Call Now:

Broker IDX Billing System

Broker,REALTOR ®,e-PRO
Broker IDX Sites Inc.
A Winning Team
  1. Home
  2. Property Search
  3. Search results
  4. 186 Windward Drive, OSPREY, FL 34229
Contact Broker IDX Sites Inc.
Contacting Broker IDX Sites Inc.
  • All fields are required.
Schedule A Showing
Schedule a Showing.
  • All fields are required.
Check this box to Register with us:
Submit an Offer Now!
Submit an Offer Now!
All fields are required.
Print Flyer
Active
Property Photos
186 Windward Drive
  1. Image 1 of 93 For 186 Windward Drive
  2. Image 2 of 93 For 186 Windward Drive
  3. Image 3 of 93 For 186 Windward Drive
  4. Image 4 of 93 For 186 Windward Drive
  5. Image 5 of 93 For 186 Windward Drive
  6. Image 6 of 93 For 186 Windward Drive
  7. Image 7 of 93 For 186 Windward Drive
  8. Image 8 of 93 For 186 Windward Drive
  9. Image 9 of 93 For 186 Windward Drive
  10. Image 10 of 93 For 186 Windward Drive
  11. Image 11 of 93 For 186 Windward Drive
  12. Image 12 of 93 For 186 Windward Drive
  13. Image 13 of 93 For 186 Windward Drive
  14. Image 14 of 93 For 186 Windward Drive
  15. Image 15 of 93 For 186 Windward Drive
  16. Image 16 of 93 For 186 Windward Drive
  17. Image 17 of 93 For 186 Windward Drive
  18. Image 18 of 93 For 186 Windward Drive
  19. Image 19 of 93 For 186 Windward Drive
  20. Image 20 of 93 For 186 Windward Drive
  21. Image 21 of 93 For 186 Windward Drive
  22. Image 22 of 93 For 186 Windward Drive
  23. Image 23 of 93 For 186 Windward Drive
  24. Image 24 of 93 For 186 Windward Drive
  25. Image 25 of 93 For 186 Windward Drive
  26. Image 26 of 93 For 186 Windward Drive
  27. Image 27 of 93 For 186 Windward Drive
  28. Image 28 of 93 For 186 Windward Drive
  29. Image 29 of 93 For 186 Windward Drive
  30. Image 30 of 93 For 186 Windward Drive
  31. Image 31 of 93 For 186 Windward Drive
  32. Image 32 of 93 For 186 Windward Drive
  33. Image 33 of 93 For 186 Windward Drive
  34. Image 34 of 93 For 186 Windward Drive
  35. Image 35 of 93 For 186 Windward Drive
  36. Image 36 of 93 For 186 Windward Drive
  37. Image 37 of 93 For 186 Windward Drive
  38. Image 38 of 93 For 186 Windward Drive
  39. Image 39 of 93 For 186 Windward Drive
  40. Image 40 of 93 For 186 Windward Drive
  41. Image 41 of 93 For 186 Windward Drive
  42. Image 42 of 93 For 186 Windward Drive
  43. Image 43 of 93 For 186 Windward Drive
  44. Image 44 of 93 For 186 Windward Drive
  45. Image 45 of 93 For 186 Windward Drive
  46. Image 46 of 93 For 186 Windward Drive
  47. Image 47 of 93 For 186 Windward Drive
  48. Image 48 of 93 For 186 Windward Drive
  49. Image 49 of 93 For 186 Windward Drive
  50. Image 50 of 93 For 186 Windward Drive
  51. Image 51 of 93 For 186 Windward Drive
  52. Image 52 of 93 For 186 Windward Drive
  53. Image 53 of 93 For 186 Windward Drive
  54. Image 54 of 93 For 186 Windward Drive
  55. Image 55 of 93 For 186 Windward Drive
  56. Image 56 of 93 For 186 Windward Drive
  57. Image 57 of 93 For 186 Windward Drive
  58. Image 58 of 93 For 186 Windward Drive
  59. Image 59 of 93 For 186 Windward Drive
  60. Image 60 of 93 For 186 Windward Drive
  61. Image 61 of 93 For 186 Windward Drive
  62. Image 62 of 93 For 186 Windward Drive
  63. Image 63 of 93 For 186 Windward Drive
  64. Image 64 of 93 For 186 Windward Drive
  65. Image 65 of 93 For 186 Windward Drive
  66. Image 66 of 93 For 186 Windward Drive
  67. Image 67 of 93 For 186 Windward Drive
  68. Image 68 of 93 For 186 Windward Drive
  69. Image 69 of 93 For 186 Windward Drive
  70. Image 70 of 93 For 186 Windward Drive
  71. Image 71 of 93 For 186 Windward Drive
  72. Image 72 of 93 For 186 Windward Drive
  73. Image 73 of 93 For 186 Windward Drive
  74. Image 74 of 93 For 186 Windward Drive
  75. Image 75 of 93 For 186 Windward Drive
  76. Image 76 of 93 For 186 Windward Drive
  77. Image 77 of 93 For 186 Windward Drive
  78. Image 78 of 93 For 186 Windward Drive
  79. Image 79 of 93 For 186 Windward Drive
  80. Image 80 of 93 For 186 Windward Drive
  81. Image 81 of 93 For 186 Windward Drive
  82. Image 82 of 93 For 186 Windward Drive
  83. Image 83 of 93 For 186 Windward Drive
  84. Image 84 of 93 For 186 Windward Drive
  85. Image 85 of 93 For 186 Windward Drive
  86. Image 86 of 93 For 186 Windward Drive
  87. Image 87 of 93 For 186 Windward Drive
  88. Image 88 of 93 For 186 Windward Drive
  89. Image 89 of 93 For 186 Windward Drive
  90. Image 90 of 93 For 186 Windward Drive
  91. Image 91 of 93 For 186 Windward Drive
  92. Image 92 of 93 For 186 Windward Drive
  93. Image 93 of 93 For 186 Windward Drive
Image Gallery

PRICED AT ONLY: $749,900

Address: 186 Windward Drive, OSPREY, FL 34229

Description

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 marinawith residents only boat slipsprovides direct Intracoastal Waterway access with no fixed bridges to the Gulf. The community is welcoming and livelyperfect 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.**

Property Location and Similar Properties

All
Similar
Payment Calculator
  •   Principal & Interest -
  •   Property Tax $
  •   Home Insurance $
  •   HOA Fees $
  •   Mortgage Insurance-
  •   Monthly -
For a Fast & FREE Mortgage Pre-ApprovalApply Now
Virtual Tour
More Like This
  • MLS#: N6142087 ( Residential )
  • Street Address: 186 Windward Drive
  • Viewed: 11
  • Price: $749,900
  • Price sqft: $227
  • Waterfront: No
  • Year Built: 1983
  • Bldg sqft: 3298
  • Bedrooms: 3
  • Total Baths: 2
  • Full Baths: 2
  • Garage / Parking Spaces: 2
  • Days On Market: 53

Description

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 marinawith residents only boat slipsprovides direct Intracoastal Waterway access with no fixed bridges to the Gulf. The community is welcoming and livelyperfect 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.**
Request More Information
  • All fields are required.
Features
Building and Construction
  • Covered Spaces: 0.00
  • Exterior Features: Lighting, Private Mailbox, Rain Gutters, Sliding Doors
  • Flooring: Wood
  • Living Area: 2505.00
  • Roof: Tile
Land Information
  • Lot Features: Corner Lot, Landscaped, Paved
School Information
  • High School: Venice Senior High
  • Middle School: Sarasota Middle
  • School Elementary: Laurel Nokomis Elementary
Garage and Parking
  • Garage Spaces: 2.00
  • Open Parking Spaces: 0.00
  • Parking Features: Deeded, Driveway, Garage Door Opener, Off Street
Eco-Communities
  • Water Source: Public
Utilities
  • Carport Spaces: 0.00
  • Cooling: Central Air
  • Heating: Central
  • Pets Allowed: Yes
  • Sewer: Public Sewer
  • Utilities: BB/HS Internet Available, Cable Available, Cable Connected, Electricity Available, Electricity Connected, Sewer Available, Sewer Connected, Water Available, Water Connected
Amenities
  • Association Amenities: Basketball Court, Clubhouse, Fitness Center, Park, Pickleball Court(s), Playground, Pool, Tennis Court(s)
Finance and Tax Information
  • Home Owners Association Fee Includes: Common Area Taxes, Pool, Escrow Reserves Fund, Fidelity Bond, Management
  • Home Owners Association Fee: 613.00
  • Insurance Expense: 0.00
  • Net Operating Income: 0.00
  • Other Expense: 0.00
  • Tax Year: 2025
Other Features
  • Appliances: Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
  • Association Name: Judy Brown
  • Association Phone: (941)966-4237
  • Country: US
  • Furnished: Unfurnished
  • 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)
  • Legal Description: LOT 136 SOUTHBAY YACHT & RACQUET CLUB
  • Levels: One
  • Area Major: 34229 - Osprey
  • Occupant Type: Vacant
  • Parcel Number: 0157070011
  • View: Garden
  • Views: 11
  • Zoning Code: RSF2
Nearby Subdivisions
3200 - Palms At Casey Key   Bay Acres Resub   Bay Oaks Estates   Bayside   Bishops Court At Oaks Preserve   Bishops Court At The Oaks Pres   Bishopscourt At The Oaks Prese   Blackburn Harbor Waterfront Vi   Blackburn Point Woods   Casey Key   Dry Slips At Bellagio Harbor V   Dry Slips At Bellagio Village   Harms Sub   Heron Bay Club Sec I   North Creek Estates   North Creek Ests   Oaks   Oaks 2 Ph 1   Oaks 2 Ph 2   Oaks 2 Ph 4c Pt 3   Oaks 2 Phase 2   Oaks 3 Ph 1   Oaks Bayside   Palmer   Palmscasey Key   Park Trace Estates   Pine Ranch   Pine Ranch East   Rivendell   Rivendell The Woodlands At Riv   Rivendell Woodlands   Sarabay Acres   Saunders V A Resub   Siesta Rev Resub Of Pt   Sorrento Shores   Sorrento Villas 1   South Creek   Southbay Yacht Racquet Club   The Oaks   The Oaks Bayside   Trinity Acres   Webbs W D Add   Willowbend Ph 2   Willowbend Ph 2a   Willowbend Ph 3   Willowbend Phase 3  
Similar Properties

Active
Details for 903 Tranquility Circle, OSPREY, FL 34229
$879,000.00 ($251.14 / sqft )

903 Tranquility Circle Virtual Tour Green Listing More Like This

**IMPRESSIVE POOL/SPA HOME on a Desirable Corner Lot with Partial Water View** Custom built by John Cannon and situated on an interior Cul De Sac in popular North Creek Estates, this 3 BED + Office/De

  1. Request Information
  1. Bedrooms: 3
  2. Baths: 3
  3. Approx. 3500 sqft
  1. MLSID: A4669102
  2. Provided by GENEROUS PROPERTY
  3. Contact Mark Lyda
  4. mfrmls
  5. DMCA Notice
39 Pictures and Information
Active
Details for 919 Tranquility Circle Circle, OSPREY, FL 34229
$799,000.00 ($227.77 / sqft )

919 Tranquility Circle Circle Virtual Tour Reduced More Like This

WOW! TOTAL OF 50,000 PRICE ADJUSTMENT! RARE OPPORTUNITY to own this stunning former John Cannon model home on peaceful Tranquility Circle . This pristine 4BR/3.5BA pool home is a kayaker and nature l

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 4
  3. Approx. 3508 sqft
  1. MLSID: A4678841
  2. Provided by TIDELINE REAL ESTATE BROKERS
  3. Contact Ann Winger
  4. mfrmls
  5. DMCA Notice
63 Pictures and Information
Active
Details for 650 Crane Prairie Way, OSPREY, FL 34229
$799,990.00 ($195.50 / sqft )

650 Crane Prairie Way Virtual Tour More Like This

Opportunities like this are increasingly rare in Willowbend. Offering over 3,180 square feet, this Lee Wetherington built residence delivers exceptional scale, thoughtful architecture, and a preserve

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 4
  3. Approx. 4092 sqft
  1. MLSID: A4680121
  2. Provided by MICHAEL SAUNDERS & COMPANY
  3. Contact Cheri Mazan Castro
  4. mfrmls
  5. DMCA Notice
63 Pictures and Information
Active
Details for 1211 Lost Creek Court, OSPREY, FL 34229
$829,000.00 ($206.42 / sqft )

1211 Lost Creek Court Green Listing More Like This

**BEAUTIFULLY UPDATED AND MOVE IN READY, THIS SPACIOUS 4 BEDROOM + OFFICE/DEN HOME OFFERS NEARLY 2,900 SQUARE FEET** of thoughtfully designed living space with potential for a private in law or multi

  1. Request Information
  1. Bedrooms: 4
  2. Baths: 3
  3. Approx. 4016 sqft
  1. MLSID: A4680671
  2. Provided by GENEROUS PROPERTY
  3. Contact Mark Lyda
  4. mfrmls
  5. DMCA Notice
42 Pictures and Information
Active
Details for 664 Crane Prairie Way, OSPREY, FL 34229
$897,000.00 ($231.07 / sqft )

664 Crane Prairie Way Virtual Tour More Like This

Its always about the view and the new tile roof December 2025. This stunning waterfront home in Willowbend, bordering community greenbelt with views to Oscar Scherer State Park, is a luxurious Lee Wet

  1. Request Information
  1. Bedrooms: 3
  2. Baths: 3
  3. Approx. 3882 sqft
  1. MLSID: A4681662
  2. Provided by PREMIER SOTHEBY'S INTERNATIONAL REALTY
  3. Contact Todd Currey
  4. mfrmls
  5. DMCA Notice
70 Pictures and Information

Contact Info

Skip to Main Content
  1. Broker IDX Sites Inc.
  2. A Winning Team
Broker IDX Billing System

Looking To Sell Your Property ?

Connecting agents, buyers, and sellers
Call Us Now Get In Touch
Featured Listings
337 Rutledge Avenue
910 Lake Avenue
2700 Atlantic Avenue 1021
117 Oceans Circle
116 Oceans Circle
156 Mendoza Circle

Copyright ©2006-2026 brokerIDXsites.com   |   All Rights Reserved.