The Oaks Homes with Traditional Architectural style

The Oaks Homes with Traditional Architectural style

Welcome to The Oaks, a picturesque subdivision nestled in the heart of Florida, where the charm of traditional architecture meets modern living. This enchanting community is designed for those who appreciate the timeless elegance of homes that boast classic lines and warm, inviting details.

As you stroll through the tree-lined streets of The Oaks, you’ll be captivated by the stunning array of traditional-style homes that grace the neighborhood. Each residence features unique architectural elements such as gabled roofs, expansive porches, and intricate brickwork, creating a cohesive yet diverse aesthetic that feels both welcoming and sophisticated. These homes are not just structures; they are a celebration of craftsmanship and design that stand the test of time.

Living in The Oaks means more than just owning a beautiful home; it’s about embracing a lifestyle. The community is thoughtfully designed with an abundance of green spaces, walking trails, and recreational areas, perfect for families, couples, and individuals alike. Enjoy leisurely afternoons at the nearby parks or take advantage of the vibrant local amenities that include shopping, dining, and entertainment options just a stone's throw away.

The Oaks is not just a place to live; it’s a community where neighbors become friends and memories are made. With its ideal location in sunny Florida, you can enjoy year-round outdoor activities, from beach days to hiking adventures. Experience the best of both worlds with the charm of traditional architecture and the conveniences of modern living at The Oaks—your dream home awaits!

Newest The Oaks Homes with Traditional Architectural style

75 Osprey Point 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
51 Mac Ewen Drive Unit 14, 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
1524 The Oaks Boulevard, Kissimmee
$524,900
4 Beds ⋅ 3 Baths ⋅ The Oaks SubDv. ⋅ 34746 Zip Code
Positioned along the 13th hole of The Oaks National Golf Course in Kissimmee, this golf-front residence offers elegant interiors, updated systems and a layout designed for comfort and entertaining. The four-bedroom, two-and-one-half-bath home features a flexible floor plan with high ceilings and abundant natural light throughout. The first-floor primary suite overlooks the course and private pool, with a spacious bath offering dual vanities, soaking tub, separate shower and walk-in closets. The kitchen includes granite countertops, wood cabinetry, decorative backsplash, accent lighting, reverse osmosis system and newly installed appliances. A wine storage feature adds to the home’s entertaining appeal. Upstairs, three generously sized bedrooms are joined by a double loft-style flex space, ideal for use as a media lounge, home office or playroom. Outdoor living is enhanced by a custom pool and spa with slate waterfall, surrounded by slate decking, mature landscaping and a double-height screened enclosure. A professionally designed irrigation system supports the landscaped grounds. Smart-home features include Alexa-enabled lighting and a Ring doorbell. Recent upgrades include a new roof and HVAC system in 2020, along with a fully paid-off solar system offering long-term energy savings. Community amenities include tennis courts, parks and playgrounds, with convenient access to local shopping, dining and attractions.

1524 The Oaks Boulevard, Kissimmee
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