Windermere, FL Homes

/52
$3,295,000
- 5 Beds
- 5.5 Baths
- 5,845 Sq Ft
11255 Macaw Ct, Windermere, FL 34786

Experience sweeping views of the golf course and tranquil sunsets over Lake Burden — along with a front-row seat to nightly Disney fireworks—from this beautifully reimagined residence in the guard-gated Keene’s Pointe neighborhood. Designed with transitional interiors, this five-bedroom, five-and-a-half-bath home blends warm textures, clean lines, and an effortless connection to its natural

Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

11255 Macaw Ct, Windermere, FL 34786
/43
$13,500 per month
- 3 Beds
- 3 Baths
- 3,247 Sq Ft
- House for Rent
9742 Green Island Cove, Windermere, FL 34786

Nestled along the shores of beautiful Lake Louise within the gates of Isleworth Golf & Country Club, this charming golf villa offers a prime lakefront location in proximity to the Clubhouse. The interior boasts more than 3,000 square feet of living space, with an open floor plan set against a backdrop of picturesque water views. Elegant hardwood floors travel throughout the single-story floor

Monica Lochmandy ISLEWORTH REALTY LLC

9742 Green Island Cove, Windermere, FL 34786
/2
$1,150,000 Sold Mar 26, 2025
- Land
- 1.53 Acres
- $751,634 per Acre
- 6 Days On Market
0 Westover Roberts Rd Unit MFRO6286777, Windermere, FL 34786

Discover an unparalleled opportunity to build your dream luxury estate on this rare, untouched lakefront lot in the heart of Windermere, Florida. Spanning 87 acres, Lake Olivia is a private, spring-fed, sandy-bottom lake with no public access, ensuring a peaceful and exclusive setting. The lake is renowned for its professional-grade slalom course, shielded by surrounding hills that provide ideal

Christopher Lyons AGILE GROUP REALTY

0 Westover Roberts Rd Unit MFRO6286777, Windermere, FL 34786

/41
Est $1,533,386 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,538 Sq Ft
11845 Waterstone Loop Dr, Windermere, FL 34786

11845 Waterstone Loop Dr, Windermere, FL 34786

/38
$330,000
- 3 Beds
- 2 Baths
- 1,442 Sq Ft
8256 Maritime Flag St Unit 103, Windermere, FL 34786

**LUXURIOUS LAKESIDE LIVING**Tucked into the heart of Windermere’s desirable Lakeside at Lakes of Windermere community, this first-floor, corner unit condo at **8256 Maritime Flag St #103 (Unit 1710)** delivers an ideal blend of privacy, accessibility, and vibrant resort-style amenities. With no stairs to climb, this ground-floor location offers added convenience for everyday living,

Brad Rosel EXP REALTY LLC

8256 Maritime Flag St Unit 103, Windermere, FL 34786
/23
$4,500 per month
- 3 Beds
- 2 Baths
- 1,353 Sq Ft
- House for Rent
3278 Downs Cove Rd, Windermere, FL 34786

Welcome to your waterfront paradise on the beautiful Windermere Chain of Lakes! This 3 Bed, 2 Bath, 1,351 htd. sqft lake home sits on a 0.29-acre lot overlooking Lake Down, one of 13 lakes on the Butler Chain of Lakes. As you enter the front door you are greeted by an open floorplan, panoramic views, split bedroom layout, renovated kitchen and baths, ceramic wood-look tiling and adorning wood

John Goggin STOCKWORTH REALTY GROUP

3278 Downs Cove Rd, Windermere, FL 34786
/2
$2,800,000 Sold Mar 26, 2025
- 7,239 Sq Ft
- $387/SF
- 18 Days On Market
- 5 Beds
- 8 Baths
- Built 2007
9632 Weatherstone Ct, Windermere, FL 34786

Welcome to your serene custom estate, offering unobstructed water views at every turn, situated on the shores of Lake Olivia within the gated community of Weatherstone. Just minutes from downtown Windermere and Orlando's premier attractions, this property combines luxury and convenience. As you approach, a circular paver driveway and stunning Florida landscaping set the stage for elegance.

Matt Tomaszewski CORCORAN PREMIER REALTY

9632 Weatherstone Ct, Windermere, FL 34786

/16
Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,060 Sq Ft
8112 Buena Vista Resort Dr Unit 2303, Orlando, FL 32821

8112 Buena Vista Resort Dr Unit 2303, Orlando, FL 32821

/25
$820,000
- 6 Beds
- 4 Baths
- 3,648 Sq Ft
7180 Beek St, Windermere, FL 34786

Spacious 6-Bedroom Home Just Minutes from Disney! Discover the perfect blend of space, comfort, and convenience in this stunning Hayden floorplan by Pulte Homes, located in the highly sought-after Windermere Terrace community. This beautifully maintained home offers 6 bedrooms + a bonus room, 4 full bathrooms, and a 3-car garage — ideal for growing families or hosting guests. A private guest

Maria Ubillus FOLIO REALTY LLC

7180 Beek St, Windermere, FL 34786
/50
$9,500 per month
- 5 Beds
- 7 Baths
- 4,845 Sq Ft
- House for Rent
11415 Waterstone Loop Dr, Windermere, FL 34786

Luxury Home for Rent in Exclusive Windermere, FL !!! Don’t miss this incredible opportunity to live in one of Windermere’s most prestigious gated communities! This stunning 5-bedroom, 7-bathroom estate features elegant formal living and dining areas, a private home office, two spacious family rooms, and a game room with a built-in bar. Enjoy private access to Windermere Preparatory School,

Carola Garcia De Montenegro AGENT TRUST REALTY CORPORATION

11415 Waterstone Loop Dr, Windermere, FL 34786
/2
$680,000 Sold Mar 25, 2025
- 3,050 Sq Ft
- $223/SF
- 7 Days On Market
- 4 Beds
- 3 Baths
- Built 2006
12931 Droxford Rd, Windermere, FL 34786

One or more photo(s) has been virtually staged. Welcome to this fabulous Ashton Woods-built home, offered for the first time by the original owners. Lovingly cared for, this 4-bedroom, 3-bath home with a loft is filled with exquisite architectural details. Upon entering through the updated glass front door, you'll be greeted by a grand foyer featuring a sweeping staircase. A bedroom and full bath

Sherri Palmer EXP REALTY LLC

12931 Droxford Rd, Windermere, FL 34786

/26
Est $556,604 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,178 Sq Ft
4325 Blue Major Dr, Windermere, FL 34786

4325 Blue Major Dr, Windermere, FL 34786

/62
$4,200,000
- 5 Beds
- 8 Baths
- 6,248 Sq Ft
11002 Lake Butler Blvd, Windermere, FL 34786

Lakefront Living in the Heart of Windermere – A Rare Opportunity for Multigenerational LuxurySituated along the tranquil, open waters of Wauseon Bay—part of the world-renowned Butler Chain of Lakes—this expansive estate on prestigious Lake Butler Boulevard is more than just a home: it’s a lifestyle destination, purposefully designed to inspire connection, relaxation, and recreation. With

Sean Oakley SERENDIPITY REALTY LLC

11002 Lake Butler Blvd, Windermere, FL 34786
/18
$11,000 per month
- 3 Beds
- 3 Baths
- 2,646 Sq Ft
- House for Rent
6131 Payne Stewart Dr, Windermere, FL 34786

Looking for a luxurious home in a prime location? Look no further! Located in the Isleworth Country Club, this Stunning single-family home at 6131 Payne Stewart Dr. is now available for rent. Situated in a fantastic waterfront location on Lake Chase, which is part of the Butler Chain of Lakes, this home is a short walk away from the world-renowned Isleworth Golf and Country Club. With

Jill Irwin IRWIN REALTY GROUP LLC

6131 Payne Stewart Dr, Windermere, FL 34786
/2
$1,180,000 Sold Mar 25, 2025
- 2,450 Sq Ft
- $482/SF
- 18 Days On Market
- 4 Beds
- 3 Baths
- Built 1986
3302 Just-A-mere Ct, Windermere, FL 34786

Beautifully maintained and upgraded by current owner, this charming family home is located in the highly sought after Windermere Town and has access to the BUTLER CHAIN OF LAKES! Secluded, private lot of over an acre creating oodles of potential for those looking to substantially extend the current home or build the home of their dreams! Ample parking and plenty of space to store your boat

Sue Webb WATSON REALTY CORP.

3302 Just-A-mere Ct, Windermere, FL 34786

/45
Est $440,691 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,539 Sq Ft
11951 Vermillion Ave, Windermere, FL 34786

11951 Vermillion Ave, Windermere, FL 34786

/57
$1,900,000
- 5 Beds
- 4.5 Baths
- 3,759 Sq Ft
11139 Camden Park Dr Unit 5, Windermere, FL 34786

Discover unparalleled luxury in this stunning 5-bedroom, 4.5-bathroom estate nestled within the prestigious Keene's Pointe country club community in Windermere, Florida. Perfectly positioned along the second hole and green of the renowned Golden Bear Club, this turn-key golf course home offers breathtaking views and an exceptional lifestyle for discerning buyers. Step inside to find high-end

Shane Croft COLDWELL BANKER RESIDENTIAL RE

11139 Camden Park Dr Unit 5, Windermere, FL 34786
/25
$10,500 per month
- 4 Beds
- 3.5 Baths
- 4,097 Sq Ft
- House for Rent
9525 Lavill Ct, Windermere, FL 34786

Located on Lake Down of the Butler Chain of Lakes lies this custom-built 4 bed, 3.5 bath, 4,097 square foot pool home. Sitting on two acres with southern lakefront exposure, enjoy spectacular views of both sunrise and sunset over Lake Butlers Chain of Lakes. Upon entering the home you are greeted to a wonderful view of the lake through the two story cathedral windows in the grand living area with

John Goggin STOCKWORTH REALTY GROUP

9525 Lavill Ct, Windermere, FL 34786
/2
$846,500 Sold Mar 25, 2025
- 2,728 Sq Ft
- $310/SF
- 254 Days On Market
- 5 Beds
- 3 Baths
- Built 1990
2119 Willow Brick Rd, Windermere, FL 34786

Welcome Home! You will fall in love with this exquisite home located in the highly sought after Willows of Lake Rhea subdivision located in the hear of Windermere. This house is on .71 acers of pure relaxation. Since there are no neighbors right behind you the quiet green belt makes you feel you are secluded from the outside world. Once you open the doors to this home you are captivated by

Stacey Jurek EXP REALTY LLC

2119 Willow Brick Rd, Windermere, FL 34786

/35
Est $397,395 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,852 Sq Ft
8174 Enchantment Dr Unit 1601, Windermere, FL 34786

8174 Enchantment Dr Unit 1601, Windermere, FL 34786

/100
$3,750,000
- 4 Beds
- 3.5 Baths
- 5,273 Sq Ft
10577 Down Lakeview Cir, Windermere, FL 34786

This exceptional lakefront home is located on The Butler Chain of Lakes with 137 feet of pristine shoreline and is situated on almost one dry acre. At first glance you will immediately fall in love with this beautiful custom home boasting amazing panoramic views and nightly Disney fireworks. The circular paved drive flanked with mature oak trees welcome you home to a covered porch and an

Simon Simaan THE SIMON SIMAAN GROUP

10577 Down Lakeview Cir, Windermere, FL 34786
/5
$3,400 per month
- 5 Beds
- 4.5 Baths
- 2,807 Sq Ft
- House for Rent
11774 Via Lucerna Cir Unit 1, Windermere, FL 34786

Nice and quiet established neighborhood of Windermere, Orlando Florida gated community.Few miles away to Universal Studios Disney food shopping. 1/2 bathroom at screened porch with a faucet and sink and a shower where you can do barbecue with the family at the porch.

Perlita Aquino PAPP REALTY, INC.

11774 Via Lucerna Cir Unit 1, Windermere, FL 34786
/2
$1,341,633 Sold Mar 25, 2025
- 4,222 Sq Ft
- $318/SF
- 343 Days On Market
- 6 Beds
- 4 Baths
- Built 2024
14297 Crest Palm Ave, Windermere, FL 34786

One or more photo(s) has been virtually staged. Pre-Construction. To be built. *Images shown are for illustrative purposes only*Arlington Bonus - Our AWARD Winning 2 story home with 6 Bedrooms and 4 Baths. This great floor plan boasts an open concept family/dining/kitchen area with a gourmet kitchen, extended 42" wrap around cabinets, and an extended island. The owner's bath also contains a spa

Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

14297 Crest Palm Ave, Windermere, FL 34786

/58
Est $787,337 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,365 Sq Ft
6929 Corley Ave, Windermere, FL 34786

6929 Corley Ave, Windermere, FL 34786

/50
$925,000
- 4 Beds
- 2.5 Baths
- 2,856 Sq Ft
9676 Wild Oak Dr, Windermere, FL 34786

Welcome to Windermere Downs. Nestled in one of the most sought after neighborhoods in Windermere, this 70’s modern gem sits on a half acre lot. The U shaped layout of the house wraps around a generous screened lanai under a permanent roof with four skylights. The lanai is accessible from the foyer, primary bedroom, guest room, dining room, and family room and it opens up to the swimming pool and

Hardy Edwards, III BHHS FLORIDA REALTY

9676 Wild Oak Dr, Windermere, FL 34786
/30
$3,000 per month
- 4 Beds
- 3.5 Baths
- 1,936 Sq Ft
- Townhouse for Rent
8745 Via Tavoleria Way, Windermere, FL 34786

WINDERMERE FULLY FURNISHED - Corner lot - 2 Master suites with walk-in closets, one of them with a balcony - total of 4 Bed, 3 Bath, a Powder Bath, Loft area, Front Porch, Fenced back patio with covered Lanai, pavers, 2-car garage. Water Softner Salt System available. Community Swimming POOL is just across the street and Disney Fireworks is a must see. EXTREMELY WELL LOCATED, GREAT SCHOOL

Claudia Panella COLDWELL BANKER REALTY

8745 Via Tavoleria Way, Windermere, FL 34786
/2
$1,137,874 Sold Mar 25, 2025
- 3,663 Sq Ft
- $311/SF
- 142 Days On Market
- 5 Beds
- 4 Baths
- Built 2024
14273 Crest Palm Ave, Windermere, FL 34786

One or more photo(s) has been virtually staged. Pre-Construction. To be built. *Images shown are for illustrative purposes only*Arlington Bonus - Our AWARD Winning 2 story home with 5 Bedrooms and 4 Baths. This great floor plan boasts an open concept family/dining/kitchen area with a gourmet kitchen, extended 42" wrap around cabinets, and an extended island. The owner's bath also contains a spa

Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

14273 Crest Palm Ave, Windermere, FL 34786

/24
Est $720,868 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,013 Sq Ft
6764 Bridgewater Village Rd, Windermere, FL 34786

6764 Bridgewater Village Rd, Windermere, FL 34786

/60
$2,590,000
- 5 Beds
- 6.5 Baths
- 6,000 Sq Ft
11055 Ullswater Ln, Windermere, FL 34786

Luxury Meets Comfort in This Stunning Custom Windermere Estate! Experience the pinnacle of Florida living in this immaculate home, designed with elegance and functionality in mind. Spanning an impressive 6,000 square feet, this single-story masterpiece boasts exceptional architectural details, intricate ceiling designs, and luxurious finishes throughout. Step through the grand wrought iron and

John Crescenti LOKATION

11055 Ullswater Ln, Windermere, FL 34786
/27
$3,450 per month
- 5 Beds
- 4.5 Baths
- 2,874 Sq Ft
- House for Rent
1125 Lascala Dr, Windermere, FL 34786

Mediterranean style property with five bedrooms, four and a half bathrooms on two floors in gated community. One of the bedrooms is on the first floor next to a full bathroom, making it ideal to function as an office or guest suite. The remaining bedrooms are on the second floor with the master bedroom having crown molding and a huge walk-in closet. Fully equipped kitchen with granite

Charles Woolley BHHS FLORIDA REALTY

1125 Lascala Dr, Windermere, FL 34786
/2
$540,000 Sold Mar 24, 2025
- 2,151 Sq Ft
- $251/SF
- 2 Days On Market
- 3 Beds
- 2 Baths
- Built 2004
12919 Freeman St, Windermere, FL 34786

Welcome to the quiet, tree-lined community of Lakes of Windermere! Wellington model on a premium oversized Pie shaped lot with a very lovely private fenced in back yard. The additional enclosure added to the lanai and the large open great room makes for great entertaining. You will enter through a beautiful Entry Point door into the open formal living and dining room w/crown molding. Your study

Diane Rogers KELLER WILLIAMS ELITE PARTNERS III REALTY

12919 Freeman St, Windermere, FL 34786

/37
Est $522,760 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,222 Sq Ft
11091 Bagley Alley, Windermere, FL 34786

11091 Bagley Alley, Windermere, FL 34786

/39
$520,000
- 3 Beds
- 2 Baths
- 2,058 Sq Ft
13324 Longacre Dr, Windermere, FL 34786

This amazing and spacious one-story home features 3 bedrooms, 2 baths plus large office space. This single-family house offers 42" cabinets, granite countertops, stainless steel appliances. The laundry room is oversized, with a laundry tub for convenience. This home is located at the community of Windermere Terrace in Windermere. Community has plenty of amenities, including swimming pool with

James Song MULTI CHOICE REALTY LLC

13324 Longacre Dr, Windermere, FL 34786
/2
$2,400 per month
- 3 Beds
- 2.5 Baths
- 1,429 Sq Ft
- Townhouse for Rent
12547 Cruxbury Dr, Windermere, FL 34786

**For Rent: Charming Townhouse in Windermere - Close to Disney!**Discover this fantastic townhouse featuring 3 spacious bedrooms located on the upper level and 2.5 well-appointed bathrooms. Enjoy brand new vinyl plank flooring and fresh carpeting throughout. The kitchen comes fully equipped with all essential appliances, and a washer and dryer are included for your convenience.Step outside to a

Eric Weigand CQ ORLANDO REALTY INC

12547 Cruxbury Dr, Windermere, FL 34786
/2
$393,000 Sold Mar 24, 2025
- 1,545 Sq Ft
- $254/SF
- 8 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2012
12202 Langstaff Dr, Windermere, FL 34786

Charming townhouse in Windermere! 3 br, 2.5 baths, Corner lot and end unit with no rear neighbor, full of natural lighting and unparalleled tranquility, featuring a private and fenced courtyard. Nice modern upgraded flooring and color scheme. Beautiful Community pool and kiddie park. This home is so conveniently located close to Disney, mayor shopping & dining spots, that you will find almost

Milagros Agostini-Prado AK GLOBAL REALTY LLC

12202 Langstaff Dr, Windermere, FL 34786

/31
Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,476 Sq Ft
8265 Maritime Flag St Unit 22b-5, Windermere, FL 34786

8265 Maritime Flag St Unit 22b-5, Windermere, FL 34786

/59
$9,995,000
- 6 Beds
- 9 Baths
- 9,571 Sq Ft
6137 Grosvenor Shore Dr, Windermere, FL 34786

Experience luxury lakefront living on a grand scale in this custom-built Modern Mediterranean estate on Lake Tibet, part of the pristine Butler Chain of Lakes. The three-story residence spans 9,571 square feet of living space on over 2.2 acres in the guard-gated community of Keene’s Pointe in sought-after Windermere. Built by Goehring & Morgan, this architectural masterpiece offers refined

Mick Night PREMIER SOTHEBY'S INTL. REALTY

6137 Grosvenor Shore Dr, Windermere, FL 34786
/2
$430,000 Sold Mar 24, 2025
- 1,974 Sq Ft
- $218/SF
- 31 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2014
8757 Via Tavoleria Way, Windermere, FL 34786

One or more photo(s) has been virtually staged. MOTIVATED SELLER! PRICE DROPPED TO SELL QUICKLY! This Carrington townhome offers 1,974 square feet of living space with 3 bedrooms and 2.5 bathrooms, right behind Disney World! The main floor features an expansive living room, dining area, large kitchen island with granite counter-tops, and stainless-steel appliances. Upstairs, you will find an

Nathan Jacoby YOUNG REAL ESTATE

8757 Via Tavoleria Way, Windermere, FL 34786

/25
Est $392,511 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,840 Sq Ft
14324 Desert Haven St Unit 4001, Windermere, FL 34786

14324 Desert Haven St Unit 4001, Windermere, FL 34786

/57
$699,900
- 3 Beds
- 2 Baths
- 2,074 Sq Ft
1412 Glenwick Dr, Windermere, FL 34786

Florida Living at its finest! Priced below recent appraisal, this wonderful barrel tiled roof, single story home is move-in ready and waiting for you! You’ll feel the pride of ownership both inside and out in this lovely 3 bedroom, 2 bath, pool home; located in the exclusive 24 hr. guard-gated community -The Reserve at Belmere in Windermere, FL. Upon entering, you’ll see features such as 10’

Chris Bunnell WATSON REALTY CORP

1412 Glenwick Dr, Windermere, FL 34786

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