161 Windward Dr, Osprey, FL 34229
OFF MARKET

161 Windward Dr
Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,157 sqft (on 0.28 acres)

$1,009,000

Trulia Estimate
as of Jun 3, 2026
Est. Refi. Payment $5,190/mo*
Refinance Your Home

$1,009,000

Trulia Estimate
as of Jun 3, 2026
Est. Refi. Payment $5,190/mo*
Refinance Your Home
4 Beds
3 Baths
3,157 sqft
(on 0.28 acres)

Local Information

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

Description

QUICK CLOSING OK! Enjoy the very sought after Southbay Yacht and Racquet Club community. Be greeted at the front entry with a lovely babbling brook waterfall... Step inside to that "Welcome Home" feeling you will get from this GORGEOUS Open floor plan and beautiful stone woodburning Fireplace,great for entertaining! This lovely POOL home also features 4 bedrooms, 3 bathrooms,and BRAND NEW wood flooring in the HUGE GreatRoom. The KITCHEN and ALL 3 Bathrooms have been beautifully updated. Brand new tile, fixtures,cabinetry, granite counter tops throughout, stainless steel appliances, convection oven, convection microwave and much much more!! The 4th bedroom is also a master suite with its own separate entrance. This home is SPARKLING fresh and ready for a new family. The Yacht Club has direct access to Sarasota Bay. Stroll along the private path by the bay, stop and sit a while to enjoy the Sunsets. Water is within walking or biking distance from the house.... See Realtor Remarks for community website. Go to the Southbay website to check out the Rules and Regulations and to get more information about this Special Yacht Club community. Brokered And Advertised By: GREEN LION REALTY LLC Listing Agent: ROSEMARY CRANDALL
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
Porch, Patio, Deck, Pool
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 161 Windward Dr

Interior Features

Heating & Cooling
Heating: OtherAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1Floors: Carpet
Interior Details
Number of Rooms: 6Ceiling Fan
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: StuccoFoundation Type: ConcretePatioPorch
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1980Year Updated: 1995
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.28 acres

Building

Fitness & Sports
Tennis Court

Price History for 161 Windward Dr

DatePriceEventSource
12/11/2012$405,000Sold
N/A
10/21/2012$399,900Listed For SaleAgent Provided
09/24/2012$308,280Sold
N/A
02/17/2011$499,000ListingRemovedAgent Provided
06/19/2010$499,000PriceChange
Agent Provided
04/24/2010$549,000PriceChange
Agent Provided
02/04/2010$699,000Listed For SaleAgent Provided
06/06/2009$650,000ListingRemovedAgent Provided
05/22/2009$650,000Listed For SaleAgent Provided
11/18/2004$514,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$5,684
Assessment$794,300
Home facts updated by county records

Comparable Sales for 161 Windward Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
216 Windward Dr, Osprey, FL
0.10
Single-Family Home
$600,000
11/18/25
3
3
2,575
1218 Yacht Harbor Dr, Osprey, FL
0.18
Single-Family Home
$1,025,000
04/24/26
3
3
3,297
1235 Yacht Harbor Dr, Osprey, FL
0.16
Single-Family Home
$1,065,000
02/20/26
3
3
2,698
1212 Windward Dr, Osprey, FL
0.08
Single-Family Home
$645,000
08/25/25
3
2
1,994
1426 Landview Ln, Osprey, FL
0.34
Single-Family Home
$670,000
06/10/25
4
3
2,513
264 Woods Point Rd, Osprey, FL
0.23
Single-Family Home
$425,000
10/29/25
2
3
2,837
142 Dory Ln, Osprey, FL
0.05
Single-Family Home
$1,050,000
07/22/25
3
2
2,531
447 Oak Point Rd, Osprey, FL
0.30
Single-Family Home
$520,000
12/30/25
4
3
2,688
1319 Thornapple Dr, Osprey, FL
0.43
Single-Family Home
$290,500
09/16/25
4
3.5
3,067
304 Yacht Harbor Dr, Osprey, FL
0.26
Single-Family Home
$2,000,000
05/19/26
4
4
3,324

Nearby homes

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Assigned Schools

These are the assigned schools for 161 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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161 Windward Dr, Osprey, FL 34229 is a 4 bedroom, 3 bathroom, 3,157 sqft single-family home built in 1980. This property is not currently available for sale. 161 Windward Dr was last sold on Dec 11, 2012 for $405,000. The current Trulia Estimate for 161 Windward Dr is $1,009,000.