This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/96
$4,590,000
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/96
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.
Full Property Details
Full Property Details for 275 Lookout Point Dr
General
- Price: $4,590,000
- HOA FEE: $219/month
- HOA FEE FREQ.: Quarterly
- Taxes: $17,826 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: A4707430
- Updated: 10/1/2026
- Added to Site: 9 day(s) ago
Rental Information
- Min. Lease: 3 Months
Interior
- Number of Rooms: 11
- Interior Features: Built-in Features, Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Thermostat, Walk-In Closet(s)
- Fireplace: Yes
- Fireplace(s): Living Room
- Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer
- Furnishings: Unfurnished
- Flooring: Carpet, Ceramic Tile
Rooms
Bathrooms
- Total Bathrooms: 5
- Full Bathrooms: 5
Bedrooms
- Total Bedrooms: 5
Other Rooms
- Laundry: Inside, Laundry Room
Additional Information
- Shared Amenities: Basketball Court, Clubhouse, Fitness Center, Handicap Modified, Lobby Key Required, Park, Pickleball Court(s), Playground, Pool, Shuffleboard Court, Tennis Court(s), Wheelchair Access
- Pool: Yes
- Private Pool: Yes
- Pool Description: Heated, In Ground, Lighting
- Spa: Yes
- Spa Description: Heated, In Ground
Exterior
- Exterior Features: Balcony, French Doors, Hurricane Shutters, Lighting, Sliding Doors
- Deck/Patio: Rear Porch, Screened
- Porch/Patio/Deck: Rear Porch, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Covered Spaces: 3
- Parking Features: Driveway, Ground Level, Guest, Workshop in Garage
Location
- Area: 34229 - Osprey
- County: Sarasota
- Development Name: 34229 - Osprey
- Subdivision: SOUTHBAY YACHT & RACQUET CLUB
- Driving 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.
- Direction Faces: East
School Information
- Elementary School: Laurel Nokomis Elementary
- Middle School: Laurel Nokomis Middle
- High School: Venice Senior High
Community
- Community Name: 34229 - Osprey
- 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)
- Optional Amenities: Basketball Court, Clubhouse, Fitness Center, Handicap Modified, Lobby Key Required, Park, Pickleball Court
- Association: Yes
- Assoc. Name: Southbay Yacht & Racquet Club - Rachelle Freed
- Assoc. Fees Include: Community Pool
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Electric, Exhaust Fan, Propane
Utilities
- Sewer: Public Sewer
- Water: Private, Public
- Utility Description: BB/HS Internet Available, Cable TV Available, Cable Connected, Electricity Available, Electricity Connected, Fiber Optics, Propane, Sewer Available, Sewer Connected, Street Lights, Underground Utilities, Water A
Structural Information
- Builder: John Cannon
- Exterior Const.: Cement Siding, Stucco
- Roof: Concrete, Tile
- Stories/Levels: Two
- Square Feet: 5,279
- Sq. Ft. Source: Public Records
- Year Built: 2007
Lot Features
- Property View: Water
- Lot Size (Acres): 0.38
- Lot Size (Sq. Ft.): 16,709
- Lot Size: 16709
- Street/Road Desc.: Paved
Water Features
- Water Front: Yes
- Water View: Yes
- Water Access: Yes
- Water Access Desc: Intracoastal Waterway, Marina
- Water Extras: Yes
- Water Front Desc.: Intracoastal Waterway
Financial Considerations
- Association Fee: $656
- Assoc Fee Freq.: Quarterly
- Assoc Fee Desc.: Required
- Tax Amount: $17,826
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: LOT 301 SOUTHBAY YACHT & RACQUET CLUB
- Flood Zone Info: AE, X
- APN: 158070010
- Property ID: 158070010
Listed by Michael Saunders & Company
Get Pre-Approved Today
Schools
Schools serving 275 Lookout Point Dr
School District:Sarasota County School District
| Name | Grades | Distance |
|---|---|---|
Laurel Nokomis School 1900 Laurel Road East, Nokomis, FL 34275 | PK-8 | 4.5 mi |
Venice Senior High School 1 Indian Avenue, Venice, FL 34285 | 9-12 | 6.1 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 275 Lookout Point Dr
Date
Details
Price
Change
Source
10/01/2026
Listed
$4,590,000
253.08%
MLS
10/09/2003
Sold
$1,300,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 275 Lookout Point Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$17,826
7%
$1,479,275
3%
2024
$16,732
3%
$1,437,585
3%
2023
$16,311
2%
$1,395,714
3%
2022
$16,011
—
$1,355,062
3%
2021
$15,981
—
$1,315,594
1%
2021
$15,981
2%
$1,297,430
2%
2019
$15,652
2%
$1,268,260
2%
2018
$15,373
—
$1,244,612
2%
2017
$15,320
—
$1,219,013
2%
2016
$15,297
-2%
$1,193,940
1%
2015
$15,592
4%
$1,185,641
5%
2014
$14,962
—
$1,132,913
2%
2013
$14,967
—
$1,116,170
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 275 Lookout Point Dr
275 Lookout Point Drive, Osprey, FL 34229 (MLS# A4707430) is a Single Family property with 5 bedrooms and 5 full bathrooms. 275 Lookout Point Drive is currently listed for $4,590,000 and was received on October 01, 2026. Want to learn more about 275 Lookout Point Drive? Do you have questions about finding other Single Family real estate for sale in Osprey? You can browse all Osprey real estate or contact a Coldwell Banker agent to request more information.

