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186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo
186 Windward Drive, Osprey, FL 34229 Photo

93 Total Photos [Click to View All]

$599,900
Status: Active
186 Windward Drive Osprey, FL 34229
  • 3
    Bedrooms
  • 2
    Total Baths
  • 2,505
    Square Feet
  • 0.30
    Acres
  • 1983
    Year Built
  • 613/Quarterly
    HOA

Property Description

Price was dropped $50,000 on 5/7! Survey and pool quote are available! 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!**As of Jan 2026, there is marina space available immediately (no wait list) and fees range between $169-$705 per quarter depending on what size you require.This is subject to change.**This listing went pending in March. When the buyers couldn't secure their financing, it went back on market. No inspections have been done.**

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Property Features

MLS Number: N6142087
Days on Market: 124
Subdivision: SOUTHBAY YACHT & RACQUET CLUB
County: Sarasota
Bedrooms: 3
Total Square Feet: 2,505
New Constuction: No
Construction: Block,Stucco
Outdoor Features: Lighting, Private Mailbox, Rain Gutters, Sliding Doors
Waterfront: No
Property Type: Residential - Single Family
Cooling: Central Air
Garage: 2 car attached
Heating: Central
Lot Size: 0.30 Acres
Roof Type: Tile
Stories: 1.0
Taxes: $7,566
Year Built: 1983

Amenities

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)
Lighting
Private Mailbox
Rain Gutters
Sliding Doors

Feature Descriptions

Additional Rooms: Bonus Room, Family Room
Appliances: Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
Association Amenities: Basketball Court, Clubhouse, Fitness Center, Park, Pickleball Court(s), Playground, Pool, Tennis Court(s)
Community Features: Clubhouse, Deed Restrictions, Fitness Center, Golf Carts OK, Park, Playground, Pool, Sidewalks, Tennis Court(s)
Days on Site: 124
Directions: From 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
Exterior: Block, Stucco
Flood Zone Code: X
Flooring: Wood
Foundation: Slab
Garage Dimensions: 21x22
HOA Fee: 613/ Quarterly
HOA Y/N: Yes
Home Warranty Y/N: No
Listing Terms: Cash, Conventional, FHA, VA Loan
Lot: Corner Lot, Landscaped, Paved
Lot Dimensions: 0.3
Other Equipment: Irrigation Equipment
Ownership: Fee Simple
Parking: Deeded, Driveway, Garage Door Opener, Off Street
Parking Notes: Deeded, Driveway, Garage Door Opener, Off Street
Patio/Porch: Covered, Patio, Screened
Pets Allowed: Yes
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Sewer: Public Sewer
Showing Instructions: Appointment Only, Combination Lock Box, Go Direct, See Remarks, ShowingTime
Special Sale Provisions: None
Special View Info: Water
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: Public
Water Access: Intracoastal Waterway, Marina
Water Access Y/N: Yes
Zoning: RSF2

Room Sizes

Living Room: 21.5x14.1
Dining Room: 10.11x10.2
Kitchen: 12.9x11.9
Dinette: 11.8x12.1
Family Room: 13.8x11.11
Primary Bedroom: 11.6x21.11
Primary Bathroom: 11.6x7.4
Bedroom 1: 12.5x10.11
Bedroom 2: 11.8x12.1
Bathroom 2: 7.1x5.1
Bonus Room: 35.8x18.11

Location

Listed By / Shown By

Listed By

Broker Name: KELLER WILLIAMS ON THE WATER S
Broker Contact: 941-803-7522

Shown By

Broker Title: EstaVal
Broker Phone: 941-241-4100

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Estimated Payment

$ 2,140.59 per month $1,335.12 Principal & Interest $630.50 Property Tax $174.97 Homeowner's Insurance

Change Payment Information

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(Payments are an estimate and may vary by lender)

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