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97 Sugar Mill Drive, Osprey
$1,950,000
5 Beds ⋅ 6 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
Welcome to an exceptional estate in The Oaks Bayside, where timeless elegance meets modern luxury in one of Sarasota County’s most prestigious gated communities. Perfectly positioned on a private, lush homesite beneath a canopy of majestic oaks, this stunning 5-bedroom, 6-bath residence offers the ideal blend of space, sophistication, and serenity. Step inside to discover a thoughtfully designed floor plan with expansive living areas, soaring ceilings, and an abundance of natural light. At the heart of the home is a completely renovated chef’s kitchen, featuring high-end finishes, premium appliances, custom cabinetry, and a seamless flow into the main living and entertaining spaces, perfect for both everyday living and hosting guests in style. Each of the five spacious bedrooms offers comfort and privacy, while the six bathrooms provide ample convenience for family and guests. Recent updates include a brand-new roof, and renovated kitchen, offering peace of mind and long-term value for the next owner. Outdoor living is equally impressive, with tranquil surroundings that capture the essence of Florida living, ideal for relaxing, entertaining, or simply enjoying the natural beauty that defines The Oaks Bayside. Residents enjoy access to The Oaks Club, a private, member-owned country club offering championship golf, tennis, fitness, dining, and a vibrant social lifestyle. Conveniently located near top-rated schools, beaches, dining, and shopping, this home delivers the perfect balance of privacy and accessibility. Experience refined living in one of the area’s most sought after communities, this is more than a home, it’s a lifestyle.

97 Sugar Mill 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

51 Macewen Drive Unit 5, 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

21 Bayhead Lane, Osprey
$789,000
3 Beds ⋅ 2 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
Beautifully updated and impeccably maintained, this 3-bedroom, 2-bath residence in The Oaks Preserve offers an exceptional combination of comfort, privacy, and gracious Florida living. Backing to a lush tropical preserve, the home enjoys a peaceful setting with a private pool and spa, inviting outdoor entertaining areas, and thoughtfully designed interiors. Beyond the residence, ownership provides access to the exceptional lifestyle of The Oaks, a private, member-owned country club with no current waiting list for Golf or Sports/Social membership. Pride of ownership is evident from the moment you arrive. A paver driveway leads to elegant double leaded-glass entry doors opening to a light-filled interior. A dedicated home office with plantation shutters offers a quiet workspace, while the formal dining room features a decorative ceiling and custom built-in buffet with glass-front cabinetry. The beautifully updated kitchen features granite countertops, stainless steel appliances, a breakfast bar, built-in wine and beverage cooler, and a convenient chef's desk. An adjoining breakfast nook with an aquarium window overlooks the pool and spa, bringing the outdoors into everyday living. The spacious primary suite offers a comfortable sitting area with a built-in window seat, generous walk-in closets, and an updated bath featuring dual sinks, granite countertops, a soaking tub, separate shower, and marble accents. Two additional bedrooms provide ample closet space and share an updated guest bath with granite and marble finishes. Outdoor living is equally inviting. The screened lanai features a generous covered entertaining area with an outdoor kitchen and ceiling fan, complemented by a sun-filled pool and spa overlooking the tropical preserve. Additional highlights include an air-conditioned two-car garage with epoxy flooring and abundant storage, along with access to the nearby Bishopscourt community pool. For added buyer confidence, the proactive sellers have completed property inspections in advance and are making the reports available for review, providing valuable information about the home's condition before purchase. Membership in The Oaks is required with homeownership and offers access to two championship golf courses, tennis, pickleball, croquet, fitness facilities, dining, and an active social calendar. With no current waiting list for either Golf or Sports/Social membership, buyers have the opportunity to begin enjoying the country club lifestyle without an extended membership wait.

21 Bayhead Lane, Osprey

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