Back 340 Osprey Point Dr
Off Market

340 Osprey Point Dr

Osprey FL 34229

5
7
3
7306 sq. ft.
34125 sq. ft.
Single-Family
Last sold for $1,900,000
Lee BrewerLee Brewer, last sold this property on 10 February 2026 after 308 days on market.

Overview

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.

Features

5 bedrooms
7 bathrooms
3 carspaces
3 garage spaces
7306 sq. ft. floor area
34125 sq. ft. lot size
Single-Family

Estimated Value

Based on this property and similar 5 bedroom single-family properties sold in Osprey over the last 12 months, the estimated median property value of 340 Osprey Point Dr is $1.6m.

Median value
$1.6m
Estimated value range
$620k - $3.52m
Median days on market
129
Estimated value trend
-14%
decrease over the last 12 months
Average days on market is based on recent, comparable sales in Osprey. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 340 Osprey Point Dr

2026
Sold
$1,900,000
10 Feb 2026 by Lee Brewer, of RE/MAX ALLIANCE GROUP
2024
Sold
$2,200,000
01 Jan 2024 by Lee Brewer, of RE/MAX ALLIANCE GROUP
2022
Sold
$2,280,000
24 May 2022 by Steve Abbe

Happy sellers in Osprey

<50%
Less than 50% of sellers in Osprey reported that their sale price either exceeded or met their price expectations.

Osprey stands out as a desirable suburb for sellers, consistently delivering great customer service and strong market results for homeowners.

This is based on voluntary sentiment collected from 11 reviews in Osprey over the last 12 months.

Local market activity for 5 bedroom single-family properties in Osprey

In the last 12 months, 7 five-bedroom single-family properties similar to 340 Osprey Point Dr, have been sold.

This represents a 20% increase in five-bedroom single-family properties sales when compared to the previous 12 months.

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