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239 Countryside Key Boulevard, Oldsmar
$245,000
2 Beds ⋅ 2 Baths ⋅ Countryside Key SubDv. ⋅ 34677 Zip Code
Welcome to this beautifully maintained 2 Bedroom, 1.5 Bath townhome located in the highly desirable gated community of Countryside Key in Oldsmar. This move-in ready home features NEW INTERIOR PAINT (2025) in soft neutral tones, LUXURY VINYL PLANK FLOORING (2023) on the first level, and NEW CARPET (October 2025) on the second floor. The bright and inviting open-concept layout includes spacious family and dining rooms at the front of the home and a kitchen and laundry area at the rear, complete with NEW STAINLESS-STEEL REFRIGERATOR, DISHWASHER, AND RANGE (2023), plus a MICROWAVE (2018). Sliding doors lead to a PERMITTED ENCLOSED PORCH (2007) featuring HURRICANE IMPACT WINDOWS—an ideal space for morning coffee or evening relaxation. Metal shutters designed to fit over the lanai windows will also convey with the sale, providing added protection. Upstairs, you’ll find two nicely sized bedrooms and a full bath that has been thoughtfully reconfigured to include a LARGE WALK-IN SHOWER and a VANITY WITH DUAL SINKS. Additional updates include a NEW HVAC (2023), WATER HEATER (2020), HURRICANE IMPACT WINDOWS (rear 2018, front 2025), NEW STORM DOOR (2020), NEW GUTTERS (June 2025), and UPDATED LIGHTING AND CEILING FANS throughout. The WASHER AND DRYER (2022) will also convey with the sale. The HOA takes care of nearly everything, including water, internet/cable, exterior building insurance, sewer, trash, landscaping, exterior maintenance, and pest control—providing exceptional value and ease of living. Countryside Key residents enjoy access to a community pool, tennis courts, and gated security. Ideally located close to shopping, dining, and entertainment in Oldsmar and Countryside, and just minutes from Safety Harbor, Dunedin, Honeymoon Island, and Tampa International Airport, this home offers the perfect combination of comfort, convenience, and the relaxed Florida lifestyle.

239 Countryside Key Boulevard, Oldsmar
421 Countryside Key Boulevard, Oldsmar
$245,000
2 Beds ⋅ 3 Baths ⋅ Countryside Key SubDv. ⋅ 34677 Zip Code
Bright, Welcoming, and Ready to Greet You with a Smile Welcome to 421 Countryside Key, an adorable 2-bedroom, 2.5-bathroom townhome in a gated community with reserved parking, abundant natural light, and a layout designed for easy Florida living. Step inside to a bright, open living and dining area flowing seamlessly into the kitchen, perfect for everyday living and entertaining. A half bath and laundry closet add convenience on the first floor, while the screened lanai offers a relaxing spot for morning coffee or evening breezes. Upstairs, both spacious bedrooms feature private ensuite bathrooms, providing comfort and flexibility for guests, family, or a home office. The only carpeted area is the stairs, with low-maintenance flooring throughout the rest of the home. Enjoy the benefits of gated community living in a prime location close to shopping, dining, and major routes for an easy commute. Don’t miss the chance to make this light-filled, welcoming townhome your new place to call home in Countryside Key—and we’re confident you’ll leave with a smile.

421 Countryside Key Boulevard, Oldsmar
467 Countryside Key Boulevard, Oldsmar
$240,000
2 Beds ⋅ 3 Baths ⋅ Countryside Key SubDv. ⋅ 34677 Zip Code
PRICE IMPROVEMENT - Motivated seller! Move-in ready 2BR/2.5BA townhome in gated Countryside Key with a wonderfully updated kitchen in 2024 open layout, and screened patio overlooking the pond. This townhome has been meticulously kept by it's current owner, making it truly move-in ready. Both bedrooms upstairs feature en-suite baths and plenty of closet space. HOA fee of only $433/month covers roof, exterior, landscaping, building insurance, water, sewer, trash, cable, internet, pool, tennis, and gated security—making maintenance worry-free. Prime Oldsmar location between Tampa & Clearwater, just minutes to shopping, dining, TPA, and Gulf beaches. Don't miss the chance to capture your slice of Countryside Key!

467 Countryside Key Boulevard, Oldsmar
273 Countryside Key Boulevard Unit N/A, Oldsmar
$235,000
2 Beds ⋅ 3 Baths ⋅ Countryside Key SubDv. ⋅ 34677 Zip Code
Welcome home to this beautifully maintained MOVE-IN READY 2-bedroom, 2.5-bath townhome in the desirable gated community of Countryside Key! With 1,110 sq. ft. of comfortable living space plus an enclosed 75 sq. ft. patio, this home offers both style and practicality—perfect for today’s busy lifestyle. Step inside to find tile flooring throughout the main level and luxury vinyl plank upstairs—no carpet anywhere! The bright kitchen features updated stainless steel appliances, including a NEW dishwasher and microwave, a modern backsplash, and plenty of cabinetry. The open-concept living and dining area flows seamlessly to the enclosed patio—ideal for an office, workout space, or peaceful retreat. Upstairs, each bedroom has its own private en-suite bathroom, providing the perfect setup for guests or roommates. The primary suite showcases a fully updated walk-in shower and spacious closet. Additional updates include fresh interior paint, 5” baseboards, ceiling fans, and a newer A/C unit (2021)—everything’s ready for you to move right in! Located in a secure, gated community, Countryside Key offers boat, trailer, camper, and commercial vehicle parking—a rare find! HOA fees cover landscaping, irrigation, pest control, exterior maintenance, structural insurance, and Spectrum internet and cable for low-stress living. Enjoy an unbeatable location close to shopping, dining, top-rated schools, and commuter routes, all while living in a well-maintained and welcoming community. Bring an offer for this motivated seller.

273 Countryside Key Boulevard Unit N/A, Oldsmar
367 Countryside Key Boulevard, Oldsmar
$235,000
2 Beds ⋅ 2 Baths ⋅ Countryside Key SubDv. ⋅ 34677 Zip Code
Beautifully updated 2BR/1.5BA townhouse in the desirable gated community of Countryside Key! This move-in ready home features an open-concept living area, a newly renovated kitchen (2024) with granite counters, stainless steel appliances, and modern cabinetry. Upstairs offers two spacious bedrooms with vaulted ceilings and an updated full bath. Enjoy peace of mind with impact-rated windows and a private patio perfect for relaxing. Community amenities include a pool, tennis courts, car wash area, and optional boat/RV storage. HOA covers water, sewer, trash, cable, internet, lawn care, and exterior maintenance. Conveniently located near shopping, dining, parks, and award-winning beaches. Seller is ready to make a deal—schedule your showing today!

367 Countryside Key Boulevard, Oldsmar
388 Countryside Key Boulevard, Oldsmar
$234,000
2 Beds ⋅ 2 Baths ⋅ Countryside Key SubDv. ⋅ 34677 Zip Code
2025 HVAC! Assumable FHA Loan! Welcome to 388 Countryside Key, a charming 2-bedroom, 1.5-bathroom townhome located in the highly sought-after Oldsmar, FL community. This delightful two-story residence boasts an open-concept first floor with a spacious kitchen, ample cabinetry, a generous pantry, and a convenient laundry/utility closet with a full-size washer and dryer. The living and dining areas flow seamlessly, enhanced by a kitchen bar and a convenient first-floor half bath. Upstairs, you'll find two generously sized bedrooms, each featuring vaulted ceilings that create an airy ambiance. Step outside to your enclosed screened patio, a serene retreat perfect for unwinding and enjoying the Florida weather year-round. This pet-friendly community offers a wealth of amenities including a secure gate, sparkling pool, tennis courts, sidewalks, and a car-wash station, with recreational storage for your RV, boat, or trailer available for a nominal fee. You'll have an assigned parking spot right at your doorstep with ample guest parking. Monthly HOA fees cover water, sewer, trash, cable, wifi, community pool, lawn and landscaping, roof maintenance and replacement, exterior pest control, and exterior building maintenance. Located in an area known for its highly-regarded school districts, buyers are encouraged to verify current school assignments and ratings. Situated near Tampa International Airport, St. Petersburg, and the area's stunning beaches, this gorgeous property offers an exceptional opportunity to create your dream home in a prime location. Don't miss out on this fantastic opportunity! Notable Features & Upgrades: HVAC-2025; Interior Paint-2025; Carpet-2017; Primary Bathroom Renovation-2016; Granite Countertops & Cabinets (Kitchen & Primary Bath)-2013; Upgraded Fixtures & Handles, Lights, Ceiling Fans.

388 Countryside Key Boulevard, Oldsmar
382 Countryside Key Boulevard, Oldsmar
$225,000
2 Beds ⋅ 2 Baths ⋅ Countryside Key SubDv. ⋅ 34677 Zip Code
Spectacular carefree living… Welcome to the gated community of Countryside Key. This lovely 2 story waterfront townhome perfectly combines luxury, style and functionality. This home offers 2 bedrooms, 1.5 baths with just over 1,100 sq ft of fine Florida living. The modern open floor plan is ideal for family gatherings and entertaining. The main living area boasts tile flooring and a convenient floor plan. Fabulous, spacious kitchen overlooks the great room and offers a raised breakfast bar, white cabinetry, granite countertop, dual undermount stainless steel sink and SS appliances including a ceran top range, built-in microwave, dishwasher and 3-door refrigerator. A perfectly situated half bath is freshly painted (4/2026) and ready for ease of living and accessibility for guests. Extend your living and entertaining outdoors through the sliding glass doors to the screened lanai overlooking the serene pond. The first floor also includes a laundry closet and the seller is generously including the washer and dryer. The second-floor features laminate flooring and offers a split bedroom plan for ultimate privacy. The primary bedroom has a private entrance to the bathroom featuring new plank tile flooring, dual vanity with granite countertops, undermount sink, tub/shower combination and plenty of additional cabinetry for storage. Additional features and updates include a new garbage disposal (2026). The water heater is 9 yrs old, and AC was replaced in 2011. Low monthly HOA fee includes grounds & building maintenance, cable, Internet, water, sewer, trash, community pool, and tennis courts. Convenient location with a short drive to TIA and close to shops, restaurants and our beautiful beaches …. true carefree Florida living!

382 Countryside Key Boulevard, Oldsmar
477 Countryside Key Boulevard, Oldsmar
$220,000
2 Beds ⋅ 2 Baths ⋅ Countryside Key SubDv. ⋅ 34677 Zip Code
Welcome to this Countryside Key townhouse offering 2 bedrooms and 1.5 baths in a gated, pet-friendly community with low HOA fees. Recent updates include a new bathroom vanity, new light fixtures throughout, and updated appliances. The first floor features a spacious living area, half bath, kitchen, and a screen-enclosed lanai with peaceful pond views and a large storage closet. Upstairs, you'll find two generously sized bedrooms with laminate wood flooring and a large full bath. Countryside Key offers resort-style amenities, including a community pool, tennis courts, car wash area, and optional boat/RV storage. This is a very dog-friendly community, two pets allowed with no weight limit. The low HOA fee covers water, sewer, trash, cable, internet, lawn care, and exterior maintenance, providing easy, low-maintenance living. Conveniently located within walking distance to a recently renovated shopping plaza, and just minutes from award-winning Gulf beaches, downtown areas, dining, entertainment, and major commuter routes to Tampa.

477 Countryside Key Boulevard, Oldsmar
244 Countryside Key Boulevard, Oldsmar
$191,000
2 Beds ⋅ 3 Baths ⋅ Countryside Key SubDv. ⋅ 34677 Zip Code
Cozy 2-Bedroom, 2.5-Bath Townhome in the heart of Oldsmar. Brand new fresh carpets. The monthly HOA fees cover a wide range of services, including water, sewer, trash, cable, wifi, community pool, lawn and landscaping, roof maintenance and replacement, exterior pest control, and exterior building maintenance. Enjoy the convenience of being just minutes from the shopping, dining, a movie theater, parks, bike trail and more.

244 Countryside Key Boulevard, Oldsmar