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.
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.
Property Details
Price:
$1,047,000
MLS #:
TB8556740
Status:
Active
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
SOUTHBAY YACHT & RACQUET CLUB
Neighborhood:
34229osprey
Listed Date:
Oct 10, 2026
Finished Sq Ft:
2,134
Total Sq Ft:
3,000
Lot Size:
15,778 sqft / 0.36 acres (approx)
Year Built:
1986
See this Listing
Schools
Elementary School:
Laurel Nokomis Elementary
Middle School:
Laurel Nokomis Middle
High School:
Venice Senior High
Interior
Appliances
Dishwasher, Dryer, Microwave, Range, Range Hood, Refrigerator, Washer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Tile, Vinyl
Heating
Central
Interior Features
Ceiling Fan(s), Eating Space In Kitchen, Open Floorplan, Primary Bedroom Main Floor, Vaulted Ceiling(s)
Laundry Features
Inside, Laundry Room
Levels
One
Exterior
Attached Garage YN
1
Community Features
Boat Slip, Dock, Intracoastal Waterway, Marina, Waterfront, Clubhouse, Deed Restrictions, Fitness Center, Golf Carts OK, Park, Playground, Pool, Sidewalks, Tennis Court(s)
Construction Materials
Block
Covered Spaces
2
Direction Faces
East
Exterior Features
French Doors, Hurricane Shutters, Irrigation System, Lighting, Outdoor Shower, Private Mailbox, Sliding Doors
Garage Spaces
2
Roof
Tile
Waterfront Features
Waterfront
Financial
HOA Fee
$657
HOA Fee Frequency
Quarterly
HOA Name
Southbay Yacht & Racquet Club / Rachelle Freed
HOA Phone
941-966-4237
Tax Year
2025
Taxes
$3,959
Map
Community
- Address102 WINDWARD DRIVE OSPREY FL
- SubdivisionSOUTHBAY YACHT & RACQUET CLUB
- CityOSPREY
- CountySarasota
- Zip Code34229
Subdivisions in OSPREY
- ACREAGE & UNREC
- ARBORS
- BAY ACRES – RESUB
- BAY OAKS ESTATES
- BAY OAKS ESTATES UNIT 1
- BAY STREET VILLAGE
- BAYPOINTE VISTA 1
- BAYPOINTE VISTA 2
- BAYSIDE
- BISHOPS COURT AT OAKS PRESERVE
- BISHOPSCOURT AT THE OAKS PRESERVE
- BISHOPSCOURT TOWNHOME ONE
- BLACKBURN HARBOR RESIDENCES
- BLACKBURN HARBOR WATERFRONT VILLAS
- BLACKBURN HARBOR WATERFRONT VILLAS PHASE 2
- BLACKBURN POINT WOODS
- CASEY KEY
- CORDES COVE
- DRY SLIPS AT BELLAGIO VILLAGE
- EDGEWATER/HIDDEN BAY PH 1 BLDG
- EDGEWATER/HIDDEN BAY PH 3
- EDGEWATER/HIDDEN BAY PH II BLD
- HARMS SUB
- HERON BAY CLUB SEC I
- HERON HOUSE
- HIDDEN BAY
- MERIDIAN AT THE OAKS
- MERIDIAN AT THE OAKS PRESERVE
- NORTH CREEK ESTATES
- OAKS
- OAKS 2 PH 1
- OAKS 2 PH 2
- OAKS 2 PH 4-A
- OAKS 2 PH 4-C PT 3
- OAKS 2 PHASE 2
- OAKS 3 PH 1
- OGBURNS T B ADD
- OSPREY EXECUTIVE PARK
- OSPREY HARBOR VILLAGE
- OSPREY PARK 2
- PALMS/CASEY KEY
- PARK TRACE ESTATES
- PHASE 1 OF BAY STREET
- PHASE 2 OF BAY STREET
- PINE RANCH
- PINE RANCH EAST
- PINE RUN I
- PINE RUN II
- PINE RUN III
- RIVENDELL
- RIVENDELL THE WOODLANDS
- RIVENDELL WOODLANDS
- SARABAY ACRES
- SAUNDERS V A RESUB
- SIESTA REV RESUB OF PT
- SORRENTO SHORES
- SOUTH CREEK
- SOUTHBAY YACHT & RACQUET CLUB
- THE OAKS
- THE OAKS BAYSIDE
- TOWNS-END SHORES
- VILLAS AT BELLAGIO HARBOR VILLAGE
- VILLAS/HARBOR VILLAGE
- WILLOWBEND PH 1
- WILLOWBEND PH 3
- WILLOWBEND PH 4
- WILLOWBEND PHASE 3
- WINDSOR LODGE AT THE OAKS
Market Summary
Current real estate data for Single Family in OSPREY as of Oct 16, 2026
71
Single Family Listed
161
Avg DOM
480
Avg $ / SqFt
$1,575,079
Avg List Price
Property Summary
- Located in the SOUTHBAY YACHT & RACQUET CLUB subdivision, 102 WINDWARD DRIVE OSPREY FL is a Single Family for sale in OSPREY, FL, 34229. It is listed for $1,047,000 and features 3 beds, 3 baths, and has approximately 2,134 square feet of living space, and was originally constructed in 1986. The current price per square foot is $491. The average price per square foot for Single Family listings in OSPREY is $480. The average listing price for Single Family in OSPREY is $1,575,079. To schedule a showing of MLS#tb8556740 at 102 WINDWARD DRIVE in OSPREY, FL, contact your CENTURY 21 Carioti agent at 2392986550.
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Courtesy of FUTURE HOME REALTY INC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 102 WINDWARD DRIVE
OSPREY, FL
