Windermere, FL Homes

/43
$340,000
- 3 Beds
- 2 Baths
- 1,442 Sq Ft
8179 Maritime Flag St Unit 202-108, Windermere, FL 34786

Welcome to Lakeside at Lakes of Windermere! This beautifully updated first-floor condo combines comfort, style, and convenience?located just minutes from the Disney parks and directly across the street from Lakeside Village Center, offering shopping, dining, and everyday amenities. Step inside to find luxury vinyl flooring in all bedrooms with no carpet, fresh interior paint, and elegant crown

Naf Zaman THE FIRM RE

8179 Maritime Flag St Unit 202-108, Windermere, FL 34786
/49
$5,900 per month
- 4 Beds
- 3 Baths
- 3,190 Sq Ft
- House for Rent
307 W 4th Ave, Windermere, FL 34786

Executive rental pool home located in the charming town of Windermere! The location is just two block from Main st and all that downtown Windermere has to offer! This single-story, 4-bedroom (2 primary bedrooms), 3-bathroom home, sits on an oversized corner lot in the shade of majestic oak trees. Enjoy a gourmet kitchen featuring stainless steel appliances, two brand new refrigerators, a

Katie Bray MAINFRAME REAL ESTATE

307 W 4th Ave, Windermere, FL 34786
/45
$900,000 Sold Sep 05, 2025
- 2,868 Sq Ft
- $314/SF
- 104 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2000
6125 Foxfield Ct, Windermere, FL 34786

Popular Keene's Pointe in Windermere! 24 Hour attendant gated community. Located on the 1st Fairway, this beautiful 4 Bedroom, 3 1/2 Baths Villa Style home will not disappoint. Primary Bedroom with a expansive bathroom, along with 2 other bedrooms with en-suite baths are all located on the 1st floor. 1 Bedroom with 1/2 bath upstairs. Large open Dinng and Living Room overlook the screened

Mary Ann Thompson RE/MAX Solutions

6125 Foxfield Ct, Windermere, FL 34786

/61
Est $1,063,839 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 4,176 Sq Ft
8361 Torcello Isle Dr, Windermere, FL 34786

8361 Torcello Isle Dr, Windermere, FL 34786

/53
$1,085,000
- 4 Beds
- 3.5 Baths
- 3,423 Sq Ft
8764 Lookout Pointe Dr, Windermere, FL 34786

Experience all the MAGIC that living in Windermere has to offer with DISNEY FIREWORK VIEWS from your private pool deck every night! Waterviews, Florida Pines, blue skies, and palm trees right in your own backyard. A true outdoor oasis with TRAVERTINE TILE pool deck, a shady covered lanai, pool and spa with water feature, a FENCED YARD, and a miniature golf PUTTING GREEN! Located in Windermere

Ken Pozek REAL BROKER, LLC

8764 Lookout Pointe Dr, Windermere, FL 34786
/2
$3,100 per month
- 3 Beds
- 2.5 Baths
- 2,203 Sq Ft
- House for Rent
13094 Kegan St, Windermere, FL 34786

Beautifully remodeled home for rent in the highly desirable community of Windermere Sound! ? This spacious property offers 3 bedrooms, 2.5 bathrooms, and a bright open layout perfect for modern living. The updated kitchen features new appliances, quartz countertops, and elegant finishes. Enjoy your mornings on the screened patio overlooking a peaceful pond and your evenings in a community

Angela Mavarez Suarez PM ELITE REALTY LLC

13094 Kegan St, Windermere, FL 34786
/2
$6,800,000 Sold Sep 05, 2025
- 8,691 Sq Ft
- $782/SF
- 141 Days On Market
- 5 Beds
- 6.5 Baths
- Built 2002
6126 Kirkstone Ln, Windermere, FL 34786

Nestled within the highly sought after, guard-gated community of Lake Butler Sound, this breathtaking lakefront estate has been completely remodeled with designer interior and exterior finishes, offering an unparalleled blend of sophistication and modern luxury. Positioned on an expansive corner lot, this home boasts breathtaking panoramic lake views from nearly every room, creating a serene and

Christopher Christensen COMPASS FLORIDA LLC

6126 Kirkstone Ln, Windermere, FL 34786

/40
Est $518,383 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,107 Sq Ft
13856 Summerport Trail Loop, Windermere, FL 34786

13856 Summerport Trail Loop, Windermere, FL 34786

/55
$3,350,000
- 5 Beds
- 4 Baths
- 6,834 Sq Ft
4301 Down Point Ln, Windermere, FL 34786

One or more photo(s) has been virtually staged. Selected photo(s) are virtually staged. UNIQUE & LUXURIOUS WATER-FRONT-LAKE property, showcasing a MEDITERRANEAN COTTAGE DESIGN with a custom HEATED POOL. This luxurious & HOA FREE home offers BREATHTAKING VIEWS OF THE LAKE! Imagine yourself enjoying this unique home featuring 5 x bedrooms and 4 x bathrooms, along with a 2-car garage capable of

Augusto Rodriguez-Aponte MARK SPAIN REAL ESTATE

4301 Down Point Ln, Windermere, FL 34786
/2
$8,500,000 Sold Sep 05, 2025
- 11,403 Sq Ft
- $745/SF
- 206 Days On Market
- 7 Beds
- 13 Baths
- Built 2013
5271 Isleworth Country Club Dr, Windermere, FL 34786

Welcome to this grand residence nestled on a sprawling 1.17 acre lot originally hand selected by golf legend Arnold Palmer. Perfectly positioned to capture breathtaking views of the first and tenth holes, this remarkable estate provides a lifestyle of unmatched elegance and comfort.Meticulously maintained, this grand estate encompasses 11,403 square feet of living space thoughtfully

Monica Lochmandy ISLEWORTH REALTY LLC

5271 Isleworth Country Club Dr, Windermere, FL 34786

/43
Est $725,135 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,419 Sq Ft
8711 Lookout Pointe Dr, Windermere, FL 34786

8711 Lookout Pointe Dr, Windermere, FL 34786

/55
$1,045,000
- 4 Beds
- 3.5 Baths
- 3,248 Sq Ft
11162 Ledgement Ln, Windermere, FL 34786

NEW TILE ROOF INSTALLED BEFORE CLOSING! Welcome to Glenmuir—one of Windermere’s most sought-after gated communities. This 4 bedroom, 3 full bath, plus 2 half bath home includes a dedicated office and an upstairs bonus room within a primarily single-story layout—a thoughtful blend of functionality and comfort.Double doors open to a bright foyer with immediate views of the custom 2021

Deb Schroeder INFINITY REALTY GROUP LLC

11162 Ledgement Ln, Windermere, FL 34786
/2
$2,400,000 Sold Sep 05, 2025
- 5,111 Sq Ft
- $470/SF
- 708 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1993
800 W 2nd Ave, Windermere, FL 34786

Detached Guest Suite overlooking Pool with Fireplace has Private Entrance in Courtyard - Courtyard Pool with Waterfall from the Heated Spa has the feel of an Olde World European Resort - Formal Living Room with Fireplace - Formal Dining Room with Fireplace - Family Room with Fireplace - Large Kitchen with Wine Cellar and Pantry in the Heart of the Home has incredible views of the Pool & Lake -

Darrell Nunnelley VINTAGE REALTY GROUP LLC

800 W 2nd Ave, Windermere, FL 34786

/37
Est $437,539 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,756 Sq Ft
13477 Gorgona Isle Dr, Windermere, FL 34786

13477 Gorgona Isle Dr, Windermere, FL 34786

/19
$3,000,000
- Land
- 1.02 Acres
- $2,941,176 per Acre
12213 Park Ave, Windermere, FL 34786

Welcome to Chaine Du Lac- one of Windermere's most exclusive gated enclaves. This prime 1.02-acre cul-de-sac lot is one of only TWO homesites remaining among just 44 custom-built estate residences, offering a rare opportunity to design your private luxury retreat. The property is cleared, level, and fully equipped with utilities, making it truly build-ready. Enjoy the tranquility of oversized

Naresh Budhu PREMIUM PROPERTIES R.E. SERVICE

12213 Park Ave, Windermere, FL 34786
/2
$1,750,000 Sold Sep 04, 2025
- 5,284 Sq Ft
- $331/SF
- 2 Days On Market
- 6 Beds
- 4.5 Baths
- Built 2004
5137 Tildens Grove Blvd, Windermere, FL 34786

Discover refined luxury in the guard-gated Tildens Grove community. This custom-built, traditional-style residence spans approximately 5,300 sqft across a prime .64 acre lot backing to a serene conservation pond. Boasting 6 bedrooms and 41⁄2 baths, the home offers exceptional craftsmanship and thoughtful updates throughout. The gourmet kitchen is a chef’s dream—featuring a large center island,

Laura Senzamici ENGEL & VOLKERS ORLANDO DR PHILLIPS

5137 Tildens Grove Blvd, Windermere, FL 34786

/95
Est $856,115 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 3,407 Sq Ft
11947 Otterbrooke Trail, Windermere, FL 34786

11947 Otterbrooke Trail, Windermere, FL 34786

/31
$950,000
- 4 Beds
- 3.5 Baths
- 3,080 Sq Ft
11314 Ledgement Ln Unit 1, Windermere, FL 34786

Located in the exclusive, gated Glenmuir community, this beautifully appointed residence offers refined living with timeless style. A grand entrance through glass French doors leads to an open floor plan adorned with elegant ceramic tile. The gourmet kitchen is a chef’s dream, featuring 42" cabinetry, stainless steel appliances, an oversized island, custom tile backsplash, and a walk-in butler’s

Mark Vescio MARK SPAIN REAL ESTATE

11314 Ledgement Ln Unit 1, Windermere, FL 34786
/2
$535,000 Sold Sep 04, 2025
- 2,230 Sq Ft
- $240/SF
- 25 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2005
6830 Mapperton Dr, Windermere, FL 34786

Wow, what a wonderful home to return to everyday that has Beautiful Views of the Pine Tree Forest located across the street. Enjoy sipping lemonade on your Front Porch with this Unobstructed View of Nature! Once inside you will be greeted by the Vibrant Colors throughout and an Abundance of Large Windows making this home Light and Bright. The split bedroom feature is ideal. With 2 bedrooms

Kristin Haughwout-Osorio PARKSIDE PROPERTIES, LLC

6830 Mapperton Dr, Windermere, FL 34786

/42
Est $686,163 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,935 Sq Ft
11813 Cave Run Ave, Windermere, FL 34786

11813 Cave Run Ave, Windermere, FL 34786

/75
$3,600,000
- 5 Beds
- 6.5 Baths
- 5,501 Sq Ft
5024 Sawyer Cove Way, Windermere, FL 34786

Welcome to “The Sounding:” a captivating lakefront estate residence with inviting water views and a serene and peaceful setting offering the best of Florida living. Tucked inside this privately gated and intimate enclave of estate homes across the street from Windermere Prep, Sawyer Sound offers an escape from the ordinary and this showplace residence sets the standard for lakefront living. A

Rob Rahter STOCKWORTH REALTY GROUP

5024 Sawyer Cove Way, Windermere, FL 34786
/2
$450,000 Sold Sep 04, 2025
- 1,904 Sq Ft
- $236/SF
- 74 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2018
11037 Bagley Alley, Windermere, FL 34786

Welcome to this 3bedroom, 2.5 bathroom, two-story home in the community of Westside Village in Windemere . This home features an open concept with a living, kitchen, and dining room. The kitchen boasts granite countertops, stainless steel appliances, backsplash, 42" upper cabinets, and a breakfast bar. The second floor features a spacious primary bedroom and a private bathroom with double vanity

Eric Jia NUMBER 1 BROKER, LLC

11037 Bagley Alley, Windermere, FL 34786

/92
Est $2,117,210 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 5,023 Sq Ft
11817 Vinci Dr, Windermere, FL 34786

11817 Vinci Dr, Windermere, FL 34786

/48
$369,500
- 3 Beds
- 2.5 Baths
- 1,720 Sq Ft
7407 Ripplepointe Way, Windermere, FL 34786

Welcome to 7407 Ripplepointe Way – Windermere’s Best Townhome Value! Price just improved and the seller is motivated — offering a $10,000 credit to help with closing costs, buying down your rate, or even refreshing the home with new paint or carpet! Tucked away in the highly sought-after Lake Burden community, this charming townhome is ready for its next chapter. Featuring a beautifully designed

Mahmoud Mango DALTON WADE INC

7407 Ripplepointe Way, Windermere, FL 34786
/2
$490,000 Sold Sep 04, 2025
- 1,696 Sq Ft
- $289/SF
- 102 Days On Market
- 3 Beds
- 2 Baths
- Built 2012
12751 Calderdale Ave, Windermere, FL 34786

Beautiful home with park views offering maintenance free living with HOA dues covering roof replacement, exterior painting and front lawn/shrub maintenance. The interior has fresh paint, vinyl wood plank flooring was just installed, and the exterior has been painted recently. You'll love the open layout with a large great room opening out from the gourmet island kitchen with granite and stainless

Hojin Chang RE/MAX PRIME PROPERTIES

12751 Calderdale Ave, Windermere, FL 34786

/29
Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,840 Sq Ft
14264 Desert Haven St Unit GE, Windermere, FL 34786

14264 Desert Haven St Unit GE, Windermere, FL 34786

/75
$3,700,000
- 4 Beds
- 3 Baths
- 5,365 Sq Ft
2844 Marquesas Ct, Windermere, FL 34786

Welcome to your private sanctuary, where every sunrise and sunset dances over the shimmering waters of Lake Crescent. Nestled within the exclusive gated community of Lake Crescent Reserve, this lakefront masterpiece offers just under 6,000 square feet of newly remodeled, reimagined luxury living. Positioned on a pristine oversized lot surrounded by lush landscaping and majestic oak trees, the

Dianna Desboyaux EXP REALTY LLC

2844 Marquesas Ct, Windermere, FL 34786
/2
$1,000,000 Sold Sep 03, 2025
- 3,646 Sq Ft
- $274/SF
- 64 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1989
1947 Broadleaf Ct, Windermere, FL 34786

One or more photo(s) has been virtually staged. Welcome to 1947 Broadleaf Court – a beautifully maintained 5-bedroom, 3.5-bath home located in the highly sought-after Windermere Downs community. Nestled on nearly half an acre in a peaceful cul-de-sac, this spacious 3,646 sq ft residence offers the perfect blend of comfort, elegance, and Florida lifestyle.Step inside to discover a light-filled

Kevin Sullivan LAKESIDE REALTY WINDERMERE INC

1947 Broadleaf Ct, Windermere, FL 34786

/30
Est $492,162 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,058 Sq Ft
13347 Overstreet Rd, Windermere, FL 34786

13347 Overstreet Rd, Windermere, FL 34786

/65
$5,325,000
- 4 Beds
- 5.5 Baths
- 6,424 Sq Ft
5243 Isleworth Country Club Dr, Windermere, FL 34786

Presenting a magnificent Isleworth golf front estate with sweeping lake views, perched above holes #2 and #9 and Lake Chase, combining a completely reimagined interior with designer elegance and modern grand style. With no neighbors on three sides, this stunning home offers a unique combination of privacy mixed with rare golf and water vistas. Home recently underwent a major “spare no expense”

Rob Rahter STOCKWORTH REALTY GROUP

5243 Isleworth Country Club Dr, Windermere, FL 34786
/2
$370,000 Sold Sep 03, 2025
- 1,479 Sq Ft
- $250/SF
- 95 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2008
7348 Yoder St, Windermere, FL 34786

Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom townhome with a private courtyard and detached garage, nestled in the sought-after Lake Burden community of Windermere, Florida. Boasting high ceilings, rich wood flooring, and an expansive outdoor courtyard, this move-in-ready residence offers both comfort and style. Located in the heart of Windermere, you'll enjoy unbeatable access

Christopher Gabriel EXP REALTY LLC

7348 Yoder St, Windermere, FL 34786

/10
Not Listed For Sale
Lot 2 Down Park Ln, Windermere, FL 34786

Lot 2 Down Park Ln, Windermere, FL 34786

/64
$6,970,000
- 5 Beds
- 8 Baths
- 7,529 Sq Ft
9349 Tibet Pointe Cir, Windermere, FL 34786

Set along the pristine shores of Lake Tibet Butler, this remarkable Keene’s Pointe estate is a showpiece of enduring craftsmanship and thoughtful design. Every element of its 7,500+ sq ft reflects meticulous attention to detail and a level of care that defines timeless luxury living. The elevated foyer overlooks the formal dining and living areas—an elegant introduction defined by

Jay Martin CORCORAN PREMIER REALTY

9349 Tibet Pointe Cir, Windermere, FL 34786
/2
$975,000 Sold Sep 02, 2025
- 3,455 Sq Ft
- $282/SF
- 7 Days On Market
- 5 Beds
- 4 Baths
- Built 2001
6084 Caymus Loop, Windermere, FL 34786

Keene’s Pointe - your opportunity to live in this beautiful community for a great price! Located on the 13th green of The Golden Bear Club, this one owner home offers a functional and spacious floor plan with 5 bedrooms and 4 baths. The first floor has a kitchen/great room area with gas fireplace, formal living and dining rooms, a bedroom with walk-in closet that can also be used as an office

Teresa Stewart SOUTHERN REALTY GROUP LLC

6084 Caymus Loop, Windermere, FL 34786

/18
Est $752,406 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,010 Sq Ft
9207 Reflection Pointe Dr, Windermere, FL 34786

9207 Reflection Pointe Dr, Windermere, FL 34786

/58
$949,000
- 5 Beds
- 3.5 Baths
- 3,662 Sq Ft
13224 Swansea Ave, Windermere, FL 34786

A Must-See Windermere Gem in the Sought-After Providence Neighborhood - This beautiful home, set on an expansive estate-sized lot with tranquil water views and no front or rear neighbors, is on the market for the very first time. - A charming front porch with tongue & groove wood accented ceilings and overhead fans offers a warm welcome and the perfect place to relax. - Step inside to a timeless

Darrell Nunnelley VINTAGE REALTY GROUP LLC

13224 Swansea Ave, Windermere, FL 34786
/2
$350,000 Sold Sep 02, 2025
- 1,155 Sq Ft
- $303/SF
- 30 Days On Market
- 2 Beds
- 2 Baths
- Built 2004
14241 Confetti Dr, Windermere, FL 34786

Paradise Awaits - This one-story corner townhouse is located at Summerport in Windermere. Walking distance to Keenes Crossing Elementary School. Open concept, kitchen with Samsung stainless appliances and luxury COREtec Vinyl Flooring throughout the property. Primary with walk-in closet and dual vanity. Outdoor Oasis - Large yard, fully paved with custom hardscaping - perfect for entertaining or

Lenise De Carvalho CENTURY 21 CARIOTI

14241 Confetti Dr, Windermere, FL 34786

/34
Est $527,360 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,115 Sq Ft
6620 Bridgewater Village Rd, Windermere, FL 34786

6620 Bridgewater Village Rd, Windermere, FL 34786

/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

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