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186 WINDWARD DRIVE OSPREY FL 34229

$749,900
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186 WINDWARD DRIVE, OSPREY, FL 34229 - MLS#MFRN6142087 186 WINDWARD DRIVE, OSPREY, FL 34229 - MLS#MFRN6142087 186 WINDWARD DRIVE, OSPREY, FL 34229 - MLS#MFRN6142087 186 WINDWARD DRIVE, OSPREY, FL 34229 - MLS#MFRN6142087

Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
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Overview of 186 Windward Dr

3 Bedrooms
2 Bathrooms
2 Car Garage
3,298 Square Feet
2,505SF Living Area
Pool:
No
Water: None
Year Built 1983
Listed For 1 Days

Don't miss this home for sale in Southbay Yacht And Racquet Club! Located in the desirable southbay yacht & racquet club, this 3-bedroom, 2-bath residence offers a split bedroom layout, unique community amenities, and plenty of room for a private pool. As you enter the home, you will be greeted by the formal living room and dining room to the left and hallway to the family room, kitchen, and dinette straight ahead. The entire interior has been professionally painted in 2025, and there is tons of natural light that flows through the many windows of this home. The kitchen is open to the family room and dinette for easy entertaining. There is also a huge bonus room toward the back of the home. Next to the family room is entrance to the hallway leading to the two guest bedrooms and guest bathroom. On the opposite side of the home, past the dining room is the spacious primary suite with generous walk-in closet and ensuite bath. The laundry room is located near the family room. Entrance to the attached 2 car garage is near the foyer. Southbay yacht & racquet club is an active lifestyle community with many social, boating, and sports activities. The clubhouse has recently been renovated and features a community pool, fitness center, ballroom, two kitchens, card room, game room, and an elevator! Additional amenities include 3 tennis courts, 4 pickle ball courts, basketball, playground, bocce, shuffleboard, and miles of walking trails and green space. The community-owned marina—with residents-only boat slips—provides direct intracoastal waterway access with no fixed bridges to the gulf. the community is welcoming and lively—perfect for families and those who enjoy an active, coastal lifestyle. This community is in the perfect location with several warm gulf beaches, downtown venice & downtown sarasota close by. The famous casey key fish house and tiki bar are just a golf cart ride away! Oscar scherer state park is across tamiami trail and pine view (#1 school in the state) is about 5 minutes away. This home is ready for you to start living the elevated southbay lifestyle!

This lovely single family home was built in 1983 and features 3 bedrooms, and 2 full bathrooms. This home for sale is 3,298 square feet, with 2,505 sq ft being air conditioned living space. The home has a 2 car garage and does not have a private swimming pool, although there is a community pool in the complex for use by residents.

Directions to this property are as follows: From The Intersection At Us 41 And Laurel Rd Take Us 41 North. Turn Left On Southbay Dr. Turn Right On Windward Dr. Property Will Be On Your Left. From The Intersection At Us 41 And Blackburn Point Rd Take Blackburn Point Rd West. Turn Left On Southbay Dr. Turn Left On Windward Dr. Property Will Be On Your Left.

Please contact your ZFC agent for more information about MLS# MFRN6142087 or any other homes for sale in Osprey or elsewhere in the Sarasota County area.

Features & Amenities

Appliances

Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer

Other Equipment

Irrigation Equipment

Cooling

Central Air

Heating

Central

Flooring

Wood

Parking

Deeded, Driveway, Garage Door Opener, Off Street

Lot Size

13130

View

Garden view

Construction Materials

Block, Stucco

Interior Features

Cathedral Ceiling(s), Ceiling Fans(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)

Furnished

Unfurnished

Exterior Features

Lighting, Private Mailbox, Rain Gutters, Sliding Doors

Lot Features

Corner Lot, Landscaped, Paved

Patio And Porch Features

Covered, Patio, Screened

Roof

Tile

Utilities

B B/H S Internet Available, Cable Available, Cable Connected, Electricity Available, Electricity Connected, Sewer Available, Sewer Connected, Water Available, Water Connected

Laundry

Inside, Laundry Room

Zoning

R S F2

Year Built

1983

Pets Allowed

Yes

Annual Real Estate Taxes

$7,566 (2025)

Legal Description

Lot 136 Southbay Yacht & Racquet Club

Property Type

Single Family Home

HOA Fees

$613 /Quarterly

Association Fee Includes

Common Area Taxes, Pool, Escrow Reserves Fund, Fidelity Bond, Management

Association Amenities

Basketball Court, Clubhouse, Fitness Center, Park, Pickleball Court(s), Playground, Pool, Tennis Court(s)

Community Features

Clubhouse, Deed Restrictions, Fitness Center, Golf Carts O K, Park, Playground, Pool, Sidewalks, Tennis Court(s)

Direction Faces

South

MLS Number

MFRN6142087

Universal Property Id

U S-12115-N-0157070011-R-N

Days On Market

1

Community Name

Southbay Yacht & Racquet Club

Property Manager

Judy Brown (941)966-4237

186 Windward Dr Price Calculator

Get Mortgage Quote For This Home

The payment calculator figures for 186 Windward Dr should be used as an estimate only. Loan terms including interest rate, and required downpayment will vary with each lender and/or individual. RE taxes for this home for sale are estimated based on the actual property taxes for this property for the tax year 2025 which are $7,566 but will likely change when this home sells. These estimations are calculated from a list price of $749,900 and a 25% down payment and do not include homeowners insurance which will vary greatly depending on the home characteristics and location.

Recent Home Sales near 186 Windward Dr

Address Sale Price Bed Bth Size Location Sale Date
No comps found for this property

MLS# MFRN6142087 Listing History

01/06/2026 Listed for sale by KELLER WILLIAMS ON THE WATER S with MLS# MFRN6142087 with a list price of $749,900.

Sarasota County Schools

High School

Public Transportation

Breeze Transit:

Sarasota/US-41/Venice

Breeze Transit:

Sarasota/US-41/Venice

Breeze Transit:

Sarasota/US-41/Venice

Breeze Transit:

77 Siesta Islander

Breeze Transit:

77 Siesta Islander

Open House Schedule for 186 WINDWARD DR

Jan 11
1:30 pm - 4:00 pm
This listing of 186 Windward Dr Osprey FL 34229 was last updated on 2026-01-09 15:15:17. Listing courtesy of KELLER WILLIAMS ON THE WATER S.
MLS

Map of 186 Windward Dr Osprey FL 34229

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Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
Call Me
Text Me
Email Me
When clicking Submit Request, you are registering to this website and agreeing that ZFC Real Estate, its affiliates or associated third parties may contact you, including with calls or texts by automated means. You also agree to our Terms of Use and Privacy Policy

The data relating to homes for sale or lease or other real estate for sale or for rent on the ZFC website comes in part from a cooperative data exchange program of the MLS in which this Broker participates. The real estate displayed may not be all of the homes in the database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Homes for sale that are listed by Brokers other than this Broker are marked with either the listing Broker's name or the MLS name or a logo provided by the MLS and the details page about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. ZFC, the Florida Association of Realtors and its cooperating Multiple Listing Services do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law including the fair housing act prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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