186 WINDWARD DRIVE, Osprey, FL, 34229 | $649,500

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. **

Features

  • Amenities: Basketball Court, Clubhouse, Fitness Center, Park, Pickleball Court(s), Playground, Pool, Tennis Court(s)
  • Rooms: 11
  • Bedrooms: 3
  • Baths: 2 full
  • Laundry: Inside, Laundry Room
  • Year Built: 1983
  • Garage: 2-car Deeded, Driveway, Garage Door Opener, Off Street
  • Heating: Central
  • Cooling: Central Air
  • Approx Sq. Feet: 2,505
  • Acreage: 0.3
  • Est. Taxes: $7,566
  • HOA Fee: $613 Quarterly
  • Lot Desc: Corner Lot, Landscaped
  • View: Garden
  • Elem. School: Laurel Nokomis Elementary
  • Middle School: Sarasota Middle
  • High School: Venice Senior High
  • Pet Policy: Yes
  • Appliances: Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
  • MLS#: N6142087
  • Days on Market: 57 days
  • Website: https://www.raveis.com
    /prop/N6142087/186windwarddrive_osprey_fl?source=qrflyer
This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of MFRMLS (My Florida Regional MLS DBA Stellar MLS). The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. (last updated 3/7/2026 8:02:21 AM)
Listing courtesy of KELLER WILLIAMS ON THE WATER S   Phone: 941-803-7522

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NMLS Mortgage Loan Originator ID 16953

917.838.7300

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186 WINDWARD DRIVE, Osprey, FL, 34229

$649,500

Customer Service

William Raveis Real Estate

Phone: 888.699.8876

Contact@raveis.com

Melissa Cohn

RVP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 917.838.7300

Melissa.Cohn@raveis.com

NMLS Mortgage Loan Originator ID 16953

5/6 (30 Yr)
Adjustable Rate Conforming*
30 Year
Fixed-Rate Conforming
15 Year
Fixed-Rate Conforming
Loan Amount $519,600 $519,600 $519,600
Term 360 months 360 months 180 months
Initial Interest Rate** 5.625% 6.125% 5.375%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.258% 6.292% 5.628%
Monthly Tax Payment $631 $631 $631
H/O Insurance Payment $92 $92 $92
Initial Principal & Interest Pmt $2,991 $3,157 $4,211
Total Monthly Payment $3,713 $3,879 $4,933

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.  The Total Monthly Payment does not include the estimated HOA/Common Charge payment.