16,485

Windermere, FL Homes

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  • /79

    $775,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 2,224 Sq Ft

    8291 Procida Isle Ln, Windermere, FL 34786

    Under contract-accepting backup offers. Welcome to 8291 Procida Isle Lane, a stunning ONE-STORY 4 bedrooms, 3 full bathrooms POOL home with a TILE roof and 2-car garage in the highly sought-after Windermere Isle community. Offering 2,224 square feet of beautifully designed living space, this meticulously maintained home combines modern upgrades, everyday comfort, and an incredible backyard

    Vlad Kizlo KELLER WILLIAMS REALTY AT THE LAKES

    8291 Procida Isle Ln, Windermere, FL 34786
  • /54

    $2,695 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,540 Sq Ft
    • Townhouse for Rent

    8332 Iron Mountain Trail, Windermere, FL 34786

    BEAUTIFUL 3 bedroom TOWNHOME AT WINDERMERE!Marketing DescriptionWelcome to this beautiful 3-bedroom, 2.5-bathroom townhome in the highly desirable Windermere Trails community! Featuring a spacious and comfortable layout, this home offers a modern kitchen with stainless steel appliances and granite countertops, a convenient stop-and-drop area, and a bright living space perfect for everyday

    Jacob Hara TRANSCEND REALTY

    8332 Iron Mountain Trail, Windermere, FL 34786
  • /2

    $460,000

    Sold Dec 01, 2025

    7673 Ripplepointe Way, Windermere, FL 34786

    • 4 Beds
    • 3 Baths
    • 2,212 Sq Ft
    • Built 2015

    Last Sold Summary

    • 2% Below List Price
    • $208/SF
    • 19 Days On Market

    Current Estimated Value $513,080

    Last Listing Agent Mahmoud Mango DALTON WADE INC

    7673 Ripplepointe Way, Windermere, FL 34786
    • /2

      Est $489,993

      Not Listed For Sale

      11822 Silverlake Park Dr, Windermere, FL 34786

      • 3 Beds
      • 2.5 Baths
      • 1,829 Sq Ft
      • Built 2014
      11822 Silverlake Park Dr, Windermere, FL 34786

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Zheng Liu TRUEPRO REALTY LLC

  • /4

    $1,500,000

    • 4 Beds
    • 3 Baths
    • 3,517 Sq Ft

    11035 Schooner Way, Windermere, FL 34786

    Nestled among the Butler Chain of Lakes in the charming Town of Windermere, this 4-bedroom, 3-bath pool home offers the perfect blend of comfort, space, and tranquility. Located within the sought-after Marina Bay community, the home features a warm and inviting atmosphere, a spacious floor plan designed for everyday living and entertaining, and an oversized lot that provides plenty of room to

    W. Channing Harrison LAKESIDE REALTY WINDERMERE INC

    11035 Schooner Way, Windermere, FL 34786
  • /29

    $2,400 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,363 Sq Ft
    • House for Rent

    8259 Maritime Flag St Unit S, Windermere, FL 34786

    Welcome to 8259 Maritime Flag Street in desirable Windermere! This inviting 3-bedroom, 2.5-bath villa-style condo offers comfortable living in a convenient location. Residents enjoy access to community amenities, including a swimming pool, clubhouse, and fitness center. Just across the street, a shopping center provides easy access to a grocery store, excellent dining options, and additional

    Alfredo Meyer ALTIS REALTY

    8259 Maritime Flag St Unit S, Windermere, FL 34786
  • /2

    $6,000,000

    Sold May 06, 2026

    1002 Down Reserve Ct, Windermere, FL 34786

    • 6 Beds
    • 5.5 Baths
    • 6,706 Sq Ft
    • Built 2021

    Last Sold Summary

    • 13% Below List Price
    • $895/SF
    • 42 Days On Market

    Current Estimated Value $5,954,226

    Last Listing Agent Jennifer Paiano Olmeda WRA BUSINESS & REAL ESTATE

    1002 Down Reserve Ct, Windermere, FL 34786
    • /2

      Est $1,093,333

      Not Listed For Sale

      14415 Crest Palm Ave, Windermere, FL 34786

      • 5 Beds
      • 3.5 Baths
      • 3,764 Sq Ft
      • Built 2025
      14415 Crest Palm Ave, Windermere, FL 34786

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  • /30

    $584,900

    $64K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,050 Sq Ft

    9011 Chapman Oak Ct, Windermere, FL 34786

    Windermere Gem: Updated & Move-In Ready!Discover the perfect blend of modern luxury and prime location in the highly sought-after Windermere area. This beautifully updated home offers an incredible opportunity for homeowners and investors alike, situated just minutes from top-rated schools, premier shopping centers, and fitness facilities.This property has been meticulously

    Shiran Moyal TOWNE CENTER REALTY

    9011 Chapman Oak Ct, Windermere, FL 34786
  • /17

    $3,150 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,014 Sq Ft
    • House for Rent

    11468 Misty Oak Aly, Windermere, FL 34786

    TOP RATED SCHOOLS!!! Welcome to Ashlin Park, one of Windermere’s most desirable communities! Beautifully situated on a private corner lot, this home offers an oversized homesite with breathtaking water views directly in front of the property, creating a peaceful and picturesque setting from the moment you arrive.Featuring 3 bedrooms, 2.5 bathrooms, and a 2-car garage, the home showcases

    Frederico Hexsel KARDOSH REALTY

    11468 Misty Oak Aly, Windermere, FL 34786
  • /2

    $1,300,000

    Sold Aug 18, 2026

    11537 Claymont Cir, Windermere, FL 34786

    • 5 Beds
    • 4 Baths
    • 3,164 Sq Ft
    • Built 2002

    Last Sold Summary

    • 7% Below List Price
    • $411/SF
    • 95 Days On Market

    Current Estimated Value $1,358,743

    Last Listing Agent Julie Bettosini STOCKWORTH REALTY GROUP

    11537 Claymont Cir, Windermere, FL 34786
    • /2

      Est $1,299,843

      Not Listed For Sale

      6720 Winter Garden Vineland Rd, Windermere, FL 34786

      • 5 Beds
      • 4 Baths
      • 3,554 Sq Ft
      • Built 2003
      6720 Winter Garden Vineland Rd, Windermere, FL 34786

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent Rita Schoeffler BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

  • /59

    $1,395,000

    Coming Soon
    • 5 Beds
    • 4 Baths
    • 4,186 Sq Ft

    101 Lee St, Windermere, FL 34786

    Virtually Staged. Nestled in the heart of Windermere, and featuring more than $300,000 in recent improvements including a brand new roof September 2026, this character-rich home offers nearly 4,200 square feet of versatile living space just steps from Windermere's charming downtown. Situated on nearly half an acre, this five-bedroom, four-bath residence pairs distinctive architectural character

    Julie Bettosini STOCKWORTH REALTY GROUP

    101 Lee St, Windermere, FL 34786
  • /39

    $2,600 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,480 Sq Ft
    • Townhouse for Rent

    12355 Langstaff Dr, 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

    Maribel Minarro FLORIDA FANTASY REAL ESTATE INC

    12355 Langstaff Dr, Windermere, FL 34786
  • /2

    $840,000

    Sold Oct 17, 2025

    4509 Indian Deer Rd, Windermere, FL 34786

    • 4 Beds
    • 3 Baths
    • 2,412 Sq Ft
    • Built 2006

    Last Sold Summary

    • 1% Below List Price
    • $348/SF
    • 10 Days On Market

    Current Estimated Value $817,138

    Last Listing Agent Clementine Costantini KELLER WILLIAMS REALTY AT THE LAKES

    4509 Indian Deer Rd, Windermere, FL 34786
    • /2

      Est $315,543

      Not Listed For Sale

      8168 Boat Hook Loop Unit 201/718, Windermere, FL 34786

      • 3 Beds
      • 2 Baths
      • 1,442 Sq Ft
      • Built 2006
      8168 Boat Hook Loop Unit 201/718, Windermere, FL 34786

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Tennille Biggers KELLER WILLIAMS ELITE PARTNERS III REALTY

  • /44

    $1,099,000

    $151K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,390 Sq Ft

    715 Magnolia St, Windermere, FL 34786

    A beautiful home in the heart of downtown Windermere, this property offers four bedrooms and three bathrooms with a perfect blend of comfort, style, and convenience. The main residence features hardwood floors throughout, spacious living areas, and large sliding doors that open to a serene, beautiful backyard — ideal for both entertaining and unwinding.An added highlight is the fully

    Robert Trien IRIS INTERNATIONAL

    715 Magnolia St, Windermere, FL 34786
  • /36

    $2,800 Per Month

    • 4 Beds
    • 3 Baths
    • 1,736 Sq Ft
    • Townhouse for Rent

    12113 Via Caselli Ln, Windermere, FL 34786

    *** Spectrum Cable and Internet are now included***Beautiful 4 bedroom 3 bathroom town-home. This townhome is 1736 square feet of living space, two car garage with opener, first floor guest room and bathroom, and boasts a large living room/kitchen/dining space. The open concept kitchen is bright with natural light and features granite quartz counter countertops, tile flooring throughout, and

    Lisa Hamilton FLORIDA REALTY INVESTMENTS

    12113 Via Caselli Ln, Windermere, FL 34786
  • /2

    $315,000

    Sold Nov 14, 2025

    8271 Maritime Flag St Unit 109, Windermere, FL 34786

    • 3 Beds
    • 2.5 Baths
    • 1,363 Sq Ft
    • Built 2011

    Last Sold Summary

    • 12% Below List Price
    • $231/SF
    • 155 Days On Market

    Last Listing Agent Daniela de Rodriguez B LIVE COMMERCIAL AND RESIDENT

    8271 Maritime Flag St Unit 109, Windermere, FL 34786
    • /2

      Est $327,190

      Not Listed For Sale

      14231 Desert Haven St Unit GE, Windermere, FL 34786

      • 3 Beds
      • 2.5 Baths
      • 1,512 Sq Ft
      • Built 2012
      14231 Desert Haven St Unit GE, Windermere, FL 34786

      Last Sold Summary

      • 36 Days On Market

      Last Listing Agent Mercia Sousa ACCORD REAL ESTATE SERVICES

  • /30

    $560,000

    $15K PRICE DROP Pending
    • 4 Beds
    • 2.5 Baths
    • 2,460 Sq Ft

    7011 Nobleton Dr, Windermere, FL 34786

    Under contract-accepting backup offers. Don't miss an Opportunity to own this Great Craftsman Home overlooking a serene Wooded View, located in the community of Lakes of Windermere. Impeccably maintained and Move-in ready, this 4-bedroom, 2.5-bath home offers numerous Upgrades and Touches throughout. Such as all new kitchen appliances, newly painted interior, new A/C, Hardwood flooring, Water

    Sean Flatley KELLER WILLIAMS REALTY AT THE PARKS

    7011 Nobleton Dr, Windermere, FL 34786
  • /8

    $3,900 Per Month

    • 3 Beds
    • 2 Baths
    • 2,258 Sq Ft
    • House for Rent

    2630 Stanton Hall Ct, Windermere, FL 34786

    The Manors is a Great Neighborhood and next to Windermere Elementary School * Property can be leased short term if needed during renovations or waiting for another home to be built - Call for details and pricing

    Darrell Nunnelley VINTAGE REALTY GROUP LLC

    2630 Stanton Hall Ct, Windermere, FL 34786
  • /2

    $2,075,000

    Sold Feb 09, 2026

    647 Ridgewood Dr, Windermere, FL 34786

    • 3 Beds
    • 3 Baths
    • 2,681 Sq Ft
    • Built 1974

    Last Sold Summary

    • 12% Below List Price
    • $774/SF
    • 373 Days On Market

    Current Estimated Value $2,075,286

    Last Listing Agent Linda O'Grady PREMIER SOTHEBYS INT'L REALTY

    647 Ridgewood Dr, Windermere, FL 34786
    • /2

      Est $364,312

      Not Listed For Sale

      14344 Desert Haven St, Windermere, FL 34786

      • 3 Beds
      • 2.5 Baths
      • 1,840 Sq Ft
      • Built 2013
      14344 Desert Haven St, Windermere, FL 34786

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Gonzalo Senior IRM INVEST., REAL EST.& MGMT.

  • /3

    $1,172,945

    New Construction
    • 5 Beds
    • 3.5 Baths
    • 3,764 Sq Ft

    Deerfield Plan at Palms at Windermere, Windermere, FL 34786

    The Deerfield floorplan is a spacious two-story home designed for growing families, featuring 5 bedrooms and 3.5 bathrooms. This layout offers an ideal combination of private retreats and open gathering spaces. The first floor includes the primary bedroom suite, complete with a luxurious bathroom and walk-in closet, a separate study perfect for working from home, and an expansive great room

    Dream Finders Homes Builder
    14207 Crest Palm Ave Unit 36467792, Windermere, FL 34786
  • /18

    $3,500 Per Month

    • 4 Beds
    • 3 Baths
    • 2,214 Sq Ft
    • House for Rent

    7252 Backwoods Trail, Windermere, FL 34786

    Home at the Ashton Park of Windermere community, 4 bedroom 3 full bath, spacious kitchen with all new stainless steel appliances. Island sink with a bar counter open to breakfast nook and family great room. Formal dining room. Inside Laundry, cabinet desk and laundry storage. Security system installed, cable/internet pre-wired with distribution box. Double garage with 2 separate electric doors.

    Eliza Hawash REALSOURCE PROPERTY MANGNT LLC

    7252 Backwoods Trail, Windermere, FL 34786
  • /2

    $610,000

    Sold Jul 02, 2026

    5224 Lemon Twist Ln, Windermere, FL 34786

    • 4 Beds
    • 3.5 Baths
    • 2,812 Sq Ft
    • Built 2006

    Last Sold Summary

    • 5% Below List Price
    • $217/SF
    • 24 Days On Market

    Current Estimated Value $624,092

    Last Listing Agent Carmen Aridas RE/MAX PRIME PROPERTIES

    5224 Lemon Twist Ln, Windermere, FL 34786
    • /67

      Est $1,146,000

      Not Listed For Sale

      14249 Crest Palm Ave, Windermere, FL 34786

      • 6 Beds
      • 4.5 Baths
      • 4,443 Sq Ft
      • Built 2024
      14249 Crest Palm Ave, Windermere, FL 34786

      Last Sold Summary

      • 25 Days On Market

  • /11

    $825,000

    $173K PRICE DROP
    • Land
    • 1.07 Acres
    • $771,028 per Acre

    13125 Filly Ct, Lake Butler, FL 34786

    A Once In A Lifetime Opportunity to build your dream home in the heart of Windermere within a Private, Equestrian-Friendly Community * The Farms in Windermere consists of 14 larger than 1 Acre Homesites * Flanked by nearly 11 acres of Fully Fenced and Manicured Pasture and Riding Field, Stables, 2 Spring Fed Ponds and Towering Oaks providing shade for the Lucky Horses that make The Farms their

    Darrell Nunnelley VINTAGE REALTY GROUP LLC

    13125 Filly Ct, Lake Butler, FL 34786
  • /12

    $2,300 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,311 Sq Ft
    • Townhouse for Rent

    12543 Cruxbury Dr, Windermere, FL 34786

    A truly magnificent townhome in Windermere, just minutes from Walt Disney World. The solid home design includes concrete block construction on all four walls on the first floor to help insure the minimal energy transfer and the maximum soundproofing. Inside this bright and open layout allows for easy gathering as all common areas join together, living room, kitchen, and breakfast nook, with built

    Caroline Perotti BELLA VIEW REALTY LLC

    12543 Cruxbury Dr, Windermere, FL 34786
  • /2

    $370,000

    Sold Feb 03, 2026

    5235 Keenes Pheasant Dr, Windermere, FL 34786

    • 3 Beds
    • 2.5 Baths
    • 1,462 Sq Ft
    • Built 2004

    Last Sold Summary

    • 14% Below List Price
    • $253/SF
    • 186 Days On Market

    Current Estimated Value $373,911

    Last Listing Agent Ronda Shively COMPASS FLORIDA LLC

    5235 Keenes Pheasant Dr, Windermere, FL 34786
    • /2

      Est $313,709

      Not Listed For Sale

      11564 Mizzon Dr Unit 305/925, Windermere, FL 34786

      • 3 Beds
      • 2 Baths
      • 1,332 Sq Ft
      • Built 2006
      11564 Mizzon Dr Unit 305/925, Windermere, FL 34786

      Last Sold Summary

      • 101 Days On Market

      Last Listing Agent Tennille Biggers KELLER WILLIAMS ELITE PARTNERS III REALTY

  • /20

    $519,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,085 Sq Ft

    4844 Flint Rd, Windermere, FL 34786

    Don’t miss the opportunity to make this beautiful home in the highly sought-after Summerport community your own! Known for its A-rated schools, picturesque surroundings, and outstanding amenities. This well-maintained 3-bedroom, 2-bath home features a versatile office/den, offering flexible space to accommodate a home office, or guest room. The home features vinyl flooring throughout with no

    Kim Lam CORCORAN PREMIER REALTY

    4844 Flint Rd, Windermere, FL 34786
  • /66

    $3,500 Per Month

    • 4 Beds
    • 3 Baths
    • 2,812 Sq Ft
    • House for Rent

    9072 Overlook Pass Dr, Windermere, FL 34786

    Welcome to this freshly updated, move-in-ready 4-bedroom, 3-bathroom home in the highly desired Windermere Trails community! The entire interior freshly painted, featuring rich wood flooring on the main level, a spacious downstairs bedroom, and a full bath with a walk-in shower perfect for guests or multi-generational living. Upstairs, you'll find a massive loft with ample lighting alongside a

    Ravichandra Sathari Mallikarjuna FLORIDA REALTY INVESTMENTS

    9072 Overlook Pass Dr, Windermere, FL 34786
  • /2

    $665,000

    Sold Aug 10, 2026

    13836 Bluebird Pond Rd, Windermere, FL 34786

    • 3 Beds
    • 2 Baths
    • 2,108 Sq Ft
    • Built 2004

    Last Sold Summary

    • 5% Below List Price
    • $315/SF
    • 63 Days On Market

    Current Estimated Value $655,338

    Last Listing Agent Keith Gordon GET MORE OFFERS

    13836 Bluebird Pond Rd, Windermere, FL 34786
    • /2

      Est $2,888,065

      Not Listed For Sale

      5023 Sawyer Cove Way, Windermere, FL 34786

      • 5 Beds
      • 5.5 Baths
      • 4,421 Sq Ft
      • Built 2020
      5023 Sawyer Cove Way, Windermere, FL 34786

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Gordy Singh COMPASS FLORIDA, LLC

  • /41

    $554,555

    $20K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,798 Sq Ft

    9319 Woodbreeze Blvd, Windermere, FL 34786

    WONDERFUL WINDERMERE 4 BED/ 2 BATH HOME LOCATED IN THE CHARMING COMMUNITY OF SILVER WOODS. The moment you drive up to this home you are greeted by low maintence landscaping, paver driveway and a unique courtyard entry which makes this home standout. The courtyard is a perfect space to spend the evenings or start your mornings. Sliders from the kitchen lead onto the courtyard. Upon entering you

    Steven Looper CHARLES RUTENBERG REALTY ORLANDO

    9319 Woodbreeze Blvd, Windermere, FL 34786
  • /18

    $3,195 Per Month

    • 4 Beds
    • 3 Baths
    • 2,686 Sq Ft
    • House for Rent

    8631 Greenbank Blvd, Windermere, FL 34786

    Very nice 2 story home in gated community near Disney employee parking in Windermere, Fl. Spacious formal family and formal dining area on first floor. Carpeting on stairway and throughout second floor. Large master bedroom and luxury primary bath with separate shower and garden tub.

    Joe Thomas CLASSIC 1 REALTY INC

    8631 Greenbank Blvd, Windermere, FL 34786
  • /82

    $2,825,000

    Sold Sep 10, 2026

    13431 Bellaria Cir, Windermere, FL 34786

    • 4 Beds
    • 4.5 Baths
    • 5,616 Sq Ft
    • Built 2010

    Last Sold Summary

    • 13% Below List Price
    • $503/SF
    • 47 Days On Market

    Current Estimated Value $2,408,162

    Last Listing Agent Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

    13431 Bellaria Cir, Windermere, FL 34786
    • /2

      Est $322,091

      Not Listed For Sale

      8256 Maritime Flag St Unit 103, Windermere, FL 34786

      • 3 Beds
      • 2 Baths
      • 1,442 Sq Ft
      • Built 2009
      8256 Maritime Flag St Unit 103, Windermere, FL 34786

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Brad Rosel EXP REALTY LLC

Showing Results 281 - 320, Page 8 of 18

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