1317 Windward Dr, Osprey, FL 34229
OFF MARKET

$900,000

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 2,864 sqft (on 0.28 acres)

1317 Windward Dr, Osprey, FL 34229

Est. Refi. Payment $5,804/mo*
Refinance Your Home
Currently Off Market - Sold Jan 25, 2021 for $650,000

Home Value

Trulia Estimate
$900K
Since last month
Increased$12K (+1.4%)
Since last year
Increased$19K (+2.1%)
Since last sale
Increased$254K (+39.1%)
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 +51% in the last 10 years
MonthEstimated value
2026
September 2026$904K
August 2026$893K
July 2026$892K
June 2026$909K
May 2026$903K
April 2026$917K
March 2026$918K
February 2026$915K
January 2026$902K
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
0.29
Single-Family Home
$600,000
11/18/25
3
3
2,575
102 WINDWARD DRIVE, Osprey, FL
0.16
Single-Family Home
$565,000
06/04/26
3
2.5
2,134
204 WINDWARD DRIVE, Osprey, FL
0.27
Single-Family Home
$800,000
08/24/26
3
3
2,486
114 Windward Dr, Osprey, FL
0.17
Single-Family Home
$585,000
06/02/26
3
2
2,037
238 Lookout Point Dr, Osprey, FL
0.38
Single-Family Home
$800,000
05/01/26
3
2.5
2,676
186 WINDWARD DRIVE, Osprey, FL
0.24
Single-Family Home
$565,000
07/20/26
3
2
2,505
1235 YACHT HARBOR DRIVE, Osprey, FL
0.31
Single-Family Home
$1,065,000
02/20/26
3
3
2,698
529 HABITAT BOULEVARD, Osprey, FL
0.42
Single-Family Home
$799,000
03/09/26
3
3
2,617
219 KEEL WAY, Osprey, FL
0.35
Single-Family Home
$1,100,000
04/30/26
3
2.5
2,735
1218 YACHT HARBOR DRIVE, Osprey, FL
0.36
Single-Family Home
$1,025,000
04/24/26
3
3
3,297

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
1251 WINDWARD DRIVE, Osprey, FL 34229
0.07
$845,500
3
2
2,015
Off Market
146 YACHT HARBOR DRIVE, Osprey, FL 34229
0.09
$961,900
3
2.5
2,627
Off Market
128 SEA ANCHOR DRIVE, Osprey, FL 34229
0.08
$903,400
3
3
2,677
Off Market
1426 LANDVIEW LANE, Osprey, FL 34229
0.15
$648,500
4
3
2,513
Off Market
1417 LANDVIEW LANE, Osprey, FL 34229
0.15
$1,399,000
4
4
3,255
For Sale
1321 SOUTHBAY DRIVE, Osprey, FL 34229
0.15
$980,300
3
2.5
2,968
Off Market
1212 WINDWARD DRIVE, Osprey, FL 34229
0.14
$635,300
3
2
1,994
Off Market
142 DORY LANE, Osprey, FL 34229
0.14
$1,028,100
3
2
2,531
Off Market
172 SEA ANCHOR DRIVE, Osprey, FL 34229
0.15
$843,200
3
3
2,283
Off Market
102 WINDWARD DRIVE, Osprey, FL 34229
0.16
$565,000
3
2.5
2,134
Recently Sold
1471 SHOAL WAY, Osprey, FL 34229
0.20
$1,265,000
4
3
2,798
Recently Sold
1474 LANDVIEW LANE, Osprey, FL 34229
0.22
$1,450,000
4
3
3,246
Recently Sold

Local Information

  • Map ViewExplore the area around 1317 Windward Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1993
0.28 acre lot
2,864 sqft
$314/sqft
Garage

About this House

THIS PROPERTY WAS CUSTOM DESIGNED AND BUILT BY CURRENT OWNER WITH NO DETAIL OMMITTED. VOLUME CEILINGS THRU-OUT WITH TRANSOM GLASS ABOVE MOST DOORS AND WINDOWS. THIS IS A VERY OPEN PLAN WITH GREATROOM, KITCHEN AND DINING THE MAIN CORE. EXTREMELY LARGE MASTER BEDROOM WITH TWO WALK-IN CLOSETS AND BUILT INS AND HUGH MASTER BATH LEADING TO HEATED POOL AREA. KITCHEN FEATURES AN ISLAND COOKING AREA WITH CUSTOM CABINETS ON THREE WALLS LEADING TO 9X11 UTILITY ROOM WITH SEWING AND COMPUTER DESKS. THIS ONE OF KIND SOUTHBAY HOME STANDS OUT ON IT'S OWN WITH FEATURES NOT NORMALLY FOUND IN THIS WATERFRONT COMMUNITY.
1317 Windward Dr, Osprey, FL 34229 is a 3 bedroom, 3 bathroom, 2,864 sqft single-family home built in 1993. It last sold for $650,000 on Jan 25, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $900,000, with a rent estimate of $4,721/month.

Home Details for 1317 Windward Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Other
Interior Details
Number of Rooms: 6
Heating & Cooling
Air Conditioning

Exterior Features

Exterior Home Features
Roof: OtherExterior: StuccoFoundation Type: ConcretePatio
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1993Year Updated: 2003
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.28 acres

Price and Tax history

DateEventPrice
Jan 25, 2021
Source: N/A
Sold
$650,000
Oct 31, 2012
Source: N/A
Sold
$443,500
Jul 20, 2012
Source: Agent Provided
Listed For Sale
$479,000

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 1317 Windward Dr

  • What is 1317 Windward Dr estimated to be worth?
    Trulia's estimated value for 1317 Windward Dr in Osprey, FL is $900,000.
  • What is the price history for 1317 Windward Dr?
    1317 Windward Dr in Osprey, FL last sold for $650,000 in January 2021.
  • 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 1317 Windward Dr have a pool?
    Yes, 1317 Windward Dr in Osprey, FL has a pool.
  • How big is the lot at 1317 Windward Dr?
    The lot at 1317 Windward Dr in Osprey, FL is about 0.28 acres (12,150 sq ft).

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