Cypress Head Port Orange FL — Golf Course Community Guide | Robert Wrieden
HomePort Orange FL Homes for Sale › Cypress Head
Port Orange, FL 32128 · Golf Course Community

Cypress Head Port Orange — Golf Course Living in Central Florida

Port Orange's premier golf community — an Arthur Hills-designed public course, pool, tennis, top-rated schools, and homes starting in the $300s. Five miles from the beach.

By Robert Wrieden, REALTOR® SL3638019  ·  Summer Wind Realty Central Florida  ·  Updated June 2026

Schedule a Showing View Current Listings ↓
$300K+
Homes from
18
Hole public course
5 mi
To the beach
6,805
Yards · Par 72
1992
Community established
Listings Overview Golf Course Amenities HOA FAQ Contact

Cypress Head Homes for Sale

🏡 Cypress Head Active Listings

Add your Showcase IDX hotsheet shortcode here — filter by subdivision "Cypress Head" in Port Orange, Volusia County.

[showcase_idx_hotsheet subdivision="Cypress Head" city="Port Orange" state="FL"]

Search All Port Orange Homes →

About Cypress Head Port Orange

Cypress Head sits in the southwest corner of Port Orange, FL 32128 — one of Volusia County's most consistently sought-after residential communities. Built primarily in the 1990s and early 2000s by Paytas Homes, the neighborhood wraps around the fairways of Cypress Head Golf Club, a municipally-owned Arthur Hills design that ranks among the top public courses in Central Florida.

What makes Cypress Head stand out in the Port Orange market isn't just the golf. It's the combination of factors that's hard to find at this price point: top-rated Volusia County schools within walking distance, a community pool and tennis courts maintained by the HOA, preserved wetlands and lake views on nearly every street, and a five-mile drive to the Atlantic coast. Homes range from split-plan townhomes in the $300s to larger estate homes on golf course lots pushing $600K+.

The community draws a genuine mix — retiring couples who want to walk to the first tee in the morning, families attracted by the schools and the space, and professionals who want suburban quality without sacrificing proximity to Daytona Beach and I-95. NeighborhoodScout ranks Cypress Head among the top 2% of family-friendly neighborhoods in all of Florida, and one of the lowest childhood poverty rates of any neighborhood in the United States.

Location note for relocation buyers: Cypress Head is about 10 miles from the Daytona Beach International Airport, 15 miles north of New Smyrna Beach, and under an hour from Orlando via I-4. It's genuinely convenient without feeling like a suburb of anything — Port Orange has its own complete commercial infrastructure and identity.

Cypress Head Golf Club

An Arthur Hills Design — Open to the Public

Cypress Head Golf Club is a municipal course owned by the City of Port Orange and managed by KemperSports. That means it's open to everyone, not just residents — but living here means walking or a two-minute drive to one of the most acclaimed public courses in Volusia County.

Designed by Arthur Hills and Mike Dasher (renovated 2015), the course plays 6,805 yards from the tournament tees with a rating of 72.9 and a slope of 139. Water comes into play on 14 of 18 holes. The two nines play distinctly differently — the front nine is considered the highlight, with varied hole shapes, multi-tiered greens, and preserved wetlands creating genuine strategic challenge.

Proper golf attire required. Rental clubs available. For tee times: (386) 756-5449 or cypressheadgolf.com.

6,805
Yards
72
Par
72.9
Course rating
139
Slope
14/18
Holes with water
Public
Open to all

The Flagsticks Bar & Grill at the clubhouse overlooks the course and serves sandwiches, burgers, and drinks — a natural gathering spot for residents whether they play or not. The driving range is also available for practice.


What's Included at Cypress Head

Golf Course

18-hole Arthur Hills design — public municipal course ranked among the best in Central Florida

🏊

Community Pool

HOA-maintained swimming pool available to all Cypress Head residents

🎾

Tennis & Pickleball

Courts on site — residents active in organized play and recreational committees

🏛️

Clubhouse

Community clubhouse for recreation, events, and HOA board meetings held monthly

🏌️

Driving Range

Practice facility at Cypress Head Golf Club — accessible without a full round

🌿

Preserved Wetlands

Expansive natural preservation areas with lake views throughout the community

Nearby — Within 5 Miles

🛒

Westport Plaza — Publix

Within 5 miles — grocery, pharmacy, everyday services

🎬

The Pavilion at Port Orange

~10 min — movie theater, Marshalls, HomeGoods, Petco, Saturday farmers market

🍽️

Venetian Bay — Bistro 424

Nearby mixed-use town center — family-owned market, restaurants, live music Saturdays

🏖️

Wilbur Beach & New Smyrna Inlet

~5 miles south — less crowded than Daytona, popular for kayaking and paddleboarding

🚤

Riverwalk Park — Boat Launch

Carefree Boat Club of Port Orange — rentals and Halifax River access

🏫

Top-Rated Schools

Elem. and middle schools within walking distance — among the best in Volusia County


Cypress Head HOA Details

Item Details
HOA NameCypress Head HOA (multiple sub-associations by section)
Management — MainTout Management · office@toutmgmt.com
Management — Golf VillasSouth Atlantic Communities
Management — The LakesTLC Professional Group, LLC
ARC Contactarc.cypresshead@gmail.com
Board MeetingsMonthly at the Clubhouse — open to residents
Estoppel Formsashley@toutmgmt.com
Gated SectionsTwo gated sections with larger estate homes
Deed RestrictionsPUD agreement — CC&Rs require front yard shrub maintenance; ARC approval required for exterior changes
Golf Course OwnershipCity of Port Orange — municipally owned, managed by KemperSports
HOA FeesVerify current fees with listing agent — varies by section
ARC note: The Architectural Review Committee requires written approval before any exterior modifications, landscaping changes, or replanting. Submit an ARC Request with a landscaping plan before work begins. ARC approval must be received before Port Orange permitting. Contact arc.cypresshead@gmail.com for current forms.

Cypress Head FAQ

What are homes in Cypress Head selling for in 2026?
Cypress Head homes have been selling in the $300,000–$600,000+ range depending on size, lot position, and whether the home is on the golf course or a lake lot. The median sale price for the community over the past year has been approximately $450,000, up modestly from the prior year. Golf course-facing lots and homes with pool additions command the upper end. Townhomes and smaller split-plan homes are the most accessible entry point, typically in the $300,000–$380,000 range. Average days on market has been around 83 days, giving buyers reasonable time to evaluate without the pressure of the 2021–2023 market. Robert can run a current comparable sales analysis for any specific section of the community before you make an offer.
Is the golf course private or can anyone play?
Cypress Head Golf Club is a public, municipally-owned course — anyone can play, not just residents. It's owned by the City of Port Orange and managed by KemperSports. This is one of the community's genuine selling points: you get the lifestyle benefits of living on a golf course without paying private club membership fees. Green fees are very reasonable by Central Florida standards. For tee times, call (386) 756-5449 or visit cypressheadgolf.com. Proper golf attire is required, and outside alcohol is not permitted per Florida law.
How are the schools near Cypress Head?
Cypress Head feeds into some of the strongest schools in Volusia County. Elementary and middle schools are within walking distance of the community. NeighborhoodScout ranks Cypress Head among the top 2% of family-friendly neighborhoods in Florida, and notes that the high concentration of college-educated households has a measurable positive influence on local school performance. Port Orange consistently outperforms many other Volusia County municipalities on school quality metrics. If specific school assignments are important to your decision, Robert can verify current zoning before you make an offer — school boundaries occasionally shift with district redistricting.
How far is Cypress Head from the beach?
About five miles — a 10-minute drive under normal conditions. Wilbur Beach and the New Smyrna Beach Inlet to the south are the closest options and tend to be less crowded than Daytona Beach to the north, which is about 15 miles away. Residents who want beach access without beach-adjacent pricing consistently cite this as one of Cypress Head's advantages. The Riverwalk Park boat launch is also nearby for Halifax River and intercoastal access.
Are there different HOA sections within Cypress Head?
Yes — Cypress Head is a planned unit development (PUD) with multiple sub-associations managed by different companies. The Golf Villas section is managed by South Atlantic Communities. The Lakes section is managed by TLC Professional Group. The main HOA is managed by Tout Management. Two gated sections with larger estate homes exist within the overall community. When evaluating a specific home, confirm which HOA section it falls under, what the current monthly dues are, and what is and isn't included. Robert pulls this detail as part of standard due diligence on any Cypress Head offer.
What kind of commute does Cypress Head have?
Port Orange is well-served by I-95 and US-1 for north-south travel, and I-4 for east-west to Orlando. For local commuters in the Daytona Beach metro area, Cypress Head is convenient to most employment centers. One thing to be aware of: NeighborhoodScout data shows a segment of Cypress Head residents have longer commutes — about 17% travel more than an hour each way — which typically reflects residents who commute to Orlando or Jacksonville while living in Port Orange for the quality of life and price point. If you're working locally in Daytona Beach, Port Orange, or Ormond Beach, the commute is entirely manageable.
What type of homes are in Cypress Head?
Cypress Head is primarily single-family homes ranging from 3–5+ bedrooms, with a smaller number of townhomes concentrated near the Golf Villas section. Most homes were built between 1992 and the mid-2000s by Paytas Homes, with split floor plans typically under 2,000 square feet at the smaller end and larger estate homes on golf course lots exceeding 3,000 square feet. Many have been renovated, and pool additions are common on larger lots. The architectural style is consistent Florida residential — tile roofs, stucco exteriors, attached two-car garages. Two gated sections feature the larger estate-style homes on premium lots.

Nearby Communities

Port Orange Homes for Sale Halifax Plantation Ormond Beach New Smyrna Beach Homes Daytona Beach Homes Victoria Gardens DeLand

Interested in Cypress Head?

Robert Wrieden knows Port Orange and can show you active listings, run comparable sales, and walk you through HOA details before you make an offer — at no cost to you as a buyer.

💬 Text: (386) 387-5887
Schedule a Free Consultation

Robert Wrieden · REALTOR® SL3638019 · Summer Wind Realty Central Florida Inc. · 2020 Duncan Trace, DeLand, FL 32720 · Equal Housing Opportunity

🏠 Estimate Your Payment
Mortgage Calculator
Home Price $350,000
Down Payment 20% — $70,000
Interest Rate 6.75%
Loan Term
Estimated Monthly Payment
$2,271
$1,816 Principal & Interest
$292 Est. Taxes
$163 Est. Insurance
Get Pre-Approval Help → 📞 Call Robert — (386) 243-9602