Winston Park
Homes for Sale in Tampa, FL

Winston Park market snapshot (as of September 12, 2026): the median sale price is about $288K ($228 per sq ft over the trailing 12 months of closed sales), and a median 6 days on market for closed sales. The trailing-12-month median is down 20% from the prior 12 months, computed from record-level Stellar MLS closed sales (5 closings in the current window).

In ZIP 33619 (Tampa), 516 homes closed in the last 12 months at a median of $345K ($249/sq ft), down 7.0% year over year, with a median 27 days on market. Right now 105 active and 21 pending listings put supply at about 5.4 months — a balanced market. See the live ZIP 33619 housing market and the Hillsborough County market.

Stellar MLS sales records identify 67 homes in Winston Park that have changed hands since 2004, built between 1961 and 1985 (median 1976), with a median living area of about 1,262 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.

This is a compact, mostly owner-occupied neighborhood — homestead share is about 73% — of modest-sized homes, where the winners and losers on price come down to how much updating a house has actually had.

With a median year built of 1976 and a range stretching back to 1958, mechanicals and systems matter. Roof age, HVAC, electrical, and plumbing on the older homes can swing your true cost well past the sticker, so the median of $283,799.50 is best read as a midpoint, not a menu. Two homes on the same street can price very differently based on renovation history alone.

The homestead share near 73% points to a neighborhood that turns over slowly, which is part of why inventory that is priced right moves in around 5 days. Read that speed with caution: fast sales plus a 22.2% year-over-year decline means the market is rewarding realistic pricing and punishing everything else. Base your number on recent closings and condition, not on what the house down the block asked for last year.

This is a market where the median hides more than it reveals, and only a handful of homes close in a given window. We read each listing on its own terms — systems, updates, square footage against that roughly 1,468 typical footprint — and price against actual closings rather than stale asks. That discipline is what protects you on both sides of the table in a neighborhood moving this fast but down this much year over year.

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.