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186 Windward Drive

Osprey, FL 34229
  • $749,900
  • STATUS: Active
  • ON SITE: 13 Days
  • MLS #: N6142087
UPDATED: 38 min ago
$749,900
  • 3
    BEDS
  • 0.3
    ACRES
  • 2
    BATHS
  • 0
    1/2 BATHS
  • 2,505
    SQFT
  • $299
    $/SQFT
Type:
Single-Family Home
Built:
1983
County:
Area:

School Information

Elementary School:
Middle School:
High School:

Description

Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2-bath residence offers a split bedroom layout, unique community amenities, NEW ROOF in 2022, 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. Roof was replaced in 2022 & AC was installed in 2016. The entire house has also been replumbed! 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! **The street behind this house (Blackburn Point Rd.) is a fairly quiet two lane Rd. That's the road you can take your golf cart to Casey Key Fish House & Tiki Bar!**There is marina space available and fees range between $169-$705 per quarter.**

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© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-01-22T14:47:09.063.
www.gulfcoastregroup.com/homes/171905347
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186 Windward Drive Osprey, FL 34229

  • Price: $749,900
  • Status: Active
  • On Site: 13 Days
  • Updated: 38 min ago
  • MLS #: N6142087
3
Beds
2
Baths
0
½ Baths
0.3
Acres
2,505
SQFT
$299
$/SQFT
1983
Built
Neighborhood:
Southbay Yacht & Racquet Club
County:
Sarasota
Area:
Osprey
Elementary School:
Laurel Nokomis Elementary
Middle School:
Sarasota Middle
High School:
Venice Senior High
Property Description
Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2-bath residence offers a split bedroom layout, unique community amenities, NEW ROOF in 2022, 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. Roof was replaced in 2022 & AC was installed in 2016. The entire house has also been replumbed! 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! **The street behind this house (Blackburn Point Rd.) is a fairly quiet two lane Rd. That's the road you can take your golf cart to Casey Key Fish House & Tiki Bar!**There is marina space available and fees range between $169-$705 per quarter.**
Exterior Features

Attached Garage Yn Yes Carport Yn No Construction Materials BlockStucco Covered Spaces 2 Direction Faces South Exterior Features Irrigation SystemLightingPrivate MailboxRain GuttersSliding Doors Foundation Details Slab Garage Dimensions 21x22 Lot Features Corner LotLandscaped Open Parking YN Yes Parking Features DeededDrivewayGarage Door OpenerOff Street Patio And Porch Features CoveredPatioScreened Pool Private Yn No Road Frontage Type Street Paved Road Surface Type PavedAsphalt Roof Tile Spa YN No View Garden Water Access Intracoastal WaterwayMarina Water Access Yn Yes Water Extras Yn No Water View Yn No Waterfront Feet Total 0 Waterfront Yn No

Interior Features

Additional Rooms Bonus RoomFamily Room Appliances DishwasherDryerElectric Water HeaterMicrowaveRangeRefrigeratorWasher Building Area Total 3298 Cooling Central Air Cooling YN Yes Fireplace Yn No Flooring Hardwood Furnished Unfurnished Heating Central Heating YN Yes Interior Features Cathedral Ceiling(s)Ceiling Fan(s)High CeilingsKitchen/Family Room ComboLiving Room/Dining Room ComboPrimary Bedroom Main FloorSplit BedroomThermostatVaulted Ceiling(s)Walk-In Closet(s) Laundry Features InsideLaundry Room Levels One Rooms Primary Bedroom (Ceiling Fan(s)En Suite BathroomWalk-In Closet(s)) Kitchen (Breakfast Bar) Family Room (Ceiling Fan(s)) Primary Bathroom (Built-In ShelvingBuilt-In Shower BenchEn Suite BathroomShower No TubSingle VanitySteam ShowerStone CountersWindow/Skylight in BathLinen Closet) Dining Room Dinette (Ceiling Fan(s)) Living Room (Ceiling Fan(s)) Bedroom 1 (Ceiling Fan(s)Walk-In Closet(s)) Bathroom 2 (Built-In ShelvingShower No TubSingle VanitySteam ShowerStone Counters) B Sewer Public Sewer Stories Total 1 Water Source Public

Property Features

Additional Lease Restrictions Please see HOA docs for more information Approval Process Please see HOA docs for more information Association Amenities Basketball CourtClubhouseFitness CenterParkPickleball Court(s)PlaygroundPoolTennis Court(s) Association Approval Required Yn No Association Fee 613 Association Fee Frequency Quarterly Association Fee Includes Common Area TaxesCommunity PoolEscrow Reserves FundFidelity BondManagerPool Maintenance Association Fee Monthly Amount 204.33 Association Fee Requirement Required Association Yn Yes Cdd Yn No Community Features Boat SlipDockIntracoastal WaterwayMarinaClubhouseDeed RestrictionsFitness CenterGolf Carts OKParkPlaygroundPoolSidewalksTennis Court(s) Down Payment Resource Yes Flood Zone Code X Garage Yn Yes Homestead Yn No Lease Considered YN Yes Lease Restrictions YN Yes Listing Terms CashConventionalFHAVA Loan Minimum Lease 3 Months New Construction Yn No Ownership Fee Simple Pets Allowed Yes Property Sub Type Single Family Residence Senior Community Yn No Special Listing Conditions None Sw Subdiv Community Name Southbay Yacht & Racquet Club Tax Annual Amount 7566.37 Total Annual Fees 2452 Total Monthly Fees 204.33 Utilities BB/HS Internet AvailableCable AvailableCable ConnectedElectricity AvailableElectricity ConnectedSewer AvailableSewer ConnectedWater AvailableWater Connected Yrs Of Owner Prior To Leasing Re Yes Zoning RSF2


Listing information © 2026 My Florida Regional MLS DBA Stellar MLS..
Listing provided courtesy of KELLER WILLIAMS ON THE WATER S: 941-803-7522.



© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-01-22T14:47:09.063.
 
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