1263 Windward Dr, Osprey, FL 34229
OFF MARKET

1263 Windward Dr
Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,058 sqft (on 0.29 acres)

$787,200

Trulia Estimate
as of Jun 30, 2026
Est. Refi. Payment $4,765/mo*
Refinance Your Home

$787,200

Trulia Estimate
as of Jun 30, 2026
Est. Refi. Payment $4,765/mo*
Refinance Your Home
3 Beds
2 Baths
2,058 sqft
(on 0.29 acres)

Local Information

  • Map ViewExplore the area around 1263 Windward Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

BEAUTIFULLY RENOVATED! This stunning, immaculate home is located in the highly desirable Southbay Yacht and RacquetClub. Featuring an open-concept living room, dining room, and kitchen combination, this is a great house for entertaining or relaxing around the sparkling pool. The main living space has beautiful, easy to maintain, travertine floors. The kitchen has granitecountertops and high-end all-wood cabinets. Two pantries with pull-out shelves, large under-cabinet drawers, and lighted corner display cabinets provide an unbelievable amount of storage space. The oversized island features base cabinets on two sides and accommodates four stools. All appliances are less than five years old, including refrigerator, dishwasher, electronic range, chrome/glass range hood, and a drawer microwave. The split-bedroom floorplan offers a private master bedroom with two walk-in closets and en suite bath with new porcelain tile, spa-like shower, plentiful cabinets and linencloset. The third bedroom, which also can be an office, has double pocket doors and contains a Murphy bed for additional sleeping accommodations. The second bathroom also serves as a convenient pool bath. The oversized lanai, caged pool, and private back yard are ideal for family activities. The extra large garage features abundant built-instorage and room for a workshop. Southbay is a friendly community that includes a marina, clubhouse, pool, tennis and pickle-ball courts, and numerous walking paths. Truly paradise found!
1263 Windward Dr, Osprey, FL 34229 is a 3 bedroom, 2 bathroom, 2,058 sqft single-family home built in 1985. It last sold for $475,000 on Sep 3, 2019. More recently, it was listed as a rental in January 2018 with an asking price of $2,650 per month. That rental listing was removed on June 12, 2018. It is currently off market. The Trulia Estimate is $787,200, with a rent estimate of $3,829/month.

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 1263 Windward Dr

Interior Features

Heating & Cooling
Heating: Central, ElectricAir ConditioningCooling System: CentralHeating Fuel: Central
Interior Details
Number of Rooms: 6Types of Rooms: Walk In Closet, Dining Room
Appliances & Utilities
DishwasherDisposalDryerRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Tile, Carpet

Exterior Features

Exterior Home Features
Roof: OtherExterior: StuccoFoundation Type: ConcretePatio
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage, Open

Property Information

Year Built
Year Built: 1985Year Updated: 1995
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.29 acres

Price History for 1263 Windward Dr

DatePriceEventSource
09/03/2019$475,000Sold
N/A
08/16/2019$479,000PendingAgent Provided
08/14/2019$479,000Listed For SaleAgent Provided
06/12/2018$2,595ListingRemovedAgent Provided
05/12/2018$2,595PriceChange
Agent Provided
01/30/2018$2,650Listed For RentAgent Provided
10/12/2017$2,650ListingRemovedAgent Provided
03/06/2017$2,650PriceChange
Agent Provided
03/04/2017$2,500Listed For RentAgent Provided
04/30/2016$2,500ListingRemovedAgent Provided
08/08/2015$2,500Listed For RentAgent Provided
04/08/2014$1,995ListingRemovedAgent Provided
11/24/2013$1,995Listed For RentAgent Provided
06/16/2013$1,950ListingRemovedAgent Provided
06/02/2013$1,950PriceChange
Agent Provided
05/11/2013$1,995PriceChange
Agent Provided
04/16/2013$1,997Listed For RentAgent Provided
04/10/2013$314,500Sold
N/A
03/05/2013$314,500PendingAgent Provided
02/28/2013$314,500Listed For SaleAgent Provided

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$5,859
Assessment$658,900
Home facts updated by county records

Comparable Sales for 1263 Windward Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
114 Windward Dr, Osprey, FL
0.12
Single-Family Home
$585,000
06/02/26
3
2
2,037
1212 Windward Dr, Osprey, FL
0.09
Single-Family Home
$645,000
08/25/25
3
2
1,994
102 Windward Dr, Osprey, FL
0.11
Single-Family Home
$565,000
06/04/26
3
2.5
2,134
142 Dory Ln, Osprey, FL
0.10
Single-Family Home
$1,050,000
07/22/25
3
2
2,531
216 Windward Dr, Osprey, FL
0.25
Single-Family Home
$600,000
11/18/25
3
3
2,575
1486 Landview Ln, Osprey, FL
0.29
Single-Family Home
$817,000
06/30/26
3
2
1,869
1303 Thornapple Dr, Osprey, FL
0.31
Single-Family Home
$654,000
04/16/26
3
2
1,929
510 Latitude Ln, Osprey, FL
0.39
Single-Family Home
$550,000
03/23/26
3
2
2,298
1337 Copperwood Dr, Osprey, FL
0.36
Single-Family Home
$520,000
06/17/26
3
2
2,172
1313 Thornapple Dr, Osprey, FL
0.29
Single-Family Home
$525,000
12/04/25
3
3
2,082

Nearby homes

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Assigned Schools

These are the assigned schools for 1263 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

  • 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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Apartments for Rent

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Explore by feature - Pet Friendly

9 pet-friendly rentals in Osprey, FL

Explore by feature - Garage

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Explore by feature - Pool

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Homes for sale near 1263 Windward Dr

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Off Market Homes Near 1263 Windward Dr

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