$326,995Average Value$170Average Price per Sq Ft54Homes 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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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 93 days on the market compared to the national average of 54 days. The median sale price for homes in Cypresswood, Winter Haven over the last 12 months is $275,000, down 5% from the median home sale price over the previous 12 months.
Fresh new price — your opportunity to own in Cypresswood just got better! Welcome to 560 St Andrews Rd in Cypresswood Golf & Country Club!This beautiful patio home is truly move-in ready, offering 2 bedrooms, 2 bathrooms, and plenty of stylish updates.From the moment you arrive, you’ll be impressed by the brick-paver driveway, lush landscaping, and inviting curb appeal. Inside, the spacious
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
A beautiful family home is now available in the desirable gated community of Crossroads at Lake Region. This 4-bedroom, 3-bath property feels like new. The welcoming covered entry features 8-foot glass doors with sidelights that fill the space with natural light and open into the foyer, great room, and kitchen area with impressive 13' ceilings. The well-designed 3-way split floor plan offers
PRICE ADJUSTMENT ALERT—the opportunity you've been waiting for! Welcome to easy, low-maintenance living in the 24/7 guard-gated Cypresswood Golf & Country Club. This charming condo offers peaceful POND VIEWS from the living room and both bedrooms, creating the perfect backdrop for relaxing mornings and quiet evenings.Inside, you'll love the bright, open layout with 10' ceilings, rich wood
Short Sale. BANKRUPTCY SHORT SALE! Located In The Country Walk Community, This 2019 Built Home At 3180 Country Club Cir, Winter Haven, FL 33881 Features The Popular DR Horton Aria Floor Plan Offering 3 Bedrooms, 2 Bathrooms, & 1,672 Sq Ft Of Living Space. This Home Offers an Open Concept Layout With A Spacious Living Area, Split Bedroom Floor Plan, & a Functional Kitchen Overlooking The Main
Wake up to golf course views along the 8th fairway in this single-owner Cypresswood golf villa — a lovingly maintained home offering flexible space to personalize and a rare opportunity to create your ideal Florida retreat in one of Winter Haven’s premier guard-gated communities. Vaulted ceilings open the living and dining areas, while the kitchen offers generous cabinetry and flows into a bright
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 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! 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 wait. Step inside and be greeted by a bright and open first floor layout
CORNER LOT! PRISTINE! MOVE IN READY! Come see this Pristine 3 BED 2 BATH home. in a solar-friendly community. Built in 2023 this home offers peaceful views, unbeatable privacy, and all the advantages of brand-new construction—without the wait. Welcome to this bright, open-concept home designed for easy living and entertaining. Features a modern kitchen with quartz countertops, stainless steel
Welcome to this beautifully proportioned two-story home offering over 2600 square feet of comfortable living space. Featuring 4 bedrooms and 2.5 baths, this home is designed for both everyday living and entertaining. The main level boasts an extra-large eat-in kitchen with ample space for family meals and gatherings, flowing seamlessly into generous living areas. Upstairs, all four bedrooms are
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
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!
Lot #256 - 2 Bed /2 Bath + Den /1,568 Sq. Ft./$148,900.00 Spectacular Pond Views from this 2016 Ashley Model in beautiful Cypress Creek Village! This spacious home is located on a waterfront lot with breathtaking views! It offers a double carport with an additional golf cart path! This gorgeous home offers: *Vaulted Ceilings *Kitchen with coffee station and pantry *French doors into large den
Please note that the advertised price may exclude additional fees. These include a $55 application fee per applicant; a one-time $75 admin fee; a $11 monthly utility management fee; other mandatory fees, if applicable, for pool maintenance, pet fees/rent, smart home, internet service, and propane refilling; and optional fees for services like self-guided tours with third-party provider Rently
Affordability meets Comfort. Second Floor unit for privacy 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, trash service, exterior pest control, and private road upkeep. Residents can also enjoy an 18-hole golf course, on-site restaurant, swimming pool, tennis courts,
Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month’s rent. Pet fees: $250 + $35/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.
This beautiful GROUND FLOOR Eagle Pond condominium has been is located in the highly desirable 24-hour guard-gated community of Cypresswood Golf and Country Club. This meticulously-maintained condo features tile floors throughout, upgraded light fixtures, interior laundry, granite surfaces in the kitchen and baths, and so much more. Entertain friends and family around the rennovated kitchen that
We are currently making final preparations for this home to be available. We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be
Modern 4-Bedroom Home for Rent – Winter Haven, FLWelcome to 724 Grove Street, Winter Haven, FL 33881, a beautiful single-story home built in 2023 and located in the desirable Inman Groves Phase 2 community. This spacious residence offers 4 bedrooms, 2 bathrooms, and 1,848 sq ft of comfortable living space with a modern, open layout designed for everyday convenience. Property
Nestled in the serene location of Winter Haven; beautiful house conveniently located near Lego Land. 5 bedrooms, 3 bathrooms, 2-car garage, stainless steel appliances. Fenced-in backyard offering space and privacy. Includes smart home technology so that you can connect to your home via smartphone. Enjoy Winter Haven's main attractions and sights such as boating on the Chain of Lakes and Antique
Super Cute Home features 4 bedroom, 2 bath, 2 car garage home, located in Country Club Estates. Freshly painted a neutral color, tile in living areas and brand new LVP in bedroom. Living room kitchen combo, great for gatherings. Call today for a showing!
GROUND FLOOR Eagle Pond condominium in the highly desirable gated community of Cypresswood Golf and Country Club. This professionally-managed condominium has just been partially renovated to include luxury vinyl flooring and fresh paint throughout. Key features are interior laundry, walk-in closets, open concept living space, and so much more. The spacious master bedroom features an en suite
Gorgeous 3BR/2BA Home - AVAILABLE FOR APRIL Looking for a hassle-free rental? This beautifully furnished 3-bedroom, 2-bathroom home in Winter Haven is move-in ready! Just unpack and start living. Features You\'ll Love:-Modern Kitchen - Stainless steel appliances & tons of counter space.-Washer & Dryer In-Unit - Laundry made easy.-Attached Garage - Convenient parking & extra
Welcome to this beautiful and spacious 2 bedroom 2 bath second floor condo overlooking the pond in Cyprewood. 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 center. Conveniently
One or more photo(s) has been virtually staged. Available for immediate move-in! Check out this charming 2-bedroom, 2-bath home located in the Gates of Lake Region gated community. Positioned just inside the neighborhood, this property offers immediate convenience and a serene setting with a sparkling pond right outside your screened in lanai. Inside, the home features warm wood flooring
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