, this distinguished estate features timeless architecture paired with transitional interiors and gorgeous views to showcase Windermere lakefront living at its finest. The estate has been elevated with significant recent improvements, including a brand-new roof, an all-new primary

Carey Sheffield ISLEWORTH REALTY LLC

12540 Park Ave, Windermere, FL 34786
/2
$735,000 Sold Aug 26, 2025
- 2,464 Sq Ft
- $298/SF
- 4 Days On Market
- 4 Beds
- 3 Baths
- Built 2013
12973 Holdenbury Ln, Windermere, FL 34786

Welcome to your dream home, where location, luxury, and tranquility meet! Nestled on a private conservation water-view lot, this move-in-ready pool home offers the perfect balance of serenity and elegance. Boasting 4 bedrooms, a den, and 3 full baths, this home is thoughtfully designed to meet your every need. Upon entry, you're greeted by a spacious, inviting foyer, adorned with beautiful

Robert Foutz ASSIST 2 SELL FOUTZ REALTY

12973 Holdenbury Ln, Windermere, FL 34786

/37
Est $2,397,712 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 4,685 Sq Ft
6127 Orta Ct, Windermere, FL 34786

6127 Orta Ct, Windermere, FL 34786

/61
$3,800,000
- 3 Beds
- 3.5 Baths
- 4,751 Sq Ft
9648 Mccormick Place, Windermere, FL 34786

Stunning golf and lake views and beautifully updated grounds are hallmarks of this elegant Isleworth estate. Nestled along the front nine overlooking Isleworth’s 2nd fairway and beautiful Lake Chase, this two-story home spans more than 4,800 square feet and features modern finishes throughout. Beautiful porcelain tile travels throughout the main level from the spacious living room with an

Carey Sheffield ISLEWORTH REALTY LLC

9648 Mccormick Place, Windermere, FL 34786
/2
$1,400,000 Sold Aug 26, 2025
- 4,075 Sq Ft
- $344/SF
- 72 Days On Market
- 4 Beds
- 3 Baths
- Built 2004
13710 Lake Cawood Dr, Windermere, FL 34786

One or more photo(s) has been virtually staged. * UNDER CONTRACT & ACCEPTING BACK UP OFFERS * Fully renovated luxury home in Gated Lake Cawood, prime Windermere location! This stunning four-bedroom, three-bath estate—complete with a spacious bonus room—offers a blend of luxury, comfort and location. On a full acre in the exclusive gated community of Lake Cawood, just across the street from

Jules Carneir PREMIER SOTHEBYS INT'L REALTY

13710 Lake Cawood Dr, Windermere, FL 34786

/37
Est $423,631 Not Listed For Sale
- 4 Beds
- 3 Baths
- 1,760 Sq Ft
8368 Iron Mountain Trail, Windermere, FL 34786

8368 Iron Mountain Trail, Windermere, FL 34786

/63
$975,000
- 4 Beds
- 3.5 Baths
- 3,235 Sq Ft
8778 Peachtree Park Ct, Windermere, FL 34786

Live the ultimate Orlando lifestyle in this stunning 8-year-old home, perfectly situated just outside the back entrance to Disney and minutes from top dining, shopping, highways, and all of Orlando's attractions Backing up to a peaceful conservation area, you'll enjoy complete privacy with no rear neighbors-- a rare find in this area! The HOA fee even includes lawn maintenance, so your yard stays

Erica Diaz HOMEVEST REALTY

8778 Peachtree Park Ct, Windermere, FL 34786
/2
$390,000 Sold Aug 25, 2025
- 1,565 Sq Ft
- $249/SF
- 26 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2010
12884 Calderdale Ave, Windermere, FL 34786

Stunning End Unit Townhome with Pond Views in Windermere!Welcome to this beautifully maintained 3-bedroom, 2.5-bath end unit in the heart of Windermere, offering peaceful pond views and a host of recent upgrades. Enjoy outdoor living on the large screened lanai with UV-proof epoxy flooring, perfect for relaxing or entertaining. The detached 2-car garage and concrete driveway provide ample

Shirley Botansky RE/MAX PRIME PROPERTIES

12884 Calderdale Ave, Windermere, FL 34786

/50
Est $547,520 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,214 Sq Ft
7861 Berkshire Oak Alley, Windermere, FL 34786

7861 Berkshire Oak Alley, Windermere, FL 34786

/62
$1,950,000
- 5 Beds
- 4 Baths
- 4,489 Sq Ft
13420 Bonica Way, Windermere, FL 34786

Experience the Florida lifestyle in this stunning FULLY FURNISHED 5-Bed/4-Bath pool home on over 1/2-acre, with a welcoming open floor plan spanning 4,500 square feet, spectacular Theater Room, custom upgrades and designer accents throughout, and new AC system in August 2025. Situated across from the community park and tennis on one of the best waterfront lots in sought-after gated Tildens Grove,

Frank Ferrell FERRELL REALTY, INC.

13420 Bonica Way, Windermere, FL 34786

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