1375 Windward Dr, Osprey, FL 34229
OFF MARKET

$901,300

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,673 sqft (on 0.26 acres)

1375 Windward Dr, Osprey, FL 34229

Est. Refi. Payment $5,586/mo*
Refinance Your Home
Currently Off Market - Sold Jul 25, 2002 for $474,500

Home Value

Trulia Estimate
$901K
Since last month
Increased$5K (+0.6%)
Since last year
Decreased$8K (-0.8%)
Since last sale
Increased$431K (+90.8%)
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 +69% in the last 10 years
MonthEstimated value
2026
August 2026$906K
July 2026$900K
June 2026$912K
May 2026$919K
April 2026$926K
March 2026$923K
February 2026$931K
January 2026$914K
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
102 WINDWARD DRIVE, Osprey, FL
0.24
Single-Family Home
$565,000
06/04/26
3
2.5
2,134
216 WINDWARD DRIVE, Osprey, FL
0.35
Single-Family Home
$600,000
11/18/25
3
3
2,575
1471 SHOAL WAY, Osprey, FL
0.12
Single-Family Home
$1,265,000
06/01/26
4
3
2,798
1602 SOUTHBAY DRIVE, Osprey, FL
0.21
Single-Family Home
$925,000
07/15/26
4
3.5
2,980
1484 SEAFARER DRIVE, Osprey, FL
0.15
Single-Family Home
$1,200,000
10/24/25
4
3.5
3,479
238 Lookout Point Dr, Osprey, FL
0.33
Single-Family Home
$800,000
05/01/26
3
2.5
2,676
1313 THORNAPPLE DRIVE, Osprey, FL
0.30
Single-Family Home
$525,000
12/04/25
3
3
2,082
1319 Thornapple Dr, Osprey, FL
0.33
Single-Family Home
$290,500
09/16/25
4
3.5
3,067
114 Windward Dr, Osprey, FL
0.24
Single-Family Home
$585,000
06/02/26
3
2
2,037
186 WINDWARD DRIVE, Osprey, FL
0.31
Single-Family Home
$565,000
07/20/26
3
2
2,505

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
146 YACHT HARBOR DRIVE, Osprey, FL 34229
0.10
$943,000
3
2.5
2,627
Off Market
1426 LANDVIEW LANE, Osprey, FL 34229
0.09
$645,800
4
3
2,513
Off Market
1471 SHOAL WAY, Osprey, FL 34229
0.12
$1,265,000
4
3
2,798
Recently Sold
128 SEA ANCHOR DRIVE, Osprey, FL 34229
0.14
$899,100
3
3
2,677
Off Market
1321 SOUTHBAY DRIVE, Osprey, FL 34229
0.15
$985,100
3
2.5
2,968
Off Market
1484 SEAFARER DRIVE, Osprey, FL 34229
0.15
$1,182,000
4
3.5
3,479
Off Market
1251 WINDWARD DRIVE, Osprey, FL 34229
0.15
$838,400
3
2
2,015
Off Market
1486 LANDVIEW LANE, Osprey, FL 34229
0.16
$817,000
3
2
1,869
Recently Sold
172 SEA ANCHOR DRIVE, Osprey, FL 34229
0.18
$843,200
3
3
2,283
Off Market
206 Four Knot LN, Osprey, FL 34229
0.19
$1,775,000
3
2
2,411
For Sale
1495 LANDVIEW LANE, Osprey, FL 34229
0.19
$760,000
3
2
2,474
For Sale
142 DORY LANE, Osprey, FL 34229
0.21
$1,020,800
3
2
2,531
Off Market

Local Information

  • Map ViewExplore the area around 1375 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
2002
Lot Size
0.26 acres
Living Area
2,673 sqft
Price/Sqft
$337
Parking
Garage

About this House

This single-family home is located at 1375 Windward Dr, Osprey, FL. 1375 Windward Dr is in Osprey, FL and in ZIP code 34229. This property has 4 bedrooms, 3 bathrooms and approximately 2,673 sqft of floor space. This property has a lot size of 0.26 acres and was built in 2002.
1375 Windward Dr, Osprey, FL 34229 is a 4 bedroom, 3 bathroom, 2,673 sqft single-family home built in 2002. It last sold for $474,500 on Jul 25, 2002. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $901,300, with a rent estimate of $4,974/month.

Home Details for 1375 Windward Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Other
Interior Details
Number of Rooms: 9
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: 2002Year Updated: 2002
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.26 acres

Price and Tax history

DateEventPrice
Jul 25, 2002
Source: N/A
Sold
$474,500

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 1375 Windward Dr

  • What is 1375 Windward Dr estimated to be worth?
    Trulia's estimated value for 1375 Windward Dr in Osprey, FL is $901,300.
  • What is the price history for 1375 Windward Dr?
    1375 Windward Dr in Osprey, FL last sold for $474,500 in July 2002.
  • 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 1375 Windward Dr have a pool?
    Yes, 1375 Windward Dr in Osprey, FL has a pool.
  • How big is the lot at 1375 Windward Dr?
    The lot at 1375 Windward Dr in Osprey, FL is about 0.26 acres (11,456 sq ft).

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