The Oaks Homes with Custom Architectural style

The Oaks Homes with Custom Architectural style

Welcome to The Oaks, a prestigious subdivision nestled in the heart of Sarasota County, Florida, where luxury meets tranquility in the charming communities of Osprey and Nokomis. This exclusive neighborhood is renowned for its stunning custom architectural homes, each uniquely designed to reflect the individuality and lifestyle of its residents.

As you stroll through The Oaks, you'll be captivated by the meticulously landscaped streets lined with majestic oak trees, providing an idyllic backdrop for your dream home. The architectural styles here range from Mediterranean-inspired villas to contemporary masterpieces, ensuring that every home is a statement of elegance and sophistication. With spacious floor plans and high-end finishes, these residences are perfect for both entertaining and everyday living.

Living in The Oaks means embracing a lifestyle of leisure and comfort. Residents enjoy access to a wealth of amenities, including a private golf course, a luxurious clubhouse, and serene walking trails that wind through lush greenery. The community is also conveniently located near pristine beaches, upscale shopping, and fine dining, making it easy to indulge in the best that Sarasota County has to offer.

Whether you’re seeking a peaceful retreat or an active lifestyle, The Oaks provides the perfect blend of luxury and community. Experience the charm of Osprey and Nokomis, where every day feels like a vacation. Discover your forever home in The Oaks, where custom architectural beauty awaits you.

Newest The Oaks Homes with Custom Architectural style

$1,900,000
5 Beds ⋅ 8 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
Virtually Staged. A rare canvas of luxury, positioned on a lush double lot within the sought-after, gated community of The Oaks, in Osprey, adjacent to stunning Sarasota, known for the arts. Bordering the Heron Course on the eighth fairway, this iconic two-story estate boasts incredible opportunity for limitless potential. The entire interior is freshly painted, to enhance vision of stateliness. With five bedrooms, 7.5 baths and a sprawling layout, this magnificent property is an exceptional backdrop, just waiting for your personal touch. Arrive in style via the elegant front circular driveway or utilize the private rear driveway leading to a rare four-car garage. Inside, the home is masterfully designed for grand entertaining and everyday comfort, with a sweeping curved stairway at the entrance, setting the stage to an exquisite residence. The first floor features a formal living room and a sun-drenched family room complete with a fireplace, custom built-ins and multiple French doors, leading to the outdoor bliss. A screened lanai lays the foundation for Florida living at its finest, showcasing an enormous 33-by-46-foot sparkling heated pool and spa, expansive patio and an outdoor kitchen. The expansive open kitchen is a chef's dream, flowing seamlessly into a casual breakfast nook. For formal affairs, the large dining room offers custom cabinetry and an adjacent wet bar. The main-floor primary retreat is a sanctuary, featuring a dedicated sitting area and luxurious dual en-suite baths. There is more closet space than a clothes diva could possibly desire. The first floor is completed by a handsome office/library with built-ins, a powder room and a guest bedroom. Upstairs, you will find three additional en-suite bedrooms, one of which benefits from private back-staircase access, ideal for an au pair, in-laws or VIP guests. With every bedroom featuring its private bath, privacy is guaranteed for all. Outdoors, the walled double lot provides a private tropical oasis, all with tranquil, serene views. On a practical note, roof was replaced in 2019, with hurricane shutters, for peace of mind. Two 18-hole championship golf courses, 12 Har-Tru tennis courts (four lighted), croquet and pickleball courts, a state-of-the art fitness center, fine and casual dining options and a calendar of social events, The Oaks is Sarasota’s leading golf and country club.

916 Macewen Drive, Osprey
$4,790,000
4 Beds ⋅ 6 Baths ⋅ The 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
$1,289,000
3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
One or more photo(s) has been virtually staged. Designed by renowned architect Frank Folsom Smith, this timeless residence is privately positioned on an expansive double lot at the end of a quiet cul-de-sac within The Oaks Preserve. The property is framed by lush conservation views and mature oak canopies and blends classic architectural character with thoughtfully curated updates. Professional lawn care and irrigation are covered by the monthly fees. Designed for both everyday comfort and effortless entertaining, the residence offers 3 bedrooms, 3.5 baths, multiple indoor and outdoor gathering spaces, and a seamless connection to its tranquil natural surroundings. Inside, refined architectural elements, including crown molding, hardwood flooring, custom millwork, vaulted ceilings, plantation shutters, and two fireplaces, create a warm yet elevated aesthetic throughout. The great room opens effortlessly to the screened Florida room and private outdoor living spaces, while the dining room’s built-in serving bar and wine chiller complement the beautifully updated kitchen featuring custom white cabinetry, granite countertops, stainless steel appliances, an oversized island, and curated designer lighting. A Sonos sound system extends throughout the residence. The primary suite serves as a retreat with vaulted ceilings, a bay window sitting area, outdoor access, and a fully renovated spa-inspired bath completed in 2023. Dramatic marble-look tile, a frameless glass shower, dual vanities, and a freestanding soaking tub positioned beneath a skylight create a serene, resort-like experience. Additional baths have also been extensively renovated with elevated finishes and designer fixtures, while the updated laundry room introduces custom storage, shiplap detailing, and functional built-ins with a refined coastal aesthetic. Upstairs, a spacious bonus room with a fireplace opens directly to a newly renovated second-story deck. With a full bathroom, the second floor is an exceptional flex space ideal for guests, recreation, or private lounging among the treetops. Outdoor living is equally compelling, centered around a seven-foot-deep heated pool and spa surrounded by brick pavers, tropical landscaping, and serene preserve views with no rear neighbors. Recent improvements include a new pool heater, filtration system, pump and motor, new lanai screening and aluminum framing, exterior paint completed in 2025, new air conditioning for the main floor, and a new second-story flat roof with a warranty. Located within the gated community of Bishops Court inside The Oaks Preserve, residents enjoy 24 hour guarded gates, maintenance-free living alongside access to one of the region’s premier private club lifestyles, featuring two championship golf courses, Har-Tru tennis courts, pickleball, croquet, a state-of-the-art fitness center, fine and casual dining, and an active social calendar. Golf or Social Membership is required with homeownership. The Oaks Club has been awarded the Platinum Clubs of America, Distinguished Emerald Residential Country Club, and Audubon International Certified designations. Located between Sarasota and Venice, Osprey is known for its natural beauty, waterfront lifestyle, and easy access to everyday conveniences. Residents are just moments from Siesta Key, downtown Sarasota’s dining and cultural attractions, marinas, shopping, Legacy Trail, and the renowned Pine View School, creating an ideal setting for both year-round living and seasonal enjoyment.

156 Bishops Court Road, Osprey
$2,399,000
4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes, including newer impact windows, retractable window walls, a sleek tile roof, custom concrete flooring, and exquisite baths and fixtures to go along with the state-of-the-art kitchen, equipped with top-tier Wolf and Sub-Zero appliances. Soaring vaulted ceilings create an expansive, airy ambiance, while large windows frame stunning lake views, offering the perfect backdrop for the sparkling pool and expansive spa, complete with tranquil water features. With disappearing sliders throughout, the home can let the air and light flow easily from outside to in. Enjoy breathtaking sunsets from your private oasis or stroll a kayak or paddleboard to the nearby boat launch for effortless access to Sarasota Bay and the Gulf, thanks to the newly reopened Midnight Pass. Situated on a secluded .40-acre lot, this property offers a serene retreat, featuring a Zen garden surrounded by lush landscaping. Residents of The Oaks enjoy world-class amenities, including championship golf, fine dining, tennis, fitness, and swimming. At 49 Osprey Point Drive, every detail has been meticulously crafted for those who seek refined living and unparalleled elegance.

49 Osprey Point Drive, Osprey
$2,395,000
3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
**CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country Club community and offers a Lovely, Golf Course View of the 17th Fairway of the interior, Heron Golf Course. This Spacious, Light and Bright, Open Floorplan of OVER 4500sf entails 3-BEDS, 3 FULL and 1 HALF BATHS, Study/Den, Bonus Room / Entertaining area with Fireplace and Wetbar, 3-CAR GARAGE, etc. Premium features abound including Crown moldings, Marble and wood floors, Coffered ceiling, Custom built-ins, a well-equipped kitchen with Granite countertops, Stainless Steel Appliances including KitchenAid and Fisher & Paykel, and much more! An Expansive Primary Bedroom Suite features a Bonus Room, Walk-In Closet, dual vanities, soaking tub and custom-tiled shower. Enjoy OUTDOOR LIVING at its FINEST in an Expansive, Screened Lanai with PEBBLETEC Pool & Spa and Outdoor Kitchen in a serene setting. ROOF (2015). THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **Please Enjoy Viewing the 3D VIRTUAL TOUR**

852 Macewen Drive, Osprey
$1,595,000
3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
**STUNNING GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** situated on an Over Half Acre Lot overlooking the 12th Fairway of the interior, HERON GOLF COURSE. With its delightful curb appeal and manicured landscape, this splendid residence offers 3 BEDROOMS + Spacious Executive Office/Study, 3 FULL and 1 HALF BATHS, High Ceilings, Crown Moldings, Gas Fireplace, spacious Kitchen with Granite Counters and Stainless Steel appliances, 2-Car Garage w/ Circular Driveway, and much more! An Expansive Primary Bedroom Suite features multiple walk-in closets and an Updated Primary Bathroom with dual vanities, soaking tub, custom-tiled shower and private outdoor shower. Ultimate enjoyment of the outdoors is made possible with an expansive screened lanai featuring a Large 45ft Pebble-Tec Pool & Spa, Outdoor Kitchen space (without appliances) and an abundant covered seating area. Recent UPDATES include Freshly Painted Interior (2024), NEW POOL CAGE (2023), NEW ROOF (2018), HVAC (2018), Pool Pump, etc. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO**

909 Macewen Drive, Osprey
Start Your Search