The Oaks Homes with Trees/Woods View

The Oaks Homes with Trees/Woods View

Welcome to The Oaks, an enchanting subdivision nestled in the heart of Florida, where nature and luxury converge to create a serene living experience. This picturesque community is characterized by its lush landscapes and stunning homes, each thoughtfully designed to blend seamlessly with the surrounding environment.

One of the standout features of The Oaks is the breathtaking views of trees and woods that adorn many of the residences. Imagine waking up to the gentle rustle of leaves and the soothing sounds of nature right outside your window. These homes are not just places to live; they are sanctuaries that invite tranquility and relaxation into your daily life. The abundant greenery provides a perfect backdrop for outdoor activities, enhancing your connection with nature while offering a sense of privacy and seclusion.

The Oaks is more than just a beautiful setting; it is a vibrant community that fosters a strong sense of belonging. Residents enjoy access to a variety of amenities, including walking trails, parks, and recreational facilities, making it easy to embrace an active lifestyle. Whether you prefer a leisurely stroll under the shade of towering trees or a fun-filled day at the community playground, The Oaks has something for everyone.

With its prime location in Florida, The Oaks offers convenient access to shopping, dining, and entertainment options, ensuring that everything you need is just a short drive away. Experience the charm of The Oaks, where your dream home awaits amidst the beauty of nature. Discover a lifestyle that is not only luxurious but also deeply connected to the serene landscapes that surround you.

Newest The Oaks Homes with Trees/Woods View

452 Blue Garden Lane, Osprey
$1,925,000
3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
Experience exceptional luxury and privacy in this Updated, custom Bo MacEwen residence, ideally situated on a beautifully landscaped cul-de-sac homesite in the prestigious gated community of Oaks Bayside. A welcoming approach features a long paver driveway, side-entry garage, and generous guest parking. Inside, architectural details take center stage with a dramatic two-story domed foyer, 11-foot ceilings, custom millwork, crown molding, tray ceilings, travertine flooring, abundant natural light, and oversized doors throughout. Designed for both elegant entertaining and comfortable everyday living, the open great room features a fireplace and flows seamlessly into a chef-inspired kitchen appointed with custom wood cabinetry, granite countertops, induction cooktop, double wall ovens, microwave drawer, and premium built-in appliances, including a wine cooler. The expansive primary suite offers a private retreat with ample sitting space, generous walk-in closets, and a beautifully appointed bath featuring dual vanities, dressing area, soaking tub, and glass-enclosed shower overlooking a secluded garden. Two additional guest suites, each with private en-suite baths, are thoughtfully positioned on the opposite side of this split floor plan. Outdoors, a recently renovated private courtyard creates an exceptional setting for relaxation and entertaining, featuring more than 1,500 square feet of covered and open-air space, a heated pool and spa, and convenient access to the main living areas and pool bath. Additional features include central vacuum, zoned HVAC with enhanced air filtration, hardwired security, integrated pool controls, and a Sonos/Sonance theater system. A distinctive combination of craftsmanship, architectural character, and private outdoor living in one of The Oaks' most desirable neighborhoods. The nearby, Private Dock on the Intracoastal Waterway is a cherished amenity of the Oaks-Bayside residents. 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**

452 Blue Garden Lane, Osprey
2912 Boating Boulevard, Kissimmee
$450,000
4 Beds ⋅ 2 Baths ⋅ The Oaks SubDv. ⋅ 34746 Zip Code
Virtually Staged. Welcome to this beautifully renovated home offering the perfect blend of luxury, comfort, and resort-style living! This move-in ready home features a brand-new roof installed in 2025, stylish tile flooring throughout, a fully updated interior, new appliances, and a built-in wine cooler that’s perfect for entertaining. Step outside to your private backyard oasis featuring a stunning screened-in pool completed in 2021, a fully equipped outdoor kitchen, and built-in speakers, creating the ideal space for relaxing or hosting family and friends. As a resident, you’ll also enjoy access to the community’s boating dock, tennis courts, and playground, providing endless opportunities for recreation and outdoor enjoyment. With modern upgrades, exceptional amenities, and a fantastic lifestyle, this home is one you won’t want to miss!

2912 Boating Boulevard, Kissimmee
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
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
152 Tall Oak Trail, Zolfo Springs
$115,000
The Oaks SubDv. ⋅ 33890 Zip Code
BEAUTIFUL WOODED FIVE ACRE PARCEL. A SEASONAL CREEK CALLED ALLIGATOR BRANCH RUNS THROUGH THIS PARCEL AND WHEN IT IS DRY A FUN CREEK BED TO WALK THROUGH. A VERY PEACEFUL PLACE TO CALL HOME OR A WEEKEND GET-A-WAY.

152 Tall Oak Trail, Zolfo Springs
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