16,405

Windermere, FL Homes

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  • /15

    $350,000

    • 3 Beds
    • 2 Baths
    • 1,455 Sq Ft

    11434 Jasper Kay Terrace Unit 306, Windermere, FL 34786

    Beautiful Lakeside at Lakes of Windermere condominium - Third floor corner unit with screened balcony. This unit features an open floor plan that combines kitchen, living room, and dining room. The kitchen feature 42 inch wood cabinets and a breakfast bar. Spacious primary bedroom. The A/C was replaced in October 2020. Tons of storage throughout the unit! The community features Clubhouse, Pool,

    Agent Photo

    Jay Stewart

    SOUTHERN REALTY GROUP LLC

    (689) 314-5683

    11434 Jasper Kay Terrace Unit 306, Windermere, FL 34786
  • /32

    $3,000 per month

    • 4 Beds
    • 2.5 Baths
    • 1,826 Sq Ft
    • Townhouse for Rent

    14017 Sparkling Cove Ln Unit GE, Windermere, FL 34786

    Welcome to this stunning 3-bedroom, 2.5-bathroom townhome located in the highly desirable Windermere community. Boasting 1,826 square feet of living space, this beautifully maintained home offers an open floor plan

    Agent Photo

    Elaine Garcia

    GARCIA REALTY GROUP

    (689) 252-6991

    14017 Sparkling Cove Ln Unit GE, Windermere, FL 34786
  • /2

    $905,000 Sold May 02, 2025

    • 2,346 Sq Ft
    • $386/SF
    • 20 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1986

    400 W 2nd Ave, Windermere, FL 34786

    Location, location! Nestled in a picturesque, park-like setting, this single-story home sits on a coveted corner lot in the heart of Old Windermere. Featuring a tile roof, wraparound screened porch, and an inviting outdoor stone firepit, this residence blends timeless charm with modern convenience.Inside, the home boasts wood and travertine floors, a striking brick fireplace, and gourmet kitchen

    Judy Black UPSIDE REAL ESTATE INC

    400 W 2nd Ave, Windermere, FL 34786
    • /30

      Est $930,474 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,690 Sq Ft

      8460 Elba Isle Ct, Windermere, FL 34786

      8460 Elba Isle Ct, Windermere, FL 34786
  • /25

    $545,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,342 Sq Ft

    5014 Wise Bird Dr, Windermere, FL 34786

    New roof!Check out our 3D Tour.Fabulous Summerport Home with cute front porch perfect for morning coffee!! Formal Living and Dining room with upgraded lighting. The dream kitchen features 42" maple cabinets with crown, granite counters, tile backsplash, breakfast bar, custom built-in seating, Gas range/cooktop for gourmet meals all overlooking the HUGE family room with built-in

    Agent Photo

    Hong Lu

    CHARLES RUTENBERG REALTY ORLANDO

    (407) 708-9675

    5014 Wise Bird Dr, Windermere, FL 34786
  • /86

    $1,685 - $4,250 per month

    Addison At Windermere

    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.

    13644 Tortona Ln, Windermere, FL 34786
  • /2

    $390,000 Sold May 02, 2025

    • 1,335 Sq Ft
    • $292/SF
    • 22 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2012

    7752 Rigby St, Windermere, FL 34786

    GREAT furnished 3-bedrooms, 2.5-baths townhome in the heart of Windermere! The home features a spacious, open kitchen complete with stainless steel appliances. Step outside to access a private courtyard that connects directly to a two car garage, providing both convenience and privacy. Upstairs, you’ll find three comfortable bedrooms and two full bathrooms. With its low maintenance exterior, the

    Daniela de Rodriguez B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE

    7752 Rigby St, Windermere, FL 34786
    • /37

      Est $1,605,716 Not Listed For Sale

      • 4 Beds
      • 4.5 Baths
      • 4,396 Sq Ft

      1214 Estancia Woods Loop, Windermere, FL 34786

      1214 Estancia Woods Loop, Windermere, FL 34786
  • /61

    $625,000

    • 4 Beds
    • 2 Baths
    • 2,063 Sq Ft

    9056 Woodbreeze Blvd, Windermere, FL 34786

    Welcome to 9056 Woodbreeze Blvd, a remarkable 4-bedroom, 2-bathroom home with a 2-car garage, nestled in the serene Silver Woods neighborhood of Windermere, FL. This exceptional residence offers a unique blend of privacy and community amenities. With only one adjacent neighbor and community tennis courts on the other side, the property provides a tranquil retreat. The backyard overlooks a

    Agent Photo

    Tom Langmann

    RE/MAX 200 REALTY

    (689) 305-3637

    9056 Woodbreeze Blvd, Windermere, FL 34786
  • /23

    $2,850 per month

    • 4 Beds
    • 2.5 Baths
    • 2,068 Sq Ft
    • House for Rent

    12030 Silverlake Park Dr, Windermere, FL 34786

    LOCATION, LOCATION, LOCATION. Beautiful 4/bed 2.5/bath townhouse in desirable Windermere Trails. Watch Disney fireworks nightly from spacious front porch! The home has tile and luxury vinyl throughout (NO CARPET) with plenty of room for families or individuals. Family room and dining room are downstairs along with a kitchen that features stainless steel appliances and granite counters. Master

    Carolyn Hunt SUNSHINE FLORIDA REALTY, INC

    12030 Silverlake Park Dr, Windermere, FL 34786
  • /2

    $1,240,000 Sold May 02, 2025

    • 5,149 Sq Ft
    • $241/SF
    • 40 Days On Market
    • 6 Beds
    • 6.5 Baths
    • Built 2014

    7587 Lake Albert Dr, Windermere, FL 34786

    One or more photo(s) has been virtually staged. **WELCOME HOME** Lake Burden South **POOL HOME** full of gorgeous upgrades that include a SUMMER KITCHEN complete with bar seating, TWO STORY LIVING ROOM with a must see coffered ceiling and tons of natural light, DUAL PRIMARY SUITES (one up and one down!), a chef’s GOURMET KITCHEN, dedicated OFFICE space and a second floor LOFT; plus complimentary

    Jennifer Wemert WEMERT GROUP REALTY LLC

    7587 Lake Albert Dr, Windermere, FL 34786
    • /43

      Est $1,005,689 Not Listed For Sale

      • 5 Beds
      • 4 Baths
      • 3,648 Sq Ft

      8414 Vivaro Isle Way, Windermere, FL 34786

      8414 Vivaro Isle Way, Windermere, FL 34786
  • /75

    $3,700,000

    • 6 Beds
    • 8 Baths
    • 6,930 Sq Ft

    13305 Bellaria Cir, Windermere, FL 34786

    In the gated Bellaria community, featuring six expansive bedrooms, including two primary suites and four en suites, this residence is the ideal blend of privacy and convenience, fully furnished. Enjoy your private cinema, this Toll Brothers estate blends luxury and comfort with dramatic ceilings, an open floor plan, and travertine marble flooring on main areas. The chef's kitchen features

    Agent Photo

    Alessandro Minato

    PREMIER SOTHEBYS INT'L REALTY

    (407) 565-9509

    13305 Bellaria Cir, Windermere, FL 34786
  • /38

    $1,545 - $2,460 per month

    Citra at Windermere

    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 Lake

    11353 Citra Cir, Windermere, FL 34786
  • /2

    $1,349,000 Sold May 02, 2025

    • 3,235 Sq Ft
    • $417/SF
    • 59 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 2012

    11748 Waterstone Loop Dr, Windermere, FL 34786

    Welcome to this stunning custom home, crafted by Silliman Homes, located within the 24HR GUARD-GATED community of Waterstone in Windermere, FL. Surrounded by multimillion-dollar homes, this 5-bedroom, 4-bathroom residence offers 3,235 square feet of luxurious living—your chance to own a slice of luxury. From the moment you arrive, the sleek Mediterranean design captures your attention. Step

    Immu Korvenmaa ALIGN REAL ESTATE LLC

    11748 Waterstone Loop Dr, Windermere, FL 34786
    • /80

      Est $2,476,808 Not Listed For Sale

      • 5 Beds
      • 7 Baths
      • 5,161 Sq Ft

      11628 Waterstone Loop Dr, Windermere, FL 34786

      11628 Waterstone Loop Dr, Windermere, FL 34786
  • /15

    $2,150,000

    • 1 Bed
    • 1 Bath
    • 1,124 Sq Ft

    10433 Trout Rd, Orlando, FL 32836

    Don't miss this amazing lakefront lot with 100 feet of frontage on LAKE TIBET, part of the sought-after Butler Chain of Lakes. With direct access to 12 connected lakes, this is a dream spot for boating, fishing, and water sports.Sitting right next to Butler - Tibet Preserve Park, this 3.31-acre property offers breathtaking views, privacy, serenity and tons of potential. There’s a small house

    Agent Photo

    Ursula Garcia Moraes

    PRISTINE INTERNATIONAL REALTY LLC

    (321) 386-6044

    10433 Trout Rd, Orlando, FL 32836
  • /23

    $2,349 per month

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

    13010 Langstaff Dr, Windermere, FL 34786

    Welcome to 13010 Langstaff Drive, a beautifully maintained 3-bedroom, 2.5-bath townhome nestled in one of Windermere’s most sought-after communities. This spacious home features dual master suites, modern finishes throughout, and a smart, functional layout perfect for comfortable living. The main level offers an open-concept living area, kitchen, and a convenient half bath. Upstairs, you’ll find

    Steve Simpson 407 PROPERTIES

    13010 Langstaff Dr, Windermere, FL 34786
  • /2

    $425,000 Sold May 01, 2025

    • 1,748 Sq Ft
    • $243/SF
    • 10 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2015

    Unlisted Address

    Charming Townhouse in Windermere SoundWelcome to this beautiful townhouse located in the desirable community of Windermere Sound! Built in 2015, this 3-bedroom, 2.5-bathroom home offers a modern and functional design with 1,733 sqft of living space.As you enter, you’ll be greeted by spacious rooms filled with natural light. The kitchen features elegant cabinetry, granite countertops, and

    Alexandra Mateu BAHIA INTERNATIONAL REALTY

    Unlisted Address
    • /40

      Est $816,598 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,988 Sq Ft

      9150 Outlook Rock Trail, Windermere, FL 34786

      9150 Outlook Rock Trail, Windermere, FL 34786
  • /16

    $2,150,000

    • Land
    • 3.31 Acres
    • $649,547 per Acre

    10433 Trout Rd, Orlando, FL 32836

    Don't miss this amazing lakefront lot with 100 feet of frontage on LAKE TIBET, part of the sought-after Butler Chain of Lakes. With direct access to 12 connected lakes, this is a dream spot for boating, fishing, and water sports. Sitting right next to Butler - Tibet Preserve Park, this 3.31-acre property offers breathtaking views and tons of potential. Build your dream home with a private gate or

    Agent Photo

    Ursula Garcia Moraes

    PRISTINE INTERNATIONAL REALTY LLC

    (321) 850-2122

    10433 Trout Rd, Orlando, FL 32836
  • /51

    $1,589 - $3,711 per month

    Talcott at Windermere

    1-3 Beds

    5820 Nature View Dr, Windermere, FL 34786

    The Retreat at Windermere Apartments offers you a haven to come home to. You enjoy inspired living in a community that is perfect for a variety of lifestyles. Choose a one, a two or a three bedroom apartment to experience a host of great features. All floor plans come with the choice of two distinct designer color palettes that blend beautifully with the stylish wood flooring and the lofty,

    5820 Nature View Dr, Windermere, FL 34786
  • /2

    $505,000 Sold Apr 30, 2025

    • 1,988 Sq Ft
    • $254/SF
    • 3 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2015

    7325 Ella Ln, Windermere, FL 34786

    Welcome to your dream retreat in one of Orlando’s most desirable neighborhoods! This adorable, cozy bungalow is bursting with charm and character, nestled in the highly sought-after community of Windermere. Featuring 3 bedrooms and 2.5 baths, this home is perfect for first-time buyers, downsizers, or anyone craving peaceful Florida living with a touch of elegance. Built in 2015, the residence

    Zuby Naeem LA ROSA REALTY ORLANDO LLC

    7325 Ella Ln, Windermere, FL 34786
    • /34

      Est $528,640 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,058 Sq Ft

      13335 Overstreet Rd, Windermere, FL 34786

      13335 Overstreet Rd, Windermere, FL 34786
  • /30

    $1,700,000

    • Land
    • 2.12 Acres
    • $801,887 per Acre

    10948 Down Park Ln, Windermere, FL 34786

    BUILD YOUR DREAM HOME in this incredibly rare vacant lot located in the highly sought after Town of Windermere! Zoned for single family residential and offering over 2.12 acres of land, this property is located on a lovely pond with 2 fountains and is in close proximity to the Butler Chain of Lakes offering the possibility for views of Lake Down which is situated incredibly close by! The private

    Agent Photo

    Andrew Kincaid

    BHHS FLORIDA REALTY

    (689) 314-5758

    10948 Down Park Ln, Windermere, FL 34786
  • /12

    $4,150 per month

    • 5 Beds
    • 3.5 Baths
    • 3,472 Sq Ft
    • House for Rent

    13272 Penshurst Ln, Windermere, FL 34786

    5 bedroom, 3 bath home nestled in the community of Windermere Sound. Located near schools, parks, shopping and more, this home is waiting for you! A Large house like this, is sure not to last long.

    Donny Hang Fung BLUEHOUSE REALTY GROUP LLC

    13272 Penshurst Ln, Windermere, FL 34786
  • /2

    $772,500 Sold Apr 30, 2025

    • 3,387 Sq Ft
    • $228/SF
    • 4 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 2004

    6232 Talaria Dr, Windermere, FL 34786

    Stunning 5 Bedroom Windermere Pool Home in Providence!Welcome Home to this Immaculately maintained 5-bedroom,4-bathroom home with a bonus room and 3 car garage, nestled in the highly sought-after Windermere community of Providence. Designed for both comfort and entertaining, this home features wood floors in formal areas, crown molding, and an open floor plan that seamlessly connects the main

    Matine Pawlicki CENTURY 21 CARIOTI

    6232 Talaria Dr, Windermere, FL 34786
    • /36

      Est $663,860 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,842 Sq Ft

      6526 Sawyer Shores Ln, Windermere, FL 34786

      6526 Sawyer Shores Ln, Windermere, FL 34786
  • /31

    $414,900

    • 3 Beds
    • 2.5 Baths
    • 1,479 Sq Ft

    7348 Yoder St, Windermere, FL 34786

    Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom townhome with a private courtyard and detached garage, nestled in the sought-after Lake Burden community of Windermere, Florida. Boasting high ceilings, rich wood flooring, and an expansive outdoor courtyard, this move-in-ready residence offers both comfort and style. Located in the heart of Windermere, you'll enjoy unbeatable access

    Agent Photo

    Carlos German

    EXP REALTY LLC

    (407) 606-8621

    7348 Yoder St, Windermere, FL 34786
  • /117

    $1,669 - $4,937 per month

    Venetian Isle

    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.

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

    $500,000 Sold Apr 30, 2025

    • 1,840 Sq Ft
    • $272/SF
    • 6 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2016

    8255 Bryce Canyon Ave, Windermere, FL 34786

    Immediately available, this 4-bedroom, 2.5-bathroom, two-story home is situated on a premium corner lot in the desirable Windermere Trails community.Upon arrival, you’ll be welcomed by an oversized front rocker porch, perfect for enjoying the neighborhood’s charm. Inside, the open-concept living room, dining room, and kitchen flow seamlessly over beautiful wood flooring. The spacious kitchen

    Juan Castro REDFIN CORPORATION

    8255 Bryce Canyon Ave, Windermere, FL 34786
    • /30

      Est $547,194 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,139 Sq Ft

      6442 Golden Dewdrop Trail, Windermere, FL 34786

      6442 Golden Dewdrop Trail, Windermere, FL 34786
  • /37

    $1,750,000

    • 5 Beds
    • 4 Baths
    • 4,026 Sq Ft

    2926 Marquesas Ct Unit 1, Windermere, FL 34786

    Back on the market due to buyer’s funding, no fault of the home. Great opportunity to own a lakefront home on Lake Crescent in one of Windermere’s most exclusive gated private ski lake communities, Lake Crescent Reserve. Located in the town limits of beautiful Windermere, this property sits on the highest elevated lot on 175-acre spring-fed Lake Crescent designated as an Outstanding Florida

    Agent Photo

    Kari Fleck

    THE REAL ESTATE COLLECTION LLC

    (407) 890-1110

    2926 Marquesas Ct Unit 1, Windermere, FL 34786
  • /21

    $2,950 per month

    • 4 Beds
    • 3.5 Baths
    • 1,761 Sq Ft
    • Townhouse for Rent

    14423 Bluebird Park Rd, Windermere, FL 34786

    Lovely 4/3.5 townhome in Summerport community of Windermere, FL. This spacious home features a 2 car garage, freshly painted interior, and brand new carpet in the bedrooms. The kitchen comes equipped with all appliances, and the bathrooms and kitchen are tiled for easy maintenance. Enjoy the convenience of a master bedroom on the first floor and spacious closets throughout. Step outside to relax

    Francisco Nieves-Taranto CT HOMES REALTY CORPORATION

    14423 Bluebird Park Rd, Windermere, FL 34786
  • /2

    $405,000 Sold Apr 30, 2025

    • 1,387 Sq Ft
    • $292/SF
    • 13 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2003

    6367 Merrick Landing Blvd, Windermere, FL 34786

    Nestled in the highly sought-after Merrick Landing at Summerport, this beautifully appointed corner townhome offers the perfect blend of comfort, convenience, and style. From the inviting covered front porch to the thoughtfully designed interior, this home is a true standout in the heart of Windermere. Step inside to discover an exceptional layout featuring three spacious bedrooms and three full

    Bobby Christiano COLDWELL BANKER RESIDENTIAL RE

    6367 Merrick Landing Blvd, Windermere, FL 34786
    • /22

      Est $1,051,262 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,117 Sq Ft

      12525 Montalcino Cir, Windermere, FL 34786

      12525 Montalcino Cir, Windermere, FL 34786
  • /28

    $1,450,000

    • Land
    • 2.91 Acres
    • $498,282 per Acre

    2938 Sunbittern Ct, Lake Butler, FL 34786

    Rare Opportunity – Exquisite and Expansive Lakefront Lot in Windermere!An extraordinary lakefront property in the prestigious, gated enclave of Lake Crescent Reserve at Butler Bay. This exclusive homesite offers unparalleled privacy, nestled between Lake Crescent and a tranquil lagoon, creating the sensation of a private island retreat. A long, winding driveway lined with mature magnolias leads

    Agent Photo

    Bobby Baldor

    EXP REALTY LLC

    (689) 315-0733

    2938 Sunbittern Ct, Lake Butler, FL 34786
  • /51

    $2,026 - $3,670 per month

    Arya at Windermere

    1-2 Beds

    1231 Arya Way, Ocoee, FL 34761

    Enjoy a vibrant lifestyle at Arya at Windermere, a 55+ community in Ocoee, FL offering unparalleled luxury amenities, including a massage room, steam room, outdoor putting green and a micro market. Arya features open concept 1 and 2-bedroom apartments with chef-inspired kitchens, granite countertops, stainless steel appliances, breakfast bar, wood-style plank floors, walk-in shower, washer and

    1231 Arya Way, Ocoee, FL 34761
  • /2

    $512,500 Sold Apr 30, 2025

    • 1,984 Sq Ft
    • $258/SF
    • 26 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2011

    6054 Roseate Spoonbill Dr, Windermere, FL 34786

    Charming, Energy-Efficient Home on an Oversized Lot in Windermere Landings.Discover the perfect blend of style, comfort, and efficiency in this beautifully maintained 3-bedroom, 2.5-bath home, ideally situated on an oversized lot in the highly desirable Windermere Landings community. Featuring a BRAND NEW AC and appliances, this home is move-in ready with modern upgrades for worry-free living.

    Aline Oliveira META ONE REALTY GROUP LLC

    6054 Roseate Spoonbill Dr, Windermere, FL 34786
    • /21

      Est $560,855 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,214 Sq Ft

      7831 Berkshire Oak Alley, Windermere, FL 34786

      7831 Berkshire Oak Alley, Windermere, FL 34786

Showing Results 1 - 40, Page 1 of 18

Home Trends in Windermere, FL

Home Trends

Median Price (12 Mo)
$902,500
Median Single Family Price
$1,131,350
Median Townhouse Price
$429,000
Median 2 Bedroom Price
$307,500
Average Price Per Sq Ft
$373
Number of Homes for Sale
145
Last 12 months Home Sales
366
Months of Supply
4.80
Median List Price
$990,995
Median Discount From 1st List Price
4%
Median Home Sale Price YoY Change
3%
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