16

Windermere, FL Homes for Sale under $400,000

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  • /38

    $370,000

    • 4 Beds
    • 2.5 Baths
    • 2,067 Sq Ft

    14234 Desert Haven St Unit 14234, Windermere, FL 34786

    Spacious and well-appointed, this 4-bedroom, 2.5-bath townhome is the largest floor plan available in the community, offering over 2,000 square feet of comfortable living space. The layout includes a 2-car garage, screened-in patio, and a private fenced courtyard—perfect for relaxing outdoors or grilling with friends.Inside, the first floor features all tile flooring—durable, stylish, and

    Agent Photo

    Debi Roldan

    KELLER WILLIAMS ADVANTAGE III

    (407) 975-5312

    14234 Desert Haven St Unit 14234, Windermere, FL 34786
  • /26

    $385,000

    • 3 Beds
    • 2.5 Baths
    • 1,461 Sq Ft

    5219 Keenes Pheasant Dr, Windermere, FL 34786

    Beautifully Maintained 3-Bedroom Townhome in Sought-After Summerport!Don’t miss this spacious and move-in ready townhouse located in the heart of Summerport, one of the area’s most desirable communities. This light-filled home features 3 bedrooms, 2.5 bathrooms, and an open floor plan perfect for modern living.The primary suite is conveniently located on the first floor and

    Roland Cotardo THE SIMON SIMAAN GROUP

    5219 Keenes Pheasant Dr, Windermere, FL 34786
  • /60

    $399,900

    • 3 Beds
    • 2.5 Baths
    • 1,644 Sq Ft

    7752 Moser Ave, Windermere, FL 34786

    REDUCED! PRICED TO SELL! STUNNING WINDERMERE TOWNHOME!! This meticulously maintained end-unit townhome offers three bedrooms, 2.5 bathrooms, and a host of modern upgrades including new LG smart appliances and fresh paint throughout the entire home. From the moment you arrive, you'll appreciate the HOA-manicured landscaping, charming front porch, and striking tall entry door. Inside, the

    Jay Wells JAY WELLS REAL ESTATE INC

    7752 Moser Ave, Windermere, FL 34786
  • /22

    $389,990

    • 3 Beds
    • 2.5 Baths
    • 1,520 Sq Ft

    7621 Sutherton Ln, Windermere, FL 34786

    Modern Townhome in Windermere’s Wickham Park 3 Beds | 2.5 Baths | 2-Car Garage | Prime LocationWelcome to this beautifully maintained townhome in the highly sought-after community of Wickham Park, located in the heart of Windermere, Florida — where charm, convenience, and top-rated schools come together.Step inside to an inviting open floor plan with ceramic tile throughout

    Gabriela Lanza MY REALTY GROUP, LLC.

    7621 Sutherton Ln, Windermere, FL 34786
  • /20

    $389,000

    • 3 Beds
    • 2.5 Baths
    • 1,369 Sq Ft

    12744 Langstaff Dr, Windermere, FL 34786

    Beautiful townhouse located in Windermere, 3 br, 2.5 baths, full of natural lighting and unparalleled tranquility, featuring a private and fenced courtyard. Nice modern upgraded flooring and color scheme, new kitchen with quartz counter top, new hight in appliances, new AC. Beautiful Community pool and kiddie park. This home is so conveniently located close to Disney, mayor shopping & dining

    Ana Fermin PROPERTY WAREHOUSES OF AMERICA

    12744 Langstaff Dr, Windermere, FL 34786
  • /21

    $399,990

    • 3 Beds
    • 2.5 Baths
    • 1,462 Sq Ft

    5235 Keenes Pheasant Dr, Windermere, FL 34786

    Charming 3-Bedroom Townhome in a Prime Location!Welcome home to this beautifully maintained 3-bedroom, 2.5-bath townhome offering 1,462 sq. ft. of comfortable living space. The spacious open-concept floor plan features a roomy kitchen, cozy family room, and a flex space that could be used as a home office—all conveniently located downstairs. Upstairs, you’ll find all three bedrooms, including

    Ronda Shively COMPASS FLORIDA LLC

    5235 Keenes Pheasant Dr, Windermere, FL 34786
  • /21

    $397,499

    • 2 Beds
    • 2.5 Baths
    • 1,510 Sq Ft

    12335 Cruxbury Dr, Windermere, FL 34786

    Discover this spacious 2-bedroom, 2.5-bath end-unit townhome nestled in a charming Windermere community known for its tree-lined streets, sidewalks, and beautiful canopied trees. Step inside to find brand new carpet throughout and a functional layout featuring a large kitchen and great room, plus an additional flex space at the front of the home—perfect for a home office or playroom. The kitchen

    Amy Kidwell PREFERRED REAL ESTATE BROKERS

    12335 Cruxbury Dr, Windermere, FL 34786
  • /21

    $400,000

    • 3 Beds
    • 2.5 Baths
    • 1,936 Sq Ft

    7660 Ripplepointe Way, Windermere, FL 34786

    Seller will contribute toward buyer's closing costs and/or interest rate buydown.Welcome home to your beautiful town home in the sought-after town of Windermere! This three-bedroom, 2.5-bath residence offers a blend of comfort, style and functionality. The open-concept layout connects the kitchen complete with 42-inch solid wood cabinets with granite countertops to the dining and living areas,

    Brady Richardson PREMIER SOTHEBYS INT'L REALTY

    7660 Ripplepointe Way, Windermere, FL 34786
  • /28

    $339,000

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

    8168 Boat Hook Loop Unit 107, Windermere, FL 34786

    Stunning Oasis in the Heart of Windermere! This is a must-see jewel with nice appointments and an open floor plan. It is perfect for your retirement home, busy professional or a first-time buyer !!!This beautiful 3-bedroom ground floor condo located conveniently opposite the clubhouse which has all the luxury amenities you could ask for. Inside you'll be impressed by the size of the living space

    Leonardo Rico UNITED REAL ESTATE PREFERRED

    8168 Boat Hook Loop Unit 107, Windermere, FL 34786
  • /34

    $339,000

    • 3 Beds
    • 2.5 Baths
    • 1,460 Sq Ft

    8259 Maritime Flag St Unit 4, Windermere, FL 34786

    One or more photo(s) has been virtually staged. Experience the best of Windermere living! This freshly updated two-story townhome offers resort-style amenities and unbeatable convenience, all just 10 minutes from Disney!Step inside to discover fresh paint throughout, brand new carpet, and an open-concept first floor with a kitchen/living room combo and a half bath. Upstairs, you’ll find

    Lindsey Hudson REAL BROKER, LLC

    8259 Maritime Flag St Unit 4, Windermere, FL 34786
  • /28

    $364,750

    • 2 Beds
    • 2.5 Baths
    • 1,280 Sq Ft

    7418 Bentonshire Ave, Windermere, FL 34786

    Welcome to this beautifully maintained 2-bedroom, 2.5-bathroom townhouse in the highly desirable community of Wickham Park in Windermere.Built in 2007, this move-in-ready home offers 1,228 square feet of comfortable living space—perfect for homeowners or investors alike.Recent upgrades include freshly painted walls, professionally cleaned carpets, and a renovated screened-in

    Victor Barroeta MBT REALTY LLC

    7418 Bentonshire Ave, Windermere, FL 34786
  • /28

    $340,000

    • 3 Beds
    • 2.5 Baths
    • 1,534 Sq Ft

    14242 Desert Haven St Unit GE, Windermere, FL 34786

    Located in the gated community of Oasis Cove, this 3-bedroom, 2.5-bathroom condo offers a comfortable, low-maintenance lifestyle just minutes from Disney—with clear views of the nightly fireworks from your own home.The interior features a functional two-story layout with all bedrooms located upstairs, providing separation between living and private spaces. The main floor includes an

    James Goodyear REAL BROKER, LLC

    14242 Desert Haven St Unit GE, Windermere, FL 34786
  • /66

    $369,800

    • 3 Beds
    • 2.5 Baths
    • 1,480 Sq Ft

    7462 Bentonshire Ave, Windermere, FL 34786

    BIG price reduction for this move in ready 3/2.5 Townhome in Windermere! New roof 2024. AC compressor new June 2025. Rear entry 2 car garage. All stainless-steel fridge, stove, microwave and dishwasher with solid surface counter tops. Versatile all ceramic tiled 1st floor plan with formal dining room or use as front office. Open kitchen to rear great room that opens to covered screened private

    Ivan Petkov FLORIDA REALTY INVESTMENTS

    7462 Bentonshire Ave, Windermere, FL 34786
  • /27

    $386,000

    • 3 Beds
    • 2.5 Baths
    • 1,786 Sq Ft

    14025 Oasis Springs Ln Unit 901, Windermere, FL 34786

    ***3D Tour on Virtual Tour Link 1*** This immaculately kept, gated end unit townhome boasts 3 bedrooms and 2.5 bathrooms. Step inside to discover a spacious layout seamlessly connecting the kitchen to the family room. The kitchen shines with stainless steel appliances, elegant wood cabinetry, and a convenient breakfast bar. Upstairs, the master suite awaits with a walk-in closet, double vanity,

    Jorge Martinez, Jr KELLER WILLIAMS CLASSIC

    14025 Oasis Springs Ln Unit 901, Windermere, FL 34786
  • /20

    $345,000

    • 3 Beds
    • 2.5 Baths
    • 1,363 Sq Ft

    8271 Maritime Flag St Unit 109, Windermere, FL 34786

    Property is TENANT occupied.LEASE EXPIRES ON 02/28/2026. Welcome to Lakeside at Lakes of Windermere! This townhome seamlessly combines comfort and convenience within one of Windermere’s most sought-after communities. Featuring 3 bedrooms and 2 and half bathrooms. NEW AC UNIT. The primary bedroom with an ensuite bathroom offering dual sinks, a tub/shower combo, and a generous walk-in closet. The

    Daniela de Rodriguez B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE

    8271 Maritime Flag St Unit 109, Windermere, FL 34786
  • /57

    $335,000

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

    11446 Jasper Kay Terrace Unit 106 (1006), Windermere, FL 34786

    Whether you are looking for a primary residence, an investment property with a very high rental demand for its location and comfort or a vacation retreat, this condo is perfect for you. Beautiful condo located in Lakeside at Lakes of Windermere, corner unit on the first floor (ground floor) with covered balcony. Welcome to this stunning condo located in one of the best and most exclusive areas of

    Euclides Sebastiani Marquez ROMAN'S PRO REALTY LLC

    11446 Jasper Kay Terrace Unit 106 (1006), Windermere, FL 34786

Home Trends in Windermere, FL

Housing Trends

Median Sale Price
$685,000
Median Single Family Sale Price
$910,000
Median Townhouse Sale Price
$412,000
Average Price Per Sq Ft
$339
Number of Homes for Sale
175
Last 12 months Home Sales
445
Months of Supply
4.70
Median List Price
$780,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
3%
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