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About 340 OSPREY POINT DR, Osprey, Florida, 34229
Introducing The Grand Estate at The Oaks Bayside—a true masterpiece of refined living within one of Sarasota’s most prestigious gated communities. Surrounded by majestic oak trees and lush tropical landscaping, this extraordinary residence offers the perfect blend of elegance, comfort, and privacy. A brand-new roof (2024) crowns this sprawling estate, while a pavered circular driveway leads to a spacious 3-car side-load garage. Stately columns welcome you to the grand double-door entry, where you’ll step inside to find gleaming marble floors, soaring ceilings, and plantation shutters that set the stage for timeless sophistication. The thoughtfully designed floor plan includes a private office with built-ins and French doors, and a flexible open space with a dramatic backlit tray ceiling—ideal for a formal dining room, music room, or library. The formal living room features a stunning picture window that brings the outdoors in, along with a cozy fireplace and direct access to the luxurious pool area. The chef’s kitchen is a true showstopper, complete with an aquarium window breakfast nook, expansive breakfast bar, dual sinks, center island, double wall ovens, and a butler’s pantry. It opens seamlessly into the family room, where sliding glass doors, a wood-burning fireplace, wet bar, and built-in desk create a warm and inviting space for everyday living and entertaining. The primary suite is a tranquil retreat with a sunlit sitting area, private access to the pool, and a spa-inspired en suite bath with a walk-in shower and soaking tub that overlook your private tropical paradise. Step outside to your own resort-style oasis, where a sparkling pool, separate spa, travertine deck, and covered patio offer the ultimate in outdoor living. With over 6,000 square feet of living space, this estate features 5 bedrooms, 5 full bathrooms, and 2 half baths, along with two newer A/C systems (2023). As a resident of The Oaks, you’ll have access to The Oaks Club’s world-class amenities, including two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center, and fine dining. Ideally located near top-rated Pine View School, Historic Spanish Point, Casey Key, and Oscar Scherer State Park, this home offers both tranquility and convenience. Don’t miss your chance to own this exceptional estate—schedule your private tour today and experience the luxury of life at The Oaks Bayside.
Utilities : BB/HS Internet Available
Water Access : 1
Sewer : Public Sewer
Garage On Property : Yes.
Garage Spaces: 3
Exterior Features : Hurricane Shutters
Road Surface Type : Asphalt
Roof : Tile
Zoning : RE1
Heating : Central
Cooling : Central Air
Construction Materials : Block
Interior Features : Built-in Features
Fireplace Features : Gas
Laundry Features : Inside
Appliances : Built-In Oven
Flooring : Carpet
Utilities : BB/HS Internet Available
Water Access : 1
Sewer : Public Sewer
Garage On Property : Yes.
Garage Spaces: 3
Exterior Features : Hurricane Shutters
Road Surface Type : Asphalt
Roof : Tile
Zoning : RE1
Heating : Central
Cooling : Central Air
Construction Materials : Block
Interior Features : Built-in Features
Fireplace Features : Gas
Laundry Features : Inside
Appliances : Built-In Oven
Flooring : Carpet

Street Address: 340 OSPREY POINT DR
City: Osprey
State: Florida
Postal Code: 34229
County: Sarasota
Directions: Take Tamiami Trail south to Osprey, continue south to the Oaks Club on the right hand side of the road, Turn right at Osprey Point Road, stop at guard house proceed to the first street turn right, follow past the first stop sign to the house on the right side.

Property Information :
Listing Status: Active
Size: 6,001 Sqft
Lot Size: 0.78 Acres
MLS #: A4647690
Bedrooms: 5 bd
Bathrooms: 6 ba
Price: $2,395,000
Tax Amount: 21512.93
Construction Status: Built in 1998
Last Modified : Dec 13 2025 2:11AM
Amenities :
Fireplace

Courtesy of: Lee Brewer, RE/MAX ALLIANCE GROUP (MLS# 281518938)
Source MLS: StellarMLS