Highland Pines
Homes for Sale in Clearwater, FL

A 158-home pocket of Clearwater built out mostly in the 1950s, Highland Pines Add carries a median living area of 1,548.5 sq ft on a mix of original and later-built homes, with no shared community amenities identified in current MLS listings.

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.

The 1950-to-2001 build span in Highland Pines Add means due diligence starts with the permit and renovation history of the specific address, not the neighborhood average. A home from the original 1958 wave that hasn't been updated will show its age in systems and layout; a later-built or substantially renovated home on the same block can feel like a different product entirely. Buyers should expect to evaluate each listing on its own condition rather than assume consistency across the plat.

There's no HOA or listed community amenity package here, so whatever draws a buyer to Highland Pines Add is the location and the individual lot, not shared recreation or maintained common areas. That also means fewer recurring fees and more owner discretion over the property, which suits buyers who want control over their home's condition and use rather than a managed, amenity-driven setting.

In a neighborhood this age-mixed, the difference between a fair offer and an overpay comes down to reading each home's actual condition and update history against what's currently active and pending nearby. We walk that comparison line by line before you write an offer, and we do the same work in reverse for sellers pricing a home that needs to stand out against both original-condition and renovated neighbors.

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