Cypresswood Golf & Country Club
Championship golf community with resort amenities and active lifestyle in Winter Haven.
Live the MaxLife.
$289K
Median Price
$160K – $500K
1,062
Homes
$116–$1824
Monthly HOA
1974
Established
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Background
A brief history
Cypresswood Golf & Country Club was established in 1974 with a championship 18-hole golf course designed by renowned golf architect Ron Garl. The golf course has become a landmark in Central Florida, winning the 2023 Best of Haven award for Best Golf Course in Winter Haven. The community grew from the original golf course into a comprehensive 600-acre master-planned development featuring estate homes, villas, patio homes, and condominiums. What began as a single-use golf facility evolved into a vibrant residential community while maintaining the integrity of the original golf course and clubhouse operations.
The developer originally leased the golf course to the homeowners association for one dollar per year over a 50-year period, creating a unique partnership that allowed the community to grow while preserving the championship course. Today, the Cypresswood Community Association manages the golf course and all common areas, ensuring that the community's character and amenities remain a priority for all residents.
The feel
What it's like to live here
Cypresswood Golf & Country Club is an exclusive, established master-planned community that caters to active adults and golf enthusiasts. The community blends resort-style living with residential permanence, offering residents a clubhouse with restaurant and lounge, championship fairways, and comprehensive recreational facilities. The atmosphere is one of understated elegance—manicured landscaping, mature trees, and the constant presence of the golf course create a peaceful, refined environment.
Residents enjoy a strong sense of community fostered by the shared love of golf and outdoor recreation. The 24-hour security, well-maintained grounds, and extensive amenities create a safe, cohesive neighborhood. Whether residents are active golfers or simply drawn to the lifestyle and amenities, Cypresswood offers a full recreation and social calendar. The community appeals to both retirees seeking an active lifestyle and younger homeowners looking for the golf-course living experience.
The details
What to expect
Architecture & Homes
Cypresswood's architecture spans three decades and multiple housing types. Estate homes are traditional Florida architecture—stucco, tile roofs, screened lanais—ranging from 2,500 to 6,500+ square feet. Villas offer maintenance-free living with consistent design and HOA management. Patio homes and condos provide the most affordable entry point, typically 1,000–2,500 square feet with shared common areas. Newer homes feature updated finishes; older estate homes are charming but may need cosmetic updates. Golf-course-facing properties are highly sought and command price premiums.
Amenities & Lifestyle
The centerpiece is the championship 18-hole golf course (par 72) with a full pro shop and instruction programs. Beyond golf, the community offers a junior Olympic-sized swimming pool, six lighted tennis courts, pickleball courts, racquetball, basketball court, and a comprehensive wellness center. The clubhouse includes a restaurant and lounge, hosting regular social events, tournaments, and dining for residents and members. 24-hour security and gated entries ensure a safe environment. The community calendar is active year-round with golf tournaments, social gatherings, and fitness classes.
Schools
Cypresswood is located in Polk County and served by Winter Haven public schools. The specific school assignments depend on the exact address within the community, as some sections may be zoned to different elementary and middle schools. High school students typically attend schools in the Winter Haven district. Families should verify school assignments directly with Polk County Schools, as boundaries can vary even within the same neighborhood. The community is popular with retirees, so school quality may be less of a factor for many residents.
Location & Access
Cypresswood is centrally located in Winter Haven, just off US 17/92, providing easy access to Orlando (45 minutes north), Tampa (50 minutes west), and the Gulf Coast beaches (90 minutes southwest). The community is surrounded by local shopping, dining, and services. Polk County's extensive trail systems and parks provide outdoor recreation options beyond the community. The location balances a quiet, country-club atmosphere with proximity to major employment centers and urban amenities. Winter Haven's growing economy and proximity to I-4 make it increasingly attractive to both retirees and working professionals.
Community
Amenities
- Championship 18-hole golf course (par 72)
- Golf pro shop with instruction
- Clubhouse with restaurant and lounge
- Junior Olympic-sized swimming pool
- Six lighted tennis courts
- Pickleball courts
- Racquetball court
- Basketball court
- Wellness / fitness center
- 24-hour manned security gates
- Maintained community roads
- Lush landscaping and grounds
- Social and tournament calendar
- Shuttle service for golf members
Know Before You Buy
HOA rules worth knowing
- Golf course is a major amenity; golf membership is optional but encouraged
- HOA fees cover security, grounds, utilities, common area maintenance, and recreation facility access
- Single-family homes must maintain exterior appearance per community guidelines
- Pets are permitted with size and breed restrictions; check with HOA for specifics
- Short-term rentals are restricted; verify current rental policy with HOA before purchasing
- All exterior modifications and landscaping changes require HOA approval
- Common area rules ensure the golf course and amenities remain in excellent condition
- Resale homes typically require HOA disclosure and transfer fees
- Gated community with 24-hour security; residents receive gate access cards
Market Commentary
What the market is doing
I've worked with dozens of Cypresswood sellers, and pricing strategy here comes down to understanding micro-location. Homes on or near the fairways command 10-15% premiums over standard lots—buyers are paying for the view and the lifestyle. Estate homes are pushing toward the $400K-$500K range, while patio homes and condos move faster in the $200K-$300K band. The $121/sqft average holds if you're priced right, but overpriced properties can sit. I always recommend starting aggressive but realistic, especially for non-golf-front homes. The HOA fee is transparent and well-understood by your buyer pool, so lead with it confidently.
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Homes available in Cypresswood Golf & Country Club
12 homes currently listed in Cypresswood Golf & Country Club.
$395,000
2852 San Marco Way
Winter Haven, FL 33884
4 bd · 2 ba · 2,066 sqft
Villamar Phase 6 And Phase 6d
MLS# L4962433
$447,500
496 Terranova St
Winter Haven, FL 33884
4 bd · 2 ba · 2,357 sqft
Terranova Ph 02
MLS# O6380041
$299,490
6228 Botticella Blvd
Winter Haven, FL 33884
5 bd · 3 ba · 2,326 sqft
Villa Mar 40'S
MLS# O6413726
$1,475 /mo
103 4th St Se #A
Winter Haven, FL 33880
2 bd · 1 ba · 1,014 sqft
Denison Heights Estates Rep Pt
MLS# K4903538
$180,000
2107 High Point Ave Sw
Winter Haven, FL 33880
3 bd · 1 ba · 1,014 sqft
High Point
MLS# O6411867
$304,999
6103 Grey Heron Dr
Winter Haven, FL 33881
4 bd · 2 ba · 1,828 sqft
Lakeside Landings Ph 01
MLS# O6403532
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Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of June 4, 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA