275 Lookout Point Drive, Osprey, FL, 34229

Waterfront - Primary on Main

Address

275 Lookout Point Drive, OSPREY, FL

Listing Type

Active

Price

$ 4,590,000

Your Agent

Rick Blaquiere

Property Manager/Realtor®

239-970-6831

Property Attributes

MLS#A4707430
TypeSingle Family
Listing Status Active
CountySarasota
CityOSPREY
AreaOsprey
NeighborhoodSOUTHBAY YACHT & RACQUET CLUB
Zip34229
StyleSingle Family Residence
Year Built2007
Taxes$ 17826
Price$ 4,590,000
Bedrooms5
Full Bathrooms5
Half Bathrooms0
Sqr Footage5279
Lot Size0.38 Acres

Data Source:

Stellar MLS

Property Description

Experience exceptional waterfront living in Southbay Yacht & Racquet Club at this expansive custom John Cannon residence offering more than 5,200 square feet, 5 bedrooms, 5 baths and sweeping panoramic water views from both levels. Set along more than 135 feet of waterfront, the home was thoughtfully designed to embrace its remarkable setting, with soaring ceilings, generous expanses of glass and beautifully proportioned indoor and outdoor living spaces overlooking the bay and Intracoastal Waterway. A completely reimagined front drive and all-new landscaping create a striking first impression and a fresh, refined coastal presence. Beyond the grand double-door entry, the home immediately opens to dramatic water views, drawing the eye through the interior and out toward the horizon. Ceilings rising to approximately 21 feet enhance the sense of scale, while a series of inviting living and entertaining spaces allow the home to feel equally suited for intimate evenings or larger gatherings. The kitchen serves as the heart of the residence, anchored by a substantial granite island and complemented by a gas cooktop with pot filler, while views stretch beyond the pool to the water. A full bar and dedicated wine room enhance the main level, with an additional wet bar upstairs for effortless entertaining throughout the home. Privately positioned on the main level, the primary suite is a serene waterfront retreat with a sitting area, two generous closets and an expansive bath. Additional downstairs bedrooms are thoughtfully located on the opposite side of the residence, creating privacy and separation for family and guests. Upstairs, either an office or a fifth bedroom offers an elevated and inspiring setting for work or quiet retreat, with access to the upper terrace and its sweeping water views. From both floors, the landscape of water and sky becomes part of the experience of the home. Outdoor living is equally memorable. A heated pool and spa, covered and screened entertaining areas, outdoor kitchen, fireplace, expansive terraces and private dock create a seamless connection between the residence and the waterfront. Mornings begin with peaceful views across the water, afternoons unfold poolside, and evenings are defined by the colors of sunset. Southbay Yacht & Racquet Club offers one of the area's most distinctive boating lifestyles. Its community-owned deep-water marina accommodates vessels up to 55 feet, allowing residents to walk or take a golf cart from home to their boat. Community amenities include a renovated clubhouse, geothermal pool, fitness center overlooking the marina, tennis and pickleball courts, bocce, shuffleboard, basketball, kayak storage, a waterfront park, approximately 20 acres of common grounds and miles of walking trails. Perfectly positioned between Sarasota and Venice and convenient to Siesta Key, Nokomis Beach, the Legacy Trail, Pine View School, waterfront dining, shopping and Oscar Scherer State Park, 275 Lookout Point is a compelling blend of scale, setting and lifestyle—a substantial waterfront residence with panoramic views, private outdoor living and direct access to the heart of Southbay’s boating community.

Elementary School	Middle School	High School
Laurel Nokomis Elementary Elementary School	Laurel Nokomis Middle Middle School	Venice Senior High High School

Price History
10/1/2026	Listed $4,590,000

General Features

Sewer	Public Sewer
Heating	Central,Electric,Exhaust Fan,Propane
Cooling	Central Air
Utilities	BB/HS Internet Available,Cable Available,Cable Connected,Electricity Available,Electricity Connected,Fiber Optics,Propane,Sewer Available,Sewer Connected,Street Lights,Underground Utilities,Water Available,Water Connected
Roof	Concrete,Tile
Appliances	Built-In Oven,Cooktop,Dishwasher,Disposal,Dryer,Microwave,Refrigerator,Washer
Zoning	RSF2
HOA Fee	656
Garage Spaces	3
Association Fee Includes	Community Pool
Patio/Porch Features	Rear Porch,Screened
Pool Features	Heated,In Ground,Lighting
Construction Materials	Cement Siding,Stucco
Pets Allowed	Yes
Year Built	2007
View	Water
Levels	Two
Property Subtype	Single Family Residence
Tax Year	2025
Ownership	Fee Simple
Waterfront Features	Intracoastal Waterway
Community Features	Dock,Fishing,Intracoastal Waterway,Marina,Clubhouse,Dog Park,Fitness Center,Golf Carts OK,Handicap Modified,No Truck/RV/Motorcycle Parking,Park,Playground,Pool,Sidewalks,Tennis Court(s)
Assoc Fee Paid Per	Quarterly
County	Sarasota
New Construction	false
Property Type	Residential
Association Amenities	Basketball Court,Clubhouse,Fitness Center,Handicap Modified,Lobby Key Required,Park,Pickleball Court(s),Playground,Pool,Shuffleboard Court,Tennis Court(s),Wheelchair Access
Attached Garage	true
Subdivision Name	SOUTHBAY YACHT & RACQUET CLUB
Facing Direction	East
Garage Y/N	true
Total Rooms	11
Full Baths	5
Status	Active
Directions	Take 41 to Blackburn Point Road. Southbay Yacht & Raquet Club will be on your left, go straight through first stop sign, take a right on Harbor House Drive, take a left onto Lookout Point Drive and it will be on your right.
High School	Venice Senior High
City	OSPREY
Association Name	Southbay Yacht & Racquet Club - Rachelle Freed
Senior Community Y/N	false
MLS Area	34229 - Osprey
Lot Size Units	Square Feet
Lot Size Square Feet	16709
Carport Y/N	false
Spa Features	Heated,In Ground
Elementary School	Laurel Nokomis Elementary
Land Lease Y/N	false
Tax Annual Amount	17826
Middle/Junior High School	Laurel Nokomis Middle
Property Condition	Completed
Additional Parcels Y/N	false
Lease Considered Y/N	true
Virtual Tour	https://pix360.com/phototour3/42064/
Building Area Units	Square Feet
Living Area Units	Square Feet
Builder Name	John Cannon
Standard Status	Active
Occupancy Type	Vacant
Tax Lot	301
Legal Description	LOT 301 SOUTHBAY YACHT & RACQUET CLUB
Water View	Intracoastal Waterway
Water Access Type	Intracoastal Waterway,Marina
Minimum Lease	3 Months
Water Access Y/N	true
Monthly HOA Amount	218.67
Additional Rooms	Bonus Room,Den/Library/Office,Family Room
Water View Y/N	true
Flood Zone Code	AE, X
In Law Suite YN	false
Flood Zone Code X	Yes

Interior Features

Interior Amenities	Built-in Features,Ceiling Fan(s),Crown Molding,Eating Space In Kitchen,High Ceilings,Kitchen/Family Room Combo,Living Room/Dining Room Combo,Primary Bedroom Main Floor,Thermostat,Walk-In Closet(s)
Flooring	Carpet,Ceramic Tile
Furnished Y/N	Unfurnished
Fireplace Features	Living Room
Total Stories	2
Air Conditioning Y/N	true
Heating Y/N	true
Fireplace Y/N	true
Laundry Features	Inside,Laundry Room
Total Bedrooms	5
LivingAreaSource	Public Records
Total Baths	5

Exterior Features

Exterior Amenities	Balcony,French Doors,Hurricane Shutters,Lighting,Sliding Doors
Vegetation	Trees/Landscaped
Parking Features	Driveway,Ground Level,Guest,Workshop in Garage
Lot Features	Landscaped,Near Marina
Water Source	Private,Public
Lot Size Area	16709
Foundation Details	Slab,Stem Wall
Spa	true
Building Area Total	7781
Lot Size Acres	0.38
Road Surface Type	Paved
Private Pool	true
Waterfront Y/N	true
Covered Spaces	3