186 Windward Dr
Osprey, FL 34229
3 Beds
2 Baths
2,505 sqft (on 0.30 acres)
3 Beds
2 Baths
2,505 sqft
(on 0.30 acres)
Local Information
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Description
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.**
Home Highlights
Parking
2 Car Garage
Outdoor
Patio
View
Garden
HOA
$204/Monthly
Price/Sqft
$259
Listed
117 days ago
Home Details for 186 Windward Dr
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Interior Details Number of Rooms: 11Types of Rooms: Primary Bedroom, Bedroom 1, Bedroom 2, Primary Bathroom, Bathroom 2, Bonus Room, Dinette, Dining Room, Family Room, Kitchen, Living Room |
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2 |
Dimensions and Layout Living Area: 2505 Square Feet |
Appliances & Utilities Utilities: BB/HS Internet Available, Cable Available, Cable Connected, Electricity Available, Electricity Connected, Sewer Available, Sewer Connected, Water Available, Water ConnectedAppliances: Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, WasherDishwasherDryerLaundry: Inside,Laundry RoomMicrowaveRefrigeratorWasher |
Heating & Cooling Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central |
Fireplace & Spa No FireplaceNo Spa |
Gas & Electric Has Electric on Property |
Windows, Doors, Floors & Walls Door: Sliding DoorsFlooring: Hardwood |
Levels, Entrance, & Accessibility Stories: 1Number of Stories: 1Levels: OneFloors: Hardwood |
View Has a ViewView: Garden |
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Exterior Home Features Roof: TilePatio / Porch: Covered, Patio, ScreenedVegetation: Trees/LandscapedExterior: Irrigation System, Lighting, Private Mailbox, Rain GuttersFoundation: SlabNo Private Pool |
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2Other Parking: Garage Dimensions: 21x22No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Deeded,Driveway,Garage Door Opener,Off Street |
Frontage Waterfront: Intracoastal Waterway Access, Marina AccessRoad Surface Type: Paved, AsphaltNot on Waterfront |
Water & Sewer Sewer: Public Sewer |
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Cumulative Days on Market: 107Days on Market: 117 |
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Year Built Year Built: 1983 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family Residence |
Building Construction Materials: Block, StuccoNot a New ConstructionNo Additional Parcels |
Property Information Parcel Number: 0157070011 |
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Price List Price: $649,500Price Per Sqft: $259 |
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MLS Status: Active |
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Direction & Address City: OSPREYCommunity: SOUTHBAY YACHT & RACQUET CLUB |
School Information Elementary School: Laurel Nokomis ElementaryJr High / Middle School: Sarasota MiddleHigh School: Venice Senior High |
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Listing Agent Listing ID: N6142087 |
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Building Area Building Area: 3298 Square Feet |
Community rooms Fitness Center |
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Community Features: Boat Slip, Dock, Intracoastal Waterway, Marina, Clubhouse, Deed Restrictions, Fitness Center, Golf Carts OK, Park, Playground, Pool, Sidewalks, Tennis Court(s)Not Senior Community |
Other Playground |
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HOA Fee Includes: Common Area Taxes, Community Pool, Reserve Fund, Fidelity Bond, Manager, Pool MaintenanceHOA Name: Judy BrownHOA Phone: 941-966-4237Association for this Listing: Sarasota - ManateeHas an HOAHOA Fee: $204/Monthly |
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Lot Area: 0.30 acres |
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Special Conditions: None |
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Listing Terms: Cash, Conventional, FHA, VA Loan |
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Business Information Ownership: Fee Simple |
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Mls Number: N6142087Back On Market Date: Mon May 04 2026Showing Considerations: See RemarksShowing Requirements: Appointment Only, Combination Lock Box, Go Direct, See Remarks, ShowingTimeUniversal Property Id: US-12115-N-0157070011-R-N |
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HOA Amenities: Basketball Court,Clubhouse,Fitness Center,Park,Pickleball Court(s),Playground,Pool,Tennis Court(s) |
Last check for updates: about 6 hours ago
Listing Provided by: Brittany Coleman, PLLC, (941) 539-5023
KELLER WILLIAMS ON THE WATER S, (941) 803-7522
Originating MLS: Sarasota - Manatee
Source: Stellar MLS, MLS#N6142087
Also Listed on Stellar MLS.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511
Price History for 186 Windward Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 03/19/2026 | $649,500 | PendingToActive | Stellar MLS #N6142087 |
| 03/13/2026 | $649,500 | Pending | Stellar MLS #N6142087 |
| 03/06/2026 | $649,500 | PriceChange | Stellar MLS #N6142087 |
| 01/09/2026 | $749,900 | Listed For Sale | Stellar MLS #N6142087 |
| 11/04/2021 | $580,000 | Sold | N/A |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $7,566 |
| Assessment | $588,800 |
Home facts updated by county records
Comparable Sales for 186 Windward Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.06 | Single-Family Home | $600,000 | 11/18/25 | 3 | 3 | 2,575 | |
0.12 | Single-Family Home | $645,000 | 08/25/25 | 3 | 2 | 1,994 | |
0.10 | Single-Family Home | $1,050,000 | 07/22/25 | 3 | 2 | 2,531 | |
0.13 | Single-Family Home | $1,065,000 | 02/20/26 | 3 | 3 | 2,698 | |
0.15 | Single-Family Home | $1,025,000 | 04/24/26 | 3 | 3 | 3,297 | |
0.18 | Single-Family Home | $445,000 | 04/10/26 | 3 | 2 | 1,788 | |
0.19 | Single-Family Home | $489,000 | 07/03/25 | 2 | 2 | 1,862 | |
0.36 | Single-Family Home | $480,000 | 05/14/25 | 3 | 2 | 1,808 | |
0.39 | Single-Family Home | $670,000 | 06/10/25 | 4 | 3 | 2,513 | |
0.26 | Single-Family Home | $1,150,000 | 05/28/25 | 2 | 3 | 2,521 |
Assigned Schools
These are the assigned schools for 186 Windward Dr.
- Laurel Nokomis School
- PK-8
- Public
- 1392 Students
8/10GreatSchools RatingParent Rating AverageWe have went to the school for one year. I have a fifth grader and a seventh grader. My seventh grader is autistic and came with an IEP that they refused to write for him there he was called all types of racial slurs and bullied the entire year. my daughter who was in fifth grade was bullied constantly and a lot of it came from her teacher. She was patted down by her teacher with no one else around. The school is absolutely awful. None of the staff that I have encountered care about their students. The principal is absolutely not reachable. I asked to speak with her several times and was told I need an appointment and when I asked for an appointment, they didn’t have any do not recommend especially for anybody with a special needs child.Parent Review11mo ago - Venice Senior High School
- 9-12
- Public
- 2727 Students
6/10GreatSchools RatingParent Rating AverageBoring + Students there are reckless and rude. I got called the F slur during my 2nd week there.Student Review1mo ago 
Check out schools near 186 Windward Dr.
What Locals Say about Osprey
At least 45 Trulia users voted on each feature.
90 % Say car is needed
87 % Say it's dog friendly
85 % Say it's quiet
84 % Say parking is easy
74 % Say people would walk alone at night
73 % Say there's wildlife
66 % Say yards are well-kept
66 % Say there's holiday spirit
64 % Say they plan to stay for at least 5 years
53 % Say neighbors are friendly
49 % Say there are sidewalks
42 % Say streets are well-lit
41 % Say it's walkable to restaurants
41 % Say there are community events
40 % Say it's walkable to grocery stores
31 % Say kids play outside
Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Brittany Coleman, PLLC, KELLER WILLIAMS ON THE WATER S, (941) 803-7522
Agent Phone: (941) 539-5023
186 Windward Dr, Osprey, FL 34229 is a 3 bedroom, 2 bathroom, 2,505 sqft single-family home built in 1983. This property is currently available for sale and was listed by Stellar MLS on Jan 9, 2026. The MLS # for this home is MLS# N6142087.