Chesterfield Heights market snapshot (as of June 25, 2026): the median sale price is about $408K ($276 per sq ft), with homes averaging 79 days on market and 0.8 months of supply, a balanced market (limited data). Based on 15 recent closings in live Stellar MLS data.
Chesterfield Heights is an established single-family neighborhood in Clearwater, Pinellas County, in ZIP 33756, set off South Greenwood Avenue near the Belleair town line (multiple Clearwater real estate and neighborhood guides, 2026). Listing guides describe it as a charming, established community with a home-town feel, built largely between 1957 and 1977.
The housing stock is mid-century single-family homes, generally midsize and reasonably priced, with neighborhood guides citing a range of roughly 950 to 2,600 square feet (Clearwater subdivision guides, 2026). Many are slab-on-grade concrete-block homes typical of the era, so the read is roof age, systems, and renovation condition home by home rather than a uniform builder spec; confirm the exact size, beds, and updates for any specific address.
Because this is an established neighborhood rather than a managed community, listing guides note no HOA and no CDD, which keeps carrying costs simple, while the diligence shifts to the individual home and lot. The drivers are the lot, the era construction, the renovation condition, the flood zone, and the specific location within the neighborhood, all of which have to be read from county records and an inspection for the exact address.
The pitch is an affordable, established address close to the coast: the Gulf beaches at Clearwater Beach and Belleair are a short drive, with shopping, dining, and parks nearby and downtown Clearwater and the broader Pinellas job centers within reach. The work is the diligence: read the era, the systems, and the condition, confirm the FEMA flood zone by parcel, and check the lot before you buy the curb appeal.
