Winston Estates
Homes for Sale in Belleair Beach, FL
All 35 homes for sale in Belleair Beach, FL · median $1,187,000 · 31 homes for sale in 33786 · Pinellas County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Stellar MLS
As of October 2026, Winston Estates in Belleair Beach, FL has 2 homes for sale. Homes listed or recently sold were built 1957–2005; 1 of the 3 geocoded homes sit in a FEMA special flood hazard zone (median elevation 4 ft).
| Location | Belleair Beach, Pinellas County, FL · ZIP 33786 |
|---|---|
| Homes in the community | 167 (FL DOR 2025 assessment roll) |
| Years built | 1939–2024 (median 1974) |
| Typical living area | 2,635 sq ft (median) |
| For sale right now | 2 active, 0 pending · median asking $1,097,000 · 24.0 months of supply |
| Owner-occupied (homestead) share | 54% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2005 through 2025; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Winston Estates key facts,” movewithmomentum.com/neighborhoods/winston-estates, data as of September 20, 2026.
Last 30 days in Winston Estates: 1 new listing (median asking $695,000). As of October 2, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
Winston Estates is a small, established pocket of 167 homes in Belleair Beach, and the price story here is driven by condition and lot far more than by any single spec. With a median year built of 1974 and construction spanning 1939 to 2024, you are looking at a genuinely mixed vintage: original coastal homes, decades of renovation, and a handful of new builds sitting side by side. That spread means two homes with similar square footage can trade very differently depending on how much updating has already been done.
The median living area runs about 2,635 square feet, which is substantial, so buyers are generally paying for real space rather than a starter footprint. With just over half of homes homesteaded, this reads as an owner-occupied community with modest turnover, not an investor churn. For sellers, that stability supports pricing patience; for buyers, it means the right listing may not come often, and when a well-renovated home appears it will command the top of the condition-driven range.
Winston Estates right now
🟢 Buyer-leaning market. 24.0 months of supply and 0% of the inventory already under contract give buyers above-average negotiating leverage.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Stellar MLS records, as of September 20, 2026. Confidence: Low (2 active and pending listings, 1 closed sales in 12 months).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 2, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Winston Estates is a compact Belleair Beach enclave where an older median vintage meets ongoing renovation and occasional new construction, so the housing stock is anything but uniform. The large median footprint and majority homesteaded ownership give it the feel of a settled coastal community rather than a high-turnover market.
Stellar MLS sales records identify 34 homes in Winston Estates that have changed hands since 2006, built between 1956 and 2022 (median 1971), with a median living area of about 1,694 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 6 qualified sales in Winston Estates across 2024–2025 (1 in 2024, 5 in 2025), median $3.60M — 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.
The setting & the homes.
Aerial and on-site photos of Winston Estates. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Photos from Stellar MLS listings in Winston Estates; content deemed reliable but not guaranteed.
Who Winston Estates is best for.
Best for
- Buyers seeking a larger home and comfortable weighing renovated versus original stock
- Owner-occupants who value settled, low-turnover surroundings over new-build sameness
- Buyers with a renovation budget who want to buy an older home and finish it their way
Probably not for
- Buyers who need new construction and predictable, uniform finishes
- Investors chasing high transaction volume and quick flips
- Buyers who want a fixed price range and cannot tolerate condition-driven pricing swings
The market around Winston Estates
Winston Estates is too small for its own price trend, so here is the market around it.
In ZIP 33786, 41 homes are on the market and 15% are under contract — a slower corner of Belleair Beach.
Across Pinellas County, 6,539 homes are active and 1,627 pending (20% under contract).
In ZIP 33786 (Belleair Beach), 47 homes closed in the last 12 months at a median of $850K ($477/sq ft), down 7.8% year over year, with a median 59 days on market. Right now 18 active and 2 pending listings put supply at about 17.7 months — a soft market. See the live ZIP 33786 housing market and the Pinellas County market.
ZIP and county figures describe the wider market, not Winston Estates specifically. Momentum Research analysis of MLS records.
Housing distress & ownership in Winston Estates, Belleair Beach
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 September 2026 through September 2026. Deemed reliable but not guaranteed.
Homes For Sale Right Now in Winston Estates
Live MLS inventory for Winston Estates. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active and pending Winston Estates listings as of 2026-10-01, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2005 through 2025. Tap any home to ask about it.
Every Home for Sale in Winston Estates Right Now (2)
All 2 active and pending Winston Estates listings with a detail page, newest first, refreshed twice a day from the MLS.
- 114 12th Street · $695,000 · 2 bd / 2 ba · listed Sep 10, 2026 · listed by Smith & Associates Real Estate
- 114 13th Street · $1,499,000 · 3 bd / 2.5 ba · listed Aug 7, 2026 · listed by Coldwell Banker Realty
Winston Estates on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
Schools
- Pinellas County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Mildred Helms Elementary-PN · Elementary
- Largo Middle-PN · Middle
- Largo High-PN · High
Zoned schools reflect the assignments reported on recent Winston Estates listings and can change; always confirm with Pinellas County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Winston Estates address.
Shop the zone: Homes zoned for Largo High-Pn High School
The Winston Estates buying strategy.
If we were buying in Winston 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.
Use your leverage. With inventory sitting, there is room to negotiate on anything dated or overpriced and to ask for repairs or a rate buydown.
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 Winston Estates.
Vintage, condition, and the renovation gap
The defining feature of Winston Estates is age spread. A 1939-to-2024 build range around a 1974 median tells you the community grew over generations and continues to be reworked. In practice, that creates a wide gap between homes that have been taken to studs and modernized and those still carrying original systems. Coastal older homes also carry the usual due-diligence items — roof age, elevation, insurance, and any past water intrusion — that matter more here than in a uniform subdivision.
Because square footage is generous at a roughly 2,635-square-foot median, the value question is less about size and more about what has already been invested. Buyers should underwrite renovated and unrenovated homes as two different products, and sellers should be honest about which side of that line their home falls on before pricing it. The single median we can cite reflects a blended market; the actual spread around it is real and condition-led.
The location and the amenities are priced into every listing in Winston Estates. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
A market this varied rewards a broker who prices by condition, not by comps alone. We help sellers position a renovated versus original home correctly, and we help buyers separate a home that is priced for its finishes from one that is priced for the work it still needs. In a low-turnover coastal enclave, timing and inspection discipline matter, and that is where we earn our keep.
Winston Estates 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 Winston 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 Winston Estates sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Winston 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 Winston Estates home worth?
Get a no-obligation home value based on real comparable sales in Winston 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.
See all homes for sale in Belleair Beach →
Recently off market in Winston Estates
Homes in Winston Estates that recently left the market. Each address opens its public-record profile: county-recorded value, property taxes, the last recorded sale, community sales history, and what is for sale nearby now. 1 on record.
- 1203 Bay Drive · off market
8% of homes for sale in ZIP 33786 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-10-01).
Frequently Asked Questions
Is Winston Estates a buyer's or seller's market right now?
How many homes are in Winston Estates?
What share of Winston Estates is owner-occupied?
When were the homes in Winston Estates built?
Who is the best real estate agent for Winston Estates?
How do I find a top Belleair Beach real estate agent who knows Winston Estates?
Can Momentum Realty connect me with an agent for Winston Estates?
Where is Winston Estates, and what county is it in?
Should you buy in Winston Estates?
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: October 1, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (5 streets, ZIP 33786)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2005 (21 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.
Own a home here?
You just read the data. Now see what your home is worth.
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 local comps.
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See how Winston Estates fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
Explore more neighborhoods near Winston Estates with Momentum Realty’s local guides.