Chesterfield Heights
Homes for Sale in Clearwater, FL
All 1,174 homes for sale in Clearwater, FL · median $295,500 · 137 homes for sale in 33756 · Pinellas County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Stellar MLS
As of October 2026, Chesterfield Heights 1St Add in Clearwater, FL has 2 homes for sale. Over the 12 months ending 2026-09-20, 3 recorded sales closed at a median of $480,000, $331 per square foot, a median 2 days on market, sellers accepting 100% of original asking. Homes listed or recently sold were built 1959–1970; none of the 5 geocoded homes sit in a FEMA special flood hazard zone (median elevation 40 ft). At the median price and Pinellas County's FY2025-26 rate of 19.39 mills, annual property tax runs about $9,310 ($8,490 with the full homestead exemption).
| Location | Clearwater, Pinellas County, FL · ZIP 33756 |
|---|---|
| Home types (current listings and sales) | single-family 100% |
| Amenities listed by sellers | Closed Circuit Camera(s), Security System |
| Sale prices, last 12 months | $480,000 median across 3 closed sales · $331 per sq ft |
| Days on market (closed sales) | 2 median |
| For sale right now | 2 active, 0 pending · median asking $409,000 · 8.0 months of supply |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2015 through 2026. Market figures describe homes, not residents. Cite as: Momentum Realty, “Chesterfield Heights 1St Add key facts,” movewithmomentum.com/neighborhoods/chesterfield-heights-1st-add, data as of September 20, 2026.
Last 30 days in Chesterfield Heights: 2 new listings (median asking $406,500). As of October 2, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
Price here is driven by condition, not by any single floor plan or era. These are mid-century homes, built between 1956 and 1981 with a median build year of 1960, and the median living area sits right around 1,491 square feet. What that means in practice: a renovated house and an original one on the same street can be worlds apart on price. The number that matters is the work already done to the structure and systems.
With only a couple of closings in the recent window, this is a thin-data market, so lean on the home in front of you rather than the last comp. About 80% of homes carry a homestead exemption, which points to long-term ownership and a limited flow of listings. For sellers, that scarcity can work in your favor when your home shows well; for buyers, it means patience and a willingness to move when the right condition-and-price combination appears.
Chesterfield Heights right now
🟢 Buyer-leaning market. 8.0 months of supply and 0% of the inventory already under contract give buyers above-average negotiating leverage.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 (2 active and pending listings, 3 closed sales in 12 months).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 2, 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
Chesterfield Heights market snapshot (as of September 20, 2026): the median sale price is about $480K ($331 per sq ft over the trailing 12 months of closed sales), a median 2 days on market for closed sales, and 8.0 months of supply, a buyer-leaning market.
In ZIP 33756 (Clearwater), 534 homes closed in the last 12 months at a median of $355K ($257/sq ft), down 1.9% year over year, with a median 45 days on market. Right now 124 active and 24 pending listings put supply at about 4.7 months — a balanced market. See the live ZIP 33756 housing market and the Pinellas County market.
Stellar MLS sales records identify 176 homes in Chesterfield Heights that have changed hands since 2004, built between 1957 and 1980 (median 1960), with a median living area of about 1,426 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.
Chesterfield Heights 1st Add is a small, established Clearwater pocket of 124 mid-century homes in Pinellas County, where the story is renovation history more than square footage.
The setting & the homes.
Aerial and on-site photos of Chesterfield Heights. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Photos from Stellar MLS listings in Chesterfield Heights; content deemed reliable but not guaranteed.
Who Chesterfield Heights is best for.
Best for
- Long-term owners who want a modest single-story footprint and plan to stay put
- Buyers with a renovation budget who can take an original home and modernize systems
- Value hunters willing to wait for the right condition-and-price match
Probably not for
- Buyers who need a wide selection and a fast timeline
- Anyone expecting new-construction square footage or layouts
- Investors relying on frequent turnover and abundant recent comps
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 ($480K) IS the median in the snapshot above.
Windows contain 0 to 7 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 2015 through 2026. Deemed reliable but not guaranteed.
15% of homes for sale in ZIP 33756 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 (2026-10-02).
Chesterfield Heights Market Scorecard
Chesterfield Heights is currently a buyer-leaning market. About 8.0 months of supply, a median asking price of $409,000, and homes go under contract in about 11 days.
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 Chesterfield Heights 1St Add, Clearwater
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 Chesterfield Heights
Live MLS inventory for Chesterfield Heights. 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 Chesterfield Heights listings as of 2026-10-01, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2015 through 2026. Tap any home to ask about it.
Every Home for Sale in Chesterfield Heights 1St Add Right Now (2)
All 2 active and pending Chesterfield Heights 1St Add listings with a detail page, newest first, refreshed twice a day from the MLS.
- 1779 Avon Lane · $414,000 · 3 bd / 2 ba · listed Sep 18, 2026 · listed by Exp Realty Llc
- 1773 London Ln · $399,000 · 3 bd / 2 ba · listed Sep 3, 2026 · listed by Coldwell Banker Realty
Chesterfield Heights 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.
Schools
- Pinellas County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Ponce de Leon Elementary-PN · Elementary
- Largo Middle-PN · Middle
- Largo High-PN · High
Zoned schools reflect the assignments reported on recent Chesterfield Heights listings and can change; always confirm with Pinellas County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Chesterfield Heights address.
Shop the zone: Homes zoned for Largo High-Pn High School
The Chesterfield Heights buying strategy.
If we were buying in Chesterfield Heights 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.
Use your leverage. With inventory sitting, there is room to negotiate on anything dated or overpriced and to ask for repairs or a rate buydown.
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 Chesterfield Heights.
A condition-driven mid-century pocket
The housing stock spans 1956 to 1981, with the bulk clustered near the 1960 median. At a median of roughly 1,491 square feet, these are modest single-story footprints by today's standards, which keeps carrying costs and maintenance scope manageable but rewards smart interior updates. Expect the usual mid-century questions on roof age, electrical panels, and plumbing — the answers to those are where value separates.
The high homestead share, near 80%, signals a neighborhood held for the long haul rather than churned by investors. That tends to mean well-kept exteriors and stable turnover, but it also means fewer homes hit the market in any given season. When one does, the ones that have been thoughtfully modernized are what move; original-condition homes trade on land and potential.
The location and the amenities are priced into every listing in Chesterfield Heights. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a thin-listing, condition-driven market like this, one bad comp read can cost you. We underwrite each home on its own merits — roof, systems, and renovation history — instead of leaning on sparse recent sales, and we tell you plainly when a home is priced for its work-still-needed reality versus its finished one.
Chesterfield Heights 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 Chesterfield Heights 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 Chesterfield Heights sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Chesterfield Heights, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Chesterfield Heights home worth?
Get a no-obligation home value based on real comparable sales in Chesterfield Heights, 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 Clearwater →
Frequently Asked Questions
What is the median home price in Chesterfield Heights?
How long do homes in Chesterfield Heights take to sell?
Is Chesterfield Heights a buyer's or seller's market right now?
Who is the best real estate agent for Chesterfield Heights?
How do I find a top Clearwater real estate agent who knows Chesterfield Heights?
Can Momentum Realty connect me with an agent for Chesterfield Heights?
Where is Chesterfield Heights, and what county is it in?
Should you buy in Chesterfield Heights?
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: October 1, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 20, 2026 |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2015 (28 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 Chesterfield Heights 1St Add fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
Explore more neighborhoods near Chesterfield Heights with Momentum Realty’s local guides.