Cypress Head Port Orange: Complete Community Guide 2026

By Robert Wrieden, REALTOR® | Summer Wind Realty Central Florida | June 1, 2026

Golf course living, A-rated schools, and 5 miles to the beach — your complete 2026 guide to one of Port Orange’s most sought-after communities

If you’re searching for golf course living in Volusia County without the country club price tag, Cypress Head in Port Orange deserves a serious look. This established gated community checks a lot of boxes — Arthur Hills-designed course, top-rated schools, a genuine neighborhood feel, and a location that puts you 5 miles from the beach and minutes from Port Orange’s best shopping and dining.

I’ve worked with buyers in Cypress Head and know the community well. This guide covers everything — the golf course, amenities, HOA, schools, price ranges, and what to expect day-to-day as a resident.

What’s in This Guide

• About the Community
• The Golf Course
• Amenities
• Home Types & Prices
• HOA Information
• Schools
• Location & Nearby
• Community Lifestyle
• FAQ

About the Community

Cypress Head is a gated golf course community in the southwest corner of Port Orange, developed in the 1990s and early 2000s by Paytas Homes. The neighborhood is built around an Arthur Hills-designed 18-hole golf course, with homes lining the fairways and surrounding natural preservation areas and fishing lakes that give the whole community a park-like feel.

What sets Cypress Head apart from newer Port Orange developments is its established character. The mature tree canopy, settled landscaping, and sense of permanence that comes with a community that’s been here for 25+ years is something you can’t manufacture. Neighbors know each other. The annual Christmas Eve Golf Cart Parade is a genuine community tradition, not a marketing gimmick.

The community is divided into two main sections — the single-family home neighborhoods managed by the Cypress Head Master HOA, and the Golf Villas townhome section at the north end near Airport Road, which has its own separate HOA and community pool. Both sections share access to the golf course and common areas.

The Golf Course

The Golf Club at Cypress Head is one of the best public courses in the Daytona Beach area — designed by Arthur Hills and Mike Dasher, consistently well-regarded for its wide fairways, excellent conditioning, and challenging but playable layout. You don’t need to feel like a scratch golfer to enjoy it, but the course has enough character to keep experienced players engaged.

Key Golf Course Details

• Design: Arthur Hills & Mike Dasher — award-winning public course
• Type: Public — open to non-residents, separate fees apply for residents
• Layout: 18 holes, wide fairways, natural preservation areas, water features
• Driving Range: On site
• Dining: Flagsticks Bar & Grill on site at the clubhouse
• Golf Villas View: Townhomes overlook holes 4, 5, and 6

Community Amenities

Beyond the golf course, Cypress Head residents have access to a solid package of community amenities through the HOA:

Home Types & Price Ranges

Cypress Head offers two distinct housing options, which is part of its appeal — you can find an entry point at the Golf Villas or go all the way up to a large estate home on the fairway.

Single-Family Homes

The bulk of Cypress Head is single-family homes, mostly built by Paytas Homes. The majority are split-plan layouts in the 1,600–2,400 sq ft range, though larger estate homes exist throughout the community. Many back to the golf course, lakes, or preserve areas.

• Typical size: 1,600–2,800+ sq ft
• Bedrooms: 3–4 bed most common, some larger
• Price range: Low $300Ks to $500K+
• Median price: Approximately $400K–$525K (2025–2026)
• Premium lots: Golf course, lake, and preserve views command higher prices

Golf Villas — Townhomes

Located at the northern end of the community near Airport Road, the Golf Villas are a separate enclave of townhomes overlooking holes 4, 5, and 6. They offer maintenance-free living with their own community pool — a great option for snowbirds, retirees, or buyers who want golf community living without the yard work.

• Style: Townhomes with Spanish tile roofs, volume ceilings
• Layout: Single and two-story floorplans
• Parking: Private garage and driveway + guest parking
• Views: Golf course (holes 4–6)
• Price range: Starting in the mid-$200Ks (most affordable entry into Cypress Head)
• Managed by: South Atlantic Communities (separate from master HOA)

HOA Information

Cypress Head has a master HOA that covers the single-family home sections, with the Golf Villas managed separately by South Atlantic Communities. HOA fees cover common area maintenance, community amenities, landscaping of common areas, and gated access operations.

HOA Contact & Management

• HOA Address: 6251 Palm Vista St, Port Orange, FL 32128
• Phone: (386) 760-3212
• Website: cypressheadhoa.org
• Estoppel Contact: ashley@toutmgmt.com
• Board Meetings: Monthly at the clubhouse — residents encouraged to attend

What HOA Fees Cover

• Common area maintenance and landscaping
• Community pool and amenity upkeep
• Gated access operations
• Community management fees
• Recreational committees and community events

Schools

This is one of Cypress Head’s strongest selling points for families. The community falls within the Spruce Creek High School district — consistently one of the top-rated public high schools in Port Orange, known for its International Baccalaureate program and advanced coursework. The feeder schools are equally strong:

• Elementary: Cypress Creek Elementary School — within walking distance of the community
• Middle: Creekside Middle School — highly rated Volusia County school
• High: Spruce Creek High School — IB program, advanced academics, consistently A-rated

The fact that Cypress Creek Elementary is within walking distance of the community is a genuine differentiator — that’s increasingly rare in Volusia County and a real quality-of-life benefit for families.

Location & What’s Nearby

Cypress Head sits in the southwest corner of Port Orange — well-positioned for access to the interstate, beaches, and everyday services without sitting in the middle of the commercial sprawl along US-1 and Dunlawton.

Community Lifestyle

Cypress Head has an active community culture built around its recreational committees and regular events. The annual Christmas Eve Golf Cart Parade has become a beloved community tradition — neighbors decorate their carts and roll through the neighborhood. It’s the kind of thing that tells you a community has real social fabric, not just a marketing brochure.

The community draws a mix of families (attracted by the schools and golf course setting), retirees and semi-retirees (drawn to the active adult lifestyle without an age restriction), and buyers relocating from the Northeast who want golf, beach proximity, and a friendly neighborhood feel. It’s not a 55+ community but it has a lot of that same energy.

The boating culture around Port Orange adds another dimension — many Cypress Head residents take advantage of the Halifax River, Ponce Inlet, and the small island chains accessible by kayak and paddleboard near New Smyrna Beach. You don’t need to be a golfer to love living here.

Frequently Asked Questions