Windermere, FL Homes

/2
Est $416,917 Not Listed For Sale

11740 Water Run Aly, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,569 Sq Ft
- Built 2016
11740 Water Run Aly, Windermere, FL 34786

Last Sold Summary
- 1% Below List Price
- $269/SF
- 26 Days On Market
Last Sold Price $422,000

Last Listing Agent Bryan Burns RE/MAX

/44
$384,900 Pending
- 3 Beds
- 2.5 Baths
- 1,680 Sq Ft
7711 Fairgrove Ave, Windermere, FL 34786

Under contract-accepting backup offers. Walk On In and Call It Home! Welcome to this move in ready gem of a townhome in the sought-after Lake Sawyer South community in Windermere! This spacious home offers: 3 Bedrooms | 2.5 Bathrooms Over 1,600 Sq. Ft. of Living Space and a 2-Car Garage—big enough to store your boat! Fresh interior paint, Beautiful tile and wood flooring throughout. Located in

Lindsay Kaye Voss VOSS REALTY INC

7711 Fairgrove Ave, Windermere, FL 34786
/2
$1,270,000 Sold Apr 10, 2025

6228 Lecco Way, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,755 Sq Ft
- Built 2012
Last Sold Summary
- 5% Below List Price
- $461/SF
- 41 Days On Market
Current Estimated Value $1,279,964

Last Listing Agent Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

6228 Lecco Way, Windermere, FL 34786

/2
Est $636,288 Not Listed For Sale

13125 Filly Ct, Lake Butler, FL 34786
13125 Filly Ct, Lake Butler, FL 34786

Last Sold Summary
- 22% Above List Price
- 9 Days On Market
Last Sold Price $520,000

Last Listing Agent Gretchen Sullivan RE/MAX

/30
$560,000 Pending
- 4 Beds
- 2.5 Baths
- 2,460 Sq Ft
7011 Nobleton Dr, Windermere, FL 34786

Under contract-accepting backup offers. Don't miss an Opportunity to own this Great Craftsman Home overlooking a serene Wooded View, located in the community of Lakes of Windermere. Impeccably maintained and Move-in ready, this 4-bedroom, 2.5-bath home offers numerous Upgrades and Touches throughout. Such as all new kitchen appliances, newly painted interior, new A/C, Hardwood flooring, Water

Sean Flatley KELLER WILLIAMS REALTY AT THE PARKS

7011 Nobleton Dr, Windermere, FL 34786
/2
$923,000 Sold Apr 08, 2025

5516 Remsen Cay Ln, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,070 Sq Ft
- Built 2006
Last Sold Summary
- 3% Below List Price
- $301/SF
- 92 Days On Market
Current Estimated Value $927,666

Last Listing Agent Angela Magac THE PROPERTY STOP LLC

5516 Remsen Cay Ln, Windermere, FL 34786

/2
Est $308,744 Not Listed For Sale

11565 Mizzon Dr Unit 804, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 1,455 Sq Ft
- Built 2006
11565 Mizzon Dr Unit 804, Windermere, FL 34786

Last Sold Summary
- 3% Above List Price
- $206/SF
- 64 Days On Market
Last Sold Price $300,000

Last Listing Agent Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

/46
$899,900
- 4 Beds
- 3.5 Baths
- 3,424 Sq Ft
13302 Roskin Ln, Windermere, FL 34786

Welcome to this impeccably maintained former model home in Windermere, beautifully positioned on a premium corner lot in a quiet, highly desirable community and zoned for top-rated schools. Offering over 3,400 square feet with 4 bedrooms and 3.5 bathrooms, this home stands out for its smart use of space, generous room sizes, and the refined “model home” presentation that feels clean, polished,

Xiaoyu Su RATIO REAL ESTATE, LLC

13302 Roskin Ln, Windermere, FL 34786
/2
$370,000 Sold Nov 06, 2025

13550 Carroway St, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 1,471 Sq Ft
- Built 2003
Last Sold Summary
- 3% Below List Price
- $252/SF
- 26 Days On Market
Current Estimated Value $369,941

Last Listing Agent Ricardo Diaz WEST ORLANDO PROPERTY MANAGEMENT REALTY, LLC

13550 Carroway St, Windermere, FL 34786

/2
Est $314,388 Not Listed For Sale

14276 Desert Haven St Unit GE, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,512 Sq Ft
- Built 2012
14276 Desert Haven St Unit GE, Windermere, FL 34786

Last Sold Summary
- 2% Below List Price
- $212/SF
- 66 Days On Market
Last Sold Price $320,000

Last Listing Agent Steve Montgomery EXP REALTY LLC

/97
$3,299,000
- 6 Beds
- 8 Baths
- 7,217 Sq Ft
4029 Isabella Cir, Windermere, FL 34786

Experience an architectural masterpiece in the gated enclave of Casabella. Situated on a rare, oversized .85-acre lot, this estate has been transformed by the original owner with impeccable attention to detail. The interior features 6 beds, 6 full and 2 half baths, all the high-scratch-resistant flooring throughout the home comes in a beautiful white oak finish with bathrooms featuring porcelain

Mauro Costa CORCORAN PREMIER REALTY

4029 Isabella Cir, Windermere, FL 34786
/2
$1,000,000 Sold May 29, 2025

9224 Legado Dr, Windermere, FL 34786
- 5 Beds
- 3 Baths
- 3,407 Sq Ft
- Built 2021
Last Sold Summary
- 17% Below List Price
- $294/SF
- 30 Days On Market
Current Estimated Value $1,008,503

Last Listing Agent Iluska Kruse ORLANDO BROTHERS REAL ESTATE LLC

9224 Legado Dr, Windermere, FL 34786

/2
Est $595,514 Not Listed For Sale

8311 Lookout Pointe Dr, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 2,460 Sq Ft
- Built 2016
8311 Lookout Pointe Dr, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $251/SF
- 53 Days On Market
Last Sold Price $616,500

Last Listing Agent Flavio Melo BB GROUP REALTY CORP

/75
$9,999,000
- 6 Beds
- 8 Baths
- 6,783 Sq Ft
6149 Grosvenor Shore Dr, Windermere, FL 34786

Keene's Pointe - Stunning lakefront home on Lake Tibet of the famed Butler Chain of Lakes. No detail was spared in this completely renovated home boasting formal living and dining rooms, family and media room, 2 offices, 6 full/2 half baths and 6 bedrooms - one of which could serve as a in-law suite with separate entrance from the outside. From the moment you enter this impeccably designed home

Teresa Stewart SOUTHERN REALTY GROUP LLC

6149 Grosvenor Shore Dr, Windermere, FL 34786
/2
$2,250,000 Sold Mar 09, 2026

409 W 2nd Ave, Windermere, FL 34786
- 5 Beds
- 4.5 Baths
- 4,688 Sq Ft
- Built 1995
Last Sold Summary
- 15% Below List Price
- $480/SF
- 338 Days On Market
Current Estimated Value $2,230,446

Last Listing Agent Amanda Black PA UPSIDE REAL ESTATE INC

409 W 2nd Ave, Windermere, FL 34786

/2
Est $820,444 Not Listed For Sale

11737 Sprawling Oak Dr, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,092 Sq Ft
- Built 2017
11737 Sprawling Oak Dr, Windermere, FL 34786

Last Sold Summary
- 4% Below List Price
- $278/SF
- 7 Days On Market
Last Sold Price $859,000

Last Listing Agent Alessandro Minato PREMIER SOTHEBYS INT'L REALTY

/60
$2,995,000
- 4 Beds
- 5 Baths
- 4,693 Sq Ft
10870 Bayshore Dr, Windermere, FL 34786

Set against the shimmering waters of Little Lake Down, this extraordinary lakefronthome offers an elevated expression of luxury living. Thoughtfully designed to maximizesweeping water views, the residence delivers a refined yet inviting atmosphere ideal forboth intimate living and grand entertaining. As you step inside you are greetedby a spacious open floor plan, highlighted by a

Julie Christensen ONE LUXURY INTERNATIONAL LLC

10870 Bayshore Dr, Windermere, FL 34786
/2
$670,000 Sold Jun 03, 2025

12627 Salomon Cove Dr, Windermere, FL 34786
- 5 Beds
- 4 Baths
- 2,886 Sq Ft
- Built 2018
Last Sold Summary
- 4% Below List Price
- $232/SF
- 41 Days On Market
Current Estimated Value $670,414

Last Listing Agent Tennille Biggers KELLER WILLIAMS ELITE PARTNERS III REALTY

12627 Salomon Cove Dr, Windermere, FL 34786

/2
Est $735,674 Not Listed For Sale

13212 Orange Isle Dr, Windermere, FL 34786
- 5 Beds
- 2.5 Baths
- 3,152 Sq Ft
- Built 2022
13212 Orange Isle Dr, Windermere, FL 34786

Last Sold Summary
- 1% Above List Price
- $232/SF
- 129 Days On Market
Last Sold Price $730,000

Last Listing Agent Antonio Gagliardi SUN WAVE REAL ESTATE, LLC

/30
$6,530,000
- 6 Beds
- 5.5 Baths
- 6,706 Sq Ft
1002 Down Reserve Ct, Windermere, FL 34786

Luxury, architectural elegance, and an unparalleled lakefront lifestyle on the Butler Chain of Lakes in Windermere. Set on a sprawling lot of over one acre, this extraordinary waterfront estate offers direct access to the prestigious Butler Chain of Lakes — a rare interconnected system of 12 private lakes, providing one of the most exclusive boating lifestyles in Central Florida. From the moment

Jennifer Olmeda WRA BUSINESS & REAL ESTATE

1002 Down Reserve Ct, Windermere, FL 34786
/2
$934,500 Sold Jul 23, 2025

2046 Westover Reserve Blvd, Windermere, FL 34786
- 5 Beds
- 4 Baths
- 3,516 Sq Ft
- Built 2000
Last Sold Summary
- 6% Below List Price
- $266/SF
- 30 Days On Market
Current Estimated Value $983,014

Last Listing Agent Brooke Cangro RE/MAX 200 REALTY

2046 Westover Reserve Blvd, Windermere, FL 34786

/57
Est $1,072,243 Not Listed For Sale

9245 Outlook Rock Trail, Windermere, FL 34786
- 5 Beds
- 3.5 Baths
- 4,502 Sq Ft
- Built 2017
9245 Outlook Rock Trail, Windermere, FL 34786

Last Sold Summary
- 7% Below List Price
- $255/SF
- 5 Days On Market
Last Sold Price $1,150,000

Last Listing Agent Pilar Fernandez SIX STAR REALTY GROUP LLC

/41
$574,995
- 4 Beds
- 2 Baths
- 1,798 Sq Ft
9319 Woodbreeze Blvd, Windermere, FL 34786

WONDERFUL WINDERMERE 4 BED/ 2 BATH HOME LOCATED IN THE CHARMING COMMUNITY OF SILVER WOODS. The moment you drive up to this home you are greeted by low maintence landscaping, paver driveway and a unique courtyard entry which makes this home standout. The courtyard is a perfect space to spend the evenings or start your mornings. Sliders from the kitchen lead onto the courtyard. Upon entering you

Steven Looper CHARLES RUTENBERG REALTY ORLANDO

9319 Woodbreeze Blvd, Windermere, FL 34786
/2
$340,000 Sold Feb 06, 2026

12716 Langstaff Dr, Windermere, FL 34786
- 2 Beds
- 2.5 Baths
- 1,181 Sq Ft
- Built 2003
Last Sold Summary
- 9% Below List Price
- $288/SF
- 85 Days On Market
Current Estimated Value $334,420

Last Listing Agent Ann Wargo UPSIDE REAL ESTATE INC

12716 Langstaff Dr, Windermere, FL 34786

/2
Est $397,209 Not Listed For Sale

11722 Water Run Aly, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,584 Sq Ft
- Built 2017
11722 Water Run Aly, Windermere, FL 34786

Last Sold Summary
- 5% Below List Price
- $265/SF
- 32 Days On Market
Last Sold Price $420,000

Last Listing Agent Alvaro Molina TWIN HOMES REALTY

/95
$2,250,000
- 4 Beds
- 3.5 Baths
- 3,525 Sq Ft
505 Jennifer Ln, Windermere, FL 34786

Villa Casablanca | Luxury Windermere Estate on 1-Acre. Some homes are built. Villa Casablanca was transformed. Set on a rare private acre within one of Windermere’s most privately held enclaves— this white-painted brick estate makes an immediate architectural statement. A circular motor court, tiered fountain, and mature canopy trees establish presence before you ever step inside.What unfolds

Ahmad Hassan COMPASS FLORIDA LLC

505 Jennifer Ln, Windermere, FL 34786
/2
$498,000 Sold Aug 01, 2025

4813 River Gem Ave, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 2,085 Sq Ft
- Built 2006
Last Sold Summary
- 9% Below List Price
- $239/SF
- 55 Days On Market
Current Estimated Value $507,368

Last Listing Agent Suzanne Hosmer RE/MAX SELECT GROUP

4813 River Gem Ave, Windermere, FL 34786

/35
Est $403,697 Not Listed For Sale

11716 Water Run Aly, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,629 Sq Ft
- Built 2017
11716 Water Run Aly, Windermere, FL 34786

Last Sold Summary
- 4% Below List Price
- $258/SF
- 5 Days On Market
Last Sold Price $420,000

Last Listing Agent Romulo Aguiar CHARLES RUTENBERG REALTY ORLANDO

/29
$725,000
- 4 Beds
- 2 Baths
- 2,373 Sq Ft
17514 Black Rail St, Windermere, FL 34786

New painting interior and doors and baseboards. This elegant single-level detached home features soaring 10-foot ceilings throughout, creating a bright and spacious atmosphere rarely found in one-story living. The home is thoughtfully positioned with a tranquil pond at the rear, offering both beautiful water views and exceptional privacy. A classic tiled roof adds timeless character and

He Gao U S GLORY REALTY

17514 Black Rail St, Windermere, FL 34786
/2
$3,350,000 Sold Jul 15, 2025

5801 Marleon Dr, Windermere, FL 34786
- 6 Beds
- 6.5 Baths
- 6,968 Sq Ft
- Built 1997
Last Sold Summary
- 7% Below List Price
- $481/SF
- 5 Days On Market
Current Estimated Value $3,314,248

Last Listing Agent Michelle Brierley COLDWELL BANKER REALTY

5801 Marleon Dr, Windermere, FL 34786

/2
Est $509,980 Not Listed For Sale

6352 Golden Dewdrop Trail, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,984 Sq Ft
- Built 2012
6352 Golden Dewdrop Trail, Windermere, FL 34786

Last Sold Summary
- 3% Above List Price
- $249/SF
- 15 Days On Market
Last Sold Price $495,000

Last Listing Agent Jessica Souza Meuli WRA BUSINESS & REAL ESTATE

$587,990 New Construction
- 3 Beds
- 2.5 Baths
- 1,714 Sq Ft
Butler Plan at Lake Cawood Cove - Townhomes, Windermere, FL 34786

Ashton Woods Builder

5432 Winter Garden Vineland Rd Unit 37932782, Windermere, FL 34786
/2
$1,560,000 Sold Aug 11, 2025

8437 Lake Burden Cir, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,797 Sq Ft
- Built 2005
Last Sold Summary
- 16% Below List Price
- $411/SF
- 105 Days On Market
Current Estimated Value $1,547,844

Last Listing Agent Daniela de Rodriguez B LIVE COMMERCIAL AND RESIDENT

8437 Lake Burden Cir, Windermere, FL 34786

/33
Est $509,981 Not Listed For Sale

8553 Crescendo Ave, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,841 Sq Ft
- Built 2016
8553 Crescendo Ave, Windermere, FL 34786

Last Sold Summary
- $278/SF
- 26 Days On Market
Last Sold Price $512,000

Last Listing Agent Thad Czapka COLDWELL BANKER REALTY

/29
$649,000
- 5 Beds
- 3.5 Baths
- 2,960 Sq Ft
12936 Droxford Rd, Windermere, FL 34786

Seller offering up to $10,000 towards Buyer's closing cost with acceptable offerLakes of Windermere STUNNER! This Ashton Woods Kensington model comes with an amazing bonus room and much more! The well-established neighborhood is out of a Norman Rockwell painting, lined with trees, 15 minutes from Disney, and loaded with charm. All you will need are a couple of Adirondack chairs for the front

Leo Rico UNITED REAL ESTATE PREFERRED

12936 Droxford Rd, Windermere, FL 34786
/2
$740,000 Sold Jan 08, 2026

11849 Cave Run Ave, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,414 Sq Ft
- Built 2014
Last Sold Summary
- 11% Below List Price
- $217/SF
- 86 Days On Market
Current Estimated Value $737,571

Last Listing Agent Any Alves WRA BUSINESS & REAL ESTATE

11849 Cave Run Ave, Windermere, FL 34786

/2
Est $1,501,228 Not Listed For Sale

11769 Hampstead St, Windermere, FL 34786
- 5 Beds
- 4 Baths
- 4,979 Sq Ft
- Built 2016
11769 Hampstead St, Windermere, FL 34786

Last Sold Summary
- $301/SF
- 12 Days On Market
Last Sold Price $1,500,000

Last Listing Agent John Cunningham KELLER WILLIAMS CLASSIC

/81
$5,489,000
- 6 Beds
- 9 Baths
- 8,305 Sq Ft
9721 Carillon Park Dr, Windermere, FL 34786

Welcome to 9721 Carillon Park Dr, Windermere, FL 34786 - a stunning FULLY FURNISHED (furniture included-with exception of a few items) , professionally designed estate inside the guard-gated community of Keene’s Pointe.This extraordinary residence offers 8,305 square feet of luxury living space with refined architectural details, elegant wood beams, and designer finishes throughout. MAIN

Dianna Desboyaux DOUGLAS ELLIMAN

9721 Carillon Park Dr, Windermere, FL 34786
/2
$405,000 Sold Apr 30, 2025

6367 Merrick Landing Blvd, Windermere, FL 34786
- 3 Beds
- 3 Baths
- 1,387 Sq Ft
- Built 2003
Last Sold Summary
- 1% Below List Price
- $292/SF
- 13 Days On Market
Current Estimated Value $395,060

Last Listing Agent Bobby Christiano COLDWELL BANKER REALTY

6367 Merrick Landing Blvd, Windermere, FL 34786

/2
Est $505,448 Not Listed For Sale

8308 Bryce Canyon Ave, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,065 Sq Ft
- Built 2016
8308 Bryce Canyon Ave, Windermere, FL 34786

Last Sold Summary
- 5% Below List Price
- $257/SF
- 4 Days On Market
Last Sold Price $530,000

Last Listing Agent Pilar Fernandez SIX STAR REALTY GROUP LLC

Showing Results 361 - 400, Page 10 of 18

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