Pine Oak
Homes for Sale in Clearwater, FL

A compact enclave of mid-century and later single-family homes in Clearwater, where median living space of about 1,700 square feet points to modest, functional footprints rather than sprawling new construction. What you're buying here is location and bones, not builder polish.

Stellar MLS sales records identify 62 homes in Pine Oak that have changed hands since 2004, built between 1954 and 1987 (median 1958), with a median living area of about 1,478 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 6 qualified sales in Pine Oak across 2024–2025 (4 in 2024, 2 in 2025), median $525,000 — 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.

Pine Oak is too small for its own price trend, so here is the market around it.

In ZIP 33756, 260 homes are on the market and 17% are under contract — a slower corner of Clearwater.

Across Pinellas County, 6,539 homes are active and 1,627 pending (20% 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 Pine Oak specifically. Momentum Research analysis of MLS records.

The construction window runs four decades, from 1954 to 1995, but the median year built lands in the late 1950s — so most of what trades here is genuinely mid-century in age. Practically, that means budgeting for the things older homes need: roof age, electrical and plumbing updates, and windows. It also means original 1,700-square-foot layouts that reward a buyer willing to reconfigure rather than one expecting open-concept out of the box.

The high homestead share signals long ownership tenure, which tends to produce two kinds of listings: homes that have been thoughtfully maintained and updated over years, and homes that are essentially time capsules. Pricing separates the two, and reading condition accurately is the whole game. This is a neighborhood where a careful inspection and a realistic renovation number matter more than the headline list price.

In a 92-home neighborhood with thin turnover, the difference between overpaying and buying well comes down to reading condition against comparable sales — not chasing a nonexistent price range. We price and vet Pine Oak 1st Add homes on their actual bones: roof, systems, and how much the floor plan has been modernized. That's the analysis that protects a buyer and positions a seller.

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