1227 Windward Dr, Osprey, FL 34229
Property image
Property image
OFF MARKET

$595,600

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,944 sqft (on 12,148 acres)

1227 Windward Dr, Osprey, FL 34229

Est. Refi. Payment $3,853/mo*
Refinance Your Home
Currently Off Market - Sold Jul 15, 2009 for $280,000

Home Value

Trulia Estimate
$596K
Since last month
Decreased$11K (-1.8%)
Since last year
Decreased$22K (-3.5%)
Since last sale
Increased$318K (+113.7%)
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 +47% in the last 10 years
MonthEstimated value
2026
August 2026$598K
August 2026$596K
July 2026$609K
June 2026$615K
May 2026$612K
April 2026$627K
March 2026$595K
February 2026$619K
January 2026$630K
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
114 Windward Dr, Osprey, FL
0.07
Single-Family Home
$585,000
06/02/26
3
2
2,037
102 WINDWARD DRIVE, Osprey, FL
0.06
Single-Family Home
$565,000
06/04/26
3
2.5
2,134
186 WINDWARD DRIVE, Osprey, FL
0.16
Single-Family Home
$565,000
07/20/26
3
2
2,505
288 WOODS POINT ROAD, Osprey, FL
0.33
Single-Family Home
$445,000
04/10/26
3
2
1,788
1303 THORNAPPLE DRIVE, Osprey, FL
0.33
Single-Family Home
$654,000
04/16/26
3
2
1,929
1337 COPPERWOOD DRIVE, Osprey, FL
0.40
Single-Family Home
$520,000
06/17/26
3
2
2,172
553 Meadow Sweet Cir, Osprey, FL
0.40
Single-Family Home
$570,000
02/04/26
3
2
1,887
1313 THORNAPPLE DRIVE, Osprey, FL
0.31
Single-Family Home
$525,000
12/04/25
3
3
2,082
584 MEADOW SWEET CIRCLE, Osprey, FL
0.39
Single-Family Home
$585,000
03/27/26
3
2
2,151
216 WINDWARD DRIVE, Osprey, FL
0.21
Single-Family Home
$600,000
11/18/25
3
3
2,575

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
102 WINDWARD DRIVE, Osprey, FL 34229
0.06
$565,000
3
2.5
2,134
Recently Sold
1212 WINDWARD DRIVE, Osprey, FL 34229
0.04
$633,300
3
2
1,994
Off Market
1251 WINDWARD DRIVE, Osprey, FL 34229
0.03
$833,700
3
2
2,015
Off Market
139 WOODLAND PLACE #139, Osprey, FL 34229
0.10
$235,000
1
1.5
865
Recently Sold
142 DORY LANE, Osprey, FL 34229
0.08
$1,024,900
3
2
2,531
Off Market
104 WOODLAND PLACE, Osprey, FL 34229
0.12
$258,100
2
2
1,316
Off Market
105 WOODLAND PLACE, Osprey, FL 34229
0.12
$232,100
2
2
1,325
Off Market
107 WOODLAND PLACE #107, Osprey, FL 34229
0.12
$146,500
1
1.5
865
Off Market
111 WOODLAND PLACE, Osprey, FL 34229
0.12
$227,000
2
2
1,316
Recently Sold
124 WOODLAND DRIVE, Osprey, FL 34229
0.12
$228,600
2
2
1,325
Off Market
135 WOODLAND PLACE, Osprey, FL 34229
0.12
$260,000
2
2
1,316
Recently Sold
116 WOODLAND PLACE #116, Osprey, FL 34229
0.12
$249,900
2
2
1,325
For Sale

Local Information

  • Map ViewExplore the area around 1227 Windward Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1983
12,148 acre lot
1,944 sqft
$306/sqft
Garage

About this House

Come and experience all Southbay has to offer in this wonderful 3 bedroom, 2 bath pool home. Beautifully updated kitchen. Exceptionally large living/dining room combination with triple sliders to the lanai & pool area. Private yard, lush gardens
1227 Windward Dr, Osprey, FL 34229 is a 3 bedroom, 2 bathroom, 1,944 sqft single-family home built in 1983. It last sold for $280,000 on Jul 15, 2009. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $595,600, with a rent estimate of $3,697/month.

Home Details for 1227 Windward Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Other, Carpet
Interior Details
Number of Rooms: 6
Heating & Cooling
Air Conditioning

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: OtherFoundation Type: ConcretePatio
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1983Year Updated: 1988
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 12148.00 acres

Price and Tax history

DateEventPrice
Jul 15, 2009
Source: N/A
Sold
$280,000
Mar 11, 2009
Source: Agent Provided
ListingRemoved
$349,900
Jan 13, 2009
Source: Agent Provided
Listed For Sale
$349,900
Mar 25, 2004
Source: N/A
Sold
$365,000
Mar 11, 2002
Source: N/A
Sold
$312,500

Market trends in Osprey

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$714K
$28.67KMoM
Sale-to-List Price
—
Price per sq ft
—
Available listings
112
22MoM

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 1227 Windward Dr

  • What is 1227 Windward Dr estimated to be worth?
    Trulia's estimated value for 1227 Windward Dr in Osprey, FL is $595,600.
  • What is the price history for 1227 Windward Dr?
    1227 Windward Dr in Osprey, FL last sold for $280,000 in July 2009.
  • Is Osprey a buyer's or seller's market?
    Osprey is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Osprey?
    The median sale price in Osprey is $714K. That is up $28.67K from the prior month.
  • Does 1227 Windward Dr have a pool?
    Yes, 1227 Windward Dr in Osprey, FL has a pool.
  • How big is the lot at 1227 Windward Dr?
    The lot at 1227 Windward Dr in Osprey, FL is about 12148 acres.

Explore by feature - Pet Friendly

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