Harbor Oaks Homes with Florida Architectural style

Welcome to Harbor Oaks, a hidden gem nestled in the picturesque Longboat Key, Florida. This charming subdivision offers a unique blend of tranquility and coastal living, making it an ideal destination for those seeking a serene lifestyle in one of the most sought-after areas of Sarasota County.

Harbor Oaks is characterized by its stunning homes that embody the quintessential Florida architectural style. Each residence is thoughtfully designed to harmonize with the lush tropical surroundings, featuring vibrant colors, spacious layouts, and open-air living spaces that invite the warm Florida sunshine indoors. Many homes boast private pools, expansive patios, and beautifully landscaped gardens, creating an oasis of relaxation right at your doorstep.

Living in Harbor Oaks means more than just enjoying exquisite homes; it’s about embracing a lifestyle filled with endless opportunities for outdoor adventures. With the sparkling Gulf of Mexico just moments away, residents can indulge in sun-soaked beach days, water sports, and leisurely strolls along the shore. The area is also home to a variety of upscale dining options, boutique shops, and cultural attractions, ensuring that you’ll never run out of things to do.

Whether you’re looking for a permanent residence or a seasonal retreat, Harbor Oaks offers a welcoming community atmosphere where neighbors become friends. Experience the charm of coastal living in this idyllic subdivision, and make Harbor Oaks your new home in Longboat Key, where every day feels like a vacation. Embrace the Florida lifestyle today!

Newest Harbor Oaks Homes with Florida 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

$594,900

3 Beds ⋅ 3 Baths ⋅ Harbor Oaks SubDv. ⋅ 34231 Zip Code

Some houses just have a vibe. This one has it in spades. Tucked away on a quiet dead-end street, this fully updated 3-bedroom, 3-bathroom mid-century modern home blends clean, classic lines with genuine personality — the kind of place that feels curated, not staged. Two of the three bedrooms come with their own ensuite baths, so privacy and convenience are built right in. Step inside and every detail has been thought through: newer appliances, custom closets throughout, and custom blinds that let in just the right amount of Sarasota sunshine. Out back, the good times continue. A permanent screened-in living space is made for long evenings, morning coffee, or watching the rain roll through without missing a beat. The yard is spacious and professionally landscaped, with pet turf that keeps things low-maintenance and always green — no mud, no fuss, just easy living. And then there's the bonus: a separate, private-entrance guest suite. Whether it becomes overflow space for visitors, a long-term income opportunity, or flexible living quarters for extended family, the possibilities are wide open — the layout gives you the freedom to decide what works best. Location seals the deal. This dead-end street offers a rare mix of privacy and convenience, with easy access to everything Sarasota living is known for — shopping, dining, culture, and the Gulf Coast lifestyle just minutes away. Homes that combine this level of updated detail with true flexible living space don't come around often in Sarasota's market. Come see what makes 2121 Palm Terrace special.

2121 Palm Terrace, Sarasota

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