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$1,047,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,134 Sq. Ft.
  • Updated 3 hours ago
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Experience refreshed coastal living in Southbay Yacht and Racquet Club. This beautifully updated pool home pairs inviting interiors with outdoor spaces made for relaxing and entertaining. Fresh exterior paint and refreshed landscaping with new sod and palm trees create a welcoming arrival. Inside, new vinyl flooring flows through the living spaces and bedrooms, complemented by large format tile in the bathrooms. High ceilings and a decorative beam add character to the open living area. The redesigned kitchen features new cabinetry, quartz countertops with a waterfall detail, stainless steel appliances, a range hood, pendant lighting, illuminated shelving and a walk in pantry. The home offers three bedrooms, two full bathrooms and one half bathroom. The primary retreat offers two newly built closets and a beautifully remodeled bathroom with a spacious double vanity, freestanding soaking tub, separate shower, new fixtures and mirrors. The remodeled guest bathroom features a large double vanity, coordinating tile and updated shower fixtures. The layout features dual primary bedrooms, with the second offering a generous walk in closet, an attached half bathroom and exterior access. Practical updates complement the refreshed interiors, with hurricane rated windows throughout the home and hurricane shutters for added storm protection. New ceiling fans in the bedrooms, an interior laundry room with a new washer and dryer combo, and an oversized garage with an epoxy painted finish add everyday convenience. Step outside to the screened pool and covered lanai, with a new outdoor shower for rinsing off after a swim. An expanded paver area beyond the lanai with a built in outdoor fireplace offers another inviting space to relax and entertain. Enjoy Southbay Yacht and Racquet Club's waterfront lifestyle, featuring a community marina with Intracoastal access, a community pool, tennis, pickleball, a fitness center and clubhouse. From time on the water to relaxing evenings by your own pool, this home brings together beautifully updated spaces and an active coastal lifestyle. No CDD.

Full Property Details for 102 Windward Dr

General

  • Price: $1,047,000
  • HOA FEE: $219/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $3,959 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: TB8556740
  • Updated: Today (10/10/2026)
  • Added to Site: Today

Rental Information

  • Min. Lease: 3 Months

Interior

  • Number of Rooms: 9
  • Interior Features: Ceiling Fan(s), Eating Space In Kitchen, Open Floorplan, Primary Bedroom Main Floor, Vaulted Ceiling(s)
  • Appliances: Dishwasher, Dryer, Microwave, Range, Range Hood, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Tile, Vinyl

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Inside, Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: In Ground

Exterior

  • Exterior Features: French Doors, Hurricane Shutters, Irrigation System, Lighting, Outdoor Shower, Private Mailbox, Sliding Doors

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2

Location

  • Area: 34229 - Osprey
  • County: Sarasota
  • Development Name: 34229 - Osprey
  • Subdivision: SOUTHBAY YACHT & RACQUET CLUB
  • Driving Directions: From US 41, take Blackburn Point Road. Turn left onto Southbay Drive, then immediately left onto Windward Drive. 102 Windward Drive is on the left.
  • Direction Faces: East

School Information

  • Elementary School: Laurel Nokomis Elementary
  • Middle School: Laurel Nokomis Middle
  • High School: Venice Senior High

Community

  • Community Name: 34229 - Osprey
  • Community Features: Boat Slip, Dock, Intracoastal Waterway, Marina, Waterfront, Clubhouse, Deed Restrictions, Fitness Center, Golf Carts OK, Park, Playground, Pool, Sidewalks, Tennis Court(s)
  • Association: Yes
  • Assoc. Name: Southbay Yacht & Racquet Club / Rachelle Freed

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Electricity Available, Water Available

Structural Information

  • Exterior Const.: Block
  • Roof: Tile
  • Stories/Levels: One
  • Square Feet: 2,134
  • Sq. Ft. Source: Public Records
  • Year Built: 1986

Lot Features

  • Lot Size (Acres): 0.36
  • Lot Size (Sq. Ft.): 15,778
  • Lot Size: 15778
  • Street/Road Desc.: Concrete

Water Features

  • Water Front Desc.: Waterfront

Financial Considerations

  • Association Fee: $657
  • Assoc Fee Freq.: Quarterly
  • Assoc Fee Desc.: Required
  • Tax Amount: $3,959.35
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LOT 129 SOUTHBAY YACHT & RACQUET CLUB
  • Flood Zone Info: X
  • APN: 157080006
  • Property ID: 157080006

Listed by Future Home Realty Inc

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Listing agent

— 102 Windward Dr —

  • Future Home Realty Inc

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 102 Windward Dr

School District:Sarasota County School District
NameGradesDistance
Laurel Nokomis School
1900 Laurel Road East, Nokomis, FL 34275
PK-84.7 mi
Venice Senior High School
1 Indian Avenue, Venice, FL 34285
9-126.5 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 102 Windward Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/10/2026
Listed
$1,047,000
85.31%
MLS
6/04/2026
Sold
$565,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 102 Windward Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$1,062
20%
$316,155
3%
2024
$888
5%
$307,245
3%
2023
$845
4%
$298,296
6%
2021
$814
1%
$281,173
-3%
2022
$809
-1%
$289,608
4%
2021
$814
-75%
$277,291
2%
2019
$3,253
3%
$271,057
2%
2018
$3,172
1%
$266,003
2%
2017
$3,156
—
$260,532
2%
2016
$3,146
-2%
$255,173
1%
2015
$3,202
—
$253,399
1%
2014
$3,188
—
$251,388
1%
2013
$3,185
—
$247,673
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

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Listed by Future Home Realty Inc

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102 Windward Drive, Osprey, FL 34229 (MLS# TB8556740) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 102 Windward Drive is currently listed for $1,047,000 and was received on October 10, 2026. Want to learn more about 102 Windward Drive? Do you have questions about finding other Single Family real estate for sale in Osprey? You can browse all Osprey real estate or contact a Coldwell Banker agent to request more information.

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