216 Windward Dr, Osprey, FL 34229
SOLD
NOV 18, 2025

216 Windward Dr
Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,575 sqft (on 0.30 acres)

$600,000

Last Sold: Nov 18, 2025
29% below list $850K
$233/sqft
Est. Refi. Payment $3,678/mo*
Refinance Your Home

$600,000

Last Sold: Nov 18, 2025
29% below list $850K
$233/sqft
Est. Refi. Payment $3,678/mo*
Refinance Your Home
3 Beds
3 Baths
2,575 sqft
(on 0.30 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

This is your rare chance to own a custom built home in the "One of a Kind" Marina Community of Southbay! Beautifully maintained three bedroom three bath home. Come enjoy the true Florida lifestyle. The circular driveway and double entry doors welcome you and your guests into this lovely piece of paradise. Features include, Formal Living and Dining rooms, a well appointed kitchen with adjoining family room with fireplace and fantastic view of the pool and privately walled back yard. Enjoy the Community Clubhouse with activities for the entire family. Private Community Marina, Playground, Community Park on The Intracoastal Waterway, Tennis Courts, Pickleball, Bocci Ball and so much more! Walk, Bike or Drive your Golf Cart to shopping, restaurants County Parks and Tiki Bars. This is a must see. You'll be so happy you found Southbay!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from February 27, 2024

Home Highlights

Parking
2 Car Garage
Outdoor
Pool
View
No Info
HOA
$150/Monthly
Price/Sqft
$233/sqft
Listed
180+ days ago

Home Details for 216 Windward Dr

Interior Features

Interior Details
Number of Rooms: 7Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2575 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Electricity Connected, Fiber Optics, Fire Hydrant, Phone Available, Public, Sewer Connected, Street Lights, Underground Utilities, Water ConnectedAppliances: Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, WasherDishwasherDisposalDryerLaundry: Inside,Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central Air,Humidity ControlHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Family Room, Masonry, Wood BurningHas a FireplaceNo Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Window Treatments, Hurricane Shutters/WindowsDoor: Sliding DoorsFlooring: Carpet, Ceramic Tile
Levels, Entrance, & Accessibility
Stories: 1Number of Stories: 1Levels: OneFloors: Carpet, Ceramic Tile
View
No View

Exterior Features

Exterior Home Features
Roof: TilePatio / Porch: Covered, Enclosed, ScreenedVegetation: Mature LandscapingExterior: Irrigation System, Lighting, Private Mailbox, Sprinkler MeteredFoundation: SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Circular Driveway,Driveway,Garage Door Opener
Pool
Pool: Gunite, In Ground, Lighting, Screen EnclosurePool
Frontage
Waterfront: Intracoastal Waterway Access, Marina Access, Minimum Wake Zone, Sailboat Water, SeawallResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: Paved, AsphaltNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 63

Property Information

Year Built
Year Built: 1982
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Custom
Building
Construction Materials: Block, Concrete, StuccoNot a New ConstructionNo Additional ParcelsDoes Not Include Home Warranty
Property Information
Parcel Number: 0157070008

Price & Status

Price
List Price: $850,000Price Per Sqft: $233/sqft
Status Change & Dates
Off Market Date: Thu Oct 19 2023Possession Timing: Close Of Escrow

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: Laurel Nokomis MiddleHigh School: Venice Senior High

Building

Building Area
Building Area: 3415 Square Feet
Community rooms
Fitness Center

Community

Community Features: Marina, Water Access, Association Recreation - Owned, Clubhouse, Deed Restrictions, Fitness Center, Golf Carts OK, Park, Playground, Pool, SidewalksNot Senior Community
Other
Playground

HOA

HOA Fee Includes: Community Pool, Reserve Fund, Insurance, Maintenance Grounds, Manager, Pool Maintenance, Recreational FacilitiesHOA Name: Judy BownHOA Phone: 941-966-4237Association for this Listing: Sarasota - ManateeHas an HOAHOA Fee: $150/Monthly

Lot Information

Lot Area: 0.30 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: A4579628Showing Advance Notice: 24Showing AttendedShowing Considerations: No SignShowing Requirements: 24 Hour Notice, Appointment Only, Listing Agent Must Accompany, ShowingTimeUniversal Property Id: US-12115-N-0157070008-R-N

Additional Information

HOA Amenities: Basketball Court,Clubhouse,Fence Restrictions,Fitness Center,Lobby Key Required,Maintenance,Optional Additional Fees,Park,Pickleball Court(s),Playground,Pool,Recreation Facilities,Shuffleboard Court,Tennis Court(s)
Last check for updates: about 7 hours ago
Listed by Sharon Lewis, (941) 966-5400
GOLF & BAY PROPERTIES LLC, (941) 539-8400
Craig Lewis, (941) 966-5400
GOLF & BAY PROPERTIES LLC, (941) 539-8400
Bought with: Magda Cetta Whelton, (941) 408-4047, ENGEL & VOELKERS VENICE DOWNTOWN, (941) 388-9800
Originating MLS: Sarasota - Manatee
Source: Stellar MLS, MLS#A4579628
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

Price History for 216 Windward Dr

DatePriceEventSource
11/18/2025$600,000Sold
N/A
11/20/2023$782,500Sold
Stellar MLS #A4579628
10/19/2023$850,000PendingStellar MLS #A4579628
08/17/2023$850,000Listed For SaleStellar MLS #A4579628
06/07/2001$280,000Sold
N/A

Market trends in Osprey

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$569K
$30.33KMoM
Sale-to-List Price
—
Price per sq ft
$269
$8MoM
Available listings
156
6MoM
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Property Tax and Assessment

Year2025
Tax$4,823
Assessment$760,200
Home facts updated by county records

Homeowner tools

Estimated monthly rent$4,880/mo
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Homes for rent near 216 Windward Dr

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Comparable Sales for 216 Windward Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1235 Yacht Harbor Dr, Osprey, FL
0.09
Single-Family Home
$1,065,000
02/20/26
3
3
2,698
102 Windward Dr, Osprey, FL
0.18
Single-Family Home
$565,000
06/04/26
3
2.5
2,134
1218 Yacht Harbor Dr, Osprey, FL
0.10
Single-Family Home
$1,025,000
04/24/26
3
3
3,297
1212 Windward Dr, Osprey, FL
0.17
Single-Family Home
$645,000
08/25/25
3
2
1,994
142 Dory Ln, Osprey, FL
0.15
Single-Family Home
$1,050,000
07/22/25
3
2
2,531
3957 Waypoint Ave, Osprey, FL
0.27
Single-Family Home
$900,000
01/16/26
3
3
2,328
3936 Waypoint Ave, Osprey, FL
0.29
Single-Family Home
$1,001,000
04/27/26
3
3
2,323
447 Oak Point Rd, Osprey, FL
0.21
Single-Family Home
$520,000
12/30/25
4
3
2,688

Nearby homes

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Assigned Schools

These are the assigned schools for 216 Windward Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

  • 53 % Say neighbors are friendly

  • 48 % Say there are sidewalks

  • 42 % Say it's walkable to restaurants

  • 42 % Say streets are well-lit

  • 41 % Say there are community events

  • 40 % Say it's walkable to grocery stores

  • 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
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Homes for sale near 216 Windward Dr

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Off Market Homes Near 216 Windward Dr

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216 Windward Dr, Osprey, FL 34229 is a 3 bedroom, 3 bathroom, 2,575 sqft single-family home built in 1982. This property is not currently available for sale. 216 Windward Dr was last sold on Nov 18, 2025 for $600,000 (29% lower than the asking price of $850,000). The current Trulia Estimate for 216 Windward Dr is $584,500.