Highland Pines
Homes for Sale in Clearwater, FL

Highland Pines 8Th Add is an older, close-in Clearwater pocket of 281 homes where the housing stock ranges from 1923-era originals to 2022 builds, so the neighborhood reads as a patchwork rather than a single vintage.

Stellar MLS sales records identify 291 homes in Highland Pines that have changed hands since 2004, built between 1950 and 2006 (median 1959), with a median living area of about 1,352 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 13 qualified sales in Highland Pines across 2024–2025 (8 in 2024, 5 in 2025), median $350,000 — 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 Pines 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 Pines specifically. Momentum Research analysis of MLS records.

The defining fact of this community is age spread. A median year built of 1960 anchors it in mid-century construction, but the presence of homes from the 1920s and from as recently as 2022 means you should expect wide variation in systems, layouts, and lot use. Older homes here may carry the usual mid-century considerations — original electrical, plumbing, and roof age — while the newer builds and gut renovations sit at the opposite end. Inspect on the individual house, not on the neighborhood average.

The owner-occupancy share of 53.4% signals a genuinely blended block: a little over half homestead-owned, the rest not. That balance shapes how homes come to market and how they present. Median living area near 1,554 square feet keeps most of this stock in the smaller, more workable range, which is part of what keeps the area accessible relative to larger Pinellas product.

In a neighborhood this varied, the number that matters is the one on the specific house in front of you, not a community average. We underwrite each property on its own condition, vintage, and square footage, price against genuinely comparable sales, and tell you plainly when a listing is priced for its finishes and when it is priced for its potential. That candor is worth more here than in a uniform subdivision.

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