Hillcrest Estates
Homes for Sale in Clearwater, FL
All 1,299 homes for sale in Clearwater, FL · median $318,888 · 39 homes for sale in 33765 · Pinellas County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Stellar MLS
As of November 2026, the MLS records 8 closed sales in Hillcrest Estates in Clearwater, FL since 2005, the most recent in February 2026. Across Clearwater as a whole, 2,252 homes closed in the last 12 months at a median of $320,000, 46 median days on market, with 1,141 homes for sale today. At that median and Pinellas County's FY2025-26 rate of 19.39 mills, annual property tax runs about $6,200 ($5,390 with the full homestead exemption).
Hillcrest Estates is a small, established pocket of 48 homes built between 1957 and 1985, with a median build year of 1969. That age range means pricing here tracks condition and updates more than square footage — two homes with similar layouts can sit far apart in list price depending on whether the roof, kitchen, or systems have been touched.
With roughly 77% of homes carrying a homestead exemption, turnover tends to be slower and inventory thinner than in newer subdivisions nearby. For buyers, that means patience — listings do not cycle quickly, and being ready to move when the right one appears matters more than trying to time the market.
Figures in this note are as of July 21, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Nearby homes for sale
No active listings inside Hillcrest Estates right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Hillcrest Estates is a compact, mid-century Clearwater neighborhood where the housing stock — median living area of 2,122 square feet — skews toward established, single-story layouts rather than newer construction.
Stellar MLS sales records identify 31 homes in Hillcrest Estates that have changed hands since 2010, built between 1961 and 1990 (median 1969), with a median living area of about 2,199 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.
Who Hillcrest Estates is best for.
Best for
- Buyers comfortable evaluating an older home's condition and budgeting for updates as needed
- Buyers who want more living area than typical new construction offers, without amenity fees attached
- Buyers targeting a settled, low-turnover Pinellas County location over a fast-growing new subdivision
Probably not for
- Buyers who want a warrantied, move-in-ready new build with no renovation risk
- Buyers who specifically want HOA-run amenities such as a pool or clubhouse included
- Buyers expecting a large, active resale market with frequent listing turnover
The market around Hillcrest Estates
Hillcrest Estates is too small for its own price trend, so here is the market around it.
In ZIP 33765, 54 homes are on the market and 22% 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 33765 (Clearwater), 21 homes closed in the last 12 months at a median of $345K ($287/sq ft), with a median 37 days on market. Right now 10 active and 3 pending listings. See the live ZIP 33765 housing market and the Pinellas County market.
ZIP and county figures describe the wider market, not Hillcrest Estates specifically. Momentum Research analysis of MLS records.
The Hillcrest Estates buying strategy.
If we were buying in Hillcrest Estates today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Hillcrest Estates.
A neighborhood defined by its age, not its size
With only 48 homes and a build range spanning nearly three decades (1957 to 1985), Hillcrest Estates does not behave like a large, homogenous subdivision. Each home's story — original systems versus renovated, additions versus untouched footprint — plays a bigger role in valuation than it would in a newer community where every house is close to identical.
There is no HOA or community amenity package identified in current MLS listings, which keeps carrying costs simpler but also means buyers are not paying for shared pools, gates, or clubhouses. What you are buying is the lot, the structure, and its position inside a settled Pinellas County street grid — not a bundled lifestyle package.
The location and the amenities are priced into every listing in Hillcrest Estates. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a small, older neighborhood like this, the difference between a fair offer and an overpay is almost always in the details — permit history, age of major systems, and how a specific home's condition stacks up against the last few comparable closings. We walk that ground before we talk numbers, not after.
Hillcrest Estates in 15 seconds.
Tools for a Hillcrest Estates buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Hillcrest Estates sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Hillcrest Estates, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Hillcrest Estates home worth?
Get a no-obligation home value based on real comparable sales in Hillcrest Estates, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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Housing distress & ownership in Hillcrest Estates, Clearwater
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period November 2026 through November 2026. Deemed reliable but not guaranteed.
Email me new listings in Hillcrest Estates
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Hillcrest Estates
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Hillcrest Estates will answer, and the answer is published on this page for the next buyer.
Frequently Asked Questions
How many homes are in Hillcrest Estates?
What share of Hillcrest Estates is owner-occupied?
When were the homes in Hillcrest Estates built?
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Where is Hillcrest Estates, and what county is it in?
Should you buy in Hillcrest Estates?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: November 7, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (1 streets, ZIP 33765)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2005 (8 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
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See how Hillcrest Estates fits the bigger picture — live prices, inventory, and Momentum Scores: