Countryside Key Real Estate

Countryside Key Real Estate

Welcome to Countryside Key, a hidden gem nestled in the heart of Oldsmar, Florida, within the vibrant Pinellas County. This picturesque subdivision is renowned for its serene ambiance and family-friendly atmosphere, making it the perfect place to call home.

Countryside Key boasts a variety of beautifully designed single-family homes, each reflecting a unique charm and character. The lush, tree-lined streets are complemented by well-maintained lawns, creating a welcoming environment for residents and visitors alike. With a range of property sizes and styles available, there’s a perfect fit for everyone, from first-time buyers to those seeking a spacious family retreat.

One of the standout features of Countryside Key is its proximity to nature and recreational opportunities. Residents enjoy easy access to nearby parks, scenic walking trails, and the stunning waterfront of Old Tampa Bay. Whether you’re an outdoor enthusiast or simply looking to unwind in a tranquil setting, this community has it all. Plus, with top-rated schools and a variety of shopping and dining options just a stone’s throw away, you’ll find everything you need within reach.

Moreover, Countryside Key is conveniently located near major highways, providing quick access to the beautiful beaches of the Gulf Coast and the bustling cities of Tampa and St. Petersburg. This ideal location allows residents to enjoy the best of both worlds: a peaceful suburban lifestyle with the excitement of city living just minutes away.

Discover the charm and warmth of Countryside Key—where community spirit thrives and your dream home awaits!

Newest Listings in Countryside Key

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