186 WINDWARD DRIVE, OSPREY, FL 34229
Home value
$563,100
$512,000 - $619,000
$3,321/mo
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Listing updated:
Brittany Coleman, PLLC 941-539-5023,
KELLER WILLIAMS ON THE WATER S 941-803-7522
Brittany Coleman, PLLC, 3329354
KELLER WILLIAMS ON THE WATER S

Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Rooms
- Room types: Bonus Room, Family Room
Primary bedroom
- Features: Ceiling Fan(s), En Suite Bathroom, Walk-In Closet(s)
- Level: First
- Area: 244.88 Square Feet
- Dimensions: 11.6x21.11
Bedroom 1
- Features: Ceiling Fan(s), Walk-In Closet(s)
- Level: First
- Area: 126.38 Square Feet
- Dimensions: 12.5x10.11
Bedroom 2
- Features: Ceiling Fan(s), Built-in Closet
- Level: First
- Area: 142.78 Square Feet
- Dimensions: 11.8x12.1
Primary bathroom
- Features: Built-In Shelving, Built-In Shower Bench, En Suite Bathroom, Shower No Tub, Single Vanity, Steam Shower, Stone Counters, Window/Skylight in Bath, Linen Closet
- Level: First
- Area: 85.84 Square Feet
- Dimensions: 11.6x7.4
Bathroom 2
- Features: Built-In Shelving, Shower No Tub, Single Vanity, Steam Shower, Stone Counters
- Level: First
- Area: 36.21 Square Feet
- Dimensions: 7.1x5.1
Bonus room
- Features: Ceiling Fan(s), Storage Closet
- Level: First
- Area: 648.34 Square Feet
- Dimensions: 35.8x18.11
Dinette
- Features: Ceiling Fan(s)
- Level: First
- Area: 142.78 Square Feet
- Dimensions: 11.8x12.1
Dining room
- Level: First
- Area: 103.12 Square Feet
- Dimensions: 10.11x10.2
Family room
- Features: Ceiling Fan(s)
- Level: First
- Area: 153.32 Square Feet
- Dimensions: 13.8x11.11
Kitchen
- Features: Breakfast Bar
- Level: First
- Area: 153.51 Square Feet
- Dimensions: 12.9x11.9
Living room
- Features: Ceiling Fan(s)
- Level: First
- Area: 303.15 Square Feet
- Dimensions: 21.5x14.1
Heating
- Central
Cooling
- Central Air
Appliances
- Included: Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
- Laundry: Inside, Laundry Room
Features
- Cathedral Ceiling(s), Ceiling Fan(s), High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Primary Bedroom Main Floor, Split Bedroom, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s)
- Flooring: Hardwood
- Doors: Sliding Doors
- Has fireplace: No
Interior area
- Total structure area: 3,298
- Total interior livable area: 2,505 sqft
Property
Parking
- Total spaces: 2
- Parking features: Deeded, Driveway, Garage Door Opener, Off Street
- Attached garage spaces: 2
- Has uncovered spaces: Yes
- Details: Garage Dimensions: 21x22
Features
- Levels: One
- Stories: 1
- Patio & porch: Covered, Patio, Screened
- Exterior features: Irrigation System, Lighting, Private Mailbox, Rain Gutters
- Has view: Yes
- View description: Garden
- Waterfront features: Intracoastal Waterway Access, Marina Access
Lot
- Size: 0.3 Acres
- Features: Corner Lot, Landscaped
- Residential vegetation: Trees/Landscaped
Details
- Parcel number: 0157070011
- Zoning: RSF2
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Block, Stucco
- Foundation: Slab
- Roof: Tile
Condition
- New construction: No
- Year built: 1983
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: BB/HS Internet Available, Cable Available, Cable Connected, Electricity Available, Electricity Connected, Sewer Available, Sewer Connected, Water Available, Water Connected
Community & HOA
Community
- Features: Boat Slip, Dock, Intracoastal Waterway, Marina, Clubhouse, Deed Restrictions, Fitness Center, Golf Carts OK, Park, Playground, Pool, Sidewalks, Tennis Court(s)
- Pet fee: $0 monthly
- Subdivision: SOUTHBAY YACHT & RACQUET CLUB
HOA
- Has HOA: Yes
- Amenities included: Basketball Court, Clubhouse, Fitness Center, Park, Pickleball Court(s), Playground, Pool, Tennis Court(s)
- Services included: Common Area Taxes, Community Pool, Reserve Fund, Fidelity Bond, Manager, Pool Maintenance
- HOA fee: $204 monthly
- HOA name: Judy Brown
- HOA phone: 941-966-4237
Location
- Region: Osprey
Financial & listing details
- Price per square foot: $226/sqft
- Tax assessed value: $588,800
- Annual tax amount: $7,566
- Date on market: 1/8/2026
- Cumulative days on market: 116 days
- Listing terms: Cash,Conventional,FHA,VA Loan
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Paved, Asphalt
Price history
| Date | Event | Price |
|---|---|---|
| 7/20/2026 | Sold | $565,000-5.8%$226/sqft |
Source: | ||
| 7/8/2026 | Contingent | $599,900$239/sqft |
Source: | ||
| 5/13/2026 | Pending sale | $599,900$239/sqft |
Source: | ||
| 5/7/2026 | Price change | $599,900-7.6%$239/sqft |
Source: | ||
| 3/19/2026 | Listed for sale | $649,500$259/sqft |
Source: | ||
| 3/13/2026 | Pending sale | $649,500$259/sqft |
Source: | ||
| 3/6/2026 | Price change | $649,500-13.4%$259/sqft |
Source: | ||
| 1/9/2026 | Listed for sale | $749,900+29.3%$299/sqft |
Source: | ||
| 11/4/2021 | Sold | $580,000$232/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $7,566 -8.7% | $588,800 -14.1% |
| 2024 | $8,291 +9.1% | $685,700 +9.8% |
| 2023 | $7,601 +14% | $624,500 +15.7% |
| 2022 | $6,666 +104.1% | $539,700 +94% |
| 2021 | $3,266 -0.3% | $278,153 +1.4% |
| 2020 | $3,275 +3.8% | $274,313 +2.3% |
| 2019 | $3,155 | $268,146 +1.9% |
| 2018 | $3,155 +2.6% | $263,146 +2.1% |
| 2017 | $3,075 -0.9% | $257,734 -15.7% |
| 2016 | $3,104 | $305,600 +3.8% |
| 2015 | $3,104 +0.4% | $294,400 +20.2% |
| 2014 | $3,091 +0.1% | $245,013 |
| 2013 | $3,088 +2.9% | $245,013 +1.7% |
| 2012 | $3,001 +4.9% | $240,917 +3% |
| 2011 | $2,860 -7.7% | $233,900 -4.8% |
| 2010 | $3,099 +10.7% | $245,664 +2.7% |
| 2009 | $2,799 | $239,205 +0.1% |
| 2008 | $2,799 -2.3% | $238,966 +3% |
| 2007 | $2,866 | $232,006 +2.5% |
| 2006 | -- | $226,347 +3% |
| 2005 | -- | $219,754 +3% |
| 2004 | $2,991 -1% | $213,353 +1.9% |
| 2003 | $3,022 +1.9% | $209,375 +2.4% |
| 2002 | $2,967 +6.9% | $204,468 +1.6% |
| 2001 | $2,774 +18.6% | $201,248 +19.3% |
| 2000 | $2,340 | $168,687 |
Neighborhood: 34229
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Nearby schools
GreatSchools rating
- 8/10Laurel Nokomis SchoolGrades: PK-8Distance: 4.7 mi
- 7/10Venice Senior High SchoolGrades: 9-12Distance: 6.5 mi
Schools provided by the listing agent
- Elementary: Laurel Nokomis Elementary
- Middle: Sarasota Middle
- High: Venice Senior High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Florida
- Sarasota County
- Osprey
- 34229
- 186 WINDWARD DRIVE