1305 Windward Dr, Osprey, FL 34229
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Property image
OFF MARKET

1305 Windward Dr
Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,748 sqft (on 0.26 acres)

$938,500

Trulia Estimate
as of Jul 19, 2026
Est. Refi. Payment $5,779/mo*
Refinance Your Home

$938,500

Trulia Estimate
as of Jul 19, 2026
Est. Refi. Payment $5,779/mo*
Refinance Your Home
4 Beds
3 Baths
2,748 sqft
(on 0.26 acres)

Local Information

  • Map ViewExplore the area around 1305 Windward Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Situated in the quiet subdivision of South Bay Yacht and Racquet Club. Enjoy the tennis and the South Bay Marina.This property has 4403 gross Square Feet, with 4 Bedrooms and 3 full baths. There is one bedroom that can be used as a guest suite/ study surrounded by the pool, waterfalls and jetted tub. All located on a large screened lanai.This area can be viewed from the inside of the dwelling and adjacent to the 3 car garage. Asking $565,000. Don''t miss out on this one!
1305 Windward Dr, Osprey, FL 34229 is a 4 bedroom, 3 bathroom, 2,748 sqft single-family home built in 1997. It last sold for $525,000 on Jan 12, 2017. It is currently off market. The Trulia Estimate is $938,500, with a rent estimate of $5,724/month.

Home Highlights

Parking
Garage
Outdoor
Porch, Patio, Deck, Pool
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 1305 Windward Dr

Interior Features

Heating & Cooling
Heating: Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile
Interior Details
Number of Rooms: 8Types of Rooms: Walk In ClosetCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Hot Tub or Spa

Exterior Features

Exterior Home Features
Roof: TileDeckExterior: StuccoFoundation Type: ConcretePatioPorch
Pool
Pool
Parking & Garage
GarageParking: Carport, Garage Attached

Property Information

Year Built
Year Built: 1997Year Updated: 1997
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.26 acres

Building

Fitness & Sports
Tennis Court

Price History for 1305 Windward Dr

DatePriceEventSource
01/12/2017$525,000Sold
N/A
11/30/2016$565,000Listed For SaleAgent Provided
11/19/1997$195,000Sold
N/A
01/03/1997$96,000Sold
N/A

Market trends in Osprey

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
139
17MoM
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Property Tax and Assessment

Year2025
Tax$9,753
Assessment$805,900
Home facts updated by county records

Comparable Sales for 1305 Windward Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
102 Windward Dr, Osprey, FL
0.14
Single-Family Home
$565,000
06/04/26
3
2.5
2,134
216 Windward Dr, Osprey, FL
0.27
Single-Family Home
$600,000
11/18/25
3
3
2,575
114 Windward Dr, Osprey, FL
0.15
Single-Family Home
$585,000
06/02/26
3
2
2,037
1212 Windward Dr, Osprey, FL
0.12
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
142 Dory Ln, Osprey, FL
0.13
Single-Family Home
$1,050,000
07/22/25
3
2
2,531
1471 Shoal Way, Osprey, FL
0.21
Single-Family Home
$1,265,000
06/01/26
4
3
2,798
1235 Yacht Harbor Dr, Osprey, FL
0.30
Single-Family Home
$1,065,000
02/20/26
3
3
2,698
1319 Thornapple Dr, Osprey, FL
0.31
Single-Family Home
$290,500
09/16/25
4
3.5
3,067
1602 Southbay Dr, Osprey, FL
0.30
Single-Family Home
$925,000
07/15/26
4
3.5
2,980

Nearby homes

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Assigned Schools

These are the assigned schools for 1305 Windward Dr.
View nearby schools on GreatSchools
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

  • 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 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 1305 Windward Dr

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Off Market Homes Near 1305 Windward Dr

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