Highland Lake
Homes for Sale in Clearwater, FL

A compact, long-held enclave in central Pinellas where the housing stock skews mid-century, with a scattering of earlier and later builds — the kind of place where the home itself, not the address, drives value.

Stellar MLS sales records identify 140 homes in Highland Lake that have changed hands since 2004, built between 1951 and 2002 (median 1956), with a median living area of about 1,346 sq ft and a typical 3-bedroom, 2-bath layout; 99% 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 11 qualified sales in Highland Lake across 2024–2025 (6 in 2024, 5 in 2025), median $390,000 — 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 Lake is too small for its own price trend, so here is the market around it.

In ZIP 33756, 258 homes are on the market and 14% are under contract — a slower corner of Clearwater.

Across Pinellas County, 6,628 homes are active and 1,729 pending (21% 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 Highland Lake specifically. Momentum Research analysis of MLS records.

The 1915-to-2005 build range inside just 209 homes is unusual for a subdivision this size. Practically, you'll find original mid-century houses next to earlier structures and the occasional newer infill, which keeps floor plans, systems, and finish levels all over the map. That variety is an opportunity for a buyer willing to read a house carefully, and a reason to expect a wide spread between a dated original and a fully updated comparable.

At a median of roughly 1,500 living square feet, these are right-sized homes rather than sprawling ones. Older housing rewards diligence: roof, electrical, plumbing, and permit history matter more than curb impression here, and they are where negotiating leverage tends to live for both sides.

In a low-turnover, condition-driven pocket like this, the median tells you almost nothing about what a specific house should trade for. We price and evaluate off the home in front of us — its updates, systems, and permit trail against the handful of relevant recent sales — so buyers don't overpay for cosmetics and sellers don't leave real renovation value on the table.

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