16,483

Windermere, FL Homes

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  • /87

    $2,225,000

    $70K PRICE DROP Under Contract
    • 4 Beds
    • 5.5 Baths
    • 5,722 Sq Ft

    1136 Lake Whitney Dr, Windermere, FL 34786

    Under contract-accepting backup offers. Experience resort-style living in the exclusive Villa D’Este, a masterpiece of sophistication designed by the renowned Arlington Homes. Positioned on the pristine shores of Lake Whitney, this estate welcomes you with a grand 20-foot entryway featuring a custom rustic wrought-iron chandelier and immediate, unobstructed water views.The main floor is a

    Agent Photo

    Mauro Costa

    WILLIAM RAVEIS FLORIDA, LLC

    1136 Lake Whitney Dr, Windermere, FL 34786
  • /17

    $3,870 Per Month

    • 5 Beds
    • 4.5 Baths
    • 2,944 Sq Ft
    • House for Rent

    11719 Bella Milano Ct, Windermere, FL 34786

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $4134.90. That covers your base rent, $3870.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    11719 Bella Milano Ct, Windermere, FL 34786
  • /2

    $580,000

    Sold Apr 13, 2026

    7451 Fairgrove Ave, Windermere, FL 34786

    • 3 Beds
    • 2 Baths
    • 2,092 Sq Ft
    • Built 2017

    Last Sold Summary

    • $277/SF
    • 51 Days On Market

    Current Estimated Value $573,504

    Last Listing Agent Lorraine da Silva Andrade TALENT REALTY SOLUTIONS

    7451 Fairgrove Ave, Windermere, FL 34786
    • /2

      Est $1,022,993

      Not Listed For Sale

      1947 Broadleaf Ct, Windermere, FL 34786

      • 5 Beds
      • 3.5 Baths
      • 3,646 Sq Ft
      • Built 1989
      1947 Broadleaf Ct, Windermere, FL 34786

      Last Sold Summary

      • 64 Days On Market

      Last Listing Agent Kevin Sullivan LAKESIDE REALTY WINDERMERE INC

  • /40

    $930,000

    Open Sun 1:30PM - 4PM $120K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,820 Sq Ft

    6752 Trellis Vine Loop, Windermere, FL 34786

    Virtually Staged. Rare Privacy. Exceptional Space. The Windermere Lifestyle You've Been Waiting For.Experience one of Windermere's most unique opportunities to own a spacious, modern home with a level of privacy rarely found in today's market.Situated on a premium homesite with no rear neighbors, no front-facing neighbors, and no neighbor on the left side, this beautifully designed

    Agent Photo

    Candice Collins

    COLDWELL BANKER REALTY

    6752 Trellis Vine Loop, Windermere, FL 34786
  • /20

    $6,500 Per Month

    • 5 Beds
    • 5 Baths
    • 3,835 Sq Ft
    • House for Rent

    7231 Sangalla Dr, Windermere, FL 34786

    Property Id: 2781998 APPLICATION AND VERIFIABLE PROOF OF FUNDS/INCOME REQUIRED PRIOR TO SCHEDULING A PRIVATE SHOWING. Experience luxury living in the highly sought-after gated Casa Del Lago community in Windermere. This beautifully maintained 5-bedroom, 5 bath home offers 3,835 sq. ft. of spacious living with an open floor plan, primary suite on the first floor, private office, formal

    7231 Sangalla Dr, Windermere, FL 34786
  • /2

    $1,000,000

    Sold Oct 27, 2025

    5235 W Lake Butler Rd, Windermere, FL 34786

    • Land
    • 29,620 Sq Ft
    • $1,470,588 per Acre

    Last Sold Summary

    • 53% Below List Price
    • 211 Days On Market

    Current Estimated Value $1,008,510

    Last Listing Agent Andrew Burgard CHARLES RUTENBERG REALTY ORLANDO

    5235 W Lake Butler Rd, Windermere, FL 34786
    • /2

      Est $1,855,559

      Not Listed For Sale

      12860 Jacob Grace Ct, Windermere, FL 34786

      • 5 Beds
      • 4.5 Baths
      • 5,844 Sq Ft
      • Built 2004
      12860 Jacob Grace Ct, Windermere, FL 34786

      Last Sold Summary

      • 149 Days On Market

      Last Listing Agent Matt Tomaszewski CORCORAN PREMIER REALTY

  • /14

    $1,000,000

    • Land
    • 2.71 Acres
    • $369,004 per Acre

    11544 Willow Gardens Dr, Windermere, FL 34786

    Rare Waterfront Estate Opportunity in Windermere. Discover an exceptional opportunity to build your dream home on over 2.72 acres in the Willows at Lake Rhea community. This remarkable homesite offers approximately 150 feet of lake frontage and breathtaking water views from every angle.Enjoy the serenity of Lake Rhea in your backyard and a private pond in the front, creating a truly unique

    Agent Photo

    Cheryl Rozanski

    JC FLORIDA REALTY LLC

    11544 Willow Gardens Dr, Windermere, FL 34786
  • /13

    $1,542 Per Month

    • 1 Bed
    • 1 Bath
    • 542 Sq Ft
    • Condo for Rent

    13644 Tortona Ln Unit 1/1, Windermere, FL 34786

    ? Flexible Living • Great Value • Windermere ? CODE: RVRS 2628 ?? 1 Bedroom | ?? 1 Bathroom ?? Starting at 542 Sq. Ft. ?? Starting at $1,542/month ?? Minimum 3-month lease ?? Tortona Lane, Windermere, FL 34786 A perfect option if you want flexibility, comfort, and a space that fits your lifestyle. ? ?? Highlights ? Functional 1-bedroom layout ?

    13644 Tortona Ln Unit 1/1, Windermere, FL 34786
  • /2

    $735,000

    Sold Oct 23, 2025

    12821 Westside Village Loop, Windermere, FL 34786

    • 5 Beds
    • 3.5 Baths
    • 3,689 Sq Ft
    • Built 2018

    Last Sold Summary

    • 2% Below List Price
    • $199/SF
    • 15 Days On Market

    Current Estimated Value $762,804

    Last Listing Agent Eric Jia NUMBER 1 BROKER, LLC

    12821 Westside Village Loop, Windermere, FL 34786
    • /2

      Est $1,058,323

      Not Listed For Sale

      76 Oakdale St, Windermere, FL 34786

      • 3 Beds
      • 1.5 Baths
      • 2,011 Sq Ft
      • Built 1957
      76 Oakdale St, Windermere, FL 34786

      Last Sold Summary

      • 82 Days On Market

      Last Listing Agent Bill Martini BHHS FLORIDA REALTY

  • /53

    $449,000

    • 3 Beds
    • 2.5 Baths
    • 1,919 Sq Ft

    12333 Via Derna Place, Windermere, FL 34786

    Welcome to 12333 Via Derna Pl, a beautifully updated townhome located in the highly desirable Carrington community of Windermere. Offering 1,919 sq. ft. of living space, this spacious 3-bedroom, 2.5-bath home features a bright open-concept floor plan designed for both comfortable everyday living and entertaining. Recent updates to the family room, kitchen, and shared bathroom give the home a

    Agent Photo

    Marco Romero

    KARDOSH REALTY

    12333 Via Derna Place, Windermere, FL 34786
  • /13

    $1,950 Per Month

    • 2 Beds
    • 2 Baths
    • 1,123 Sq Ft
    • Condo for Rent

    13644 Tortona Ln Unit 2/2, Windermere, FL 34786

    ? More Space • Flexible Living • Windermere ? CODE: RVRS 2629 ?? 2 Bedrooms | ?? 2 Bathrooms ?? **Starting at 1,123 Sq. Ft.** ?? **Starting at $2,080/month** ?? **Minimum 3-month lease** ?? Tortona Lane, Windermere, FL 34786 A spacious layout that gives you comfort, flexibility, and room to live the way you want. ? ?? Highlights ? Open and functional

    13644 Tortona Ln Unit 2/2, Windermere, FL 34786
  • /2

    $725,000

    Sold Jul 10, 2026

    11903 Cave Run Ave, Windermere, FL 34786

    • 4 Beds
    • 3.5 Baths
    • 3,413 Sq Ft
    • Built 2014

    Last Sold Summary

    • 3% Below List Price
    • $212/SF
    • 74 Days On Market

    Current Estimated Value $742,175

    Last Listing Agent Yan Zheng LOKATION

    11903 Cave Run Ave, Windermere, FL 34786
    • /2

      Est $505,545

      Not Listed For Sale

      12751 Calderdale Ave, Windermere, FL 34786

      • 3 Beds
      • 2 Baths
      • 1,696 Sq Ft
      • Built 2012
      12751 Calderdale Ave, Windermere, FL 34786

      Last Sold Summary

      • 102 Days On Market

      Last Listing Agent Hojin Chang RE/MAX PRIME PROPERTIES

  • /56

    $710,999

    • 4 Beds
    • 3.5 Baths
    • 2,745 Sq Ft

    13239 Jervey St, Windermere, FL 34786

    *This home can be purchased with NO INCOME VERIFICATION.* Welcome to 13239 Jervey Street, an elegant 4-bedroom, 3.5-bath residence offering 2,745 square feet in the highly sought-after Lake Sawyer South community of Windermere. A grand entry with soaring ceilings, crown molding, and refined formal living and dining spaces sets a sophisticated tone from the start.The chef-inspired kitchen

    Agent Photo

    Jamil C. Winston (Jay)

    LPT REALTY, LLC

    13239 Jervey St, Windermere, FL 34786
  • /23

    $9,500 Per Month

    • 5 Beds
    • 7 Baths
    • 5,205 Sq Ft
    • House for Rent

    11406 Waterstone Loop Dr, Windermere, FL 34786

    Welcome to Waterstone Windermere, with tranquil living and charm, this area boasts connecting lakes, ideal for boating and walking. this property consist of 5 bedrooms, 5 full bathrooms and 2 half baths. it’s 10-15 mins drive from Disney many restaurants and bars, Reputable schools and many other features.

    Kimroy Mussington WEICHERT REALTORS HALLMARK PRO

    11406 Waterstone Loop Dr, Windermere, FL 34786
  • /2

    $1,274,000

    Sold Mar 27, 2026

    12779 Westside Village Loop, Windermere, FL 34786

    • 5 Beds
    • 3.5 Baths
    • 3,689 Sq Ft
    • Built 2018

    Last Sold Summary

    • $345/SF
    • 5 Days On Market

    Current Estimated Value $1,222,383

    Last Listing Agent Ramon Brandão WEBB FLORIDA REALTY LLC

    12779 Westside Village Loop, Windermere, FL 34786
    • /2

      Est $596,330

      Not Listed For Sale

      8359 Lookout Pointe Dr, Windermere, FL 34786

      • 4 Beds
      • 4 Baths
      • 2,604 Sq Ft
      • Built 2016
      8359 Lookout Pointe Dr, Windermere, FL 34786

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Pilar Fernandez SIX STAR REALTY GROUP LLC

  • /65

    $2,099,000

    Open Tue 4PM - 6PM $186K PRICE DROP
    • 6 Beds
    • 6 Baths
    • 5,031 Sq Ft

    713 Main St, Windermere, FL 34786

    Seller is offering up to $40,000 toward Buyer’s allowable closing costs, prepaids, and/or rate buy-down with acceptable offer. Pool Possibility! The accompanying video has been digitally altered to illustrate what the property could look like with a pool added. The property currently does not include a pool; however, there is potential to add one.... Come experience the character and charm of

    Agent Photo

    Kari Fleck

    THE REAL ESTATE COLLECTION LLC

    713 Main St, Windermere, FL 34786
  • /8

    $7,500 Per Month

    • 4 Beds
    • 3 Baths
    • 3,244 Sq Ft
    • House for Rent

    6119 Foxfield Ct, Windermere, FL 34786

    Explore luxurious living in this modern Keenes Pointe rental home, seamlessly blending elegance and comfort. Embrace the picturesque views of the golf course from your backyard. Recently updated with tasteful tile throughout, the interior boasts three bedrooms on the first floor, including a master suite and a spacious office. The second floor features a large bedroom with a walk in closet and a

    6119 Foxfield Ct, Windermere, FL 34786
  • /2

    $350,000

    Sold Feb 04, 2026

    7462 Bentonshire Ave, Windermere, FL 34786

    • 3 Beds
    • 2.5 Baths
    • 1,480 Sq Ft
    • Built 2007

    Last Sold Summary

    • 9% Below List Price
    • $236/SF
    • 185 Days On Market

    Current Estimated Value $351,949

    Last Listing Agent Ivan Petkov FLORIDA REALTY INVESTMENTS

    7462 Bentonshire Ave, Windermere, FL 34786
    • /2

      Est $734,254

      Not Listed For Sale

      12995 Westside Village Loop, Windermere, FL 34786

      • 4 Beds
      • 3.5 Baths
      • 2,935 Sq Ft
      • Built 2018
      12995 Westside Village Loop, Windermere, FL 34786

      Last Sold Summary

      • 78 Days On Market

      Last Listing Agent Maria Ubillus FOLIO REALTY LLC

  • /22

    $650,000

    • Land
    • 16,552 Sq Ft
    • $1,710,526 per Acre

    618 Ridgewood Dr, Windermere, FL 34786

    A rare opportunity to build your dream home in the heart of Old Windermere. This cleared, vacant parcel consists of 7 total lots being offered for the first time — a truly unique chance to secure land in the Town of Windermere before it's gone.Enjoy golf cart-friendly streets, access to the famed Butler Chain of Lakes, and the convenience of natural gas and county water already available.

    Agent Photo

    Judy Black

    UPSIDE REAL ESTATE INC

    618 Ridgewood Dr, Windermere, FL 34786
  • /24

    $4,500 Per Month

    • 4 Beds
    • 4 Baths
    • 3,140 Sq Ft
    • House for Rent

    14422 Crest Palm Ave, Windermere, FL 34786

    Located in the desirable Windermere area, this beautifully designed residence offers the perfect blend of luxury, comfort, and convenience. Step through the welcoming foyer and immediately appreciate the thoughtful layout. To the right, you'll find the first spacious bedroom, followed by a full bathroom and a second generously sized bedroom. As you continue through the home, you'll be greeted by

    Lan Lee REAL BROKER, LLC

    14422 Crest Palm Ave, Windermere, FL 34786
  • /2

    $2,400,000

    Sold May 05, 2026

    8402 Lake Burden Cir Unit 2, Windermere, FL 34786

    • 5 Beds
    • 6.5 Baths
    • 6,248 Sq Ft
    • Built 2004

    Last Sold Summary

    • 16% Below List Price
    • $384/SF
    • 163 Days On Market

    Current Estimated Value $2,440,830

    Last Listing Agent Toni Marie Cafferty COMPASS FLORIDA LLC

    8402 Lake Burden Cir Unit 2, Windermere, FL 34786
    • /87

      Est $764,655

      Not Listed For Sale

      4313 Blue Major Dr, Windermere, FL 34786

      • 5 Beds
      • 4.5 Baths
      • 3,512 Sq Ft
      • Built 2014
      4313 Blue Major Dr, Windermere, FL 34786

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Li Xue AGENT GROUP REALTY

  • /67

    $1,150,000

    Pending
    • 5 Beds
    • 4 Baths
    • 3,971 Sq Ft

    8394 Lookout Pointe Dr, Windermere, FL 34786

    FREE DISNEY FIREWORKS show nightly with purchase! Perfectly positioned in the highly sought-after community of Windermere Trails, this beautifully updated home overlooks picturesque Lake Reams and offers the kind of lifestyle that makes people fall in love with Central Florida. From the stately elevation featuring stone accents, a tile roof, paver driveway, and elegant color palette, you'll

    Agent Photo

    Autumn Makin

    LAKEFIELD REALTY GROUP LLC

    8394 Lookout Pointe Dr, Windermere, FL 34786
  • /41

    $2,850 Per Month

    • 3 Beds
    • 2 Baths
    • 1,866 Sq Ft
    • House for Rent

    8556 Greenbank Blvd, Windermere, FL 34786

    Come view this 3 bed/2 bath Windermere home located in the gated community of The Preserve at the Lakes of Windermere! Inside, you'll find crown molding, wainscoting, vaulted ceilings, plenty of natural light, and tile floors throughout the home! The open kitchen is equipped with stainless steel appliances, a subway tile backsplash, quartz countertops, an island, and a pantry closet.

    8556 Greenbank Blvd, Windermere, FL 34786
  • /47

    $1,069,989

    Sold Jan 22, 2026

    14427 Crest Palm Ave, Windermere, FL 34786

    • 5 Beds
    • 4.5 Baths
    • 4,571 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $234/SF
    • 15 Days On Market

    Current Estimated Value $1,050,188

    Dream Finders Homes Palms at Windermere

    14427 Crest Palm Ave, Windermere, FL 34786
    • /52

      Est $2,979,583

      Not Listed For Sale

      1336 Lake Olivia Ln, Windermere, FL 34786

      • 5 Beds
      • 6 Baths
      • 6,227 Sq Ft
      • Built 2019
      1336 Lake Olivia Ln, Windermere, FL 34786

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Mary Currie BHHS FLORIDA REALTY

  • /33

    $979,989

    New Construction $69K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,740 Sq Ft

    14353 Crest Palm Ave, Windermere, FL 34786

    This Arlington home perfectly blends luxury, functionality, and comfort. This brand new 2,740 square foot residence sits on a wooded lot, offering expansive indoor and outdoor living space, ready for immediate move-in. Key Features:4 Spacious Bedrooms: Designed for privacy and flexibility, including a luxurious owner’s suite with spa-like en-suite bathroom and large walk-in closet.3 Full

    Agent Photo

    Cindy Sapp

    OLYMPUS EXECUTIVE REALTY INC

    14353 Crest Palm Ave, Windermere, FL 34786
  • /22

    $3,300 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,139 Sq Ft
    • House for Rent

    6526 Golden Dewdrop Trail, Windermere, FL 34786

    Welcome to 6526 Golden Dewdrop Trail, a freshly painted, move-in-ready home overlooking community green space with views toward the pool in desirable Windermere Landings. This inviting two-story residence offers approximately 2,139 square feet with 3 bedrooms, 2.5 bathrooms, a spacious upstairs loft, and a rear-entry 2-car garage. A covered front porch and second-floor balcony create attractive

    Sergio Duarte FLORIDA LEGACY REALTY LLC

    6526 Golden Dewdrop Trail, Windermere, FL 34786
  • /2

    $1,355,000

    Sold Jul 10, 2026

    1703 Roberts Landing Rd, Windermere, FL 34786

    • 4 Beds
    • 4.5 Baths
    • 3,288 Sq Ft
    • Built 1996

    Last Sold Summary

    • 19% Below List Price
    • $412/SF
    • 278 Days On Market

    Current Estimated Value $1,461,786

    Last Listing Agent Wui Keong Goh INTERNATIONAL NETWORK REALTY

    1703 Roberts Landing Rd, Windermere, FL 34786
    • /2

      Est $824,063

      Not Listed For Sale

      8330 Vivaro Isle Way, Windermere, FL 34786

      • 5 Beds
      • 3.5 Baths
      • 3,465 Sq Ft
      • Built 2018
      8330 Vivaro Isle Way, Windermere, FL 34786

      Last Sold Summary

      • 112 Days On Market

      Last Listing Agent Alex Vastardis COLDWELL BANKER REALTY

  • /30

    $1,545,000

    $50K PRICE DROP
    • Land
    • 2.12 Acres
    • $728,774 per Acre

    10948 Down Park Ln, Windermere, FL 34786

    LAST REMAINING LOT OF THE FOUR IN THIS EXCLUSIVE PRIVATE ESTATE LAKEFRONT COMMUNITY! Rare opportunity to build your dream home in the highly sought after Town of Windermere. This exceptional vacant homesite offers over 2.12 acres and is the largest buildable lot within this private gated enclave of only four estate properties, providing exceptional privacy and generous spacing between homes. The

    Agent Photo

    Andrew Kincaid

    BHHS FLORIDA REALTY

    10948 Down Park Ln, Windermere, FL 34786
  • /33

    $3,895 Per Month

    • 5 Beds
    • 3.5 Baths
    • 3,292 Sq Ft
    • House for Rent

    1349 Whitney Isles Dr, Windermere, FL 34786

    Welcome to this beautifully renovated 5-bedroom home in the prestigious gated community of Whitney Isles at Belmere in Windermere. The home has just been freshly painted and features an impressive floor plan with plenty of space and privacy.The main level features formal living and dining areas, a spacious gourmet kitchen with granite countertops, stainless steel appliances, abundant

    1349 Whitney Isles Dr, Windermere, FL 34786
  • /2

    $975,000

    Sold Apr 01, 2026

    7545 Lake Albert Dr, Windermere, FL 34786

    • 4 Beds
    • 5 Baths
    • 3,425 Sq Ft
    • Built 2008

    Last Sold Summary

    • 11% Below List Price
    • $285/SF
    • 158 Days On Market

    Current Estimated Value $966,073

    Last Listing Agent Nicole Mickle OLYMPUS EXECUTIVE REALTY INC

    7545 Lake Albert Dr, Windermere, FL 34786
    • /2

      Est $1,403,601

      Not Listed For Sale

      7431 Lake Albert Dr, Windermere, FL 34786

      • 6 Beds
      • 6.5 Baths
      • 4,634 Sq Ft
      • Built 2014
      7431 Lake Albert Dr, Windermere, FL 34786

      Last Sold Summary

      • 56 Days On Market

      Last Listing Agent Andy Neal THE AGENCY FL

Showing Results 41 - 80, Page 2 of 18

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