1339 Windward Dr, Osprey, FL 34229
Property image
Property image
OFF MARKET

$855,900

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 2,936 sqft (on 0.26 acres)

1339 Windward Dr, Osprey, FL 34229

Est. Refi. Payment $5,427/mo*
Refinance Your Home
Currently Off Market - Sold Jul 25, 2001 for $120,000

Home Value

Trulia Estimate
$856K
Since last month
Decreased$2K (-0.3%)
Since last year
Increased$17K (+2%)
Since last sale
Increased$738K (+614.7%)
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 +52% in the last 10 years
MonthEstimated value
2026
August 2026$858K
August 2026$856K
July 2026$860K
June 2026$868K
May 2026$876K
April 2026$885K
March 2026$884K
February 2026$893K
January 2026$888K
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
1319 Thornapple Dr, Osprey, FL
0.32
Single-Family Home
$290,500
09/16/25
4
3.5
3,067
1474 LANDVIEW LANE, Osprey, FL
0.18
Single-Family Home
$1,450,000
09/01/26
4
3
3,246
1471 SHOAL WAY, Osprey, FL
0.15
Single-Family Home
$1,265,000
06/01/26
4
3
2,798
1484 SEAFARER DRIVE, Osprey, FL
0.18
Single-Family Home
$1,200,000
10/24/25
4
3.5
3,479
114 Windward Dr, Osprey, FL
0.21
Single-Family Home
$585,000
06/02/26
3
2
2,037
1602 SOUTHBAY DRIVE, Osprey, FL
0.24
Single-Family Home
$925,000
07/15/26
4
3.5
2,980
186 WINDWARD DRIVE, Osprey, FL
0.28
Single-Family Home
$565,000
07/20/26
3
2
2,505
102 WINDWARD DRIVE, Osprey, FL
0.20
Single-Family Home
$565,000
06/04/26
3
2.5
2,134
216 WINDWARD DRIVE, Osprey, FL
0.32
Single-Family Home
$600,000
11/18/25
3
3
2,575
1486 LANDVIEW LANE, Osprey, FL
0.19
Single-Family Home
$817,000
06/30/26
3
2
1,869

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
0.11
$833,700
3
2
2,015
Off Market
146 YACHT HARBOR DRIVE, Osprey, FL 34229
0.09
$951,800
3
2.5
2,627
Off Market
128 SEA ANCHOR DRIVE, Osprey, FL 34229
0.11
$903,400
3
3
2,677
Off Market
1426 LANDVIEW LANE, Osprey, FL 34229
0.11
$648,500
4
3
2,513
Off Market
1321 SOUTHBAY DRIVE, Osprey, FL 34229
0.14
$988,900
3
2.5
2,968
Off Market
1212 WINDWARD DRIVE, Osprey, FL 34229
0.18
$633,300
3
2
1,994
Off Market
142 DORY LANE, Osprey, FL 34229
0.18
$1,024,900
3
2
2,531
Off Market
172 SEA ANCHOR DRIVE, Osprey, FL 34229
0.17
$843,200
3
3
2,283
Off Market
102 WINDWARD DRIVE, Osprey, FL 34229
0.20
$565,000
3
2.5
2,134
Recently Sold
1471 SHOAL WAY, Osprey, FL 34229
0.15
$1,265,000
4
3
2,798
Recently Sold
1474 LANDVIEW LANE, Osprey, FL 34229
0.18
$1,450,000
4
3
3,246
Recently Sold
139 WOODLAND PLACE #139, Osprey, FL 34229
0.24
$235,000
1
1.5
865
Recently Sold

Local Information

  • Map ViewExplore the area around 1339 Windward Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2006
0.26 acre lot
2,936 sqft
$292/sqft
Garage

About this House

Property ia available again! There is fantastic value to be found in this custom built Arthur Rutenberg Home in the waterfront community of Southbay Yacht and Racquet Club!! One of the newest homes in the Southbay community, this outstanding property is being offered fully furnished and turnkey. Soaring ceilings, outdoor living space, and outstanding designer features make this home a prime property in today's market. Enjoy the spacious lanai, the expansive master suite with two walk-in closets, the designer kitchen, and an abundance of detailed features found throughout the home. The well-designed floor plan is large enough for gatherings of family and friends, yet provides just the right sized spaces for individual family members. In addition, a formal dining room for special occasions, an office/den for work or quiet time, and a split floor design help to meet the needs of each and every family configuration. Southbay Yacht and Racquet Club features one of the best marinas on the ICW with boat slips accommodating up to 60-foot boats. Slips are available only to Southbay homeowners at a very low monthly fee. The association also offers an active lifestyle with tennis courts, pickleball courts, exercise room, walking paths, kayak storage, playground, and a park on the shoreline of the Intracoastal Waterway. Southbay is a boater's paradise and has long been the most sought after boating association in the Greater Sarasota area. Take this opportunity to enjoy all that Florida has to offer.
1339 Windward Dr, Osprey, FL 34229 is a 4 bedroom, 3 bathroom, 2,936 sqft single-family home built in 2006. It last sold for $120,000 on Jul 25, 2001. More recently, it was listed as a rental in September 2013 with an asking price of $2,500 per month. That rental listing was removed on November 30, 2013. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $855,900, with a rent estimate of $3,859/month.

Home Details for 1339 Windward Dr

Exterior Features

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

Property Information

Year Built
Year Built: 2006Year Updated: 2006
Property Type / Style
Property Type: Single Family Home

Interior Features

Interior Details
Number of Rooms: 6Types of Rooms: Walk In Closet
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Heating & Cooling
Air ConditioningCooling System: Central
Levels, Entrance, & Accessibility
Floors: Tile, Carpet

Community

Units in Building: 1

Lot Information

Lot Area: 0.26 acres

Price and Tax history

DateEventPrice
Aug 11, 2018
Source: Agent Provided
ListingRemoved
$795,000
Jun 3, 2018
Source: Agent Provided
Listed For Sale
$795,000
Mar 24, 2018
Source: Agent Provided
ListingRemoved
$795,000
Mar 10, 2018
Source: Agent Provided
Listed For Sale
$795,000
Nov 30, 2013
Source: N/A
ListingRemoved
$2,500

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 1339 Windward Dr

  • What is 1339 Windward Dr estimated to be worth?
    Trulia's estimated value for 1339 Windward Dr in Osprey, FL is $855,900.
  • What is the price history for 1339 Windward Dr?
    1339 Windward Dr in Osprey, FL last sold for $120,000 in July 2001.
  • 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 1339 Windward Dr have air conditioning?
    Yes, 1339 Windward Dr in Osprey, FL has air conditioning.
  • Does 1339 Windward Dr have laundry facilities?
    Yes, 1339 Windward Dr in Osprey, FL has in-unit laundry.

Explore by feature - Pet Friendly

9 pet-friendly rentals in Osprey, FL

Explore by feature - Garage

19 rentals with a garage in Osprey, FL

Explore by feature - Air Conditioning

29 rentals with air conditioning in Osprey, FL

Explore by feature - Pool

22 rentals with a pool in Osprey, FL

Explore by feature - Washer/dryer

29 rentals with a washer/dryer in Osprey, FL

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 1339 Windward Dr

Skip to last item
Skip to first item

Homes for sale near 1339 Windward Dr

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item