Highland Hill
Homes for Sale in Clearwater, FL
All 1,140 homes for sale in Clearwater, FL · median $284,950 · Pinellas County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 8 closed sales in Highland Hill in Clearwater, FL since 2004, the most recent in August 2026. 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).
Highland Hill in Clearwater doesn't come with a documented amenity package in the current MLS data, and that absence is itself useful information: this reads as a straightforward residential pocket rather than a community built around a clubhouse, gate, or shared recreation. Pricing here is going to be driven by the individual home — lot, layout, condition, updates — rather than by a community fee schedule or amenity premium.
For a buyer, that means due diligence should focus on the property itself and its immediate block rather than assuming a community-wide standard. For a seller, it means the pitch has to be about the house, not the neighborhood brand. Neither posture is a red flag — plenty of solid Pinellas County housing stock sits outside amenitized developments — but it changes how you should shop or price here.
Nearby homes for sale
No active listings inside Highland Hill 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
Highland Hill sits in Clearwater, Pinellas County, and shows no HOA-run or shared community amenities in current MLS listings, which points to a neighborhood valued primarily on individual homes rather than a common amenity package.
Stellar MLS sales records identify 10 homes in Highland Hill that have changed hands since 2004, built between 1961 and 1966 (median 1963), with a median living area of about 1,411 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 Highland Hill is best for.
Best for
- Buyers prioritizing the home itself over community perks or shared facilities
- Buyers comfortable doing direct verification on HOA status and property condition before committing
- Sellers whose home's individual condition and updates are strong enough to stand on their own without a community amenity story
Probably not for
- Buyers set on a gated or clubhouse-anchored community with documented shared amenities
- Buyers who want to rely on published community statistics or amenity comparisons before touring
- Sellers hoping to market a community lifestyle angle rather than the property specifics
The market around Highland Hill
Highland Hill is too small for its own price trend, so here is the market around it.
In ZIP 33756, 258 homes are on the market and 14% are under contract — a slower corner of Clearwater.
Across Pinellas County, 6,628 homes are active and 1,729 pending (21% under contract).
In ZIP 33756 (Clearwater), 546 homes closed in the last 12 months at a median of $355K ($257/sq ft), down 2.2% year over year, with a median 44 days on market. Right now 125 active and 25 pending listings put supply at about 4.8 months — a balanced market. See the live ZIP 33756 housing market and the Pinellas County market.
ZIP and county figures describe the wider market, not Highland Hill specifically. Momentum Research analysis of MLS records.
The Highland Hill buying strategy.
If we were buying in Highland Hill 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 Highland Hill.
A Neighborhood Without a Package
When a community shows no identified amenities in the MLS feed, it usually means one of two things: there genuinely isn't a shared clubhouse, pool, or gated system, or the listings simply haven't been tagging that detail. In either case, buyers shouldn't assume amenity access without verifying it directly with a current listing or the county property record.
That absence also simplifies the value conversation. Without a community fee or amenity tier to price around, what you're paying for in Highland Hill is the home and the lot — condition, square footage, updates, and location within Clearwater relative to the routes and areas you actually use day to day.
The location and the amenities are priced into every listing in Highland Hill. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a neighborhood without a documented amenity structure or a clean statistical snapshot, the work shifts to individual property research — verifying whether any HOA exists, what it does or doesn't cover, and how a specific home's condition stacks up against what's actually moving in Clearwater right now. That's the kind of house-by-house diligence we do before you write an offer or set a list price.
Highland Hill 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 Highland Hill 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 Highland Hill sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Highland Hill, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Highland Hill home worth?
Get a no-obligation home value based on real comparable sales in Highland Hill, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See all homes for sale in Clearwater →
Should you buy in Highland Hill?
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: September 14, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2004 (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.
Looking to buy here? Search homes for sale →
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See how Highland Hill fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Highland Hill
Where is Highland Hill?
Highland Hill is a community in Clearwater, Pinellas County, Florida, ZIP 33756.
Are there homes for sale in Highland Hill right now?
No active listings inside Highland Hill at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Highland Hill have an HOA or CDD?
No HOA is on record for Highland Hill 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.
Nearby Communities
Explore more neighborhoods near Highland Hill with Momentum Realty’s local guides.
Highland Hill Market Scorecard
Highland Hill is currently a no active listings market. Limited supply, a median asking price of n/a.
Typical home value in the 33756 ZIP is $362,892, about 13.6% 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.