Cypress Head
Homes for Sale in Port Orange, FL
True comps, carrying-cost math, and listings before the portals.
Photo courtesy of Kelly Beechler, Beechler Realty Group · via DBAMLS
Cypress Head is a gated golf-course community in Port Orange where pricing reflects condition, view, and proximity to the course more than age alone. The inventory spread here tends to be wide—listings range from properties needing updates to recently renovated—so buyers should budget time to tour multiple homes and understand what they're getting at a given price point.
With six active listings and three months of supply, the market is balanced. Neither buyers nor sellers hold the edge right now, which means negotiation room exists but won't be dramatic. Sellers who overprice for condition will sit; buyers who move decisively on well-presented homes near the course or with preserve views can close without a bidding war.
Figures in this note are as of July 17, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Cypress Head right now
🟡 Balanced market. 3.0 months of supply and 25% of the inventory already under contract put buyers and sellers on roughly even footing.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of DBAMLS records, as of July 12, 2026. Confidence: Medium (8 active and pending listings, 0 closed sales in 12 months).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated July 12, 2026 · Live data: DBAMLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Cypress Head is a gated, golf-course community in Port Orange with a full roster of amenities—tennis, pickleball, pool, clubhouse—and full-time management. It's a mature neighborhood where pricing is condition-driven and the current balanced market gives both sides room to negotiate.
Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.
The setting & the homes.
Aerial and on-site photos of Cypress Head. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Cypress HeadPhotos from DBAMLS listings in Cypress Head; content deemed reliable but not guaranteed.
Who Cypress Head is best for.
Best for
- Buyers seeking a gated, golf-course lifestyle with tennis, pickleball, and pool access who are comfortable with HOA-managed amenities and services.
- Buyers who will tour multiple listings to compare condition and location, and who understand that price reflects finish level and course proximity.
- Buyers looking for a balanced market where negotiation is possible and inventory allows time to choose the right property without pressure.
Probably not for
- Buyers seeking minimal HOA fees or who prefer to manage their own landscaping and exterior maintenance.
- Buyers expecting uniform home quality across all price points, or who won't budget time to evaluate condition differences carefully.
- Buyers looking for a rapidly appreciating market or who need a large selection of move-in-ready listings at a single price tier.
The market around Cypress Head
Cypress Head is too small for its own price trend, so here is the market around it.
Across Volusia County, 4,230 homes are active and 1,084 pending (20% under contract).
ZIP and county figures describe the wider market, not Cypress Head specifically. Momentum Research analysis of MLS records.
Homes For Sale Right Now in Cypress Head
Live MLS inventory for Cypress Head. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active · 130 daysTop listing
Active · 217 days
Pending · 71 days
Pending · 60 days
Pending · 198 daysActive and pending Cypress Head listings as of 2026-10-22, priced high to low. © 2026 Daytona Beach Area Association of REALTORS®, Inc. Tap any home to ask about it.
Cypress Head on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from DBAMLS. Map data © OpenStreetMap contributors.
Life at Cypress Head
- Tennis Court(s) · reported on 19 of 19 listings
- Pool · reported on 19 of 19 listings
- Clubhouse · reported on 18 of 19 listings
- Pickleball · reported on 18 of 19 listings
- Gated · reported on 9 of 19 listings
- Security Gate · reported on 8 of 19 listings
- Golf Course · reported on 7 of 19 listings
- Maintenance Grounds · reported on 3 of 19 listings
- Management - Full Time · reported on 1 of 19 listings
- Cable TV · reported on 1 of 19 listings
- Maintenance Structure · reported on 1 of 19 listings
- Playground · reported on 1 of 19 listings
Community amenities as reported across DBAAR listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
Schools
- Volusia County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Cypress Creek · Elementary
- Creekside · Middle
- Spruce Creek · High
Zoned schools reflect the assignments reported on recent Cypress Head listings and can change; always confirm with Volusia County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Cypress Head address.
Recent Developments in Cypress Head
Development, infrastructure, retail, and school activity affecting Cypress Head, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated October 2026.
- October 2026Development
AdventHealth opens urgent care and primary care clinics on State Road 44 in New Smyrna Beach
AdventHealth Primary Care at 2368 State Road 44 accepts patients ages 5 and up, and Centra Care next door offers walk-in urgent care seven days a week with onsite X-ray and lab. Centra Care is the system's first urgent care in New Smyrna Beach and its sixth in Volusia County.
What it may mean for the marketImproves access to walk-in and primary medical services for the New Smyrna Beach area. The site is about 5 miles southeast of Cypress Head.
Source: Hometown News Volusia - October 2026Development
Manufacturing and technology job fair set for Oct. 15 at Daytona State
Germfree, B. Braun, Teledyne, Embler Control Systems, Bylight, Pall Corporation and the Electrical Training Alliance will recruit at the Advanced Technology College on Williamson Boulevard in Daytona Beach. The fair runs 2:30 to 5:30 p.m., with a morning session for Volusia high school students.
What it may mean for the marketShows active hiring by regional manufacturing and technology employers. The site is about 8 miles north of Cypress Head.
Source: FlaglerLive - September 2026Infrastructure
Port Orange council upholds award of $14.4 million Cambridge Canal pump station contract
The council voted 5-0 on Sept. 15 to deny a bid protest, keeping the $14.4 million contract with Gregori Construction for the Cambridge Canal and Pump Station upgrade. It is the city's largest stormwater project and aims to reduce flooding and tidal impacts. A formal contract award returns to the council.
What it may mean for the marketStormwater capacity upgrades bear on flood-risk management for nearby Port Orange areas. The site is about 5 miles north of Cypress Head.
Source: Hometown News Volusia - September 2026Infrastructure
VoTran changes routes Oct. 4, adds DeLand express and discontinues two routes
Route 61X adds weekday service between the Transfer Plaza and the DeLand ITF via I-4, while Routes 33 and 70 are discontinued. A new VoRide Sunday zone in the Daytona Beach area replaces fixed Sunday service on Routes 3, 4, 10 and 15. The County Council approved the changes on June 16.
What it may mean for the marketChanges commute options between Daytona Beach and DeLand and shifts some service to on-demand rides. The site is about 10 miles north of Cypress Head.
Source: Hometown News Volusia - May 2026Development
Daytona Beach approves Avalon Park Daytona, a master-planned community of about 8,800 homes west of I-95
Daytona Beach commissioners approved Avalon Park Daytona in May 2026, clearing the way for a master-planned community of about 8,800 homes on land west of Interstate 95. The approval also allows commercial and mixed-use space as the project builds out over many years.
What it may mean for the marketA large new master-planned community adds substantial future housing supply west of Interstate 95, a shift that can influence competition and pricing for existing communities in the area. The site is about 10 miles northwest of Cypress Head.
Source: Observer Local News - March 2026Infrastructure
FDOT builds a new $75 million I-95 interchange at Pioneer Trail near New Smyrna Beach
The Florida Department of Transportation is building a new $75 million interchange on Interstate 95 at Pioneer Trail near New Smyrna Beach. The roughly 2-mile project widens Pioneer Trail to four lanes and adds a roundabout at Turnbull Bay Road, with construction underway in 2026.
What it may mean for the marketA new interstate interchange improves access and shortens drive times in southeast Volusia, the kind of infrastructure that has historically shaped where demand and new development concentrate. The site is about 2 miles south of Cypress Head.
Source: Florida DOT (cflroads)
Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in Northeast Florida.
The Cypress Head buying strategy.
If we were buying in Cypress Head today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Cypress Head.
What you're buying into at Cypress Head
Cypress Head sits in Port Orange, Volusia County, behind a security gate with a golf course threading through the community. The amenity package is complete: lighted tennis and pickleball courts, a community pool, clubhouse, playground, and full-time on-site management. Grounds and structure maintenance are handled by the association, and cable TV is bundled. This is a turn-key lifestyle community—you pay the HOA for convenience and access.
The golf course defines the premium tier here. Homes with fairway or preserve views command more; interior-lot properties trade for less. The housing stock is varied in age and finish level, so condition is the price driver. Some listings show original finishes and dated layouts; others have been renovated with modern kitchens, baths, and flooring. Walk every home with a critical eye—what you see is what you'll live with or budget to change.
With six active listings and three months of supply, the market is balanced. Buyers have options and time to compare; sellers need to price correctly for condition and location within the community. Overpricing based on a neighbor's sale two years ago won't work. Buyers who understand the condition spread and move on well-presented properties near the course will have the upper hand in this window.
The location and the amenities are priced into every listing in Cypress Head. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
Cypress Head's pricing is condition- and location-specific, and the spread between dated and updated homes is real. We'll walk you through what each listing actually offers—original finishes versus renovated, interior lot versus course view—and what that means for value. Our team knows the Volusia golf-course communities and will tell you when a property is overpriced for its condition or when you're looking at a solid buy. We represent your interest, not the transaction.
Cypress Head in 15 seconds.
Tools for a Cypress Head buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Cypress Head sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Cypress Head, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Cypress Head home worth?
Get a no-obligation home value based on real comparable sales in Cypress Head, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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Frequently Asked Questions
Is Cypress Head a buyer's or seller's market right now?
Who is the best real estate agent for Cypress Head?
How do I find a top Port Orange real estate agent who knows Cypress Head?
Can Momentum Realty connect me with an agent for Cypress Head?
Should you buy in Cypress Head?
An honest fit check. We will tell you when it is not your community.
Nearby Communities
Explore more neighborhoods near Cypress Head with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | DBAMLS, refreshed twice daily (last: October 22, 2026) |
| Under-contract shares | DBAMLS records, as of 2026-07-12 |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of DBAMLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
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