Rolling Oaks Real Estate

Welcome to Rolling Oaks, a hidden gem nestled in the heart of Tarpon Springs, Florida. This charming subdivision in Pinellas County offers a unique blend of serene suburban living and vibrant community spirit, making it an ideal place to call home.

Rolling Oaks is characterized by its lush, tree-lined streets and beautifully landscaped yards, creating a picturesque environment that invites relaxation and outdoor enjoyment. The community is known for its friendly neighbors and welcoming atmosphere, fostering a sense of belonging that is often hard to find in today’s fast-paced world.

Residents of Rolling Oaks enjoy easy access to a variety of local amenities. Just a short drive away, you’ll find an array of shopping, dining, and entertainment options, including the famous Sponge Docks of Tarpon Springs, where you can indulge in delicious Greek cuisine and explore unique shops. For nature enthusiasts, the nearby parks and waterfront areas offer countless opportunities for hiking, fishing, and kayaking, allowing you to fully embrace the beautiful Florida lifestyle.

Families will appreciate the highly-rated schools in the area, ensuring that children receive a quality education while growing up in a safe and nurturing environment.

With its prime location, friendly community, and a wealth of recreational opportunities, Rolling Oaks stands out as a desirable neighborhood in Tarpon Springs. Whether you’re looking to settle down or invest in a vacation home, Rolling Oaks offers the perfect blend of comfort and convenience. Come discover the charm of Rolling Oaks and experience the best that Florida living has to offer!

Newest Listings in Rolling Oaks

$375,000

3 Beds ⋅ 2 Baths ⋅ Rolling Oaks SubDv. ⋅ 34689 Zip Code

Virtually Staged. Check out this Tarpon Springs stunner located on a gorgeous tree-lined street in the highly desirable Rolling Oaks community. This beautiful home features gorgeous tile flooring, soaring cathedral ceilings, and an inviting eat-in kitchen complete with a breakfast bar. The thoughtfully designed split-bedroom floor plan offers privacy and comfort, while the spacious primary suite boasts attractive laminate flooring and a walk-in closet. An inside utility room with additional storage adds convenience, and the tranquil screened porch overlooks a shady, fenced backyard, creating the perfect setting for relaxing or entertaining. Nestled in a quiet and established section of Tarpon Springs, Rolling Oaks offers a peaceful setting while remaining close to everything that makes the area so special. Enjoy easy access to the world-famous Tarpon Springs Sponge Docks, charming downtown Palm Harbor, Fred Howard Park, and the award-winning beaches of Honeymoon Island and Caladesi Island. This is Florida living at its finest—don't miss your opportunity to call this exceptional property home.

1672 Countrywood Street, Tarpon Springs

$415,000

4 Beds ⋅ 2 Baths ⋅ Rolling Oaks SubDv. ⋅ 34689 Zip Code

Welcome to this beautifully maintained 4-bedroom, 2-bathroom, 2-Car Garage home located in a sought-after neighborhood in Tarpon Springs—where homes rarely become available! Offering a spacious and inviting open floor plan, this residence is enhanced by soaring vaulted ceilings that create a bright, airy atmosphere perfect for both everyday living and entertaining. Step inside this lovely home and you’ll find beautiful wood-look tile flooring throughout the main living areas, combining style and durability, while the bedrooms offer easy-care laminate flooring for comfort and convenience. The kitchen is spacious with light cabinetry, stainless steel appliances, modern backsplash and breakfast bar. The Primary bedroom is located at the back of the home with ensuite bath, and access to the large screened rear porch. The primary bathroom has been tastefully updated with new faucets, toilet, shower fixtures, and a vent fan. The home features a split-floor plan which offers a hedge of privacy between the primary suite and the 3 additional guest bedrooms. The guest bathroom is beautiful with a large custom vanity with granite countertop, large decorative mirror and features newer shower fixtures with modern white tile in the shower/bath combo. Thoughtful updates throughout provide both comfort and peace of mind, including a 2018 roof, new Stainless-Steel appliances (2021), modern backsplash in kitchen (2025), a new hot water heater installed in 2023, updated smoke alarms throughout the home for added safety, while the living room and primary bedroom showcase newer ceiling fans for added comfort. Enjoy added confidence knowing this neighborhood experienced no flooding during the 2024 storms, and the home is located outside of the flood zone—meaning no flood insurance is required. With low HOA fees of just $150 per year, this property offers both value and peace of mind. Conveniently located near the iconic Tarpon Springs Sponge Docks, you’ll enjoy easy access to waterfront dining, shopping, and local culture. Love the beach? Sunset Beach and Fred Howard Park are just a short drive away! Plus, the home is zoned for excellent schools, making it an ideal choice for families and those looking to continue their education at nearby St. Pete College. This move-in ready home perfectly blends desirable updates, a rarely available location, and an exceptional layout—schedule your private showing today!

1640 Countrywood Street, Tarpon Springs

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