Windermere, FL Homes

/87
$2,300,000
- 5 Beds
- 4.5 Baths
- 4,284 Sq Ft
81 Oakdale St, Windermere, FL 34786

Gorgeous canal-front home with direct access to the Butler Chain of Lakes and just four blocks from the heart of downtown Windermere, this 2024 luxury remodel offers the perfect blend of modern living and small-town charm. Minutes from Food Truck Fridays, local cafés, parks, tennis courts, and year-round community events, this home blends modern elegance with the warmth of small-town living. Step

David Warzycha COLDWELL BANKER REALTY

81 Oakdale St, Windermere, FL 34786
/18
$4,500 Per Month
- 5 Beds
- 4 Baths
- 4,000 Sq Ft
- House for Rent
1351 Glenwick Dr, Windermere, FL 34786

POOL HOME!!! WITH MOTHER IN LAW SUIT!!! 5 BEDROOMS 4 FULL BATHS!!! MAN-GATED COMMUNITY IN WINDERMERE!!! Stunning Windermere home at 1351 Glenwick Dr! Spacious open floor plan, modern kitchen, and elegant finishes throughout. Perfect for entertaining or relaxing in the private backyard. Close to top schools, shopping, and dining. A must-see blend of luxury, comfort, and location!

Adriana Montes MBA FLORIDA DREAMS REALTY GRP INC

1351 Glenwick Dr, Windermere, FL 34786
/2
$585,000 Sold Aug 19, 2025

8359 Lookout Pointe Dr, Windermere, FL 34786
- 4 Beds
- 4 Baths
- 2,604 Sq Ft
- Built 2016
Last Sold Summary
- 1% Below List Price
- $225/SF
- 3 Days On Market
Current Estimated Value $583,372

Last Listing Agent Pilar Fernandez SIX STAR REALTY GROUP LLC

8359 Lookout Pointe Dr, Windermere, FL 34786

/51
Est $841,654 Not Listed For Sale

4240 Blue Major Dr, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,345 Sq Ft
- Built 2015
4240 Blue Major Dr, Windermere, FL 34786

Last Sold Summary
- 9% Below List Price
- $277/SF
- 55 Days On Market
- Last Sold Price $928,000
- Apr 15, 2024
Last Listing Agent Adriana Muzzi WRA BUSINESS & REAL ESTATE

/63
$975,000
- 4 Beds
- 3 Baths
- 2,743 Sq Ft
2125 Kane Park Way, Windermere, FL 34786

A rare opportunity to own a .71-acre pool home in the Town of Windermere for under $1 million—beautifully updated and truly move-in ready. Welcome to this beautifully updated single-story pool home on an oversized cul-de-sac lot in Windermere’s Willows at Lake Rhea, zoned for A-rated schools and offering exceptional privacy between homes. Surrounded by mature landscaping, the property provides a

Deb Schroeder INFINITY REALTY GROUP LLC

2125 Kane Park Way, Windermere, FL 34786
/21
$4,950 Per Month
- 3 Beds
- 2 Baths
- 2,056 Sq Ft
- House for Rent
8447 Bowden Way, Windermere, FL 34786

Welcome to Keenes Point - Windermere, a stunning 3-bedroom, 2-bathroom home located in the desirable Windermere, FL. This property is nestled within a secure gated community, offering an added layer of peace and security. The home boasts a private pool, perfect for cooling off during those hot Florida summers. The private backyard provides ample space for outdoor activities or simply enjoying the

Julien Silva JOHN SILVA REALTY & ASSOCIATES

8447 Bowden Way, Windermere, FL 34786
/2
$760,000 Sold Apr 10, 2026

12676 Salomon Cove Dr, Windermere, FL 34786
- 6 Beds
- 4 Baths
- 3,667 Sq Ft
- Built 2018
Last Sold Summary
- 15% Below List Price
- $207/SF
- 120 Days On Market
Current Estimated Value $790,934

Last Listing Agent Anna Shi LPT REALTY, LLC

12676 Salomon Cove Dr, Windermere, FL 34786

/16
Est $317,394 Not Listed For Sale

11564 Mizzon Dr Unit 904, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 1,455 Sq Ft
- Built 2006
11564 Mizzon Dr Unit 904, Windermere, FL 34786

Last Sold Summary
- 16% Below List Price
- $260/SF
- 1 Day On Market
- Last Sold Price $379,000
- Jul 31, 2023
Last Listing Agent Gonzalo Senior IRM INVEST., REAL EST.& MGMT.

/33
$440,000
- 3 Beds
- 2.5 Baths
- 1,742 Sq Ft
7612 Fairgrove Ave, Windermere, FL 34786

Beautiful two-story townhome in the desirable Windermere Sound community! This stunning residence offers 3 bedrooms, 2.5 bathrooms, and a spacious 2-car garage, spanning 1,742 sq. ft. of elegant living space. The home features stainless steel appliances, granite countertops, and modern finishes throughout. Windermere Sound provides residents with resort-style amenities, including a swimming pool,

Maribel Minarro FLORIDA FANTASY REAL ESTATE INC

7612 Fairgrove Ave, Windermere, FL 34786
/31
$2,795 Per Month
- 3 Beds
- 2.5 Baths
- 1,593 Sq Ft
- Townhouse for Rent
7255 Shadeview Aly, Windermere, FL 34786

Available Now! 3 bed/2.5 bath townhome in Windermere. This three-bedroom, two-and-a-half-bath residence offers an open main floor layout with ample natural light and comfortable living spaces. The primary suite includes a private bathroom, and two additional bedrooms provide flexible space for bedrooms, office, or hobby use. Jack and Jill bathroom, Washer and dryer included. Lawncare is also

Dawn Slaughter TRUSTHOME PROPERTIES INC

7255 Shadeview Aly, Windermere, FL 34786
/2
$2,700,000 Sold Feb 09, 2026

9151 Tibet Pointe Cir, Windermere, FL 34786
- Land
- 2.21 Acres
- $1,221,719 per Acre
Last Sold Summary
- 16% Below List Price
- 341 Days On Market
Current Estimated Value $2,707,564

Last Listing Agent Janet Allen PREMIER SOTHEBYS INT'L REALTY

9151 Tibet Pointe Cir, Windermere, FL 34786

/46
Est $1,175,384 Not Listed For Sale

7219 Sangalla Dr, Windermere, FL 34786
- 4 Beds
- 4.5 Baths
- 3,818 Sq Ft
- Built 2012
7219 Sangalla Dr, Windermere, FL 34786

Last Sold Summary
- 3% Above List Price
- $300/SF
- 6 Days On Market
- Last Sold Price $1,145,000
- Jun 23, 2023
Last Listing Agent Alex Vastardis COLDWELL BANKER REALTY

/49
$1,200,000
- 4 Beds
- 4 Baths
- 2,787 Sq Ft
1361 Whitney Isles Dr, Windermere, FL 34786

Stunning residence with a private fenced backyard, located in the highly sought-after gated community of Belmere in Windermere, just minutes from the town center. Featuring 4 bedrooms, 4 bathrooms, and approximately 2,800 sq. ft. of air-conditioned living space, this home immediately captivates with its elegant Mediterranean architecture and lush tropical landscaping. Fully renovated this year,

Gabriel Mantovani ALVES AND HOWELL REALTY

1361 Whitney Isles Dr, Windermere, FL 34786
/25
$2,800 Per Month
- 3 Beds
- 2.5 Baths
- 1,545 Sq Ft
- Townhouse for Rent
7609 Sutherton Ln, Windermere, FL 34786

Fully Renovated Corner Unit Townhome for Rent in Wickham Park – Windermere Beautiful 3-bedroom, 2.5-bath corner unit townhome, offering extra privacy, more natural light, and an enhanced sense of space, located in the desirable Wickham Park community in Windermere. This home features granite countertops, solid wood cabinets, stainless steel appliances news and a spacious open-concept living and

Vivian Azuaje 1 ELEVEN REALTY

7609 Sutherton Ln, Windermere, FL 34786
/2
$2,171,470 Sold Apr 29, 2026

1020 Oakdale St, Windermere, FL 34786
- 5 Beds
- 4.5 Baths
- 3,994 Sq Ft
- Built 2025
Last Sold Summary
- 1% Below List Price
- $544/SF
- 107 Days On Market
Current Estimated Value $2,153,636

Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

1020 Oakdale St, Windermere, FL 34786

/2
Est $536,050 Not Listed For Sale

7736 Brofield Ave, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 1,709 Sq Ft
- Built 2012
7736 Brofield Ave, Windermere, FL 34786

Last Sold Summary
- 2% Below List Price
- $321/SF
- 2 Days On Market
- Last Sold Price $549,000
- Mar 20, 2025
Last Listing Agent Rustin Davis MARKET CONNECT REALTY LLC

/63
$1,520,000
- 4 Beds
- 4.5 Baths
- 3,288 Sq Ft
1703 Roberts Landing Rd, Windermere, FL 34786

This elegant and fully renovated lakefront home on Lake Olivia in Windermere offers the ultimate blend of luxury, comfort, and Florida lifestyle. Featuring three master suites plus a guest bedroom and bathroom, the spacious layout is designed for both entertaining and everyday living. Large windows fill the home with natural light and frame breathtaking views of the water, while recent

Wui Keong Goh INTERNATIONAL NETWORK REALTY

1703 Roberts Landing Rd, Windermere, FL 34786
/45
$2,250 Per Month
- 3 Beds
- 2 Baths
- 1,455 Sq Ft
- Condo for Rent
11434 Jasper Kay Terrace Unit 206, Windermere, FL 34786

Spacious 3-bedroom, 2-bath condominium located on the 2nd floor of a well-maintained community in highly desirable Windermere, FL. This 1,455 sq ft unit offers an open and functional floor plan featuring a large living/dining area, generous natural light, and a well-appointed kitchen with ample cabinetry and counter space. The primary suite includes a walk-in closet and a private bath. Secondary

Rizwan Rashid MNT INTERNATIONAL

11434 Jasper Kay Terrace Unit 206, Windermere, FL 34786
/2
$380,000 Sold Nov 13, 2025

5219 Keenes Pheasant Dr, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,461 Sq Ft
- Built 2004
Last Sold Summary
- 1% Below List Price
- $260/SF
- 6 Days On Market
Current Estimated Value $378,423

Last Listing Agent Roland Cotardo THE SIMON SIMAAN GROUP

5219 Keenes Pheasant Dr, Windermere, FL 34786

/43
Est $2,805,444 Not Listed For Sale

13100 Bellaria Cir, Windermere, FL 34786
- 6 Beds
- 6.5 Baths
- 6,011 Sq Ft
- Built 2012
13100 Bellaria Cir, Windermere, FL 34786

Last Sold Summary
- 2% Above List Price
- $457/SF
- 40 Days On Market
- Last Sold Price $2,750,000
- Jul 26, 2023
Last Listing Agent Leonardo Pereira KAZA REAL ESTATE LLC

/63
$1,875,000
- 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 dual-zoned AC system in August 2025 including Nest smart thermostat. Situated across from the community park and tennis on one of the best

Frank Ferrell FERRELL REALTY, INC.

13420 Bonica Way, Windermere, FL 34786
/16
$3,000 Per Month
- 4 Beds
- 3 Baths
- 1,928 Sq Ft
- House for Rent
1243 Dingens Ave, Windermere, FL 34786

WONDERFUL WELCOME HOME IN WINDERMERE. READY TO MOVE IN. TOP RATED SCHOOLS IN A FAMILY COMMUNITY, NEAR DISNEY, DINING AND ENTERTAINMENT, MAY BE RENTED FULL FURNISHED, FEELS LIKE COUNTRY LIVING, BUT CLOSE TO EVERYTHING,so bring your boat, camper, or build the Gotha Park is just a short walk away, offering tennis courts, a pavilion, and a tot lot for the little ones. LOCATION, LOCATION,

Peter Useche REALMULTIPROPERTY LLC

1243 Dingens Ave, Windermere, FL 34786
/2
$675,000 Sold Apr 15, 2026

6990 Smithshire Ln, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 2,986 Sq Ft
- Built 2007
Last Sold Summary
- $226/SF
- 10 Days On Market
Current Estimated Value $672,114

Last Listing Agent Beverly Brown RE/MAX PRIME PROPERTIES

6990 Smithshire Ln, Windermere, FL 34786

/2
Est $823,928 Not Listed For Sale

13303 Roskin Ln, Windermere, FL 34786
- 5 Beds
- 5.5 Baths
- 3,609 Sq Ft
- Built 2011
13303 Roskin Ln, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $236/SF
- 70 Days On Market
- Last Sold Price $850,000
- Jan 27, 2025
Last Listing Agent Margaret Gay THREE MOUNTAINS REALTY

/28
$2,500,000
- 4 Beds
- 4.5 Baths
- 4,961 Sq Ft
13377 Lake Butler Blvd, Winter Garden, FL 34787

Fantastic opportunity to purchase 12+ acres of private, quiet lake front property in Winter Garden/Windermere area on West Lake Butler Blvd. with 4+ acres high and dry and no HOA. Property currently boasts dock with electricity and boat lift on a skiable lake. There is an existing house that could be remodeled or torn down and start fresh. Home is 4961 square feet and built in 1990 with

Dawn Briggs BLUE MAGNOLIA REALTY LLC

13377 Lake Butler Blvd, Winter Garden, FL 34787
/32
$2,500 Per Month
- 3 Beds
- 2 Baths
- 1,442 Sq Ft
- Condo for Rent
11434 Jasper Kay Terrace Unit 1101, Windermere, FL 34786

Beautifully updated 3-bedroom, 2-bathroom ground-floor condo offering 1,442 sq.ft. of thoughtfully designed living space. This unit has been fully renovated and presents in clean, modern condition with brand new interior paint, new laminate flooring throughout, refreshed ceilings, updated lighting fixtures, new ceiling fans, upgraded appliances, new window blinds, and updated hardware. The result

Denis Bochkov PINK MIAMI REAL ESTATE

11434 Jasper Kay Terrace Unit 1101, Windermere, FL 34786
/2
$1,220,000 Sold Jan 23, 2026

2828 Ingeborg Ct, Windermere, FL 34786
- 5 Beds
- 4.5 Baths
- 3,190 Sq Ft
- Built 1990
Last Sold Summary
- 8% Below List Price
- $382/SF
- 40 Days On Market
Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

2828 Ingeborg Ct, Windermere, FL 34786

/2
Est $329,648 Not Listed For Sale

8259 Maritime Flag St Unit 6, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,460 Sq Ft
- Built 2011
8259 Maritime Flag St Unit 6, Windermere, FL 34786

Last Sold Summary
- 4% Below List Price
- $236/SF
- 94 Days On Market
- Last Sold Price $345,000
- Feb 04, 2025
Last Listing Agent Hortencia Aponte LPT REALTY, LLC

/71
$1,199,000
- 4 Beds
- 3 Baths
- 2,599 Sq Ft
8351 Bowden Way, Windermere, FL 34786

Nestled within the highly acclaimed guard-gated community of Keene’s Pointe, this completely remodeled Windermere home offers a 4-bedroom, 3-bathroom estate that showcases timeless architectural details, curated modern finishes, and a seamless indoor-outdoor luxury lifestyle. Step inside to discover a light-filled open layout with tall coffered ceilings, custom-laid wood tile flooring, formal

Sharon Brandt KELLER WILLIAMS REALTY AT THE LAKES

8351 Bowden Way, Windermere, FL 34786
/15
$2,425 Per Month
- 3 Beds
- 2.5 Baths
- 1,510 Sq Ft
- Townhouse for Rent
7668 Billingham St, Windermere, FL 34786

... Welcome to Windermere! ... Move in ready... Newly installed LVP flooring for the upstairs and freshly painted for the entire house.... No Carpet... This home offers beautiful park views and a short walk to community pool! Custom features include neutral colors throughout, quartz kitchen countertops, 36- inch maple kitchen cabinets, tile backsplash, kitchen island, walk in pantry, pendent

Jennie Ho MAY HO REALTY

7668 Billingham St, Windermere, FL 34786
/2
$384,900 Sold Apr 09, 2026

7711 Fairgrove Ave, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,680 Sq Ft
- Built 2009
Last Sold Summary
- 3% Below List Price
- $229/SF
- 127 Days On Market
Current Estimated Value $380,762

Last Listing Agent Lindsay Kaye Voss VOSS REALTY INC

7711 Fairgrove Ave, Windermere, FL 34786

/37
Est $341,064 Not Listed For Sale

8259 Maritime Flag St Unit 1, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,601 Sq Ft
- Built 2011
8259 Maritime Flag St Unit 1, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $219/SF
- 85 Days On Market
- Last Sold Price $350,000
- Mar 27, 2024
Last Listing Agent Fernando Zucato CHARLES RUTENBERG REALTY ORLANDO

/28
$1,350,000 Pending
- 4 Beds
- 4.5 Baths
- 3,831 Sq Ft
3138 Seigneury Dr, Windermere, FL 34786

Under contract-accepting backup offers. Timeless style and classic design unfold behind the gates of Harbor Isle, one of Windermere’s most sought-after communities. This custom-built estate residence offers captivating views of Lake Down on the pristine Butler Chain of Lakes. Featuring all living areas on the first floor except for a bonus room upstairs, this thoughtfully crafted home offers

Rob Rahter STOCKWORTH REALTY GROUP

3138 Seigneury Dr, Windermere, FL 34786
/2
$2,400 Per Month
- 3 Beds
- 2.5 Baths
- 1,480 Sq Ft
- Townhouse for Rent
12876 Calderdale Ave, Windermere, FL 34786

Beautiful townhome in desirable Wickham Park. Premium lot with pool view. Townhome features anon floor plan with espresso kitchen cabinets, upgraded backsplash, granite countertops and stainless steel appliances. Private courtyard perfect for grilling and entertaining provides access to two car garage. Upstairs is the Master suite featuring a large window, walk in closet and a master bath with

Victor Jordan DEMAYA REALTY

12876 Calderdale Ave, Windermere, FL 34786
/2
$1,310,000 Sold May 01, 2026

8447 Woburn Ct, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,945 Sq Ft
- Built 1999
Last Sold Summary
- 1% Below List Price
- $445/SF
- 4 Days On Market
Current Estimated Value $1,177,242

Last Listing Agent Amy Seelman FLORIDA REALTY INVESTMENTS

8447 Woburn Ct, Windermere, FL 34786

/2
Est $1,257,321 Not Listed For Sale

6228 Roseate Spoonbill Dr, Windermere, FL 34786
- 8 Beds
- 5 Baths
- 4,751 Sq Ft
- Built 2012
6228 Roseate Spoonbill Dr, Windermere, FL 34786

Last Sold Summary
- 5% Above List Price
- $253/SF
- 201 Days On Market
- Last Sold Price $1,200,000
- Oct 02, 2024
Last Listing Agent Camila Castrillon COLDWELL BANKER REALTY

/43
$1,400,000
- 5 Beds
- 4 Baths
- 3,164 Sq Ft
11537 Claymont Cir, Windermere, FL 34786

Stunning transitional home in sought after manned gated Keene’s Pointe Community of Windermere! This beautifully renovated home offers a modern, neutral palette with high-end finishes throughout. Step inside to a grand foyer leading to the formal dining room, where coffered ceilings and tall windows flood the space with natural light. The open-concept kitchen and living area is a chef’s dream,

Julie Bettosini STOCKWORTH REALTY GROUP

11537 Claymont Cir, Windermere, FL 34786
/15
$3,600 Per Month
- 3 Beds
- 2 Baths
- 2,189 Sq Ft
- House for Rent
8117 Jailene Dr, Windermere, FL 34786

Experience refined living in this elegant 3-bed, 2-bath pool home nestled in the heart of Berkshire Park. Revel in the timeless allure of wood flooring gracing the main areas and master bedroom, while the two additional bedrooms offer plush comfort with carpeted floors. The expansive kitchen and thoughtfully designed layout enhance the home's appeal. Convenient inclusions, such as a washer and

Hans Welbergen WINDERMERE INTERNATIONAL REALTY

8117 Jailene Dr, Windermere, FL 34786
/2
$585,000 Sold Apr 30, 2026

6626 Bridgewater Village Rd, Windermere, FL 34786
- 3 Beds
- 3.5 Baths
- 2,720 Sq Ft
- Built 2014
Last Sold Summary
- 5% Below List Price
- $215/SF
- 150 Days On Market
Current Estimated Value $592,738

Last Listing Agent David Dorman CENTURY 21 CARIOTI

6626 Bridgewater Village Rd, Windermere, FL 34786

/2
Est $291,234 Not Listed For Sale

11446 Jasper Kay Terrace Unit 1012, Windermere, FL 34786
- 2 Beds
- 2 Baths
- 1,161 Sq Ft
- Built 2007
11446 Jasper Kay Terrace Unit 1012, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $258/SF
- 130 Days On Market
- Last Sold Price $300,000
- Jan 23, 2025
Last Listing Agent Mark Bridges CHARLES RUTENBERG REALTY ORLANDO

Showing Results 201 - 240, Page 6 of 18

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