217 Windward Dr, Osprey, FL 34229
OFF MARKET

217 Windward Dr
Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,552 sqft (on 0.30 acres)

$998,600

Trulia Estimate
as of Jun 7, 2026
Est. Refi. Payment $6,087/mo*
Refinance Your Home

$998,600

Trulia Estimate
as of Jun 7, 2026
Est. Refi. Payment $6,087/mo*
Refinance Your Home
4 Beds
3 Baths
2,552 sqft
(on 0.30 acres)

Local Information

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

Description

Southbay Yacht & Racquet Club Community has its OWN VERY AFFORDABLE MARINA, Active Clubhouse, Heated Pool, Tennis Courts, Gym, Sauna & Playground. **Completely & Very Tastefully Remodeled **4 Bedroom/3 Full Bath Home with Soaring Ceilings in the Great Room/Dining Room and Kitchen Areas with a lot of Natural Light.**Higher than Normal Ceilings in remainder of home.**Expansive Lanai & Private SOUTH FACING POOL AREA. **Palladium Windows Offering a Light and Airy Entrance to a Perfect Open Floor Plan Home for Entertaining and Family Living. **Completely Never Used Gourmet Kitchen with Custom Wood Cabinets, Beautiful Quartz Countertops along with Stainless Appliances. **Romantic Master Suite Overlooks the Pool thru French Doors with Large Walk In Closet. **The Master Bath Affords Quality Living at its Best with Dual Vanity, Lighted Waterfall Faucets, Oversized Walk In Shower with Stunning Tile & Glass Appointments. **Split Floor Plan Accommodates 2 Bedrooms and Beautifully Appointed Bathroom. **Large 4th Bedroom with En Suite Full Bath Could Also be used as a Separate Family Rm/ Media Rm or Office. **Home is Situated on a PRIVATE CORNER LOT with OVERSIZED 2 1/2 CAR GARAGE with Access from Either Windward Dr or Flying Bridge. ** IMPORTANT!! Home Does "NOT Require Flood Ins" as it Sits on One of the Highest Lot Elevations in the Community! **Sought after Nearby Pineview School (grades 2-12) is Ranked #7 in the US & also Nokomis & Venice High as well. **Located Near 2 Beaches. **NEW Tile Roof in 2017.**
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.

Home Highlights

Parking
Garage
Outdoor
Porch, Patio, Deck, Pool
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 217 Windward Dr

Interior Features

Heating & Cooling
Heating: Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet
Interior Details
Number of Rooms: 7Types of Rooms: Walk In Closet, Dining RoomWet BarCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: TileDeckExterior: StuccoFoundation Type: ConcretePatioPorch
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1985Year Updated: 1990
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 0.30 acres

Building

Community rooms
Fitness Center
Fitness & Sports
Tennis Court

Price History for 217 Windward Dr

DatePriceEventSource
02/07/2018$635,000Sold
N/A
11/16/2017$662,900Listed For SaleAgent Provided
02/23/2017$470,000Sold
N/A
01/30/2017$500,000PendingAgent Provided
01/04/2017$500,000PendingToActiveAgent Provided
01/03/2017$500,000PendingAgent Provided
12/05/2016$500,000PriceChange
Agent Provided
11/15/2016$549,000Listed For SaleAgent Provided

Market trends in Osprey

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$600K
$73.33KMoM
Sale-to-List Price
94.4%
0.3%MoM
Price per sq ft
$277
$29MoM
Available listings
162
1MoM
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Property Tax and Assessment

Year2025
Tax$10,113
Assessment$807,400
Home facts updated by county records

Comparable Sales for 217 Windward Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
216 Windward Dr, Osprey, FL
0.03
Single-Family Home
$600,000
11/18/25
3
3
2,575
1235 Yacht Harbor Dr, Osprey, FL
0.07
Single-Family Home
$1,065,000
02/20/26
3
3
2,698
1218 Yacht Harbor Dr, Osprey, FL
0.09
Single-Family Home
$1,025,000
04/24/26
3
3
3,297
102 Windward Dr, Osprey, FL
0.18
Single-Family Home
$565,000
06/04/26
3
2.5
2,134
1212 Windward Dr, Osprey, FL
0.17
Single-Family Home
$645,000
08/25/25
3
2
1,994
1426 Landview Ln, Osprey, FL
0.42
Single-Family Home
$670,000
06/10/25
4
3
2,513
447 Oak Point Rd, Osprey, FL
0.23
Single-Family Home
$520,000
12/30/25
4
3
2,688
142 Dory Ln, Osprey, FL
0.14
Single-Family Home
$1,050,000
07/22/25
3
2
2,531
238 Lookout Point Dr, Osprey, FL
0.48
Single-Family Home
$800,000
05/01/26
3
2.5
2,676
432 Yacht Harbor Dr, Osprey, FL
0.24
Single-Family Home
$1,075,000
05/19/26
3
2.5
2,125

Nearby homes

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Assigned Schools

These are the assigned schools for 217 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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217 Windward Dr, Osprey, FL 34229 is a 4 bedroom, 3 bathroom, 2,552 sqft single-family home built in 1985. This property is not currently available for sale. 217 Windward Dr was last sold on Feb 7, 2018 for $635,000. The current Trulia Estimate for 217 Windward Dr is $998,600.