Sleepy Hollow
Homes for Sale in Orlando, FL
All 4,060 homes for sale in Orlando, FL · median $384,945 · 55 homes for sale in 32810 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 17 closed sales in Sleepy Hollow Ph 02 in Orlando, FL since 2012, the most recent in December 2025. Across Orlando as a whole, 5,915 homes closed in the last 12 months at a median of $412,500, 41 median days on market, with 1,608 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $6,880 ($6,210 with the full homestead exemption).
Sleepy Hollow Ph 02 is a small, established pocket in Orlando — 36 homes, most built decades ago, with a median vintage around 1988 and a stock that stretches back as far as 1946 and up through 2005. That spread matters: price here is driven less by any single number and more by condition, updates, and lot. A renovated mid-century home and a tired one on the same street will trade very differently.
With homes at a median of roughly 1,311 square feet, this is a compact-footprint community, and the older, smaller stock rewards buyers who can read renovation potential. The homestead share sits just under 60%, pointing to a core of long-term ownership rather than a churn of rentals — which tends to keep supply thin and negotiations one-off rather than volume-driven.
Nearby homes for sale
No active listings inside Sleepy Hollow Ph 02 right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
This is a small, owner-heavy enclave of older, modestly sized homes in Orange County — the kind of place where each sale is its own conversation about condition rather than a comp-driven machine.
Stellar MLS sales records identify 23 homes in Sleepy Hollow that have changed hands since 2005, built between 1946 and 2005 (median 1988), with a median living area of about 1,467 sq ft and a typical 3-bedroom, 2-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
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.
Who Sleepy Hollow is best for.
Best for
- Buyers who want a compact-footprint home and are willing to renovate for value
- Long-hold buyers who value a low-turnover, owner-occupied street over churn
- Budget-conscious buyers reading condition and location rather than chasing new build
Probably not for
- Buyers needing substantial square footage or a large modern floor plan
- Buyers who want turnkey, recent-construction homes with no update work
- Buyers who need a deep pool of comparable listings to feel confident on price
The market around Sleepy Hollow
Sleepy Hollow is too small for its own price trend, so here is the market around it.
In ZIP 32810, 116 homes are on the market and 28% are under contract — a steady corner of Orlando.
Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).
In ZIP 32810 (Orlando), 168 homes closed in the last 12 months at a median of $325K ($232/sq ft), up 0.1% year over year, with a median 37 days on market. Right now 29 active and 12 pending listings put supply at about 4.4 months — a balanced market. See the live ZIP 32810 housing market and the Orange County market.
ZIP and county figures describe the wider market, not Sleepy Hollow specifically. Momentum Research analysis of MLS records.
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.
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 Sleepy Hollow.
Small stock, condition-driven pricing
With only 36 homes and a build range running from 1946 to 2005, Sleepy Hollow Ph 02 is not a subdivision of repeating floor plans. The median build year near 1988 sits well after the oldest homes, meaning you will find genuine variety — post-war construction alongside later infill. For a buyer, that means every listing deserves its own inspection lens; for a seller, it means your renovation choices, not a neighborhood formula, set your ceiling.
The compact median footprint of about 1,311 square feet frames the realistic play here: these are efficient homes where thoughtful updates to kitchens, systems, and layout carry disproportionate weight. Because turnover in a 36-home community is naturally limited, a well-prepared listing does not have to compete with a wall of similar inventory.
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
In a community this small and this varied by age and condition, the comp math is thin and easy to get wrong. We price and negotiate off the actual home in front of us — its vintage, its updates, its footprint — rather than a broad neighborhood average, and we set expectations honestly on both sides of the table.
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.
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.
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Should you buy in Sleepy Hollow?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2012 (17 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.
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See how Sleepy Hollow Ph 02 fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Sleepy Hollow
Where is Sleepy Hollow?
Sleepy Hollow is a community in Orlando, Orange County, Florida, ZIP 32810.
Are there homes for sale in Sleepy Hollow right now?
No active listings inside Sleepy Hollow at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Sleepy Hollow have an HOA or CDD?
No HOA is on record for Sleepy Hollow in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.
Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.
Nearby Communities
Explore more neighborhoods near Sleepy Hollow with Momentum Realty’s local guides.