Sleepy Hollow
Homes for Sale in Port Orange, FL
True comps, carrying-cost math, and listings before the portals.
Photo courtesy of Coldwell Banker Commercial Benchmark · via DBAMLS
Sleepy Hollow is a small, tightly built pocket of 152 homes in Port Orange, all constructed between 1977 and 1985, with a median year built of 1978 and a median living area of 1,810 square feet. Because the housing stock sits in that narrow band, price differences here come down to lot, layout, and how well a given home has been updated, not any real spread in age or size.
Right now the numbers point to a seller-leaning market: just 1.3 months of supply and only a single active listing across the entire community. That is a thin market in both directions — sellers have little competition when they do list, and buyers who want in should be ready to act quickly, because there is not much on the market to compare against.
Sleepy Hollow right now
🔴 Seller-leaning market. 1.3 months of supply and 50% of the inventory already under contract give sellers the pressure advantage.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: Low (2 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
Built out between 1977 and 1985, Sleepy Hollow is a compact, owner-heavy pocket of Port Orange anchored by a shared pool and clubhouse rather than new-construction extras.
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 Sleepy Hollow. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Sleepy HollowPhotos from DBAMLS listings in Sleepy Hollow; content deemed reliable but not guaranteed.
Who Sleepy Hollow is best for.
Best for
- Buyers set on an established, single-era community with a shared pool and clubhouse.
- Buyers who can act fast and don't need a long list of comparable homes to shop first.
- Buyers looking for a home near the 1,810-square-foot median size, with room to update or personalize.
Probably not for
- Buyers who want to compare multiple active listings side by side before making an offer.
- Buyers hoping for new-construction finishes or systems, since homes here date to 1977-1985.
- Investors seeking a concentration of non-owner-occupied or seasonal inventory to acquire.
The market around Sleepy Hollow
Sleepy Hollow 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 Sleepy Hollow specifically. Momentum Research analysis of MLS records.
Homes For Sale Right Now in Sleepy Hollow
Live MLS inventory for Sleepy Hollow. 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 · 77 daysTop listing
Active · 29 days
Pending · 0 daysActive and pending Sleepy Hollow listings as of 2026-10-10, priced high to low. © 2026 Daytona Beach Area Association of REALTORS®, Inc. Tap any home to ask about it.
Sleepy Hollow 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, tiles © CARTO.
Life at Sleepy Hollow
- Pool · reported on 2 of 3 listings
- Clubhouse · reported on 1 of 3 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
- Sugar Mill · Elementary
- Silver Sands · Middle
- Spruce Creek · High
Zoned schools reflect the assignments reported on recent Sleepy Hollow 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 Sleepy Hollow address.
Recent Developments in Sleepy Hollow
Development, infrastructure, retail, and school activity affecting Sleepy Hollow, 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 7 miles southeast of Sleepy Hollow.
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 6 miles northwest of Sleepy Hollow.
Source: FlaglerLive - October 2026Parks & Amenities
Volusia County approves $13 million in ECHO grants for 10 projects
The council approved grants including $2.5 million each for Edgewater, Daytona Beach and the D Ranch Preserve nature center, plus a 250-foot Halifax River pier in Holly Hill, a boat dock in New Smyrna Beach, a DeBary splash pad and Port Orange's Willow Run Park.
What it may mean for the marketFunds new waterfront access and park amenities across several Volusia communities. The site is about 9 miles north of Sleepy Hollow.
Source: WFTV - 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 1 mile northwest of Sleepy Hollow.
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 6 miles north of Sleepy Hollow.
Source: Hometown News Volusia - 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 5 miles south of Sleepy Hollow.
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 Sleepy Hollow buying strategy.
If we were buying in Sleepy Hollow 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.
Come strong and clean. Homes here move, so lead with your best terms and financing ready rather than a low anchor.
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 Sleepy Hollow.
A Small, Owner-Held Pocket
With 152 homes total and just one active listing at this snapshot, Sleepy Hollow trades thin. The 1.3 months of supply puts it firmly in seller-leaning territory — there simply are not many homes changing hands at once, so pricing tends to hold rather than get tested by a wave of comparable listings.
The community was built out between 1977 and 1985, with a median year built of 1978 and a median living area of 1,810 square feet, so most homes share a similar footprint and era of construction. Ownership here skews heavily toward homestead-exempt properties rather than investor or seasonal holdings. Shared amenities include a pool and clubhouse, though buyers should confirm current access and condition directly with the HOA.
The location and the amenities are priced into every listing in Sleepy Hollow. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
With inventory this thin — one active listing against 152 total homes — off-market awareness and quick, informed action matter more than they would in a higher-volume subdivision. Momentum tracks Sleepy Hollow's listing activity closely so buyers can move fast when something surfaces and sellers can price against the real, current picture rather than stale comps.
Sleepy Hollow in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- Any club/amenity membership is billed separately
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Flood & Insurance Context
Of 10 sampled listing addresses in this community: 100% outside the FEMA Special Flood Hazard Area (Zone X/B/C).
Address-sampled; individual parcels vary - verify any specific address at msc.fema.gov. Check any address at FEMA's Flood Map Service Center, and see average home-insurance costs by Florida county.
Source: FEMA National Flood Hazard Layer, address-level lookups (n=10) · as of 2026-10
Tools for a Sleepy Hollow 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 Sleepy Hollow sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Sleepy Hollow, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Sleepy Hollow home worth?
Get a no-obligation home value based on real comparable sales in Sleepy Hollow, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See homes for sale in Sleepy Hollow on the map →
Frequently Asked Questions
Is Sleepy Hollow a buyer's or seller's market right now?
How many homes are in Sleepy Hollow?
What share of Sleepy Hollow is owner-occupied?
When were the homes in Sleepy Hollow built?
Who is the best real estate agent for Sleepy Hollow?
How do I find a top Port Orange real estate agent who knows Sleepy Hollow?
Can Momentum Realty connect me with an agent for Sleepy Hollow?
Should you buy in Sleepy Hollow?
An honest fit check. We will tell you when it is not your community.
Nearby Communities
Explore more neighborhoods near Sleepy Hollow with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | DBAMLS, refreshed twice daily (last: October 10, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (community parcel extract) |
| 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.
Own a home here?
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The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the DBAMLS member average and 8 days faster, and we’ll price yours against live local comps.
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