205 Windward Dr, Osprey, FL 34229
OFF MARKET

$819,200

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 2,500 sqft (on 0.33 acres)

205 Windward Dr, Osprey, FL 34229

Est. Refi. Payment $5,084/mo*
Refinance Your Home
Currently Off Market - Sold Nov 4, 2015 for $350,000

Home Value

Trulia Estimate
$819K
Since last month
Increased$4K (+0.5%)
Since last year
Increased$20K (+2.5%)
Since last sale
Increased$469K (+134.1%)
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 +118% in the last 10 years
MonthEstimated value
2026
August 2026$819K
July 2026$815K
June 2026$849K
May 2026$822K
April 2026$839K
March 2026$807K
February 2026$825K
January 2026$802K
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
0.04
Single-Family Home
$600,000
11/18/25
3
3
2,575
204 WINDWARD DRIVE, Osprey, FL
0.03
Single-Family Home
$800,000
08/24/26
3
3
2,486
186 WINDWARD DRIVE, Osprey, FL
0.05
Single-Family Home
$565,000
07/20/26
3
2
2,505
102 WINDWARD DRIVE, Osprey, FL
0.16
Single-Family Home
$565,000
06/04/26
3
2.5
2,134
1235 YACHT HARBOR DRIVE, Osprey, FL
0.09
Single-Family Home
$1,065,000
02/20/26
3
3
2,698
1218 YACHT HARBOR DRIVE, Osprey, FL
0.11
Single-Family Home
$1,025,000
04/24/26
3
3
3,297
114 Windward Dr, Osprey, FL
0.14
Single-Family Home
$585,000
06/02/26
3
2
2,037
264 WOODS POINT ROAD, Osprey, FL
0.20
Single-Family Home
$425,000
10/29/25
3
3
2,837
486 YACHT HARBOR DRIVE, Osprey, FL
0.17
Single-Family Home
$1,325,000
08/25/26
3
3.5
2,939
288 WOODS POINT ROAD, Osprey, FL
0.19
Single-Family Home
$445,000
04/10/26
3
2
1,788

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
216 WINDWARD DRIVE, Osprey, FL 34229
0.04
$600,000
3
3
2,575
Recently Sold
204 WINDWARD DRIVE, Osprey, FL 34229
0.03
$800,000
3
3
2,486
Recently Sold
1237 FLYING BRIDGE LANE, Osprey, FL 34229
0.05
$842,500
3
2
2,045
Off Market
186 WINDWARD DRIVE, Osprey, FL 34229
0.05
$565,000
3
2
2,505
Recently Sold
188 DORY LANE, Osprey, FL 34229
0.06
$778,200
3
2
2,069
Off Market
1235 YACHT HARBOR DRIVE, Osprey, FL 34229
0.09
$1,065,000
3
3
2,698
Recently Sold
1218 YACHT HARBOR DRIVE, Osprey, FL 34229
0.11
$1,025,000
3
3
3,297
Recently Sold
142 DORY LANE, Osprey, FL 34229
0.11
-
3
2
2,531
Off Market
360 PINE RUN DRIVE, Osprey, FL 34229
0.16
$255,000
2
2
1,379
Off Market
362 PINE RUN DRIVE, Osprey, FL 34229
0.16
$215,000
2
2
1,224
Recently Sold
750 PINE RUN DRIVE, Osprey, FL 34229
0.16
$126,500
1
1
586
Off Market
756 PINE RUN DRIVE, Osprey, FL 34229
0.16
$260,300
2
2
1,224
Off Market

Local Information

  • Map ViewExplore the area around 205 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
1988
Lot Size
0.33 acres
Living Area
2,500 sqft
Price/Sqft
$328
Parking
Garage

About this House

Beautiful, executive, three bedroom pool home in Southbay Yacht and Racquet Club. Home has been fully updated, large kitchen with granite counter tops and stainless appliances. Master Bedroom has on suite master bath with large walk in shower and seat plus double sinks. Split floor plan with Jack and Jill bedrooms and guest bath. Great pool and lanai plus two car garage and laundry room.

More Photos coming

Tenant Pays utilities, tenant will need $13,200.00 representing first, last and security to move in plus a pet deposit ($500.00) if applicable. This is a non-smoking home. This is a non-furnished annual rental. Rental insurance/liability is required. Lawn and pool are the responsibility of the tenant.
205 Windward Dr, Osprey, FL 34229 is a 3 bedroom, 3 bathroom, 2,500 sqft single-family home built in 1988. It last sold for $350,000 on Nov 4, 2015. More recently, it was listed as a rental in January 2022 with an asking price of $4,400 per month. That rental listing was removed on January 5, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $819,200, with a rent estimate of $4,292/month.

Home Details for 205 Windward Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Other, Carpet
Interior Details
Number of Rooms: 5
Appliances & Utilities
DryerWasher

Exterior Features

Exterior Home Features
Roof: OtherExterior: StuccoFoundation Type: ConcretePatio
Pool
Pool
Parking & Garage
GarageParking: Garage Detached, Off Street

Property Information

Year Built
Year Built: 1988Year Updated: 1992
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.33 acres

Price and Tax history

DateEventPrice
Jan 5, 2022
Source: Zillow Rental Manager
ListingRemoved
Jan 2, 2022
Source: Zillow Rental Manager
Listed For Rent
$4,400
Mar 26, 2018
Source: Agent Provided
ListingRemoved
$3,300
Feb 23, 2018
Source: Agent Provided
Listed For Rent
$3,300
Nov 4, 2015
Source: N/A
Sold
$350,000

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 205 Windward Dr

  • What is 205 Windward Dr estimated to be worth?
    Trulia's estimated value for 205 Windward Dr in Osprey, FL is $819,200.
  • What is the price history for 205 Windward Dr?
    205 Windward Dr in Osprey, FL last sold for $350,000 in November 2015.
  • 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 205 Windward Dr have a pool?
    Yes, 205 Windward Dr in Osprey, FL has a pool.
  • Does 205 Windward Dr have laundry facilities?
    Yes, 205 Windward Dr in Osprey, FL has in-unit laundry.

Explore by feature - Pet Friendly

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Explore by feature - Garage

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Explore by feature - Air Conditioning

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Explore by feature - Pool

20 rentals with a pool in Osprey, FL

Explore by feature - Washer/dryer

24 rentals with a washer/dryer in Osprey, FL

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