Windermere, FL Homes

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  $530,000 Sold Aug 15, 2025

  12868 Holdenbury Ln, Windermere, FL 34786

  • 4 Beds
  • 2.5 Baths
  • 2,460 Sq Ft
  • Built 2006

  Last Sold Summary

  • 11% Below List Price
  • $215/SF
  • 39 Days On Market

  Current Estimated Value $535,017

  Last Listing Agent Victor Nawrocki VISION HOME REAL ESTATE, LLC

  12868 Holdenbury Ln, Windermere, FL 34786
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  /50

  Est $551,924 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,214 Sq Ft

  7861 Berkshire Oak Aly, Windermere, FL 34786

  7861 Berkshire Oak Aly, Windermere, FL 34786
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  $850,000

  • 4 Beds
  • 3 Baths
  • 2,764 Sq Ft

  11714 Delwick Dr, Windermere, FL 34786

  Just imagine yourself living in a pristine community with a long, impressive entrance that is guard gated like The Reserve at Belmere and Actually doing so! Now you have that opportunity in this fabulous Mediterranean – style home with almost 2800 Sq Feet of heated space. This home has it all. All that’s missing is you so call for your appointment today.This home offers the desirable private

  Veronica Davis-Lee RE/MAX 200 REALTY

  11714 Delwick Dr, Windermere, FL 34786
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  $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

  Last Listing Agent Stefany Marcelino DJ & LINDSEY REAL ESTATE

  12867 Penshurst Ln, Windermere, FL 34786
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  /25

  Est $382,465 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,505 Sq Ft

  12852 Calderdale Ave, Windermere, FL 34786

  12852 Calderdale Ave, Windermere, FL 34786
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  $13,650,000 New Construction

  • 9 Beds
  • 16 Baths
  • 20,445 Sq Ft

  9621 Windy Ridge Rd, Windermere, FL 34786

  Under Construction. Experience unmatched privacy, prestige, and personalization with this brand-new mansion on 2.5 pristine acres in the heart of Windermere. Tucked against protected government land that can never be developed, this estate offers the serenity of untouched nature with the ultimate in luxury living.Two Pools one outdoor with a swim up bar and grill area and the other indoor pool

  Natalie Citarelli CITARELLI REALTY GROUP LLC

  9621 Windy Ridge Rd, Windermere, FL 34786
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  $393,000 Sold Mar 24, 2025

  12202 Langstaff Dr, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,545 Sq Ft
  • Built 2012

  Last Sold Summary

  • $254/SF
  • 8 Days On Market

  Current Estimated Value $384,725

  Last Listing Agent Milagros Agostini-Prado AK GLOBAL REALTY LLC

  12202 Langstaff Dr, Windermere, FL 34786
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  Est $991,646 Not Listed For Sale

  13981 Reams Rd, Windermere, FL 34786

  13981 Reams Rd, Windermere, FL 34786
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  $2,999,500

  • 5 Beds
  • 4 Baths
  • 3,461 Sq Ft

  5067 Sawyer Cove Way, Windermere, FL 34786

  STUNNING CUSTOM estate in the exclusive GATED community of Sawyer Sound - a private enclave of just 20 luxury homes, ideally located near top-rated public and private schools, excellent dining, and premiere entertainment. Built under the meticulous supervision of its owners, one of whom is an accomplished interior designer, this home showcases exceptional quality and attention to detail. With

  Denise Crabbe REVEL REALTY LLC

  5067 Sawyer Cove Way, Windermere, FL 34786
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  $695,000 Sold Jun 13, 2025

  116 Main St, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,269 Sq Ft
  • Built 1958

  Last Sold Summary

  • $548/SF
  • 91 Days On Market

  Current Estimated Value $714,615

  Last Listing Agent Adam Judd METROPOLIS R.E. SOLUTIONS, LLC

  116 Main St, Windermere, FL 34786
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  Est $406,680 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,028 Sq Ft

  8213 Mystic View Way Unit 2903, Windermere, FL 34786

  8213 Mystic View Way Unit 2903, Windermere, FL 34786
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  $1,074,989 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,722 Sq Ft

  14421 Crest Palm Ave, Windermere, FL 34786

  Under Construction. The Baldwin floor plan is a thoughtfully designed two-story home featuring 4 spacious bedrooms and 3.5 bathrooms, offering over 3,722 square feet of living space. The first floor boasts an inviting open-concept design, with a large great room adjacent to a dining room, perfect for gatherings and entertaining. The owner’s suite, complete with a walk-in closet and private bath,

  Dream Finders Homes Builder

  14421 Crest Palm Ave, Windermere, FL 34786
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  $305,000 Sold Jun 06, 2025

  8276 Maritime Flag St Unit 110, Windermere, FL 34786

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft
  • Built 2007

  Last Sold Summary

  • 7% Below List Price
  • $212/SF
  • 62 Days On Market

  Current Estimated Value $311,640

  Last Listing Agent Evan Caulfield STOCKWORTH REALTY GROUP

  8276 Maritime Flag St Unit 110, Windermere, FL 34786
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  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,060 Sq Ft

  8112 Buena Vista Resort Dr Unit 2303, Orlando, FL 32821

  8112 Buena Vista Resort Dr Unit 2303, Orlando, FL 32821
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  $474,900

  • 3 Beds
  • 2.5 Baths
  • 2,113 Sq Ft

  13757 Bressler Aly, Windermere, FL 34786

  Enjoy a low maintenance lifestyle with this two-story townhome, built in 2019, seconds from modern conveniences in the heart of Windermere. This well-maintained townhouse offers a comfortable living environment with a brand new roof, gutters, downspouts, and additional upgrades, resulting in a low electric bill, making it ready for years of memories. An open, combined main living space welcomes

  Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

  13757 Bressler Aly, Windermere, FL 34786
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  $653,250 Sold Mar 28, 2025

  12761 Westside Village Loop, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,463 Sq Ft
  • Built 2018

  Last Sold Summary

  • 5% Below List Price
  • $265/SF
  • 9 Days On Market

  Current Estimated Value $645,212

  Last Listing Agent Eric Jia NUMBER 1 BROKER, LLC

  12761 Westside Village Loop, Windermere, FL 34786
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  /26

  Est $557,781 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,178 Sq Ft

  4325 Blue Major Dr, Windermere, FL 34786

  4325 Blue Major Dr, Windermere, FL 34786
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  $2,725,000

  • 7 Beds
  • 4 Baths
  • 4,482 Sq Ft

  9648 Weatherstone Ct, Windermere, FL 34786

  Welcome to this exceptional lakefront estate in the exclusive gated community of Weatherstone, ideally situated on the serene shores of Lake Olivia in Windermere, Florida. This beautifully appointed residence offers 7 bedrooms, 4 full bathrooms & a rare combination of timeless architecture & modern luxury. From the moment you arrive, the home's curb appeal is undeniable. The expansive wrap-around

  Olga Jakubowski ERA GRIZZARD REAL ESTATE

  9648 Weatherstone Ct, Windermere, FL 34786
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  $825,000 Sold May 15, 2025

  8738 Iron Mountain Trail, Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,127 Sq Ft
  • Built 2013

  Last Sold Summary

  • 13% Below List Price
  • $264/SF
  • 313 Days On Market

  Current Estimated Value $819,234

  Last Listing Agent Crystal Washington Booth CENTURY 21 BE3

  8738 Iron Mountain Trail, Windermere, FL 34786
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  Est $2,061,424 Not Listed For Sale

  • 6 Beds
  • 5.5 Baths
  • 4,380 Sq Ft

  11840 Vinci Dr, Windermere, FL 34786

  11840 Vinci Dr, Windermere, FL 34786
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  $355,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,155 Sq Ft

  13833 Ancilla Blvd, Windermere, FL 34786

  Under contract-accepting backup offers. Welcome to this ONE STORY TOWNHOME on a CORNER LOT that has been beautifully UPDATED! Step inside onto luxury laminate flooring as you take in the open concept floor plan and freshly painted interior. Being an end unit, this home is lined with windows to allow in lots of natural lighting. The 2 bedrooms are on separate ends of the home for privacy when

  Jacquelyn Voigt KELLER WILLIAMS REALTY AT THE LAKES

  13833 Ancilla Blvd, Windermere, FL 34786
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  $920,000 Sold Jan 15, 2025

  9323 Westover Club Cir, Windermere, FL 34786

  • 4 Beds
  • 4 Baths
  • 3,923 Sq Ft
  • Built 2001

  Last Sold Summary

  • 6% Below List Price
  • $235/SF
  • 45 Days On Market

  Current Estimated Value $931,108

  Last Listing Agent Brigitte Knott CHARLES RUTENBERG REALTY ORLANDO

  9323 Westover Club Cir, Windermere, FL 34786
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  Est $755,436 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,365 Sq Ft

  6929 Corley Ave, Windermere, FL 34786

  6929 Corley Ave, Windermere, FL 34786
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  $739,000

  • 5 Beds
  • 3 Baths
  • 2,972 Sq Ft

  6965 Tettenhall Ln, Windermere, FL 34786

  Welcome to own this beautiful home in lakes of windermere . 5 bedrooms 3 full bathrooms that has been remodeled . Marble floor through downstairs and laminate upstairs and a lot of upgrades throughout the house . The house is looking over a stunning view of a pond with a water fountain and looking everyday at the Disney fireworks . Perfectly situated minutes from all the attractions Disney ,

  Nabil Chakrouni VISION HOME REAL ESTATE, LLC

  6965 Tettenhall Ln, Windermere, FL 34786
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  $1,240,000 Sold May 02, 2025

  7587 Lake Albert Dr, Windermere, FL 34786

  • 6 Beds
  • 6.5 Baths
  • 5,149 Sq Ft
  • Built 2014

  Last Sold Summary

  • 5% Below List Price
  • $241/SF
  • 40 Days On Market

  Current Estimated Value $1,224,086

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

  7587 Lake Albert Dr, Windermere, FL 34786
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  Est $2,074,927 Not Listed For Sale

  • 5 Beds
  • 6.5 Baths
  • 5,382 Sq Ft

  1128 Estancia Woods Loop, Windermere, FL 34786

  1128 Estancia Woods Loop, Windermere, FL 34786
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  $1,044,989 New Construction

  • 6 - 7 Beds
  • 4.5 Baths
  • 4,443 Sq Ft

  Sweetwater Plan at Palms at Windermere, Windermere, FL 34786

  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, workspaces, or entertainment

  Dream Finders Homes Builder

  14207 Crest Palm Ave Unit 36469004, Windermere, FL 34786
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  $600,000 Sold Jul 09, 2025

  5063 Carillon Ln, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 2,406 Sq Ft
  • Built 2004

  Last Sold Summary

  • $249/SF
  • 7 Days On Market

  Current Estimated Value $579,899

  Last Listing Agent Jared Dunn LIVE MVRK LLC

  5063 Carillon Ln, Windermere, FL 34786
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  Est $704,713 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,013 Sq Ft

  6764 Bridgewater Village Rd, Windermere, FL 34786

  6764 Bridgewater Village Rd, Windermere, FL 34786
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  $850,000

  • 5 Beds
  • 4.5 Baths
  • 2,871 Sq Ft

  11774 Via Lucerna Cir, Windermere, FL 34786

  HOME Sweet Home on this beautiful , quiet , established neighborhood of BELMERE IN WINDERMERE ORLANDO FLORIDAThis beautiful house on a gated community with fantastic amenities, such as fitness center large community pool tennis court. Have easy access to food shopping and beautiful restaurants and shopping center. Drive away to Universal Studios , and

  Perlita Aquino PAPP REALTY, INC.

  11774 Via Lucerna Cir, Windermere, FL 34786
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  $535,000 Sold Feb 13, 2025

  5230 Lemon Twist Ln, Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 2,196 Sq Ft
  • Built 2005

  Last Sold Summary

  • $244/SF
  • 0 Days On Market

  Current Estimated Value $540,226

  Last Listing Agent Francisco Nieves-Taranto CT HOMES REALTY CORPORATION

  5230 Lemon Twist Ln, Windermere, FL 34786
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  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,332 Sq Ft

  8256 Maritime Flag St Unit 1715, Windermere, FL 34786

  8256 Maritime Flag St Unit 1715, Windermere, FL 34786
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  $949,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 3,662 Sq Ft

  13224 Swansea Ave, Windermere, FL 34786

  Under contract-accepting backup offers. 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

  Darrell Nunnelley VINTAGE REALTY GROUP LLC

  13224 Swansea Ave, Windermere, FL 34786
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  $1,650,000 Sold Sep 29, 2025

  4108 Downeast Ln, Windermere, FL 34786

  • 4 Beds
  • 3 Baths
  • 3,150 Sq Ft
  • Built 1979

  Last Sold Summary

  • 50% Below List Price
  • $524/SF
  • 208 Days On Market

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  4108 Downeast Ln, Windermere, FL 34786
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  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,476 Sq Ft

  8265 Maritime Flag St Unit 22b-5, Windermere, FL 34786

  8265 Maritime Flag St Unit 22b-5, Windermere, FL 34786
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  $399,000

  • 3 Beds
  • 2.5 Baths
  • 1,629 Sq Ft

  14155 Ancilla Blvd, Windermere, FL 34786

  Welcome to 14155 Ancilla Blvd, a charming three-bedroom, two-and-a-half-bathroom townhouse in the desirable Windermere community. This 1,629 square foot home offers a comfortable layout with a convenient ground-floor primary bedroom suite, perfect for easy living or hosting guests. The property features a bright colonial design with well-maintained landscaping that creates great curb appeal.

  Maritza Saint Hilaire COMPASS FLORIDA LLC

  14155 Ancilla Blvd, Windermere, FL 34786
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  $4,000,000 Sold Apr 07, 2025

  5183 Isleworth Country Club Dr, Windermere, FL 34786

  • Land
  • 0.71 Acre
  • $5,633,803 per Acre

  Last Sold Summary

  • 0 Days On Market

  Current Estimated Value $3,925,252

  Last Listing Agent Michelle Corbin ISLEWORTH REALTY LLC

  5183 Isleworth Country Club Dr, Windermere, FL 34786
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  Est $379,218 Not Listed For Sale

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

  14324 Desert Haven St Unit 4001, Windermere, FL 34786

  14324 Desert Haven St Unit 4001, Windermere, FL 34786
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  $499,999

  • 4 Beds
  • 3 Baths
  • 1,786 Sq Ft

  12060 Via Caselli Ln, Windermere, FL 34786

  One or more photo(s) has been virtually staged. Welcome to this well-maintained 4-bedroom, 3-bathroom townhome offering nearly 1,800 square feet of comfortable living in a desirable community. Perfectly situated directly across from the community pool, this home provides convenience and a prime location.Inside, you’ll find a bright and open floor plan with spacious living and dining areas,

  Avani Shah COLDWELL BANKER REALTY

  12060 Via Caselli Ln, Windermere, FL 34786
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  $1,350,000 Sold Oct 30, 2025

  11425 Claymont Cir, Windermere, FL 34786

  • 5 Beds
  • 4 Baths
  • 3,684 Sq Ft
  • Built 1999

  Last Sold Summary

  • 10% Below List Price
  • $366/SF
  • 99 Days On Market

  Last Listing Agent Ken Pozek REAL BROKER, LLC

  11425 Claymont Cir, Windermere, FL 34786

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