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Property for sale at 340 OSPREY POINT DR, OSPREY, FL, 34229

340 Osprey Point DrOsprey, FL, 34229

5beds
7baths
6,001sqft
Single Family Residence
Built in 1998
$475 Quarterly HOA Fee
$1,900,000
Sold
Price per sqft
$317
Sold on
Feb 10, 2026
MLS #A4647690Updated Feb 11, 2026

About this property

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.

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Property details

Property type
Single Family Residence
Street address
340 Osprey Point Dr
City
Osprey
State
FL
ZIP code
34229
Year built
1998
New construction
No
Faces
Southwest
Rooms
12
Living area
6,001 sqft
Total building area
7,306 sqft
Levels
One

Stellar MLSThe data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.Stellar (MFR) data last updated at November 7, 2026 at 3:30 PM EST

Price & sale history

EventPrice
SoldMLS #A4647690$1,900,000
Price reducedMLS #A4647690$2,395,000Change: −4.2%−$105,000
Listed for saleMLS #A4647690$2,500,000
SoldMLS #A4579561$2,200,000
History may be incomplete.
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Location

Property for sale at 340 OSPREY POINT DR, OSPREY, FL, 34229
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