1325 Windward Dr, Osprey, FL 34229
OFF MARKET

1325 Windward Dr
Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,374 sqft (on 1 acre)

$860,000

Trulia Estimate
as of Jun 12, 2026
Est. Refi. Payment $5,257/mo*
Refinance Your Home

$860,000

Trulia Estimate
as of Jun 12, 2026
Est. Refi. Payment $5,257/mo*
Refinance Your Home
4 Beds
3 Baths
2,374 sqft
(on 1 acre)

Local Information

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

Description

Dock your boat at the deepwater protected harbor basin of the Southbay Yacht And Racquet Club and walk home to your completely remodeled 4 bed 3 bath home in this remarkable centrally located development. If it all about the lifestyle this home has it all. The gourmet kitchen boasts a brand new stainless steel appliance package with vented hood and Quartz counter tops with all wood cabinets. The owners retreat has a master bath that includes an oversized Jacuzzi tub. The split floor plan offers
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
Patio, Pool
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 1325 Windward Dr

Interior Features

Heating & Cooling
Heating: OtherAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1Floors: Carpet
Interior Details
Number of Rooms: 7

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: 2007
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 1 acre

Price History for 1325 Windward Dr

DatePriceEventSource
03/01/2011$415,000Sold
N/A
09/17/2010$499,000Listed For SaleAgent Provided
08/13/2010$499,000ListingRemovedAgent Provided
07/03/2010$499,000Listed For SaleAgent Provided
04/26/2010$345,000Sold
N/A
03/09/2010$339,900Listed For SaleAgent Provided
12/12/2006$567,500Sold
N/A

Market trends in Osprey

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$569K
$30.33KMoM
Sale-to-List Price
—
Price per sq ft
$269
$8MoM
Available listings
156
6MoM
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Property Tax and Assessment

Year2025
Tax$5,662
Assessment$687,200
Home facts updated by county records

Homeowner tools

Estimated monthly rent$5,148/mo
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Homes for rent near 1325 Windward Dr

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Comparable Sales for 1325 Windward Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
102 Windward Dr, Osprey, FL
0.19
Single-Family Home
$565,000
06/04/26
3
2.5
2,134
1471 Shoal Way, Osprey, FL
0.17
Single-Family Home
$1,265,000
06/01/26
4
3
2,798
216 Windward Dr, Osprey, FL
0.31
Single-Family Home
$600,000
11/18/25
3
3
2,575
1212 Windward Dr, Osprey, FL
0.16
Single-Family Home
$645,000
08/25/25
3
2
1,994
1313 Thornapple Dr, Osprey, FL
0.29
Single-Family Home
$525,000
12/04/25
3
3
2,082
518 Luminary Blvd, Osprey, FL
0.38
Single-Family Home
$720,000
06/16/25
4
3
2,320
1319 Thornapple Dr, Osprey, FL
0.31
Single-Family Home
$290,500
09/16/25
4
3.5
3,067
523 Habitat Blvd, Osprey, FL
0.38
Single-Family Home
$750,000
12/30/25
4
3
2,314
522 Luminary Blvd, Osprey, FL
0.39
Single-Family Home
$600,000
05/26/26
3
3
2,320
238 Lookout Point Dr, Osprey, FL
0.37
Single-Family Home
$800,000
05/01/26
3
2.5
2,676

Nearby homes

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Assigned Schools

These are the assigned schools for 1325 Windward Dr.
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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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Homes for sale near 1325 Windward Dr

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Off Market Homes Near 1325 Windward Dr

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1325 Windward Dr, Osprey, FL 34229 is a 4 bedroom, 3 bathroom, 2,374 sqft single-family home built in 2002. This property is not currently available for sale. 1325 Windward Dr was last sold on Mar 1, 2011 for $415,000. The current Trulia Estimate for 1325 Windward Dr is $860,000.