Chesterbrook
Homes for Sale in Leesburg, FL
All 625 homes for sale in Leesburg, FL · median $285,000 · 14 condos for sale in Leesburg · 470 homes for sale in 34748 · Lake County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 14 closed sales in Chesterbrook 2 in Leesburg, FL since 2004, the most recent in July 2025. Across Leesburg as a whole, 836 homes closed in the last 12 months at a median of $282,000, 71 median days on market, with 305 homes for sale today. At that median and Lake County's FY2025-26 rate of 16.65 mills, annual property tax runs about $4,690 ($4,020 with the full homestead exemption).
There is no median price in this snapshot to anchor to, so treat Chesterbrook 2 as a community where price is driven by the individual home rather than a published market figure. In practice that means condition, lot, and updates carry the negotiation here more than any headline number.
For a buyer, that puts the work on comparing homes on their merits and pricing off recent nearby closings rather than a community average. For a seller, it means pricing to your home's actual condition and the current Lake County demand you can verify, not to a number pulled from the air.
The 60-Second Overview
Chesterbrook 2 is a small community in Leesburg, in Lake County, part of Central Florida's Golden Triangle area near the Harris Chain of Lakes. It reads as a defined, self-contained pocket rather than a sprawling master plan.
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 Chesterbrook is best for.
Best for
- Buyers targeting a specific, smaller Leesburg community over a large master-planned option
- Buyers who will judge a home on its own condition and lot rather than a community average
- Buyers who value proximity to Lake County and the Central Florida lakes region
Probably not for
- Buyers who need many active listings to compare at once
- Buyers who want a single published price figure to shop against
- Buyers set on a different city or county entirely
The market around Chesterbrook
Chesterbrook is too small for its own price trend, so here is the market around it.
In ZIP 34748, 583 homes are on the market and 18% are under contract — a slower corner of Leesburg.
Across Lake County, 3,179 homes are active and 1,077 pending (25% under contract).
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.
ZIP and county figures describe the wider market, not Chesterbrook specifically. Momentum Research analysis of MLS records.
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 (2026-09-24).
Chesterbrook 2 Market Scorecard
Chesterbrook 2 is currently a thin data market. Limited supply, a median asking price of $40,000, and homes go under contract in about 239 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: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Homes For Sale Right Now in Chesterbrook
Live MLS inventory for Chesterbrook. 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 Chesterbrook listings as of 2026-09-19, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2004 through 2025. Tap any home to ask about it.
Every Home for Sale in Chesterbrook 2 Right Now (1)
All 1 active and pending Chesterbrook 2 listings with a detail page, newest first, refreshed twice a day from the MLS.
- 500 Newell Hill Road #106D · $40,000 · 2 bd / 2 ba · pending · listed Jun 25, 2026 · listed by Professional Real Estate Team
The Chesterbrook buying strategy.
If we were buying in Chesterbrook 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 Chesterbrook.
A small Leesburg pocket
With only the name, city, and county to go on, the honest read is that Chesterbrook 2 is best understood block by block and home by home. In a community this size, one or two active listings can shift the whole picture, so a current pull from the Stellar MLS feed matters more than any general statement about the area.
Leesburg sits within Lake County and the broader Central Florida lakes region, which shapes commute patterns, water access, and everyday errands. Beyond that, we won't guess at amenities or figures we can't verify — we'll confirm them against live data before you act.
The location and the amenities are priced into every listing in Chesterbrook. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a community this small, the numbers you find online are easy to misread because one listing can swing the average. We work directly from the Stellar MLS feed and current Lake County closings, so we can tell you what a specific Chesterbrook 2 home is actually worth today rather than leaning on a stale or auto-generated figure.
Chesterbrook in 15 seconds.
HOA, CDD & Fees
- HOA dues reported around $870/month (about $10,440/yr) · median of 12 MLS listings, most billed monthly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $870 per month ($10,440 a year) — the median AssociationFee across 12 MLS records, normalised to a monthly figure; most are billed monthly. 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 Chesterbrook 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 Chesterbrook sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Chesterbrook, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Chesterbrook home worth?
Get a no-obligation home value based on real comparable sales in Chesterbrook, 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 →
Should you buy in Chesterbrook?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 19, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2004 (14 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 Chesterbrook 2 fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Chesterbrook
Where is Chesterbrook?
Chesterbrook is a community in Leesburg, Lake County, Florida, ZIP 34748.
Are there homes for sale in Chesterbrook right now?
Yes — 1 active and 0 pending listings as of the last feed refresh (twice daily). They are listed on this page.
Does Chesterbrook have an HOA or CDD?
No HOA is on record for Chesterbrook 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.
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
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