306 Windward Dr, Osprey, FL 34229
OFF MARKET

306 Windward Dr
Osprey, FL 34229

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

$788,700

Trulia Estimate
as of Jun 11, 2026
Est. Refi. Payment $4,869/mo*
Refinance Your Home

$788,700

Trulia Estimate
as of Jun 11, 2026
Est. Refi. Payment $4,869/mo*
Refinance Your Home
3 Beds
2 Baths
1,963 sqft
(on 0.30 acres)

Local Information

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

Description

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.
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
Patio, Pool
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 306 Windward Dr

Interior Features

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

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 History for 306 Windward Dr

DatePriceEventSource
02/23/2015$300,000Sold
N/A
12/03/2014$325,700PriceChange
Agent Provided
10/20/2014$349,700PriceChange
Agent Provided
09/26/2014$375,000Listed For SaleAgent Provided

Market trends in Osprey

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$600K
$73.33KMoM
Sale-to-List Price
94.4%
0.3%MoM
Price per sq ft
$277
$29MoM
Available listings
162
1MoM
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Property Tax and Assessment

Year2025
Tax$8,462
Assessment$709,200
Home facts updated by county records

Homeowner tools

Estimated monthly rent$3,803/mo
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Homes for rent near 306 Windward Dr

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Comparable Sales for 306 Windward Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1212 Windward Dr, Osprey, FL
0.23
Single-Family Home
$645,000
08/25/25
3
2
1,994
216 Windward Dr, Osprey, FL
0.05
Single-Family Home
$600,000
11/18/25
3
3
2,575
288 Woods Point Rd, Osprey, FL
0.15
Single-Family Home
$445,000
04/10/26
3
2
1,788
328 Woods Point Rd, Osprey, FL
0.13
Single-Family Home
$489,000
07/03/25
2
2
1,862
432 Yacht Harbor Dr, Osprey, FL
0.23
Single-Family Home
$1,075,000
05/19/26
3
2.5
2,125
102 Windward Dr, Osprey, FL
0.23
Single-Family Home
$565,000
06/04/26
3
2.5
2,134
1235 Yacht Harbor Dr, Osprey, FL
0.07
Single-Family Home
$1,065,000
02/20/26
3
3
2,698
1218 Yacht Harbor Dr, Osprey, FL
0.05
Single-Family Home
$1,025,000
04/24/26
3
3
3,297
142 Dory Ln, Osprey, FL
0.20
Single-Family Home
$1,050,000
07/22/25
3
2
2,531
264 Woods Point Rd, Osprey, FL
0.16
Single-Family Home
$425,000
10/29/25
2
3
2,837

Nearby homes

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Assigned Schools

These are the assigned schools for 306 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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Homes for sale near 306 Windward Dr

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Off Market Homes Near 306 Windward Dr

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306 Windward Dr, Osprey, FL 34229 is a 3 bedroom, 2 bathroom, 1,963 sqft single-family home built in 1980. This property is not currently available for sale. 306 Windward Dr was last sold on Feb 23, 2015 for $300,000. The current Trulia Estimate for 306 Windward Dr is $788,700.