Glenwood Estates
Homes for Sale in Clearwater, FL

This is a mature Pinellas County neighborhood of roughly 205 homes with deep vintage character and a wide range of ages, so no two blocks feel identical and the condition of any given house matters more than the address.

Stellar MLS sales records identify 31 homes in Glenwood Estates that have changed hands since 2005, built between 1920 and 2016 (median 1955), with a median living area of about 1,980 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 Glenwood Estates across 2024–2025 (9 in 2024, 4 in 2025), median $509,000 — 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.

Glenwood Estates 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 Glenwood Estates 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 Glenwood Estates 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 Glenwood Estates address.

The year-built range here is unusually wide — 1920 to 2016 — with a median build year of 1950. In practice that means original bungalows and mid-century homes sit alongside occasional newer infill. The value question on any purchase is almost always the same: what has been updated, and what still needs to be. Roof age, plumbing, electrical, and windows carry outsized weight in a neighborhood this old.

About 62.5% of homes carry a homestead exemption, which points to a core of long-term owner-occupants and a market that doesn't churn every year. That tends to mean fewer listings at any given moment and homes that come to market having been lived in rather than flipped. Buyers should be ready to move on the right updated property and to budget realistically on the unrenovated ones.

In a neighborhood where price is decided by condition rather than a simple price-per-foot rule, you need someone who will walk the roof, the panel, and the plumbing story with you before you fall for the finishes. We price and negotiate off what a specific home actually is — vintage 1950 original or thoughtfully updated — not off a neighborhood average, and we'll tell you plainly when a listing is asking updated money for un-updated bones.