Oaks Homes with Bay Front Water Frontage

Oaks Homes with Bay Front Water Frontage

Welcome to Oaks, a stunning subdivision nestled in the heart of Osprey, Florida, where the serene beauty of nature meets luxurious living. Located in Sarasota County, Oaks is renowned for its picturesque landscapes, lush greenery, and tranquil ambiance, making it an ideal haven for those seeking a peaceful lifestyle close to the vibrant Gulf Coast.

One of the standout features of this exquisite community is its breathtaking bay front waterfront homes. Imagine waking up to the gentle sounds of lapping waves and the sight of sun-kissed waters right at your doorstep. These meticulously designed residences offer more than just a home; they provide a lifestyle defined by elegance and relaxation. With direct access to the shimmering bay, residents can indulge in a variety of water activities, from kayaking to fishing, or simply enjoy the stunning sunsets that paint the sky in vibrant hues.

The Oaks community is not just about beautiful homes; it’s about fostering a sense of belonging. With well-maintained walking trails, parks, and community amenities, residents can enjoy an active lifestyle while connecting with neighbors. Additionally, the proximity to local attractions, including charming boutiques, gourmet dining, and pristine beaches, ensures that you’re never far from the excitement of coastal living.

Discover the perfect blend of luxury and tranquility at Oaks, where every day feels like a vacation. Embrace the opportunity to live in a community that truly celebrates the beauty of waterfront living in sunny Florida. Welcome home!

Newest Oaks Homes with Bay Front Water Frontage

168 Coastal Hammock Court, Osprey/Nokomis
$1,900,000
3 Beds ⋅ 4 Baths ⋅ Oaks SubDv.
Experience an extraordinary waterfront lifestyle in this distinctive 3-bedroom, 3.5-bath Mizner-inspired residence, ideally positioned along Little Sarasota Bay in the prestigious Oaks Bayside. Tucked away on an intimate cul-de-sac shared by just 3 homes, this exceptional property with close to 4,000 SF of living space, offers remarkable privacy, an enchanting Old Florida setting surrounded by mature oaks and lush tropical foliage, and captivating views and sunsets stretching across Little Sarasota Bay. Thoughtfully custom designed to embrace its spectacular surroundings, the home is filled with natural light and showcases beautiful architectural details throughout, including porcelain tile flooring, soaring 14-foot and tray ceilings, extensive custom millwork and built-ins, and walls of impact-rated windows and French doors framing the surrounding landscape and water views. Fresh interior paint and brand-new porcelain tile floors and carpeting in 2026 bring a crisp, refreshed feel to the residence while preserving its distinctive character. At the heart of the home, the kitchen features stone countertops, a Sub-Zero refrigerator, ASKO dishwasher, stainless steel appliances and generous workspace, opening comfortably to the home's main gathering areas. French doors create a seamless connection to the elevated pool and spa terrace, an inviting private retreat for entertaining, relaxing in the Florida sunshine or enjoying the bay breezes and spectacular evening skies. The expansive primary suite enjoys an entire level of its own, creating a true private retreat complete with a separate sitting room/office, custom built-ins, generous closet, dedicated laundry and an ensuite bath. The upper level provides exceptional privacy for family and guests with 2 additional bedrooms, a full bath, and flexible office/media space. The convenient 3+ car oversized garage with ample storage is on the ground floor. A brand new five-stop elevator will be installed to provide convenient access throughout the home, extending to the rooftop terrace where panoramic water views and unforgettable Florida sunsets take center stage. Enjoy ultimate peace of mind with a gas generator included on-site. Beyond the residence, ownership in The Oaks provides access to one of Sarasota's most established private country club lifestyles, with championship golf, racquet sports, state-of-the-art fitness, dining and an active social calendar. Community dock located on Little Sarasota Bay. Private, distinctive and surrounded by natural beauty, 168 Coastal Hammock Court presents a rare opportunity to enjoy gracious bayfront living in one of Sarasota's most coveted gated communities.

168 Coastal Hammock Court, Osprey/Nokomis

324 Osprey Point Drive, Osprey/Nokomis
$3,700,000
5 Beds ⋅ 5 Baths ⋅ Oaks SubDv.
Welcome to extraordinary living! This completely private oasis is perfectly positioned along North Creek in The Oaks Bayside, one of the most sought-after communities in South Sarasota. Situated on a lot and a half, the view is peppered with lush foliage, creating total seclusion and the feel of a luxury retreat. One of the most desirable floor plans in the community, with open flow and complete separation from the master suite and guest accommodations, creates a comfortable and highly functional living space. The casita provides the perfect separate space for an office, a studio or long-term guest accommodations, with stunning views from the second floor. Fine finishes and quality craftsmanship are showcased throughout this home, custom built by renowned contractor Baron Construction. Features include French oak flooring, quartz countertops, premium appliances, central vac, wired Sono speakers throughout the house, ADT security and Ring camerias around the exterior, and numerous custom details. The combined living and dining area provides an ideal setting for entertaining, opening directly to the outdoor pool and spa. For more casual gatherings, the spacious kitchen and breakfast nook flow seamlessly into the family room and out to the covered outdoor living space. This screened area is beautifully designed with a pool and spa, and grill. The covered areas and ceiling fans provide comfort for al fresco dining. The lots’ site is spectacular, with great water views, and areas to launch your kayak or paddleboard. Add in the practical features like a newer roof, oversized three car garage and huge pantry and you have found a home of distinction with no peer. The Oaks Bayside is a gated bayfront community within The Oaks. The distinguished private club offers 2 championship golf courses, pickleball and tennis courts, a state-of-the-art WellFit Center, exquisite dining options and a celebrated social calendar. The location provides convenient access to downtown Sarasota, dining, nightlife, and the cultural amenities of the Gulf Coast. Club membership is required with home ownership. There is currently no waiting list for either Golf or Sports/Social membership.

324 Osprey Point Drive, Osprey/Nokomis

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