Cypresswood Patio Homes Homes for Sale in Winter Haven - 7 homes

Remarks: Relaxed golf community living inside the gated and guarded Cypresswood Golf & Country Club. Welcome to 460 Pinehurst Ct in Winter Haven, Florida — an updated and spacious 2 bedroom, 2 bath patio home tucked away on a quiet cul-de-sac street with no through traffic. A private walled walkway leads to a charming front porch with sitting area, creating a warm and welcoming approach. Step inside the foyer to discover a clean, updated interior offering more than 1,600 square feet of comfortable living space, highlighted by beautiful new flooring, a freshly painted interior, and a long list of thoughtful improvements. All carpeting has been removed, the outdated popcorn ceilings have been scraped and refinished for a more modern look, and the overgrown landscaping has been cleared away to create a clean, attractive, and easy-to-maintain property. The roof was replaced in 2020 for added peace of mind, and gutters have also been installed for convenience and functionality. The great room design creates a spacious and open feel, accentuated by built-in shelving and large glass sliders that bring in natural light while offering the perfect space to showcase personal décor and seasonal accents. Sliding glass doors open to the enclosed, air-conditioned Florida room, seamlessly expanding the living area and creating an easy indoor-outdoor lifestyle that can be enjoyed year-round. The great room also offers space for formal dining in addition to the casual eat-in area found within the kitchen. The generously sized kitchen features abundant real wood cabinetry, a large breakfast bar, closet pantry, and an inviting dining area ideal for casual meals and everyday living. The primary suite offers comfortable dimensions, a walk-in closet, and an en-suite bath complete with a tiled walk-in shower. The guest bedroom is also nicely sized and features its own walk-in closet along with convenient access to the full guest bathroom with tub and shower. Storage is abundant throughout the home with multiple interior closets, garage storage closets, and a spacious 2-car garage with laundry connections, helping keep everything neatly organized and out of sight. Additional features include an irrigation system and low-maintenance exterior living. Beyond the home, Cypresswood delivers one of Winter Haven’s most enjoyable golf community lifestyles. Residents enjoy access to the 18-hole championship golf course, originally opened in 1969 and designed by award-winning architect Ron Garl. Known for its rolling fairways and mature landscaping, the course also features a pro shop, driving range, putting green, and dedicated short-game practice areas. Just a short stroll from the home, residents can enjoy the recently refurbished junior Olympic-sized swimming pool, tennis courts, pickleball courts, and Wellness Center. The Cypresswood Pub & Restaurant serves as the social heart of the community, offering planned events, a full bar, great food, and live weekend music in a relaxed setting overlooking the golf course. Whether you are searching for a full-time residence, winter retreat, or low-maintenance golf community home, 460 Pinehurst Ct offers an exceptional opportunity to enjoy the Florida lifestyle in one of Winter Haven’s most established gated golf communities.

Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)

Listing Agent: Michael Stone (863-412-9733)

Remarks: Under contract-accepting backup offers. Just REDUCED!! Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the highly sought-after Cypresswood golf community in Winter Haven. Enjoy resort-style living with an 18-hole golf course, 24-hour gated security, clubhouse, community pool, and more. Inside, the renovated kitchen features granite countertops and custom cabinetry. The spacious primary suite offers a large ensuite bath complete with a double vanity and a generous walk-in closet. Additional updates include a roof replaced in July 2022, windows in May 2023, appliances in November 2016, an updated water heater and A/C, a garage screen added in September 2019, and a motorized awning installed in July 2022. This is an exceptional opportunity to own in one of Winter Haven’s premier neighborhoods. The home does come with appliances and washer and dryer.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)

Listing Agent: Melissa Witter (863-206-8744)

Remarks: MOVE-IN CONDITION! Charming 2-bedroom, 2-bath patio home on a shaded, landscaped corner lot in Cypresswood Golf & Country Club. This well-maintained single-level residence features a split-bedroom floorplan, expansive great room for living and dining, breakfast nook, carpet and tile floors, skylight, ceiling fans, ample closets including a walk-in in the primary, and a convenient attached 2-car garage with attic access. Enjoy an oversized screened rear porch overlooking picturesque greenspace and mature oaks. Systems and amenities include architectural shingle roof, gas water heater, and full kitchen appliances (dishwasher, range, microwave, refrigerator, washer/dryer). HOA includes community pool and private road; community amenities include an 18-hole golf course, clubhouse with pro shop and lounge, Jr. Olympic pool, tennis/pickleball/recreation area. Convenient to HWY 27, I-4, shopping, restaurants and near Publix.

Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)

Listing Agent: Michelle Howard (863-944-9920)

Remarks: Charming and Affordable 2/2 Block Home in Cypresswood Golf Community Discover comfort and convenience in this beautifully maintained 2 bedroom, 2 bathroom split floor plan block home located in the highly desirable Cypresswood Golf Community. This inviting residence offers a bright, open layout with spacious living areas and large walk-in closets in both bedrooms, providing plenty of storage space. Enjoy the ease of a 2-car garage, a well-designed kitchen, and peaceful views from your private patio. The split floor plan ensures added privacy, making it ideal for guests or a home office setup. Nestled within the scenic Cypresswood community, residents can enjoy beautifully landscaped surroundings, 24-hour gated security, and convenient access to golf, dining, shopping, and major roadways. This home offers the perfect blend of affordability, comfort, and resort-style Florida living.

Listing is courtesy of: THE MARKET REALTY COMPANY (863-999-4643)

Listing Agent: Vikki Thielen (863-604-6627)

Remarks: BRAND NEW ROOF INSTALLED NOVEMBER, 2025. Enjoy the Florida Country Club Lifestyle in this 2 bedroom patio home featuring a foyer with wet bar, spacious living room, dining area, kitchen with wood cabinets and converted Florida room, ideal as a den, office or play room. Additional amenities include an expansive master bedroom, 2 car garage with door opener and front courtyard wall. The home is in move-in condition but does have some original features and it's priced accordingly. This is an ideal opportunity to make this home your own with some contemporary updates. The home is currently tenant occupied on a month to month rental but the tenant may be willing to stay on for an investor purchase. Tenant has been there for 3 years.

Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)

Listing Agent: Steven Smith, Pa (863-224-2297)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Below Market Value—Golf Course Property, Seller Wants Offers Now Below-market golf course opportunity with motivated sellers—bring all offers for this value-add property on the 11th fairway. This 3-bedroom, 2-bath home features cathedral ceilings, a gas fireplace, and an open layout with excellent potential. The property is priced to reflect needed personal updates and is ideal for an investor, fix-and-flip, or buyer looking to build instant equity in a desirable golf course setting. Sellers are extremely motivated and will consider all offers. Opportunities like this at this price point do not last.

Listing is courtesy of: FAITH AND FAMILY REALTY LLC (863-712-1991)

Listing Agent: Lynn Arthur (336-596-5547)

Remarks: Now is your chance! Come and be a part of this active, Golf Course community and live in this beautifully maintained, updated home. Enjoy the peaceful screened courtyard with your cup of coffee, or watch the gorgeous Florida sunsets. The inside of the home has been lovingly kept up and updated. You won't want for space in this well thought out layout. Plenty of room for entertaining, or a quiet read alone. The garage has been set up for your perfect workspace or storage, whatever suits your needs. You have unlimited options with the screen garage door and a mini split that keeps everything cool when you need it! This golf course community is gated with a guard 24/7. Even if you don't golf, there will be something for you to do. Jr Olympic size pool, tennis courts, soon to be pickleball courts and a full service clubhouse with live music every weekend. Enjoy peace of mind knowing that the AC is less than a year old and the roof was replaced in 2022! Schedule your viewing today and welcome home!

Listing is courtesy of: REMAX EXPERTS (863-802-5262)

Listing Agent: Stacy Tuttle (863-602-9554)