217 Windward Dr, Osprey, FL 34229
Property image
Property image
OFF MARKET

$997,600

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

217 Windward Dr, Osprey, FL 34229

Est. Refi. Payment $6,181/mo*
Refinance Your Home
Currently Off Market - Sold Feb 7, 2018 for $635,000

Home Value

Trulia Estimate
$998K
Since last month
Increased$22K (+2.2%)
Since last year
Decreased$4K (-0.4%)
Since last sale
Increased$368K (+58%)
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 +104% in the last 10 years
MonthEstimated value
2026
August 2026$1M
August 2026$1M
July 2026$982K
June 2026$1.03M
May 2026$1M
April 2026$1.02M
March 2026$1.01M
February 2026$1.02M
January 2026$993K
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
0.03
Single-Family Home
$600,000
11/18/25
3
3
2,575
204 WINDWARD DRIVE, Osprey, FL
0.04
Single-Family Home
$800,000
08/24/26
3
3
2,486
186 WINDWARD DRIVE, Osprey, FL
0.07
Single-Family Home
$565,000
07/20/26
3
2
2,505
1235 YACHT HARBOR DRIVE, Osprey, FL
0.07
Single-Family Home
$1,065,000
02/20/26
3
3
2,698
1218 YACHT HARBOR DRIVE, Osprey, FL
0.09
Single-Family Home
$1,025,000
04/24/26
3
3
3,297
102 WINDWARD DRIVE, Osprey, FL
0.18
Single-Family Home
$565,000
06/04/26
3
2.5
2,134
114 Windward Dr, Osprey, FL
0.16
Single-Family Home
$585,000
06/02/26
3
2
2,037
408 YACHT HARBOR DRIVE, Osprey, FL
0.23
Single-Family Home
$1,250,000
06/15/26
4
4
2,624
447 OAK POINT ROAD, Osprey, FL
0.23
Single-Family Home
$520,000
12/30/25
4
3
2,688
486 YACHT HARBOR DRIVE, Osprey, FL
0.15
Single-Family Home
$1,325,000
08/25/26
3
3.5
2,939

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
0.03
$600,000
3
3
2,575
Recently Sold
204 WINDWARD DRIVE, Osprey, FL 34229
0.04
$800,000
3
3
2,486
Recently Sold
1237 FLYING BRIDGE LANE, Osprey, FL 34229
0.05
$842,800
3
2
2,045
Off Market
186 WINDWARD DRIVE, Osprey, FL 34229
0.07
$565,000
3
2
2,505
Recently Sold
188 DORY LANE, Osprey, FL 34229
0.07
$784,900
3
2
2,069
Off Market
1235 YACHT HARBOR DRIVE, Osprey, FL 34229
0.07
$1,065,000
3
3
2,698
Recently Sold
1218 YACHT HARBOR DRIVE, Osprey, FL 34229
0.09
$1,025,000
3
3
3,297
Recently Sold
142 DORY LANE, Osprey, FL 34229
0.14
$1,024,900
3
2
2,531
Off Market
360 PINE RUN DRIVE, Osprey, FL 34229
0.17
$255,100
2
2
1,379
Off Market
362 PINE RUN DRIVE, Osprey, FL 34229
0.17
$215,000
2
2
1,224
Recently Sold
750 PINE RUN DRIVE, Osprey, FL 34229
0.17
$125,700
1
1
586
Off Market
756 PINE RUN DRIVE, Osprey, FL 34229
0.17
$259,900
2
2
1,224
Off Market

Local Information

  • Map ViewExplore the area around 217 Windward Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1985
Lot Size
0.3 acres
Living Area
2,552 sqft
Price/Sqft
$391
Parking
Garage

About this House

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.**
217 Windward Dr, Osprey, FL 34229 is a 4 bedroom, 3 bathroom, 2,552 sqft single-family home built in 1985. It last sold for $635,000 on Feb 7, 2018. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $997,600, with a rent estimate of $4,891/month.

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 and Tax history

DateEventPrice
Feb 7, 2018
Source: N/A
Sold
$635,000
Nov 16, 2017
Source: Agent Provided
Listed For Sale
$662,900
Feb 23, 2017
Source: N/A
Sold
$470,000
Jan 30, 2017
Source: Agent Provided
Pending
$500,000
Jan 4, 2017
Source: Agent Provided
PendingToActive
$500,000

Market trends in Osprey

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
133
7MoM

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 217 Windward Dr

  • What is 217 Windward Dr estimated to be worth?
    Trulia's estimated value for 217 Windward Dr in Osprey, FL is $997,600.
  • What is the price history for 217 Windward Dr?
    217 Windward Dr in Osprey, FL last sold for $635,000 in February 2018.
  • Is Osprey a buyer's or seller's market?
    Osprey is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Osprey?
    Residents describe Osprey, FL as dog-friendly, quiet, and easy to park in. Most residents say you need a car. See recently sold homes in Osprey, FL.
  • Does 217 Windward Dr have air conditioning?
    Yes, 217 Windward Dr in Osprey, FL has air conditioning.
  • Does 217 Windward Dr have a pool?
    Yes, 217 Windward Dr in Osprey, FL has a pool.

Explore by feature - Pet Friendly

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