Highland Estates Of Clearwater
Homes for Sale in Clearwater, FL

Highland Estates Of Clearwater is an established, mid-century-rooted community in Pinellas County where the homes are compact and the range of build years is unusually broad for a single area.

Stellar MLS sales records identify 50 homes in Highland Estates Of Clearwater that have changed hands since 2011, built between 1958 and 2013 (median 1965), with a median living area of about 1,422 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 14 qualified sales in Highland Estates Of Clearwater across 2024–2025 (10 in 2024, 4 in 2025), median $369,000 — 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.

Highland Estates Of Clearwater is too small for its own price trend, so here is the market around it.

In ZIP 33755, 163 homes are on the market and 23% are under contract — a steady corner of Clearwater.

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

In ZIP 33755 (Clearwater), 513 homes closed in the last 12 months at a median of $280K ($242/sq ft), down 4.7% year over year, with a median 52 days on market. Right now 64 active and 23 pending listings put supply at about 3.5 months — a balanced market. See the live ZIP 33755 housing market and the Pinellas County market.

ZIP and county figures describe the wider market, not Highland Estates Of Clearwater specifically. Momentum Research analysis of MLS records.

With 318 homes and a build range running from 1936 to 2023, the area doesn't read as one product type. The median year built of 1961 tells you the core is mid-century, but scattered newer construction and rebuilds sit alongside original homes. Expect to evaluate each property on its own merits rather than assuming a neighborhood-wide standard.

The median living area of about 1,504 square feet keeps most homes in efficient, single-story territory. Roughly 68% carry homestead status, which suggests a stable ownership base and relatively measured turnover. Both facts reward buyers who do their homework on systems, roof, and past updates, because the gap between a refreshed home and a dated one is where value is won or lost here.

In a community this varied — homes from 1936 to 2023, a median build year of 1961, and a wide condition-driven price spread — the number that matters is the one on the specific house in front of you, not a neighborhood average. We price and inspect property by property, tell you what's been updated versus what's cosmetic, and walk away from deals that don't hold up. That's the only honest way to buy or sell where no two homes are the same.

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