The Oaks Homes with Water View

Welcome to The Oaks, a picturesque subdivision nestled in the heart of Osprey, Florida, just a stone's throw away from the stunning Nokomis beaches. This serene community is a hidden gem in Sarasota County, offering residents a perfect blend of luxury, tranquility, and natural beauty.

The Oaks is renowned for its exquisite homes, many of which boast breathtaking water views. Imagine waking up each morning to the gentle sounds of nature and the shimmering reflections of the sun on the water just outside your window. With meticulously landscaped grounds and a variety of architectural styles, these homes provide the ideal backdrop for a relaxed Florida lifestyle.

As you explore The Oaks, you'll discover a vibrant community filled with amenities designed to enhance your living experience. Residents have access to pristine golf courses, tennis courts, and a clubhouse that serves as a hub for social gatherings and events. The lush surroundings and scenic waterways create a perfect setting for outdoor enthusiasts, whether you enjoy kayaking, fishing, or simply taking leisurely strolls along the water's edge.

Located conveniently close to the charming boutiques, gourmet restaurants, and cultural attractions of Sarasota, The Oaks offers the best of both worlds—serenity and accessibility. Whether you're seeking a permanent residence or a seasonal retreat, The Oaks promises an unparalleled lifestyle in one of Florida's most desirable areas. Come and discover the beauty and elegance of living in a home with a water view at The Oaks—where your dream home awaits!

Newest The Oaks Homes with Water View

$1,649,000

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

$235,000

1 Beds ⋅ 1 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Discover a rare opportunity to own a serene retreat in The Oaks, one of Sarasota’s most sought-after private golf and country club communities. This bright, beautifully updated ground-floor studio is offered fully turnkey furnished, making it ideal as a seasonal getaway, or income-producing rental. Thoughtfully designed for both comfort and functionality, the open-concept layout seamlessly blends the living and sleeping areas. The updated kitchenette features dishwasher, oven, stove, fridge, freezer, microwave, quartz countertops, complemented by a dining nook and a convenient workspace. The modern bathroom includes a huge walk-in shower. Take in peaceful water views and picturesque scenes of the 18th fairway on the Eagle Course right from your patio. Residents of Windsor Lodge enjoy exclusive access to their own private pool. Short-term rentals are permitted, offering flexibility and excellent investment potential. Membership to The Oaks Club, a private, member-owned community renowned for its exceptional lifestyle amenities, is mandatory. Enjoy two championship golf courses, twelve tennis- and four pickleball courts, croquet lawns, pool and a state-of-the-art fitness and WellFit center. The expansive clubhouse features three dining venues, banquet facilities, and a vibrant social calendar. Perfectly positioned just 15 minutes from Siesta Key Beach, this property combines luxury living with unbeatable convenience in one of Sarasota’s premier locations.

51 Macewen Drive Unit 5, Osprey

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