Leesburg Sleepy Hollow
Homes for Sale in Leesburg, FL
All 632 homes for sale in LEESBURG, FL · median $285,000 · 466 homes for sale in 34748 · Lake County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, Leesburg Sleepy Hollow First Add in Leesburg, FL has 2 homes for sale. Over the 12 months ending 2026-09-20, 4 recorded sales closed at a median of $259,500, $193 per square foot, a median 9 days on market, sellers accepting 96% of original asking (-32% versus the prior year). Homes listed or recently sold were built 2005 - 2007; 7 of 7 report an HOA (median $38/mo); none of the 6 geocoded homes sit in a FEMA special flood hazard zone (median elevation 84 ft). At the median price and Lake County's FY2025-26 rate of 16.65 mills, annual property tax runs about $4,320 ($3,650 with the full homestead exemption).
Leesburg Sleepy Hollow right now
🟡 Balanced market. 3.0 months of supply and 50% 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 Stellar MLS records, as of September 12, 2026. Confidence: Medium (2 active and pending listings, 4 closed sales in 12 months).
🔴 Off the recent peak. The trailing-12-month median ($260K) is down 31.7% from the prior 12 months ($380K). With about 4 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 12. Confidence: Low (4 and 5 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 22, 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
Leesburg Sleepy Hollow market snapshot (as of September 12, 2026): the median sale price is about $260K ($193 per sq ft over the trailing 12 months of closed sales), a median 10 days on market for closed sales, and 3.0 months of supply, a balanced market. The trailing-12-month median is down 32% from the prior 12 months, computed from record-level Stellar MLS closed sales (4 closings in the current window).
In ZIP 34748 (LEESBURG), 1,072 homes closed in the last 12 months at a median of $290K ($161/sq ft), down 2.6% year over year, with a median 70 days on market. Right now 240 active and 63 pending listings put supply at about 5.0 months - a buyer's market. See the live ZIP 34748 housing market and the Lake County market.
County records show 4 qualified sales in Leesburg Sleepy Hollow across 2024 - 2025 (2 in 2024, 2 in 2025), median $392,000 - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Leesburg Sleepy Hollow is a community of 25 homes in Leesburg, Lake County, built between 2005 and 2017 (median 2005.0), with a median living area of about 1,773 square feet. 56% 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 Leesburg Sleepy Hollow. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Photos from Stellar MLS listings in Leesburg Sleepy Hollow; content deemed reliable but not guaranteed.
Housing distress & ownership in LEESBURG SLEEPY HOLLOW FIRST ADD, LEESBURG
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 Leesburg Sleepy Hollow
Live MLS inventory for Leesburg 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 Leesburg Sleepy Hollow listings as of 2026-09-12, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2024 through 2026. Tap any home to ask about it.
Every Home for Sale in Leesburg Sleepy Hollow First Add Leesburg Right Now (3)
All 3 active and pending Leesburg Sleepy Hollow First Add Leesburg listings with a detail page, newest first, refreshed twice a day from the MLS.
- 2721 Athens Drive · $360,000 · 4 bd / 3 ba · listed Sep 16, 2026 · listed by Millan Astray Realty Llc
- 204 Round Man Street · $297,000 · 4 bd / 2 ba · pending · listed Jul 20, 2026 · listed by Opendoor Brokerage Llc
- 2720 Savannah Drive · $440,000 · 4 bd / 3 ba · listed Jun 23, 2026 · listed by Lpt Realty, Llc
Leesburg 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.
The Leesburg Sleepy Hollow buying strategy.
If we were buying in Leesburg 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 Leesburg Sleepy Hollow.
A closer look at the Leesburg Sleepy Hollow market
At a median of $193 per square foot, Leesburg 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 3.0 months of supply, a balanced market and the trailing-12-month median down 32% year over year. Homes that do trade take a median 10 days on market, useful leverage on any listing that has lingered.
The housing stock is 25 homes built between 2005 and 2017, and 56% 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 Leesburg 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 Leesburg 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 (5.0). Basis: Recent Direction -31.7% year-over-year; Liquidity & Demand 3.0 months of supply; Owner Commitment 56% owner-occupied; Pricing Power 96.2% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- HOA dues reported around $38/month (about $456/yr) · median of 56 MLS listings, most billed quarterly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $38 per month ($456 a year) - the median AssociationFee across 56 MLS records, normalised to a monthly figure; most are billed quarterly. 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 Leesburg 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 Leesburg 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 Leesburg 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 Leesburg Sleepy Hollow home worth?
Get a no-obligation home value based on real comparable sales in Leesburg 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 Leesburg →
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Lake 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 · Lake 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.
19% of homes for sale in ZIP 34748 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 (2026-09-22).
LEESBURG SLEEPY HOLLOW FIRST ADD Market Scorecard
LEESBURG SLEEPY HOLLOW FIRST ADD is currently a buyer's market. About 6.0 months of supply, a median asking price of $400,000, and homes go under contract in about 62 days.
Typical home value in the 34748 ZIP is $274,372, about 2.2% above the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, distributed by MLS GRID, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Frequently Asked Questions
What is the median home price in Leesburg Sleepy Hollow?
How long do homes in Leesburg Sleepy Hollow take to sell?
Is Leesburg Sleepy Hollow a buyer's or seller's market right now?
How many homes are in Leesburg Sleepy Hollow?
What share of Leesburg Sleepy Hollow is owner-occupied?
When were the homes in Leesburg Sleepy Hollow built?
Who is the best real estate agent for Leesburg Sleepy Hollow?
How do I find a top Leesburg real estate agent who knows Leesburg Sleepy Hollow?
Can Momentum Realty connect me with an agent for Leesburg Sleepy Hollow?
Where is Leesburg Sleepy Hollow, and what county is it in?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 12, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 12, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 34748)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2024 (11 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 →
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A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Leesburg Sleepy Hollow fits the bigger picture — live prices, inventory, and Momentum Scores:
More Leesburg & Lake County guides
Compare before you commit - every guide covers pricing, HOA/CDD, insurance posture, and fit. Browse all of Lake County or the full Neighborhood Finder.
Nearby Communities
Explore more neighborhoods near Leesburg Sleepy Hollow with Momentum Realty’s local guides.