The Oaks Homes with Pool View

The Oaks Homes with Pool View

Welcome to The Oaks, an exquisite subdivision nestled in the heart of Osprey, Florida, just a stone's throw away from the pristine beaches of Nokomis. This stunning community is a hidden gem in Sarasota County, offering a perfect blend of luxury, tranquility, and natural beauty. With its lush landscapes, serene lakes, and mature trees, The Oaks provides an idyllic setting for those seeking a peaceful retreat while still being close to vibrant local amenities.

The Oaks is known for its elegant homes, many of which boast breathtaking pool views that enhance the overall charm of the residences. Imagine waking up to the gentle sound of water cascading from your private pool, surrounded by lush tropical foliage. These homes are designed with outdoor living in mind, featuring spacious patios and expansive windows that allow for an abundance of natural light and picturesque views.

Residents of The Oaks enjoy a wealth of amenities, including access to world-class golf courses, tennis courts, and a state-of-the-art fitness center. The community also fosters a strong sense of camaraderie, with numerous social events and activities that encourage neighbors to connect and create lasting friendships.

Conveniently located near the stunning Gulf Coast beaches, The Oaks offers easy access to shopping, dining, and cultural attractions in nearby Sarasota. Whether you're looking for a family home or a serene getaway, The Oaks is the perfect place to call home. Experience the charm of Florida living at its finest, where every day feels like a vacation. Welcome to The Oaks—your dream home awaits!

Newest The Oaks Homes with Pool View

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
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
909 Macewen Drive, Osprey
$1,595,000
3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
**STUNNING GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** situated on an Over Half Acre Lot overlooking the 12th Fairway of the interior, HERON GOLF COURSE. With its delightful curb appeal and manicured landscape, this splendid residence offers 3 BEDROOMS + Spacious Executive Office/Study, 3 FULL and 1 HALF BATHS, High Ceilings, Crown Moldings, Gas Fireplace, spacious Kitchen with Granite Counters and Stainless Steel appliances, 2-Car Garage w/ Circular Driveway, and much more! An Expansive Primary Bedroom Suite features multiple walk-in closets and an Updated Primary Bathroom with dual vanities, soaking tub, custom-tiled shower and private outdoor shower. Ultimate enjoyment of the outdoors is made possible with an expansive screened lanai featuring a Large 45ft Pebble-Tec Pool & Spa, Outdoor Kitchen space (without appliances) and an abundant covered seating area. Recent UPDATES include Freshly Painted Interior (2024), NEW POOL CAGE (2023), NEW ROOF (2018), HVAC (2018), Pool Pump, etc. 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. **ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO**

909 Macewen Drive, Osprey
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