Oaks Homes with Special Community Restrictions Community Features

Oaks Homes with Special Community Restrictions Community Features

Welcome to the Oaks, a picturesque and serene subdivision nestled in the charming coastal town of Osprey, Florida, just a stone's throw away from the pristine shores of Nokomis. This exclusive community offers a unique blend of luxurious living and natural beauty, making it an ideal destination for those seeking a tranquil lifestyle in the heart of Sarasota County.

The Oaks is renowned for its stunning homes, each thoughtfully designed to embody elegance and comfort. With an array of architectural styles, from Mediterranean villas to contemporary masterpieces, residents enjoy a diverse selection of properties that cater to various tastes and preferences. The community features special restrictions that ensure the preservation of its aesthetic appeal and the well-being of its residents. These guidelines help maintain the high standards of the neighborhood, creating a harmonious environment where neighbors can thrive together.

One of the standout features of the Oaks is its exceptional community amenities. Residents have access to a state-of-the-art fitness center, inviting swimming pools, and beautifully landscaped parks, perfect for leisurely strolls or family gatherings. Additionally, the community is conveniently located near top-rated schools, boutique shopping, and gourmet dining, ensuring that everything you need is just around the corner.

For those who appreciate a vibrant social scene, the Oaks also hosts numerous community events throughout the year, fostering connections among neighbors and creating lasting friendships. Embrace the lifestyle you’ve always dreamed of in the Oaks, where luxury meets community in the stunning backdrop of Florida’s Gulf Coast.

Newest Oaks Homes with Special Community Restrictions Community Features

$4,790,000
4 Beds 6 Baths Oaks SubDv. 34229 Zip Code
Lakefront living and elevated architecture come together at 101 Osprey Point Drive, a Bo MacEwen-designed estate privately positioned on nearly an acre within the gates of Sarasota’s prestigious Oaks Bayside community. Spanning more than 5,000 square feet across two of the community’s most desirable homesites with 150 feet of water frontage, the residence blends timeless architecture, exceptional entertaining spaces, and a tranquil resort-style setting surrounded by lush landscaping and sweeping water views. An oversized granite-tiled circular drive and stately double-door entrance create a memorable arrival, leading into interiors defined by soaring ceilings, white onyx flooring with marble inlays, handcrafted millwork, dramatic fireplaces, crystal chandeliers, and walls of French doors opening to the lakefront terrace and pool. Designed for both elegant entertaining and everyday comfort, the home offers a series of richly detailed gathering spaces including a formal living room with dual fireplaces, a lakefront dining room with custom built-ins, a domed-ceiling sitting room ideal for cocktails or conversation, and a custom bar and wine room with etched-glass cabinetry, stone countertops, and display shelving. The remodeled chef’s kitchen combines classic design with modern functionality, featuring UltraKraft cabinetry, custom soffit lighting, Corian countertops, a center island with breakfast bar, and premium appliances including a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, warming drawer, microwave, dual KitchenAid dishwashers, and wine refrigerator. A butler’s pantry and sunlit breakfast nook overlooking the gardens further enhance the home’s livability. The primary suite serves as a private retreat with a spacious sitting area, custom closets, and a spa-inspired bathroom renovated in 2025. Three additional guest suites with updated baths provide comfort and flexibility, including a separate suite ideally positioned for extended-stay guests, live-in assistance, or multigenerational living. Outdoor living is centered around an open-air pool, expansive entertaining deck, and cabana framed by mature landscaping and manicured hedges, creating a private oasis with peaceful lake views. Additional updates include refinished hardwood flooring, updated guest baths, and a Daikin 5-ton HVAC system installed in 2022. Located within The Oaks Club, residents enjoy access to one of Sarasota’s premier private club communities, offering two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center and spa, multiple dining venues, and a private community dock on Little Sarasota Bay. Just moments from Sarasota waterfront dining, Siesta Key beaches, and Sarasota/Venice cultural attractions, this distinguished lakefront estate presents an exceptional opportunity within one of the Gulf Coast’s most established luxury communities.

101 Osprey Point Drive, Osprey

Start Your Search