205 Windward Dr, Osprey, FL 34229
OFF MARKET

205 Windward Dr
Osprey, FL 34229

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

$824,100

Trulia Estimate
as of May 30, 2026
Est. Refi. Payment $5,011/mo*
Refinance Your Home

$824,100

Trulia Estimate
as of May 30, 2026
Est. Refi. Payment $5,011/mo*
Refinance Your Home
3 Beds
3 Baths
2,500 sqft
(on 0.33 acres)

Local Information

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

Description

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.
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
No Info

Home Details for 205 Windward Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: OtherHeating 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 History for 205 Windward Dr

DatePriceEventSource
01/05/2022ListingRemovedZillow Rental Manager
01/02/2022$4,400Listed For RentZillow Rental Manager
03/26/2018$3,300ListingRemovedAgent Provided
02/23/2018$3,300Listed For RentAgent Provided
11/04/2015$350,000Sold
N/A
08/05/2005$650,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$8,616
Assessment$681,200
Home facts updated by county records

Comparable Sales for 205 Windward Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
216 Windward Dr, Osprey, FL
0.04
Single-Family Home
$600,000
11/18/25
3
3
2,575
1235 Yacht Harbor Dr, Osprey, FL
0.09
Single-Family Home
$1,065,000
02/20/26
3
3
2,698
1218 Yacht Harbor Dr, Osprey, FL
0.11
Single-Family Home
$1,025,000
04/24/26
3
3
3,297
1212 Windward Dr, Osprey, FL
0.15
Single-Family Home
$645,000
08/25/25
3
2
1,994
264 Woods Point Rd, Osprey, FL
0.20
Single-Family Home
$425,000
10/29/25
2
3
2,837
142 Dory Ln, Osprey, FL
0.11
Single-Family Home
$1,050,000
07/22/25
3
2
2,531
288 Woods Point Rd, Osprey, FL
0.19
Single-Family Home
$445,000
04/10/26
3
2
1,788
447 Oak Point Rd, Osprey, FL
0.24
Single-Family Home
$520,000
12/30/25
4
3
2,688
1426 Landview Ln, Osprey, FL
0.40
Single-Family Home
$670,000
06/10/25
4
3
2,513
3957 Waypoint Ave, Osprey, FL
0.31
Single-Family Home
$900,000
01/16/26
3
3
2,328

Nearby homes

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Assigned Schools

These are the assigned schools for 205 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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205 Windward Dr, Osprey, FL 34229 is a 3 bedroom, 3 bathroom, 2,500 sqft single-family home built in 1988. This property is not currently available for sale. 205 Windward Dr was last sold on Nov 4, 2015 for $350,000. The current Trulia Estimate for 205 Windward Dr is $824,100.