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Cypresswood Multifamily Homes & Duplexes for Sale

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  • /24

    $205,000

    • 2 Beds
    • 2 Baths
    • 1,164 Sq Ft

    2282 Firestone Place, Winter Haven, FL 33884

    Welcome to Cypresswood Golf & Country Club Living!Discover this charming 2-bed, 2-bath, single-story Golf Villa at 2282 Firestone Pl in the exclusive gated community of Cypresswood in Winter Haven, FL. Boasting 1,164 sq ft of thoughtfully designed living space, this villa offers the perfect blend of comfort, style, and sweeping golf course views.Key Features & Upgrades:Two inviting

    Juan Yglesias KELLER WILLIAMS REALTY SMART 1

    2282 Firestone Place, Winter Haven, FL 33884
  • /46

    $234,900

    • 2 Beds
    • 2 Baths
    • 1,563 Sq Ft

    1077 Medinah Way, Winter Haven, FL 33884

    HARD TO FIND ...YET EASY TO OWN.!!! ENJOY COMING HOME TO THIS WONDERFUL COMMUNITY IN A TENNIS VILLA. IT IS A SPACIOUS END UNIT IN THE BEAUTIFUL CYPRESSWOOD GOLF AND TENNIS COMMUNITY WITH LOTS OF AMENITIES INCLUDING GATE SECURITY. CALL TO PREVIEW THIS WELL-MAINTAINED 2 BED 2 BATH CB VILLA, WITH FORMAL LIVING AND DINING AREA, SPACIOUS FLORIDA ROOM OVERLOOKING THE TENNIS COURTS AND POOL AREA, NICE

    Heidi Gravel WESTLAKE REAL ESTATE CO., INC.

    1077 Medinah Way, Winter Haven, FL 33884
  • /46

    $264,900

    • 3 Beds
    • 2 Baths
    • 1,526 Sq Ft

    13 Enclave Dr, Winter Haven, FL 33884

    Welcome to this maintained 3 bedroom, 2 bath one-story villa/townhouse located in Enclave, a quiet and desirable neighborhood within the gated golf community of Cypresswood Golf & Country Club. This spacious end-unit features a functional split-bedroom floor plan, generous living and dining areas, and an inviting Florida room that adds to the overall living space. The kitchen offers ample cabinet

    Suzanna Rudd KELLER WILLIAMS REALTY SMART 1

    13 Enclave Dr, Winter Haven, FL 33884
  • /31

    $219,900

    • 2 Beds
    • 2 Baths
    • 1,430 Sq Ft

    2254 Firestone Place, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. Welcome home to this spacious 2-bedroom/2-bathroom Golf Villa located in the highly-sought-after Cypresswood community of Winter Haven and enjoy nearly maintenance-free living. Renovations completed in recent years include newer luxury vinyl flooring, kitchen appliances, and a freshly painted interior. This single-story villa offers TWO outdoor

    Kayly Malinas JOHN WOOD REALTY, INC.

    2254 Firestone Place, Winter Haven, FL 33884
  • /44

    $224,900

    • 2 Beds
    • 2 Baths
    • 1,278 Sq Ft

    1039 Medinah Dr, Winter Haven, FL 33884

    1 OWNER HOME!! Don't miss out on this 2 bed 2 bath tennis villa in the highly desired neighborhood of Cypresswood. The HOA takes care of the roof, lawn, paint, and exterior maintenance. Enjoy the security of living in a community with a 24 hour guard at the gate. There is plenty to do all within the community. There is a golf course, restaurant, community pool and tennis courts. The home has all

    Robert webb JOHN WEBB INC

    1039 Medinah Dr, Winter Haven, FL 33884

Why Live in Cypresswood

Cypresswood in Winter Haven is a master-planned community known for its golf courses and country club amenities. With over 1,000 residential units and 14 neighborhood associations, it offers diverse housing options, primarily ranch-style homes from the 1980s to early 2000s, with new custom builds still emerging. The Cypresswood Golf & Country Club, featuring the best golf course in Winter Haven for 2023, is a central attraction. Residents enjoy country club amenities, including pools, gyms, and tennis courts, with plans to add pickleball courts. The neighborhood is close to shopping and dining, with a Winn-Dixie within 2 miles and a Walmart Supercenter under 6 miles away. Local dining includes the Cypresswood Pub, Legacy Craft BBQ, and Dundee Diner. For outdoor activities, the nearby Michael V. Lewis Arboretum and Parrott Trail offer 42 acres of native and exotic plants. Cypresswood is under 5 miles from Legoland and less than 30 minutes from Disney World, with both east and west coast beaches about 2 hours away. The neighborhood is zoned for Polk County Public Schools, one of the top 50 districts in Florida. Public transportation is not available, so residents rely on cars or golf carts, with major routes like US Highway 27 and Florida State Road 60 nearby. Orlando International Airport is about 45 miles away.

Home Trends in Cypresswood, FL

Housing Trends

Median Sale Price
$275,000
Median Single Family Sale Price
$309,995
Median 2 Bedroom Sale Price
$185,000
Average Price Per Sq Ft
$179
Number of Homes for Sale
52
Last 12 months Home Sales
85
Months of Supply
7.30
Median List Price
$310,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
-12%
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