Chester Oaks
Homes for Sale in Clermont, FL
All 725 homes for sale in Clermont, FL · median $450,000 · 48 homes for sale in 34715 · Lake County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of October 2026, the MLS records 6 closed sales in Chester Oaks in Clermont, FL since 2005, the most recent in March 2026. Across Clermont as a whole, 940 homes closed in the last 12 months at a median of $438,065, 41 median days on market, with 229 homes for sale today. At that median and Lake County's FY2025-26 rate of 16.65 mills, annual property tax runs about $7,290 ($6,620 with the full homestead exemption).
Chester Oaks is a small, established pocket of Clermont housing stock — 66 homes with a build range stretching from 1948 to 2001 and a median year built of 1984. That spread means no two blocks look alike; you'll find older, smaller-footprint homes sitting near later infill construction, and condition (not era alone) is doing most of the work on price. With a median living area of 1,182 square feet, this is a community of modest, efficient floor plans rather than large-format houses.
The homestead share here sits at 71.2%, which points to a market where a majority of owners have filed for homestead exemption — a signal of longer holding periods rather than a heavy churn of investor or short-term resale inventory. For buyers, that generally means fewer listings turn over at once, so when a well-kept home does list, it's worth moving on with real diligence rather than waiting for a wave of comparable choices.
Nearby homes for sale
No active listings inside Chester OaksHomes for Sale in Clermont, FL 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
Chester Oaks is a compact, older Clermont neighborhood in Lake County where home vintage varies by decades rather than years, and the current MLS record shows no community amenities attached to listings — this is a housing stock play, not an amenity play.
Stellar MLS sales records identify 5 homes in Chester Oaks that have changed hands since 2010, built between 1993 and 1995 (median 1994), with a median living area of about 1,115 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.
County records show 3 qualified sales in Chester Oaks across 2024–2024, median $325,000 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
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 Chester Oaks is best for.
Best for
- Buyers looking for a compact, efficient home in Clermont without paying for amenity overhead
- Buyers comfortable budgeting for inspection-driven repairs on an older home in exchange for location and price flexibility
- Owner-occupant buyers planning a longer hold, consistent with the neighborhood's high homestead-exemption share
Probably not for
- Buyers who want a subdivision with a consistent, single-era construction standard throughout
- Buyers prioritizing community amenities such as a pool, clubhouse, or organized common areas
- Buyers who need larger square footage than the neighborhood's modest median living area typically offers
The market around Chester Oaks
Chester Oaks is too small for its own price trend, so here is the market around it.
In ZIP 34715, 278 homes are on the market and 38% are under contract — a fast-moving corner of Clermont.
Across Lake County, 3,179 homes are active and 1,077 pending (25% under contract).
In ZIP 34715 (Clermont), 970 homes closed in the last 12 months at a median of $532K ($235/sq ft), up 3.9% year over year, with a median 35 days on market. Right now 64 active and 78 pending listings put supply at about 2.2 months — a strong market. See the live ZIP 34715 housing market and the Lake County market.
ZIP and county figures describe the wider market, not Chester Oaks specifically. Momentum Research analysis of MLS records.
The Chester Oaks buying strategy.
If we were buying in Chester Oaks 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 Chester Oaks.
A range, not a template
With homes dating from 1948 through 2001 and a median build year of 1984, Chester Oaks doesn't read as a single-phase subdivision — it reads as a neighborhood that filled in and was renovated across multiple decades. That has real implications for due diligence: roof age, electrical, and plumbing systems will vary meaningfully from one address to the next even on the same street, so a home inspection here is doing more work than it would in a community built in a five-year window.
The median living area of 1,182 square feet keeps this squarely in modest-footprint territory. Buyers shopping Chester Oaks should expect efficient layouts rather than expansive square footage, and should size up living space against actual need rather than against newer-construction norms elsewhere in Clermont.
The location and the amenities are priced into every listing in Chester Oaks. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a small, mixed-vintage community like Chester Oaks, the deal is won or lost in the inspection period and the comp pull — not the marketing copy. We pull the Stellar MLS data on build year, condition, and recent activity property by property, and we tell you plainly when a listing's price doesn't match its age or system condition, whether you're buying or selling.
Chester Oaks 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 Chester Oaks 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 Chester Oaks sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Chester Oaks, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Chester Oaks home worth?
Get a no-obligation home value based on real comparable sales in Chester Oaks, 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 Chester Oaks?
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 2005 (6 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.
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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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Common questions about Chester Oaks
Where is Chester Oaks?
Chester Oaks is a community in Clermont, Lake County, Florida, ZIP 34715.
Are there homes for sale in Chester Oaks right now?
No active listings inside Chester Oaks at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Chester Oaks have an HOA or CDD?
No HOA is on record for Chester Oaks 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 Clermont & 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 Chester Oaks with Momentum Realty’s local guides.
Chester Oaks Market Scorecard
Chester Oaks is currently a no active listings market. Limited supply, a median asking price of n/a.
Typical home value in the 34715 ZIP is $461,244, about 5.4% below 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.