16,483

Windermere, FL Homes

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  • /35

    $539,900

    Open Sun 11PM - 2PM $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,819 Sq Ft

    9433 Palm Tree Dr, Windermere, FL 34786

    WELCOME HOME! NEW IMPROVEMENTS! Nestled beneath majestic oak trees in one of Windermere's most desirable communities, this well-maintained 3-bedroom, 2-bath home sits on a quarter of an acre and offers the perfect blend of comfort, privacy, and location. Situated in the highly sought-after 34786 zip code, this exceptional residence features a popular split-bedroom floor plan with 1,819 square

    Agent Photo

    Kitty Mark

    COLDWELL BANKER REALTY

    9433 Palm Tree Dr, Windermere, FL 34786
  • /26

    $4,990 Per Month

    • 4 Beds
    • 3.5 Baths
    • 3,596 Sq Ft
    • House for Rent

    10914 Ledgement Ln, Windermere, FL 34786

    Stunning 4BR/3 full + 2 half bath rental in a gated Windermere community! Enjoy all-tile flooring throughout and your own private in-ground pool. Spacious, low-maintenance, and move-in ready — close to top schools, shopping, and dining. Schedule a showing today!

    Agent Photo

    Rohini Bandaru

    LA ROSA REALTY KISSIMMEE

    10914 Ledgement Ln, 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 $759,120

    Last Listing Agent Elijah Lewis FLORIDA IN MOTION REALTY INC

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

      Est $957,444

      Not Listed For Sale

      14366 Crest Palm Ave, Windermere, FL 34786

      • 4 Beds
      • 3 Baths
      • 2,687 Sq Ft
      • Built 2025
      14366 Crest Palm Ave, Windermere, FL 34786

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

  • /31

    $560,000

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,706 Sq Ft

    13219 Charfield St, Windermere, FL 34786

    Welcome to this charming and inviting home nestled in the highly desirable Lake Sawyer South community in Windermere. As you drive through the neighborhood, you'll immediately appreciate the mature landscaping, beautiful tree-lined streets, and peaceful atmosphere that make this communityso special. Upon arrival, you're greeted by a spacious covered front porch — the perfect place to relax and

    Agent Photo

    Patricia Schraiber

    DENIZ REALTY PARTNERS LLC

    13219 Charfield St, Windermere, FL 34786
  • /91

    Starting at $1,542 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

    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 $2,347,460

    Last Listing Agent Darrell Nunnelley VINTAGE REALTY GROUP LLC

    1003 Oakdale St, Windermere, FL 34786
    • /2

      Est $3,419,411

      Not Listed For Sale

      4065 Isabella Cir, Windermere, FL 34786

      • 6 Beds
      • 8 Baths
      • 8,047 Sq Ft
      • Built 2020
      4065 Isabella Cir, Windermere, FL 34786

  • /70

    $1,399,900

    • 5 Beds
    • 3 Baths
    • 3,356 Sq Ft

    2540 Hempel Cove Ct, Windermere, FL 34786

    Virtually Staged. Set on just over an acre in Windermere, this updated 5-bedroom, 3-bath pool home offers 3,356 square feet of living space, plus a separate flex/bonus room that can be used as a media room, game room, office or additional living space. Located on a cul-de-sac in Lake Down Cove, the property offers something increasingly hard to find in Windermere: an updated home with a private

    Agent Photo

    Tiffany Pantozzi

    ALIGN REAL ESTATE LLC

    2540 Hempel Cove Ct, Windermere, FL 34786
  • /87

    Starting at $2,095 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

    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 $812,351

    Last Listing Agent Natalie Rosario FATHOM REALTY FL LLC

    11660 Delwick Dr, Windermere, FL 34786
    • /2

      Est $1,518,673

      Not Listed For Sale

      8475 Eagles Loop Cir Unit 6, Windermere, FL 34786

      • 5 Beds
      • 5 Baths
      • 3,983 Sq Ft
      • Built 2004
      8475 Eagles Loop Cir Unit 6, Windermere, FL 34786

      Last Sold Summary

      • 81 Days On Market

      Last Listing Agent Emily Lewis LAKESIDE REALTY WINDERMERE INC

  • /44

    $455,000

    Open Sat 11AM - 1PM $35K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,091 Sq Ft

    13755 Bravante Aly, 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 13755 Bravante Aly, Windermere, FL 34786, a charming two story home featuring 3 bedrooms and 2 bathrooms located in a desirable Windermere community.This home offers a bright open floor plan with

    Agent Photo

    Thomas Nickley

    KELLER WILLIAMS REALTY AT THE PARKS

    13755 Bravante Aly, Windermere, FL 34786
  • /51

    Starting at $1,419 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

    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 $853,176

    Last Listing Agent Terrie Giles KELLER WILLIAMS CLASSIC

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

      Est $792,953

      Not Listed For Sale

      9447 Westover Club Cir, Windermere, FL 34786

      • 4 Beds
      • 3 Baths
      • 2,568 Sq Ft
      • Built 2001
      9447 Westover Club Cir, Windermere, FL 34786

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Erica Sadelfeld THE REAL ESTATE COLLECTION LLC

  • /39

    $1,085,000

    $35K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 4,625 Sq Ft

    13525 Gorgona Isle Dr, Windermere, FL 34786

    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 entertaining.A dramatic two-story foyer creates a

    Agent Photo

    Roo Klaers

    COLDWELL BANKER REALTY

    13525 Gorgona Isle Dr, Windermere, FL 34786
  • /117

    Starting at $1,725

    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 you'll find awe-inspiring day and night.

    Venetian Isle

    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 $852,374

    Last Listing Agent Shelley Dawson COMPASS FLORIDA LLC

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

      Est $848,754

      Not Listed For Sale

      6321 Clearmeadow Ct, Windermere, FL 34786

      • 4 Beds
      • 3 Baths
      • 2,560 Sq Ft
      • Built 2002
      6321 Clearmeadow Ct, Windermere, FL 34786

      Last Sold Summary

      • 64 Days On Market

      Last Listing Agent Kiran Khan KELLER WILLIAMS CLASSIC

  • /38

    $1,985,000

    $215K PRICE DROP Under Contract
    • 5 Beds
    • 5 Baths
    • 4,228 Sq Ft

    1118 Estancia Woods Loop, Windermere, FL 34786

    Under contract-accepting backup offers. A Masterpiece of Luxury Living in Windermere. Welcome to an extraordinary custom residence in the prestigious community of Estancia at Windermere, where timeless elegance meets modern luxury. Enhanced with over $400,000 in post-construction upgrades, this exceptional 2019 residence is a true showpiece. Offering more than 4,230 square feet of beautifully

    Agent Photo

    Andrew Kincaid

    BHHS FLORIDA REALTY

    1118 Estancia Woods Loop, Windermere, FL 34786
  • /25

    Starting at $1,653

    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

    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

    Current Estimated Value $852,950

    Last Listing Agent Judy Black UPSIDE REAL ESTATE INC

    299 W 4th Ave, Mount Dora, FL 32757
    • /2

      Est $677,313

      Not Listed For Sale

      9473 Palm Tree Dr, Windermere, FL 34786

      • 3 Beds
      • 2 Baths
      • 2,084 Sq Ft
      • Built 1986
      9473 Palm Tree Dr, Windermere, FL 34786

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Mike Long COLDWELL BANKER REALTY

  • /64

    $609,900

    $18K PRICE DROP Under Contract
    • 4 Beds
    • 3 Baths
    • 3,001 Sq Ft

    6601 Duncaster St, Windermere, FL 34786

    Under contract-accepting backup offers. PRICE IMPROVEMENT! MOTIVATED SELLER! ***NEW ROOF IS DONE.***Welcome to this spacious 4-bedroom, 3-bath Victorian-style home in the highly desirable Lakes of Windermere community. Boasting over 3,000 square feet of living space, this beautifully designed home offers an exceptional layout ideal for both everyday living and entertaining.A charming

    Agent Photo

    Wenyu Wang

    ANTS REALTY LLC

    6601 Duncaster St, Windermere, FL 34786
  • /43

    Starting at $1,525 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

    7826 Crosswater Trail, Windermere, FL 34786
  • /2

    $390,000

    Sold Jul 27, 2026

    11636 Water Run Aly, Windermere, FL 34786

    • 3 Beds
    • 2.5 Baths
    • 1,584 Sq Ft
    • Built 2017

    Last Sold Summary

    • 13% Below List Price
    • $246/SF
    • 253 Days On Market

    Current Estimated Value $395,313

    Last Listing Agent Jose Jimenez EXP REALTY LLC

    11636 Water Run Aly, Windermere, FL 34786
    • /2

      Est $893,008

      Not Listed For Sale

      1009 Algare Loop, Windermere, FL 34786

      • 4 Beds
      • 3 Baths
      • 2,608 Sq Ft
      • Built 2002
      1009 Algare Loop, Windermere, FL 34786

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Petra Bukalo PA FLORIDA REALTY INVESTMENTS

  • /66

    $424,000

    $1K PRICE DROP Under Contract
    • 3 Beds
    • 2.5 Baths
    • 1,700 Sq Ft

    7435 Ripplepointe Way, Windermere, FL 34786

    Under contract-accepting backup offers. Welcome home to Lake Burden, one of Windermere's most peaceful and welcoming neighborhoods. This beautifully maintained 3-bedroom, 2.5-bath townhouse — built in 2013 — is move-in ready, waiting for you with the BEST PRICE in the area!Start your mornings on the charming front porch, where you can sip your coffee and watch the neighborhood come to

    Agent Photo

    HERNY MENDEZ

    LPT REALTY, LLC

    7435 Ripplepointe Way, Windermere, FL 34786
  • /35

    Starting at $1,688 Per Month

    • 1 - 2 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

    11598 Lachlan Ln, Windermere, FL 34786
  • /2

    $464,000

    Sold Aug 17, 2026

    9017 Woodbreeze Blvd, Windermere, FL 34786

    • 3 Beds
    • 2 Baths
    • 1,723 Sq Ft
    • Built 1988

    Last Sold Summary

    • $269/SF
    • 0 Days On Market

    Current Estimated Value $554,554

    Last Listing Agent Manny del Valle KELLER WILLIAMS WINTER PARK

    9017 Woodbreeze Blvd, Windermere, FL 34786
    • /2

      Est $347,448

      Not Listed For Sale

      14241 Confetti Dr, Windermere, FL 34786

      • 2 Beds
      • 2 Baths
      • 1,155 Sq Ft
      • Built 2004
      14241 Confetti Dr, Windermere, FL 34786

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Lenise De Carvalho CORCORAN PREMIER REALTY

  • /54

    $689,000

    Open Sat 11AM - 1PM $60K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,594 Sq Ft

    13519 Bicton Ln, Windermere, FL 34786

    Welcome to Lakes of Windermere Peachtree, a sought-after gated community where luxury living meets unbeatable Central Florida convenience. This 4-bedroom, 3-bathroom home offers nearly 3,000 square feet of thoughtfully designed living space, a 3-car garage, and a brand-new roof and windows, giving buyers peace of mind and long-term value from day one.One of the most coveted features of

    Agent Photo

    Tiphany Weeks

    DIAMOND REAL ESTATE GROUP

    13519 Bicton Ln, Windermere, FL 34786
  • /13

    $3,595 Per Month

    • 4 Beds
    • 3.5 Baths
    • 3,089 Sq Ft
    • House for Rent

    14020 Eden Isle Blvd, 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 $3739.90. That covers your base rent, $3595.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    14020 Eden Isle Blvd, 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 $352,181

    Last Listing Agent Vanessa Lee COLDWELL BANKER REALTY

    6327 Southbridge St, Windermere, FL 34786
    • /2

      Est $373,525

      Not Listed For Sale

      5318 Kumquat Loop, Windermere, FL 34786

      • 3 Beds
      • 2.5 Baths
      • 1,461 Sq Ft
      • Built 2005
      5318 Kumquat Loop, Windermere, FL 34786

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Ronald Ziolkowski RE/MAX PRIME PROPERTIES

  • /65

    $1,395,000

    $155K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,399 Sq Ft

    12411 Montalcino Cir, Windermere, FL 34786

    SELLER MOTIVATED!!! A custom home in the desirable Casa del Lago community. The Spanish-style exterior and elegant, clean transitional interior will surely catch your attention. This home offers 4 beds, 4.5 baths, plus an office, 3,400 sq ft under air, a saltwater pool and spa, an outdoor kitchen, and a gas fireplace near the pool. This home is full of upgrades! Porcelain floors, exotic granite

    Agent Photo

    Mauro Costa

    WILLIAM RAVEIS FLORIDA, LLC

    12411 Montalcino Cir, Windermere, FL 34786
  • /20

    $2,499 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,668 Sq Ft
    • House for Rent

    8831 Herencia Aly, Windermere, FL 34786

    SPLIT THE PAYMENT! Reserve your new home by paying 50% of your security deposit now, with the remaining balance due before move-in.Welcome to 8831 Herencia Alley in Windermere, FL (34786)! This modern two-story townhome offers 3 bedrooms, 2.5 bathrooms, and 1,668 square feet of bright, open living space in the sought-after Legado community. The main level features an open-concept layout

    8831 Herencia Aly, 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 $762,734

    Last Listing Agent Hilary Hall COMPASS FLORIDA LLC

    13254 Penshurst Ln, Windermere, FL 34786
    • /2

      Est $555,616

      Not Listed For Sale

      6830 Mapperton Dr, Windermere, FL 34786

      • 3 Beds
      • 2.5 Baths
      • 2,230 Sq Ft
      • Built 2005
      6830 Mapperton Dr, Windermere, FL 34786

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Kristin Haughwout-Osorio PARKSIDE PROPERTIES, LLC

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$1,205,000
Median Single Family Sale Price
$1,450,000
Median Townhouse Sale Price
$429,000
Median 2 Bedroom Sale Price
$297,250
Average Price Per Sq Ft
$440
Number of Homes for Sale
139
Last 12 months Home Sales
354
Months of Supply
4.70
Median List Price
$1,499,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
-2%
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