16,483

Windermere, FL Homes

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  • /81

    $2,400,000

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,602 Sq Ft

    10129 Lone Tree Ln, Orlando, FL 32836

    Welcome to an exceptional lakefront opportunity on the highly sought-after Butler Chain of Lakes. A major recent value enhancement has transformed this property through a completed lot reconfiguration, adding approximately 14,500 square feet and creating a true 0.80-acre lakefront homesite with direct frontage on beautiful Lake Tibet.Nestled within the desirable Cypress Shores community, this

    Agent Photo

    Ursula Garcia Moraes

    PRISTINE INTERNATIONAL REALTY LLC

    10129 Lone Tree Ln, Orlando, FL 32836
  • /53

    $10,000 Per Month

    • 5 Beds
    • 4 Baths
    • 3,058 Sq Ft
    • House for Rent

    5927 Caymus Loop, Windermere, FL 34786

    Welcome to this exceptional 5Bed, 4Bath residence located in the highly desirable Keene’s Pointe community in Windermere. Situated on an oversized lot with beautiful views of the 14th fairway of the Jack Nicklaus Signature Golf Course, this home offers an impressive combination of space, comfort, and Florida living.The bright and spacious interior is filled with natural light and features

    Carla Renata Pereira Motta MS LAND & BUILDING LLC

    5927 Caymus Loop, Windermere, FL 34786
  • /2

    $670,000

    Sold Nov 14, 2025

    2015 Woody Dr, Windermere, FL 34786

    • 3 Beds
    • 2 Baths
    • 2,042 Sq Ft
    • Built 1978

    Last Sold Summary

    • 4% Below List Price
    • $328/SF
    • 28 Days On Market

    Current Estimated Value $682,535

    Last Listing Agent Darrell Nunnelley VINTAGE REALTY GROUP LLC

    2015 Woody Dr, Windermere, FL 34786
    • /2

      Est $651,040

      Not Listed For Sale

      13772 Ingelnook Dr, Windermere, FL 34786

      • 3 Beds
      • 2.5 Baths
      • 2,750 Sq Ft
      • Built 2013
      13772 Ingelnook Dr, Windermere, FL 34786

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

  • /61

    $2,950,000

    • 5 Beds
    • 4 Baths
    • 7,153 Sq Ft

    4301 Down Point Ln, Windermere, FL 34786

    Lakefront estate on Lake Down in the Butler Chain of Lakes with over 150 feet of frontage and no HOA in Sunset Bay. Built in 1983, this 5 bedroom, 4 bath pool home offers nearly 7,000 square feet across three levels and presents a rare opportunity to renovate a true chain-of-lakes property to your own style and standards. Home retains much of its original character and is priced accordingly,

    Agent Photo

    Yuliya Mariani

    MARIANI REALTY GROUP

    4301 Down Point Ln, Windermere, FL 34786
  • /11

    $1,550 Per Month

    • 1 Bed
    • 1 Bath
    • 550 Sq Ft
    • House for Rent

    14222 Sonco Ave, Windermere, FL 34786

    Minimum Deposit $1550. Monthly Rent $1550! Available September 10th!Contact Polina at or at to schedule an appointment to view the apartment! *Showings are not confirmed until you speak directly with the Property Manager and a mutually agreed upon showing day/time has been establishedDiscover this charming garage apartment in desirable Windermere! ? Featuring stylish finishes

    14222 Sonco Ave, Windermere, FL 34786
  • /2

    $680,000

    Sold Feb 20, 2026

    4825 Palm Tree Ct, Windermere, FL 34786

    • 4 Beds
    • 2.5 Baths
    • 2,100 Sq Ft
    • Built 1985

    Last Sold Summary

    • $324/SF
    • 9 Days On Market

    Current Estimated Value $684,998

    Last Listing Agent Alex Vastardis COLDWELL BANKER REALTY

    4825 Palm Tree Ct, Windermere, FL 34786
    • /2

      Est $877,385

      Not Listed For Sale

      8243 Procida Isle Ln, Windermere, FL 34786

      • 5 Beds
      • 4 Baths
      • 3,226 Sq Ft
      • Built 2018
      8243 Procida Isle Ln, Windermere, FL 34786

      Last Sold Summary

      • 81 Days On Market

      Last Listing Agent Kwaku Mitchell REAL BROKER, LLC

  • /80

    $2,650,000

    Under Contract
    • 5 Beds
    • 5.5 Baths
    • 5,433 Sq Ft

    1408 Lake Whitney Dr, Windermere, FL 34786

    Under contract-accepting backup offers. Presenting this stunning LAKEFRONT RESIDENCE showcasing spectacular PANORAMIC VIEWS and ideally located within the premier GUARD GATED COMMUNITY of Reserve at Belmere in WINDERMERE. The property is approached by a circular driveway with centerpiece WATER FOUNTAIN set in mature landscaping alongside an adjoining 3 car garage with side entry. Upon arrival, an

    Agent Photo

    Alice Anne Jackson

    CORCORAN PREMIER REALTY

    1408 Lake Whitney Dr, Windermere, FL 34786
  • /44

    $2,950 Per Month

    • 4 Beds
    • 2 Baths
    • 2,300 Sq Ft
    • House for Rent

    12947 Runswick Ave, Windermere, FL 34786

    MOVE-IN READY! Beautiful and spacious 4-bedroom, 2-bath home located in the highly desirable Lakes of Windermere community. Surrounded by mature landscaping, scenic lakes, walking trails, and top-rated schools, this home even offers the opportunity to enjoy Disney fireworks just steps from your front door.This well-designed single-story home features luxury vinyl plank and tile flooring

    Cui Li RATIO REAL ESTATE, LLC

    12947 Runswick Ave, Windermere, FL 34786
  • /2

    $550,000

    Sold Sep 30, 2025

    5238 Beach River Rd, Windermere, FL 34786

    • 4 Beds
    • 3 Baths
    • 2,414 Sq Ft
    • Built 2004

    Last Sold Summary

    • $228/SF
    • 3 Days On Market

    Current Estimated Value $558,183

    Last Listing Agent Liza Farzati SERHANT

    5238 Beach River Rd, Windermere, FL 34786
    • /62

      Est $2,391,499

      Not Listed For Sale

      13334 Bellaria Cir, Windermere, FL 34786

      • 5 Beds
      • 7 Baths
      • 5,734 Sq Ft
      • Built 2014
      13334 Bellaria Cir, Windermere, FL 34786

      Last Sold Summary

      • 189 Days On Market

      Last Listing Agent María Gabriela Lara CENTURY 21 CARIOTI

  • /23

    $3,189,000

    • 4 Beds
    • 4.5 Baths
    • 3,365 Sq Ft

    5050 Isleworth Country Club Dr, Windermere, FL 34786

    Positioned along the 6th fairway of Isleworth Golf & Country Club, this thoughtfully updated single-story residence offers a rare combination of privacy, golf-course views and effortless everyday living. A welcoming circular drive and mature oaks set the stage, while inside, nearly 3,400 square feet unfolds in a light-filled collection of spaces designed to feel equally comfortable for quiet

    Agent Photo

    Toni Marie Cafferty

    COMPASS FLORIDA LLC

    5050 Isleworth Country Club Dr, Windermere, FL 34786
  • /10

    $2,399 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,446 Sq Ft
    • Townhouse for Rent

    8259 Maritime Flag St, Windermere, FL 34786

    Beautiful new villa,Stain Still appliances, Granite Countertops, Ceramic Tile in the 1st Floor, 3 bedrooms, 2 1/2 bathrooms, great location!! Driving Directions: Community is on the corner of 535 and Reams Rd.

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

    $620,000

    Sold Apr 24, 2026

    6846 Helmsley Cir, Windermere, FL 34786

    • 5 Beds
    • 3 Baths
    • 2,555 Sq Ft
    • Built 2009

    Last Sold Summary

    • 11% Below List Price
    • $243/SF
    • 154 Days On Market

    Current Estimated Value $616,705

    Last Listing Agent Nickolas Amburgey COMPASS FLORIDA LLC

    6846 Helmsley Cir, Windermere, FL 34786
    • /80

      Est $2,581,380

      Not Listed For Sale

      11628 Waterstone Loop Dr, Windermere, FL 34786

      • 5 Beds
      • 7 Baths
      • 5,161 Sq Ft
      • Built 2015
      11628 Waterstone Loop Dr, Windermere, FL 34786

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Patricia Mascarenhas Bonina Zimath CHARLES RUTENBERG REALTY ORLANDO

  • /46

    $975,000

    $225K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,618 Sq Ft

    3629 Lake Buynak Rd, Windermere, FL 34786

    Now offered at an exceptional value, this 1.3-acre property in Lake Buynak Estates presents a rare opportunity to enjoy acreage, privacy and flexibility in one of Central Florida's most desirable locations. Located within the highly sought-after Windermere ZIP code, this 4-bedroom, 3.5-bath residence offers more than 2,600 square feet of living space with a thoughtfully designed split floor plan,

    Agent Photo

    Tania Matthews

    KELLER WILLIAMS ELITE PARTNERS III REALTY

    3629 Lake Buynak Rd, Windermere, FL 34786
  • /25

    $3,750 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,682 Sq Ft
    • House for Rent

    13633 Riggs Way, Windermere, FL 34786

    Get ready to spread out! This impressive 4-bedroom, 3.5-bathroom, two-story Windermere home offers the space, flexibility, and features that are hard to find in a rental. With two en-suite bedrooms, formal living and dining areas, a separate family room, and a 2-car garage, there's plenty of room to create spaces for relaxing, entertaining, working from home, or hosting guests.At the

    David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

    13633 Riggs Way, Windermere, FL 34786
  • /2

    $1,318,000

    Sold May 01, 2026

    1625 Down Lake Dr, Windermere, FL 34786

    • 5 Beds
    • 5.5 Baths
    • 3,383 Sq Ft
    • Built 1984

    Last Sold Summary

    • 6% Below List Price
    • $390/SF
    • 48 Days On Market

    Current Estimated Value $1,313,513

    Last Listing Agent Cindy Rosenbloom THE ROSENBLOOM TEAM

    1625 Down Lake Dr, Windermere, FL 34786
    • /2

      Est $788,788

      Not Listed For Sale

      6926 Trellis Vine Loop, Windermere, FL 34786

      • 5 Beds
      • 4.5 Baths
      • 3,124 Sq Ft
      • Built 2018
      6926 Trellis Vine Loop, Windermere, FL 34786

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent DENILEY VALDES TALENT REALTY SOLUTIONS

  • /42

    $989,990

    New Construction Open Sat 1PM - 4PM $125K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 3,153 Sq Ft

    14371 Crest Palm Ave, Windermere, FL 34786

    One or more photo(s) has been virtually staged. Arlington Floorplan – 3153 Sq. Ft. | 4 Beds | 4Baths | 2.5-Car Garage | Move-In ReadyWelcome to the Arlington with Bonus – a thoughtfully designed, 2-story home that perfectly blends luxury, functionality, and comfort. This brand new 3,140 square foot residence sits on an wooded lot, offering expansive indoor and outdoor living space, ready for

    Agent Photo

    Cindy Sapp

    OLYMPUS EXECUTIVE REALTY INC

    14371 Crest Palm Ave, Windermere, FL 34786
  • /47

    $2,900 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,091 Sq Ft
    • Spacious 3-Bed, 2.5 Bath End Unit Townhome in Windermere with 2 Car Garage!

    13701 Beckman Dr, Windermere, FL 34786

    This 3 bedroom, 2.5 bathroom single family townhome with a 2 car garage awaits it's next tenants! Arriving at this end-unit townhome you are greeted by lush and manicured greenery, beautiful street trees and sidewalk paths. As you enter, there's a charming accent wall and stairs leading to the primary bedroom suite and 2 additional guest bedrooms and full bath. The primary suite features a

    13701 Beckman Dr, Windermere, FL 34786
  • /2

    $2,404,000

    Sold Jan 15, 2026

    1724 Windermeredown Place, Windermere, FL 34786

    • 6 Beds
    • 6.5 Baths
    • 6,000 Sq Ft
    • Built 1995

    Last Sold Summary

    • 4% Below List Price
    • $401/SF
    • 46 Days On Market

    Current Estimated Value $2,378,693

    Last Listing Agent Chad Going SERHANT

    1724 Windermeredown Place, Windermere, FL 34786
    • /31

      Est $380,437

      Not Listed For Sale

      14237 Desert Haven St, Windermere, FL 34786

      • 3 Beds
      • 3.5 Baths
      • 1,861 Sq Ft
      • Built 2012
      14237 Desert Haven St, Windermere, FL 34786

      Last Sold Summary

      • 71 Days On Market

      Last Listing Agent Pam Eddy COLDWELL BANKER HUBBARD HANSEN

  • /13

    $1,158,990

    New Construction
    • 5 Beds
    • 4.5 Baths
    • 3,542 Sq Ft

    Duval Plan at Lake Cawood Cove - Traditional, Windermere, FL 34786

    The Duval is a two‐story home offering five bedrooms, four full bathrooms, one half bathroom, and a two‐car garage. A bright kitchen with breakfast nook anchors the open main floor, while a second‐floor loft overlooks the family room below. The private second‐floor primary suite, optional butler’s pantry, and centrally located laundry room add convenience and luxury to this spacious plan.

    Ashton Woods Builder
    5432 Winter Garden Vineland Rd Unit 37932788, Windermere, FL 34786
  • /13

    $2,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,450 Sq Ft
    • Townhouse for Rent

    12752 S Lake Sawyer Ln, Windermere, FL 34786

    3/2 "garage apartment" across from Windermere Prep. Partially furnished, garage and driveway parking. ALL utilities + WiFi included! ALL appliances included! Available Monthly or 12 Month term. Master lease required, subletting considered for qualified tenants. Approx $1,020 each room (3 available) depending on lease term.

    Chika Haines SAND DOLLAR REALTY GROUP INC

    12752 S Lake Sawyer Ln, Windermere, FL 34786
  • /2

    $718,000

    Sold Oct 20, 2025

    12755 Westside Village Loop, Windermere, FL 34786

    • 4 Beds
    • 3.5 Baths
    • 3,064 Sq Ft
    • Built 2018

    Last Sold Summary

    • 12% Below List Price
    • $234/SF
    • 142 Days On Market

    Current Estimated Value $729,915

    Last Listing Agent Eric Jia NUMBER 1 BROKER, LLC

    12755 Westside Village Loop, Windermere, FL 34786
    • /2

      Est $1,305,827

      Not Listed For Sale

      17550 Black Rail St, Windermere, FL 34786

      • 5 Beds
      • 4 Baths
      • 4,908 Sq Ft
      • Built 2015
      17550 Black Rail St, Windermere, FL 34786

      Last Sold Summary

      • 44 Days On Market

      Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

  • /100

    $7,500,000

    Under Contract
    • 6 Beds
    • 7.5 Baths
    • 6,874 Sq Ft

    724 W 2nd Ave, Windermere, FL 34786

    Under contract-accepting backup offers. Welcome to an extraordinary lakefront estate on the prestigious shores of Lake Butler with 182 feet of water frontage, where timeless architecture, exceptional craftsmanship, and resort-style amenities come together in one of Windermere's most coveted locations. Built in 2024 and spanning approximately 6,900 square feet under air (10,400 total square feet),

    Simon Simaan THE SIMON SIMAAN GROUP

    724 W 2nd Ave, Windermere, FL 34786
  • /39

    $3,075 Per Month

    • 4 Beds
    • 3 Baths
    • 2,411 Sq Ft
    • House for Rent

    4468 Blue Major Dr, Windermere, FL 34786

    AVAILABLE NOW! Spacious 4-bedroom, 3-bath home in Windermere, located across from a neighborhood playground on a premium private lot with water views from the living room, kitchen, master bedroom, and bath. This single-story home features tile throughout the main living areas, Corian countertops, a large kitchen with 42" wood cabinetry, black appliances, a gas range, washer and dryer included,

    4468 Blue Major Dr, Windermere, FL 34786
  • /2

    $825,000

    Sold Feb 11, 2026

    1735 Maple Leaf Dr, Windermere, FL 34786

    • 4 Beds
    • 2.5 Baths
    • 2,771 Sq Ft
    • Built 1989

    Last Sold Summary

    • 3% Below List Price
    • $298/SF
    • 3 Days On Market

    Current Estimated Value $861,837

    Last Listing Agent Frank Del Toro REVEL REALTY LLC

    1735 Maple Leaf Dr, Windermere, FL 34786
    • /34

      Est $510,380

      Not Listed For Sale

      13335 Overstreet Rd, Windermere, FL 34786

      • 3 Beds
      • 2 Baths
      • 2,058 Sq Ft
      • Built 2013
      13335 Overstreet Rd, Windermere, FL 34786

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Ryan Langley FLORIDA REALTY INVESTMENTS

  • /75

    $875,000

    $25K PRICE DROP
    • 6 Beds
    • 4 Baths
    • 4,176 Sq Ft

    8278 Procida Isle Ln, Windermere, FL 34786

    Watch Disney firework everyday from front porch. NO Carpet in the house. Stunning house in Windermere Isle in Gas community, Fully Fenced, 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

    Li Xue AGENT GROUP REALTY

    8278 Procida Isle Ln, Windermere, FL 34786
  • /20

    $4,800 Per Month

    • 4 Beds
    • 3 Baths
    • 2,484 Sq Ft
    • House for Rent

    8794 Crescendo Ave, Windermere, FL 34786

    Stunning 4-bedroom, 3-full-bath home with a private pool in the highly sought-after Windermere Trails community! Built in 2016, this spacious home offers approximately 2,484 SF of beautifully designed living space with an open-concept floor plan, abundant natural light, and modern finishes throughout.The gourmet kitchen features quartz countertops, stainless steel appliances, ample cabinetry,

    Alessandra Oliveira FLORIDA CONNEXION PROPERTIES

    8794 Crescendo Ave, Windermere, FL 34786
  • /2

    $1,500,000

    Sold Apr 29, 2026

    11821 Waterstone Loop Dr, Windermere, FL 34786

    • 4 Beds
    • 4.5 Baths
    • 3,447 Sq Ft
    • Built 2012

    Last Sold Summary

    • 3% Below List Price
    • $435/SF
    • 7 Days On Market

    Current Estimated Value $1,498,480

    Last Listing Agent Mauricio Penha VOLKE REAL ESTATE LLC

    11821 Waterstone Loop Dr, Windermere, FL 34786
    • /2

      Est $438,629

      Not Listed For Sale

      7629 Ripplepointe Way, Windermere, FL 34786

      • 3 Beds
      • 2.5 Baths
      • 1,881 Sq Ft
      • Built 2015
      7629 Ripplepointe Way, Windermere, FL 34786

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Kris Ibrahim HOME WISE REALTY GROUP, INC.

  • /53

    $3,600 Per Month

    • 4 Beds
    • 3 Baths
    • 2,826 Sq Ft
    • House for Rent

    13448 Zori Ln, Windermere, FL 34786

    FOR RENT OCTOBER 2026 | Luxury 4-Bedroom Home with Private In-Law Suite in Windermere Welcome to this beautifully updated 4-bedroom, 3-bathroom residence offering 2,826 square feet of elegant living space in one of Windermere's most desirable communities. This exceptional two-story home has been thoughtfully upgraded with a brand-new roof, New HVAC systems, Tile flooring, and an open kitchen,

    13448 Zori Ln, Windermere, FL 34786
  • /2

    $535,000

    Sold Jun 18, 2026

    11486 Misty Oak Aly, Windermere, FL 34786

    • 3 Beds
    • 2.5 Baths
    • 1,950 Sq Ft
    • Built 2016

    Last Sold Summary

    • 3% Below List Price
    • $274/SF
    • 24 Days On Market

    Current Estimated Value $539,876

    Last Listing Agent Kikuko Moribe CENTURY 21 CARIOTI

    11486 Misty Oak Aly, Windermere, FL 34786
    • /2

      Est $477,486

      Not Listed For Sale

      12691 Calderdale Ave, Windermere, FL 34786

      • 3 Beds
      • 2 Baths
      • 1,742 Sq Ft
      • Built 2012
      12691 Calderdale Ave, Windermere, FL 34786

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

Showing Results 81 - 120, Page 3 of 18

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