340 Osprey Point Dr, OSPREY, FL 34229
Local realty services provided by:Better Homes and Gardens Real Estate Thomas Group



340 Osprey Point Dr,OSPREY, FL 34229
$2,500,000
- 5 Beds
- 7 Baths
- 6,001 sq. ft.
- Single family
- Active
Listed by:lee brewer
Office:re/max alliance group
MLS#:A4647690
Source:MFRMLS
Price summary
- Price:$2,500,000
- Price per sq. ft.:$342.18
- Monthly HOA dues:$158.33
About this home
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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Home facts
- Year built:1998
- Listing Id #:A4647690
- Added:131 day(s) ago
- Updated:August 14, 2025 at 12:11 PM
Rooms and interior
- Bedrooms:5
- Total bathrooms:7
- Full bathrooms:5
- Half bathrooms:2
- Living area:6,001 sq. ft.
Heating and cooling
- Cooling:Central Air, Zoned
- Heating:Central, Electric, Exhaust Fan
Structure and exterior
- Roof:Tile
- Year built:1998
- Building area:6,001 sq. ft.
- Lot area:0.78 Acres
Schools
- High school:Venice Senior High
- Middle school:Laurel Nokomis Middle
- Elementary school:Laurel Nokomis Elementary
Utilities
- Water:Public
- Sewer:Public, Public Sewer
Finances and disclosures
- Price:$2,500,000
- Price per sq. ft.:$342.18
- Tax amount:$21,513 (2024)
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