$324,126Average Value$172Average Price per Sq Ft46Homes 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 96 days on the market compared to the national average of 55 days. The median sale price for homes in Cypresswood, Winter Haven over the last 12 months is $290,000, up 1% from the median home sale price over the previous 12 months.
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 the affordable lifestyle of living in a Villa within a golf course community. Upon entering the front of the home you will notice a courtyard area on the left and right side of the entrance, which opens up additional outside entertaining space. Once inside the home you will notice it has recently been refreshed with new interior painting throughout, all new flooring, and new stove and
Welcome to 287 Inman Blvd—where modern comfort meets effortless Florida living in the heart of Winter Haven. This beautifully maintained home truly feels like new, offering the peace of mind of recent construction with thoughtful upgrades already in place. From the moment you step inside, you’ll notice a clean, contemporary design paired with warm, inviting spaces. The open-concept layout flows
Welcome to this charming 2-bedroom, 1-bath home in the growing city of Winter Haven. Situated on a .16-acre oversized lot, this property offers both comfort and opportunity. The home features a functional layout and a new AC installed in 2024, providing added efficiency and peace of mind. The spacious backyard includes a detached shed with great potential, perfect for a workshop, studio, storage,
Lot #360 / 3 B / 3 BA / 1,992 Sq. Ft. / $209,800.00 Beautiful Like New 2023 Home! Builder's Model Showpiece - 2023 Erica Model in popular Cypress Creek Village! This large, one-owner home is located on a pond lot! It has a glass window enclosed screen room overlooking a patio and pond beyond. Enter into the large open concept home and look across the large Living Room, Dining Room, and Kitchen.
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
CYPRESS CREEK VILLAGE #288 / 2 BED / 2 BATH / 1,000 SF / $80,000 Open Floor Plan with two bed/bath suites! This well maintained 2017 Nobility Home features an open floor plan and two large bedroom suites! The large living room and ample dining room adjoin a light filled kitchen with white cabinets. Vaulted ceilings add volume to the open space. The master bedroom has walk in closet. The guest
**Charming Waterfront Retreat in Florida!** NEW ROOF 2025! Discover your dream home with this stunning 2008 Fleetwood model that boasts breathtaking views of a serene lake. Imagine sipping your morning coffee while watching Florida's vibrant birds from your cozy dining area or spacious living room. This meticulously maintained residence features an inviting vinyl-windowed Florida room, perfectly
Tanya JohnstonAmerican Mobile Home Sales of Tampa Bay, Inc.
Enjoy peaceful living in this beautifully maintained Nobility Erica home, perfectly situated in desirable Cypress Creek Village with serene water views and ultimate privacy!- Step inside to a bright and spacious 17' x 15'5" living room, featuring gorgeous laminate wood flooring and a ceiling fan, flowing seamlessly into the open dining area-ideal for entertaining.- The 9' x 11'5" dining
Tanya JohnstonAmerican Mobile Home Sales of Tampa Bay, Inc.
Enjoy serene golf-front living in this beautifully designed 2BR/2BA home, featuring two versatile bonus rooms perfect for a media room, home office, or guest space. This home features an irrigation well for watering the beautiful landscaping, and inside, there is an emergency whole-home Generac generator system! There is also a nice gas fireplace in the living area. Located in a desirable
Lot #158 - 2 Bed / 2 Bath / 864 Sq. Ft. / $55,000 -- 2008 Cottage Style Home. This cozy - 2 bedroom, 2 bathroom home features 2 large bedroom ensuites at either end (for privacy) - with open living in the center. This one-owner home features a NEW ARCHITECTURAL SHINGLE ROOF! The owner specifically chose this special lot for its peaceful location and views of the oak trees and neighboring farm.
Lot #372 - 2 Bed / 2 Bath / 1,120 Sq. Ft. / $139,800.00 -- 2023 Builder's Model - Turnkey Home! Your retirement or seasonal home is all furnished, decorated, and ready for you! Just bring your clothes and enjoy. This STUNNING - 2 bedroom, 2 bathroom home features 2 large bedroom ensuites at either end (for privacy) - with open living in the center. Walk in closets are one of many luxury features.
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,
$2,089 per month
4 Beds
3 Baths
2,150 Sq Ft
Take a look at this beautiful home, Clean and Move-In Ready, featuring 4 bedrooms, _3 bathrooms, 2 car garage and approximately 2,150 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.95/mo; Washer/Dryer - $35/mo; High Speed Cable/Internet (if applicable by 3rd Party user) $55/mo; Renters insurance reqrd,
Coming soon - this home is currently being enjoyed by another resident but will be available soon. 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
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
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Beautiful 4-bedroom/3.5-bathroom home with additional bonus room ideal for an office, den, gym, or play room in the prestigious Woodpointe community of SE Winter Haven! Elegant custom and designer finishes throughout, screened lanai, walk-in closets, open-concept and split-bedroom floor plan, and so much more. Applications evaluated on creditworthiness and income equal to at least 3x monthly rent
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 happy to help you find a different home or refund your Hold Fee. This home
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
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
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
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
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
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