Highland Pines
Homes for Sale in Clearwater, FL
All 1,157 homes for sale in Clearwater, FL · median $299,000 · 138 homes for sale in 33755 · Pinellas County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of October 2026, the MLS records 3 closed sales in Highland Pines 9Th Add in Clearwater, FL since 2014, the most recent in January 2019. 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).
Highland Pines 9th Add is a platted section within Clearwater's broader Highland Pines area, and the current MLS snapshot shows no community amenities tied to active listings — this reads as a straightforward, non-amenitized residential plat rather than a managed or HOA-run community.
With no pricing or activity data surfacing in this snapshot, the honest posture right now is to treat this as a wait-and-see pocket: any buyer or seller move here should lean on a direct comparable pull for the specific street or block rather than a community-wide average, since the plat itself is too granular for broad trend claims.
Nearby homes for sale
No active listings inside Highland PinesHomes 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.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Highland Pines 9th Add is a specific platted section of Clearwater in Pinellas County; current MLS data does not show any identified community amenities attached to listings here, suggesting it functions as a standard residential subdivision without shared recreational infrastructure.
Stellar MLS sales records identify 291 homes in Highland Pines that have changed hands since 2004, built between 1950 and 2006 (median 1959), with a median living area of about 1,352 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 Pines is best for.
Best for
- A buyer focused on a specific Clearwater plat rather than a broader amenity-driven community
- Someone comfortable verifying home features and lot specifics directly rather than relying on package amenities
- A buyer prioritizing location within Pinellas County over shared recreational infrastructure
Probably not for
- A buyer who wants a maintained community pool, clubhouse, or organized common areas
- Someone who needs current pricing benchmarks before making an offer decision
- A buyer who prefers a large, well-documented sales history to model value trends
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).
In ZIP 33755 (Clearwater), 513 homes closed in the last 12 months at a median of $280K ($242/sq ft), down 4.7% year over year, with a median 52 days on market. Right now 64 active and 23 pending listings put supply at about 3.5 months — a balanced market. See the live ZIP 33755 housing market and the Pinellas County market.
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 Plat, Not a Package
The '9th Add' in the name signals this is one phase of a larger platting history for Highland Pines, which typically means lot sizes, home ages, and architectural style were set in a single build-out period rather than accumulated over decades of infill. That consistency can simplify comparisons between homes within the plat, but it also means the plat's character is tied closely to when that phase was developed.
Because no amenities are identified from current listings, buyers should not assume a pool, clubhouse, or maintained common area comes with the address — verify directly with any specific listing or the county property record rather than assuming standard subdivision perks apply.
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
A plat this specific rewards agents who pull data at the plat level instead of relying on Clearwater-wide averages — we build the comparable set street by street so pricing conversations are grounded in what actually sits within Highland Pines 9th Add, not a citywide blend.
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.
See all homes for sale in Clearwater →
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 2014 (3 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:
Schools serving nearby communities
We do not have a confirmed school assignment for Highland Pines. These are the public schools most often assigned to other communities in ZIP 33755; zones change and vary by address, so confirm with the district before you buy.
- Clearwater High · Public · FLDOE grade A (assigned to 3 nearby communities)
- Skycrest Elementary · Public · FLDOE grade A (assigned to 2 nearby communities)
- Clearwater High School · High · FLDOE grade A (assigned to 2 nearby communities)
Assignments from district data for neighboring communities; grades are official Florida Department of Education school grades (2025-26).
Common questions about Highland Pines
Where is Highland Pines?
Highland Pines is a community in Clearwater, Pinellas County, Florida, ZIP 33755.
Are there homes for sale in Highland Pines right now?
No active listings inside Highland Pines 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 Pines have an HOA or CDD?
No HOA is on record for Highland Pines 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 Pines with Momentum Realty’s local guides.