Hillcrest Estates
Homes for Sale in Clearwater, FL
All 1,140 homes for sale in Clearwater, FL · median $285,000 · 32 homes for sale in 33765 · Pinellas County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 11 closed sales in Hillcrest Estates 1St Add Pt Rep in Clearwater, FL since 2015, the most recent in December 2025. Across Clearwater as a whole, 1,267 homes closed in the last 12 months at a median of $315,000, 49 median days on market, with 393 homes for sale today. At that median and Pinellas County's FY2025-26 rate of 19.39 mills, annual property tax runs about $6,110 ($5,290 with the full homestead exemption).
Price here is driven by condition, not floor plan. With homes built between 1955 and 1990 and a median build year of 1969, you are looking at a market where two houses of similar size can trade very differently depending on roof, systems, and how much updating has already been done. The median living area sits near 1,955 square feet, so most of these are usable mid-size homes rather than teardowns or estates.
The high homestead share — roughly 78% of homes — tells you this is a hold-and-live neighborhood, not an investor churn. That tends to mean fewer listings hit the market at once and sellers are rarely in a hurry. Buyers should expect to move on the right updated home when it appears; sellers should price to condition honestly, because the buyer pool here compares closely.
Nearby homes for sale
No active listings inside Hillcrest Estates 1St Add Pt Rep 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 Rep is a small, established Clearwater community of about 91 homes in Pinellas County, weighted toward owner-occupants and mid-century-through-1990 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
- Long-term owner-occupants who want to buy, settle, and hold in an established Pinellas pocket
- Buyers with a renovation budget who can add value to an older home through systems and updates
- Those prioritizing a mid-size single-family home near 1,955 square feet over new-build finishes
Probably not for
- Buyers who need a brand-new or recently built home
- Short-horizon flippers relying on high inventory and fast turnover
- Anyone unwilling to weigh inspection findings and deferred maintenance on an older home
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, 48 homes are on the market and 21% 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 33765 (Clearwater), 120 homes closed in the last 12 months at a median of $368K ($238/sq ft), up 6.1% year over year, with a median 50 days on market. Right now 24 active and 6 pending listings put supply at about 4.5 months — a balanced market. 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.
An owner-held mid-century pocket
At 91 homes with a build range spanning 1955 to 1990, this is an infill neighborhood that filled in over several decades rather than all at once. That mix matters: an early-era ranch and a late-1980s build can sit on the same street with different structures, systems, and update needs, which is exactly why condition dictates value more than square footage here.
The median size near 1,955 square feet points to practical, full-size single-family homes. With homesteading around 78%, turnover is low and the homes that do sell are often ones that have been lived in and maintained for years — so inspection findings and deferred-maintenance judgment calls are where deals are won or lost.
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 low-turnover community where price hinges on condition rather than a published range, our value is telling you what a specific roof, system, or renovation is actually worth against recent local closings. With only a thin window of sales to read, we help sellers price to reality and help buyers avoid overpaying for cosmetic updates over structural ones.
Hillcrest Estates in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- Any club/amenity membership is billed separately
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
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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Should you buy in Hillcrest Estates?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2015 (11 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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You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
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Common questions about Hillcrest Estates
Where is Hillcrest Estates?
Hillcrest Estates is a community in Clearwater, Pinellas County, Florida, ZIP 33765.
Are there homes for sale in Hillcrest Estates right now?
No active listings inside Hillcrest Estates at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Hillcrest Estates have an HOA or CDD?
No HOA is on record for Hillcrest Estates in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.
Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.
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