The Oaks Homes with No Truck/RV/Motorcycle Parking Community Features

The Oaks Homes with No Truck/RV/Motorcycle Parking Community Features

Welcome to The Oaks, an exquisite community nestled in the heart of Sarasota County, Florida, where the charm of Osprey and Nokomis meets elegant living. This picturesque subdivision is a hidden gem, offering residents a serene lifestyle surrounded by lush landscapes and vibrant natural beauty.

The Oaks is renowned for its commitment to maintaining a tranquil environment, which is reflected in its community guidelines. One of the standout features of this neighborhood is its regulation against truck, RV, and motorcycle parking, ensuring that the streets remain clear and inviting. This thoughtful approach fosters a peaceful ambiance, making it an ideal setting for families and individuals who appreciate a well-kept community.

As you explore The Oaks, you’ll find a stunning array of homes that blend sophistication with comfort. Many of the residences boast spacious layouts, modern amenities, and beautiful outdoor spaces, perfect for relaxing or entertaining. The community is designed to enhance the quality of life with its array of amenities, including walking trails, parks, and access to nearby beaches, allowing residents to enjoy the best of Florida’s outdoor lifestyle.

Living in The Oaks means being part of a close-knit community that values harmony and aesthetics. With its prime location, you’ll find yourself just minutes away from the vibrant culture of Sarasota, renowned dining options, and world-class shopping. Embrace the opportunity to call The Oaks home, where every day feels like a vacation in paradise. Come and experience the tranquility and beauty that this exceptional community has to offer!

Newest The Oaks Homes with No Truck/RV/Motorcycle Parking Community Features

156 Bishops Court Road, Osprey
$1,289,000
3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
One or more photo(s) has been virtually staged. An expansive double lot, a quiet cul-de-sac setting and preserve views with no rear neighbors make this Bishops Court residence an exceptional private retreat. Mature oaks and lush landscaping frame the property, creating a sense of space and seclusion within this intimate gated enclave of The Oaks Preserve. Designed by renowned architect Frank Folsom Smith, the home pairs timeless architectural character with thoughtfully curated updates. Professional lawn care and irrigation are included in the monthly fees. The residence offers three bedrooms, three-and-a-half baths and inviting spaces that make the most of its natural surroundings. Hardwood floors, custom millwork, crown molding, vaulted ceilings, plantation shutters and two fireplaces bring warmth and character throughout. The great room flows into the screened Florida room and outdoor living areas, keeping the peaceful setting in view. A built-in serving bar and wine chiller enhance the dining room, while the updated kitchen features custom white cabinetry, granite countertops, stainless steel appliances, an oversized island and designer lighting. A Sonos sound system extends throughout the home. The primary suite offers its own quiet retreat, with vaulted ceilings, a bay-window sitting area and direct outdoor access. Renovated in 2023, the spa-inspired bathroom features marble-look tile, a frameless glass shower, dual vanities and a freestanding soaking tub beneath a skylight. The additional bathrooms have also been extensively renovated with designer fixtures and finishes. Custom storage, built-ins and shiplap detailing bring the same considered style to the laundry room. Upstairs, a spacious bonus room with a fireplace opens to a newly renovated second-story deck overlooking the treetops. Freshly painted in 2026 and complete with a full bathroom, this versatile level can serve as guest accommodations, a media room, home office, art studio or secluded lounge. Outside, the generous lot gives the pool area a remarkable sense of privacy. A seven-foot-deep heated pool and spa are surrounded by brick pavers and tropical landscaping, with tranquil preserve views beyond. Recent improvements include a new pool heater, filtration system, pump and motor; new lanai screening and aluminum framing; exterior paint completed in 2025; a new main-level air-conditioning system; and a new second-story flat roof with a warranty. Ownership in The Oaks Preserve provides access to The Oaks Club, where Golf or Social Membership is required with homeownership. Club amenities include two championship golf courses, Har-Tru tennis courts, pickleball, croquet, a fitness center, fine and casual dining, and a year-round social calendar. The Oaks Club has been recognized as a Platinum Club of America, a Distinguished Emerald Residential Country Club and an Audubon International Certified property. Located in Osprey between Sarasota and Venice, the home places Gulf Coast beaches, boating, the Legacy Trail, Oscar Scherer State Park, Pine View School, downtown Sarasota and historic Venice within easy reach.

156 Bishops Court Road, 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

852 Macewen Drive, Osprey
$2,395,000
3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
**CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country Club community and offers a Lovely, Golf Course View of the 17th Fairway of the interior, Heron Golf Course. This Spacious, Light and Bright, Open Floorplan of OVER 4500sf entails 3-BEDS, 3 FULL and 1 HALF BATHS, Study/Den, Bonus Room / Entertaining area with Fireplace and Wetbar, 3-CAR GARAGE, etc. Premium features abound including Crown moldings, Marble and wood floors, Coffered ceiling, Custom built-ins, a well-equipped kitchen with Granite countertops, Stainless Steel Appliances including KitchenAid and Fisher & Paykel, and much more! An Expansive Primary Bedroom Suite features a Bonus Room, Walk-In Closet, dual vanities, soaking tub and custom-tiled shower. Enjoy OUTDOOR LIVING at its FINEST in an Expansive, Screened Lanai with PEBBLETEC Pool & Spa and Outdoor Kitchen in a serene setting. ROOF (2015). 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**

852 Macewen Drive, Osprey

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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