Highland Park
Homes for Sale in San Mateo, FL
True comps, carrying-cost math, and listings before the portals.
Highland Park is a small pocket in San Mateo, and small means what it always means: with only 14 homes here, a single listing coming or going swings the whole picture. There is no median price in this snapshot, so treat pricing as condition-driven rather than sticker-driven. What sets value here is the individual house — its updates, its footprint, its lot — not a tidy neighborhood band you can price off comps in bulk.
The housing stock runs from 1928 to 1991, with the middle of the pack built around 1966, so you are largely buying older construction. That rewards buyers who can read a home's bones and budget for systems. For sellers, condition is the lever: a genuinely updated house stands out in a market this thin, and a dated one will be judged on the work it needs. Just over half the homes carry a homestead exemption, which points to a core of owner-occupants rather than a churn of rentals.
Figures in this note are as of July 12, 2026. The live market numbers elsewhere on this page update nightly and are newer.
The 60-Second Overview
Highland Park market snapshot (as of October 23, 2026): the median sale price is about $199K ($202 per sq ft over the trailing 12 months of closed sales), and a median 17 days on market for closed sales.
Highland Park is a community of 14 homes in San Mateo, Putnam County, built between 1928 and 1991 (median 1966.0), with a median living area of about 1,220 square feet. 55% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Highland Park is a compact, older enclave in San Mateo where the 14-home count and the 1928–1991 build range matter more than any headline figure. Expect variety house to house rather than a uniform product.
Who Highland Park is best for.
Best for
- Buyers who can budget for updates on a 1928–1991-era home and want a modest footprint
- Long-term owner-occupants who value a small, settled enclave over a big-inventory subdivision
- Renovation-minded buyers looking to shape an older home to their own plan
Probably not for
- Buyers who need a large, modern floor plan well above the roughly 1,220-square-foot median
- Shoppers who want many comparable listings to weigh side by side
- Anyone unwilling to inspect and invest in older systems
Sold History: Closed Sales in Highland Park by Year
Closed sales in Highland Park by trailing-12-month window ending October 23 of each year, from realMLS (Northeast Florida MLS) closing records. 4 homes closed in the current window at a median of $199,000. Aggregates only; individual closed sales are not shown.
| Window | Closings | Median sold | $ / sq ft | Median DOM | Typical size |
|---|---|---|---|---|---|
| 2026 | 4 | $199,000 | $202 | 17 days | 1,018 sq ft |
Source: realMLS closed listings, aggregated by Momentum Research. Deemed reliable but not guaranteed.
Highland Park by the numbers
From county property records and closed MLS sales for the Highland Park subdivision: 10 homes on record; built 1930–1990; typical size about 1,037 heated sq ft; 3 bedrooms is the median. Housing mix: single-family 100%.
| Year | Recorded sales | Median price |
|---|---|---|
| 2007 | 1 | $98,900 |
| 2014 | 1 | $21,750 |
| 2017 | 1 | $162,000 |
| 2019 | 1 | $125,000 |
| 2022 | 2 | $224,670 |
| 2025 | 2 | $102,500 |
Newest recorded sale: $135,000 on 2025-10-31.
Recorded data as of 2026-09-12; counts cover addresses tagged to this subdivision in the public record, not every parcel. Not an appraisal.
The Highland Park buying strategy.
If we were buying in Highland Park 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 Park.
A small, older inventory
The living space here is modest by current standards — the median sits at roughly 1,220 square feet — so this is a market of right-sized homes, not sprawling floor plans. With a median build year around 1966 and the oldest homes reaching back to 1928, you are looking at construction that predates most modern layouts. Renovation potential is real, but so is the diligence required: roofs, electrical, plumbing, and windows all deserve a hard look.
A homestead share just over half tells you this is more a place people settle into than a landlord's inventory. Combined with the tiny home count, that means listings are scarce and each one is its own negotiation. Don't wait for a large set of comparable options — in a 14-home community, the right house is the event, not the norm.
The location and the amenities are priced into every listing in Highland Park. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a 14-home community, data alone won't get you there — you need someone tracking every movement and who knows how an older San Mateo home is likely to inspect before you write an offer. We price on condition, not on a blunt neighborhood average, and we tell you when a house needs more work than its asking price admits.
Highland Park in 15 seconds.
Tools for a Highland Park 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 Park sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Highland Park, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
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Frequently Asked Questions
What is the median home price in Highland Park?
How long do homes in Highland Park take to sell?
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What share of Highland Park is owner-occupied?
When were the homes in Highland Park built?
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Should you buy in Highland Park?
An honest fit check. We will tell you when it is not your community.
Nearby Communities
Explore more neighborhoods near Highland Park with Momentum Realty’s local guides.
Data sources & freshness
| Community market stats | realMLS closed sales, 12-month windows ending October 23, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (1 streets, ZIP 32187)) |
| Under-contract shares | realMLS records, as of 2026-10-20 |
| Historical depth | Closed-sale records back to 2002 (18 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 realMLS 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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