186 WINDWARD DRIVE, Osprey, FL 34229
SOLD
JUL 20, 2026

$564,900

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 2,505 sqft (on 0.30 acres)

186 WINDWARD DRIVE, Osprey, FL 34229

Est. Refi. Payment $3,649/mo*
Refinance Your Home
Currently Off Market - Sold Jul 20, 2026 for $565,000 (6% below list price)

Home Value

Trulia Estimate
$565K
Since last month
Decreased$700 (-0.1%)
Since last year
Decreased$161K (-22.2%)
Since last sale
Decreased$700 (-0.1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +40% in the last 10 years
MonthEstimated value
2026
September 2026$564K
August 2026$565K
July 2026$565K
June 2026$570K
May 2026$568K
April 2026$621K
March 2026$622K
February 2026$708K
January 2026$713K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
216 WINDWARD DRIVE, Osprey, FL
0.06
Single-Family Home
$600,000
11/18/25
3
3
2,575
204 WINDWARD DRIVE, Osprey, FL
0.04
Single-Family Home
$800,000
08/24/26
3
3
2,486
102 WINDWARD DRIVE, Osprey, FL
0.12
Single-Family Home
$565,000
06/04/26
3
2.5
2,134
1235 YACHT HARBOR DRIVE, Osprey, FL
0.13
Single-Family Home
$1,065,000
02/20/26
3
3
2,698
1218 YACHT HARBOR DRIVE, Osprey, FL
0.15
Single-Family Home
$1,025,000
04/24/26
3
3
3,297
288 WOODS POINT ROAD, Osprey, FL
0.18
Single-Family Home
$445,000
04/10/26
3
2
1,788
510 LATITUDE LANE, Osprey, FL
0.58
Single-Family Home
$550,000
03/23/26
3
2
2,298

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
188 DORY LANE, Osprey, FL 34229
0.07
$787,800
3
2
2,069
Off Market
204 WINDWARD DRIVE, Osprey, FL 34229
0.04
$800,000
3
3
2,486
Recently Sold
216 WINDWARD DRIVE, Osprey, FL 34229
0.06
$595,500
3
3
2,575
Off Market
142 DORY LANE, Osprey, FL 34229
0.10
$1,028,100
3
2
2,531
Off Market
1237 FLYING BRIDGE LANE, Osprey, FL 34229
0.10
$842,800
3
2
2,045
Off Market
1212 WINDWARD DRIVE, Osprey, FL 34229
0.12
$635,300
3
2
1,994
Off Market
102 WINDWARD DRIVE, Osprey, FL 34229
0.12
$565,000
3
2.5
2,134
Recently Sold
104 WOODLAND PLACE, Osprey, FL 34229
0.13
$260,600
2
2
1,316
Off Market
105 WOODLAND PLACE, Osprey, FL 34229
0.13
$233,900
2
2
1,325
Off Market
107 WOODLAND PLACE #107, Osprey, FL 34229
0.13
$147,000
1
1.5
865
Off Market
111 WOODLAND PLACE, Osprey, FL 34229
0.13
$227,000
2
2
1,316
Recently Sold

Local Information

  • Map ViewExplore the area around 186 WINDWARD DRIVE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1983
0.3 acre lot
2,505 sqft
$226/sqft
2 Car Garage
HOA $204/mo

About this House

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.**
186 WINDWARD DRIVE, Osprey, FL 34229 is a 3 bedroom, 2 bathroom, 2,505 sqft single-family home built in 1983. It last sold for $565,000 on Jul 20, 2026 (6% below the $599,900 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $564,900, with a rent estimate of $2,621/month.
Last check for updates: about 14 hours ago
Listed by Brittany Coleman, PLLC, (941) 539-5023
KELLER WILLIAMS ON THE WATER S, (941) 803-7522
Bought with: Brittany Coleman, PLLC, (941) 539-5023, KELLER WILLIAMS ON THE WATER S, (941) 803-7522
Originating MLS: Sarasota - Manatee
Source: Stellar MLS, MLS#N6142087
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

Home Details for 186 WINDWARD DRIVE

Interior Features

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

Exterior Features

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

Days on Market

Cumulative Days on Market: 116

Property Information

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

Price & Status

Price
List Price: $599,900Price Per Sqft: $226/sqft
Status Change & Dates
Off Market Date: Wed May 13 2026

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: OSPREYCommunity: SOUTHBAY YACHT & RACQUET CLUB
School Information
Elementary School: Laurel Nokomis ElementaryJr High / Middle School: Sarasota MiddleHigh School: Venice Senior High

Building

Building Area
Building Area: 3298 Square Feet
Community rooms
Fitness Center

Community

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

HOA

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

Lot Information

Lot Area: 0.30 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

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

Additional Information

HOA Amenities: Basketball Court,Clubhouse,Fitness Center,Park,Pickleball Court(s),Playground,Pool,Tennis Court(s)

Price and Tax history

DateEventPrice
Jul 20, 2026
Source: Stellar MLS #N6142087
Sold
$565,000
Jul 8, 2026
Source: Stellar MLS #N6142087
Contingent
$599,900
May 13, 2026
Source: Stellar MLS #N6142087
Pending
$599,900
May 7, 2026
Source: Stellar MLS #N6142087
PriceChange
$599,900
Price decreased by 8%
Mar 19, 2026
Source: Stellar MLS #N6142087
PendingToActive
$649,500

Market trends in Osprey

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$714K
$28.67KMoM
Sale-to-List Price
—
Price per sq ft
—
Available listings
112
22MoM

Around this home

What Locals Say about Osprey

At least 46 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

  • 75 % Say people would walk alone at night

  • 74 % Say there's wildlife

  • 67 % Say yards are well-kept

  • 67 % Say there's holiday spirit

  • 64 % Say they plan to stay for at least 5 years

  • 54 % Say neighbors are friendly

  • 48 % Say there are sidewalks

  • 42 % Say it's walkable to restaurants

  • 42 % Say streets are well-lit

  • 41 % Say it's walkable to grocery stores

  • 41 % Say there are community events

  • 31 % Say kids play outside

Sourced by Trulia users. Learn more about our methodology.
  • Lindsey W.
    "It’s a quiet and low key suburb area of Sarasota county. It’s very accessible to I-75 and Nokomis beach and about a 25 minute drive to siesta key beach. "
    4
    Flag
  • Mary V.
    "I am retired now but my commute to Stickney Point was only about 10 min and downtown was about 25 min during rush hour when there is no construction "
    0
    Flag
  • Mary V.
    "Pineview School is very close, nice safe area for children. CVS and Publix are also close, as well as Historic Spanish Pointe. The beach is ten minutes or less."
    3
    Flag
  • Bob T.
    "I don’t commute....retired. There are no sidewalks here and our street has a large amount of speeders making walking dangerous. Some neighbors park on the county right of way destroying our water flow/drainage which has caused flooding here. Many homes are unkept even though there is an active hoa."
    14
    Flag
  • Bob T.
    "Neighborhood is pet friendly. Wide road we walking dogs. Only problem noticed now is daily construction vehicles speeding in neighborhood."
    1
    Flag
  • Larysathor
    "Well, the Mother Nature taking its tall, water level raised over last ten years and a lot of beaches are washed out to nonexistence."
    0
    Flag
  • Brenda F. D.
    "Neighborhood is beautiful love the area close to everything and beaches and shopping . Local restaurant "
    1
    Flag
  • Michelle C.
    "I've lived in this neighborhood for twenty years +. My neighbors are the friendliest. We all look out for each other and lend a hand when needed. Can't think of anywhere else I'd want to live."
    0
    Flag
  • nancybuscher
    "This quiet, beautifully landscaped, pet friendly subdivision is close to beaches, shopping, restaurants, cultural events in Sarasota and Venice, beside Oscar Scherer State Park for hickers & boaters, and has easy access to airports by way of US41 & I-75."
    0
    Flag
  • info
    "Centrally located, minutes to beaches and shopping"
    1
    Flag
  • bookwoman39
    "Wonderful community, close to Sarasota and all restaurants, cultural activities, etc. The condo development is a designated bird sanctuary. Nice pools, exercise room, community room. Good neighbors. What the development lacks is diversity. "
    0
    Flag
  • trishmainey1111
    "Osprey Florida is one of the most beautiful, accessible communities in Florida. Ten minutes to the white sands beach and ten minutes to I-75. "
    1
    Flag
  • Gail L.
    "I work here, belong to the club and have lived in the neighborhood for the last 12 years it is one of 5 golf communities I have belonged to and bar none my favorite due to the people that live here. They are multicultural, down to earth and just fabulous. This is a community that rates above the rest . it is very common for folks to move up and down in house sizes and styles as their lifestyles change. Give me a call as I'd love to show you around. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 186 WINDWARD DRIVE

  • What is 186 WINDWARD DRIVE estimated to be worth?
    Trulia's estimated value for 186 WINDWARD DRIVE in Osprey, FL is $564,900.
  • What is the price history for 186 WINDWARD DRIVE?
    186 WINDWARD DRIVE in Osprey, FL last sold for $565,000 in July 2026.
  • Is Osprey a buyer's or seller's market?
    Osprey is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Osprey?
    The median sale price in Osprey is $714K. That is up $28.67K from the prior month.
  • Does 186 WINDWARD DRIVE have air conditioning?
    Yes, 186 WINDWARD DRIVE in Osprey, FL has air conditioning.
  • Does 186 WINDWARD DRIVE have a pool?
    Yes, 186 WINDWARD DRIVE in Osprey, FL has a pool.

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