Highland Pines
Homes for Sale in Clearwater, FL
All 1,300 homes for sale in Clearwater, FL · median $320,000 · 157 homes for sale in 33755 · Pinellas County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
As of November 2026, Highland Pines in Clearwater, FL has 1 home for sale. Over the 12 months ending 2026-11-13, 3 recorded sales closed at a median of $271,000, $276 per square foot, a median 10 days on market, sellers accepting 102% of original asking. Homes listed or recently sold were built 1954 - 1962; none of the 10 geocoded homes sit in a FEMA special flood hazard zone (median elevation 57 ft). At the median price and Pinellas County's FY2025-26 rate of 19.39 mills, annual property tax runs about $5,250 ($4,440 with the full homestead exemption).
Highland Pines is a small, older pocket of Clearwater where price is driven almost entirely by condition and square footage, not by amenities or new construction. With homes built between 1954 and 1977 and a median living area around 1,386 square feet, the median sits at $325,500, and the spread you'll see in practice comes down to how much updating a given house has absorbed over the decades.
The market here reads balanced: 3.4 months of supply, a median 12.5 days on market, and a heat score of 47. Price is off 5.4% year over year, so sellers should price to current comps rather than last year's, and buyers have a little room to be selective without the frantic pace of a hot market. With only 2 active listings against 69 homes, inventory is thin, so the right house doesn't appear often.
Figures in this note are as of October 26, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Highland Pines right now
🟡 Balanced market. 3.4 months of supply and 33% 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 20, 2026. Confidence: Medium (3 active and pending listings, 6 closed sales in 12 months).
🟡 Off the recent peak. The trailing-12-month median ($326K) is down 5.4% 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 20. Confidence: Medium (6 and 8 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated November 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 20, 2026): the median sale price is about $326K ($263 per sq ft over the trailing 12 months of closed sales), a median 13 days on market for closed sales, and 3.4 months of supply, a balanced market. The trailing-12-month median is down 5% from the prior 12 months, computed from record-level Stellar MLS closed sales (6 closings in the current window).
In ZIP 33755 (Clearwater), 44 homes closed in the last 12 months at a median of $348K ($287/sq ft), with a median 33 days on market. Right now 29 active and 4 pending listings. See the live ZIP 33755 housing market and the Pinellas County market.
County records show 8 qualified sales in Highland Pines across 2024 - 2025 (4 in 2024, 4 in 2025), median $350,000 - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Flood zones in Highland Pines: of 8 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.
Highland Pines is a community of 69 homes in Clearwater, Pinellas County, built between 1954 and 1977 (median 1956), with a median living area of about 1,386 square feet. 61% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
This is a compact, mid-century Clearwater neighborhood of modest-footprint homes where no community amenities show up in current MLS data; the value proposition is the location and the house itself, not shared facilities.
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.
Who Highland Pines is best for.
Best for
- Buying a compact, mid-century home and willing to budget for updates on older systems
- Looking to own in Pinellas County at or near the median rather than chase amenities
- Buyers who can act quickly when one of the few listings that fits comes to market
Probably not for
- Needing new construction or a large floor plan with modern finishes throughout
- Wanting community amenities like pools, trails, or shared facilities
- Expecting a wide selection of homes to tour on any given weekend
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 20 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($326K) IS the median in the snapshot above, and the move from 2025 ($344K) IS the -5.4% one-year change.
Windows contain 0 to 9 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 2013 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.
15% of homes for sale in ZIP 33755 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-11-13).
Highland Pines Market Scorecard
Highland Pines is currently a balanced market. About 3.4 months of supply, a median asking price of $349,950.
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, refreshed twice daily. Market metrics only; these describe homes for sale and recent sales, not residents.
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 and pending Highland Pines listings as of 2026-11-02, 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 contributors.
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 condition-driven mid-century pocket
Nearly every home here predates 1980, with a median build year of 1956, so systems, roofs, and finishes matter more than in a newer subdivision. At a median of roughly $263 per square foot, you're paying for Pinellas County land and location, which means a renovated home and a dated one can land far apart in price even at similar sizes. Budget inspections accordingly and read each listing on its own merits.
A homestead share of about 61% suggests a core of owner-occupants rather than a heavy investor presence, and turnover is modest given the small count of homes. For sellers, the thin active inventory can work in your favor when your home is priced right and shows well; for buyers, patience and readiness to move on the right property both help in a market moving at a balanced, not frantic, pace.
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 (6.2). Basis: Recent Direction -5.4% year-over-year; Liquidity & Demand 3.4 months of supply; Owner Commitment 61% owner-occupied; Pricing Power 96.4% sale-to-list. Refreshed with each data update.
Why work with Momentum here
In a neighborhood this small and this old, the comps that matter are the ones adjusted for condition, and that's where local judgment earns its keep. We'll help you separate a cosmetic refresh from a true systems renovation, price against a down-5.4% trend instead of stale numbers, and move decisively when one of the few listings that fits actually comes up.
Highland Pines in 15 seconds.
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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Recently off market in Highland Pines
Homes in Highland Pines that recently left the market. Each address opens its public-record profile: county-recorded value, property taxes, the last recorded sale, community sales history, and what is for sale nearby now. 4 on record.
- 1519 Chandler Avenue · off market
- 1519 Lynn Avenue · off market
- 1603 Scott Street · off market
- 1609 Scott Street · off market
Last 30 days in Highland Pines: 1 new listing (median asking $314,900), 1 under contract right now. As of November 12, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
| Location | Clearwater, Pinellas County, FL · ZIP 33755 |
|---|---|
| Homes in the community | 69 (FL DOR 2025 assessment roll) |
| Years built | 1954–1977 (median 1956) |
| Typical living area | 1,386 sq ft (median) |
| Home types (current listings and sales) | single-family 100% |
| Sale prices, last 12 months | $271,000 median across 3 closed sales · $276 per sq ft |
| Days on market (closed sales) | 10 median |
| For sale right now | 1 active, 1 pending · median asking $314,900 · 1.5 months of supply |
| Owner-occupied (homestead) share | 61% |
| Zoned public schools | Skycrest Elementary (Drew St, verify by address) (A, FLDOE 2025-26); Pinellas County Schools middle (verify by address); Pinellas County Schools high (verify by address) |
Data as of November 13, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2023 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Highland Pines key facts,” movewithmomentum.com/neighborhoods/highland-pines-clearwater, data as of November 13, 2026.
Every Home for Sale in Highland Pines Right Now (2)
All 2 active and pending Highland Pines listings with a detail page, newest first, refreshed twice a day from the MLS.
- 1610 Scott Street · $314,900 · 3 bd / 1 ba · listed Nov 6, 2026 · listed by The Elite Realty Experience
- 1415 Wood Avenue · $269,900 · 3 bd / 2 ba · pending · listed Aug 15, 2026 · listed by Exp Realty Llc
Recently sold in Highland Pines Clearwater
- 1609 Scott Street · sold $271,000
- 1519 Lynn Avenue · sold $235,000
- 1603 Scott Street · sold $336,000
- 1603 Scott Street · sold $230,000
Closed sales from the MLS; each page shows the sold price, taxes and value history.
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Clearwater guides & data
- Market data
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- Flood zones
- Property taxes (Pinellas County)
- Homestead exemption (Pinellas County)
- Home insurance cost
Florida buyer guides
- Florida home insurance rates by county
- Florida property tax by county
- Florida property tax calculator
- What flood zone X means
- The 4-point inspection, explained
- Florida flood insurance calculator
- Florida housing market map
- Interactive housing market map (county, ZIP and community)
- Save Our Homes tax estimator
- How to stop a foreclosure in Florida
- Florida documentary stamp tax, explained
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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?
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?
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Where is Highland Pines, and what county is it in?
Is Highland Pines a good place to live?
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: November 2, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 20, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 33755)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Schools | 2025-26 district assignments + FLDOE school grades; verify with the district |
| Historical depth | Closed-sale records back to 2013 (62 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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More on Highland Pines
- Home values · What homes in Highland Pines actually sell for