216 WINDWARD DRIVE, Osprey, FL 34229
OFF MARKET

$595,700

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

216 WINDWARD DRIVE, Osprey, FL 34229

Est. Refi. Payment $3,904/mo*
Refinance Your Home
Currently Off Market - Sold Nov 18, 2025 for $600,000

Home Value

Trulia Estimate
$596K
Since last month
$100 (0%)
Since last year
Decreased$259K (-30.3%)
Since last sale
Decreased$4K (-0.7%)
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 +25% in the last 10 years
MonthEstimated value
2026
September 2026$596K
August 2026$596K
July 2026$588K
June 2026$590K
May 2026$589K
April 2026$587K
March 2026$590K
February 2026$592K
January 2026$591K
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
204 WINDWARD DRIVE, Osprey, FL
0.02
Single-Family Home
$800,000
08/24/26
3
3
2,486
186 WINDWARD DRIVE, Osprey, FL
0.06
Single-Family Home
$565,000
07/20/26
3
2
2,505
1235 YACHT HARBOR DRIVE, Osprey, FL
0.09
Single-Family Home
$1,065,000
02/20/26
3
3
2,698
102 WINDWARD DRIVE, Osprey, FL
0.18
Single-Family Home
$565,000
06/04/26
3
2.5
2,134
1218 YACHT HARBOR DRIVE, Osprey, FL
0.10
Single-Family Home
$1,025,000
04/24/26
3
3
3,297
486 YACHT HARBOR DRIVE, Osprey, FL
0.17
Single-Family Home
$1,325,000
08/25/26
3
3.5
2,939
3957 WAYPOINT AVENUE, Osprey, FL
0.27
Single-Family Home
$900,000
01/16/26
3
3
2,328
3936 WAYPOINT AVENUE, Osprey, FL
0.29
Single-Family Home
$1,001,000
04/27/26
3
3
2,323

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
204 WINDWARD DRIVE, Osprey, FL 34229
0.02
$800,000
3
3
2,486
Recently Sold
1237 FLYING BRIDGE LANE, Osprey, FL 34229
0.08
$843,400
3
2
2,045
Off Market
186 WINDWARD DRIVE, Osprey, FL 34229
0.06
$565,000
3
2
2,505
Recently Sold
188 DORY LANE, Osprey, FL 34229
0.10
$787,800
3
2
2,069
Off Market
1235 YACHT HARBOR DRIVE, Osprey, FL 34229
0.09
$1,065,000
3
3
2,698
Recently Sold
1218 YACHT HARBOR DRIVE, Osprey, FL 34229
0.10
$1,025,000
3
3
3,297
Recently Sold
142 DORY LANE, Osprey, FL 34229
0.15
$1,027,100
3
2
2,531
Off Market
360 PINE RUN DRIVE, Osprey, FL 34229
0.14
$255,400
2
2
1,379
Off Market
362 PINE RUN DRIVE, Osprey, FL 34229
0.14
$215,000
2
2
1,224
Recently Sold
750 PINE RUN DRIVE, Osprey, FL 34229
0.14
$126,600
1
1
586
Off Market
756 PINE RUN DRIVE, Osprey, FL 34229
0.14
$261,200
2
2
1,224
Off Market

Local Information

  • Map ViewExplore the area around 216 WINDWARD DRIVE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1982
0.3 acre lot
2,575 sqft
$231/sqft
2 Car Garage
HOA $150/mo

About this House

What's unique:Tennis courtsBocci ballDouble entry doorsPrivate community marinaCircular drivewayFormal living
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!
216 WINDWARD DRIVE, Osprey, FL 34229 is a 3 bedroom, 3 bathroom, 2,575 sqft single-family home built in 1982. It last sold for $600,000 on Nov 18, 2025 (29% below the $850,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $595,700, with a rent estimate of $4,729/month.
Last check for updates: about 19 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

Home Details for 216 WINDWARD DRIVE

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: $850,000
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)

Price and Tax history

DateEventPrice
Nov 18, 2025
Source: N/A
Sold
$600,000
Nov 20, 2023
Source: Stellar MLS #A4579628
Sold
$782,500
Oct 19, 2023
Source: Stellar MLS #A4579628
Pending
$850,000
Aug 17, 2023
Source: Stellar MLS #A4579628
Listed For Sale
$850,000
Jun 7, 2001
Source: N/A
Sold
$280,000

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 216 WINDWARD DRIVE

  • What is 216 WINDWARD DRIVE estimated to be worth?
    Trulia's estimated value for 216 WINDWARD DRIVE in Osprey, FL is $595,700.
  • What is the price history for 216 WINDWARD DRIVE?
    216 WINDWARD DRIVE in Osprey, FL last sold for $600,000 in November 2025.
  • 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 216 WINDWARD DRIVE have air conditioning?
    Yes, 216 WINDWARD DRIVE in Osprey, FL has air conditioning.
  • Does 216 WINDWARD DRIVE have a pool?
    Yes, 216 WINDWARD DRIVE in Osprey, FL has a pool.

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