16,485

Windermere, FL Homes

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  • /69

    $2,474,000

    $76K PRICE DROP
    • 5 Beds
    • 7 Baths
    • 5,366 Sq Ft

    6288 Blakeford Dr, Windermere, FL 34786

    Positioned on a corner homesite along the 18th hole of the Golden Bear Club within the guard-gated community of Keene's Pointe, this thoughtfully updated custom home offers five bedrooms, four full bathrooms, and three half bathrooms, combining exceptional golf-front living with breathtaking views of the golf course, pool, and surrounding landscape. A grand foyer welcomes guests with a soaring

    Keith Renner NECTAR REAL ESTATE

    6288 Blakeford Dr, Windermere, FL 34786
  • /25

    $3,500 Per Month

    • 5 Beds
    • 4.5 Baths
    • 2,874 Sq Ft
    • House for Rent

    1125 Lascala Dr, Windermere, FL 34786

    Mediterranean-style 5-bedroom, 4.5-bath residence offering 2,874 square feet in gated Belmere Village. The flexible two-story floor plan includes a first-floor bedroom adjacent to a full bath, ideal for use as a private home office, guest suite or multigenerational space. Upstairs, the spacious primary suite features crown molding and a large walk-in closet, along with three additional

    Charles Woolley BHHS FLORIDA REALTY

    1125 Lascala Dr, Windermere, FL 34786
  • /2

    $3,250,000

    Sold Jun 24, 2026

    8340 Lake Burden Cir, Windermere, FL 34786

    • 6 Beds
    • 7 Baths
    • 6,848 Sq Ft
    • Built 2008

    Last Sold Summary

    • $475/SF
    • 7 Days On Market

    Current Estimated Value $3,263,218

    Last Listing Agent Jill Davis CHARLES RUTENBERG REALTY ORLANDO

    8340 Lake Burden Cir, Windermere, FL 34786
    • /2

      Est $1,104,000

      Not Listed For Sale

      14262 Crest Palm Ave, Windermere, FL 34786

      • 4 Beds
      • 3.5 Baths
      • 3,404 Sq Ft
      • Built 2025
      14262 Crest Palm Ave, Windermere, FL 34786

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  • /57

    $470,000

    $20K PRICE DROP Under Contract
    • 3 Beds
    • 2.5 Baths
    • 1,825 Sq Ft

    8266 Bryce Canyon Ave, Windermere, FL 34786

    Under contract-accepting backup offers. PRICE IMPROVEMENT – EXCEPTIONAL SINGLE-FAMILY HOME VALUE IN WINDERMERE!If you've been searching for the perfect combination of location, condition, lifestyle, and value, this Windermere home deserves your attention.Situated on a desirable corner lot, this move-in-ready home offers additional outdoor space, great curb appeal, and a spacious,

    Mahmoud Mango DALTON WADE INC

    8266 Bryce Canyon Ave, Windermere, FL 34786
  • /51

    $4,300 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,203 Sq Ft
    • House for Rent

    9241 Patrimonio Loop, Windermere, FL 34786

    Beautiful single-story home for lease in the desirable Windermere community of Legado! Built in 2020 and set on a premium conservation lot with no rear neighbors. This 3-bedroom + den, 2.5-bath home offers privacy, modern finishes, and an open floorplan perfect for everyday living. The oversized kitchen island, quartz countertops, and stainless steel appliances create an inviting space for

    Bruna Sereno SELECTA REALTY LLC

    9241 Patrimonio Loop, Windermere, FL 34786
  • /2

    $1,085,000

    Sold Dec 03, 2025

    14389 Crest Palm Ave, Windermere, FL 34786

    • 6 Beds
    • 4.5 Baths
    • 4,443 Sq Ft
    • Built 2024

    Last Sold Summary

    • 10% Below List Price
    • $244/SF
    • 10 Days On Market

    Current Estimated Value $1,129,685

    Last Listing Agent Cindy Sapp OLYMPUS EXECUTIVE REALTY INC

    14389 Crest Palm Ave, Windermere, FL 34786
    • /2

      Est $1,077,136

      Not Listed For Sale

      14291 Crest Palm Ave, Windermere, FL 34786

      • 6 Beds
      • 4 Baths
      • 4,222 Sq Ft
      • Built 2024
      14291 Crest Palm Ave, Windermere, FL 34786

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  • /35

    $5,390,000

    $470K PRICE DROP Pre-Foreclosure
    • 4 Beds
    • 7 Baths
    • 7,872 Sq Ft

    12264 Montalcino Cir, Windermere, FL 34786

    Lakefront, Luxurious, home with Private Pool in Windermere. A True Paradise! Discover this rare gem in the heart of Windermere,located in the gated community of Casa Del Lago — a spectacular residence that combines sophistication, comfort, and stunning lake views. with over eight expertly designed rooms, this home was carefully customized by the builder down to the smallest detail — from

    Jennifer Paiano Olmeda WRA BUSINESS & REAL ESTATE

    12264 Montalcino Cir, Windermere, FL 34786
  • /75

    $5,000 Per Month

    • 6 Beds
    • 4 Baths
    • 4,176 Sq Ft
    • House for Rent

    8224 Procida Isle Ln, Windermere, FL 34786

    Stunning house in Windermere Isle in Gas community, Fully Fenced, NO Carpet in the house. Engineer wood floor and porcelain tile in bathrooms. Recent Upgraded kitchen and bathrooms cabinets and countertops and first floor luxury Engineer wood floor. Two downstairs bedrooms are perfect for a guest bedroom and a home office. Tankless gas water heater. Ceiling fan with remote control in all rooms.

    Li Xue AGENT GROUP REALTY

    8224 Procida Isle Ln, Windermere, FL 34786
  • /2

    $1,800,000

    Sold Aug 13, 2026

    5421 Tildens Grove Blvd, Windermere, FL 34786

    • 6 Beds
    • 4.5 Baths
    • 5,922 Sq Ft
    • Built 2005

    Last Sold Summary

    • 10% Below List Price
    • $304/SF
    • 75 Days On Market

    Current Estimated Value $1,986,970

    Last Listing Agent Mike Derenthal DERENTHAL REALTY

    5421 Tildens Grove Blvd, Windermere, FL 34786
    • /2

      Est $1,067,253

      Not Listed For Sale

      14237 Crest Palm Ave, Windermere, FL 34786

      • 4 Beds
      • 3 Baths
      • 2,687 Sq Ft
      • Built 2025
      14237 Crest Palm Ave, Windermere, FL 34786

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  • /23

    $2,950,000

    $1M PRICE DROP Under Contract
    • Land
    • 20.71 Acres
    • $142,443 per Acre

    7545 Ficquette Rd, Windermere, FL 34786

    Under contract-accepting backup offers. Back On The Market! Huge Price Improvement! Approx 20 Acres in a very sought after area of Horizon West by many builders. This land is undeveloped and ready for you to put your stamp on it. Just minutes from Disney. Location, Location, Location!!!

    Susan Graves KELLER WILLIAMS REALTY AT THE LAKES

    7545 Ficquette Rd, Windermere, FL 34786
  • /24

    $3,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,970 Sq Ft
    • House for Rent

    12784 Garridan Ave, Windermere, FL 34786

    Stunning Beautiful Upgraded home in the desirable Wickham Park community in heart of Windermere. NO carpet. Fresh Painting. Perfect location. Top rated schools. Rent includes hoa fee and lawncare. Well-maintained 4 bedroom & 2.5 bath & 1 loft/retreat upstairs & 2 car garage on front. Sizable back yard with extended pave. Open floor plan with lots of upgrades. Great natural light in the whole

    Jacky Liu YORK MILLS REALTY LLC

    12784 Garridan Ave, Windermere, FL 34786
  • /2

    $1,400,000

    Sold Jan 09, 2026

    11474 Claymont Cir, Windermere, FL 34786

    • 5 Beds
    • 4 Baths
    • 3,238 Sq Ft
    • Built 2001

    Last Sold Summary

    • 4% Above List Price
    • $432/SF
    • 5 Days On Market

    Current Estimated Value $1,331,797

    Last Listing Agent Sue Webb WATSON REALTY CORP.

    11474 Claymont Cir, Windermere, FL 34786
    • /2

      Est $8,580,320

      Not Listed For Sale

      5271 Isleworth Country Club Dr, Windermere, FL 34786

      • 7 Beds
      • 13 Baths
      • 11,403 Sq Ft
      • Built 2013
      5271 Isleworth Country Club Dr, Windermere, FL 34786

      Last Sold Summary

      • 206 Days On Market

      Last Listing Agent Monica Lochmandy ISLEWORTH REALTY LLC

  • /42

    $1,450,000

    $80K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,868 Sq Ft

    11015 Hawkshead Ct, Windermere, FL 34786

    Located within the guard gated community of Reserve at Lake Sound in Windermere, this beautifull 5-bedroom, 5-bath residence offers the perfect blend of elegance, comfort, and functionality. Featuring nearly 3,900 square feet of living space, the home showcases tall ceilings, travertine flooring throughout the main living areas, and thoughtful modern updates completed in recent years.A

    Julie Davis, LLC COLDWELL BANKER REALTY

    11015 Hawkshead Ct, Windermere, FL 34786
  • /23

    $2,550 Per Month

    • 3 Beds
    • 2 Baths
    • 1,332 Sq Ft
    • Condo for Rent

    8256 Maritime Flag St Unit 305, Windermere, FL 34786

    Welcome to Lakeside of Windermere, the sought out community conveniently located across from shopping plazas which provide Publix Grocery, restaurants and shops. Enjoy top quality amenities including resort swimming pool, fitness center, clubhouse, playground, outdoor beach volleyball, and fishing pier on Lake Burden. This condo is in a highly desirable area of Windermere, just minutes from

    Melody Niederst IAD REAL ESTATE

    8256 Maritime Flag St Unit 305, Windermere, FL 34786
  • /2

    $849,000

    Sold Jul 01, 2026

    111 Main St, Windermere, FL 34786

    • 3 Beds
    • 2 Baths
    • 2,272 Sq Ft
    • Built 1984

    Last Sold Summary

    • 4% Below List Price
    • $374/SF
    • 12 Days On Market

    Current Estimated Value $849,316

    Last Listing Agent Sammy Nakhleh CENTURY 21 CARIOTI

    111 Main St, Windermere, FL 34786
    • /2

      Est $378,901

      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

      • 26 Days On Market

      Last Listing Agent Bryan Burns RE/MAX DOWNTOWN

  • /66

    $1,795,000

    $100K PRICE DROP
    • 5 Beds
    • 6 Baths
    • 3,728 Sq Ft

    11051 Hawkshead Ct, Windermere, FL 34786

    Back on market due to buyer non-performance WITH PRICE ADJUSTMENT!! Discover an exceptional expression of modern luxury in the heart of Windermere. Welcome to 11051 Hawkshead Court, gracefully positioned within the prestigious Reserve at Lake Butler Sound—an exclusive guard-gated enclave renowned for its elegance, privacy, and lakefront lifestyle.Set on an expansive half-acre homesite at

    Ken Pozek REAL BROKER, LLC

    11051 Hawkshead Ct, Windermere, FL 34786
  • /2

    $2,500,000

    Sold Jan 05, 2026

    2828 Marquesas Ct, Windermere, FL 34786

    • 6 Beds
    • 5.5 Baths
    • 6,819 Sq Ft
    • Built 1989

    Last Sold Summary

    • 33% Below List Price
    • $367/SF
    • 207 Days On Market

    Current Estimated Value $2,548,325

    Last Listing Agent Carolyn Cook DALTON WADE INC

    2828 Marquesas Ct, Windermere, FL 34786
    • /2

      Not Listed For Sale

      14257 Desert Haven St Unit GE, Windermere, FL 34786

      • 3 Beds
      • 2.5 Baths
      • 1,512 Sq Ft
      • Built 2012
      14257 Desert Haven St Unit GE, Windermere, FL 34786

      Last Sold Summary

      • 131 Days On Market

      Last Listing Agent Victor Barroeta MBT REALTY LLC

  • /24

    $780,000

    • 3 Beds
    • 2.5 Baths

    8713 Crescendo Ave, Windermere, FL 34786

    Beautiful and spacious 3-bedroom, 2.5-bath home with 2,497 sq ft of living space, ideally located in the highly desirable Windermere area, just 15 minutes from Magic Kingdom. Built in 2016, this move-in-ready home features a bright open-concept floor plan with expansive living and dining areas, perfect for entertaining and everyday living. The modern kitchen flows seamlessly into the main living

    Zoramir Rodriguez Realty One Group Evolution

    8713 Crescendo Ave, Windermere, FL 34786
  • /2

    $560,000

    Sold Jun 16, 2026

    13430 Hopkinton Ct, Windermere, FL 34786

    • 3 Beds
    • 2 Baths
    • 1,732 Sq Ft
    • Built 2005

    Last Sold Summary

    • 4% Below List Price
    • $323/SF
    • 216 Days On Market

    Current Estimated Value $541,354

    Last Listing Agent Lynn London EXP REALTY LLC

    13430 Hopkinton Ct, Windermere, FL 34786
    • /2

      Est $430,694

      Not Listed For Sale

      5892 Soter Ln, Windermere, FL 34786

      • 3 Beds
      • 2.5 Baths
      • 2,001 Sq Ft
      • Built 2019
      5892 Soter Ln, Windermere, FL 34786

      Last Sold Summary

      • 82 Days On Market

      Last Listing Agent Claire Jesso SERHANT

  • /48

    $690,000

    $60K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,620 Sq Ft

    13842 Orange Crest Dr, Windermere, FL 34786

    Just a short walk to the COMMUNITY BOAT RAMP and PLAYGROUND!!!! Nestled behind the gated enclave of Eden Isle in Summerport, this stunning five-bedroom, three-bath residence blends modern updates with generous living space. Newly renovated in 2024, the home showcases luxury vinyl plank flooring throughout, a reimagined kitchen, and fully upgraded downstairs bathrooms. Step inside to soaring

    Erica Sadelfeld THE REAL ESTATE COLLECTION LLC

    13842 Orange Crest Dr, Windermere, FL 34786
  • /2

    $1,395,000

    Sold Jul 20, 2026

    11413 Camden Park Dr, Windermere, FL 34786

    • 5 Beds
    • 3.5 Baths
    • 3,840 Sq Ft
    • Built 2005

    Last Sold Summary

    • $363/SF
    • 0 Days On Market

    Current Estimated Value $1,296,587

    Last Listing Agent Angela Durruthy KEENE'S POINTE REALTY

    11413 Camden Park Dr, Windermere, FL 34786
    • /2

      Est $1,076,667

      Not Listed For Sale

      14304 Crest Palm Ave, Windermere, FL 34786

      • 5 Beds
      • 3.5 Baths
      • 3,764 Sq Ft
      • Built 2025
      14304 Crest Palm Ave, Windermere, FL 34786

      Last Sold Summary

      • 87 Days On Market

      Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  • /98

    $11,750,000

    $2M PRICE DROP
    • 6 Beds
    • 10 Baths
    • 11,100 Sq Ft

    9832 Laurel Valley Dr, Windermere, FL 34786

    Virtually Staged. A true Lake Butler trophy estate. Set within the world-famous gates of Isleworth and commanding panoramic western sunset water views of Lake Butler from virtually every room, 9832 Laurel Valley Drive offers over 11,000 square feet of luxury lakefront living, situated upon 150 feet of expanded sandy beachfront, thoughtfully enlarged by the current owners, in one of Florida’s most

    Nicholas Taylor REAL BROKER, LLC

    9832 Laurel Valley Dr, Windermere, FL 34786
  • /2

    $6,200,000

    Sold Sep 15, 2025

    11019 Bridge House Rd Unit R, Windermere, FL 34786

    • 7 Beds
    • 11 Baths
    • 9,376 Sq Ft
    • Built 2008

    Last Sold Summary

    • $661/SF
    • 0 Days On Market

    Current Estimated Value $5,984,900

    Last Listing Agent Ronald Ziolkowski RE/MAX PRIME PROPERTIES

    11019 Bridge House Rd Unit R, Windermere, FL 34786
    • /2

      Est $1,053,718

      Not Listed For Sale

      14409 Crest Palm Ave, Windermere, FL 34786

      • 5 Beds
      • 3.5 Baths
      • 3,764 Sq Ft
      • Built 2025
      14409 Crest Palm Ave, Windermere, FL 34786

      Last Sold Summary

      • 50 Days On Market

      Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  • /70

    $7,250,000

    $345K PRICE DROP
    • 5 Beds
    • 6.5 Baths
    • 7,099 Sq Ft

    5074 Isleworth Country Club Dr, Windermere, FL 34786

    A masterfully reimagined golf-front estate, this residence offers an unparalleled standard of luxury within the acclaimed guard-gated community of Isleworth. Completely reimagined and expanded, the residence offers over 7,000 square feet of refined living space, including a 2,400+ square-foot second-story addition designed by acclaimed architect Mark Nasrallah. Situated on over half an acre, the

    Armaan Memarpouri MEM REALTY GROUP

    5074 Isleworth Country Club Dr, 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 $369,071

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

    13550 Carroway St, Windermere, FL 34786
    • /2

      Est $1,085,610

      Not Listed For Sale

      14256 Crest Palm Ave, Windermere, FL 34786

      • 5 Beds
      • 3.5 Baths
      • 3,764 Sq Ft
      • Built 2025
      14256 Crest Palm Ave, Windermere, FL 34786

      Last Sold Summary

      • 128 Days On Market

      Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  • /26

    $460,000

    $5K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,974 Sq Ft

    12353 Via Derna Place, Windermere, FL 34786

    The house does not include furniture.Welcome to this beautifully maintained 3-bedroom, 3-bathroom townhouse, with furniture available for negotiation, located in the desirable Carrington at Windermere community. This residence provides a well-designed open-concept floor plan that seamlessly blends comfort and functionality, ideal for both everyday living and entertaining.The home

    Nathalya Ferreira da Silva AUTHENTIC REAL ESTATE TEAM

    12353 Via Derna Place, 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 $2,225,718

    Last Listing Agent Amanda Black PA UPSIDE REAL ESTATE INC

    409 W 2nd Ave, Windermere, FL 34786
    • /2

      Est $1,193,333

      Not Listed For Sale

      14207 Crest Palm Ave, Windermere, FL 34786

      • 6 Beds
      • 4 Baths
      • 4,222 Sq Ft
      • Built 2024
      14207 Crest Palm Ave, Windermere, FL 34786

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  • /50

    $680,000

    $15K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 2,976 Sq Ft

    6712 Thornhill Cir, Windermere, FL 34786

    With timeless curb appeal and a front porch built for slow mornings, this Windermere home blends classic charm with the upgrades that make everyday life easier. Step inside and the ceilings rise, sunlight floods through, and hardwood floors (2021) lead you through open living and dining spaces that flow seamlessly into a remodeled kitchen with quartz countertops, updated cabinetry, and dual

    Brad Young HOMEVEST REALTY

    6712 Thornhill Cir, Windermere, FL 34786
  • /2

    $1,150,000

    Sold Aug 28, 2026

    109 E 12th Ave, Windermere, FL 34786

    • 4 Beds
    • 3.5 Baths
    • 2,791 Sq Ft
    • Built 1989

    Last Sold Summary

    • 6% Below List Price
    • $412/SF
    • 113 Days On Market

    Current Estimated Value $1,192,408

    Last Listing Agent Judy Black UPSIDE REAL ESTATE INC

    109 E 12th Ave, Windermere, FL 34786

Showing Results 361 - 400, Page 10 of 18

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