Countryside Key Homes with Sidewalks Community Features

Countryside Key Homes with Sidewalks Community Features

Welcome to Countryside Key, a picturesque subdivision nestled in the heart of Oldsmar, Florida, in the vibrant Pinellas County. This charming community offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, retirees, and everyone in between.

Countryside Key features beautifully designed homes that reflect modern aesthetics while providing comfortable living spaces. Each residence is thoughtfully situated along tree-lined streets, complete with inviting sidewalks that encourage leisurely strolls and foster a sense of community. The sidewalks are perfect for morning jogs, evening walks, or simply enjoying the scenic neighborhood views.

Residents of Countryside Key benefit from a variety of community features designed to enhance their quality of life. The subdivision boasts meticulously maintained common areas, lush green parks, and recreational facilities, ensuring that there’s always something to do. Whether it’s a weekend picnic with family or a friendly gathering with neighbors, the community atmosphere is warm and welcoming.

Oldsmar itself is a hidden gem, offering a blend of outdoor adventures and urban amenities. With nearby parks, shopping centers, and dining options, residents can enjoy the best of both worlds. The proximity to the stunning Gulf Coast beaches adds an extra layer of appeal, perfect for weekend getaways or spontaneous outings.

If you’re looking for a community that combines charm, convenience, and a strong sense of belonging, Countryside Key is the perfect place to call home. Come and discover the lifestyle that awaits you in this delightful Oldsmar neighborhood!

Newest Countryside Key Homes with Sidewalks Community Features

279 Countryside Key Boulevard, Oldsmar
$275,000
2 Beds ⋅ 2 Baths ⋅ TB8542613 MLS ⋅ N/A BLDG.
Virtually Staged. Welcome home to this beautiful END UNIT & FULLY UPDATED 2BR/1.5BA townhome in the gated Countryside Key community, offering the rare benefit of an extra-large side yard for addl. outdoor space & privacy. Even better, assoc. fees INCLUDE water, trash, cable & internet! With extensive improvements, an enclosed patio, reserved parking directly in front, & an outstanding Pinellas County location (NON-FLOOD ZONE), this home is truly move-in ready. Step inside to an inviting open first floor designed for comfortable everyday living & entertaining. The kitchen features quartz countertops, custom cabinetry installed in '22, including larger cabinets providing excellent storage. The owners thoughtfully removed the upper cabinetry around the sink & counter area, creating a more open feel and better connection between the kitchen & adjoining living space. Updated appliances, lighting & ceiling fans complement the space, while no popcorn ceilings on either the first or second floor give the home a clean, updated look. Fresh interior paint was completed in August '26. Just beyond the main living area, the enclosed patio creates additional flexible space to relax, entertain, work from home, or just enjoy throughout the year. As an end unit, this home also possesses an extra-large side yard, providing additional outdoor space & separation rarely found with townhome living. Upstairs, the spacious primary suite features large dual closets, built-in bookshelves (providing both character & functional storage), while the generous windows bring an abundance of natural light into the space. Relax in the large private upgraded bathroom to complete the suite! The home has also benefited from an impressive list of improvements. HVAC, water heater & appliances were replaced in '22, along with new attic insulation in '22, washer & dryer in '24, & new light fixtures & ceiling fans. A new impact-rated rear door window was added in '22 for enhanced security, & exterior doorknobs, deadbolts & keys were also replaced. More recently, the home received new exterior paint in '26 & new interior paint in '26. Enjoy the everyday convenience of reserved parking directly in front of the unit's door, along with ample guest parking throughout the gated community & specifically near this unit! Countryside Key also offers a community pool overlooking the pond, tennis courts, & a designated storage area for camper vehicles, boats, trailers, &/or commercial vehicles (subject to association requirements - see HOA). This INCREDIBLE LOCATION is conveniently positioned near the Hillsborough County line & just minutes from the charm, restaurants, waterfront parks & activities of Safety Harbor. You're also only 8.7 miles from beautiful Honeymoon Island State Park and its Gulf beaches, with convenient access to Tampa International Airport, shopping, dining, entertainment and major roadways connecting you throughout the Tampa Bay area (all points). This Countryside Key townhome offers an exceptional combination of privacy, convenience, value & move-in-ready living.

279 Countryside Key Boulevard, Oldsmar
366 Countryside Key Boulevard, Oldsmar
$229,500
2 Beds ⋅ 3 Baths ⋅ TB8534362 MLS ⋅ N/A BLDG.
Welcome to this 2-bedroom, 2.5-bath townhome located in the desirable gated community of Countryside Key in the heart of Oldsmar. This spacious floor plan features two primary suites upstairs, each with its own private bathroom, while the convenient half bath downstairs is perfect for guests. Enjoy an open living and dining area with plenty of natural light and a private screened patio ideal for relaxing or entertaining. The seller is offering a concession toward new flooring and/or appliances, providing a great opportunity to personalize the home to your own style. Residents of Countryside Key enjoy access to a community pool, tennis courts, and beautifully maintained grounds, all just minutes from shopping, dining, parks, top-rated schools, Tampa International Airport, and the beaches.

366 Countryside Key Boulevard, Oldsmar
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