Sleepy Hollow
Homes for Sale in Port Orange, FL
All 278 homes for sale in Port Orange, FL · median $317,250 · Volusia County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo courtesy of Coldwell Banker Commercial Benchmark · via DBAMLS
As of September 2026, Sleepy Hollow in Port Orange, FL has 1 home for sale. Homes listed or recently sold were built 1977–1992; 3 of 11 report an HOA (median $25/mo); none of the 11 geocoded homes sit in a FEMA special flood hazard zone (median elevation 8 ft).
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 and pending Sleepy Hollow listings as of 2026-09-19, priced high to low. © 2026 Daytona Beach Area Association of REALTORS®, Inc. Tap any home to ask about it.
Every Home for Sale in Sleepy Hollow Port Orange Right Now (2)
All 2 active and pending Sleepy Hollow Port Orange listings with a detail page, newest first, refreshed twice a day from the MLS.
- 4597 Barnacle Drive · $299,900 · 3 bd / 2 ba · listed Sep 11, 2026 · listed by RE/MAX Advantage
- 709 Tarry Town Trail · $350,000 · 3 bd / 2 ba · listed Jul 26, 2026 · listed by The Keyes Company
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 September 20, 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.
Flood zones in Sleepy Hollow: of 10 listing addresses checked against the FEMA National Flood Hazard Layer, 100% sit outside the FEMA Special Flood Hazard Area (Zone X). Individual parcels vary — verify any specific address at msc.fema.gov. See flood zones by neighborhood in Port Orange.
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.
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.
Shop the zone: Homes zoned for Spruce Creek High School
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 dues reported around $28/month (about $336/yr) · median of 16 MLS listings, most billed annually
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $28 per month ($336 a year) — the median AssociationFee across 16 MLS records, normalised to a monthly figure; most are billed annually. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-09.
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
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 all homes for sale in Port Orange →
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Volusia County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Volusia County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.
16% of homes for sale in ZIP 32127 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-09-20).
Sleepy Hollow Market Scorecard
Sleepy Hollow is currently a buyer-leaning market (limited data). About 4.5 months of supply, a median asking price of $299,900, and homes go under contract in about 56 days.
Typical home value in the 32127 ZIP is $354,479, about 8.8% above the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: © 2026 Daytona Beach Area Association of REALTORS®, Inc. Refreshed twice daily. Market metrics only; these describe homes for sale and recent sales, not residents.
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?
Where is Sleepy Hollow, and what county is it in?
Is Sleepy Hollow in a flood zone?
Should you buy in Sleepy Hollow?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | DBAMLS, refreshed twice daily (last: September 19, 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?
You just read the data. Now see what your home is worth.
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.
Looking to buy here? Search homes for sale →
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See how Sleepy Hollow fits the bigger picture — live prices, inventory, and Momentum Scores:
More Port Orange & Volusia County / Daytona Beach Area guides
Compare before you commit - every guide covers pricing, HOA/CDD, insurance posture, and fit. Browse all of Volusia County / Daytona Beach Area or the full Neighborhood Finder.
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