Countryside Key Real Estate

Countryside Key Real Estate

Welcome to Countryside Key, a hidden gem nestled in the heart of Oldsmar, Florida, within beautiful Pinellas County. This charming subdivision offers a perfect blend of suburban tranquility and convenient access to urban amenities, making it an ideal place for families, retirees, and everyone in between.

Countryside Key is characterized by its picturesque landscapes, featuring lush greenery and serene water views that create a peaceful atmosphere. The community is designed with a focus on outdoor living, boasting well-maintained walking trails, parks, and recreational areas that encourage an active lifestyle. Residents can often be seen enjoying leisurely strolls, biking, or gathering with friends at nearby picnic spots.

One of the standout features of Countryside Key is its proximity to some of the best attractions in the Tampa Bay area. Just a short drive away, you'll find stunning beaches, vibrant shopping districts, and a variety of dining options that cater to every palate. For those who appreciate the arts, the nearby cultural venues offer a rich tapestry of entertainment, from theater performances to art exhibits.

Families will appreciate the top-rated schools in the vicinity, ensuring that children receive a quality education while being part of a supportive community. With its friendly neighbors and active homeowner association, Countryside Key fosters a sense of belonging that makes every resident feel at home.

Whether you're looking to buy your first home, downsize, or invest in a property, Countryside Key is a community that promises a fulfilling lifestyle. Discover the charm and convenience of this delightful subdivision today!

Newest Listings in Countryside Key

$275,000
2 Beds ⋅ 2 Baths ⋅ Countryside Key SubDv. ⋅ 34677 Zip Code
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 ⋅ Countryside Key SubDv. ⋅ 34677 Zip Code
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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