$328,203Average Value$170Average Price per Sq Ft55Homes 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.
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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.
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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.
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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.
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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.
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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
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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 89 days on the market compared to the national average of 53 days. The median sale price for homes in Cypresswood, Winter Haven over the last 12 months is $291,250, down 1% from the median home sale price over the previous 12 months.
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Special offer: Pay just $500 of your base rent (taxes and fees not included) as your security deposit, valid for new applicants who sign a 12-month lease by November 30, 2025. Offer is contingent on application approval and execution of a lease agreement. Other terms and conditions may apply. This property is professionally managed by AMH, a leading single-family rental company. We work to
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