Highland Pines
Homes for Sale in Clearwater, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
As of September 2026, Highland Pines in Clearwater, FL has 2 homes for sale. Over the 12 months ending 2026-09-12, 5 recorded sales closed at a median of $336,000, $276 per square foot, a median 15 days on market, sellers accepting 92% of original asking (-2% versus the prior year). Homes listed or recently sold were built 1954 - 1962; 4 listings state no HOA; none of the 11 geocoded homes sit in a FEMA special flood hazard zone (median elevation 59 ft). At the median price and Pinellas County's FY2025-26 rate of 19.39 mills, annual property tax runs about $6,510 ($5,700 with the full homestead exemption).
Highland Pines right now
🟡 Balanced market. 3.4 months of supply and 50% of the inventory already under contract put buyers and sellers on roughly even footing.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Stellar MLS records, as of September 12, 2026. Confidence: Medium (4 active and pending listings, 5 closed sales in 12 months).
🟡 Off the recent peak. The trailing-12-month median ($336K) is down 2.4% from the prior 12 months ($344K). 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 (5 and 8 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 14, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Highland Pines market snapshot (as of September 12, 2026): the median sale price is about $336K ($276 per sq ft over the trailing 12 months of closed sales), a median 15 days on market for closed sales, and 3.4 months of supply, a balanced market. The trailing-12-month median is down 2% from the prior 12 months, computed from record-level Stellar MLS closed sales (5 closings in the current window).
Flood zones in Highland Pines: of 9 listing addresses checked against the FEMA National Flood Hazard Layer, 100% sit outside the FEMA Special Flood Hazard Area (Zone X). Individual parcels vary - verify any specific address at msc.fema.gov. See flood zones by neighborhood in Clearwater.
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 120 homes in Clearwater, Pinellas County, built between 1950 and 2006 (median 1957.0), with a median living area of about 1,434 square feet. 68% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
The setting & the homes.
Aerial and on-site photos of Highland Pines. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Highland PinesPhotos from Stellar MLS listings in Highland Pines; content deemed reliable but not guaranteed.
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 ($336K) IS the median in the snapshot above, and the move from 2025 ($344K) IS the -2.4% one-year change.
Windows contain 0 to 9 sales each (5 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 2013 through 2026. Deemed reliable but not guaranteed.
Highland Pines Market Scorecard
Highland Pines is currently a seller's market. About 3.4 months of supply, a median asking price of $349,950, and homes go under contract in about 126 days.
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.
Housing distress & ownership in Highland Pines Clearwater, CLEARWATER
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period September 2026 through September 2026. Deemed reliable but not guaranteed.
Homes For Sale Right Now in Highland Pines
Live MLS inventory for Highland Pines. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active · 101 daysTop listingActive · 150 daysPending · 4 daysPending · 10 daysActive and pending Highland Pines listings as of 2026-09-13, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2013 through 2026. Tap any home to ask about it.
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
- Skycrest Elementary (Drew St, verify by address)FLDOE grade A · Public
- Pinellas County Schools middle (verify by address) · Public
- Pinellas County Schools high (verify by address) · Public
Grades are official Florida Department of Education school grades for 2025-26. Assignments are reported as of the 2025-26 year 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.
Shop the zone: Homes zoned for Clearwater High-Pn High School
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 closer look at the Highland Pines market
At a median of $276 per square foot, Highland Pines prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
Inventory runs at 3.4 months of supply, a balanced market and the trailing-12-month median down 2% year over year. Homes that do trade take a median 15 days on market, useful leverage on any listing that has lingered.
The housing stock is 120 homes built between 1950 and 2006, and 68% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
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 4 factors (5.9). Basis: Recent Direction -2.4% year-over-year; Liquidity & Demand 3.4 months of supply; Owner Commitment 68% owner-occupied; Pricing Power 92.4% sale-to-list. Refreshed with each data update.
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 →
Frequently Asked Questions
What is the median home price in Highland Pines?
How long do homes in Highland Pines take to sell?
Is Highland Pines a buyer's or seller's market right now?
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?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 13, 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 (3 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 2013 (61 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 fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
Explore more neighborhoods near Highland Pines with Momentum Realty’s local guides.