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 11 closed sales in Highland Pines Add in Clearwater, FL since 2012, the most recent in March 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).
This is an older Clearwater pocket where the housing stock was largely built between 1950 and 2001, with the middle of the range sitting in the late 1950s. At that age, price here is driven far less by any headline number and far more by condition: what has been updated, what still needs work, and how the roof, systems, and layout have held up over the decades. Expect a wide spread between a tired original home and one that has been reworked, even on similar lots.
With 117 homes and a homestead share near two-thirds, this is a settled, owner-occupied enclave rather than a churn-heavy investor block. For a buyer, that means turnover is limited and you compete on readiness when a well-kept home lists. For a seller, the mid-1500s square-foot median gives you a functional, right-sized footprint to work with — condition and honest pricing, not square footage claims, will carry the sale.
The 60-Second Overview
Highland Pines Add is a small, established Clearwater neighborhood of mid-century-era homes, mostly owner-occupied, where the value story is about the individual house rather than a uniform product type.
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
- Buyers wanting an established Clearwater address and willing to budget for updates on an older home
- Right-sizers looking for a compact, roughly 1,500-square-foot footprint rather than a sprawling floor plan
- Long-hold owner-occupants comfortable in a low-turnover, mostly homesteaded neighborhood
Probably not for
- Anyone set on new or near-new construction with modern systems throughout
- Buyers needing large square footage or open, contemporary layouts
- Investors chasing high rental turnover in a predominantly owner-occupied pocket
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.
An older pocket where condition is the price
The build window runs from 1950 to 2001, but the median year built lands in 1958 — so most of what trades here carries mid-century bones. That is not a knock; it means block, layout, and lot character can be genuine, but it also means you underwrite roof age, electrical, plumbing, and any additions carefully. A median living area around 1,515 square feet points to compact, single-level-friendly footprints rather than sprawling floor plans.
A homestead share of about 65% tells you this is a hold-and-live community more than a rental play. Inventory tends to be thin, so when something updated comes to market it can move; when something dated lists, it sits until the price reflects the work it needs. Read every listing through that lens — the number on the sheet means little until you know what has and hasn't been touched.
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 small, older neighborhood like this, the difference between a good buy and an expensive mistake is knowing which homes have had real system and roof work and which are wearing cosmetic paint over deferred maintenance. We walk it with you, pressure-test condition against ask, and tell you plainly when a home is priced for its updates or priced on hope.
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.
Nearby Communities
Explore more neighborhoods near Highland Pines 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 2012 (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.
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See how Highland Pines Add fits the bigger picture — live prices, inventory, and Momentum Scores:
Highland Pines Add Market Scorecard
Highland Pines Add is currently a no active listings market. Limited supply, a median asking price of n/a.
Typical home value in the 33755 ZIP is $342,659, about 15.2% 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.