16,485

Windermere, FL Homes

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  • /41

    $1,395,000

    $55K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 3,997 Sq Ft

    9548 Crown Prince Ln, Windermere, FL 34786

    Nestled on a rare half-acre lot in one of Windermere’s most sought-after communities, Windsor Hills, this FULLY RENOVATED luxury home delivers the ultimate move-in-ready, like-new lifestyle buyers are searching for. Featuring 4 spacious bedrooms, 4 beautifully updated bathrooms, and a highly desirable open-concept layout, every inch of this residence has been meticulously redesigned with today’s

    Dianna Desboyaux DOUGLAS ELLIMAN

    9548 Crown Prince Ln, Windermere, FL 34786
  • /36

    $2,950 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,092 Sq Ft
    • House for Rent

    11804 Silverlake Park Dr, Windermere, FL 34786

    Move-in ready! This beautiful 4-bedroom, 2.5-bathroom home has been freshly painted throughout and features no carpet! Tile flooring on the first floor and vinyl flooring in all bedrooms. Located in the highly desirable Windermere Trails community, the home is just minutes from Walt Disney World and within walking distance of Bay Lake Elementary School.The first floor offers a bright and

    Cui Li RATIO REAL ESTATE, LLC

    11804 Silverlake Park Dr, Windermere, FL 34786
  • /2

    $1,175,000

    Sold May 22, 2026

    3138 Seigneury Dr, Windermere, FL 34786

    • 4 Beds
    • 4.5 Baths
    • 3,831 Sq Ft
    • Built 1997

    Last Sold Summary

    • 13% Below List Price
    • $307/SF
    • 25 Days On Market

    Current Estimated Value $1,227,394

    Last Listing Agent Rob Rahter STOCKWORTH REALTY GROUP

    3138 Seigneury Dr, Windermere, FL 34786
    • /2

      Est $1,212,418

      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

      • 201 Days On Market

      Last Listing Agent Camila Castrillon COLDWELL BANKER REALTY

  • /34

    $1,500,000

    • 5 Beds
    • 6.5 Baths
    • 5,312 Sq Ft

    13503 Lake Cawood Dr, Windermere, FL 34786

    5 Bed 6 bath custom built home in gated community, 1.02 acre lot with private well for all water supply, NO water or sewer bill. Private Basketball court, overside Pool and Spa, Outdoor Kitchen hookup, granite Counter tops, built in double stainless-steel Oven, built in range. Master Bedroom 1st floor. This house also contains 2 suites, 1 on 1st Floor and another located at the 2nd floor with

    Nicholas Horton BANNER INT'L REAL ESTATE

    13503 Lake Cawood Dr, Windermere, FL 34786
  • /20

    $2,600 Per Month

    • 3 Beds
    • 2.5 Baths
    • Townhouse for Rent

    12355 Langstaff Dr Unit 12355, Windermere, FL 34786

    Spectacular Townhome located in the Lake Reams Townhomes Community in Windermere, FL. Picture this, being minutes away from Walt Disney World and all of their theme parks, fashionable shopping and exceptional restaurants and also having convenient access to all major roadways, you can make this a reality! This townhome includes 3 bedrooms and 2.5 bathrooms with an open floor plan with spacious

    12355 Langstaff Dr Unit 12355, Windermere, FL 34786
  • /2

    $539,900

    Sold Nov 20, 2025

    11091 Bagley Aly, Windermere, FL 34786

    • 4 Beds
    • 2.5 Baths
    • 2,222 Sq Ft
    • Built 2018

    Last Sold Summary

    • 2% Below List Price
    • $243/SF
    • 123 Days On Market

    Current Estimated Value $561,986

    Last Listing Agent Mariana Cezar Ovalle WRA BUSINESS & REAL ESTATE

    11091 Bagley Aly, Windermere, FL 34786
    • /2

      Est $285,900

      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

      • 130 Days On Market

      Last Listing Agent Mark Bridges CHARLES RUTENBERG REALTY ORLANDO

  • /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
  • /21

    $2,350 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,214 Sq Ft
    • Townhouse for Rent

    Unlisted Address

    Welcome to 7365 Brightland Street, a stunning 2-bedroom, 2.5-bathroom end-unit townhome nestled in the highly sought-after Lake Burden Townhome Community in Windermere, FL 34786. Offering 1,308 square feet of pristine living space, this home blends upscale comfort with effortless indoor-outdoor living, just moments from top-tier shopping and world-famous attractions. The second floor features two

    Nedy Trent LPT REALTY, LLC

    Unlisted Address
  • /2

    $975,000

    Sold Oct 20, 2025

    635 Butler St, Windermere, FL 34786

    • 3 Beds
    • 3 Baths
    • 2,353 Sq Ft
    • Built 1924

    Last Sold Summary

    • 2% Below List Price
    • $414/SF
    • 0 Days On Market

    Current Estimated Value $983,298

    Last Listing Agent Scott Arthur KELLER WILLIAMS REALTY AT THE LAKES

    635 Butler St, Windermere, FL 34786
    • /33

      Est $1,033,311

      Not Listed For Sale

      9127 Tintori Ln, Windermere, FL 34786

      • 5 Beds
      • 4 Baths
      • 3,393 Sq Ft
      • Built 2011
      9127 Tintori Ln, Windermere, FL 34786

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Yousef Zeidan RE/MAX PRIME PROPERTIES

  • /52

    $755,000

    $10K PRICE DROP Under Contract
    • 4 Beds
    • 3.5 Baths
    • 3,161 Sq Ft

    7211 Still Pond Ln, Windermere, FL 34786

    Under contract-accepting backup offers. Welcome to this stunning FORMER MODEL HOME in the sought-after ASLIN PARK, a community in the heart of WINDERMERE. This former CUSTOM CARLISLE model was designed and built by renowned ASHTON HOMES. Perfectly positioned on a premium corner lot with not rear neighbor and pond view, located in one of Windermere desired subdivision. This exceptional former

    Arturo Castillo PREFERRED REAL ESTATE BROKERS

    7211 Still Pond Ln, Windermere, FL 34786
  • /31

    $2,350 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,184 Sq Ft
    • Townhouse for Rent

    8524 Danforth Dr, Windermere, FL 34786

    Welcome to Lake Reams Townhomes at Lakes of Windermere. This picturesque community is on the back door of Disney and offers beautiful tree lined streets and sidewalks throughout with a Jr. sized Olympic Swimming Pool and Cabana area. Conveniently located close to great shopping and dining, just around the corner at Lakeside Village. Superior schools in a very desirable location. This 2bed/2.5bath

    Connie Culbertson FIRST INTERNATIONAL REAL ESTAT

    8524 Danforth Dr, Windermere, FL 34786
  • /2

    $385,000

    Sold Jan 26, 2026

    8625 Coventry Park Way, Windermere, FL 34786

    • 3 Beds
    • 2.5 Baths
    • 1,554 Sq Ft
    • Built 2016

    Last Sold Summary

    • 6% Below List Price
    • $248/SF
    • 146 Days On Market

    Current Estimated Value $358,014

    Last Listing Agent Alexandra Mateu BAHIA INTERNATIONAL REALTY

    8625 Coventry Park Way, Windermere, FL 34786
    • /2

      Est $1,836,259

      Not Listed For Sale

      5608 Marleon Dr, Windermere, FL 34786

      • 5 Beds
      • 5.5 Baths
      • 5,228 Sq Ft
      • Built 2015
      5608 Marleon Dr, Windermere, FL 34786

      Last Sold Summary

      • 128 Days On Market

      Last Listing Agent Kyle Madorin UPWELL REALTY LLC

  • /74

    $1,289,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 3,793 Sq Ft

    5746 Oxford Moor Blvd, Windermere, FL 34786

    Under contract-accepting backup offers. Picture your morning here. Coffee on the covered lanai, the pond fountain catching the early light, and an expansive lawn rolling toward the water, with over half an acre between you and the rest of the world. This is 5746 Oxford Moor Blvd, a nearly 3,800-square-foot Mediterranean-style executive home set on one of the finest pond-view lots in gated Oxford

    Kyle Madorin UPWELL REALTY LLC

    5746 Oxford Moor Blvd, Windermere, FL 34786
  • /21

    $2,600 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,724 Sq Ft
    • Townhouse for Rent

    7713 Jailene Dr, Windermere, FL 34786

    Beautiful rental home in the desirable Windermere area featuring a spacious open floor plan, bright living spaces, and a functional layout perfect for comfortable living. Conveniently located near top-rated schools, shopping, dining, golf courses, major highways, and just minutes from Disney, Winter Garden, and Orlando attractions. Don't miss this opportunity to lease a beautiful home in one of

    Carla Lugo NAIM REAL ESTATE LLC

    7713 Jailene Dr, Windermere, FL 34786
  • /2

    $1,069,499

    Sold Nov 18, 2025

    14365 Crest Palm Ave, Windermere, FL 34786

    • 5 Beds
    • 3.5 Baths
    • 3,628 Sq Ft
    • Built 2025

    Last Sold Summary

    • 2% Above List Price
    • $295/SF
    • 0 Days On Market

    Current Estimated Value $1,112,742

    Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

    14365 Crest Palm Ave, Windermere, FL 34786
    • /2

      Est $1,723,108

      Not Listed For Sale

      5566 Marleon Dr, Windermere, FL 34786

      • 5 Beds
      • 6 Baths
      • 4,675 Sq Ft
      • Built 2015
      5566 Marleon Dr, Windermere, FL 34786

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Paul Baker RE/MAX PRIME PROPERTIES

  • /42

    $989,989

    New Construction
    • 4 Beds
    • 4 Baths
    • 3,153 Sq Ft

    14371 Crest Palm Ave, Windermere, FL 34786

    Discover the Arlington with Bonus, a stunning two-story home in the highly desirable town of Windermere, where luxury, flexibility, and everyday comfort come together. Offering 3,153 square feet of thoughtfully designed living space, this move-in-ready home is situated on a private wooded homesite, creating a peaceful backdrop for indoor and outdoor living. Inside, you'll find 4 spacious bedrooms

    Dream Finders Homes Builder
    14371 Crest Palm Ave, Windermere, FL 34786
  • /43

    $7,500 Per Month

    • 6 Beds
    • 4.5 Baths
    • 4,161 Sq Ft
    • Property for Rent

    Unlisted Address

    Welcome to 8304 Lookout Pointe Drive, an exceptional residence nestled in the highly sought-after Windermere Trails community. This beautifully appointed home offers over 4,100 square feet of thoughtfully designed living space, featuring 6 bedrooms, 5 bathrooms, a private office, spacious loft, and a dedicated media room—perfect for modern family living and entertaining.The heart of the

    Caroline Valentino NEWKEY REAL ESTATE LLC

    Unlisted Address
  • /2

    $619,000

    Sold Oct 31, 2025

    13260 Penshurst Ln, Windermere, FL 34786

    • 4 Beds
    • 3 Baths
    • 2,076 Sq Ft
    • Built 2015

    Last Sold Summary

    • 1% Below List Price
    • $298/SF
    • 6 Days On Market

    Current Estimated Value $613,175

    Last Listing Agent Nadia Eggers FUTURE HOME REALTY INC

    13260 Penshurst Ln, Windermere, FL 34786
    • /22

      Est $365,478

      Not Listed For Sale

      11637 Water Run Aly, Windermere, FL 34786

      • 3 Beds
      • 2.5 Baths
      • 1,466 Sq Ft
      • Built 2017
      11637 Water Run Aly, Windermere, FL 34786

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Nia Medina SERHANT

  • /47

    $1,350,000

    $100K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,929 Sq Ft

    1700 Lake Roberts Ct, Windermere, FL 34786

    Welcome to this exceptional luxury residence offering 5 spacious bedrooms, 4 beautifully appointed bathrooms, and 3,929 square feet of refined living space on an expansive homesite of over half an acre. Perfectly positioned in a highly sought-after location, this stunning property combines elegance, comfort, and privacy with resort-style outdoor living. Surrounded by lush, mature landscaping, the

    David Johnston CREEGAN GROUP

    1700 Lake Roberts Ct, Windermere, FL 34786
  • /22

    $14,500 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,836 Sq Ft
    • House for Rent

    6119 Payne Stewart Dr, Windermere, FL 34786

    Among the shores of beautiful Lake Chase within the gates of Isleworth Golf & Country Club, this modern golf villa offers a prime lakefront location in proximity to the Clubhouse. The interior boasts 2,836 square feet of living space, with an open floor plan set against a backdrop of picturesque water views. This completely renovated single-story floor plan, includes built-in bar and dining area,

    Michelle Corbin ISLEWORTH REALTY LLC

    6119 Payne Stewart Dr, Windermere, FL 34786
  • /2

    $950,000

    Sold Sep 03, 2026

    11462 Claymont Cir, Windermere, FL 34786

    • 3 Beds
    • 3 Baths
    • 2,314 Sq Ft
    • Built 2001

    Last Sold Summary

    • 3% Below List Price
    • $411/SF
    • 10 Days On Market

    Current Estimated Value $988,009

    Last Listing Agent Felicia Donateli PALM PROPERTIES OF CF, INC.

    11462 Claymont Cir, Windermere, FL 34786
    • /41

      Est $314,639

      Not Listed For Sale

      Unlisted Address

      • 3 Beds
      • 2.5 Baths
      • 1,512 Sq Ft
      • Built 2013
      Unlisted Address

      Last Sold Summary

      • 99 Days On Market

      Last Listing Agent Vicente Virgilio ALTIS REALTY

  • /100

    $2,899,000

    • 7 Beds
    • 6 Baths
    • 5,122 Sq Ft

    4303 Isabella Cir, Windermere, FL 34786

    Located in one of Windermere’s most sought-after luxury GATED communities with 24-HOUR SECURITY-SCREENED ENTRY, Casabella, this exceptional custom-enhanced ESTATE showcases ultra-modern design, refined craftsmanship, and elevated INDOOR-OUTDOOR LIVING, offering impressive scale, custom design, and an exceptional lifestyle experience. Designed with both scale and functionality in mind, the home

    Gabriella Sadler SERHANT

    4303 Isabella Cir, Windermere, FL 34786
  • /38

    $2,800 Per Month

    • 2 Beds
    • 1 Bath
    • 950 Sq Ft
    • Townhouse for Rent

    7612 Ficquette Rd, Windermere, FL 34786

    Short or long term lease available! Experience waterfront living on 3.31 acres with approximately 150 feet of frontage on Lake Hancock in Windermere. Offered at $2,800 per month, this two bedroom, one bath duplex is available furnished, partially furnished or unfurnished.The residence features warm wood ceilings, exposed wood columns, inside laundry, a water filtration and purification

    Elsie Benitez BENITEZ ROYAL REALTY LLC

    7612 Ficquette Rd, Windermere, FL 34786
  • /2

    $2,583,750

    Sold Aug 27, 2026

    10870 Bayshore Dr, Windermere, FL 34786

    • 4 Beds
    • 5 Baths
    • 4,693 Sq Ft
    • Built 1999

    Last Sold Summary

    • 22% Below List Price
    • $551/SF
    • 153 Days On Market

    Current Estimated Value $2,799,022

    Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    10870 Bayshore Dr, Windermere, FL 34786
    • /2

      Est $8,859,993

      Not Listed For Sale

      9306 Blanche Cove Dr, Windermere, FL 34786

      • 6 Beds
      • 8 Baths
      • 14,856 Sq Ft
      • Built 2022
      9306 Blanche Cove Dr, Windermere, FL 34786

      Last Sold Summary

      • 132 Days On Market

      Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

  • 1841 Windermere Rd Unit 41281963, Windermere, FL

    Price To Be Determined

    New Construction
    • 5 Beds
    • 7 Baths
    • 5,855 Sq Ft

    Bressols Plan at Saddlecrest at Windermere, Windermere, FL

    The Bressols' inviting porch and double-door entry reveal the two-story foyer, expansive living room, and formal dining room, with views to the spacious great room, casual dining area, and desirable covered lanai. The well-equipped kitchen is complete with a large center island with breakfast bar, ample counter and cabinet space, roomy walk-in pantry, and butler pantry to the dining room. The

    Toll Brothers, Inc. Builder
    1841 Windermere Rd Unit 41281963, Windermere, FL
  • /43

    $5,000 Per Month

    • 5 Beds
    • 3.5 Baths
    • 3,725 Sq Ft
    • House for Rent

    8719 Crescendo Ave, Windermere, FL 34786

    Beautifully Furnished Pool Home in Desirable Windermere Trails! This spacious, fully furnished home features an open-concept floor plan with a gourmet kitchen offering stainless steel appliances, granite countertops, tile backsplash, a large center island, walk-in pantry, and dining area overlooking the family room and private screened pool. The first floor includes the luxurious primary suite, a

    Maria Ubillus FOLIO REALTY LLC

    8719 Crescendo Ave, Windermere, FL 34786
  • /2

    $350,000

    Sold Jun 12, 2026

    6528 Helmsley Cir, Windermere, FL 34786

    • 2 Beds
    • 2.5 Baths
    • 1,411 Sq Ft
    • Built 2008

    Last Sold Summary

    • 8% Above List Price
    • $248/SF
    • 8 Days On Market

    Current Estimated Value $346,580

    Last Listing Agent Daniel Rodriguez NEW HEIGHTS REALTY GROUP

    6528 Helmsley Cir, Windermere, FL 34786
    • /2

      Est $367,058

      Not Listed For Sale

      12202 Langstaff Dr, Windermere, FL 34786

      • 3 Beds
      • 2.5 Baths
      • 1,545 Sq Ft
      • Built 2012
      12202 Langstaff Dr, Windermere, FL 34786

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Milagros Agostini-Prado LPT REALTY, LLC

  • /49

    $505,000

    $15K PRICE DROP Under Contract
    • 3 Beds
    • 2.5 Baths
    • 1,725 Sq Ft

    6820 Thornhill Cir, Windermere, FL 34786

    Under contract-accepting backup offers. Welcome to this stunning 2-story home in the highly desirable Lakes of Windermere, featuring 3 bedrooms, 2.5 bathrooms, and a spacious bonus room that can easily serve as a home office, gym, media room, or playroom. The expansive primary suite offers soaring vaulted ceilings, a large walk-in closet, and a spa-inspired in-suite bathroom with a relaxing

    Maria Galindez LIFESTYLE INTERNATIONAL REALTY

    6820 Thornhill Cir, Windermere, FL 34786
  • /44

    $8,900 Per Month

    • 5 Beds
    • 4.5 Baths
    • 4,028 Sq Ft
    • House for Rent

    6020 Marleon Dr, Windermere, FL 34786

    Welcome to 6020 Marleon Drive, an exceptional 5-bedroom, 4-bathroom residence offering over 4,000 square feet of beautifully designed living space in the highly sought-after, guard-gated community of Lake Cypress Cove in Windermere. Set on more than half an acre, this impressive home offers the space, privacy, and amenities to enjoy the best of Florida living. Inside, soaring ceilings and

    Charles Newman UNITED REALTY GROUP INC

    6020 Marleon Dr, Windermere, FL 34786
  • /2

    $960,000

    Sold Feb 23, 2026

    11550 Delwick Dr, Windermere, FL 34786

    • 5 Beds
    • 3 Baths
    • 2,843 Sq Ft
    • Built 2004

    Last Sold Summary

    • 4% Below List Price
    • $338/SF
    • 6 Days On Market

    Current Estimated Value $941,180

    Last Listing Agent Constantino Trimarcchi TRIMARCHI REALTY CORP

    11550 Delwick Dr, Windermere, FL 34786
    • /2

      Est $756,903

      Not Listed For Sale

      8803 Peachtree Park Ct, Windermere, FL 34786

      • 5 Beds
      • 2.5 Baths
      • 2,772 Sq Ft
      • Built 2017
      8803 Peachtree Park Ct, Windermere, FL 34786

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Janice Edwards-Diaz, PA PREMIER SOTHEBYS INT'L REALTY

Showing Results 241 - 280, Page 7 of 18

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