Displaying: For Sale
Location: Winter Haven
Property Type(s): Villas
Beds: 3 to 3
Do Not Show Listings
Winter Haven - 7 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)
1039 MEDINAH DR, WINTER HAVEN, FL 33884
$195,00056 Days on yellowkey MLS ID: P4938088
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1278 Built: 1980Monthly Fee: $290 Tax: $2,627 (2025)Community: CypresswoodVilla
Taxes:$2,627
Remarks: 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 new flooring, paint, and granite counter tops. Make your appointment TODAY!!
Listing is courtesy of: JOHN WEBB INC (863-422-2999)
Listing Agent: Robert Webb (863-557-6229)
104 WODEN WAY, WINTER HAVEN, FL 33884
$379,000375 Days on yellowkey MLS ID: P4934554
REDUCED by $26,000 (6.4%) on 04/19/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2218 Built: 1981Monthly Fee: $382 Tax: $4,453 (2024)Community: ValhallaVilla
Taxes:$4,453
Remarks: Valhalla - A GATED subdivision with pool, club house and more! 3-bedroom, 2-bath villa home with a connecting property but considered a single family home. This special villa has a functional layout with updated features throughout. A screened entry with leaded glass doors opens to vaulted ceilings and custom architectural touches. The open concept kitchen includes granite countertops, custom cabinetry, a center island with breakfast bar, Bosch dishwasher, stainless oven and range, walk-in pantry, and a passthrough to the living area for open flow. Wood plank flooring runs throughout the main spaces. The living room features large windows and an adjacent flex space for dining, office, or den use. The primary suite includes an ensuite bathroom with slate tile, jacuzzi tub, glass shower, dual sinks, and the laundry room is part of the primary. The guest room features a window seat and recessed lighting. A third room functions well as an office or additional guest space. HOA covers lawn care, water, trash, basic cable, pool, and tennis access.
Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)
Listing Agent: Karen Myers (863-651-4636)
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)
35 ENCLAVE DR, WINTER HAVEN, FL 33884
$242,500577 Days on yellowkey MLS ID: P4932313
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2070 Built: 1997Monthly Fee: $429 Tax: $1,632 (2023)Community: Cypresswood Enclave Ph 02Villa
Taxes:$1,632
Tax Year: 2023
Remarks: JUST REDUCED!!! SPACIOUS THREE BEDROOM ENCLAVE UNIT WITH A TRANQUIL VIEW IN CYPRESSWOOD GOLF & COUNTRY CLUB!!! VILLA WITH OVER 2,000 PLUS SQ. FT. LIVING 3 BEDROOM 3 BATH PLAN AND NEW TILE FLOORING IN THE PRIMARY BATH, NEW ROOF IN 2023. You will enjoy this maintenance-free home, the largest villa floor plan in the Cypresswood Enclave designed with an open floor plan, volume ceilings and tranquil pasture views! Upgrades include beautiful hardwood floors & plantation shutters. The eat-in kitchen boasts real wood cabinets, solid surface counter tops & stainless appliances with a gas stove the "Chef" will appreciate! There is privacy for all with a triple split design featuring 3 bedrooms and 3 full baths with two "En-suite" primary bedrooms that are both spacious with a walk-in shower, dual vanities and separate soaking tub. There is an abundance of walk-in closets & great storage. The skylights allow for extra natural light in this well-cared for home - bright & airy throughout! There are no rear neighbors. You'll love the pasture views & the cattle ranch allows for expansive views for the nature lovers. The 2-car garage with workbench is a perfect hobby spot. Cypresswood is best known for its fabulous Florida lifestyle - golf course, 24 hr. manned security gate, tennis courts, large community pool, biking, walking, and you'll appreciate the clubhouse restaurant with local musical venues! This property is within close proximity to shopping, restaurants, LEGOLAND, and so much more, so call today to set up a private showing!!!
Listing is courtesy of: THE K TEAM REAL ESTATE SERVICES LLC (863-604-1601)
Listing Agent: Cathy Kluytenaar (863-604-6220)
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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