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Recently Sold Windermere Homes

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  • 1265 Estancia Woods Loop, Windermere, FL 34786
    1265 Estancia Woods Loop, Windermere, FL 34786
    /2

    $1,289,000 Sold Jul 28, 2025

    • 3,314 Sq Ft
    • $389/SF
    • 11 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2018

    1265 Estancia Woods Loop, Windermere, FL 34786

    Located in the prestigious town of Windermere, this exceptional Cannes floor plan offers an unparalleled blend of luxury, efficiency, and outdoor living. Situated on one of the largest lots in the community, this 4-bedroom, 3.5-bathroom residence showcases an expansive backyard oasis featuring a saltwater pool—heated by an energy-efficient heat pump—and a fully equipped summer kitchen, ideal for

    Matt Tomaszewski CORCORAN PREMIER REALTY

    1265 Estancia Woods Loop, Windermere, FL 34786
  • 729 Main St, Windermere, FL 34786
    729 Main St, Windermere, FL 34786
    /2

    $2,065,000 Sold Jul 14, 2025

    • 3,950 Sq Ft
    • $523/SF
    • 208 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 2015

    729 Main St, Windermere, FL 34786

    This custom home is truly a gem, blending luxury, craftsmanship, and the charm of small-town Windermere living. The attention to detail in every feature—from the stunning architectural design to the thoughtfully designed interiors—is remarkable. With its premium corner lot location, this home is not only a private oasis but also perfectly situated to take advantage of the vibrant and

    Billinda Boldt COLDWELL BANKER RESIDENTIAL RE

    729 Main St, Windermere, FL 34786
  • 11335 Winston Willow Ct, Windermere, FL 34786
    11335 Winston Willow Ct, Windermere, FL 34786
    /2

    $1,175,000 Sold Jul 10, 2025

    • 2,885 Sq Ft
    • $407/SF
    • 10 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1990

    11335 Winston Willow Ct, Windermere, FL 34786

    This RARE BEAUTY is a dream come true, 11335 Winston Willow Court is ready for you! Located in Willows at Lake Rhea, you will fall in love with this majestic neighborhood. Appreciate the beautiful curb appeal the moment you pull up to your new home, which is located at the end of a cul-de-sac, surrounded by magnificent trees, where you will instantly feel at peace. This 2-story custom pool home

    Valerie Winch REALTY HUB

    11335 Winston Willow Ct, Windermere, FL 34786
  • 2538 Carter Grove Cir, Windermere, FL 34786
    2538 Carter Grove Cir, Windermere, FL 34786
    /2

    $835,000 Sold Jul 03, 2025

    • 2,523 Sq Ft
    • $331/SF
    • 8 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1996

    2538 Carter Grove Cir, Windermere, FL 34786

    **WINDERMERE DREAM HOME ALERT -- MANORS AT BUTLER BAY** **OVER 1/2 ACRE LOT** **DEEDED BUTLER CHAIN OF LAKES RAMP & ACCESS** **PRIVATE POOL & SPA** **FOUR BEDROOMS + THREE FULL BATHS + OFFICE SPACE -- ALL ON ONE LEVEL** **WOOD FLOORING** **LOW HOA** Welcome to your Windermere Dream Home...located in the highly desired (and rarely available!) quaint community of THE MANORS at Butler Bay.

    Tara Moore TARA MOORE REAL ESTATE

    2538 Carter Grove Cir, Windermere, FL 34786
  • 10845 Bayshore Dr, Windermere, FL 34786
    10845 Bayshore Dr, Windermere, FL 34786
    /2

    $3,975,000 Sold Jul 02, 2025

    • 4,665 Sq Ft
    • $852/SF
    • 5 Days On Market
    • 4 Beds
    • 5 Baths
    • Built 2013

    10845 Bayshore Dr, Windermere, FL 34786

    Over 150 feet on Lake Down provides panoramic views of what is arguably the cleanest of the Pristine Butler Chain of Lakes with a white sand beach and crystal clear water it will be like having your own resort in the backyard..Bayshore Drive is a rare and exclusive peninsula with grand oaks lining the paved road providing that “Old Florida” feel - plenty of shade for the perfect place to exercise

    Darrell Nunnelley VINTAGE REALTY GROUP LLC

    10845 Bayshore Dr, Windermere, FL 34786
  • 10988 Down Park Ln, Windermere, FL 34786
    10988 Down Park Ln, Windermere, FL 34786
    /2

    $1,685,250 Sold Jun 25, 2025

    • Land
    • 6 Acres
    • $303,649 per Acre
    • 214 Days On Market

    10988 Down Park Ln, Windermere, FL 34786

    Prime Residential Vacant Land on Lake Down, Windermere, Florida. Nestled in the desirable enclave of Windermere, Florida, awaits a rareopportunity to claim your slice of paradise. Presenting a newly, unanimously approved by the Town of Windermere, lakefront lot of residentialvacant land spanning a generous 5.55 acres, this property boasts unparalleled potential for crafting your dream

    Alexis Anderson REGENCY REAL ESTATE LLC

    10988 Down Park Ln, Windermere, FL 34786
  • 2140 Lilypad Ln, Windermere, FL 34786
    2140 Lilypad Ln, Windermere, FL 34786
    /2

    $1,020,000 Sold Jun 23, 2025

    • 3,372 Sq Ft
    • $302/SF
    • 19 Days On Market
    • 5 Beds
    • 5 Baths
    • Built 1990

    2140 Lilypad Ln, Windermere, FL 34786

    Welcome to 2140 Lilypad Lane, a rare opportunity to own an impeccably maintained, estate home in the Willows at Lake Rhea. Nestled in a private cul-de-sac on over half an acre, this single-story home offers space and privacy. With over 3,300 square feet, this home features 5 bedrooms, 3 full bathrooms, 2 half bathroom, a large bonus room, and a private screened-in pool. As you step through the

    Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

    2140 Lilypad Ln, Windermere, FL 34786
  • 116 Main St, Windermere, FL 34786
    116 Main St, Windermere, FL 34786
    /2

    $695,000 Sold Jun 13, 2025

    • 1,269 Sq Ft
    • $548/SF
    • 91 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1958

    116 Main St, Windermere, FL 34786

    Welcome to a rare opportunity in the heart of Windermere! Located at 116 Main Street, this property represents one of the most coveted locations in Central Florida's premier community. Situated on Main Street, this lot offers the perfect canvas for your dream home in a location that simply cannot be replicated.While the existing structure requires extensive updating, the true value lies in this

    Adam Judd METROPOLIS R.E. SOLUTIONS, LLC

    116 Main St, Windermere, FL 34786
  • 2138 Kane Park Way, Windermere, FL 34786
    2138 Kane Park Way, Windermere, FL 34786
    /2

    $1,085,000 Sold Jun 02, 2025

    • 3,210 Sq Ft
    • $338/SF
    • 43 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1993

    2138 Kane Park Way, Windermere, FL 34786

    Nestled in the heart of The Willows at Lake Rhea, this breathtaking 5-bedroom, 3.5-bath POOL home sits on a spacious .60-Acre Cul-De-Sac lot, offering both privacy (green area across the street) and a serene pond view. From the moment you walk through the LEADED GLASS DOUBLE FRONT DOORS, you're greeted with A MASIVE WINDOW That Frames the Sparkling SOLAR-HEATED Pool, GAS-HEATED POOL SPA,

    Adam Eisen PLATINUM REALTY GROUP FLORIDA INC

    2138 Kane Park Way, Windermere, FL 34786
  • 98 E 10th Ave, Windermere, FL 34786
    98 E 10th Ave, Windermere, FL 34786
    /2

    $1,850,000 Sold May 30, 2025

    • 3,650 Sq Ft
    • $507/SF
    • 175 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2024

    98 E 10th Ave, Windermere, FL 34786

    Stunning, thoughtfully designed, contemporary pool home, NEW (completed in 2024). Bright, open floor plan boasting 4 spacious bedrooms, two with en-suite bathrooms, and an office or 5th bedroom. Step through the impressive cast iron/glass front door into the spacious foyer and the home opens up in front of you revealing upgrades galore. Features include: Built in floating media walls and

    Sue Webb WATSON REALTY CORP.

    98 E 10th Ave, Windermere, FL 34786
  • 11440 Willow Gardens Dr, Windermere, FL 34786
    11440 Willow Gardens Dr, Windermere, FL 34786
    /2

    $1,360,000 Sold May 22, 2025

    • 3,690 Sq Ft
    • $369/SF
    • 3 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1994

    11440 Willow Gardens Dr, Windermere, FL 34786

    Sunset Pond Views • Extensive Renovations • Premier Windermere Location • Set on a beautifully landscaped half-acre lot, this home offers conservation and water views in the sought-after community of Willows at Lake Rhea. A double-height foyer with mahogany doors and sightlines to the screened pool and spa creates an immediate sense of openness. The redesigned kitchen features rich cabinetry,

    Renee Funk EXP REALTY LLC

    11440 Willow Gardens Dr, Windermere, FL 34786
  • 2844 Marquesas Ct, Windermere, FL 34786
    2844 Marquesas Ct, Windermere, FL 34786
    /2

    $3,315,000 Sold May 16, 2025

    • 5,365 Sq Ft
    • $618/SF
    • 4 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1985

    2844 Marquesas Ct, Windermere, FL 34786

    Your Own Private Paradise – Just Under 6,000 Sq Ft of Lakefront LuxuryWelcome to your private sanctuary with both sunrise and sunset views over the shimmering waters of Lake Crescent. Located in the exclusive gated community of Lake Crescent Reserve, this lakefront masterpiece boasts just under 6,000 square feet of completely reimagined luxury living.Situated on a pristine, oversized lot

    Dianna Desboyaux SOUTHERN REALTY GROUP LLC

    2844 Marquesas Ct, Windermere, FL 34786
  • 11359 Willow Gardens Dr, Windermere, FL 34786
    11359 Willow Gardens Dr, Windermere, FL 34786
    /2

    $1,075,000 Sold May 16, 2025

    • 2,968 Sq Ft
    • $362/SF
    • 45 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1990

    11359 Willow Gardens Dr, Windermere, FL 34786

    | Brand New Architectural Roof as of March 2025 | You've been scouring all of the websites for months now, waiting for just that right home, with the perfect amount of space, updates; and an exceptionally well established neighborhood.....and you'll be glad that you waited! 11359 Willow Gardens Dr, in one of the most desirable communities in Windermere, offers everything that you could possibly

    Steven Horner RE/MAX PRIME PROPERTIES

    11359 Willow Gardens Dr, Windermere, FL 34786
  • 400 W 2nd Ave, Windermere, FL 34786
    400 W 2nd Ave, 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
  • 904 Main St, Windermere, FL 34786
    904 Main St, Windermere, FL 34786
    /2

    $3,650,000 Sold Apr 30, 2025

    • 6,079 Sq Ft
    • $600/SF
    • 195 Days On Market
    • 4 Beds
    • 6 Baths
    • Built 2003

    904 Main St, Windermere, FL 34786

    This property includes an Incredibly Rare Air Conditioned Boathouse that is completely renovated with Apartment, Kitchen and Bathroom. A Custom Platform Boat Lift with overhead garage door lends security and privacy that other boathouses do not offer.......................Owner is willing to renovate the pool deck to remove the flagstone and replace with a smooth finish travertine of your color

    Darrell Nunnelley VINTAGE REALTY GROUP LLC

    904 Main St, Windermere, FL 34786
  • 2026 Willow Lauren Ln, Windermere, FL 34786
    2026 Willow Lauren Ln, Windermere, FL 34786
    /2

    $1,130,000 Sold Apr 29, 2025

    • 3,419 Sq Ft
    • $331/SF
    • 40 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 1994

    2026 Willow Lauren Ln, Windermere, FL 34786

    LUXURIOUS 1ST FLOOR LIVING, plus BONUS ROOM on a tree shaded, 2/3 Acre lot situated on a Dead-End street in the highly desirable "Willows of Lake Rhea" community. 5 Bedroom, 4 Bath EXECUTIVE POOL (with upgraded PebbleTec finish) Home has HIGH-END FINISHES including HARDWOOD FLOORS, Rounded Corners, 12’ CEILINGS, Crown Molding, Plantation Shutters. Chef's Kitchen has BOTH an island with Sink,

    Adam Eisen PLATINUM REALTY GROUP FLORIDA INC

    2026 Willow Lauren Ln, Windermere, FL 34786
  • 2544 Carter Grove Cir, Windermere, FL 34786
    2544 Carter Grove Cir, Windermere, FL 34786
    /2

    $860,000 Sold Apr 28, 2025

    • 2,802 Sq Ft
    • $307/SF
    • 4 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1997

    2544 Carter Grove Cir, Windermere, FL 34786

    Nestled in the prestigious Manors at Lake Butler, this custom home on over half an acre offers an unparalleled living experience. As you drive through the serene canopy of majestic oaks, the stunning curb appeal and expansive driveway welcome you. The massive backyard provides ample space for relaxation and entertainment.Step inside to discover elegant formal living and dining areas, where

    Ronald Ziolkowski RE/MAX PRIME PROPERTIES

    2544 Carter Grove Cir, Windermere, FL 34786
  • 105 Pine St, Windermere, FL 34786
    105 Pine St, Windermere, FL 34786
    /2

    $2,285,000 Sold Apr 25, 2025

    • 5,696 Sq Ft
    • $401/SF
    • 47 Days On Market
    • 5 Beds
    • 5.5 Baths
    • Built 2015

    105 Pine St, Windermere, FL 34786

    One or more photo(s) has been virtually staged. On a serene over half acre lot in the heart of historic downtown Windermere this fabulous one-of-a kind multi-generational home is a short distance from the charming boutiques, eateries, coffee shops, local wine shop, brewery, the weekly farmers market, food trucks and Windermere Library. The main home was meticulously expanded and redesigned in

    Shelley Heistand PREMIER SOTHEBY'S INTL. REALTY

    105 Pine St, Windermere, FL 34786
  • 315 E 6th Ave, Windermere, FL 34786
    315 E 6th Ave, Windermere, FL 34786
    /2

    $939,000 Sold Apr 16, 2025

    • 2,869 Sq Ft
    • $327/SF
    • 13 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1964

    315 E 6th Ave, Windermere, FL 34786

    **This property qualifies for a closing cost credit up to $12,000 through the Seller’s preferred lender (restrictions apply).**Prepare to fall in love with this beautifully updated 4-bedroom, 3-bathroom pool home located in the heart of Windermere offering the perfect blend of modern comfort and timeless style! The circular driveway draws you in with the traditional white exterior, black accents,

    Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

    315 E 6th Ave, Windermere, FL 34786
  • 2812 Marquesas Ct, Windermere, FL 34786
    2812 Marquesas Ct, Windermere, FL 34786
    /2

    $3,100,000 Sold Apr 01, 2025

    • 5,624 Sq Ft
    • $551/SF
    • 55 Days On Market
    • 4 Beds
    • 5 Baths
    • Built 1984

    2812 Marquesas Ct, Windermere, FL 34786

    Exquisite architecture and design come together in this modern traditional luxury home in Downtown Windermere that seamlessly blends form, function and efficiency. With an abundance of decadent amenities throughout this stylish home, it's the perfect getaway for hosting gatherings with family and friends. The phenomenal outdoor spaces effortlessly merge with the indoor living areas raising the

    Kari Fleck THE REAL ESTATE COLLECTION LLC

    2812 Marquesas Ct, Windermere, FL 34786
  • 5000 Down Point Ln, Windermere, FL 34786
    5000 Down Point Ln, Windermere, FL 34786
    /2

    $3,750,000 Sold Mar 28, 2025

    • 5,802 Sq Ft
    • $646/SF
    • 236 Days On Market
    • 5 Beds
    • 5.5 Baths
    • Built 2002

    5000 Down Point Ln, Windermere, FL 34786

    Welcome to 5000 Down Point Lane in Windermere, a luxurious retreat situated on 2 acres of pristine lakefront property. This entirely renovated home offers breathtaking sunsets over Sunset Bay, providing a picturesque backdrop for daily living.The master suite, office, entertainment room and an additional suite are conveniently located on the main floor, while three more bedrooms and bonus

    Dianna Desboyaux SOUTHERN REALTY GROUP LLC

    5000 Down Point Ln, Windermere, FL 34786
  • 3302 Just-A-mere Ct, Windermere, FL 34786
    3302 Just-A-mere Ct, Windermere, FL 34786
    /2

    $1,180,000 Sold Mar 25, 2025

    • 2,450 Sq Ft
    • $482/SF
    • 18 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1986

    3302 Just-A-mere Ct, Windermere, FL 34786

    Beautifully maintained and upgraded by current owner, this charming family home is located in the highly sought after Windermere Town and has access to the BUTLER CHAIN OF LAKES! Secluded, private lot of over an acre creating oodles of potential for those looking to substantially extend the current home or build the home of their dreams! Ample parking and plenty of space to store your boat

    Sue Webb WATSON REALTY CORP.

    3302 Just-A-mere Ct, Windermere, FL 34786
  • 2119 Willow Brick Rd, Windermere, FL 34786
    2119 Willow Brick Rd, Windermere, FL 34786
    /2

    $846,500 Sold Mar 25, 2025

    • 2,728 Sq Ft
    • $310/SF
    • 254 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1990

    2119 Willow Brick Rd, Windermere, FL 34786

    Welcome Home! You will fall in love with this exquisite home located in the highly sought after Willows of Lake Rhea subdivision located in the hear of Windermere. This house is on .71 acers of pure relaxation. Since there are no neighbors right behind you the quiet green belt makes you feel you are secluded from the outside world. Once you open the doors to this home you are captivated by

    Stacey Jurek EXP REALTY LLC

    2119 Willow Brick Rd, Windermere, FL 34786
  • 7 1st Ct, Windermere, FL 34786
    7 1st Ct, Windermere, FL 34786
    /2

    $2,850,000 Sold Mar 21, 2025

    • 3,149 Sq Ft
    • $905/SF
    • 242 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1964

    7 1st Ct, Windermere, FL 34786

    Just like brand new, fully renovated by Davila Homes, this gorgeous home on Wauseon Bay in the Lake Butler Chain is taking shape. Featuring 4 bedrooms and 3 bathrooms, this home offers an amazing lakefront view and everything BRAND NEW plumbing, AC, electrical, septic system, top-of-the-line appliances and more. The modern, sophisticated design extends to the stunning backyard, which includes a

    Fernanda Negromonte NOVA REAL ESTATE SERVICES INC

    7 1st Ct, Windermere, FL 34786
  • 11154 Park Ave, Windermere, FL 34786
    11154 Park Ave, Windermere, FL 34786
    /2

    $835,000 Sold Mar 18, 2025

    • 3,355 Sq Ft
    • $249/SF
    • 210 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 1965

    11154 Park Ave, Windermere, FL 34786

    CERTIFIED PRE OWNED HOME. APPRAISAL COMPLETE NOV 2024! Unbeatable Opportunity to own this beautifully renovated home with Charming Character and DEEDED PRIVATE ACCESS TO BUTLER CHAIN OF LAKES! ROOF 2019- A true architectural masterpiece nestled in the reputable City of Windermere. This property is not just a home; its a chance to truly embark on a lifestyle of the town and the Lake! This 5

    Corinne Defilippis EXP REALTY LLC

    11154 Park Ave, Windermere, FL 34786
  • 407 W 1st Ave, Windermere, FL 34786
    407 W 1st Ave, Windermere, FL 34786
    407 W 1st Ave, Windermere, FL 34786
    /94

    $2,625,000 Sold Mar 12, 2025

    • 4,091 Sq Ft
    • $642/SF
    • 4 Days On Market
    • 6 Beds
    • 5.5 Baths
    • Built 1970

    407 W 1st Ave, Windermere, FL 34786

    Exceptional lakefront opportunity on the BUTLER CHAIN of Lakes! Nestled on the pristine shores of Wauseon Bay, this rare lakefront property offers an unparalleled opportunity to create the ultimate luxury retreat on the coveted Butler Chain. Set on a pristine, oversized lot (~1.26 acres) in one of the area’s most sought-after locations, this FENCED property offers a rare opportunity to create

    Ashley Boyd BHHS FLORIDA REALTY

    407 W 1st Ave, Windermere, FL 34786
  • 426 E 6th Ave, Windermere, FL 34786
    426 E 6th Ave, Windermere, FL 34786
    426 E 6th Ave, Windermere, FL 34786
    /64

    $600,000 Sold Mar 07, 2025

    • 1,698 Sq Ft
    • $353/SF
    • 124 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1976

    426 E 6th Ave, Windermere, FL 34786

    Seller says sell! For a limited time they will lower the price so don’t miss this opportunity Town of Windermere Gem !!! The one you've been waiting for has just hit the market, this UNIQUE opportunity won't last. This is a Gorgeous and Charming home in the Heart of Downtown Windermere. This 3/2 home has been tastefully renovated with no expense spared, EVERYTHING is brand new! from the roof,

    Jaime Leizan EXP REALTY LLC

    426 E 6th Ave, Windermere, FL 34786
  • 2523 Tryon Place, Windermere, FL 34786
    2523 Tryon Place, Windermere, FL 34786
    /2

    $1,390,000 Sold Feb 28, 2025

    • 4,028 Sq Ft
    • $345/SF
    • 122 Days On Market
    • 5 Beds
    • 6 Baths
    • Built 1994

    2523 Tryon Place, Windermere, FL 34786

    PRICE JUST REDUCED! GET THIS ONE BEFORE IT IS GONE! WELCOME HOME TO THE MANORS AT BUTLER BAY! This STUNNING Pool home is located in the HEART of Windermere and BOASTS 5 Bedrooms, 4 FULL/2 HALF Baths, an OVER-SIZED .65-acre lot with NO REAR Neighbors, and Retention Pond/Wooded Views. It features a 4 CAR Garage, 2 Bay-Attached Garage and 2 Bay-Detached Garage (perfect for your boat and all your

    Jay Kendall WATSON REALTY CORP

    2523 Tryon Place, Windermere, FL 34786
  • 10821 Bayshore Dr, Windermere, FL 34786
    10821 Bayshore Dr, Windermere, FL 34786
    /2

    $5,100,000 Sold Feb 28, 2025

    • 5,275 Sq Ft
    • $967/SF
    • 268 Days On Market
    • 4 Beds
    • 6 Baths
    • Built 2024

    10821 Bayshore Dr, Windermere, FL 34786

    Don't miss this rare opportunity to own the only new construction home currently available on the Butler Chain of Lakes. Just completed, this stunning transitional modern masterpiece is sure to take your breath away, featuring 200 feet of private, unobstructed views of Lake Down, on the famed Butler Chain of Lakes. As you step through the oversized steel pivot door, your eyes are immediately

    Christopher Christensen COMPASS FLORIDA LLC

    10821 Bayshore Dr, Windermere, FL 34786
  • 1295 Estancia Woods Loop, Windermere, FL 34786
    1295 Estancia Woods Loop, Windermere, FL 34786
    /2

    $1,475,000 Sold Feb 25, 2025

    • 4,098 Sq Ft
    • $360/SF
    • 22 Days On Market
    • 4 Beds
    • 5 Baths
    • Built 2018

    1295 Estancia Woods Loop, Windermere, FL 34786

    Step into luxury with this stunning 4-bedroom, 5-bathroom home on a spacious 1/3-acre lot offering nearly 4,100 sq ft of meticulously designed living space, blending elegance, comfort, and modern conveniences. The brick paver courtyard welcomes your guests and also provides a sense of privacy. Boasting expansive living spaces, high-end finishes, and an open-concept design, this home is perfect

    Desiree LaRoche KEENE'S POINTE REALTY

    1295 Estancia Woods Loop, Windermere, FL 34786
  • 12025 Lake Butler Blvd, Windermere, FL 34786
    12025 Lake Butler Blvd, Windermere, FL 34786
    /2

    $1,200,000 Sold Feb 25, 2025

    • 2,588 Sq Ft
    • $464/SF
    • 201 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1987

    12025 Lake Butler Blvd, Windermere, FL 34786

    REDUCED FOR QUICK SALE!! AMAZING OPPORTUNITY for a highly sought after BUILDING HOME SITE with income producing home on site. Buy now, build later. Rent the home until you are ready to tear down. Plans, design, contractors, financing available through LA. The existing home is nestled amidst the beauty of the Lake Butler community. Our spacious and picturesque property boasts over 1 acre of lush

    Sherry Duvall ADAIR REALTY INC

    12025 Lake Butler Blvd, Windermere, FL 34786
  • 2934 Marquesas Ct, Windermere, FL 34786
    2934 Marquesas Ct, Windermere, FL 34786
    /2

    $1,700,000 Sold Feb 24, 2025

    • 4,001 Sq Ft
    • $425/SF
    • 3 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1985

    2934 Marquesas Ct, Windermere, FL 34786

    Nestled in the Town of Windermere, this gated waterfront neighborhood is a haven of security and privacy. This Custom one-story lake house is distinguished by its long, winding circular drive lined with mature oaks. The home features a timeless modern exterior with abundant windows, thoughtfully designed to embrace the stunning natural surroundings. While it may need some updating, the

    Judy Black UPSIDE REAL ESTATE INC

    2934 Marquesas Ct, Windermere, FL 34786
  • 4 Chase Rd, Windermere, FL 34786
    4 Chase Rd, Windermere, FL 34786
    /2

    $825,000 Sold Feb 21, 2025

    • 2,386 Sq Ft
    • $346/SF
    • 166 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1971

    4 Chase Rd, Windermere, FL 34786

    Welcome to Historic Downtown Windermere. This stunning, fully remodeled mid-century-modern home is ready to welcome its new owner into a life like none other. Located in the golf cart district, you have convenient access to a private boat ramp and two public boat ramps, community parks, tennis courts, and a downtown district that boasts charm and exclusivity. Besides an idyllic lifestyle, this

    Matt Kester THE REAL ESTATE COLLECTION LLC

    4 Chase Rd, Windermere, FL 34786
  • 19 Main St, Windermere, FL 34786
    19 Main St, Windermere, FL 34786
    /2

    $1,150,000 Sold Feb 05, 2025

    • 2,331 Sq Ft
    • $493/SF
    • 191 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1959

    19 Main St, Windermere, FL 34786

    BACK ON THE MARKET DUE TO BUYER PERFORMANCE! Priced below recent appraisal! Welcome to waterfront luxury living at its finest in the heart of Windermere, nestled along the serene Butler Chain of Lakes. This impeccably renovated 4-bedroom, 3-bathroom home offers 100 feet of direct Fischer canal frontage, and is located between Lake Down and Wauseon Bay, providing a picturesque backdrop for your

    Corey Mathias LAKESIDE REALTY WINDERMERE INC

    19 Main St, Windermere, FL 34786
  • 216 Magnolia St, Windermere, FL 34786
    216 Magnolia St, Windermere, FL 34786
    /2

    $1,500,000 Sold Feb 01, 2025

    • 3,787 Sq Ft
    • $396/SF
    • 2 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 2016

    216 Magnolia St, Windermere, FL 34786

    Located in the charming Town of Windermere, this custom-built residence boasts an unrivaled location just across the street from Lake Down, offering partial lake views from the upstairs windows. With an expansive backyard and a beautiful gated large outdoor pool, this home is perfect for both relaxation and entertaining.The interior features a gourmet kitchen with stainless steel

    Mark Allen REALTY INTERNATIONAL LLC

    216 Magnolia St, Windermere, FL 34786
  • 11018 Lake Butler Blvd, Windermere, FL 34786
    11018 Lake Butler Blvd, Windermere, FL 34786
    /2

    $2,750,000 Sold Jan 15, 2025

    • 3,923 Sq Ft
    • $701/SF
    • 58 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2001

    11018 Lake Butler Blvd, Windermere, FL 34786

    Discover luxury living in this stunning estate located on renowned Lake Butler Blvd, overlooking Wauseon Bay of the Butler Chain of Lakes. Set on close to one acre of beautifully landscaped grounds, this private oasis is designed for both relaxation and entertainment. As you enter through the winding driveway, you'll be greeted by lush landscaping and a detached oversized garage, fully

    Steve Healy CORCORAN PREMIER REALTY

    11018 Lake Butler Blvd, Windermere, FL 34786
  • 628 Forest St, Windermere, FL 34786
    628 Forest St, Windermere, FL 34786
    /2

    $595,000 Sold Dec 18, 2024

    • 750 Sq Ft
    • $793/SF
    • 6 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1945

    628 Forest St, Windermere, FL 34786

    Nestled under majestic oaks, this charming 1940s one-bedroom cottage captures the essence of Old Windermere living. With its picturesque curb appeal featuring a paver driveway and custom treehouse, this property is truly one of a kind.Step inside to find wide plank wood floors, solid surface countertops, and updated appliances that complement the home’s timeless character. Enjoy your morning

    Judy Black UPSIDE REAL ESTATE INC

    628 Forest St, Windermere, FL 34786
  • 11555 Willow Gardens Dr, Windermere, FL 34786
    11555 Willow Gardens Dr, Windermere, FL 34786
    /2

    $1,450,000 Sold Nov 18, 2024

    • 3,754 Sq Ft
    • $386/SF
    • 15 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 1994

    11555 Willow Gardens Dr, Windermere, FL 34786

    Welcome to your .58 acre dream home in the serene Willows at Lake Rhea community in Windermere! With a brand new 50+ year tile roof (8/2024) complete with gutters and downspouts, plus a completely paid off solar system (2022), you can rest easy knowing that peace of mind and super low electric bills are here to stay! Step inside to discover the beauty that is your view! Brand new high quality

    Bistra Iordanova CHARLES RUTENBERG REALTY ORLANDO

    11555 Willow Gardens Dr, Windermere, FL 34786
  • 133 Main St, Windermere, FL 34786
    133 Main St, Windermere, FL 34786
    /2

    $550,000 Sold Oct 31, 2024

    • 1,166 Sq Ft
    • $472/SF
    • 101 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1963

    133 Main St, Windermere, FL 34786

    **Price improvement! Sellers motivated!** Now is your chance to live the true Windermere lifestyle, "Among the Lakes"! Make this charming 3/2 home your haven for all that the Town Windermere has to offer. No HOA restrictions, well maintained, and move-in ready, this home sits on an impressive 95 ft X 150 ft corner lot in the very heart of the Town of Windermere. Located just a few blocks from the

    Bill Martini BHHS FLORIDA REALTY

    133 Main St, Windermere, FL 34786
  • 721 Magnolia St, Windermere, FL 34786
    721 Magnolia St, Windermere, FL 34786
    /2

    $650,000 Sold Oct 30, 2024

    • Land
    • 0.38 Acre
    • $1,710,526 per Acre
    • 65 Days On Market

    721 Magnolia St, Windermere, FL 34786

    This is a rare opportunity to own a two-home parcel in the highly sought-after community of Windermere. This property is ideal for use as a rental or to tear down and make the lot the new location of your custom-built dream home! As rental units, these bungalow-style homes are ideally located close to the center of downtown Windermere and Lake Bessie. Both homes offer 2 bedrooms,1 bathroom, plus

    Steve Healy CORCORAN PREMIER REALTY

    721 Magnolia St, Windermere, FL 34786

Showing Results 1 - 40, Page 1 of 2

Florida Orange County Windermere Windermere

Recently Sold Real Estate & Homes in Windermere, Windermere

Learn more about living in Windermere

Frequently Asked Questions

What is the average time to sell a house in Windermere, FL?
The houses for sale in Windermere, FL spend an average of 48 days on the market.
What is the number of active homes for sale in Windermere, FL?
There are 6 active homes for sale in Windermere, FL.

Home Trends in Windermere, FL

On average, homes in Windermere, FL sell after 48 days on the market compared to the national average of 70 days. The median sale price for homes in Windermere, FL over the last 12 months is $435,000, up 18% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$435,000
Median Single Family Sale Price
$380,000
Median Townhouse Sale Price
$250,000
Median 2 Bedroom Sale Price
$344,900
Average Price Per Sq Ft
$375
Number of Homes for Sale
6
Last 12 months Home Sales
53
Months of Supply
1.40
Median List Price
$372,990
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
18%
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