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186 Windward Drive, Osprey, FL

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$749,900

($299/sqft)

List Status: Active
186 Windward Drive
Osprey, FL 34229


3 beds
2 baths
2505 living sqft
Top Features
  • View: Garden
  • Subdivision: Southbay Yacht & Racquet Club
  • Built in  1983
  • Single Family Residence
Description
Property Details
Additional Information
Additional Lease Restrictions
Please see HOA docs for more information
Additional Parcels YN
false
Additional Rooms
Bonus Room, Family Room
Alternate Key Folio Num
0157070011
Appliances
Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
Approval Process
Please see HOA docs for more information
Association Amenities
Basketball Court, Clubhouse, Fitness Center, Park, Pickleball Court(s), Playground, Pool, Tennis Court(s)
Association Email
judybrown@sbyrc.net
Association Fee
613
Association Fee Frequency
Quarterly
Association Fee Includes
Common Area Taxes, Pool, Escrow Reserves Fund, Fidelity Bond, Management
Association Fee Requirement
Required
Association YN
true
Attached Garage YN
true
Available For Lease YN
1
Bathrooms Total Integer
2
Building Area Source
Public Records
Building Area Total
3298
Building Area Total Srch SqM
306.39
Building Area Units
Square Feet
Calculated List Price By Calculated SqFt
299.36
Carport YN
false
Community Features
Clubhouse, Deed Restrictions, Fitness Center, Golf Carts OK, Park, Playground, Pool, Sidewalks, Tennis Court(s)
Construction Materials
Block, Stucco
Cooling
Central Air
Country
US
Cumulative Days On Market
8
Current Price
749900.00
Direction Faces
South
Elementary School
Laurel Nokomis Elementary
Exterior Features
Lighting, Private Mailbox, Rain Gutters, Sliding Doors
Fireplace YN
false
Flood Zone Code
X
Flooring
Wood
Foundation Details
Slab
Furnished
Unfurnished
Garage Dimensions
21x22
Garage Spaces
2
Garage YN
true
Heating
Central
High School
Venice Senior High
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)
Internet Address Display YN
true
Internet Automated Valuation Display YN
false
Internet Consumer Comment YN
false
Internet Entire Listing Display YN
true
Laundry Features
Inside, Laundry Room
Lease Restrictions YN
1
Levels
One
List AOR
Sarasota - Manatee
Living Area Meters
232.72
Living Area Source
Public Records
Living Area Units
Square Feet
Lot Features
Corner Lot, Landscaped, Paved
Lot Size Acres
0.3
Lot Size Square Feet
13130
Lot Size Square Meters
1220
Middle Or Junior School
Sarasota Middle
Minimum Lease
3 Months
Modification Timestamp
2026-01-16T22:44:11.005Z
Monthly HOA Amount
204.33
New Construction YN
false
Num Of Own Years Prior To Lease
2
Num Times per Year
2
Occupant Type
Vacant
Other Equipment
Irrigation Equipment
Ownership
Fee Simple
Parcel Number
0157070011
Patio And Porch Features
Covered, Patio, Screened
Pets Allowed
Yes
Pool Private YN
false
Postal Code Plus 4
9751
Property Description
Walk-Up
Public Remarks
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! **The street behind this house (Blackburn Point Rd.) is a fairly quiet two lane Rd. That's the road you can take your golf cart to Casey Key Fish House & Tiki Bar!**There is marina space available and fees range between $169-$705 per quarter.**
Public Survey Range
18E
Public Survey Section
15
RATIO Current Price By Calculated SqFt
299.36
Road Surface Type
Asphalt
Roof
Tile
Room Count
11
SW Subdiv Community Name
Southbay Yacht & Racquet Club
Senior Community YN
false
Sewer
Public Sewer
Showing Requirements
Appointment Only, Combination Lock Box, Go Direct, See Remarks, ShowingTime
Spa YN
false
Status Change Timestamp
2026-01-09T00:46:09.000Z
Stories Total
1
Tax Annual Amount
7566.37
Tax Book Number
22-27
Tax Legal Description
LOT 136 SOUTHBAY YACHT & RACQUET CLUB
Tax Lot
136
Tax Year
2025
Total Acreage
1/4 to less than 1/2
Total Annual Fees
2452.00
Total Monthly Fees
204.33
Township
38S
Universal Property Id
US-12115-N-0157070011-R-N
Unparsed Address
186 WINDWARD DR
Utilities
BB/HS Internet Available, Cable Available, Cable Connected, Electricity Available, Electricity Connected, Sewer Available, Sewer Connected, Water Available, Water Connected
Vegetation
Trees/Landscaped
Water Access
Intracoastal Waterway, Marina
Water Access YN
1
Water Source
Public
Waterfront YN
false
Years Of Owner Prior To Leasing Req YN
1
Zoning
RSF2
Neighborhood Map
Popup

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MLS #MFRN6142087 Listing courtesy of Keller Williams On The Water S provided by Stellar MLS.

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All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independent verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. The source of the listing data is as follows: Stellar MLS (updated 1/27/26 2:33 PM) |

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