Countryside Key Homes with Shingle Roof

Countryside Key Homes with Shingle Roof

Welcome to Countryside Key, a picturesque subdivision nestled in the heart of Oldsmar, Florida, within the scenic Pinellas County. This charming community seamlessly blends tranquility with convenience, making it an ideal place for families, retirees, and everyone in between.

Countryside Key offers a delightful array of homes, each featuring classic shingle roofs that not only enhance the aesthetic appeal but also provide durability and protection against the Florida sun. The shingle roofs are a hallmark of the community, offering a timeless look that complements the lush surroundings. With a variety of floor plans and styles, potential homeowners can choose from cozy single-family residences to more spacious options, ensuring there’s a perfect fit for everyone.

Residents of Countryside Key enjoy a close-knit community atmosphere, with beautifully landscaped common areas and friendly neighbors. The subdivision is conveniently located near a wealth of amenities, including shopping centers, dining options, and recreational facilities. Outdoor enthusiasts will appreciate the proximity to parks and nature trails, perfect for leisurely strolls or family picnics.

Additionally, with Oldsmar’s vibrant community events and activities, there’s always something happening just around the corner. Whether you're looking to enjoy a quiet evening at home or engage with the lively local culture, Countryside Key offers the best of both worlds.

Discover your dream home in Countryside Key, where comfort, community, and convenience come together in perfect harmony. Experience the charm of Oldsmar living today!

Newest Countryside Key Homes with Shingle Roof

$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
$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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