Hillcrest Estates
Homes for Sale in Clearwater, FL

All 1,178 homes for sale in Clearwater, FL · median $299,000 · 39 homes for sale in 33765 · Pinellas County homes for sale

Community in Clearwater · Pinellas County · ZIP 33765
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Built fromLive Stellar MLS data21 years of closingsUpdated twice daily

As of September 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, 1,358 homes closed in the last 12 months at a median of $312,500, 50 median days on market, with 415 homes for sale today. At that median and Pinellas County's FY2025-26 rate of 19.39 mills, annual property tax runs about $6,060 ($5,250 with the full homestead exemption).

Live · Hillcrest Estates Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 10,000+ customers served · Top 1% in Florida (RealTrends)
Tempo
0 · 0
For sale · pending
live counts, refreshed twice daily
Jon Brooks, founder of Momentum Realty
Jon's Current Read

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.

Nearby homes for sale

No active listings inside Hillcrest EstatesHomes for Sale in Clearwater, FL 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.

920 LAKE FOREST ROAD
$620K · 0.1 mi away
4 bd · 2 ba · 2,270 sqft
920 LAKE FOREST ROAD
Listed by KELLER WILLIAMS REALTY- PALM HARBOR
921 COLLEGE HILL DRIVE
$1M · 0.2 mi away
4 bd · 3.5 ba · 4,391 sqft
921 COLLEGE HILL DRIVE
Listed by MARK SPAIN REAL ESTATE
731 OBERLIN DRIVE
$519K · 0.2 mi away
3 bd · 2 ba · 1,811 sqft
731 OBERLIN DRIVE
Listed by RE/MAX ACTION FIRST OF FLORIDA
2212 NE COACHMAN ROAD
$475K · 0.3 mi away
3 bd · 2 ba · 1,772 sqft
2212 NE COACHMAN ROAD
Listed by PAM RYAN REALTY INC
2280 MACKENZIE COURT
$1.95M · 0.3 mi away
5 bd · 5.5 ba · 5,256 sqft
2280 MACKENZIE COURT
Listed by KELLER WILLIAMS REALTY PORTFOLIO COLLECTION
2 N FERNWOOD AVENUE #25
$108K · 0.5 mi away
2 bd · 1 ba · 800 sqft
2 N FERNWOOD AVENUE #25
Listed by RE/MAX ELITE REALTY

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.

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, 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 6.6% year over year, with a median 50 days on market. Right now 29 active and 6 pending listings put supply at about 4.8 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.

If we were buying in Hillcrest Estates today, this is the order of operations we would run for our clients.

1

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.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

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.

Best Buy
Buyers who want an established Clearwater address with a mid-century home rather than new construction.
Biggest Risk
Condition variance is high — homes built between 1957 and 1985 can differ enormously in what has and has not been updated.
Sweet Spot
A buyer who has already budgeted for updates and wants space — the median living area here runs over 2,100 square feet.
Avoid If
You are looking for a community with organized amenities or a homogenous, newly built streetscape.

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.

Jon Brooks · Founder, Momentum Realty

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.

Best forBuyers who want an established Clearwater address with a mid-century home rather than new construction.
Biggest advantageNo HOA structure identified, which keeps ongoing costs simpler and more predictable.
Biggest riskCondition variance is high — homes built between 1957 and 1985 can differ enormously in what has and has not been updated.
Sweet spotA buyer who has already budgeted for updates and wants space — the median living area here runs over 2,100 square feet.
Avoid ifYou are looking for a community with organized amenities or a homogenous, newly built streetscape.

HOA, CDD & Fees

A note on who we are: Momentum Realty is a real estate brokerage. We are not the Hillcrest Estates homeowners association, its management company or its developer, and we cannot help with dues, gate access, violations, amenity bookings or association documents. To reach the association, check your closing package, the recorded declaration at the county clerk, or search the association’s name at sunbiz.org for its registered agent. Call or message us to buy or sell a home in Hillcrest Estates.
In short
  • 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.

The takeaway

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.

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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Real comps, not an automated estimate.
Buyers comfortable evaluating an older home's condition and budgeting for updates as neededExcellent fit
Buyers who want more living area than typical new construction offers, without amenity fees attachedExcellent fit
Buyers targeting a settled, low-turnover Pinellas County location over a fast-growing new subdivisionExcellent fit
Buyers who want a warrantied, move-in-ready new build with no renovation riskProbably not
Buyers who specifically want HOA-run amenities such as a pool or clubhouse includedProbably not
Buyers expecting a large, active resale market with frequent listing turnoverProbably not

Data sources & freshness

Live listingsStellar MLS, refreshed twice daily (last: September 12, 2026)
Under-contract sharesStellar MLS records, as of 2026-09-08
Historical depthClosed-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.

Own a home here?

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.

More on Hillcrest Estates

Nearby Communities

Explore more neighborhoods near Hillcrest Estates with Momentum Realty’s local guides.

CHCoachman Hill Preserve0.2 mi away · 11 homes, built 2001–19, 1 for saleCHCollege Hill Estates0.2 mi away · 54 homes, built 1957–85, 1 for salePTPalmetto Terrace0.2 mi away · 82 homes, built 1950–88, 1 for saleVEVarsity Estates0.2 mi away · 12 homes, built 2010–10RHRolling Heights0.3 mi away · median $530K, 4 sales/12 moCHCoachman Hill Estates0.3 mi away · 22 homes, built 1977–13ETEastwood Terrace0.5 mi away

Browse all neighborhood guides →

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Hillcrest Estates Market Scorecard

No active listings

Hillcrest Estates is currently a no active listings market. Limited supply, a median asking price of n/a.

n/a
Months supply
n/a
Median list
$513,000
Median sold
n/a
Per sqft
n/a
Days on mkt
0/0/2
Active/Pend/Sold

Typical home value in the 33765 ZIP is $354,448, about 14.8% above the Florida norm (Zillow Home Value Index).

Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.

Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.