Highland Lake
Homes for Sale in Clearwater, FL
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 11 closed sales in Highland Lake Add in Clearwater, FL since 2014, the most recent in April 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).
Part of Highland Lake Add, Clearwater, FL — see all Highland Lake Add homes for sale (3 listings across 5 sections in the MLS).
Highland Lake Sub 4th Add is a small, established pocket of Clearwater — 209 homes with a median build year of 1959 and a footprint that spans from 1915 all the way to 2005. That range tells you most of what you need to know about pricing: this is a condition-driven market, not a spec-sheet market. Two homes on the same street can trade very differently depending on what has been touched since the mid-century, so the median living size of roughly 1,500 square feet is a starting point, not a rule.
With about 72% of homes held as homesteads, turnover here tends to be measured rather than churning. For a buyer, that means inventory is thin and you compete on readiness and terms when the right home lists. For a seller, it means the comps are less about the neighborhood average and more about how your specific renovation and lot stack up against whatever else is standing at the moment.
The 60-Second Overview
A compact, long-held enclave in central Pinellas where the housing stock skews mid-century, with a scattering of earlier and later builds — the kind of place where the home itself, not the address, drives value.
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 Lake is best for.
Best for
- Buyers seeking a right-sized primary home around 1,500 square feet in an established setting
- Renovation-minded buyers who can read an older house and add value through updates
- Long-hold buyers who value low turnover and are patient enough to wait for the right listing
Probably not for
- Buyers who need move-in-ready new construction with modern systems throughout
- Buyers requiring large square footage or open, contemporary floor plans
- Buyers who want a wide, always-available inventory to choose from on short notice
The market around Highland Lake
Highland Lake 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).
ZIP and county figures describe the wider market, not Highland Lake specifically. Momentum Research analysis of MLS records.
The Highland Lake buying strategy.
If we were buying in Highland Lake 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 Lake.
A mid-century core with a wide age spread
The 1915-to-2005 build range inside just 209 homes is unusual for a subdivision this size. Practically, you'll find original mid-century houses next to earlier structures and the occasional newer infill, which keeps floor plans, systems, and finish levels all over the map. That variety is an opportunity for a buyer willing to read a house carefully, and a reason to expect a wide spread between a dated original and a fully updated comparable.
At a median of roughly 1,500 living square feet, these are right-sized homes rather than sprawling ones. Older housing rewards diligence: roof, electrical, plumbing, and permit history matter more than curb impression here, and they are where negotiating leverage tends to live for both sides.
The location and the amenities are priced into every listing in Highland Lake. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a low-turnover, condition-driven pocket like this, the median tells you almost nothing about what a specific house should trade for. We price and evaluate off the home in front of us — its updates, systems, and permit trail against the handful of relevant recent sales — so buyers don't overpay for cosmetics and sellers don't leave real renovation value on the table.
Highland Lake 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 Lake 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 Lake sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Highland Lake, 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 Lake home worth?
Get a no-obligation home value based on real comparable sales in Highland Lake, 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 Lake?
An honest fit check. We will tell you when it is not your community.
Nearby Communities
Explore more neighborhoods near Highland Lake with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 12, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2014 (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.
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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A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Highland Lake Add fits the bigger picture — live prices, inventory, and Momentum Scores:
Highland Lake Add Market Scorecard
Highland Lake Add 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.