About the Countryside Key Community

Countryside Key is a gated townhome community in Oldsmar, Florida, built between 1996 and 1997. The neighborhood sits on Countryside Key Blvd off Curlew Rd and Tampa Rd (FL-586 / FL-580), along the Pinellas–Hillsborough county line, minutes from both Palm Harbor and Westchase.

The community is relatively compact by Tampa Bay standards — several dozen two-story buildings arranged around a private street loop, with a central pool, tennis courts and a shared pond. Most units back onto protected conservation land, which is what keeps the quiet, wooded feel that long-time residents appreciate.

What makes it different

• Conservation backdrop. The entire east side of the community abuts the Canal Nature Preserve, so units facing that direction have permanent wooded views — no risk of development behind the property.
• Maintenance-free living. The HOA handles exterior upkeep, landscaping, roofs and common-area maintenance, which is why the community has stayed well-kept since the late 1990s.
• Walkable to trails and sports. Oldsmar Sports Complex and the Pinellas Trail corridor are literally across the street — unusual for a gated community in this price range.
• Between two markets. Residents get Pinellas County amenities and Hillsborough County commuting options; Tampa, St. Petersburg and Clearwater are all roughly 25–35 minutes away.

Typical residents

The community attracts a mix of families with young children (drawn by the safe gated layout and nearby schools), retirees downsizing from larger Tampa Bay homes, and professionals commuting into downtown Tampa or the airport.

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