186 Windward Drive, Osprey, FL 34229
For Sale $749,900
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Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2-bath residence offers a split bedroom layout, unique community amenities, NEW ROOF in 2022, and plenty of room for a private pool. As you enter the home, you will be greeted by the formal living room and dining room to the left and hallway to the family room, kitchen, and dinette straight ahead. The entire interior has been professionally painted in 2025, and there is tons of natural light that flows through the many windows of this home. The kitchen is open to the family room and dinette for easy entertaining. There is also a HUGE bonus room toward the back of the home. Next to the family room is entrance to the hallway leading to the two guest bedrooms and guest bathroom. On the opposite side of the home, past the dining room is the spacious primary suite with generous walk-in closet and ensuite bath. The laundry room is located near the family room. Entrance to the attached 2 car garage is near the foyer. Roof was replaced in 2022 & AC was installed in 2016. The entire house has also been replumbed! Southbay Yacht & Racquet Club is an active lifestyle community with many social, boating, and sports activities. The clubhouse has recently been renovated and features a community pool, fitness center, ballroom, two kitchens, card room, game room, and an elevator! Additional amenities include 3 tennis courts, 4 pickle ball courts, basketball, playground, bocce, shuffleboard, and miles of walking trails and green space. The community-owned marina—with residents-only boat slips—provides direct Intracoastal Waterway access with no fixed bridges to the Gulf. The community is welcoming and lively—perfect for families and those who enjoy an active, coastal lifestyle. This community is in the perfect location with several warm gulf beaches, Downtown Venice & Downtown Sarasota close by. The famous Casey Key Fish House and Tiki Bar are just a golf cart ride away! Oscar Scherer State Park is across Tamiami Trail and Pine View (#1 school in the state) is about 5 minutes away. This home is ready for you to start living the elevated Southbay lifestyle!
Cathedral Ceiling(s)
Ceiling Fans(s)
High Ceilings
Kitchen/Family Room Combo
Living Room/Dining Room Combo
Primary Bedroom Main Floor
Split Bedroom
Thermostat
Vaulted Ceiling(s)
Walk-In Closet(s)
Basketball Court
Clubhouse
Fitness Center
Park
Pickleball Court(s)
Playground
Pool
Tennis Court(s)
Taxes: $7.00
Tax Year: 2025
Association Fee: $613.00
Association Fee Frequency: Quarterly
Condo Fee Frequency: Quarterly
Lighting
Private Mailbox
Rain Gutters
Sliding Doors
Dishwasher
Dryer
Electric Water Heater
Microwave
Range
Refrigerator
Washer
Garden
Elementary School: Laurel Nokomis Elementary
Middle School: Sarasota Middle
Junior High: Sarasota Middle
High School: Venice Senior High
MLS Area: 34229 - Osprey
Price per Square Feet: $299.36
Total Floors: 1
Water: Public
Lot Desc.: Corner Lot, Landscaped, Paved
Construction: Block, Stucco
Date Listed: 2026-01-09 00:46:09
Pool: No
Private Spa: No
Furnished: Unfurnished
Parking: Deeded, Driveway, Garage Door Opener, Off Street
Garage Spaces: 2
Flooring: Wood
Roof: Tile
Heating: Central
Cooling: Central Air
Pets: Yes
Sewer: Public Sewer
Amenities: Basketball Court, Clubhouse, Fitness Center, Park, Pickleball Court(S), Playground, Pool, Tennis Court(S)
Listing Courtesy Of: Keller Williams On The Water S
brittanycoleman208@gmail.com
Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2-bath residence offers a split bedroom layout, unique community amenities, NEW ROOF in 2022, and plenty of room for a private pool. As you enter the home, you will be greeted by the formal living room and dining room to the left and hallway to the family room, kitchen, and dinette straight ahead. The entire interior has been professionally painted in 2025, and there is tons of natural light that flows through the many windows of this home. The kitchen is open to the family room and dinette for easy entertaining. There is also a HUGE bonus room toward the back of the home. Next to the family room is entrance to the hallway leading to the two guest bedrooms and guest bathroom. On the opposite side of the home, past the dining room is the spacious primary suite with generous walk-in closet and ensuite bath. The laundry room is located near the family room. Entrance to the attached 2 car garage is near the foyer. Roof was replaced in 2022 & AC was installed in 2016. The entire house has also been replumbed! Southbay Yacht & Racquet Club is an active lifestyle community with many social, boating, and sports activities. The clubhouse has recently been renovated and features a community pool, fitness center, ballroom, two kitchens, card room, game room, and an elevator! Additional amenities include 3 tennis courts, 4 pickle ball courts, basketball, playground, bocce, shuffleboard, and miles of walking trails and green space. The community-owned marina—with residents-only boat slips—provides direct Intracoastal Waterway access with no fixed bridges to the Gulf. The community is welcoming and lively—perfect for families and those who enjoy an active, coastal lifestyle. This community is in the perfect location with several warm gulf beaches, Downtown Venice & Downtown Sarasota close by. The famous Casey Key Fish House and Tiki Bar are just a golf cart ride away! Oscar Scherer State Park is across Tamiami Trail and Pine View (#1 school in the state) is about 5 minutes away. This home is ready for you to start living the elevated Southbay lifestyle!
Property Details
Price: $749,900
Sq Ft: 2,505
($299 per sqft)
Bedrooms: 3
Bathrooms: 2
City: Osprey
County: Sarasota
Type: Single Family Reside
Development: Southbay Yacht & Racquet Club
Acres: 0.30
Virtual Tour/Floorplan: View
Year Built: 1983
Listing Number: N6142087
Status Code: A-Active
Taxes: $7.00
Tax Year: 2025
Garage:
2
Furnishings: Unfurnished
Pets Allowed: Yes
Interior Features:
Cathedral Ceiling(s)
Ceiling Fans(s)
High Ceilings
Kitchen/Family Room Combo
Living Room/Dining Room Combo
Primary Bedroom Main Floor
Split Bedroom
Thermostat
Vaulted Ceiling(s)
Walk-In Closet(s)
Amenities:
Basketball Court
Clubhouse
Fitness Center
Park
Pickleball Court(s)
Playground
Pool
Tennis Court(s)
Financial Information:
Taxes: $7.00
Tax Year: 2025
Association Fee: $613.00
Association Fee Frequency: Quarterly
Condo Fee Frequency: Quarterly
Exterior Features:
Lighting
Private Mailbox
Rain Gutters
Sliding Doors
Equipment:
Dishwasher
Dryer
Electric Water Heater
Microwave
Range
Refrigerator
Washer
View:
Garden
School Information:
Elementary School: Laurel Nokomis Elementary
Middle School: Sarasota Middle
Junior High: Sarasota Middle
High School: Venice Senior High
Additional Information:
MLS Area: 34229 - Osprey
Price per Square Feet: $299.36
Total Floors: 1
Water: Public
Lot Desc.: Corner Lot, Landscaped, Paved
Construction: Block, Stucco
Date Listed: 2026-01-09 00:46:09
Pool: No
Private Spa: No
Furnished: Unfurnished
Parking: Deeded, Driveway, Garage Door Opener, Off Street
Garage Spaces: 2
Flooring: Wood
Roof: Tile
Heating: Central
Cooling: Central Air
Pets: Yes
Sewer: Public Sewer
Amenities: Basketball Court, Clubhouse, Fitness Center, Park, Pickleball Court(S), Playground, Pool, Tennis Court(S)
Map of 186 Windward Drive, Osprey, FL 34229
Listing Courtesy Of: Keller Williams On The Water S
brittanycoleman208@gmail.com