204 WINDWARD DRIVE, Osprey, FL 34229
SOLD
AUG 24, 2026

$796,400

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 2,486 sqft (on 0.30 acres)

204 WINDWARD DRIVE, Osprey, FL 34229

Est. Refi. Payment $5,114/mo*
Refinance Your Home
Currently Off Market - Sold Aug 24, 2026 for $800,000 (6% below list price)

Home Value

Trulia Estimate
$796K
Since last month
Decreased$4K (-0.5%)
Since last year
Decreased$7K (-0.8%)
Since last sale
Decreased$4K (-0.5%)
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 +65% in the last 10 years
MonthEstimated value
2026
September 2026$796K
August 2026$800K
July 2026$797K
June 2026$934K
May 2026$990K
April 2026$799K
March 2026$775K
February 2026$786K
January 2026$758K
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
0.02
Single-Family Home
$600,000
11/18/25
3
3
2,575
1235 YACHT HARBOR DRIVE, Osprey, FL
0.10
Single-Family Home
$1,065,000
02/20/26
3
3
2,698
186 WINDWARD DRIVE, Osprey, FL
0.04
Single-Family Home
$565,000
07/20/26
3
2
2,505
1218 YACHT HARBOR DRIVE, Osprey, FL
0.11
Single-Family Home
$1,025,000
04/24/26
3
3
3,297
102 WINDWARD DRIVE, Osprey, FL
0.16
Single-Family Home
$565,000
06/04/26
3
2.5
2,134
3957 WAYPOINT AVENUE, Osprey, FL
0.27
Single-Family Home
$900,000
01/16/26
3
3
2,328
486 YACHT HARBOR DRIVE, Osprey, FL
0.19
Single-Family Home
$1,325,000
08/25/26
3
3.5
2,939
3936 WAYPOINT AVENUE, Osprey, FL
0.30
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
216 WINDWARD DRIVE, Osprey, FL 34229
0.02
$595,500
3
3
2,575
Off Market
1237 FLYING BRIDGE LANE, Osprey, FL 34229
0.08
$842,800
3
2
2,045
Off Market
186 WINDWARD DRIVE, Osprey, FL 34229
0.04
$565,000
3
2
2,505
Recently Sold
188 DORY LANE, Osprey, FL 34229
0.08
$787,800
3
2
2,069
Off Market
1235 YACHT HARBOR DRIVE, Osprey, FL 34229
0.10
$1,065,000
3
3
2,698
Recently Sold
1218 YACHT HARBOR DRIVE, Osprey, FL 34229
0.12
$1,025,000
3
3
3,297
Recently Sold
142 DORY LANE, Osprey, FL 34229
0.13
$1,028,100
3
2
2,531
Off Market
360 PINE RUN DRIVE, Osprey, FL 34229
0.13
$255,100
2
2
1,379
Off Market
362 PINE RUN DRIVE, Osprey, FL 34229
0.13
$215,000
2
2
1,224
Recently Sold
750 PINE RUN DRIVE, Osprey, FL 34229
0.13
$125,100
1
1
586
Off Market
756 PINE RUN DRIVE, Osprey, FL 34229
0.13
$262,100
2
2
1,224
Off Market

Local Information

  • Map ViewExplore the area around 204 WINDWARD DRIVE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1986
0.3 acre lot
2,486 sqft
$322/sqft
2 Car Garage
HOA $219/mo

About this House

Don't miss this opportunity to own a home in a desirable private marina community. This spacious 3-bedroom, 3-bath home features high ceilings and a beautifully updated kitchen designed for both everyday living and entertaining. An amazing Value! A combination of comfort and style with light-filled living spaces. Enjoy Florida living at its best with a private pool and amazing lanai area with plenty of covered patio. The oversized two car garage provides plenty of space for a golf cart. Southbay Yacht & Racquet Club is a highly sought-after Marina community offering a clubhouse, resort-style amenities and recreational activities for all ages. Tennis, pickleball, bocce ball, playground, kayak launch and storage, jet ski pads, fishing & boating. Southbay Yacht & Racquet Club is a community like no other in that it has a private 172 boat slip Marina with deep water able to accommodate boats up to 58 feet. Walk, bike or take your golf cart to beaches, shopping, restaurants & tiki bars.
204 WINDWARD DRIVE, Osprey, FL 34229 is a 3 bedroom, 3 bathroom, 2,486 sqft single-family home built in 1986. It last sold for $800,000 on Aug 24, 2026 (6% below the $850,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $796,400, with a rent estimate of $4,122/month.
Last check for updates: 1 day 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: Craig Lewis, (941) 966-5400, GOLF & BAY PROPERTIES LLC, (941) 539-8400
Co-Buyer's Agent: Sharon Lewis, (941) 966-5400, GOLF & BAY PROPERTIES LLC, (941) 539-8400
Originating MLS: Sarasota - Manatee
Source: Stellar MLS, MLS#A4693139
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 204 WINDWARD DRIVE

Interior Features

Interior Details
Number of Rooms: 9Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Dining Room, Family Room, Foyer, Kitchen, Living Room, Utility Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2486 Square Feet
Appliances & Utilities
Utilities: BB/HS Internet Available, Cable Available, Electricity Connected, Fiber Optics, Fire Hydrant, Phone Available, Public, Sewer Connected, Sprinkler Meter, Street LightsAppliances: Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Refrigerator, Washer, Wine RefrigeratorDishwasherDisposalDryerLaundry: Inside,Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Spa: In GroundNo FireplaceHas a Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Window Treatments, Hurricane ShuttersDoor: French 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, Deck, Front Porch, ScreenedFencing: MasonryVegetation: Mature Landscaping, Trees/LandscapedExterior: Irrigation System, Lighting, Private Mailbox, Private YardFoundation: Block, SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Other Parking: Garage Dimensions: 30X21No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Driveway,Garage Door Opener,Golf Cart Parking,Off Street
Pool
Pool: Gunite, Heated, In Ground, Lighting, Pool Sweep, Screen EnclosurePool
Frontage
Waterfront: Marina AccessResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: Paved, AsphaltNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 81

Property Information

Year Built
Year Built: 1986
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: 0157070009

Price & Status

Price
List Price: $850,000Price Per Sqft: $322/sqft
Status Change & Dates
Off Market Date: Fri Jul 31 2026Possession Timing: Close Of Escrow, Negotiable

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: 3861 Square Feet
Community rooms
Fitness Center

Community

Community Features: Boat Slip, Fishing, Intracoastal Waterway, Marina, Association Recreation - Owned, Clubhouse, Deed Restrictions, Fitness Center, Golf Carts OK, Park, Playground, Pool, Sidewalks, Tennis Court(s)Not Senior Community
Other
Playground

HOA

HOA Fee Includes: Community Pool, Reserve Fund, Maintenance Grounds, ManagerHOA Name: Rachelle FreedHOA Phone: 941-966-4237Association for this Listing: Sarasota - ManateeHas an HOAHOA Fee: $219/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: A4693139Showing Advance Notice: 24Showing AttendedShowing Considerations: No SignShowing Requirements: 24 Hour Notice, Appointment Only, Listing Agent Must Accompany, ShowingTimeUniversal Property Id: US-12115-N-0157070009-R-N

Additional Information

HOA Amenities: Clubhouse,Fence Restrictions,Fitness Center,Lobby Key Required,Maintenance,Optional Additional Fees,Park,Pickleball Court(s),Playground,Pool,Recreation Facilities,Tennis Court(s),Trail(s)

Price and Tax history

DateEventPrice
Aug 24, 2026
Source: Stellar MLS #A4693139
Sold
$800,000
Jul 31, 2026
Source: Stellar MLS #A4693139
Pending
$850,000
Jul 13, 2026
Source: Stellar MLS #A4693139
PriceChange
$850,000
Price decreased by 15%
Jun 10, 2026
Source: Stellar MLS #A4693139
PriceChange
$999,000
Price decreased by 5%
May 11, 2026
Source: Stellar MLS #A4693139
Listed For Sale
$1,050,000

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 204 WINDWARD DRIVE

  • What is 204 WINDWARD DRIVE estimated to be worth?
    Trulia's estimated value for 204 WINDWARD DRIVE in Osprey, FL is $796,400.
  • What is the price history for 204 WINDWARD DRIVE?
    204 WINDWARD DRIVE in Osprey, FL last sold for $800,000 in August 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 204 WINDWARD DRIVE have air conditioning?
    Yes, 204 WINDWARD DRIVE in Osprey, FL has air conditioning.
  • Does 204 WINDWARD DRIVE have a pool?
    Yes, 204 WINDWARD DRIVE in Osprey, FL has a pool.

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