306 Windward Dr, Osprey, FL 34229
OFF MARKET

$786,500

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,963 sqft (on 0.30 acres)

306 Windward Dr, Osprey, FL 34229

Est. Refi. Payment $4,888/mo*
Refinance Your Home
Currently Off Market - Sold Feb 23, 2015 for $300,000

Home Value

Trulia Estimate
$787K
Since last month
Increased$4K (+0.5%)
Since last year
Increased$51K (+6.9%)
Since last sale
Increased$494K (+164.8%)
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 +129% in the last 10 years
MonthEstimated value
2026
August 2026$794K
August 2026$793K
July 2026$790K
June 2026$805K
May 2026$789K
April 2026$815K
March 2026$792K
February 2026$810K
January 2026$788K
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
186 WINDWARD DRIVE, Osprey, FL
0.11
Single-Family Home
$565,000
07/20/26
3
2
2,505
114 Windward Dr, Osprey, FL
0.21
Single-Family Home
$585,000
06/02/26
3
2
2,037
216 WINDWARD DRIVE, Osprey, FL
0.05
Single-Family Home
$600,000
11/18/25
3
3
2,575
288 WOODS POINT ROAD, Osprey, FL
0.15
Single-Family Home
$445,000
04/10/26
3
2
1,788
204 WINDWARD DRIVE, Osprey, FL
0.07
Single-Family Home
$800,000
08/24/26
3
3
2,486
432 Yacht Harbor Dr, Osprey, FL
0.23
Single-Family Home
$1,075,000
05/19/26
3
2.5
2,125
102 WINDWARD DRIVE, Osprey, FL
0.23
Single-Family Home
$565,000
06/04/26
3
2.5
2,134
1235 YACHT HARBOR DRIVE, Osprey, FL
0.07
Single-Family Home
$1,065,000
02/20/26
3
3
2,698
1218 YACHT HARBOR DRIVE, Osprey, FL
0.05
Single-Family Home
$1,025,000
04/24/26
3
3
3,297
264 WOODS POINT ROAD, Osprey, FL
0.16
Single-Family Home
$425,000
10/29/25
3
3
2,837

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
1218 YACHT HARBOR DRIVE, Osprey, FL 34229
0.05
$1,025,000
3
3
3,297
Recently Sold
1235 YACHT HARBOR DRIVE, Osprey, FL 34229
0.07
$1,065,000
3
3
2,698
Recently Sold
216 WINDWARD DRIVE, Osprey, FL 34229
0.05
$600,000
3
3
2,575
Recently Sold
1237 FLYING BRIDGE LANE, Osprey, FL 34229
0.10
$842,800
3
2
2,045
Off Market
204 WINDWARD DRIVE, Osprey, FL 34229
0.07
$800,000
3
3
2,486
Recently Sold
186 WINDWARD DRIVE, Osprey, FL 34229
0.11
$565,000
3
2
2,505
Recently Sold
486 YACHT HARBOR DRIVE, Osprey, FL 34229
0.14
$1,325,000
3
3.5
2,939
Recently Sold
188 DORY LANE, Osprey, FL 34229
0.14
$784,900
3
2
2,069
Off Market
1140 BEACHCOMBER COURT #11, Osprey, FL 34229
0.12
$540,000
3
2.5
2,040
For Sale
1110 BEACHCOMBER COURT #1, Osprey, FL 34229
0.12
$461,200
3
2.5
2,166
Off Market
1116 BEACHCOMBER COURT #3, Osprey, FL 34229
0.12
$530,000
3
2.5
2,040
Recently Sold
1164 BEACHCOMBER COURT #19, Osprey, FL 34229
0.12
$519,300
3
2.5
1,952
Off Market

Local Information

  • Map ViewExplore the area around 306 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
0.3 acres
Living Area
1,963 sqft
Price/Sqft
$401
Parking
Garage

About this House

With a wonderfully-executed floor plan, this home has a lot to offer in its space. Three bedrooms two baths, living/dining room combo, kitchen has an open pass through to the family room which has a floor to ceiling view of the privately walled pool area. Newer roof and FFE 12.3. Located in a well-established waterfront community. Southbay Yacht and Racquet Club offers an active Clubhouse with something for everyone. Heated community pool, tennis courts, marina, private park, gym, and sidewalks. Just steps away from shopping and restaurants. Southbay has close access to Beaches, bike trails and a state park.
306 Windward Dr, Osprey, FL 34229 is a 3 bedroom, 2 bathroom, 1,963 sqft single-family home built in 1980. It last sold for $300,000 on Feb 23, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $786,500, with a rent estimate of $3,836/month.

Home Details for 306 Windward Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet
Interior Details
Number of Rooms: 8
Appliances & Utilities
DryerMicrowaveRefrigeratorWasher
Heating & Cooling
Air ConditioningCooling System: Central

Exterior Features

Exterior Home Features
Roof: OtherExterior: Other, StuccoFoundation Type: ConcretePatio
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1980Year Updated: 1990
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.30 acres

Additional Information

Sport Court

Price and Tax history

DateEventPrice
Feb 23, 2015
Source: N/A
Sold
$300,000
Dec 3, 2014
Source: Agent Provided
PriceChange
$325,700
Price decreased by 7%
Oct 20, 2014
Source: Agent Provided
PriceChange
$349,700
Price decreased by 7%
Sep 26, 2014
Source: Agent Provided
Listed For Sale
$375,000

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 306 Windward Dr

  • What is 306 Windward Dr estimated to be worth?
    Trulia's estimated value for 306 Windward Dr in Osprey, FL is $786,500.
  • What is the price history for 306 Windward Dr?
    306 Windward Dr in Osprey, FL last sold for $300,000 in February 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 306 Windward Dr have air conditioning?
    Yes, 306 Windward Dr in Osprey, FL has air conditioning.
  • Does 306 Windward Dr have a pool?
    Yes, 306 Windward Dr in Osprey, FL has a pool.

Explore by feature - Pet Friendly

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Explore by feature - Air Conditioning

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Explore by feature - Pool

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Explore by feature - Washer/dryer

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