Highland Pines
Homes for Sale in Clearwater, FL
All 1,140 homes for sale in Clearwater, FL · median $285,000 · 96 homes for sale in 33755 · Pinellas County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
Over the 12 months ending 2026-09-12, 6 recorded sales closed at a median of $375,000, $238 per square foot, a median 34 days on market, sellers accepting 97% of original asking (-15% versus the prior year). Homes listed or recently sold were built 1956 - 1976. At the median price and Pinellas County's FY2025-26 rate of 19.39 mills, annual property tax runs about $7,270 ($6,460 with the full homestead exemption).
Highland Pines 5th Add is an older Clearwater subdivision - median year built 1959, with homes ranging as far back as 1950 and as recent as 2022 mixed into the same 324-home footprint. That spread means condition, not square footage or lot size, is doing most of the work on price here. A untouched 1959 original and a gut-renovated version two streets over can post very different numbers even though both carry the same address and lot pattern.
With zero active listings as of this snapshot and a market heat score of 24, there is effectively nothing to compare against in real time - the recent closings (8 in the window) are the only read we have. A median 72-day time on market before those closings suggests pricing right the first time matters more than chasing the market down later. For sellers, that argues for a condition-based pricing conversation up front; for buyers, it means patience and a standing offer strategy, because the next listing may not appear for a while.
Highland Pines right now
🔴 Off the recent peak. The trailing-12-month median ($375K) is down 15.3% from the prior 12 months ($442K). With about 4 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending September 12. Confidence: Low (6 and 4 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 15, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
Nearby homes for sale
No active listings inside Highland Pines 5Th Add 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 market snapshot (as of September 12, 2026): the median sale price is about $375K ($238 per sq ft over the trailing 12 months of closed sales), and a median 35 days on market for closed sales. The trailing-12-month median is down 15% from the prior 12 months, computed from record-level Stellar MLS closed sales (6 closings in the current window).
In ZIP 33755 (Clearwater), 512 homes closed in the last 12 months at a median of $280K ($242/sq ft), down 5.6% year over year, with a median 52 days on market. Right now 57 active and 18 pending listings put supply at about 3.8 months - a balanced market. See the live ZIP 33755 housing market and the Pinellas County market.
Highland Pines is a community of 66 homes in Clearwater, Pinellas County, built between 1954 and 1985 (median 1957.0), with a median living area of about 1,350 square feet. 67% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
A small, established Clearwater pocket where most homes date to the late 1950s but renovation and newer construction have crept in over the decades, producing a market that trades on condition more than location within the neighborhood.
Who Highland Pines is best for.
Best for
- A buyer targeting a lower entry price point in Pinellas County who is willing to renovate or has already budgeted for updates to an older home.
- A buyer prioritizing a smaller, efficient floor plan (median 1,426 sqft) over maximum square footage.
- A patient buyer willing to wait for the right listing to surface rather than needing to choose from active inventory today.
Probably not for
- A buyer who wants a community with organized amenities like a clubhouse or pool - none are identified here.
- A buyer needing to close on a tight timeline, given the current lack of active listings.
- A buyer set on new or near-new construction throughout the neighborhood, given the median year built of 1959.
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 12 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($375K) IS the median in the snapshot above, and the move from 2025 ($442K) IS the -15.3% one-year change.
Windows contain 0 to 10 sales each (6 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2012 through 2026. Deemed reliable but not guaranteed.
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Pinellas County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Pinellas County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.
Highland Pines Market Scorecard
Highland Pines 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: Stellar MLS, distributed by MLS GRID, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Highland Pines on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
Schools
- Pinellas County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Pinellas County Public Schools (verify by address) · Public
- Confirm zoned elementary, middle, and high · By address
- Magnet and choice options may apply · Choice
Zoned schools reflect the assignments reported on recent Highland Pines listings and can change; always confirm with Pinellas County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Highland Pines address.
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 market with no current inventory
The numbers tell a specific story: a median price of $392,500 against a median price per square foot of $260.02 and a median living area of 1,426 square feet. Homes here are modest in scale by design - this is not a subdivision built around larger floor plans - so per-square-foot pricing carries more weight than total square footage when sizing up a listing.
The 70.1% homestead share is worth noting for anyone assessing how the neighborhood functions day to day: most of these properties are claimed as a primary residence rather than held as a rental or second home, which tends to correlate with steadier upkeep over time, though it says nothing about any individual property's current condition. There is no identified community amenity package tied to this subdivision - no clubhouse, pool, or HOA-run facility surfaced in current MLS data - so any lifestyle draw here is about the house and its immediate setting, not shared infrastructure.
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.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in Highland Pines buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 3 factors (5.6). Basis: Recent Direction -15.3% year-over-year; Owner Commitment 67% owner-occupied; Pricing Power 96.8% sale-to-list. Refreshed with each data update.
Why work with Momentum here
With zero active listings, this is not a community you shop by browsing a portal - it is one you track. We watch for the next listing and the next closing here specifically, and with only 8 closings in the recent window, having someone who catches a new one on day one instead of day thirty is the difference between having options and having none. On the sell side, the 72-day median time on market means pricing strategy needs to account for the age and condition spread in the neighborhood rather than a one-size comp.
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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Frequently Asked Questions
What is the median home price in Highland Pines?
How long do homes in Highland Pines take to sell?
How many homes are in Highland Pines?
What share of Highland Pines is owner-occupied?
When were the homes in Highland Pines built?
What schools serve Highland Pines?
Who is the best real estate agent for Highland Pines?
How do I find a top Clearwater real estate agent who knows Highland Pines?
Can Momentum Realty connect me with an agent for Highland Pines?
Should you buy in Highland Pines?
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) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 12, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 33755)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Schools | 2025-26 district assignments + FLDOE school grades; verify with the district |
| Historical depth | Closed-sale records back to 2012 (57 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 Pines Add fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
Explore more neighborhoods near Highland Pines with Momentum Realty’s local guides.