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.
Sold for $1,900,000
$1,900,000
340 Osprey Point Dr, Osprey, FL 34229
5beds
6,001sqft
Single Family Residence
Built in 1998
0.78 Acres Lot
$1,888,100 Zestimate®
$317/sqft
$7,900 Estimated rent
Home value
$1,888,100
$1.74M - $2.06M
$7,900/mo
Zestimate® history
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Zillow last checked: 7 hours ago
Listing updated: February 11, 2026 at 08:33am
Listing Provided by:
Lee Brewer 941-724-3448,
RE/MAX ALLIANCE GROUP 941-954-5454
Bought with:
Drew Russell, 3108183
MICHAEL SAUNDERS & COMPANY
Source: Stellar MLS,MLS#: A4647690
Originating MLS: Sarasota - Manatee
Originating MLS: Sarasota - Manatee
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 7
- Full bathrooms: 5
- 1/2 bathrooms: 2
Primary bedroom
- Description: Room8
- Features: Walk-In Closet(s)
- Level: First
- Area: 320 Square Feet
- Dimensions: 20x16
Bedroom 2
- Description: Room9
- Features: Walk-In Closet(s)
- Level: Second
- Area: 182 Square Feet
- Dimensions: 13x14
Bedroom 3
- Description: Room10
- Features: Walk-In Closet(s)
- Level: Second
- Area: 210 Square Feet
- Dimensions: 15x14
Bedroom 4
- Description: Room11
- Features: Walk-In Closet(s)
- Level: Second
- Area: 210 Square Feet
- Dimensions: 15x14
Bedroom 5
- Description: Room12
- Features: Walk-In Closet(s)
- Level: Second
- Area: 187 Square Feet
- Dimensions: 17x11
Dining room
- Description: Room5
- Level: First
- Area: 240 Square Feet
- Dimensions: 15x16
Family room
- Description: Room2
- Level: First
- Area: 484 Square Feet
- Dimensions: 22x22
Foyer
- Description: Room7
- Level: First
- Area: 150 Square Feet
- Dimensions: 15x10
Great room
- Description: Room3
- Level: Second
- Area: 480 Square Feet
- Dimensions: 24x20
Kitchen
- Description: Room1
- Level: First
- Area: 572 Square Feet
- Dimensions: 26x22
Living room
- Description: Room4
- Level: First
- Area: 320 Square Feet
- Dimensions: 20x16
Office
- Description: Room6
- Level: First
- Area: 180 Square Feet
- Dimensions: 15x12
Heating
- Central, Electric, Exhaust Fan
Cooling
- Central Air, Zoned
Appliances
- Included: Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer
- Laundry: Inside, Laundry Room
Features
- Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Coffered Ceiling(s), Crown Molding, Dry Bar, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
- Flooring: Carpet, Ceramic Tile, Marble, Hardwood
- Doors: Outdoor Shower, Sliding Doors
- Windows: Hurricane Shutters, Hurricane Shutters/Windows
- Has fireplace: Yes
- Fireplace features: Gas, Living Room
Interior area
- Total structure area: 7,306
- Total interior livable area: 6,001 sqft
Property
Parking
- Total spaces: 3
- Parking features: Garage - Attached
- Attached garage spaces: 3
Features
- Levels: One
- Stories: 1
- Exterior features: Irrigation System, Outdoor Shower
- Has private pool: Yes
- Pool features: Auto Cleaner, Child Safety Fence, Deck, Gunite, In Ground, Screen Enclosure
- Spa features: Heated, In Ground
- Has view: Yes
- View description: Trees/Woods, Creek/Stream
- Has water view: Yes
- Water view: Creek/Stream
- Waterfront features: Waterfront, Creek, Creek Access, Bridges - No Fixed Bridges
- Body of water: NORTH CREEK
Lot
- Size: 0.78 Acres
- Features: Cleared, Oversized Lot
Details
- Parcel number: 0142030009
- Zoning: RE1
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Custom
- Property subtype: Single Family Residence
Materials
- Block
- Foundation: Slab
- Roof: Tile
Condition
- New construction: No
- Year built: 1998
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: BB/HS Internet Available, Cable Connected, Electricity Connected, Public, Street Lights, Underground Utilities
Community & neighborhood
Security
- Security features: Gated Community, Security Gate, Security System
Community
- Community features: Water Access, Waterfront, Buyer Approval Required, Deed Restrictions, Fitness Center, Golf, No Truck/RV/Motorcycle Parking, Pool, Special Community Restrictions, Tennis Court(s)
Location
- Region: Osprey
- Subdivision: OAKS
HOA & financial
HOA
- Has HOA: Yes
- HOA fee: $158 monthly
- Services included: 24-Hour Guard, Reserve Fund, Fidelity Bond, Private Road
- Association name: LIGHTHOUSE PROPERTY MGT. / HOPE ROOT
- Association phone: 941-460-5560
Other fees
- Pet fee: $0 monthly
Other financial information
- Total actual rent: 0
Other
Other facts
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
- Road surface type: Paved, Asphalt
Price history
| Date | Event | Price |
|---|---|---|
| 2/10/2026 | Sold | $1,900,000-20.7%$317/sqft |
Source:  Stellar MLS #A4647690 Report a problem | ||
| 1/4/2026 | Pending sale | $2,395,000$399/sqft |
Source: Stellar MLS #A4647690 Report a problem | ||
| 11/10/2025 | Price change | $2,395,000-4.2%$399/sqft |
Source: Stellar MLS #A4647690 Report a problem | ||
| 4/5/2025 | Listed for sale | $2,500,000+13.6%$417/sqft |
Source: Stellar MLS #A4647690 Report a problem | ||
| 1/1/2024 | Sold | $2,200,000-11.8%$367/sqft |
Source: Stellar MLS #A4579561 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $21,153 -4.6% | $1,730,300 -5.1% |
| 2024 | $22,178 +4.1% | $1,822,900 +2.3% |
| 2023 | $21,297 +15.6% | $1,782,332 +50.7% |
Find assessor info on the county website
Neighborhood: 34229
Nearby schools
GreatSchools rating
- 8/10Laurel Nokomis SchoolGrades: PK-8Distance: 6.5 mi
- 6/10Venice Senior High SchoolGrades: 9-12Distance: 8.6 mi
Schools provided by the listing agent
- Elementary: Laurel Nokomis Elementary
- Middle: Laurel Nokomis Middle
- High: Venice Senior High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$1,888,100
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$1,888,100
- Florida
- Sarasota County
- Osprey
- 34229
- 340 Osprey Point Dr