Hillcrest
Homes for Sale in Clearwater, FL

Hillcrest Sub 2 Rev is an established Clearwater neighborhood in Pinellas County where the housing stock spans more than a century of construction, from 1920s originals to homes finished as recently as 2023, with a typical living area around 1,659 square feet.

Stellar MLS sales records identify 72 homes in Hillcrest that have changed hands since 2004, built between 1920 and 1996 (median 1950), with a median living area of about 1,573 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 21 qualified sales in Hillcrest across 2024–2025 (13 in 2024, 8 in 2025), median $360,000 — 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.

Hillcrest 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 Hillcrest specifically. Momentum Research analysis of MLS records.

• Skycrest Elementary-PN · Elementary
• Dunedin Highland Middle-PN · Middle
• Clearwater High-PN · High

Zoned schools reflect the assignments reported on recent Hillcrest listings and can change; always confirm with Pinellas County Public Schools for a specific address.

Buying with schools in mind? We can confirm the exact zoned schools for any Hillcrest address.

The defining fact about this community is its age range. A median year built of 1951 puts the typical home solidly in the mid-century category, but the full range — 1920 to 2023 — means shoppers here will encounter everything from unrenovated original construction to full teardown-rebuilds and recent additions. That variance matters more in a neighborhood like this than square footage or lot size, because the condition and update history of any given house can swing its value more than its address does.

At a median living area of roughly 1,659 square feet, homes here skew toward modest, efficient footprints rather than large-format construction — consistent with the neighborhood's mid-century core. With no community amenities identified from current MLS listings, this is a neighborhood defined by its houses and its location within Clearwater, not by shared recreational infrastructure. Buyers should evaluate each property on its own renovation history rather than assuming a uniform standard across the subdivision.

A neighborhood spanning a century of construction with no aggregated amenity package and thin current sales data is exactly where a generic online estimate falls apart. We walk each property's specific age, condition, and renovation history against what is actually happening on the ground in Hillcrest Sub 2 Rev, rather than leaning on a subdivision-wide number that does not exist yet in the current feed.

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