16,516

Windermere, FL Homes

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  • /100

    $5,250,000 Pending

    • 6 Beds
    • 8 Baths
    • 7,818 Sq Ft

    9713 Endicott Ct, Windermere, FL 34786

    Experience elevated lakefront living in this beautifully updated estate, within the prestigious guard gated golf community of Keene’s Pointe, offering direct access to the Butler Chain of Lakes. With over $850,000 in upgrades, this home is perfectly positioned to capture breathtaking sunset views and nightly Disney fireworks from the primary suite. This home delivers a rare combination of

    Agent Photo

    Amy Moline

    EXP REALTY LLC

    (689) 329-1750

    9713 Endicott Ct, Windermere, FL 34786
  • /24

    $2,150 Per Month

    • 2 Beds
    • 2 Baths
    • 1,161 Sq Ft
    • Condo for Rent

    11564 Mizzon Dr Unit 109, Windermere, FL 34786

    Beautiful ground floor unit in the Lakes of Windermere! This unit features 2 bedrooms, 2 bathrooms, ceramic tile flooring throughout and elegant crown molding in the living areas. The kitchen is complete with granite countertops, a breakfast bar and pantry. There is a separate dining area and living room that leads to the large screened in porch. The split floor plan allows privacy, and each

    Agent Photo

    Nicholas Wild

    GATE PROPERTIES & MANAGEMENT INC

    (689) 946-0298

    11564 Mizzon Dr Unit 109, Windermere, FL 34786
  • /2

    $750,000 Sold Sep 18, 2025

    14654 Yellow Butterfly Rd, Windermere, FL 34786

    • 5 Beds
    • 3.5 Baths
    • 3,094 Sq Ft
    • Built 2015

    Last Sold Summary

    • 6% Below List Price
    • $242/SF
    • 44 Days On Market

    Current Estimated Value $731,838

    Last Listing Agent Elijah Lewis FLORIDA IN MOTION REALTY INC

    14654 Yellow Butterfly Rd, Windermere, FL 34786
    • /2

      Est $981,967 Not Listed For Sale

      9332 Windy Ridge Rd, Windermere, FL 34786

      • 4 Beds
      • 3.5 Baths
      • 2,892 Sq Ft
      • Built 1985
      9332 Windy Ridge Rd, Windermere, FL 34786

      Last Sold Summary

      • 2% Above List Price
      • $332/SF
      • 8 Days On Market
      • Last Sold Price $960,000
      • May 07, 2025

      Last Listing Agent Rodney Melendez CORCORAN PREMIER REALTY

  • /74

    $1,349,900 Pending

    • 7 Beds
    • 4.5 Baths
    • 4,563 Sq Ft

    11658 Hampstead St, Windermere, FL 34786

    **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 11658 Hampstead Street, a refined Windermere showpiece tucked inside the highly sought-after Enclave community, zoned for Orange County’s top-rated schools. This home defines elevated Florida living, offering

    Agent Photo

    Thomas Nickley

    KELLER WILLIAMS REALTY AT THE PARKS

    (689) 319-8390

    11658 Hampstead St, Windermere, FL 34786
  • /91

    Starting at $1,575 Per Month

    • 1 - 3 Beds

    13644 Tortona Ln, Windermere, FL 34786

    Addison At Windermere is located at 13644 Tortona Lane Windermere, FL and is managed by GrayCo Properties, LLC, a reputable property management company. Addison At Windermere offers 1 to 3 bedroom apartments ranging in size from 592 to 1508 sq.ft. Amenities include Microwave and more. This rental community is pet friendly, welcoming both cats and dogs. Property is located in the 34786 ZIP code.

    Addison At Windermere

    (689) 600-3552

    13644 Tortona Ln, Windermere, FL 34786
  • /2

    $2,350,000 Sold Oct 14, 2025

    1003 Oakdale St, Windermere, FL 34786

    • 6 Beds
    • 5.5 Baths
    • 4,599 Sq Ft
    • Built 2003

    Last Sold Summary

    • 22% Below List Price
    • $511/SF
    • 280 Days On Market

    Current Estimated Value $2,341,060

    Last Listing Agent Darrell Nunnelley VINTAGE REALTY GROUP LLC

    1003 Oakdale St, Windermere, FL 34786
    • /2

      Est $1,000,501 Not Listed For Sale

      12820 Butler Bay Ct, Windermere, FL 34786

      • 5 Beds
      • 4 Baths
      • 4,127 Sq Ft
      • Built 1989
      12820 Butler Bay Ct, Windermere, FL 34786

      Last Sold Summary

      • 20% Above List Price
      • $201/SF
      • 24 Days On Market
      • Last Sold Price $831,200
      • May 08, 2025

      Last Listing Agent John Muccigrosso RE/MAX

  • /51

    $1,166,989 New Construction

    • 6 Beds
    • 4 Baths
    • 3,550 Sq Ft

    14383 Crest Palm Ave, Windermere, FL 34786

    ELLINGTON II - Our beautiful huge 2 story home, with 6 Bedrooms and 4 Baths. This great floor plan boasts an open concept family/dining/kitchen area along with a formal dining room, gourmet kitchen, extended 42 cabinets and an extended island. Primary Suite on 1st floor along with an additional bedroom & bath. The primary bath also contains a spa package with upgraded 3/8 glass enclosure, an

    Agent Photo

    Cindy Sapp

    OLYMPUS EXECUTIVE REALTY INC

    14383 Crest Palm Ave, Windermere, FL 34786
  • /32

    $3,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,855 Sq Ft
    • House for Rent

    3636 Lake Buynak Rd, Windermere, FL 34786

    Looking for seclusion? One plus acre waterfront. No HOA. Adorable, clean available June 1st. Bring your boat, RV, pets. Quiet treed drive located near the Town of Windermere. Complete with stainless appliances, washer, dryer. Large screened porch. Tile floors throughout. Decorative fireplace in family room. Room to Breathe!! Check it out today. For Application:

    Agent Photo

    Judy Black

    UPSIDE REAL ESTATE INC

    (689) 329-3220

    3636 Lake Buynak Rd, Windermere, FL 34786
  • /2

    $1,000,000 Sold Jun 26, 2025

    11415 N Camden Commons Dr, Windermere, FL 34786

    • 4 Beds
    • 3 Baths
    • 3,034 Sq Ft
    • Built 2005

    Last Sold Summary

    • 9% Below List Price
    • $330/SF
    • 15 Days On Market

    Current Estimated Value $1,008,924

    Last Listing Agent Christina Fata REAL BROKER, LLC

    11415 N Camden Commons Dr, Windermere, FL 34786
    • /2

      Est $1,956,681 Not Listed For Sale

      11954 Provincial Way, Windermere, FL 34786

      • 4 Beds
      • 4.5 Baths
      • 4,800 Sq Ft
      • Built 2005
      11954 Provincial Way, Windermere, FL 34786

      Last Sold Summary

      • 2% Below List Price
      • $417/SF
      • 23 Days On Market
      • Last Sold Price $1,999,900
      • May 08, 2025

      Last Listing Agent Brigitte Elzarki COLDWELL BANKER REALTY

  • /47

    $725,000

    • 5 Beds
    • 3 Baths
    • 2,464 Sq Ft

    7174 Beek St, Windermere, FL 34786

    Welcome to this solid built 1-story 5 bedroom split plan, 3 full baths home with 2464 square feet of well designed living space, plus a 3 car garage and no rear neighbor as it backs to the brick wall of Windermere Terrace. Inside you'll find soaring 10' ceilings & 6-incht baseboards throughout, crown moldings in the family/kitchen area, ceramic tile in the kitchen & bathrooms and engineered wood

    Agent Photo

    Ron Hernquist

    RE/MAX CENTRAL REALTY

    (407) 257-2700

    7174 Beek St, Windermere, FL 34786
  • /87

    Starting at $1,945 Per Month

    • 1 - 2 Beds

    1231 Arya Way, Ocoee, FL 34761

    Discover refined active adult living at Arya at Windermere, a premier 55+ community offering luxury and vibrancy of Windermere. Our spacious one- and two-bedroom residences feature impressive finishes and thoughtful designs that elevate everyday living. Residents enjoy resort-style amenities including a massage room, steam room, and a host of social and wellness opportunities in a pet-friendly

    Arya at Windermere

    (689) 600-1108

    1231 Arya Way, Ocoee, FL 34761
  • /2

    $753,000 Sold Jan 21, 2026

    11660 Delwick Dr, Windermere, FL 34786

    • 4 Beds
    • 4.5 Baths
    • 3,051 Sq Ft
    • Built 2004

    Last Sold Summary

    • 16% Below List Price
    • $247/SF
    • 146 Days On Market

    Current Estimated Value $779,295

    Last Listing Agent Natalie Rosario FATHOM REALTY FL LLC

    11660 Delwick Dr, Windermere, FL 34786
    • /2

      Est $472,534 Not Listed For Sale

      10655 Village Lake Rd, Windermere, FL 34786

      • 4 Beds
      • 3.5 Baths
      • 1,938 Sq Ft
      • Built 2014
      10655 Village Lake Rd, Windermere, FL 34786

      Last Sold Summary

      • 2% Above List Price
      • $240/SF
      • 10 Days On Market
      • Last Sold Price $465,000
      • May 09, 2025

      Last Listing Agent Steven Horner RE/MAX

  • /70

    $325,000

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

    8180 Boat Hook Loop Unit 108/301, Windermere, FL 34786

    Discover the best of Windermere living in this meticulously maintained 3-bedroom, 2-bath CORNER UNIT condo in Lakeside at Lakes of Windermere. An expansive wrap-around screened porch embraces tranquil views and Florida breezes while providing an ideal space for morning coffee or evening relaxation. Inside, the open-concept layout features silestone countertops, cherry cabinets, and stainless

    Agent Photo

    Erin Aaron

    EXP REALTY LLC

    (689) 300-6265

    8180 Boat Hook Loop Unit 108/301, Windermere, FL 34786
  • /51

    Starting at $1,585 Per Month

    • 1 - 3 Beds

    11353 Citra Cir, Windermere, FL 34786

    Experience the finest apartments in Windermere, Florida at The Citra at Windermere. Our apartment community offers a variety of distinctive one, two, and three bedroom apartment homes. Conveniently located, Citra at Windermere is walking distance to shopping, restaurants and entertainment. In addition, we are located within some of the top rated schools in Orange county, including Bay

    Citra at Windermere

    (689) 600-2081

    11353 Citra Cir, Windermere, FL 34786
  • /2

    $849,000 Sold Dec 09, 2025

    11108 Ledgement Ln Unit 2, Windermere, FL 34786

    • 4 Beds
    • 3.5 Baths
    • 3,024 Sq Ft
    • Built 2003

    Last Sold Summary

    • $281/SF
    • 3 Days On Market

    Current Estimated Value $853,095

    Last Listing Agent Terrie Giles KELLER WILLIAMS CLASSIC

    11108 Ledgement Ln Unit 2, Windermere, FL 34786
    • /2

      Est $402,368 Not Listed For Sale

      7776 Rigby St, Windermere, FL 34786

      • 3 Beds
      • 2.5 Baths
      • 1,545 Sq Ft
      • Built 2012
      7776 Rigby St, Windermere, FL 34786

      Last Sold Summary

      • 2% Below List Price
      • $265/SF
      • 28 Days On Market
      • Last Sold Price $409,000
      • May 07, 2025

      Last Listing Agent Maria Parra NAIM REAL ESTATE LLC

  • /72

    $2,500,000

    • 5 Beds
    • 5.5 Baths
    • 5,696 Sq Ft

    105 Pine St, Windermere, FL 34786

    Extraordinary multigenerational living opportunity in the Town of Windermere, where mature oak trees and a quiet, established setting create a true sense of place just moments from the Butler Chain of Lakes. Set on an oversized, over half-acre corner lot in downtown Windermere, this custom home offers a rare blend of privacy, flexibility, and walkability to local dining, coffee shops, boutiques,

    Agent Photo

    Tiffany Pantozzi

    ALIGN REAL ESTATE LLC

    (689) 334-1402

    105 Pine St, Windermere, FL 34786
  • /117

    Starting at $2,148

    Total Monthly Price

    • 1 - 3 Beds

    6506 San Francesco Way, Windermere, FL 34786

    A beautiful community with luxury one, two and three-bedroom apartment homes with a Mediterranean flair.We invite you to transport yourself to an upgraded level of luxury right at your front door. Every finish is hand-selected with the finest touch to make every day surpass the next. Our elegant, resort-inspired amenities have a level of sophistication youll find awe-inspiring day and night.

    Venetian Isle

    (689) 600-3104

    6506 San Francesco Way, Windermere, FL 34786
  • /2

    $840,646 Sold Mar 30, 2026

    4926 Indian Deer Rd, Windermere, FL 34786

    • 5 Beds
    • 4.5 Baths
    • 3,849 Sq Ft
    • Built 2006

    Last Sold Summary

    • 12% Below List Price
    • $218/SF
    • 135 Days On Market

    Current Estimated Value $842,936

    Last Listing Agent Shelley Dawson COMPASS FLORIDA LLC

    4926 Indian Deer Rd, Windermere, FL 34786
    • /2

      Est $767,754 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

      • 2% Below List Price
      • $266/SF
      • 78 Days On Market
      • Last Sold Price $780,000
      • Jul 31, 2024

      Last Listing Agent Maria Ubillus FOLIO REALTY LLC

  • /45

    $1,299,000

    • 6 Beds
    • 3.5 Baths
    • 3,364 Sq Ft

    2219 Ridgewind Way, Windermere, FL 34786

    Set behind the gates of The Estates at Windermere—an intimate enclave of just 67 homes—2219 Ridgewind Way is the kind of property that stops you mid-scroll. A true Victorian-inspired residence, its architectural presence is unforgettable: a statement turret, wraparound porch, and intricate trim work that feels both rare and timeless in today’s market. It’s not just different—it’s irreplaceable.

    Agent Photo

    Hilary Hall

    COMPASS FLORIDA LLC

    (407) 233-3382

    2219 Ridgewind Way, Windermere, FL 34786
  • /25

    Starting at $1,785

    Total Monthly Price

    • 1 - 3 Beds

    101 Casa Mirella Way, Windermere, FL 34786

    Welcome to Casa Mirella Apartments, where lakeside living meets luxury in the heart of Windermere, FL. Enjoy sunny Florida days by the resort-style swimming pool, stay active in the fully equipped fitness center, or relax with friends at the picnic area with outdoor grills. Your furry friend will love the dog park at our luxury apartments in Windermere, FL, and you’ll appreciate the peace of mind

    Casa Mirella

    (689) 407-8119

    101 Casa Mirella Way, Windermere, FL 34786
  • /2

    $862,000 Sold Jan 08, 2026

    299 W 4th Ave, Mount Dora, FL 32757

    • 4 Beds
    • 3 Baths
    • 2,410 Sq Ft
    • Built 1984

    Last Sold Summary

    • 4% Below List Price
    • $358/SF
    • 35 Days On Market

    Last Listing Agent Judy Black UPSIDE REAL ESTATE INC

    299 W 4th Ave, Mount Dora, FL 32757
    • /87

      Est $756,209 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

      • 5% Below List Price
      • $226/SF
      • 7 Days On Market
      • Last Sold Price $795,000
      • Jun 28, 2024

      Last Listing Agent Li Xue AGENT GROUP REALTY

  • /32

    $455,000

    • 3 Beds
    • 2.5 Baths
    • 2,002 Sq Ft

    13733 Bressler Aly, Windermere, FL 34786

    Location location location!! This beautiful 3 bedrooms, 2 1/2 baths, includes a spacious open floor plan with a breakfast bar in the kitchen area and Living Room/Dining Room Combo. Master Bedroom is located on the second floor, as well as two more bedrooms. This two car garage townhouse has a charming front porch which overlooks the pond and offers, not one, but two community pools and a

    Agent Photo

    Robert Welker, III

    CORCORAN PREMIER REALTY

    (689) 336-7911

    13733 Bressler Aly, Windermere, FL 34786
  • /43

    Starting at $1,770 Per Month

    • 1 - 3 Beds

    7826 Crosswater Trail, Windermere, FL 34786

    TOUR YOUR WAY! We have a tour to fit your needs- virtual, self-guided, or agent-guided. Discover resort-style living at MAA Crosswater in Windermere, FL. Garden tubs, double vanity sinks, and washer/dryer units are featured in these one-, two-, and three-bedroom apartment homes. Admire the lake view from our sparkling swimming pool and cabana, or dig your toes in the sand \"beach\" lounging area.

    MAA Crosswater

    (689) 407-5674

    7826 Crosswater Trail, Windermere, FL 34786
  • /2

    $599,000 Sold May 21, 2025

    6963 Northwich Dr, Windermere, FL 34786

    • 4 Beds
    • 2.5 Baths
    • 3,068 Sq Ft
    • Built 2007

    Last Sold Summary

    • $195/SF
    • 3 Days On Market

    Current Estimated Value $616,160

    Last Listing Agent Simi Lakhani KELLER WILLIAMS CLASSIC

    6963 Northwich Dr, Windermere, FL 34786
    • /52

      Est $2,995,254 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

      • 3% Below List Price
      • $498/SF
      • 27 Days On Market
      • Last Sold Price $3,100,000
      • Jul 03, 2024

      Last Listing Agent Mary Currie BHHS FLORIDA REALTY

  • /38

    $1,120,000

    • 6 Beds
    • 4.5 Baths
    • 4,625 Sq Ft

    13525 Gorgona Isle Dr, Windermere, FL 34786

    One or more photo(s) has been virtually staged. Set within the highly sought-after Windermere Isle community, this exceptional estate offers elevated living defined by space, craftsmanship, and an unbeatable location just minutes from Walt Disney World. Featuring 6 bedrooms, 4.5 bathrooms, and over 4,600 square feet, the home is thoughtfully designed for both everyday living and effortless

    Agent Photo

    Roo Klaers

    COLDWELL BANKER REALTY

    (407) 842-8447

    13525 Gorgona Isle Dr, Windermere, FL 34786
  • /35

    Starting at $1,528 Per Month

    • 1 - 3 Beds

    11598 Lachlan Ln, Windermere, FL 34786

    TOUR YOUR WAY! We have a tour to fit your needs- virtual, self-guided, or agent-guided. Call MAA Windermere home in Windermere, FL. Our one-, two-, and three-bedroom apartment homes have all of the modern conveniences you're looking for. Select apartments feature spacious showers, double vanities, and soaking tubs. All units come with a washer/dryer and lots of natural light. Enjoy an expansive

    MAA Windermere

    (689) 407-5825

    11598 Lachlan Ln, Windermere, FL 34786
  • /2

    $389,000 Sold Nov 07, 2025

    6327 Southbridge St, Windermere, FL 34786

    • 3 Beds
    • 2.5 Baths
    • 1,490 Sq Ft
    • Built 2007

    Last Sold Summary

    • 8% Below List Price
    • $261/SF
    • 169 Days On Market

    Current Estimated Value $382,433

    Last Listing Agent Vanessa Lee COLDWELL BANKER REALTY

    6327 Southbridge St, Windermere, FL 34786
    • /30

      Est $858,513 Not Listed For Sale

      8460 Elba Isle Ct, Windermere, FL 34786

      • 4 Beds
      • 3 Baths
      • 2,690 Sq Ft
      • Built 2018
      8460 Elba Isle Ct, Windermere, FL 34786

      Last Sold Summary

      • 2% Below List Price
      • $327/SF
      • 26 Days On Market
      • Last Sold Price $880,000
      • Jun 23, 2023

      Last Listing Agent Paul Baker RE/MAX

  • /56

    $775,000 Pending

    • 4 Beds
    • 3 Baths
    • 2,449 Sq Ft

    9164 Patrimonio Loop, Windermere, FL 34786

    This home checks all the boxes, nightly Disney Magic Kingdom fireworks views, 4 bedrooms, 3 bathrooms, built in 2020, an oversized 0.27-acre fully fenced lot, a heated saltwater pool with a private tropical backyard, a chef’s kitchen with dual ovens and upgraded cabinetry, and a spacious lawn surrounded by lush landscaping for true outdoor living. Experience elevated living just moments from the

    Agent Photo

    Lisa Grinceri

    KELLER WILLIAMS REALTY AT THE LAKES

    (689) 329-3084

    9164 Patrimonio Loop, Windermere, FL 34786
  • /20

    $3,960 Per Month

    • 4 Beds
    • 3 Baths
    • 2,970 Sq Ft
    • House for Rent

    9042 Arbors Edge Trail, Windermere, FL 34786

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home is priced to rent and won't be around for long. Apply now, while we make this home ready for you, or call to arrange a meeting with your local Progress Residential leasing specialist

    (689) 225-0584

    9042 Arbors Edge Trail, Windermere, FL 34786
  • /2

    $750,000 Sold Nov 12, 2025

    13254 Penshurst Ln, Windermere, FL 34786

    • 5 Beds
    • 3.5 Baths
    • 3,720 Sq Ft
    • Built 2015

    Last Sold Summary

    • 6% Below List Price
    • $202/SF
    • 96 Days On Market

    Current Estimated Value $750,529

    Last Listing Agent Hilary Hall COMPASS FLORIDA LLC

    13254 Penshurst Ln, Windermere, FL 34786
    • /2

      Est $1,384,995 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

      • 1% Below List Price
      • $302/SF
      • 56 Days On Market
      • Last Sold Price $1,400,000
      • Sep 13, 2024

      Last Listing Agent Andy Neal THE AGENCY FL

Showing Results 1 - 40, Page 1 of 18

Home Trends in Windermere, FL

Housing Trends

Median Sale Price
$830,000
Median Single Family Sale Price
$1,099,989
Median Townhouse Sale Price
$392,000
Median 2 Bedroom Sale Price
$295,000
Average Price Per Sq Ft
$365
Number of Homes for Sale
249
Last 12 months Home Sales
659
Months of Supply
4.50
Median List Price
$975,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-1%
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