Highland Pines
Homes for Sale in Clearwater, FL
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 19 closed sales in Highland Pines Add in Clearwater, FL since 2012, the most recent in January 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 by a uniform product. With homes built across a span that runs from the 1920s to the early 2020s and a median year built of 1960, you are looking at a neighborhood where two houses on the same street can be worlds apart: one an original mid-century cottage, the next a full renovation or a newer infill build. That spread is the single biggest variable in what a home trades for, so square footage and finish level matter more than any headline average.
The median living area sits at roughly 1,554 square feet, which tells you this is a market of modest-footprint homes rather than sprawling ones. For buyers, that means the opportunity is in the delta between a dated house and an updated one. For sellers, it means the work you have or have not done shows up directly in the number. With owner-occupancy just over half at 53.4%, there is a real mix of long-held homes and rental or investor-held stock, which keeps inventory character varied.
The 60-Second Overview
Highland Pines Add is an older, close-in Clearwater pocket of 281 homes where the housing stock ranges from 1923-era originals to 2022 builds, so the neighborhood reads as a patchwork rather than a single vintage.
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 Pines is best for.
Best for
- Renovation-minded buyers who want to build value through work on a smaller, mid-century home
- Budget-conscious buyers seeking a close-in Clearwater footprint under the larger-home price tier
- Investors comfortable operating in a mixed owner-occupied and rental block
Probably not for
- Buyers who want move-in-ready, new construction with no deferred maintenance
- Anyone needing large square footage well above the roughly 1,554-square-foot median
- Buyers who want the uniformity and predictable comps of a single-vintage subdivision
The market around Highland Pines
Highland Pines is too small for its own price trend, so here is the market around it.
In ZIP 33755, 160 homes are on the market and 19% are under contract — a steady 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 Pines specifically. Momentum Research analysis of MLS records.
The Highland Pines buying strategy.
If we were buying in Highland Pines 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 Pines.
A condition-driven market, not a cookie-cutter one
The defining fact of this community is age spread. A median year built of 1960 anchors it in mid-century construction, but the presence of homes from the 1920s and from as recently as 2022 means you should expect wide variation in systems, layouts, and lot use. Older homes here may carry the usual mid-century considerations — original electrical, plumbing, and roof age — while the newer builds and gut renovations sit at the opposite end. Inspect on the individual house, not on the neighborhood average.
The owner-occupancy share of 53.4% signals a genuinely blended block: a little over half homestead-owned, the rest not. That balance shapes how homes come to market and how they present. Median living area near 1,554 square feet keeps most of this stock in the smaller, more workable range, which is part of what keeps the area accessible relative to larger Pinellas product.
The location and the amenities are priced into every listing in Highland Pines. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a neighborhood this varied, the number that matters is the one on the specific house in front of you, not a community average. We underwrite each property on its own condition, vintage, and square footage, price against genuinely comparable sales, and tell you plainly when a listing is priced for its finishes and when it is priced for its potential. That candor is worth more here than in a uniform subdivision.
Highland Pines 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 Pines 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 Pines sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Highland Pines, 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 Pines home worth?
Get a no-obligation home value based on real comparable sales in Highland Pines, 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 Highland Pines?
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 2012 (19 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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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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