Highland Pines Estates
Homes for Sale in Plant City, FL
All 308 homes for sale in Plant City, FL · median $391,700 · 123 homes for sale in 33565 · Hillsborough County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of November 2026, the MLS records 13 closed sales in Highland Pines Estates in Plant City, FL since 2015, the most recent in March 2022. Across Plant City as a whole, 844 homes closed in the last 12 months at a median of $345,000, 39 median days on market, with 295 homes for sale today. At that median and Hillsborough County's FY2025-26 rate of 15.73 mills, annual property tax runs about $5,430 ($4,800 with the full homestead exemption).
Price here is driven by condition and vintage, not by a uniform product. With a build range stretching from 1900 to 2023 and a median year built of 1987, Highland Pines Estates is not a subdivision with a single floor plan repeated down the block — it is a collection of homes of very different ages sitting near one another. That spread means the number you pay depends heavily on which era and what level of updating you are buying into, and comparables have to be chosen carefully.
The median living area sits near 1,794 square feet, so the core of this market is mid-sized homes rather than sprawling new construction. For a buyer, that variety is leverage: an updated home and a project home can trade at very different prices even on the same street, and knowing which one you are looking at matters more than the headline median. For a seller, presentation and condition do a lot of the pricing work here.
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 Estates 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 Estates is a 273-home community in Plant City, Hillsborough County, defined less by a single style than by a long build history — everything from turn-of-the-century houses to homes finished in 2023.
Stellar MLS sales records identify 19 homes in Highland Pines Estates that have changed hands since 2011, built between 1954 and 2012 (median 2000), with a median living area of about 1,620 sq ft and a typical 3-bedroom, 2-bath layout. 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 14 qualified sales in Highland Pines Estates across 2024–2025 (5 in 2024, 9 in 2025), median $456,800 — 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 Estates is best for.
Best for
- Buyers targeting a mid-sized home who will inspect closely and price on condition
- Owner-occupant buyers who value an established, high-homestead area
- Renovation-minded buyers willing to take on an older home for the right basis
Probably not for
- Buyers who want only new construction with a single, predictable floor plan
- Investors chasing quick-turn flips in a low-turnover, owner-held market
- Buyers unwilling to budget for the systems and upkeep an older home may require
The market around Highland Pines Estates
Highland Pines Estates is too small for its own price trend, so here is the market around it.
In ZIP 33565, 169 homes are on the market and 21% are under contract — a steady corner of Plant City.
Across Hillsborough County, 6,324 homes are active and 1,810 pending (22% under contract).
In ZIP 33565 (Plant City), 72 homes closed in the last 12 months at a median of $390K ($176/sq ft), with a median 43 days on market. See the live ZIP 33565 housing market and the Hillsborough County market.
ZIP and county figures describe the wider market, not Highland Pines Estates specifically. Momentum Research analysis of MLS records.
The Highland Pines Estates buying strategy.
If we were buying in Highland Pines Estates 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 Estates.
A market of eras, not floor plans
The defining feature here is age spread. A build range from 1900 through 2023 around a 1987 median tells you this is an established area that has absorbed new infill over time. Expect to evaluate each home on its own terms — roof, systems, and updates will vary widely, and two houses of similar size can be very different purchases.
Owner-occupancy runs high, with a homestead share of about 68 percent. That points to a community held largely by people who live in their homes rather than one dominated by turnover or short-term holds, which tends to support steadier upkeep and a less churn-driven resale environment.
The location and the amenities are priced into every listing in Highland Pines Estates. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a market this varied by age and condition, the median is a starting point, not an answer. We build comparables that match the actual home — vintage, systems, and level of updating — so you are not pricing a 1987 median against a fully renovated house or a project. That discipline protects buyers from overpaying and helps sellers position condition honestly.
Highland Pines Estates in 15 seconds.
Tools for a Highland Pines Estates 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 Estates 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 Estates, 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 Estates home worth?
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| Location | Plant City, Hillsborough County, FL · ZIP 33565, 33592 |
|---|---|
| Homes in the community | 273 (FL DOR 2025 assessment roll) |
| Years built | 1900–2023 (median 1987) |
| Typical living area | 1,794 sq ft (median) |
| Owner-occupied (homestead) share | 68% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2015 through 2022; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Highland Pines Estates key facts,” movewithmomentum.com/neighborhoods/highland-pines-estates, data as of September 20, 2026.
Housing distress & ownership in Highland Pines Estates, Plant City
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.
More Plant City home searches
- All homes for sale in Plant City, FL
- Homes for sale in Hillsborough County, FL
- Plant City home values: what is my house worth?
- ZIP 33565 housing scorecard
Plant City guides & data
- Market data
- Cost of living
- Best neighborhoods
- Property taxes (Hillsborough County)
- Homestead exemption (Hillsborough County)
- Home insurance cost
- New construction
- New construction (Hillsborough County)
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
- Cheapest places to live in Florida
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Frequently Asked Questions
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An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Housing stock & ownership | Florida DOR assessment roll (street-list match (4 streets, ZIP 33565/33592)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2015 (13 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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