Highland Pines
Homes for Sale in Clearwater, FL
All 1,260 homes for sale in Clearwater, FL · median $314,950 · 143 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 11 closed sales in Highland Pines 4Th Add in Clearwater, FL since 2012, the most recent in March 2026. 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 1,102 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).
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 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 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 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.
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, 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.
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.
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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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 19, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| 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.
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 October 2026.
- 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 - July 2026Development
St. Pete advances housing plan for nine vacant city lots
The St. Petersburg City Council unanimously approved a first reading of an ordinance to place a measure on the November 3 ballot that would remove nine vacant city lots in Methodist Town from the city's Charter Park and Waterfront Map. The change would allow up to 41 units of affordable or workforce housing, with four lots planned for single family homes and five larger parcels for multifamily housing. The lots have held park designations since 1984 but have remained vacant.
What it may mean for the marketAdvances a plan to convert nine vacant city lots into new single family and multifamily housing, adding to local housing inventory. Placing the parcels on the ballot could open long dormant land for residential construction. The project is about 13 miles south of Highland Pines 4th Add, elsewhere in Pinellas County.
Source: St Pete Catalyst - July 2026Development
Blake-Related team selected to redevelop 86-acre Historic Gas Plant District
St. Petersburg selected a bid led by Blake Investment Partners, with the Related Group as co-developer, to redevelop the 86-acre Historic Gas Plant District at the Tropicana Field site. The roughly 8.1 billion dollar mixed use plan calls for more than 3,600 income-restricted residential units, a 13-acre central park, and office, retail, hotel and civic space over an estimated 20-year buildout. The developers plan to purchase about 58 acres while the city retains roughly one third.
What it may mean for the marketAdds a large mixed use district with thousands of new residential units, a central park, and office, retail, hotel and civic space to the downtown St. Petersburg market. Redevelopment of the Tropicana Field site reshapes the surrounding property landscape and expands housing supply. The project is about 13 miles south of Highland Pines 4th Add, elsewhere in Pinellas County.
Source: Florida YIMBY
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.
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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).
Email me new listings in Highland PinesHomes for Sale
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 PinesHomes for Sale
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Highland PinesHomes for Sale will answer, and the answer is published on this page for the next buyer.
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.
| 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.
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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 (12 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)
- Long Street (4 homes on record)
- Scott Street (4 homes on record)
Nearby Communities
Explore more neighborhoods near Highland Pines with Momentum Realty’s local guides.
Highland Pines 4Th Add Market Scorecard
Highland Pines 4Th Add 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: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.