Sleepy Hollow
Homes for Sale in Longwood, FL
All 209 homes for sale in LONGWOOD, FL · median $449,900 · 69 homes for sale in 32750 · Seminole County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
As of September 2026, Sleepy Hollow 1St Add in Longwood, FL has 1 home for sale. Over the 12 months ending 2026-09-20, 3 recorded sales closed at a median of $605,000, $259 per square foot, a median 22 days on market, sellers accepting 99% of original asking (+22% versus the prior year). Homes listed or recently sold were built 1972 - 1975; 6 of 6 report an HOA (median $25/mo); none of the 6 geocoded homes sit in a FEMA special flood hazard zone (median elevation 90 ft). At the median price and Seminole County's FY2025-26 rate of 15.18 mills, annual property tax runs about $9,180 ($8,580 with the full homestead exemption).
| Location | LONGWOOD, Seminole County, FL · ZIP 32750 |
|---|---|
| Homes in the community | 26 (FL DOR 2025 assessment roll) |
| Years built | 1972–1976 (median 1973.5) |
| Typical living area | 2,090 sq ft (median) |
| Home types (current listings and sales) | single-family 100% |
| Amenities listed by sellers | Park, Playground, Deed Restrictions, Pickleball Court(s), Basketball Court, Fire Alarm |
| Sale prices, last 12 months | $605,000 median across 3 closed sales · $259 per sq ft · +21.6% vs the prior 12 months |
| Days on market (closed sales) | 22 median |
| For sale right now | 1 active, 0 pending · median asking $499,000 · 2.0 months of supply |
| Owner-occupied (homestead) share | 85% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2007 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Sleepy Hollow 1St Add key facts,” movewithmomentum.com/neighborhoods/sleepy-hollow-1st-add-longwood, data as of September 20, 2026.
Sleepy Hollow right now
🔴 Seller-leaning market. 2.0 months of supply and 0% 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 Stellar MLS records, as of September 20, 2026. Confidence: Low (1 active and pending listings, 3 closed sales in 12 months).
🟢 Still climbing. The trailing-12-month median ($605K) is up 21.6% from the prior 12 months ($498K). With about 3 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending September 20. Confidence: Low (3 and 5 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 27, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Sleepy Hollow market snapshot (as of September 20, 2026): the median sale price is about $605K ($259 per sq ft over the trailing 12 months of closed sales), a median 22 days on market for closed sales, and 2.0 months of supply, a seller-leaning market. The trailing-12-month median is up 22% from the prior 12 months, computed from record-level Stellar MLS closed sales (3 closings in the current window).
In ZIP 32750 (LONGWOOD), 313 homes closed in the last 12 months at a median of $431K ($237/sq ft), down 1.5% year over year, with a median 31 days on market. Right now 34 active and 12 pending listings put supply at about 3.3 months - a balanced market. See the live ZIP 32750 housing market and the Seminole County market.
County records show 5 qualified sales in Sleepy Hollow across 2024 - 2025 (2 in 2024, 3 in 2025), median $445,000 - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Sleepy Hollow is a community of 26 homes in Longwood, Seminole County, built between 1972 and 1976 (median 1973.5), with a median living area of about 2,090 square feet. 85% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
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
Photos from Stellar MLS listings in Sleepy Hollow; content deemed reliable but not guaranteed.
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 20 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($605K) IS the median in the snapshot above, and the move from 2025 ($498K) IS the +21.6% one-year change.
Windows contain 0 to 6 sales each (3 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2007 through 2026. Deemed reliable but not guaranteed.
33% of homes for sale in ZIP 32750 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 (2026-09-26).
Sleepy Hollow Market Scorecard
Sleepy Hollow is currently a seller-leaning market. About 2.0 months of supply, a median asking price of $499,000.
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, refreshed twice daily. Market metrics only; these describe homes for sale and recent sales, not residents.
Housing distress & ownership in Sleepy Hollow 1St Add, LONGWOOD
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period September 2026 through September 2026. Deemed reliable but not guaranteed.
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 2026-09-26, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2007 through 2026. Tap any home to ask about it.
Every Home for Sale in Sleepy Hollow 1St Add Longwood Right Now (1)
All 1 active and pending Sleepy Hollow 1St Add Longwood listings with a detail page, newest first, refreshed twice a day from the MLS.
- 2 Hudson Cove · $499,000 · 4 bd / 2 ba · pending · listed Jun 27, 2026 · listed by Legacy Realty & Brokers Llc
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 Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
Life at Sleepy Hollow
- Park · reported on 4 of 6 listings
- Pickleball Court(s) · reported on 4 of 6 listings
- Playground · reported on 4 of 6 listings
- Basketball Court · reported on 2 of 6 listings
- Deed Restrictions · reported on 2 of 6 listings
- Tennis Court(s) · reported on 2 of 6 listings
- Secured Garage/Parking · reported on 1 of 6 listings
- Irrigation-Reclaimed Water · reported on 1 of 6 listings
- Racquetball · reported on 1 of 6 listings
Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
Schools
- Seminole County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Altamonte Elementary · Elementary
- Rock Lake Middle · Middle
- Lyman High · High
Zoned schools reflect the assignments reported on recent Sleepy Hollow listings and can change; always confirm with Seminole 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 Lyman High 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 closer look at the Sleepy Hollow market
At a median of $259 per square foot, Sleepy Hollow prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
Inventory runs at 2.0 months of supply, a seller-leaning market and the trailing-12-month median up 22% year over year. Homes that do trade take a median 22 days on market, useful leverage on any listing that has lingered.
The housing stock is 26 homes built between 1972 and 1976, and 85% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
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.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in Sleepy Hollow buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 4 factors (8.9). Basis: Recent Direction +21.6% year-over-year; Liquidity & Demand 2.0 months of supply; Owner Commitment 85% owner-occupied; Pricing Power 98.6% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- HOA dues reported around $25/month (about $300/yr) · median of 83 MLS listings, most billed annually
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $25 per month ($300 a year) - the median AssociationFee across 83 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 Longwood →
Frequently Asked Questions
What is the median home price in Sleepy Hollow?
How long do homes in Sleepy Hollow take to sell?
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 Longwood 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?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 26, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 20, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (3 streets, ZIP 32750)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2007 (48 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS 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 Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
Looking to buy here? Search homes for sale →
What’s your home worth in your area?
A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Sleepy Hollow 1St Add fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
Explore more neighborhoods near Sleepy Hollow with Momentum Realty’s local guides.