Chesterfield Heights
Homes for Sale in Clearwater, FL

This is a compact, mostly mid-century enclave in Pinellas County where the housing stock is more uniform in age than in condition. What you pay depends heavily on how much of the original home has been updated.

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.

County records show 6 qualified sales in Chesterfield Heights across 2024–2025 (4 in 2024, 2 in 2025), median $462,000 — 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.

Chesterfield Heights is too small for its own price trend, so here is the market around it.

In ZIP 33756, 260 homes are on the market and 17% are under contract — a slower corner of Clearwater.

Across Pinellas County, 6,539 homes are active and 1,627 pending (20% under contract).

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.

ZIP and county figures describe the wider market, not Chesterfield Heights specifically. Momentum Research analysis of MLS records.

The building span runs from 1958 to 2004, but with a median year built of 1959, the neighborhood reads as predominantly original mid-century construction with a handful of newer infill. Living areas center around 1,444 square feet, so these are modest, single-story-scale homes by today's standards. The variable that separates one sale from the next is roof, systems, and interior updating — not square footage.

About 78% of homes here carry a homestead exemption, which points to a largely owner-occupied street rather than an investor-churned one. That tends to mean homes are held longer and turnover is limited, which is consistent with the thin closing activity in our current window. Buyers should be patient about inventory; sellers should recognize that a well-prepared listing stands out in a market this quiet.

In a low-turnover, condition-driven neighborhood like this, pricing comes down to reading each home individually rather than leaning on a comp average. We walk the systems, weigh what has actually been updated against what still looks original, and tell you plainly where a given house sits on that spectrum. With few recent closings to anchor on, that hands-on read is worth more than any formula.

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.