CHESTERFIELD HEIGHTS 2ND ADD
Homes for Sale in CLEARWATER, FL

CHESTERFIELD HEIGHTS 2ND ADD is a small community — 12 recorded sales on file, most recently in 2025 — too few for its own price trend. Here is the market around it.

In ZIP 33756, 264 homes are on the market and 16% are under contract — a slower corner of CLEARWATER.

Across Pinellas County, 6,999 homes are active and 1,872 pending (21% under contract).

Homes here are single family residence.

ZIP and county figures describe the wider market, not CHESTERFIELD HEIGHTS 2ND ADD 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.