1275 Windward Dr, Osprey, FL 34229
Bedroom 3
Exterior
OFF MARKET

1275 Windward Dr
Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,981 sqft (on 0.29 acres)

$748,900

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $4,616/mo*
Refinance Your Home

$748,900

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $4,616/mo*
Refinance Your Home
3 Beds
2 Baths
1,981 sqft
(on 0.29 acres)

Local Information

  • Map ViewExplore the area around 1275 Windward Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Immaculately renovated (2016-2018) pool home. Not in a flood zone. Located in the desirable Southbay Yacht & Racquet Club! Call 401-835-3887 for a private showing.

Brand new expansive custom kitchen with gorgeous quartz counter-tops, center island, stainless steel appliances and farmers sink.

New standing seam metal roof and custom aluminum chimney cap, new high impact (hurricane-impact) windows, sliders, and doors!

Baths renovated and updated with granite and quartzite, all new plumbing (replumbed) throughout. New washer and dryer, top of their class in 2017. All new custom interior doors with extra touches (crystal knobs and brushed nickle hardware). New wood-look tile floors throughout--not from China. All new fans and LED lighting inside and out. New central vac installed with unique wall hose storage system. Interior floors, walls, cabinets, and paint all low VOC!

Pool resurfaced, new pool pump and equipment, new lanai pavers installed including new drainage. Professionally landscaped yard with Florida friendly plants and trees throughout the newly installed walking trails in your own back yard! Low maintenance - no grass to cut. New irrigation system in back, updated in front for when watering is needed.

Enjoy low maintenance inside and out! NO FLOOD INSURANCE REQUIRED!

Note: 'Zestimate' is based on pre-renovation price and information and minimally-allowed updated data fields. This home is one of a kind.
1275 Windward Dr, Osprey, FL 34229 is a 3 bedroom, 2 bathroom, 1,981 sqft single-family home built in 1984. It last sold for $552,800 on Oct 31, 2019. It is currently off market. The Trulia Estimate is $748,900, with a rent estimate of $3,574/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 1275 Windward Dr

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1ElevatorFloors: Tile
Interior Details
AtticNumber of Rooms: 9Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, OfficeCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: MetalDeckExterior: Stone, Stucco, Cement Concrete, MetalFoundation Type: ConcreteGardenPatioPorchSprinkler System
Pool
Pool
Parking & Garage
GarageParking Spaces: 6Parking: Garage Attached, Off Street

Property Information

Year Built
Year Built: 1984Year Updated: 2017
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Building

Levels, Entrance, & Accessibility
Disabled Access
Fitness & Sports
Basketball CourtTennis Court
Community rooms
Fitness Center

Community

Units in Building: 1

Lot Information

Lot Area: 0.29 acres

Additional Information

Sport Court

Price History for 1275 Windward Dr

DatePriceEventSource
03/24/2021ListingRemovedN/A
10/31/2019$552,800Sold
N/A
01/12/2019$568,000ListingRemovedN/A
12/05/2018$568,000Listed For SaleN/A
08/22/2016$320,500Sold
N/A
02/23/2016$240,001Sold
N/A
01/20/2016$0Listed For SaleAgent Provided
04/05/2012$299,000ListingRemovedAgent Provided
10/21/2011$299,000PriceChange
Agent Provided
09/09/2011$317,500PriceChange
Agent Provided
06/09/2011$349,000Listed For SaleAgent Provided
12/10/2008$305,000Sold
N/A
12/21/2001$275,000Sold
N/A
07/13/1998$214,500Sold
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$744
Assessment$620,900
Home facts updated by county records

Comparable Sales for 1275 Windward Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1212 Windward Dr, Osprey, FL
0.10
Single-Family Home
$645,000
08/25/25
3
2
1,994
114 Windward Dr, Osprey, FL
0.14
Single-Family Home
$585,000
06/02/26
3
2
2,037
102 Windward Dr, Osprey, FL
0.13
Single-Family Home
$565,000
06/04/26
3
2.5
2,134
142 Dory Ln, Osprey, FL
0.11
Single-Family Home
$1,050,000
07/22/25
3
2
2,531
1486 Landview Ln, Osprey, FL
0.27
Single-Family Home
$817,000
06/30/26
3
2
1,869
1303 Thornapple Dr, Osprey, FL
0.30
Single-Family Home
$654,000
04/16/26
3
2
1,929
216 Windward Dr, Osprey, FL
0.26
Single-Family Home
$600,000
11/18/25
3
3
2,575
510 Latitude Ln, Osprey, FL
0.37
Single-Family Home
$550,000
03/23/26
3
2
2,298
1337 Copperwood Dr, Osprey, FL
0.35
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 1275 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

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Homes for sale near 1275 Windward Dr

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Off Market Homes Near 1275 Windward Dr

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