Windermere, FL Homes

• 

  

  /2

  Est $458,386

  Not Listed For Sale

  10655 Village Lake Rd, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 1,938 Sq Ft
  • Built 2014

  10655 Village Lake Rd, Windermere, FL 34786

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Steven Horner RE/MAX PRIME PROPERTIES
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  /16

  $549,900

  • Land
  • 2.62 Acres
  • $209,885 per Acre

  1661 Roberts Landing Rd, Windermere, FL 34786

  Location, Location, Location!! Windermere Lot: 2.62 acres, with 1 acre buildable, for an incredible luxury designer estate with partial water views of Lake Olivia and a stream. NO HOA REQUIRED! Bring your custom builder. When you see this land, you will admire the beauty of nature. Gorgeous conservation views and spacious areas between the homes in the community. Nestled in the heart of Central

  Lana Watts CHARLES RUTENBERG REALTY ORLANDO

  1661 Roberts Landing Rd, Windermere, FL 34786
• 

  

  /2

  $455,000

  Sold Jun 29, 2026

  13733 Bressler Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,002 Sq Ft
  • Built 2019

  Last Sold Summary

  • 3% Below List Price
  • $227/SF
  • 93 Days On Market

  Current Estimated Value $455,068

  Last Listing Agent Robert Welker, III CORCORAN PREMIER REALTY

  13733 Bressler Aly, Windermere, FL 34786
• 

  

  

  /42

  Est $862,931

  Not Listed For Sale

  11859 Gold Creek Trail, Windermere, FL 34786

  • 6 Beds
  • 4 Baths
  • 3,804 Sq Ft
  • Built 2012

  11859 Gold Creek Trail, Windermere, FL 34786

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Flavio Melo BB GROUP REALTY CORP
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  /2

  $1,379,990

  New Construction

  • 6 Beds
  • 4.5 Baths
  • 4,443 Sq Ft

  14359 Crest Palm Ave, Windermere, FL 34786

  14359 Crest Palm Avenue The Sweetwater floorplan offers expansive living with its thoughtfully designed two-story layout. This home features six spacious bedrooms and four and a half bathrooms, perfectly accommodating larger households or guests. With over 4,400 square feet of living space, the Sweetwater includes both a flex room and multiple bonus spaces, offering flexibility for hobbies,

  Dream Finders Homes Builder

  14359 Crest Palm Ave, Windermere, FL 34786
• 

  /2

  $365,000

  Sold Jul 03, 2026

  12210 Langstaff Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,480 Sq Ft
  • Built 2012

  Last Sold Summary

  • 3% Below List Price
  • $247/SF
  • 51 Days On Market

  Current Estimated Value $368,294

  Last Listing Agent Ernesto Cisneros ELITE REALTY ENTERPRISES LLC

  12210 Langstaff Dr, Windermere, FL 34786
• 

  /2

  Est $410,189

  Not Listed For Sale

  8673 Coventry Park Way, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,760 Sq Ft
  • Built 2016

  8673 Coventry Park Way, Windermere, FL 34786

  Last Sold Summary

  • 101 Days On Market

  Last Listing Agent Yogini Bhave CHARLES RUTENBERG REALTY ORLANDO
• 

  

  /34

  $975,000

  Pending

  • 3 Beds
  • 3 Baths
  • 2,700 Sq Ft

  9600 Ambleside Dr, Windermere, FL 34786

  Welcome to this beautifully updated home situated on a full 1-acre homesite in a highly desirable, established community surrounded by mature trees. Enjoy access to the Butler Chain of Lakes for just $100 annually, offering an incredible opportunity for boating, fishing, and the Florida lake lifestyle. Inside, the home features a spacious open layout with an updated kitchen, white cabinetry,

  Paul West NATIONAL REAL ESTATE

  9600 Ambleside Dr, Windermere, FL 34786
• 

  /2

  $375,000

  Sold Apr 27, 2026

  12683 Langstaff Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,428 Sq Ft
  • Built 2003

  Last Sold Summary

  • $263/SF
  • 3 Days On Market

  Current Estimated Value $372,199

  Last Listing Agent Vlad Kizlo KELLER WILLIAMS REALTY AT THE LAKES

  12683 Langstaff Dr, Windermere, FL 34786
• 

  

  /18

  Est $1,104,712

  Not Listed For Sale

  14268 Crest Palm Ave, Windermere, FL 34786

  • 4 Beds
  • 4 Baths
  • 3,100 Sq Ft
  • Built 2025

  14268 Crest Palm Ave, Windermere, FL 34786

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Mark Raumaker SERHANT
• 

  

  /100

  $3,400,000

  • 6 Beds
  • 6.5 Baths
  • 5,666 Sq Ft

  9679 Westover Roberts Rd, Windermere, FL 34786

  Spectacular Private Gated Lakefront Estate on Lake Olivia in Windermere - From the moment you enter through the custom iron gates, you are welcomed into a private lakefront estate unlike any other. Nestled on 1.75 acres along the shores of Lake Olivia, this custom-built Mediterranean residence showcases Tuscan-inspired architecture, mature landscaping, and a winding paver drive creating a true

  Tony Davids TONYDAVIDSHOMES.COM, LLC

  9679 Westover Roberts Rd, Windermere, FL 34786
• 

  /2

  $580,000

  Sold Sep 22, 2025

  12867 Penshurst Ln, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 2,300 Sq Ft
  • Built 2004

  Last Sold Summary

  • 3% Below List Price
  • $252/SF
  • 3 Days On Market

  Current Estimated Value $583,148

  Last Listing Agent Stefany Marcelino RE/MAX INNOVATION

  12867 Penshurst Ln, Windermere, FL 34786
• 

  /2

  Est $3,361,918

  Not Listed For Sale

  5006 Sawyer Cove Way, Windermere, FL 34786

  • 4 Beds
  • 7 Baths
  • 5,727 Sq Ft
  • Built 2018

  5006 Sawyer Cove Way, Windermere, FL 34786

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Shawna Tree MEGAN DOWDY REALTY, LLC
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  /38

  $520,000

  $30K PRICE DROP Pending

  • 3 Beds
  • 2.5 Baths
  • 1,984 Sq Ft

  6412 Golden Dewdrop Trail, Windermere, FL 34786

  RARE OPPORTUNITY IN WINDERMERE LANDINGS! Beautifully upgraded 4-bedroom home in one of Windermere's most desirable communities, just steps from Windermere Preparatory School.Originally designed with an expansive downstairs living and family room layout, the spacious loft was thoughtfully converted into a versatile fourth bedroom, creating exceptional value rarely found at this price

  Jose Rojo URBAN-O REAL ESTATE SOLUTIONS

  6412 Golden Dewdrop Trail, Windermere, FL 34786
• 

  /2

  $395,000

  Sold Jul 13, 2026

  7249 Shadeview Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,569 Sq Ft
  • Built 2016

  Last Sold Summary

  • 8% Below List Price
  • $252/SF
  • 78 Days On Market

  Current Estimated Value $392,404

  Last Listing Agent Blanca Armada REMAX PREMIER PROPERTIES

  7249 Shadeview Aly, Windermere, FL 34786
• 

  /2

  Est $893,969

  Not Listed For Sale

  6607 Crestmont Glen Ln, Windermere, FL 34786

  • 5 Beds
  • 3.5 Baths
  • 3,199 Sq Ft
  • Built 2002

  6607 Crestmont Glen Ln, Windermere, FL 34786

  Last Sold Summary

  • 126 Days On Market

  Last Listing Agent Joey Feeser WEICHERT REALTORS HALLMARK PR
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  /67

  $2,650,000

  $350K PRICE DROP

  • 6 Beds
  • 7 Baths
  • 7,016 Sq Ft

  9656 Weatherstone Ct, Windermere, FL 34786

  Nestled within the exclusive gated enclave of Weatherstone on Lake Olivia, one of Windermere’s most private and sought-after lakefront communities, this extraordinary estate offers an exceptional combination of luxury, space, and waterfront living. Situated on approximately two acres of dry land with direct frontage on skiable Lake Olivia, this impressive 7,016-square-foot residence is designed

  Andy Neal THE AGENCY FL

  9656 Weatherstone Ct, Windermere, FL 34786
• 

  /2

  $675,000

  Sold Jul 10, 2026

  9376 Woodbreeze Blvd, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,026 Sq Ft
  • Built 1986

  Last Sold Summary

  • $333/SF
  • 11 Days On Market

  Current Estimated Value $668,441

  Last Listing Agent Kimberly Ann Zeidner, LLC CHARLES RUTENBERG REALTY ORLANDO

  9376 Woodbreeze Blvd, Windermere, FL 34786
• 

  

  /21

  Est $741,891

  Not Listed For Sale

  8736 Peachtree Park Ct, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,775 Sq Ft
  • Built 2017

  8736 Peachtree Park Ct, Windermere, FL 34786

  Last Sold Summary

  • 172 Days On Market

  Last Listing Agent Michael Velasquez THE SIMON SIMAAN GROUP
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  /60

  $360,000

  • 2 Beds
  • 2.5 Baths
  • 1,311 Sq Ft

  12417 Cruxbury Dr, Windermere, FL 34786

  Welcome to the peaceful townhome community of The Lakes of Windermere, conveniently nestled just behind Walt Disney World’s Magic Kingdom! Enjoy beautiful green space out front and a tranquil conservation area in the back. The affordable HOA provides added peace of mind by covering exterior and roof maintenance, landscaping, and access to the sparkling community pool. This 2-bedroom, 2.5-bath

  Christopher Govatos CHARLES RUTENBERG REALTY ORLANDO

  12417 Cruxbury Dr, Windermere, FL 34786
• 

  /2

  $549,900

  Sold Jul 17, 2026

  9072 Woodbreeze Blvd, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,721 Sq Ft
  • Built 1985

  Last Sold Summary

  • 4% Below List Price
  • $320/SF
  • 39 Days On Market

  Current Estimated Value $544,825

  Last Listing Agent Charles Kohlinger BHHS FLORIDA REALTY

  9072 Woodbreeze Blvd, Windermere, FL 34786
• 

  /2

  Est $517,243

  Not Listed For Sale

  6322 Golden Dewdrop Trail, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,136 Sq Ft
  • Built 2012

  6322 Golden Dewdrop Trail, Windermere, FL 34786

  Last Sold Summary

  • 64 Days On Market

  Last Listing Agent James Martinez CHARLES RUTENBERG REALTY ORLANDO
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  /48

  $860,000

  $10K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,078 Sq Ft

  2139 Tillman Ave, Winter Garden, FL 34787

  Tucked inside a sought-after gated community, this beautifully designed 4-bedroom, 4-bath home with office/den, offers the perfect blend of comfort, elegance, and everyday livability. From the moment you arrive, you’ll appreciate the sense of privacy, space, and thoughtful design that make this home truly special. With formal living and dining rooms, a private office/study, and a spacious bonus

  Marti Purdy MARTI PURDY PROPERTIES INC

  2139 Tillman Ave, Winter Garden, FL 34787
• 

  /2

  $1,050,000

  Sold May 21, 2026

  316 E 5th Ave, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,412 Sq Ft
  • Built 1962

  Last Sold Summary

  • 5% Below List Price
  • $435/SF
  • 22 Days On Market

  Current Estimated Value $1,040,267

  Last Listing Agent Darrell Nunnelley VINTAGE REALTY GROUP LLC

  316 E 5th Ave, Windermere, FL 34786
• 

  /2

  Est $1,193,457

  Not Listed For Sale

  6020 Golden Dewdrop Trail, Windermere, FL 34786

  • 8 Beds
  • 5 Baths
  • 4,740 Sq Ft
  • Built 2012

  6020 Golden Dewdrop Trail, Windermere, FL 34786

  Last Sold Summary

  • 30 Days On Market

  Last Listing Agent Rick Brown KELLER WILLIAMS ADVANTAGE 2 REALTY
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  /44

  $1,090,000

  $25K PRICE DROP Pending

  • 4 Beds
  • 4 Baths
  • 3,646 Sq Ft

  8344 Bowden Way, Windermere, FL 34786

  Virtually Staged. One or more photo(s) was virtually staged. *** BRAND NEW ROOF AUG 2026 *** This is your opportunity to own a home in Keene's Pointe, a 24-hour guard-gated golf community on the Butler Chain of Lakes and home to the Golden Bear Club. Built by David Weekley and proudly offered by its original owner, this 4-bedroom, 4-bathroom home offers 3,646 square feet of flexible living space,

  Immu Korvenmaa ALIGN REAL ESTATE LLC

  8344 Bowden Way, Windermere, FL 34786
• 

  /2

  $1,400,000

  Sold Apr 08, 2026

  6023 Blakeford Dr, Windermere, FL 34786

  • 5 Beds
  • 3 Baths
  • 3,013 Sq Ft
  • Built 1999

  Last Sold Summary

  • 8% Below List Price
  • $465/SF
  • 9 Days On Market

  Current Estimated Value $1,388,089

  Last Listing Agent Angela Durruthy KEENE'S POINTE REALTY

  6023 Blakeford Dr, Windermere, FL 34786
• 

  /2

  Est $568,431

  Not Listed For Sale

  8014 Jailene Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,322 Sq Ft
  • Built 2012

  8014 Jailene Dr, Windermere, FL 34786

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Tina St Clair ST. CLAIR REALTY GROUP, LLC
• 

  

  /55

  $990,000

  • 4 Beds
  • 3 Baths
  • 2,728 Sq Ft

  1243 Dingens Ave, Windermere, FL 34786

  Completely renovated Gotha/Windermere retreat with NO HOA—bring your boat, RV, or camper! This rare property features a light-filled 3BR/2BA main home with living, dining, and family rooms, PLUS a private detached 1BR/loft in-law suite complete with a kitchenette and living space. Ideal for multi-generational living or private guest quarters! Fully updated from top to bottom: new stucco-finished

  Peter Useche REALMULTIPROPERTY LLC

  1243 Dingens Ave, Windermere, FL 34786
• 

  /2

  $360,000

  Sold Jul 09, 2026

  14236 Oasis Cove Blvd, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,512 Sq Ft
  • Built 2011

  Last Sold Summary

  • 6% Below List Price
  • $238/SF
  • 66 Days On Market

  Current Estimated Value $363,650

  Last Listing Agent Raquel Saunders WRA BUSINESS & REAL ESTATE

  14236 Oasis Cove Blvd, Windermere, FL 34786
• 

  /2

  Not Listed For Sale

  8136 Serenity Spring Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,840 Sq Ft
  • Built 2013

  8136 Serenity Spring Dr, Windermere, FL 34786

  Last Sold Summary

  • 63 Days On Market

  Last Listing Agent Sophia Gordon, LLC COLDWELL BANKER REALTY
• 

  

  /40

  $549,000

  $21K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,411 Sq Ft

  4627 Blue Major Dr, Windermere, FL 34786

  Welcome to your new forever home in Summerport! This beautifully designed 4-bedroom, 3-bath home offers 2,411 square feet of spacious living with stunning golf course views and no rear neighbors, creating a sense of privacy that’s hard to find. A manicured front lawn welcomes you in, while inside, long hallways with tray ceilings and arched doorways set an elegant tone from the moment you enter.

  Daniel DeLuca DENIZ REALTY PARTNERS LLC

  4627 Blue Major Dr, Windermere, FL 34786
• 

  /2

  $890,000

  Sold Aug 11, 2026

  1002 Oakdale St, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 3,516 Sq Ft
  • Built 1973

  Last Sold Summary

  • 9% Below List Price
  • $253/SF
  • 97 Days On Market

  Current Estimated Value $970,503

  Last Listing Agent Frank Smith KELLER WILLIAMS SUBURBAN TAMPA

  1002 Oakdale St, Windermere, FL 34786
• 

  /2

  Est $380,323

  Not Listed For Sale

  11746 Water Run Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,588 Sq Ft
  • Built 2016

  11746 Water Run Aly, Windermere, FL 34786

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Kris Ibrahim HOME WISE REALTY GROUP, INC.
• 

  

  /59

  $354,900

  • 2 Beds
  • 2.5 Baths
  • 1,412 Sq Ft

  7430 Bentonshire Ave, Windermere, FL 34786

  Virtually Staged. SOME PHOTOS HAVE BEEN VIRTUALLY STAGED. MOVE-IN READY and listed below recent appraisal - ideally located in the highly desirable Wickham Park community of Windermere! This desirable END UNIT 2-bedroom, 2.5-bath townhome offers CAREFREE, LOW-MAINTENANCE LIVING with the added benefit of its end-unit location and an outstanding setting directly across the street from expansive

  Chris Bunnell EXP REALTY LLC

  7430 Bentonshire Ave, Windermere, FL 34786
• 

  /2

  $820,000

  Sold Mar 06, 2026

  416 Magnolia St, Windermere, FL 34786

  • 2 Beds
  • 1.5 Baths
  • 2,115 Sq Ft
  • Built 1915

  Last Sold Summary

  • 7% Below List Price
  • $388/SF
  • 74 Days On Market

  Current Estimated Value $849,431

  Last Listing Agent Judy Black UPSIDE REAL ESTATE INC

  416 Magnolia St, Windermere, FL 34786
• 

  /2

  Est $437,466

  Not Listed For Sale

  8972 Matriarca Aly, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,692 Sq Ft
  • Built 2020

  8972 Matriarca Aly, Windermere, FL 34786

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Ron Sprague LPT REALTY, LLC
• 

  

  /44

  $940,000

  $59K PRICE DROP

  • 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 furnished former model home with many extras and amenities 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

  Teresa Stewart SOUTHERN REALTY GROUP LLC

  8525 Bowden Way, Windermere, FL 34786
• 

  /2

  $685,000

  Sold May 20, 2026

  13243 Charfield St, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 2,794 Sq Ft
  • Built 2010

  Last Sold Summary

  • 2% Below List Price
  • $245/SF
  • 6 Days On Market

  Current Estimated Value $690,860

  Last Listing Agent Ken Pozek REAL BROKER, LLC

  13243 Charfield St, Windermere, FL 34786
• 

  

  /18

  Est $334,922

  Not Listed For Sale

  13179 Kegan St, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,617 Sq Ft
  • Built 2015

  13179 Kegan St, Windermere, FL 34786

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Miguel Lopez AGENT TRUST REALTY CORPORATION

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