Highland Pines
Homes for Sale in Clearwater, FL

Highland Pines Add is an established Clearwater pocket of 268 homes in Pinellas County, built mostly mid-century, where roughly 70% of owners hold a homestead exemption — a sign of long-term owner occupancy rather than heavy investor churn.

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.

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, 160 homes are on the market and 19% are under contract — a steady corner of Clearwater.

Across Pinellas County, 6,628 homes are active and 1,729 pending (21% under contract).

In ZIP 33755 (Clearwater), 512 homes closed in the last 12 months at a median of $280K ($242/sq ft), down 5.6% year over year, with a median 52 days on market. Right now 57 active and 18 pending listings put supply at about 3.8 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.

With a median year built of 1959 and a range stretching to 2008, this is a neighborhood where two houses on the same street can be a generation apart in systems and finishes. That variance is the single biggest driver of price, so a headline median of $294,950 tells you less than a walkthrough does. Budget for inspection realities — roof, electrical, and plumbing age — and price your offer against the specific home, not the block.

The homestead share near 70% points to a stable, owner-occupied core, and the modest closings window means comps are thin. Thin data and a 62-day median mean pricing is more art than formula here. Sellers who ignore condition sit; buyers who read condition correctly find leverage.

In a thin-comp, condition-driven market like this one, the gap between a fair price and an overpaid one is renovation math, not a lookup table. We walk the home with you, weigh the mid-century systems against the asking price, and set an offer or a list number grounded in what the property actually is — not a rounded median.

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