Harbor Oaks Homes with Trail(s) Amenities

Welcome to Harbor Oaks, a hidden gem nestled in the picturesque Longboat Key, Florida. This charming subdivision, located in Sarasota County, offers a unique blend of coastal living and luxurious amenities, making it an ideal destination for those seeking a tranquil yet vibrant lifestyle.

As you stroll through the beautifully landscaped streets of Harbor Oaks, you’ll find a delightful array of homes that perfectly capture the essence of Florida living. Each residence is thoughtfully designed, featuring spacious layouts, modern finishes, and plenty of natural light. Many homes boast stunning views of the surrounding lush greenery and the sparkling waters of the Gulf, creating a serene escape right at your doorstep.

One of the standout features of Harbor Oaks is its access to picturesque trails that wind through the community. These trails provide residents with the perfect opportunity to enjoy the outdoors, whether it’s a leisurely morning walk, an invigorating jog, or a peaceful bike ride. Imagine starting your day with the gentle sounds of nature and the refreshing sea breeze, all while surrounded by the stunning beauty of Longboat Key.

In addition to the trails, Harbor Oaks is conveniently located near some of the best beaches, dining, and shopping that Longboat Key has to offer. Residents can indulge in fresh seafood, explore local boutiques, or simply relax on the sun-kissed shores.

Whether you’re looking for a permanent residence, a vacation home, or an investment property, Harbor Oaks presents an unparalleled opportunity to embrace the Florida lifestyle. Come discover the charm and elegance of this exceptional community today!

Newest Harbor Oaks Homes with Trail(s) Amenities

2101 Harbourside Drive Unit 1103, Longboat Key

$1,495,000

3 Beds ⋅ 3 Baths ⋅ Harbor Oaks SubDv. ⋅ 34228 Zip Code

3BR/2.5BA, 2,219 sf end-unit villa in gated Harbour Oaks at Bay Isles. Fairway views across hole #3 (White) of the Longboat Key Club golf course, plus a full-sized private heated pool on a large screened lanai. Three sliders open the living spaces to that outdoor room—ideal for gatherings, quiet evenings, and southwest-oriented sunsets over the greens. Renovated in a clean modern-farmhouse style: shiplap fireplace, new lighting and ceiling fans, paneled interior doors with dark hardware, and a wood-and-glass front door. The open, refreshed kitchen flows into the dining area overlooking the pool and golf course. The primary suite is a true retreat with multiple closets including a walk-in, double sinks, a newly tiled glass-enclosed shower, and a bathroom skylight. Two additional bedrooms and a bonus office with golf-course and garden-atrium views give the household room to work, guest, and spread out. Practical updates include a new roof with the assessment paid and a large two-car garage with epoxy floor and organized storage for beach and sports gear. Harbour Oaks residents have use of the private Bay Isles Beach Club on the Gulf (parking available). Longboat Key Club golf, tennis, pickleball, and dining are nearby by optional separate membership; the marina is a short walk, with slips available separately. Move-in ready Longboat Key living: golf-course backdrop, private pool, beach-club access, and lock-and-leave convenience behind the Bay Isles gates. Schedule your private showing and start living the island lifestyle.

2101 Harbourside Drive Unit 1103, Longboat Key

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