102 Windward Dr, Osprey, FL 34229
SOLD
JUN 4, 2026

102 Windward Dr
Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,134 sqft (on 0.36 acres)

$565,000

Last Sold: Jun 4, 2026
13% below list $650K
$265/sqft
Est. Refi. Payment $3,453/mo*
Refinance Your Home

$565,000

Last Sold: Jun 4, 2026
13% below list $650K
$265/sqft
Est. Refi. Payment $3,453/mo*
Refinance Your Home
3 Beds
2.5 Baths
2,134 sqft
(on 0.36 acres)

Local Information

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

Description

NEW PRICE! Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2.5-bath pool home with mature landscaping offers a functional layout and excellent community amenities. The home features a double-door front entry, a spacious great room with cathedral ceiling, an oversized garage, and a large private lot. Interior highlights include double primary bedrooms, tiled walk-in showers in both full bathrooms, an outdoor shower, a generous laundry room with cabinetry, a practical kitchen with pantry and hurricane rated windows. The paver lanai with automated hurricane screen and expansive paver deck surrounding the swimming pool with solar heat provide substantial outdoor living space. A long driveway adds convenient additional parking. Southbay Yacht & Racquet Club is a golf-cart-friendly community featuring a recently remodeled 10,000 sq. ft. clubhouse with a fitness center, pool, and large patio. The community-owned marina—with residents-only boat slips—provides direct Intracoastal Waterway access with no fixed bridges to the Gulf. Additional amenities include pickleball and tennis courts, bocce, shuffleboard, walking and biking paths, and a playground. The community is ideally situated between Sarasota and Venice, close to dining, shopping, entertainment, beaches, the Legacy Trail, and Pine View School.
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 June 04, 2026

Home Highlights

Parking
2 Car Garage
Outdoor
Patio, Deck, Pool
View
No Info
HOA
$219/Monthly
Price/Sqft
$265/sqft
Listed
180+ days ago

Home Details for 102 Windward Dr

Interior Features

Interior Details
Number of Rooms: 9Types of Rooms: Primary Bedroom, Bedroom 3, Balcony Porch Lanai, Dinette, Dining Room, Great Room, Kitchen, Laundry
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2134 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Connected, Sewer Connected, Sprinkler Meter, Water ConnectedAppliances: Dishwasher, Disposal, Dryer, Microwave, Refrigerator, WasherDishwasherDisposalDryerLaundry: Electric Dryer Hookup,Inside,Washer HookupMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
No Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Window TreatmentsDoor: Outdoor Shower, Sliding DoorsFlooring: Carpet, Ceramic Tile, Vinyl
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Carpet, Ceramic Tile, Vinyl
View
No View

Exterior Features

Exterior Home Features
Roof: TilePatio / Porch: Covered, Deck, Patio, ScreenedExterior: Irrigation System, Lighting, Outdoor Shower, Rain Gutters, Sprinkler MeteredFoundation: SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Other Parking: Garage Dimensions: 23x23No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Driveway,Garage Door Opener,Ground Level,Off Street,Oversized
Pool
Pool: Deck, Gunite, In Ground, Lighting, Outside Bath Access, Screen EnclosurePool
Frontage
Waterfront: WaterfrontRoad Surface Type: AsphaltNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 169

Property Information

Year Built
Year Built: 1986
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Florida
Building
Construction Materials: Block, StuccoNot a New ConstructionNo Additional ParcelsDoes Not Include Home Warranty
Property Information
Condition: CompletedParcel Number: 0157080006

Price & Status

Price
List Price: $650,000Price Per Sqft: $265/sqft
Status Change & Dates
Off Market Date: Thu May 07 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: Laurel Nokomis MiddleHigh School: Venice Senior High

Building

Building Area
Building Area: 3000 Square Feet
Community rooms
Fitness Center

Community

Community Features: Boat Slip, Dock, Intracoastal Waterway, Marina, Waterfront, Clubhouse, Deed Restrictions, Fitness Center, Golf Carts OK, No Truck/RV/Motorcycle Parking, 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, Recreational FacilitiesHOA Name: Rachelle FreedHOA Phone: 941-966-4237Association for this Listing: Sarasota - ManateeHas an HOAHOA Fee: $219/Monthly

Lot Information

Lot Area: 0.36 acres

Listing Info

Special Conditions: None

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: A4671793Showing Considerations: No SignShowing Requirements: Appointment Only, Contact Call Center, Lockbox - Electronic, ShowingTimeUniversal Property Id: US-12115-N-0157080006-R-N

Additional Information

Boat SlipDockIntracoastal WaterwayMarinaWaterfrontClubhouseDeed RestrictionsGolf Carts OKNo Truck/RV/Motorcycle ParkingParkPlaygroundPoolSidewalksTennis Court(s)
Last check for updates: about 15 hours ago
Listed by Regina Putrino, (941) 586-5834
WILLIAM RAVEIS REAL ESTATE, (941) 867-3901
Bought with: Regina Putrino, (941) 586-5834, WILLIAM RAVEIS REAL ESTATE, (941) 867-3901
Originating MLS: Sarasota - Manatee
Source: Stellar MLS, MLS#A4671793
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 102 Windward Dr

DatePriceEventSource
06/04/2026$565,000Sold
Stellar MLS #A4671793
05/08/2026$650,000PendingStellar MLS #A4671793
04/26/2026$650,000PriceChange
Stellar MLS #A4671793
03/24/2026$690,000PriceChange
Stellar MLS #A4671793
01/18/2026$750,000PriceChange
Stellar MLS #A4671793
11/19/2025$800,000Listed For SaleStellar MLS #A4671793
10/09/2008$435,000ListingRemovedAgent Provided
07/11/2008$435,000PriceChange
Agent Provided
03/23/2008$445,000Listed For SaleAgent Provided

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$3,959
Assessment$647,700
Home facts updated by county records

Homeowner tools

Estimated monthly rent$4,414/mo
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Homes for rent near 102 Windward Dr

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Comparable Sales for 102 Windward Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1212 Windward Dr, Osprey, FL
0.04
Single-Family Home
$645,000
08/25/25
3
2
1,994
216 Windward Dr, Osprey, FL
0.18
Single-Family Home
$600,000
11/18/25
3
3
2,575
142 Dory Ln, Osprey, FL
0.09
Single-Family Home
$1,050,000
07/22/25
3
2
2,531
1313 Thornapple Dr, Osprey, FL
0.34
Single-Family Home
$525,000
12/04/25
3
3
2,082
1235 Yacht Harbor Dr, Osprey, FL
0.25
Single-Family Home
$1,065,000
02/20/26
3
3
2,698
1218 Yacht Harbor Dr, Osprey, FL
0.27
Single-Family Home
$1,025,000
04/24/26
3
3
3,297
1303 Thornapple Dr, Osprey, FL
0.37
Single-Family Home
$654,000
04/16/26
3
2
1,929
584 Meadow Sweet Cir, Osprey, FL
0.37
Single-Family Home
$585,000
03/27/26
3
2
2,151

Nearby homes

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Assigned Schools

These are the assigned schools for 102 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
    Flag

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Homes for sale near 102 Windward Dr

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Off Market Homes Near 102 Windward Dr

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102 Windward Dr, Osprey, FL 34229 is a 3 bedroom, 3 bathroom, 2,134 sqft single-family home built in 1986. This property is not currently available for sale. 102 Windward Dr was last sold on Jun 4, 2026 for $565,000 (13% lower than the asking price of $650,000). The current Trulia Estimate for 102 Windward Dr is $564,700.