Displaying: For Sale
Location: Winter Haven
Property Type(s): Villas
Living Area Square Feet: 1500 to 1999
Do Not Show Listings
Winter Haven - 5 properties found
29 ENCLAVE DR, WINTER HAVEN, FL 33884
$259,90061 Days on yellowkey MLS ID: L4959890
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1526 Built: 1995Monthly Fee: $433 Tax: $1,844 (2025)Community: Cypresswood Enclave Ph 01Villa
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,844
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: New to the market is this "one owner" villa located in the sought-after Enclave neighborhood located in Cypresswood Golf and Country Club in SE Winter Haven. This 3 bedroom 2 bathroom end unit has just undergone a professional interior paint job. Enjoy Easterly pasture and sunrise views from the lanai. The country club amenities include access to the clubhouse with bar and grill, jr. olympic swimming pool and soon to be completed pickleball courts. The championship 18 hole golf course is open to the public. As an added bonus, Publix is opening a brand new location just a mile down the road which is sure to attract other popular businesses.
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Steven Smith, Pa (863-224-2297)
69 ENCLAVE DR, WINTER HAVEN, FL 33884
$300,0006 Days on yellowkey MLS ID: S5148089
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1682 Built: 1998Monthly Fee: $435 Tax: $2,189 (2024)Community: Cypresswood Enclave Ph 02Villa
Taxes:$2,189
Elementary School: Elbert Elem
High School: Winter Haven Senior
Tax Year: 2024
Middle School: Denison Middle
Remarks: Welcome to 69 Enclave Drive, a beautifully updated home nestled inside the sought-after Cypresswood Golf & Country Club, a gated golf community known for its lush landscaping, resort-style amenities, and peaceful, secure atmosphere right in the heart of Polk County. From the moment you arrive, the manicured curb appeal sets the tone: mature palms, trimmed hedges, and a well-maintained façade with a two-car garage greet you at the entry. Step inside and you'll immediately notice the quality of every update, high-end laminate flooring flows throughout the home, complementing the fresh, modern palette and abundant natural light. The fully updated kitchen is a true showstopper, featuring custom raised-panel cabinetry, stunning granite countertops, a designer arabesque tile backsplash, and a full suite of stainless steel appliances, all included. A skylight above adds a bright, airy feel that makes cooking here a genuine pleasure. The spacious open-concept living and dining areas are designed for how Florida families actually live, wide open, light-filled, and flowing seamlessly toward the backyard through large sliding glass doors. The living room offers an ideal layout for entertaining, with a vaulted ceiling effect and views out to the lush, private backyard. Plantation shutters add a polished, upscale touch throughout. Bathrooms have been tastefully renovated with matching granite vanities, updated fixtures with brushed nickel hardware, and designer tile surrounds, all carrying that same cohesive, elevated look. The screened lanai is your private Florida retreat, perfect for morning coffee or evening sunsets, while the backyard offers mature trees, green space, and real privacy. An aerial view reveals just how spacious and private this lot truly is within the community. Practical updates make this home truly move-in ready: newer thermal windows for energy efficiency, a newer gas water heater, an updated laundry room with custom cabinetry, and a stunning epoxy-coated garage floor that gives the two-car garage a clean, finished look with room to spare. Living in Cypresswood means access to golf, a clubhouse, community pool, and the peace of mind that comes with a gated, well-managed neighborhood, all just minutes from shopping, dining, medical facilities, and major corridors serving the greater Central Florida area. Homes in Cypresswood at this level of finish don't last. Schedule your private showing today.
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Manny Quiros (863-221-3036)
2813 WINGFOOT CT, WINTER HAVEN, FL 33884
$215,00062 Days on yellowkey MLS ID: L4959887
REDUCED by $15,000 (6.5%) on 04/15/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1682 Built: 1990Monthly Fee: $295 Tax: $2,981 (2025)Community: Cypresswood Golf VillasSpa: NoVilla
Taxes:$2,981
Remarks: Welcome to 2813 Wingfoot Court — now one of the best values in Cypresswood Golf & Country Club! Perfectly positioned along the 8th fairway inside this guard-gated golf community, this beautifully maintained 2-bedroom, 2-bath villa offers peaceful views and effortless Florida living—now at an exceptional new price. Being sold fully furnished and truly turnkey, this home is ready for immediate enjoyment—just bring your suitcase. Inside, you’ll find a professionally designed interior with vaulted ceilings that create a bright, open feel throughout the main living spaces. The kitchen includes updated appliances, including a newer stove and microwave, while most windows have been upgraded for improved efficiency and style. A tankless hot water heater adds modern convenience and energy savings. The spacious primary suite features a walk-in closet and private bath, while the guest bedroom also offers a walk-in closet and easy access to a second full bath—perfect for hosting family and friends. One of the home’s standout features is the inviting Florida room, ideal for morning coffee or relaxing after a day on the course. Step outside to the stained and stamped patio overlooking the fairway, creating a perfect space for entertaining or unwinding. Major updates include a roof (2019) and A/C (2018), providing added peace of mind. Residents enjoy access to community amenities including a pool, tennis courts, clubhouse, and on-site restaurant—all just minutes from shopping, dining, and major roadways. Now aggressively priced—don’t miss this opportunity to own in Cypresswood at one of the most attractive price points in the community.
Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)
Listing Agent: Corinna Weaver (863-258-2901)
2817 WINGFOOT CT, WINTER HAVEN, FL 33884
$270,000269 Days on yellowkey MLS ID: P4935798
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1666 Built: 1990Monthly Fee: $285 Tax: $1,448 (2024)Community: Cypresswood Golf Villas Gc-2Spa: NoVilla
Taxes:$1,448
Remarks: Welcome to 2817 Wingfoot Ct, located in the desirable Cypresswood Golf Villas. This beautifully maintained villa sits along the 8th fairway of the prestigious Cypresswood Golf & Country Club, a guard-gated community offering both privacy and tranquility. Inside, you'll find three spacious bedrooms and two full bathrooms. The living and dining areas feature vaulted ceilings that enhance the open and airy atmosphere. The eat-in kitchen is a standout with new custom cabinetry, granite countertops, and a convenient closet pantry. Flooring throughout the home includes durable laminate and ceramic tile, with cozy carpeting in the third bedroom. The primary suite offers sliding doors to the patio, a generous walk-in closet, and an updated bathroom. The secondary bedroom also includes a walk-in closet, while the third bedroom features patio access and a European-style A/C unit. Major updates include a roof replacement in 2022, and a new A/C system installed in 2019. Covered parking adds convenience. Enjoy resort-style living with scenic golf course views and access to community amenities, all just minutes from shopping, dining, and major roadways. Whether you're seeking a year-round residence or a seasonal escape, this villa is the perfect place to call home. Community pool, tennis, clubhouse & restaurant.
Listing is courtesy of: NEXTHOME NORRIS & COMPANY REALTY (863-875-5583)
Listing Agent: Michael Norris (863-287-3105)
2805 WINGFOOT CT, WINTER HAVEN, FL 33884
$245,50063 Days on yellowkey MLS ID: B4902197
1 Days Off yellowkey (back on 4/4/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1602 Built: 1987Monthly Fee: $295 Tax: $1,543 (2025)Community: Cypress WoodVilla
Taxes:$1,543
Remarks: Under contract-accepting backup offers. Fully Renovated Golf Course Home – Perfect for Full or Part-Time Living Located directly on the golf course in Cypress Woods Golf & Country Club, this beautifully renovated home is a 2 bedroom, 2-bath home with an optional 3rd bedroom or sunroom. Home showcases quality craftsmanship and modern upgrades throughout — ideal for both full-time residents and seasonal owners. The open floor plan features updated flooring, designer lighting, and a completely remodeled kitchen with premium cabinetry, Corian countertops, stainless-steel appliances, new hot water heater and air conditioning system. Both bathrooms have been tastefully renovated with stylish, high-end finishes. The spacious primary suite offers a beautifully updated en-suite bath and its own private porch, creating a peaceful retreat. Positioned on the golf course, the home enjoys a prime setting within this desirable Central Florida community. Community amenities include championship golf, clubhouse dining, fitness center, and a resort-style pool. This move-in ready home offers comfort, quality, and convenience in a highly sought-after location.
Listing is courtesy of: FAITH AND FAMILY REALTY LLC (863-712-1991)
Listing Agent: Lynn Arthur (336-596-5547)
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