OSPREY, FL 34229 186 WINDWARD DRIVE

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Presented By: KELLER WILLIAMS ON THE WATER S with 941-803-7522. - 941-803-7522
  • MLS# N6142087
  • 01/06/2026
  • Request Tour
  • Request Info
Disclaimer: The information contained in this listing has not been verified by Homepride Group at EXP Realty and should be verified by the buyer.
  • Beds • 3
  • Baths • 2
  • SQFT • 2,505
  • Garage • 2

Home Details

Price was reduced over $100,000!!! Went pending immediately and then the buyers couldn't secure financing. It is now BACK ON MARKET as of 3/19 and NO INSPECTIONS HAVE BEEN DONE! 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.**
Presented By: KELLER WILLIAMS ON THE WATER S with 941-803-7522. - 941-803-7522

Interior Features for 186 WINDWARD DRIVE

Bedrooms

Total Bedrooms3

Bathrooms

Half Baths0
Total Baths2

Other Interior Features

LivingAreaSourcePublic Records
Air Conditioning Y/NYes
Fireplace Y/NNo
FlooringHardwood
Furnished Y/NUnfurnished
Heating Y/NYes
Interior AmenitiesCathedral Ceiling(s), Ceiling Fan(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)
Laundry FeaturesInside, Laundry Room
Total Stories1

General for 186 WINDWARD DRIVE

Additional Parcels Y/NNo
Additional RoomsBonus Room, Family Room
AppliancesDishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
Assoc Fee Paid PerQuarterly
Association AmenitiesBasketball Court, Clubhouse, Fitness Center, Park, Pickleball Court(s), Playground, Pool, Tennis Court(s)
Association Fee IncludesCommon Area Taxes, Community Pool, Escrow Reserves Fund, Fidelity Bond, Manager, Pool Maintenance
Association NameJudy Brown
Attached Garage Yes
Building Area UnitsSquare Feet
Carport Y/NNo
CityOSPREY
Community FeaturesBoat Slip, Dock, Intracoastal Waterway, Marina, Clubhouse, Deed Restrictions, Fitness Center, Golf Carts OK, Park, Playground, Pool, Sidewalks, Tennis Court(s)
Construction MaterialsBlock, Stucco
CoolingCentral Air
CountySarasota
DirectionsFrom the intersection at US 41 and Laurel Rd take US 41 north. Turn left on Southbay Dr. Turn right on Windward Dr. Property will be on your left. From the intersection at US 41 and Blackburn Point Rd take Blackburn Point Rd west. Turn left on Southbay Dr. Turn left on Windward Dr. Property will be on your left.
Elementary SchoolLaurel Nokomis Elementary
Facing DirectionSouth
Flood Zone CodeX
Flood Zone Code XY
Full Baths2
Garage Spaces2
Garage Y/NYes
HOA Fee$613
HeatingCentral
High SchoolVenice Senior High
Land Lease Y/NNo
Lease Considered Y/NYes
Legal DescriptionLOT 136 SOUTHBAY YACHT & RACQUET CLUB
LevelsOne
Listing TermsCash, Conventional, FHA, VA Loan
Living Area UnitsSquare Feet
Lot Size Square Feet13130
Lot Size UnitsSquare Feet
MLS Area34229 - Osprey
Middle/Junior High SchoolSarasota Middle
Minimum Lease3 Months
Monthly HOA Amount204.33
New ConstructionNo
Occupancy TypeVacant
OwnershipFee Simple
Patio/Porch FeaturesCovered, Patio, Screened
Pets AllowedYes
Property SubtypeSingle Family Residence
Property TypeResidential
RoofTile
STELLAR_InLawSuiteYNNo
Senior Community Y/NNo
SewerPublic Sewer
Standard StatusActive
StatusActive
Subdivision NameSOUTHBAY YACHT & RACQUET CLUB
Tax Annual Amount7566.37
Tax Lot136
Tax Year2025
Total Rooms11
UtilitiesBB/HS Internet Available, Cable Available, Cable Connected, Electricity Available, Electricity Connected, Sewer Available, Sewer Connected, Water Available, Water Connected
ViewGarden
Virtual TourClick here
Virtual TourClick here
Water Access TypeIntracoastal Waterway, Marina
Water Access Y/NYes
Water View Y/NNo
Year Built1983
ZoningRSF2

Exterior for 186 WINDWARD DRIVE

Building Area Total3298
Covered Spaces2
Exterior AmenitiesIrrigation System, Lighting, Private Mailbox, Rain Gutters, Sliding Doors
Foundation DetailsSlab
Lot FeaturesCorner Lot, Landscaped
Lot Size Acres0.3
Lot Size Area13130
Parking FeaturesDeeded, Driveway, Garage Door Opener, Off Street
Private PoolNo
Road Frontage TypeStreet Paved
Road Surface TypePaved, Asphalt
SpaNo
VegetationTrees/Landscaped
Water SourcePublic
Waterfront Y/NNo

Additional Details

Price History

Steven Pugh

Broker Associate | Team Leader
Price $649,500
MLS#N6142087
List Date 01/06/2026
Property Type Single Family
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