Hiland Square Add
Homes for Sale in St Petersburg, FL

Community in St Petersburg · Pinellas County
268 homesBuilt 1943–2019
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Built fromLive Stellar MLS data11 years of closingsFL DOR public recordsUpdated twice daily
Live · Hiland Square Add Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 8,500+ transactions · Top 1% in Florida (RealTrends)
Ownership and context
73%
Owner-occupied · Hiland Square Add
197 of 271 parcels homesteaded (FL DOR 2025)
27%
Non-owner-occupied · Hiland Square Add
incl. 8% trust or LLC-held · 3% out-of-state
33%
Cash buyers · Hiland Square Add
1 of 3 sales, 12 mo ending June 2020
268
Homes in the community
plus 3 vacant residential lots · 271 residential parcels (FL DOR 2025)
Track record · 11 years of records
Est. 1943
Community established
homes built 1943-2019, median 1960 (FL DOR 2025)
1
Failed listings · 2026
peaked at 4 in 2025
Jon Brooks, founder of Momentum Realty
Jon's Current Read

Hiland Square Add is an older St Petersburg pocket, with a median build year of 1960 inside a range that stretches from 1943 up to as recent as 2019. That spread means the housing stock is not uniform — original mid-century construction sits alongside newer infill or heavily updated homes, and condition rather than location is what separates one listing from the next here.

With 268 homes and a homestead share just under three-quarters, this reads as a settled, owner-occupied core rather than a churn-heavy rental or investor pocket. For a buyer, that generally means fewer distressed or turnkey-flip listings hitting at once; for a seller, it means your comparable set can vary widely by age and finish level, so pricing needs to be built off the specific home, not the neighborhood average.

Best for

  • Buyers prioritizing an established St Petersburg location over amenity access
  • Buyers comfortable evaluating condition and updates home-by-home rather than relying on a uniform build era
  • Buyers targeting a modest, efficient footprint rather than maximum square footage

Probably not for

  • Buyers who want a community with a pool, clubhouse, or organized recreation included
  • Buyers seeking a uniformly new or uniformly renovated block with minimal condition variance
  • Buyers who need a larger living area as a baseline, given the median sits near 1,363 sq ft

The market around Hiland Square Add

Hiland Square Add is a small community — 19 recorded sales on file, most recently in 2026 — too few for its own price trend. Here is the market around it.

Across Pinellas County, 6,909 homes are active and 1,852 pending (21% under contract).

Homes here are single family residence.

ZIP and county figures describe the wider market, not Hiland Square Add specifically. Momentum Research analysis of MLS records.

If we were buying in Hiland Square Add today, this is the order of operations we would run for our clients.

1

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.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

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 Hiland Square Add.

Best Buy
Buyers looking for an established, owner-occupied St Petersburg pocket without a built-in amenity package.
Biggest Risk
The wide build-year range means condition varies sharply from one listing to the next.
Sweet Spot
A home built or substantially updated closer to the newer end of the range, sized near the 1,363 sq ft median.
Avoid If
You want a community with organized shared amenities — none are identified here.

A mid-century core with uneven updates

The defining fact about Hiland Square Add is its age range. A median year built of 1960 puts most homes solidly in the mid-century category, but the range running to 2019 tells you there are exceptions — later builds or full teardown-rebuilds mixed into the same blocks. That combination means two homes a few doors apart can differ dramatically in systems, layout, and finish, even if they're similar in size.

At a median living area of 1,363 square feet, this is a community of modest-footprint homes, which tends to suit buyers prioritizing location and lot over square footage. With no shared community amenities identified from current listings, there's no clubhouse, pool, or HOA-run recreation to factor into carrying costs — what you're buying is the house and the neighborhood itself, plain and simple.

The location and the amenities are priced into every listing in Hiland Square Add. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty

Why work with Momentum here

In a neighborhood this age-varied, the difference between a fair offer and an overpay often comes down to knowing which systems and updates in a given home are original versus replaced. We walk that distinction line by line before you commit, and we price listings against the right comparable — not against a neighborhood-wide average that can mask a lot of variation.

Hiland Square Add in 15 seconds.

Best forBuyers looking for an established, owner-occupied St Petersburg pocket without a built-in amenity package.
Biggest advantageThe high homestead share signals a settled ownership base rather than heavy investor turnover.
Biggest riskThe wide build-year range means condition varies sharply from one listing to the next.
Sweet spotA home built or substantially updated closer to the newer end of the range, sized near the 1,363 sq ft median.
Avoid ifYou want a community with organized shared amenities — none are identified here.

HOA, CDD & Fees

In short
  • Mandatory HOA — confirm current dues
  • 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.

The takeaway

Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Hiland Square Add sales matched to your home.

What is your Hiland Square Add home worth?

Get a no-obligation home value based on real comparable sales in Hiland Square Add, 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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Real comps, not an automated estimate.

Frequently Asked Questions

How many homes are in Hiland Square Add?
The Florida DOR 2025 assessment roll shows 268 homes plus 3 vacant residential lots in Hiland Square Add (public records).
What share of Hiland Square Add is owner-occupied?
73% of Hiland Square Add parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in Hiland Square Add built?
Homes in Hiland Square Add were built between 1943 and 2019, with a median year built of 1960.0 (FL DOR 2025 roll).
Do cash buyers compete in Hiland Square Add?
Cash buyers took 33% of Hiland Square Add sales in the 12 months ending June 2020 (1 of 3 closings, Stellar MLS).
Who is the best real estate agent for Hiland Square Add?
The best agent for Hiland Square Add is one who actively works St Petersburg and knows the community's pricing, fees, and current inventory. Tell us what you're looking for in the form on this page and Momentum Realty will match you with a local specialist for Hiland Square Add.
How do I find a top St Petersburg real estate agent who knows Hiland Square Add?
Share a few details in the form on this page. Momentum Realty has 280+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows Hiland Square Add and the wider St Petersburg area.
Can Momentum Realty connect me with an agent for Hiland Square Add?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Hiland Square Add purchase or sale - no call center and no pressure.
Buyers prioritizing an established St Petersburg location over amenity accessExcellent fit
Buyers comfortable evaluating condition and updates home-by-home rather than relying on a uniform build eraExcellent fit
Buyers targeting a modest, efficient footprint rather than maximum square footageExcellent fit
Buyers who want a community with a pool, clubhouse, or organized recreation includedProbably not
Buyers seeking a uniformly new or uniformly renovated block with minimal condition varianceProbably not
Buyers who need a larger living area as a baseline, given the median sits near 1,363 sq ftProbably not

Data sources & freshness

Housing stock & ownershipFlorida DOR 2025 assessment roll (street-list match (2 streets, ZIP 33709))
Under-contract sharesStellar MLS records, as of 2026-07-12
Historical depthClosed-sale records back to 2015 (6 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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The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live your area comps.

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