Hollingsworth Estates
Homes for Sale in Clearwater, FL
True comps, carrying-cost math, and listings before the portals.
Hollingsworth Estates is an older Clearwater pocket where the housing stock does most of the pricing work. With a median build year of 1956 and homes running as far back as 1900 alongside newer construction through 2024, condition and updates matter more here than square footage — and the median footprint of roughly 1,636 square feet is modest, so what a home has been through since the mid-century sets the number.
Expect a wide spread rather than a tidy price band. A gut-renovated home and an original one on the same block can sell for very different figures, which means comps have to be read carefully. For sellers, that rewards honest condition disclosure and staging; for buyers, it means the asking price tells you less than the walk-through does.
Who Hollingsworth Estates is best for.
Best for
- Buyers comfortable renovating an older home and budgeting for systems work
- Owner-occupants seeking an established Clearwater location and planning to hold
- Buyers who want a modest, roughly 1,600-square-foot footprint rather than a large new build
Probably not for
- Buyers set on new or near-new construction with modern systems
- Investors looking for high inventory turnover and quick flips
- Buyers who need a narrow, predictable price range to plan against
The market around Hollingsworth Estates
Hollingsworth Estates is a small community — 5 recorded sales on file, most recently in 2023 — 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 Hollingsworth Estates specifically. Momentum Research analysis of MLS records.
The Hollingsworth Estates buying strategy.
If we were buying in Hollingsworth 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 Hollingsworth Estates.
An older stock that trades on condition
The 1900-to-2024 build range is unusually broad for a single community, but the median year built of 1956 tells the real story: this is predominantly a mid-century neighborhood with occasional infill and rebuilds. Buyers should budget for the realities of older Florida construction — roof, systems, and windows — and read each listing on its own merits rather than by street or subdivision average.
A homestead share of about 65% points to a base of long-hold owners rather than a churn of investor flips. That tends to mean fewer distressed sales and a slower, steadier trickle of inventory, so when a well-updated home does list, it can draw disproportionate attention relative to the tired ones sitting beside it.
The location and the amenities are priced into every listing in Hollingsworth Estates. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a neighborhood this condition-driven, a broker who has actually walked the older stock is worth more than any pricing model. We help buyers separate a cosmetic refresh from a real systems overhaul, and we help sellers position an updated home so it isn't priced against its unrenovated neighbors. That local read on age, updates, and comps is exactly where Hollingsworth Estates rewards attention.
Hollingsworth Estates in 15 seconds.
HOA, CDD & Fees
- 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.
Tools for a Hollingsworth 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 Hollingsworth Estates sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Hollingsworth 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 Hollingsworth Estates home worth?
Get a no-obligation home value based on real comparable sales in Hollingsworth Estates, 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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Frequently Asked Questions
How many homes are in Hollingsworth Estates?
What share of Hollingsworth Estates is owner-occupied?
When were the homes in Hollingsworth Estates built?
Do cash buyers compete in Hollingsworth Estates?
Who is the best real estate agent for Hollingsworth Estates?
How do I find a top Clearwater real estate agent who knows Hollingsworth Estates?
Can Momentum Realty connect me with an agent for Hollingsworth Estates?
Should you buy in Hollingsworth Estates?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (5 streets, ZIP 33756/33764)) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| Historical depth | Closed-sale records back to 2009 (14 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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