The Oaks Homes with Traditional Architectural style

The Oaks Homes with Traditional Architectural style

Welcome to The Oaks, an enchanting subdivision nestled in the picturesque landscapes of Osprey and Nokomis, Florida. This serene community, located in Sarasota County, offers a perfect blend of luxury and comfort, making it an ideal choice for those seeking a tranquil lifestyle while remaining close to the vibrant culture of the Gulf Coast.

The Oaks is renowned for its stunning homes that showcase traditional architectural styles, exuding timeless elegance and charm. Each residence is thoughtfully designed, featuring classic elements such as gabled roofs, brick facades, and spacious porches that invite you to relax and soak in the beautiful surroundings. With an emphasis on quality craftsmanship and attention to detail, the homes here provide a warm and inviting atmosphere that truly feels like home.

Living in The Oaks means you’ll enjoy access to a wealth of amenities, including lush green spaces, scenic walking trails, and community parks, perfect for outdoor enthusiasts and families alike. Additionally, the subdivision is conveniently located near some of Florida's finest beaches, golf courses, and shopping districts, ensuring that residents have everything they need within reach.

Whether you’re sipping coffee on your front porch or hosting a gathering in your beautifully landscaped backyard, The Oaks offers a lifestyle of sophistication and relaxation. Experience the charm of traditional architecture combined with the natural beauty of Florida living—make The Oaks your new home today!

Newest The Oaks Homes with Traditional 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
$1,595,000
4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
Offered at a price approaching the value of the two buildable lots alone, this architect-designed estate represents one of the most compelling opportunities currently available in The Oaks. Nestled beneath majestic oak trees and surrounded by exceptional privacy, this architecturally significant residence was designed by and as the personal home of renowned architect Bo MacEwen. The property encompasses two buildable lots and includes a charming guest house, creating a rare and versatile estate setting. A grand foyer measuring approximately 12 feet wide by 19 feet long welcomes guests and leads to an impressive great room featuring soaring vaulted ceilings, a gas fireplace, and a dramatic bay window with built-in seating overlooking the beautifully landscaped grounds. Architectural details abound, including 14-inch crown molding, Palladian windows, wainscoting, skylights, custom lighting, and distinctive craftsmanship throughout. The home offers four bedrooms and four full bathrooms, thoughtfully designed to blend elegance, comfort, and timeless architectural character. Throughout the residence, quality construction and meticulous attention to detail reflect the vision of its celebrated designer. Step outside to discover a tranquil, resort-inspired setting featuring a sparkling pool, lush landscaping, and a separate guest house ideal for visitors, extended family, or a private office. In the evening, landscape lighting transforms the grounds into a serene retreat unlike anything else in the community. Residents of The Bayside enjoy a 24-hour guarded entrance and a private community pier perfect for kayaking, fishing, or taking in spectacular sunsets over Casey Key. Ownership also provides access to the exceptional lifestyle of The Oaks Club, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, the state-of-the-art WellFit Center, a Junior Olympic swimming pool, outstanding dining venues, and an active year-round social calendar. Club membership is required, and there is currently no waiting list for either Golf or Sports/Social membership.

75 Osprey Point Drive, Osprey
$285,000
1 Beds ⋅ 1 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top-of-the-line finishes and is accessible by both elevator and stairs. Offered turn-key furnished, the unit includes a full kitchen equipped with a full-size refrigerator, combination oven/microwave, cooktop and dishwasher. The open concept living and bedroom area is complemented by a full bathroom with a walk-in shower. It has a beautiful foyer, luxury laminate flooring, and is clean and well-maintained. From your window, you can enjoy lovely views out over the pool, across to the lake. This is an incredible opportunity to own your personal sanctuary, perfect for weekend golfers, vacationing guests or weekend get-a-ways. And you will appreciate the flexible rental policy. Windsor Lodge Residents have their own private swimming pool and club house. The Oaks, Sarasota’s premier golf and country club, has two championship golf courses, an outstanding tennis program, pickle ball and croquet courts, a junior Olympic community pool, state-of-the-art fitness center and offers a wide variety of dining, recreational and social options.

51 Mac Ewen Drive Unit 14, Osprey
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