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**
Equipment:
- Built-In Oven
- Convection Oven
- Cooktop
- Dishwasher
- Disposal
- Dryer
- Electric Water Heater
- Microwave
- Range Hood
- Refrigerator
- Washer
- Wine Refrigerator
Interior Features:
- Built-in Features
- Cathedral Ceiling(s)
- Ceiling Fans(s)
- Central Vaccum
- Crown Molding
- High Ceilings
- Kitchen/Family Room Combo
- Living Room/Dining Room Combo
- Open Floorplan
- Primary Bedroom Main Floor
- Solid Wood Cabinets
- Split Bedroom
- Stone Counters
- Thermostat
- Tray Ceiling(s)
- Vaulted Ceiling(s)
- Walk-In Closet(s)
- Window Treatments
Exterior Features:
- Outdoor Shower
- Private Mailbox
- Private Yard
View:
- Trees/Woods
Amenities:
- Basketball Court
- Clubhouse
- Fence Restrictions
- Fitness Center
- Gated
- Golf Course
- Pickleball Court(s)
- Playground
- Pool
- Recreation Facilities
- Tennis Court(s)
- Vehicle Restrictions
Financial Information:
- Taxes: $7,782.86
- Tax Year: 2025
- Association Fee: $2,900.00
- Association Fee Frequency: Semi-Annually
Room Dimensions:
- Laundry: Inside, Laundry Room
School Information:
- Elementary School: Laurel Nokomis Elementary
- Middle School: Sarasota Middle
- Junior High: Sarasota Middle
- High School: Venice Senior High
Additional Information:
- Building Description: Custom, Florida
- MLS Area: 34229 - Osprey
- Total Square Footage: 5,167
- Price per Square Feet: $492.33
- Water: Public
- Construction: Block, Stucco
- Date Listed: 2026-10-31 00:00:00
- Pool: Y
- Pool Description: In Ground, Gunite, Heated, Lighting, Screen Enclosure
- Private Spa: Y
- Furnished: Unfurnished
- Windows: Window Treatments
- Parking: Driveway, Garage Door Opener
- Garage Description: Y
- Garage Spaces: 2
- Attached Garage: Y
- Flooring: Carpet, Travertine
- Roof: Tile
- Heating: Central, Electric, Zoned
- Cooling: Central Air, Zoned
- Fireplace: Y
- Security: Gated Community, Security Gate
- Laundry: Inside, Laundry Room
- 55+ Community: N
- Pets: Yes
- Sewer: Public Sewer
- Lot Desc.: Cul-De-Sac, Greenbelt, In County, Landscaped, Level, Paved, Private
- Parcel ID: 0142060015
- Amenities: Basketball Court, Clubhouse, Fence Restrictions, Fitness Center, Gated, Golf Course, Pickleball Court(S), Playground, Pool, Recreation Facilities, Tennis Court(S), Vehicle Restrictions
Listing Courtesy Of: Generous Property
mark@generousproperty.com
mark@generousproperty.com