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.
Photo via Stellar MLS
As of November 2026, the MLS records 11 closed sales in Highland Pines 4Th Add in Clearwater, FL since 2012, the most recent in March 2026. Across Clearwater as a whole, 2,252 homes closed in the last 12 months at a median of $320,000, 47 median days on market, with 1,130 homes for sale today. At that median and Pinellas County's FY2025-26 rate of 19.39 mills, annual property tax runs about $6,200 ($5,390 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.
Figures in this note are as of July 14, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Nearby homes for sale
No active listings inside Highland Pines 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 4Th 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.
Stellar MLS sales records identify 292 homes in Highland Pines that have changed hands since 2004, built between 1950 and 2006 (median 1959), with a median living area of about 1,350 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.
County records show 7 qualified sales in Highland Pines across 2024–2025 (3 in 2024, 4 in 2025), median $322,500 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
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, 163 homes are on the market and 23% are under contract — a steady corner of Clearwater.
Across Pinellas County, 6,539 homes are active and 1,627 pending (20% under contract).
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.
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.
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 →
| Location | Clearwater, Pinellas County, FL · ZIP 33755 |
|---|---|
| Homes in the community | 117 (FL DOR 2025 assessment roll) |
| Years built | 1950–2001 (median 1958) |
| Typical living area | 1,515 sq ft (median) |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 65% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2012 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-4th-add, data as of September 20, 2026.
Housing distress & ownership in Highland Pines 4Th Add, 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 November 2026 through November 2026. Deemed reliable but not guaranteed.
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Clearwater guides & data
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Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- N Saturn Avenue (21 homes on record)
- Scott Street (13 homes on record)
- Murray Avenue (9 homes on record)
- Murray Avenue (9 homes on record)
- Scott Street (9 homes on record)
- Sherwood Street (8 homes on record)
- Sherwood Street (8 homes on record)
- Long Street (7 homes on record)
- Long Street (5 homes on record)
- Sherwood Street (5 homes on record)
- Scott Street (4 homes on record)
- Long Street (4 homes on record)
Email me new listings in Highland Pines
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Highland Pines
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Highland Pines will answer, and the answer is published on this page for the next buyer.
Recent Developments in Highland Pines 4th Add
Development, infrastructure, retail, and school activity affecting Highland Pines 4th Add, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated November 2026.
- October 2026Market
North St. Petersburg FedEx warehouse sells for $58.2M, $36M below 2021 price
A 236,976 square foot FedEx Ground distribution center at 1950 102nd Avenue N. on about 63 acres near I-275 sold for $58.2 million, versus $94.5 million in 2021. FedEx has operated there since 2017 and the deed shows no change to its lease. The article ties the sale to higher borrowing costs facing the prior owner.
What it may mean for the marketThe sale points to repricing in Pinellas industrial property while the last-mile logistics hub keeps operating near I-275. The project is about 7 miles south of Highland Pines 4th Add, elsewhere in Pinellas County.
Source: St. Pete Catalyst - October 2026Development
Humane Society of Tampa Bay to open Clearwater clinic on State Road 590
The nonprofit's clinic at 2907 State Road 590, Suite 5, near its Clearwater shelter opens Nov. 2, with a grand opening Nov. 12. It offers vaccinations, wellness exams, microchipping, lab work and X-rays by appointment, with spay and neuter services planned later.
What it may mean for the marketA new low-cost veterinary option near the SR 590 corridor adds a neighborhood service amenity in central Clearwater. The project is about 5 miles west of Highland Pines 4th Add, elsewhere in Pinellas County.
Source: St. Pete Catalyst - October 2026Development
ClearView apartments complete at $1 billion Echelon City Center in St. Petersburg
The 363-unit ClearView community, with ground-floor retail, is complete within the Echelon City Center development by Third Lake Partners and Echelon. A 3rd & 3rd residential high-rise with ground-floor retail is expected to open in the first quarter of 2027.
What it may mean for the marketNew downtown apartments and walkable retail add rental inventory and amenities in central St. Petersburg. The project is about 13 miles south of Highland Pines 4th Add, elsewhere in Pinellas County.
Source: Tampa Bay Business and Wealth - August 2026Development
AECOM Hunt selected as construction manager for proposed $2.3 billion Rays ballpark in Tampa
AECOM Hunt joined the design team led by Populous for the proposed ballpark on a site that includes Hillsborough College property. The stadium would have at least 28,000 fixed seats, with a construction start targeted for September 2026 and completion by late 2028. Tampa's public contribution is up to $80 million and financing is not finalized.
What it may mean for the marketA large ballpark and surrounding mixed-use district would add construction jobs, event traffic and retail demand on the Dale Mabry corridor. The site is about 10 miles east of Highland Pines 4th Add.
Source: Tampa Bay Business and Wealth - August 2026Infrastructure
Four firms vie to build Tampa International Airport's $150 million control tower
TPA narrowed the field to four builders for a new blast-resistant air traffic control tower on about 2 acres northwest of the main terminal. The budget is about $150 million, with board selection expected Oct. 1 and substantial completion targeted for March 2029.
What it may mean for the marketAirport capital spending supports construction employment and long-term air service capacity for the region. The site is about 8 miles east of Highland Pines 4th Add.
Source: Tampa Bay Business and Wealth - July 2026Infrastructure
St. Pete approves temporary downtown dock for Tampa Bay ferry
The St. Petersburg City Council approved a temporary ferry dock on Bayshore Boulevard near the Vinoy in downtown St. Petersburg under a three-year contract costing about 324,200 dollars. Hubbard's Marina will operate cross bay service between downtown St. Petersburg and the Tampa Convention Center, with two vessels running year round. Service is expected to begin in October or November.
What it may mean for the marketEstablishes a temporary downtown dock and cross bay ferry connection, adding a new transit option and waterfront infrastructure serving the downtown St. Petersburg market. The project is about 13 miles south of Highland Pines 4th Add, elsewhere in Pinellas County.
Source: FOX 13 Tampa Bay
Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in Northeast Florida.
Frequently Asked Questions
How many homes are in Highland Pines?
What share of Highland Pines is owner-occupied?
When were the homes in Highland Pines built?
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Where is Highland Pines, and what county is it in?
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 12, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (3 streets, ZIP 33755)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| 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.
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