138 Windward Dr, Osprey, FL 34229
OFF MARKET

138 Windward Dr
Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,204 sqft (on 0.28 acres)

$760,900

Trulia Estimate
as of Jul 30, 2026
Est. Refi. Payment $4,732/mo*
Refinance Your Home

$760,900

Trulia Estimate
as of Jul 30, 2026
Est. Refi. Payment $4,732/mo*
Refinance Your Home
3 Beds
3 Baths
2,204 sqft
(on 0.28 acres)

Local Information

  • Map ViewExplore the area around 138 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
1985
Lot Size
0.28 acres
Living Area
2,204 sqft
Price/Sqft
$345
Parking
Garage

About this House

This is a beautiful pool home in highly desirable Southbay boating community. This home features a beautiful native Florida rock fireplace and built-in china/serving area with glass doors, shelves and interior lighting. The three sliding glass doors in the family room open onto the pool area to expand the living area onto the pool deck. The extensive pool area features tropical plants and a large entertaining / dining area. The mature lush landscaping ensures backyard privacy and enjoyment. A monthly calendar of activities in Southbay keep residents engaged and connected to this great community. This home is close to Gulf Coast beaches, area restaurants and shopping, and highly acclaimed schools. This property is eligible under the Freddie Mac First Look Initiative through 11/15/2018. Seller will only provide a 10 days inspection period. Come see this property today!
138 Windward Dr, Osprey, FL 34229 is a 3 bedroom, 3 bathroom, 2,204 sqft single-family home built in 1985. It last sold for $402,000 on Nov 30, 2018. More recently, it was listed as a rental in March 2017 with an asking price of $2,700 per month. That rental listing was removed on August 11, 2017. It is currently off market. The Trulia Estimate is $760,900, with a rent estimate of $3,861/month.

Home Details for 138 Windward Dr

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningCooling System: Central, OtherHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile
Interior Details
Number of Rooms: 7Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Master Bath, Office, PantryCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDisposalMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: TileExterior: StuccoFoundation Type: ConcreteLawnPatioSprinkler System
Pool
Pool
Parking & Garage
GarageParking: Garage Attached, Off Street

Property Information

Year Built
Year Built: 1985Year Updated: 1990
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.28 acres

Building

Community rooms
Fitness Center
Fitness & Sports
Tennis Court

Price History for 138 Windward Dr

DatePriceEventSource
11/30/2018$402,000Sold
N/A
10/31/2018$399,900PendingAgent Provided
10/26/2018$399,900Listed For SaleAgent Provided
06/06/2018$382,200ListingRemovedAgent Provided
05/11/2018$0Listed For SaleAgent Provided
01/11/2018$315,628ListingRemovedAgent Provided
12/14/2017$437,653Listed For SaleAgent Provided
08/11/2017$2,200ListingRemovedN/A
06/05/2017$2,200PriceChange
N/A
05/02/2017$2,700PriceChange
N/A
04/23/2017$2,500PriceChange
N/A
03/21/2017$2,700Listed For RentN/A
03/16/2017$437,621ListingRemovedAgent Provided
12/23/2016$0Listed For SaleAgent Provided
06/01/2016$459,000ListingRemovedAgent Provided
03/15/2016$459,000PriceChange
Agent Provided
01/28/2016$499,950PriceChange
Agent Provided
11/10/2015$519,000Listed For SaleAgent Provided
09/29/2015$2,950ListingRemovedN/A
08/26/2015$2,950Listed For RentN/A
08/26/2015$494,500ListingRemovedAgent Provided
04/01/2015$494,500Listed For SaleAgent Provided
07/16/2014$2,900ListingRemovedN/A
06/15/2014$2,900Listed For RentN/A
10/18/2012$2,900ListingRemovedAgent Provided
01/22/2003$355,000Sold
N/A
04/16/2002$335,000Sold
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$5,710
Assessment$680,900
Home facts updated by county records

Comparable Sales for 138 Windward Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
102 WINDWARD DRIVE, Osprey, FL
0.05
Single-Family Home
$565,000
06/04/26
3
2.5
2,134
114 Windward Dr, Osprey, FL
0.03
Single-Family Home
$585,000
06/02/26
3
2
2,037
216 WINDWARD DRIVE, Osprey, FL
0.13
Single-Family Home
$600,000
11/18/25
3
3
2,575
186 WINDWARD DRIVE, Osprey, FL
0.07
Single-Family Home
$565,000
07/20/26
3
2
2,505
1212 WINDWARD DRIVE, Osprey, FL
0.05
Single-Family Home
$645,000
08/25/25
3
2
1,994
1235 YACHT HARBOR DRIVE, Osprey, FL
0.20
Single-Family Home
$1,065,000
02/20/26
3
3
2,698
264 WOODS POINT ROAD, Osprey, FL
0.22
Single-Family Home
$425,000
10/29/25
2
3
2,837
1218 YACHT HARBOR DRIVE, Osprey, FL
0.22
Single-Family Home
$1,025,000
04/24/26
3
3
3,297
1313 THORNAPPLE DRIVE, Osprey, FL
0.39
Single-Family Home
$525,000
12/04/25
3
3
2,082
288 WOODS POINT ROAD, Osprey, FL
0.23
Single-Family Home
$445,000
04/10/26
3
2
1,788

Nearby homes

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Assigned Schools

These are the assigned schools for 138 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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Apartments for Rent

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Explore by feature - Pet Friendly

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Explore by feature - Garage

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Explore by feature - Pool

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Explore by feature - Washer/dryer

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Homes for sale near 138 Windward Dr

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Off Market Homes Near 138 Windward Dr

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