$324,063Average Value$169Average Price per Sq Ft50Homes For Sale
Living on the greens of Cypresswood
Cypresswood is a master-planned community where golf courses and country clubs offer luxury, convenience and amenities. With over 1,000 residential units and 14 neighborhood associations within Cypresswood Community Association, the area has plenty of housing options for various preferences. The main golf course, which opened in 1969 and was voted the best course in Winter Haven for 2023, is owned by the Cypresswood Community Association. “The developer wanted it to stay a golf course, so he leased it to the homeowner’s association for one dollar a year for the next 50 years,” says Tom Hevel, Assistant Golf Professional at Cypresswood Golf & Country Club. “I imagine if it’s a golf course for all that time, it’ll be a golf course forever.” Residents here not only have access to country club amenities, but also to shopping, dining and education nearby. Cypresswood students are zoned for Polk County Public Schools, which is in the top 50 districts in the state, according to Niche.
Cypresswood is a master-planned community where golf courses and country clubs meet.
The Cypresswood community is an exclusive, master planned community located in Winter Haven.
1/2
Cypresswood golf, trails and nearby amusement parks
While most residents here spend outdoor time on the golf course, in the pool or at the gym at the Cypresswood Golf & Country Club or at The Country Club of Winter Haven, other public parks are available nearby. Locals can get some fresh air at the Michael V. Lewis Arboretum and Parrott Trail, where 42 acres of land host a mixture of native and exotic plants. The trail is about 1.5 miles and features picnic shelters and the personal plant collection of Talbot Lewis, who took decades to landscape the area. For fishing enthusiasts, there are plenty of lakes nearby, though some are private and prohibit public recreation. Cypresswood is also under 5 miles from Legoland, and under 30 minutes from Disney World. The neighborhood sits about 2 hours from both east and west coast beaches.
Cypresswood Golf Course is an award winning course designed by local architect Ron Carl.
Enjoy a tranquil walk on the trails under the lush canopy at the Micheal V Lewis Arboretum.
With Legoland a short 5 minutes from Cypresswood, the fun awaits you at the turstyles.
1/3
Shopping at Winn-Dixie and dining at Cypresswood Pub
The main restaurant in the area is Cypresswood Golf & Country Club’s restaurant, the Cypresswood Pub, though residents travel outside of the neighborhood for more options. “Folks around here ride their golf carts everywhere,” Hevel says. “There’s a little strip mall nearby with a sandwich shop and a dollar store. People go there all the time.” Cypresswood is a short drive to Legacy Craft BBQ, which serves slow-smoked Southern BBQ, handmade sauces and fresh pies and cobblers. The Dundee Diner is another popular spot, known for its homestyle cooking. For groceries, Winn-Dixie is within 2 miles of the neighborhood, and a Walmart Supercenter is under 6 miles south.
Residents of Cypresswood can find all their supplies and groceries at the local Winn-Dixie.
Cypress Creek Plaza offers a great assortment of food options for residents of Cypresswood.
Residents of Cypresswood frequent the Dundee Diner for the best breakfast in town.
1/3
When not out on the golf course members take each other on in a game of tennis at the WHCC.
Special Cypresswood events
The neighborhood has plenty of activities throughout the year to keep the community close. The Cypresswood Social group works to improve the events and opportunities in the area and is currently working to convert some tennis courts into pickleball courts. The Cypresswood Pub has live music on the weekends, yappy hours for the four-legged residents and corn hole. The country clubs hold special activities, as well, including tennis clinics and community service events, including blood drives.
Ranch-style architecture in Cypresswood
Most homes here were constructed in the 1980s to early 2000s and bear ranch-style architecture. New construction is still popping up today, including custom builds on sprawling lots. Properties often sell between $200,000 and $600,000, with outliers on both ends of the range. Price not only depends on home size, but also location on the course. “I’d say about 70% of people just move here because they like the house they find, and 30% are here for the golf,” says Hevel. Houses often have two- or three-car garages and green lawns shaded by palm trees, and some have private pools in enclosures that protect the area from bugs and severe sunlight.
Cypresswood is known for it larger lots and lush green lawns.
In Cypresswood larger ranch homes with pristine landscaping can be seen in many subdivisions.
1/2
Education opportunities near Cypresswood
Students in the Cypresswood neighborhood can begin their education at Elbert Elementary and Denison Middle, which both earn C grades on Niche. Winter Haven Senior High School earns a B-minus rating and is part of the Advanced International Certificate of Education program (A.I.C.E.) through the University of Cambridge. For a private pre-kindergarten through 12th grade option, Winter Haven Christian School is within a few miles of most residences for faith-based learning.
Garden Grove serves over 600 students in grades VPK-5th.
Denison Middle School is home to over 800 students in grades 6-8.
Winter Haven Senior High School is a public school located in Winter Haven, FL.
1/3
Major routes are nearby, such as US Highway 27, which flows north for easy access to I-4.
Transportation in Cypresswood
Public transportation does not reach the neighborhood, and Cypresswood residents usually get around by car or golf cart. Major routes are nearby, such as US Highway 27, which flows north toward Gainesville. Florida State Road 60, from Tampa to the east coast, is within 15 miles, which is a 20-minute drive from Cypresswood. For air travel, Orlando International is about 45 miles away. Other amenities, such as health care and houses of worship are typically found toward the west in Winter Haven, within about 6 miles.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
Are you familiar with the Cypresswood neighborhood?
to let others know what life in this neighborhood is like.
Crime and Safety
1 - Low Crime, 10 - High Crime
Cypresswood
US
Homicide
1
4
Sexual Assault
3
4
Assault with Weapon
3
4
Robbery
3
4
Burglary
4
4
Motor Vehicle Theft
4
4
Larceny
3
4
Crime Score
3
4
Source: WhatIsMyCrimeRisk.com
Cypresswood Demographics and Home Trends
On average, homes in Cypresswood, Winter Haven sell after 101 days on the market compared to the national average of 58 days. The median sale price for homes in Cypresswood, Winter Haven over the last 12 months is $286,650, down 1% from the median home sale price over the previous 12 months.
Need 4 bedrooms, but don't need to break the budget? This is what you've been searching for here in the heart of Winter Haven! Situated perfectly W of Hwy 27 and out of the hustle and bustle of the city, this 4/2/2 home is ready for you! Close to houses of worship, schools, shopping, golf, and SO much more! Upon arrival, you note the quaint neighborhood, which quickly says "community." The home
Opportunities like this are nearly extinct. Just minutes from Winter Haven Country Club, this remarkable estate offers 10.98 acres of privacy, natural beauty, and flexibility in one of Winter Haven’s most coveted and tightly held locations—where land, space, and convenience rarely coexist.The 3,800 sq ft main residence has been completely remodeled with a refined, modern vision that blends
Welcome to 814 Turner Lane, a beautifully upgraded Hayden model by D.R. Horton located in the heart of Winter Haven! ?? This spacious two-story home offers 5 bedrooms, 3 full bathrooms, and over 2,500 sq. ft. of living space, making it the perfect choice for families or anyone seeking extra room to spread out. Built with quality craftsmanship and thoughtful design, the Hayden model is known for
WELCOME HOME to this beautifully updated 3-bedroom, 2-bath residence located in the pristine gated community of Cypresswood! From the moment you enter the neighborhood, you’ll feel the charm of this private, resort-style community nestled in the heart of Polk County—just minutes from US Hwy 27, providing easy access to all that Central Florida has to offer.Step through the front door into a
Michelle KeohaneINFINITE REAL ESTATE POWERED BY ILIST
One or more photo(s) has been virtually staged. Welcome to 3228 Country Walk Club Cir in Winter Haven! This spacious two-story home features 5 bedrooms and 3 bathrooms, offering plenty of room for family and entertaining. The home has been updated with fresh interior paint, brand-new carpet and vinyl flooring throughout, and modern lighting fixtures. The kitchen comes equipped with new stainless
Located in the highly sought-after gated golf community of Cypresswood in Winter Haven, this beautiful 4-bedroom, 3-bathroom home offers over 2,800 square feet of spacious living when pool room footage is added. The offering includes a private pool, and a 9x9 pool house complete with a half bath, perfect for guests, poolside entertaining, or an additional flex space. Inside, the home boasts a
Welcome to this beautifully updated 3-bedroom, 2-bathroom home offering 1,344 square feet of comfortable living in the sought-after 55+ community of Cypress Creek Village in Winter Haven. Built in 2020, this residence is move-in ready and designed for relaxed Florida living. The home features well-manicured landscaping that enhances its curb appeal, along with low-maintenance vinyl siding, a
PRISTINE AND MOVE-IN READY! Seller is offering up to $5,000 concession towards closing costs and prepaids. Come and see this barely lived in 5 BEDROOM, 2.5-BATH home nestled in the solar-friendly community of INMAN GROVES. Built in 2024 and set on a corner lot with NO REAR NEIGHBORS, this home offers peaceful views, unbeatable privacy, and all the advantages of brand-new construction—without the
Be the first to own this stunning 2024-built semi-custom home located in the gated, lakefront community of Woodpointe in Winter Haven’s desirable 33884 zip code. Thoughtfully designed with both comfort and functionality in mind, this spacious residence features 4 bedrooms, 3.5 bathrooms, and an incredibly smart split-bedroom floorplan that offers privacy and flexibility for modern living. The
Positioned along highly traveled Dundee Road, this prime commercial lot presents a rare, turnkey development opportunity in a growing Central Florida corridor. The property has already completed the state permitting process, significantly reducing timelines and uncertainty for a new owner or developer. With an approved driveway in place and site plans already prepared for a hotel, much of the
CYPRESS CREEK VILLAGE #61 / 2 BED / 2 BATH / 1,344 SF / $98,800 POND VIEW HOME with Double Driveway! This Large WELL MAINTAINED updated home is partially furnished and move-in-ready for you! This 2006 Nobility Home features an open floor plan and large two-level lanai overlooking a pond! Lanai includes tile floors, vinyl windows, roman shades, and a covered patio that is perfect for grilling out!
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
Property Id: 1287192Modern 4BR 2 Baths in Winter Haven | Lawn Care IncludedEnjoy stress-free living in this spacious 4-bed, 2-bath home (built in 2019) on an oversized lot. This property blends high-end finishes with ultimate convenience.Home Highlights:*Kitchen: Granite countertops and stainless steel appliances.*Premium Flooring: Durable tile throughout; plush
This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 2,136 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a Tricon resident, you'll enjoy access to Tricon Vantage — a program designed to support your rental
Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is
Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening!Take advantage of the incredible location,
This beautiful 3-bedroom, 2-bathroom home is nestled in the sought-after Whispering Trails neighborhood of Winter Haven. Inside, you’ll find an open floor plan that creates a bright, airy flow from the living area to the kitchen and dining space—perfect for both everyday living and entertaining. The home comes equipped with a washer and dryer, making move-in easy and convenient. Step outside to
Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service and maintenance, innovative resident programs, and more… that's the power of purple!This 4-bedroom, 2.5-bathroom rental home in Winter Haven, FL, might be the perfect fit for your lifestyle.
Affordability meets Comfort. First Floor unit for easy access in a highly desirable gated community of Cypresswood Golf & Country Club. This rental will include access to community pool, 24-hour security, exterior maintenance, common area taxes, trash service, pest control, and private road upkeep. Residents can also enjoy an 18-hole golf course, on-site restaurant, tennis courts, and a fitness
2 BED/2 BATH PATIO HOME IN CYPRESSWOOD! Massive living space, well-sized rooms, open kitchen, hardwood flooring throughout, an enclosed front patio, brand new appliances (including a refrigerator which isn't pictured), attached 2 car garage, and a Florida room with attached outdoor patio overlooking the championship Cypresswood Golf Course. Located in the gated community of Cypresswood, you'll
This cozy and well-maintained home offers a warm and inviting layout, ideal for comfortable and easy living. The property features a functional floor plan with a modern kitchen, bright and spacious bedrooms, and low-maintenance living areas designed for convenience. Centrally located with quick access to US-27, US-17, SR-540, and I-4, this home provides easy commutes to Orlando and Tampa, as well
Jenny CasoLIFESTYLE INTERNATIONAL REALTY
$2,025 per month
Spacious 4-Bedroom Home with 3 Full Baths in Whispering Trails – Pet Friendly!
Welcome to this beautiful and spacious 4-bedroom, 3-bathroom home located in the desirable Whispering Trails community in Winter Haven. With over 2,100 square feet of living space, this home offers a perfect blend of comfort and functionality.The thoughtfully designed layout provides ample space for both relaxing and entertaining, featuring generous living areas, well-sized bedrooms, and
Amazing location! In this beautiful house you will find a 3 bedroom 2 full bath and a bonus room (use it as an extra bedroom, office, etc.) This modern house sits on a corner lot, spacious living area, very sunny and inviting, ceramic tiles, stainless steal appliances, quartz counter tops, walking closet and a 2 car garage. Call to schedule a showing and move in to this lovely community.
Britzeida PichardoLA ROSA REALTY CENTRAL FLORIDA LLC
MOVE-IN READY upstairs Eagle Pond condominium in the highly desirable gated community of Cypresswood Golf and Country Club. This professionally-managed condominium includes interior laundry, walk-in closets, open concept living space, and so much more. The spacious master bedroom features an en suite bathroom while both bedrooms offer walk-in closets. Additional linen storage exists in the main
Local Logic measures the walkability, access to public transit and bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
