Harbor Oaks Homes with Custom Architectural style

Welcome to Harbor Oaks, an enchanting subdivision nestled in the heart of Longboat Key, Florida. This picturesque community is a hidden gem in Sarasota County, offering residents a serene coastal lifestyle complemented by stunning custom architectural homes.

Harbor Oaks is renowned for its unique and diverse architectural styles, where each residence reflects the individuality of its owner while harmonizing beautifully with the lush surroundings. From Mediterranean-inspired villas to contemporary coastal retreats, the homes here are a testament to thoughtful design and craftsmanship. You’ll find expansive floor plans, high-end finishes, and breathtaking views that create a perfect backdrop for both relaxation and entertaining.

The community’s prime location offers unparalleled access to the pristine beaches of Longboat Key, where you can soak up the sun, enjoy water sports, or take leisurely strolls along the shoreline. Additionally, residents benefit from a vibrant local culture, with an array of upscale dining, boutique shopping, and recreational activities just a short drive away.

Harbor Oaks is not just a place to live; it's a lifestyle. With its lush landscaping, friendly neighbors, and a strong sense of community, you’ll feel right at home in this idyllic setting. Whether you’re looking for a seasonal getaway or a permanent residence, Harbor Oaks promises an exceptional living experience that embodies the best of Florida’s coastal charm. Explore the possibilities and discover your dream home in this charming subdivision today!

Newest Harbor Oaks Homes with Custom Architectural style

$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

Start Your Search