204 Windward Dr, Osprey, FL 34229
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Property image
FOR SALE
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0.3 ACRES

204 Windward Dr
Osprey, FL 34229

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

$925,000

Original price: $999,000
Est. Mortgage $5,887/mo*
Get Pre-Qualified

$925,000

Original price: $999,000
Est. Mortgage $5,887/mo*
Get Pre-Qualified
3 Beds
3 Baths
2,486 sqft
(on 0.30 acres)

Local Information

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

Description

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. 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.

Home Highlights

Parking
2 Car Garage
Outdoor
Porch, Deck, Pool
View
No Info
HOA
$219/Monthly
Price/Sqft
$372
Listed
63 days ago

Home Details for 204 Windward Dr

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: 63Days on Market: 63

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: $925,000Price Per Sqft: $372
Status Change & Dates
Possession Timing: Close Of Escrow, Negotiable

Active Status

MLS Status: Active

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

Agent Information

Listing Agent
Listing ID: A4693139

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)
Last check for updates: about 4 hours ago
Listing Provided 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
Originating MLS: Sarasota - Manatee
Source: Stellar MLS, MLS#A4693139
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

Market trends in Osprey

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
139
17MoM

Price History for 204 Windward Dr

DatePriceEventSource
07/13/2026$925,000PriceChange
Stellar MLS #A4693139
06/10/2026$999,000PriceChange
Stellar MLS #A4693139
05/11/2026$1,050,000Listed For SaleStellar MLS #A4693139
10/30/2001$385,000Sold
N/A

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Property Tax and Assessment

Year2025
Tax$4,761
Assessment$644,000
Home facts updated by county records

Comparable Sales for 204 Windward Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
216 Windward Dr, Osprey, FL
0.02
Single-Family Home
$600,000
11/18/25
3
3
2,575
102 Windward Dr, Osprey, FL
0.16
Single-Family Home
$565,000
06/04/26
3
2.5
2,134
1235 Yacht Harbor Dr, Osprey, FL
0.10
Single-Family Home
$1,065,000
02/20/26
3
3
2,698
1218 Yacht Harbor Dr, Osprey, FL
0.11
Single-Family Home
$1,025,000
04/24/26
3
3
3,297
1212 Windward Dr, Osprey, FL
0.15
Single-Family Home
$645,000
08/25/25
3
2
1,994
264 Woods Point Rd, Osprey, FL
0.17
Single-Family Home
$425,000
10/29/25
2
3
2,837
142 Dory Ln, Osprey, FL
0.13
Single-Family Home
$1,050,000
07/22/25
3
2
2,531
288 Woods Point Rd, Osprey, FL
0.16
Single-Family Home
$445,000
04/10/26
3
2
1,788
447 Oak Point Rd, Osprey, FL
0.22
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 204 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

  • 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 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
    Flag

LGBTQ Local Legal Protections

Sharon Lewis, GOLF & BAY PROPERTIES LLC, (941) 539-8400
Agent Phone: (941) 966-5400
204 Windward Dr, Osprey, FL 34229 is a 3 bedroom, 3 bathroom, 2,486 sqft single-family home built in 1986. This property is currently available for sale and was listed by Stellar MLS on May 11, 2026. The MLS # for this home is MLS# A4693139.