Five Towns of St. Petersburg vs Windward Pointe
Two Pinellas communities, compared on the numbers that decide it — price, pace, and supply — from live MLS data as of 2026-09-19.
| Metric | Five Towns of St. Petersburg | Windward Pointe |
|---|---|---|
| Median sale price | $100K | $140K |
| Price per sq ft | $80 | $141 |
| Avg days on market | 199 days | 164 days |
| Months of supply | 5.4 mo | 2.4 mo |
| Market | Buyer-Leaning Market | Balanced Market (limited data) |
| 1-year price change | False | False |
| Recent closings | 47 | 10 |
The verdict
Windward Pointe carries the higher median price — about 40% above Five Towns of St. Petersburg. Homes in Windward Pointe sell faster (164 days on market vs 199). Windward Pointe is the tighter market on inventory (2.4 months of supply).
Where each one is
| Five Towns of St. Petersburg | Windward Pointe | |
|---|---|---|
| County | Pinellas County, FL | Pinellas County, FL |
| City / area | St Petersburg | St Petersburg |
| ZIP | 33709 | 33716, 33785 |
Distances are straight-line; driving distance is usually 15 to 30 percent more. Flood-zone shares come from FEMA flood maps matched to sampled parcels; always check the exact address before you close.
What is for sale today
| Five Towns of St. Petersburg | Windward Pointe | |
|---|---|---|
| Homes for sale now | 21 | 2 |
| Under contract | 6 | 2 |
| Asking prices today | $70K to $350K | $120K to $160K |
| Property types listed | Condominium | Condominium |
Live MLS counts, refreshed with every listing pull. Browse them: Five Towns of St. Petersburg homes for sale · Windward Pointe homes for sale.
Price history, year by year
| Year | Five Towns of St. Petersburg median | Windward Pointe median |
|---|---|---|
| 2015 | $44K (30 sales) | $44K (16 sales) |
| 2016 | $54K (55 sales) | $64K (15 sales) |
| 2017 | $59K (40 sales) | $62K (13 sales) |
| 2019 | $95K (10 sales) | $88K (6 sales) |
| 2021 | $102K (24 sales) | $133K (7 sales) |
| 2022 | $158K (78 sales) | $170K (27 sales) |
| 2023 | $170K (33 sales) | $168K (6 sales) |
| 2024 | $145K (43 sales) | $165K (15 sales) |
| 2025 | $120K (31 sales) | $137K (20 sales) |
| 2026 | $97K (40 sales) | $145K (6 sales) |
Since 2015, Five Towns of St. Petersburg's median sale price is +121% and Windward Pointe's is +228% — Windward Pointe has appreciated faster over that stretch.
How each one trades
| Five Towns of St. Petersburg | Windward Pointe | |
|---|---|---|
| Sale-to-original-list | 81.5% | 93.0% |
| New-construction share of sales | 0% | 0% |
| Typical sold home | 1,125 sq ft | 991 sq ft |
| Momentum market-heat score | 28 (cold) | 30 (cold) |
Last 12 months of recorded closings; sale-to-original-list is the share of the first asking price sellers actually got.
Schools the listings are zoned for
| Five Towns of St. Petersburg | Windward Pointe | |
|---|---|---|
| Elementary | Rawlings Elementary-Pn | Sawgrass Lake Elementary-Pn |
| Middle | Pinellas Park Middle-Pn | Fitzgerald Middle-Pn |
| High school | Dixie Hollins High-Pn | Pinellas Park High-Pn |
The school most often recorded on each community's MLS listings. Always confirm a specific address with the district.
Which one fits
On budget alone, Five Towns of St. Petersburg is the lower entry point (median $100K vs $140K). Sellers get a faster sale in Windward Pointe (164 days on market on average); buyers get more negotiating room where homes sit longer.
Neither number set decides it: drive both on a weekday evening, check the HOA documents and the flood zone for the exact street, and price the insurance before you write an offer. A Momentum agent who works both communities can pull the comparable sales for any two specific homes.
Questions people ask
Is Windward Pointe more expensive than Five Towns of St. Petersburg?
Yes, on recent sales: the median sale price in Windward Pointe is $140,000 versus $100,000 in Five Towns of St. Petersburg, about 40% higher.
Which has appreciated more, Five Towns of St. Petersburg or Windward Pointe?
From 2015 to 2026 the median sale price rose 121% in Five Towns of St. Petersburg and 228% in Windward Pointe (recorded MLS closings by calendar year).
Where do sellers get closer to asking price?
Windward Pointe — sellers there received 93.0% of the original list price over the last 12 months versus 81.5% in Five Towns of St. Petersburg.
What high schools serve Five Towns of St. Petersburg and Windward Pointe?
Listings in Five Towns of St. Petersburg most often report Dixie Hollins High-Pn; listings in Windward Pointe report Pinellas Park High-Pn. Zoning is set by the district and can change - verify by address.
Go deeper on each: Five Towns of St. Petersburg homes, photos & schools · Windward Pointe homes, photos & schools
Figures are aggregates from realMLS / DBAAR, updated regularly. Thinking about either? Talk to Momentum Realty.