161 Windward Dr, Osprey, FL 34229
OFF MARKET

$1,003,400

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

161 Windward Dr, Osprey, FL 34229

Est. Refi. Payment $6,232/mo*
Refinance Your Home
Currently Off Market - Sold Dec 11, 2012 for $405,000

Home Value

Trulia Estimate
$1M
Since last month
Increased$600 (+0.1%)
Since last year
Decreased$9K (-0.9%)
Since last sale
Increased$591K (+145.9%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +75% in the last 10 years
MonthEstimated value
2026
August 2026$996K
July 2026$995K
June 2026$1.04M
May 2026$1.01M
April 2026$1.04M
March 2026$1.03M
February 2026$1.05M
January 2026$1M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
216 WINDWARD DRIVE, Osprey, FL
0.10
Single-Family Home
$600,000
11/18/25
3
3
2,575
186 WINDWARD DRIVE, Osprey, FL
0.05
Single-Family Home
$565,000
07/20/26
3
2
2,505
204 WINDWARD DRIVE, Osprey, FL
0.08
Single-Family Home
$800,000
08/24/26
3
3
2,486
102 WINDWARD DRIVE, Osprey, FL
0.09
Single-Family Home
$565,000
06/04/26
3
2.5
2,134
114 Windward Dr, Osprey, FL
0.08
Single-Family Home
$585,000
06/02/26
3
2
2,037
1218 YACHT HARBOR DRIVE, Osprey, FL
0.18
Single-Family Home
$1,025,000
04/24/26
3
3
3,297
1235 YACHT HARBOR DRIVE, Osprey, FL
0.16
Single-Family Home
$1,065,000
02/20/26
3
3
2,698
264 WOODS POINT ROAD, Osprey, FL
0.23
Single-Family Home
$425,000
10/29/25
3
3
2,837
447 OAK POINT ROAD, 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

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
186 WINDWARD DRIVE, Osprey, FL 34229
0.05
$565,000
3
2
2,505
Recently Sold
188 DORY LANE, Osprey, FL 34229
0.05
$784,900
3
2
2,069
Off Market
204 WINDWARD DRIVE, Osprey, FL 34229
0.08
$800,000
3
3
2,486
Recently Sold
216 WINDWARD DRIVE, Osprey, FL 34229
0.10
$600,000
3
3
2,575
Recently Sold
142 DORY LANE, Osprey, FL 34229
0.05
$1,020,800
3
2
2,531
Off Market
1237 FLYING BRIDGE LANE, Osprey, FL 34229
0.11
$838,900
3
2
2,045
Off Market
1212 WINDWARD DRIVE, Osprey, FL 34229
0.08
$630,700
3
2
1,994
Off Market
102 WINDWARD DRIVE, Osprey, FL 34229
0.09
$565,000
3
2.5
2,134
Recently Sold
104 WOODLAND PLACE, Osprey, FL 34229
0.12
$259,500
2
2
1,316
Off Market
105 WOODLAND PLACE, Osprey, FL 34229
0.12
$231,900
2
2
1,325
Off Market
107 WOODLAND PLACE #107, Osprey, FL 34229
0.12
$145,900
1
1.5
865
Off Market
111 WOODLAND PLACE, Osprey, FL 34229
0.12
$227,000
2
2
1,316
Recently Sold

Local Information

  • Map ViewExplore the area around 161 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
1980
Lot Size
0.28 acres
Living Area
3,157 sqft
Price/Sqft
$318
Parking
Garage

About this House

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
161 Windward Dr, Osprey, FL 34229 is a 4 bedroom, 3 bathroom, 3,157 sqft single-family home built in 1980. It last sold for $405,000 on Dec 11, 2012. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,003,400, with a rent estimate of $5,589/month.

Home Details for 161 Windward Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Carpet
Interior Details
Number of Rooms: 6Ceiling Fan
Heating & Cooling
Air Conditioning
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 and Tax history

DateEventPrice
Dec 11, 2012
Source: N/A
Sold
$405,000
Oct 21, 2012
Source: Agent Provided
Listed For Sale
$399,900
Sep 24, 2012
Source: N/A
Sold
$308,280
Feb 17, 2011
Source: Agent Provided
ListingRemoved
$499,000
Jun 19, 2010
Source: Agent Provided
PriceChange
$499,000
Price decreased by 9%

Market trends in Osprey

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
133
7MoM

Around this home

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 it's walkable to grocery stores

  • 41 % Say there are community events

  • 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

LGBTQ Local Legal Protections

Frequently asked questions about 161 Windward Dr

  • What is 161 Windward Dr estimated to be worth?
    Trulia's estimated value for 161 Windward Dr in Osprey, FL is $1,003,400.
  • What is the price history for 161 Windward Dr?
    161 Windward Dr in Osprey, FL last sold for $405,000 in December 2012.
  • Is Osprey a buyer's or seller's market?
    Osprey is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Osprey?
    Residents describe Osprey, FL as dog-friendly, quiet, and easy to park in. Most residents say you need a car. See recently sold homes in Osprey, FL.
  • Does 161 Windward Dr have a pool?
    Yes, 161 Windward Dr in Osprey, FL has a pool.
  • How big is the lot at 161 Windward Dr?
    The lot at 161 Windward Dr in Osprey, FL is about 0.28 acres (12,196 sq ft).

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