Windermere, FL Homes

/44
$999,000
- 4 Beds
- 3 Baths
- 2,357 Sq Ft
8525 Bowden Way, Windermere, FL 34786

Keene's Pointe - 24-hour gated/attended community in Windermere, Florida. 4 bedroom/3 bath home with formal living and dining rooms, kitchen and great room. This quaint home features a functional floor plan. Kitchen with newer stainless appliances, open concept floor plan joining the kitchen, nook and great room and private primary with walk-in closet and bath with dual vanities, shower and

Teresa Stewart SOUTHERN REALTY GROUP LLC

8525 Bowden Way, Windermere, FL 34786
/2
$600,000 Sold Dec 15, 2025

12925 Holdenbury Ln, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,981 Sq Ft
- Built 2013
Last Sold Summary
- 4% Below List Price
- $201/SF
- 98 Days On Market
Last Listing Agent Eric Nelson SIGNATURE HOMES

12925 Holdenbury Ln, Windermere, FL 34786

/36
Est $418,074 Not Listed For Sale

11618 Water Run Aly, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,584 Sq Ft
- Built 2017
11618 Water Run Aly, Windermere, FL 34786

Last Sold Summary
- 4% Below List Price
- $275/SF
- 116 Days On Market
- Last Sold Price $435,000
- Feb 09, 2024
Last Listing Agent Deena Carvajal THE CARVAJAL GROUP

/35
$534,900 Pending
- 3 Beds
- 2 Baths
- 2,058 Sq Ft
13312 Longacre Dr, Windermere, FL 34786

Under contract-accepting backup offers. Move in ready Windermere Terrace home just minutes from Walt Disney World, featuring a large flex room, screened lanai, and private fenced backyard!Recently refreshed home offering a functional layout with a spacious, versatile flex area ideal for a home office, playroom, or studio. Enjoy Central Florida living with a screened lanai overlooking a

Mariesy Davila LA ROSA REALTY INTERNACIONAL L

13312 Longacre Dr, Windermere, FL 34786
/2
$619,000 Sold Dec 18, 2025

8776 Crescendo Ave, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,072 Sq Ft
- Built 2016
Last Sold Summary
- $299/SF
- 4 Days On Market
Current Estimated Value $619,101

Last Listing Agent Matt Kester THE REAL ESTATE COLLECTION LLC

8776 Crescendo Ave, Windermere, FL 34786

/33
Est $508,343 Not Listed For Sale

13874 Summerport Trail Loop, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 2,233 Sq Ft
- Built 2016
13874 Summerport Trail Loop, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $236/SF
- 266 Days On Market
- Last Sold Price $525,880
- Jun 13, 2024
Last Listing Agent xingzhi zhang AAA GLOBAL VENTURES PA

/34
$689,000
- 5 Beds
- 3 Baths
- 2,511 Sq Ft
13232 Longacre Dr, Windermere, FL 34786

Wonderful home in desired Windermere. This two-story home features five large bedrooms and 3 bathrooms and a spacious 2 car garage. Designed with an open floor plan has a large living and dining area and a kitchen with lots of cabinets and pantry.The main floor offers 2 first-floor bedrooms for added convenience and flexibility, for guests or multipurpose room/office plus pantry and storage

Maria Kronenberg CHARLES RUTENBERG REALTY ORLANDO

13232 Longacre Dr, Windermere, FL 34786
/2
$450,000 Sold Apr 23, 2026

8601 Via Tavoleria Way, Windermere, FL 34786
- 3 Beds
- 3.5 Baths
- 1,936 Sq Ft
- Built 2014
Last Sold Summary
- 3% Below List Price
- $232/SF
- 5 Days On Market
Last Listing Agent Liza Farzati SERHANT

8601 Via Tavoleria Way, Windermere, FL 34786

/47
Est $364,567 Not Listed For Sale

14005 Oasis Springs Ln Unit 906, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,786 Sq Ft
- Built 2010
14005 Oasis Springs Ln Unit 906, Windermere, FL 34786

Last Sold Summary
- 8% Below List Price
- $221/SF
- 6 Days On Market
- Last Sold Price $395,000
- May 23, 2024
Last Listing Agent Erica Smentowski KELLER WILLIAMS ON THE WATER S

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$649,000
- 4 Beds
- 4 Baths
- 2,847 Sq Ft
6840 Helmsley Cir, Windermere, FL 34786

Stunning Preston Square Windermere home — 4 beds, 4 baths and approximately 3,400 sq. ft. of heated living space in a functional two-story floor plan featuring multiple living areas, an open kitchen with an eat-in nook and architectural detailing, tray ceilings, custom built-ins, spacious walk-in closets and a versatile bonus room (ceiling fans throughout) that adapts to your lifestyle. Entertain

Eleanor DeSimone IAD FLORIDA LLC

6840 Helmsley Cir, Windermere, FL 34786
/2
$565,000 Sold Sep 29, 2025

6545 Chagford Ln, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,265 Sq Ft
- Built 2007
Last Sold Summary
- $249/SF
Current Estimated Value $554,835

Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

6545 Chagford Ln, Windermere, FL 34786

/45
Est $1,674,211 Not Listed For Sale

9012 Pinnacle Cir, Windermere, FL 34786
- 4 Beds
- 4.5 Baths
- 3,585 Sq Ft
- Built 2019
9012 Pinnacle Cir, Windermere, FL 34786

Last Sold Summary
- 12% Below List Price
- $529/SF
- 163 Days On Market
- Last Sold Price $1,895,000
- Jan 31, 2024
Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

/51
$1,119,990 Pending
- 6 Beds
- 4.5 Baths
- 3,542 Sq Ft
14354 Crest Palm Ave, Windermere, FL 34786

One or more photo(s) has been virtually staged. *Images shown are for illustrative purposes only* TIDEWATER W/BONUS - Our beautiful huge 2 story home, located on a beautiful conservation lot, with 6 Bedrooms and 4.5Baths. 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

Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

14354 Crest Palm Ave, Windermere, FL 34786
/2
$805,000 Sold Feb 13, 2026

14551 Yellow Butterfly Rd, Windermere, FL 34786
- 5 Beds
- 3.5 Baths
- 3,546 Sq Ft
- Built 2014
Last Sold Summary
- 2% Below List Price
- $227/SF
- 51 Days On Market
Current Estimated Value $795,634

Last Listing Agent Silvia Odebrecht ICON REALTY ASSOCIATES INC

14551 Yellow Butterfly Rd, Windermere, FL 34786

/17
Est $684,143 Not Listed For Sale

8712 Crescendo Ave, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 2,926 Sq Ft
- Built 2016
8712 Crescendo Ave, Windermere, FL 34786

Last Sold Summary
- 3% Above List Price
- $228/SF
- 119 Days On Market
- Last Sold Price $666,000
- Jul 15, 2024
Last Listing Agent Eileen Li TOPSKY REALTY INC

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$560,000
- 4 Beds
- 2.5 Baths
- 1,840 Sq Ft
8225 Bryce Canyon Ave, Windermere, FL 34786

Beautiful 4-Bedroom Home in Windermere, FL – Prime Location and Comfort for the Whole Family! Discover this amazing homelocated in one of Florida’s most desirable neighborhoods – Windermere! Featuring 4 spacious bedrooms, 2 full bathrooms and a half bath, this property offers the ideal space and layout for families seeking comfort and quality of life. The home is vacant and move-in ready,

Fernando Zucato CHARLES RUTENBERG REALTY ORLANDO

8225 Bryce Canyon Ave, Windermere, FL 34786
/2
$1,535,000 Sold Sep 19, 2025

11755 Waterstone Loop Dr, Windermere, FL 34786
- 5 Beds
- 5 Baths
- 3,665 Sq Ft
- Built 2012
Last Sold Summary
- 4% Below List Price
- $419/SF
- 97 Days On Market
Current Estimated Value $1,517,715

Last Listing Agent Deb Schroeder INFINITY REALTY GROUP LLC

11755 Waterstone Loop Dr, Windermere, FL 34786

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Est $741,583 Not Listed For Sale

13207 Orange Isle Dr, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,136 Sq Ft
- Built 2021
13207 Orange Isle Dr, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $244/SF
- 3 Days On Market
- Last Sold Price $765,000
- Sep 15, 2023
Last Listing Agent Shelley Dawson COMPASS FLORIDA LLC

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$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

Michelle Corbin ISLEWORTH REALTY LLC

9648 Mccormick Place, Windermere, FL 34786
/2
$1,800,000 Sold Jan 15, 2026

5412 Water Creek Dr, Windermere, FL 34786
- 4 Beds
- 4.5 Baths
- 4,247 Sq Ft
- Built 2005
Last Sold Summary
- 10% Below List Price
- $424/SF
- 39 Days On Market
Current Estimated Value $1,811,242

Last Listing Agent Kari Fleck THE REAL ESTATE COLLECTION LLC

5412 Water Creek Dr, Windermere, FL 34786

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Est $715,642 Not Listed For Sale

13608 Gorgona Isle Dr, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,834 Sq Ft
- Built 2020
13608 Gorgona Isle Dr, Windermere, FL 34786

Last Sold Summary
- 1% Below List Price
- $256/SF
- 28 Days On Market
- Last Sold Price $725,000
- Sep 15, 2023
Last Listing Agent Amy Kidwell PA PREFERRED REAL ESTATE BROKERS

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$825,000 Pending
- 4 Beds
- 3 Baths
- 2,903 Sq Ft
1412 Glenheather Dr, Windermere, FL 34786

Gorgeous UPDATED & UPGRADED Executive * POOL * home Located in the highly desired ~ GUARD GATED ~ Reserve at Belmere with fantastic LAKEFRONT Amenities including a Pier, Fitness Center, Beach Volleyball, Tennis, Playground & More! This Outstanding 4 Bedroom PLUS an OFFICE home will impress you at every turn. Situated on an Oversized 1/3 ACRE LOT with a HUGE Back Yard. Spacious and Open, Split

Kim Arena COLDWELL BANKER REALTY

1412 Glenheather Dr, Windermere, FL 34786
/2
$1,535,000 Sold Apr 15, 2026

1134 Kelso Blvd, Windermere, FL 34786
- 2 Beds
- 2 Baths
- 2,044 Sq Ft
- Built 2016
Last Sold Summary
- 3% Below List Price
- $751/SF
- 19 Days On Market
Current Estimated Value $1,637,029

Last Listing Agent Jennifer Tyre REALTY AND COMPANY INT., LLC

1134 Kelso Blvd, Windermere, FL 34786

/23
Est $717,987 Not Listed For Sale

9216 Outlook Rock Trail, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,985 Sq Ft
- Built 2016
9216 Outlook Rock Trail, Windermere, FL 34786

Last Sold Summary
- 6% Above List Price
- $226/SF
- 113 Days On Market
- Last Sold Price $675,000
- Dec 11, 2023
Last Listing Agent Olga Petrova CHOICE ONE REALTY LLC

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$469,000
- 4 Beds
- 3 Baths
- 1,980 Sq Ft
6552 Helmsley Cir, Windermere, FL 34786

Welcome home to Preston Square in beautiful Windermere! This stunning corner-unit townhome with 4 bedroom, 3 bathrooms offers the perfect blend of comfort, style, and convenience, with a new roof and fresh exterior paint. Step onto the cozy front porch and into a bright, inviting two-story home filled with natural light. The main living areas feature tile flooring throughout; great room showcases

Morgan Horsley THE REAL ESTATE COLLECTION LLC

6552 Helmsley Cir, Windermere, FL 34786
/55
$980,000 Sold Apr 01, 2026

14285 Crest Palm Ave, Windermere, FL 34786
- 4 Beds
- 4 Baths
- 3,123 Sq Ft
- Built 2026
Move in Ready Sold Summary
- $314/SF
- 6 Days On Market
Current Estimated Value $1,025,333

Dream Finders Homes Palms at Windermere

14285 Crest Palm Ave, Windermere, FL 34786

/60
Est $670,681 Not Listed For Sale

7949 Jailene Dr, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,015 Sq Ft
- Built 2012
7949 Jailene Dr, Windermere, FL 34786

Last Sold Summary
- $222/SF
- 122 Days On Market
- Last Sold Price $670,000
- Dec 11, 2023
Last Listing Agent Chris Bunnell EXP REALTY LLC

/25
$539,000
- 3 Beds
- 2 Baths
- 2,151 Sq Ft
6673 Duncaster St, Windermere, FL 34786

One or more photo(s) has been virtually staged. Located in the highly sought-after Windermere area, this 3-bedroom, 2-bath residence offers 2,151 heated square feet of functional and versatile living space. The layout includes a formal living room, a spacious great room, and a dedicated den/study, providing flexibility for work, entertaining, or additional living areas. A covered lanai extends

Lilyan Machuca MY REALTY GROUP, LLC.

6673 Duncaster St, Windermere, FL 34786
/2
$1,755,000 Sold Aug 15, 2025

11856 Vinci Dr, Windermere, FL 34786
- 5 Beds
- 4.5 Baths
- 3,680 Sq Ft
- Built 2011
Last Sold Summary
- 5% Below List Price
- $477/SF
- 108 Days On Market
Current Estimated Value $1,727,993

Last Listing Agent Oscar Rodriguez B LIVE COMMERCIAL AND RESIDENT

11856 Vinci Dr, Windermere, FL 34786

/28
Est $3,424,670 Not Listed For Sale

9950 6th St, Windermere, FL 34786
- 4 Beds
- 7 Baths
- 5,561 Sq Ft
- Built 2024
9950 6th St, Windermere, FL 34786

Last Sold Summary
- 2% Below List Price
- $629/SF
- 55 Days On Market
- Last Sold Price $3,500,000
- Jun 27, 2024
Last Listing Agent David Dorman CENTURY 21 CARIOTI

/62
$760,000
- 6 Beds
- 5.5 Baths
- 3,336 Sq Ft
11410 Rapallo Ln, Windermere, FL 34786

This stunning 6-bedroom Park Square home in Windermere combines elegance and functionality. The first floor features formal living and dining areas, a gourmet kitchen with stainless steel appliances and a gas stove, and a custom-designed patio garden with a water fountain and remote-controlled fans. Upstairs, enjoy luxury vinyl flooring, an oversized master suite with a walk-in closet, and

Rebeca Lima ORLANDO BROTHERS REAL ESTATE LLC

11410 Rapallo Ln, Windermere, FL 34786
/2
$1,400,000 Sold May 07, 2026

17521 Black Rail St, Windermere, FL 34786
- 6 Beds
- 4.5 Baths
- 5,316 Sq Ft
- Built 2015
Last Sold Summary
- 11% Below List Price
- $263/SF
- 96 Days On Market
Current Estimated Value $1,467,458

Last Listing Agent Rebecca Puig CHARLES RUTENBERG REALTY ORLANDO

17521 Black Rail St, Windermere, FL 34786

/41
Est $441,516 Not Listed For Sale

13760 Calera Aly, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,912 Sq Ft
- Built 2017
13760 Calera Aly, Windermere, FL 34786

Last Sold Summary
- 1% Below List Price
- $233/SF
- 15 Days On Market
- Last Sold Price $446,000
- Aug 28, 2023
Last Listing Agent Saida Ali COLDWELL BANKER REALTY

/68
$1,369,000 Pending
- 4 Beds
- 3.5 Baths
- 3,809 Sq Ft
8375 Bowden Way, Windermere, FL 34786

The kitchen has been recently upgraded with brand-new white quartz (Calacatta Belardo) countertops and backsplash, creating a bright, modern, and spacious feel. This charming four-bedroom, three-and-a-half-bath home in the highly sought-after Keene’s Pointe community perfectly combines elegance, comfort, and character. Designed with a timeless French-inspired décor, every space feels warm,

Oscar Rodriguez B LIVE COMMERCIAL AND RESIDENT

8375 Bowden Way, Windermere, FL 34786
/2
$1,045,000 Sold Jan 20, 2026

8764 Lookout Pointe Dr, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,423 Sq Ft
- Built 2015
Last Sold Summary
- 4% Below List Price
- $305/SF
- 71 Days On Market
Current Estimated Value $1,026,435

Last Listing Agent Ken Pozek REAL BROKER, LLC

8764 Lookout Pointe Dr, Windermere, FL 34786

/33
Est $1,356,414 Not Listed For Sale

1109 Estancia Woods Loop, Windermere, FL 34786
- 4 Beds
- 4 Baths
- 3,493 Sq Ft
- Built 2020
1109 Estancia Woods Loop, Windermere, FL 34786

Last Sold Summary
- 11% Above List Price
- $351/SF
- 39 Days On Market
- Last Sold Price $1,225,000
- Sep 08, 2023
Last Listing Agent Ginny Bissonnette IVRE ORLANDO

/92
$7,400,000 Pending
- 7 Beds
- 7.5 Baths
- 10,485 Sq Ft
6507 Rosella Ct, Windermere, FL 34786

Under contract-accepting backup offers. Luxury Living at its finest in one of Windermere's most unique Waterfront properties, with 2+ acres in the exclusive Keene's Pointe community. Soak up the Florida sunshine in the very private garden oasis boasting 2 Resort Style pools with waterfalls, grotto and waterslide, outdoor kitchen and fireplace all overlooking Lake Tibet on the Butler Chain of

DeAnna Sechrest DEANNA MARIE SECHREST

6507 Rosella Ct, Windermere, FL 34786
/2
$670,000 Sold Sep 09, 2025

9473 Palm Tree Dr, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 2,084 Sq Ft
- Built 1986
Last Sold Summary
- 3% Below List Price
- $321/SF
- 7 Days On Market
Current Estimated Value $652,976

Last Listing Agent Mike Long COLDWELL BANKER REALTY

9473 Palm Tree Dr, Windermere, FL 34786

/71
Est $597,516 Not Listed For Sale

6769 Merrick Landing Blvd, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,374 Sq Ft
- Built 2014
6769 Merrick Landing Blvd, Windermere, FL 34786

Last Sold Summary
- 4% Below List Price
- $263/SF
- 4 Days On Market
- Last Sold Price $625,000
- Jul 28, 2023
Last Listing Agent John Silva JOHN SILVA REALTY & ASSOCIATES

/62
$1,196,000
- 5 Beds
- 4.5 Baths
- 3,449 Sq Ft
11333 Camden Park Dr Unit 7, Windermere, FL 34786

One or more photo(s) has been virtually staged. "PRICE REDUCTION" - Nestled within highly sought after guard gated community, this exceptionally maintained two-story residence combines timeless elegance offering the ideal blend of style, comfort, and functionality. The home features 5 spacious bedrooms, 4.5 bathrooms, dinning room, separate living room from family room and a generously sized

Cynthia Noto KARDOSH REALTY

11333 Camden Park Dr Unit 7, Windermere, FL 34786

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