Harbor Oaks Homes with Florida Architectural style

Welcome to Harbor Oaks, a stunning subdivision nestled in the picturesque Longboat Key, Florida, within Sarasota County. This hidden gem boasts a unique blend of coastal charm and modern elegance, making it a highly sought-after destination for those looking to embrace the quintessential Florida lifestyle.

Harbor Oaks is characterized by its enchanting homes, each showcasing the iconic Florida architectural style. This distinctive design seamlessly integrates indoor and outdoor living, allowing residents to enjoy the gentle sea breezes and breathtaking waterfront views. With spacious layouts, high ceilings, and large windows, these homes are bathed in natural light, creating a warm and inviting atmosphere. The use of vibrant colors and tropical landscaping further enhances the aesthetic appeal, making each property a true reflection of Florida’s natural beauty.

Living in Harbor Oaks means you’re just moments away from the pristine beaches of Longboat Key, where you can indulge in sun-soaked days and stunning sunsets. The community is also conveniently located near upscale dining, boutique shopping, and recreational activities, ensuring that residents have everything they need right at their fingertips.

Whether you’re seeking a permanent residence or a vacation retreat, Harbor Oaks offers a tranquil escape from the hustle and bustle of everyday life. Experience the perfect blend of luxury, comfort, and Florida’s unique charm in this idyllic subdivision. Discover your dream home in Harbor Oaks, where every day feels like a vacation!

Newest Harbor Oaks Homes with Florida Architectural style

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

$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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