


5305 WINDY GROVE DRIVEWIMAUMA, FL 33598
Single Family · 4 Beds · 3 Full Baths · 2,856 Sq. ft. | 0.25 Acres5305 WINDY GROVE DRIVE Overview
- Time on Site:
- 43 days
- Visits:
- 0
Welcome to luxury living redefined at 5305 Windy Grove Drive, located in the premier 55+ gated community of Medley at Southshore Bay. Perfectly positioned on a large EXECUTIVE Conservation View PREMIUM Lot, this exceptional 4-bedroom, 3-bath residence offers the space, privacy, and upscale finishes today’s buyers have been searching for — all wrapped into one stunning Florida retreat. From the moment you enter, the attention to detail is undeniable. CROWN Molding, CUSTOM Architectural Ceiling details, DESIGNER lighting, and elegant finishes create a sophisticated yet welcoming atmosphere throughout the home. The expansive open-concept layout was designed for both entertaining and everyday comfort, seamlessly blending luxury with functionality. At the heart of the home is a truly showstopping GOURMET kitchen featuring QUARTZ countertops, upgraded cabinetry, a gas cooktop, CUSTOM BACKSPLASH details, an oversized island, and a FULLY CUSTOMIZED SHOWPIECE PANTRY featuring built-in wine racks, a wine refrigerator, and designer finishes that elevate the space with beauty and function. There is a SECOND pantry EQUALLY SPACIOUS and is the perfect hidden storage for countertop appliances and everyday dry goods. This rare dual-pantry setup offers the kind of luxury and functionality buyers dream about but rarely find. The spacious primary suite is a private sanctuary complete with a CUSTOM BOUTIQUE-STYLE walk-in closet that feels more like a high-end dressing room than a traditional closet. Additional bedrooms and baths provide comfort and flexibility for guests, hobbies, office space, or multigenerational living. Tucked away upstairs, you’ll find a rare and incredibly versatile 16x10 bonus storage space — the kind of feature buyers never realize they need until they see it. Whether you envision a climate-controlled holiday storage area, hobby room, private office, fitness nook, craft space, “man cave,” or an organized spot for all the extras that usually take over the garage, this hidden gem adds valuable flexibility and function to the home. In a world where storage is everything, this is a standout feature you simply don’t find every day. Step outside to the OVERSIZED screened lanai designed for true indoor-outdoor Florida living. With multiple seating areas, beautiful privacy, and plenty of room to relax or entertain, this outdoor space becomes an extension of the home itself. The oversized lot provides added breathing room and a more private setting rarely found in community living. Beyond the home, residents enjoy the unmatched Medley lifestyle including a gated golf-cart-friendly community, resort-style clubhouse, fitness center, pickleball courts, social events, and access to the incredible crystal lagoon with guest passes for family and friends. HOA benefits also include lawn maintenance, high-speed internet, cable, and premium streaming services including Disney+, Hulu, Paramount+, and more — creating both luxury and convenience in one simplified lifestyle package
5305 WINDY GROVE DRIVE Facts & Features
- Type Single Family
- Sq. ft. 2,856
- Price/Sq.ft. $223
- Lot 0.25 Acres
Details
General
Association/HOA
- Association Amenities: Cable TV,Clubhouse,Fitness Center,Gated,Lobby Key Required,Maintenance,Pickleball Court(s),Pool,Recreation Facilities,Security
- Association Fee: 435.88
- Association Fee 2: 272
- Association Fee 2 Frequency: Quarterly
- Association Fee Frequency: Monthly
- Association Fee Includes: Guard - 24 Hour,Cable TV,Pool,Internet,Maintenance Structure,Maintenance Grounds,Management,Private Road,Recreational Facilities,Security
- Association Name: Castle Management - Medley HOA
- Association Name 2: Southshore Bay
- Association: Yes
Green Features
- Green Indoor Air Quality: HVAC UV/Elec. Filtration
Building Information
- Builder Model: RAY
- Builder Name: Lennar
- New Construction: No
- Year Built: 2022
Location/Region
- Country: US
- County Or Parish: Hillsborough
- MLS Area Major: 33598 - Wimauma
- Subdivision Name: MEDLEY AT SOUTHSHORE BAY
- Township: 32
Community/Development
- Community Features: Association Recreation - Owned,Clubhouse,Community Mailbox,Deed Restrictions,Dog Park,Fitness Center,Gated Community - Guard,Gated Community - No Guard,Golf Carts OK,Pool,Restaurant,Sidewalks,Street Lights
Tax Information
- Tax Annual Amount: 8462.51
- Tax Year: 2025
General Information
- Furnished: Negotiable
- Listing Terms: Cash,Conventional,FHA,VA Loan
- Ownership: Fee Simple
- Parcel Number: U-17-32-20-C6K-000036-00004.0
- Pets Allowed: Cats OK,Dogs OK,Number Limit
- Property Condition: Completed
- Property Sub Type: Single Family Residence
- Property Type: Residential
- Senior Community: Yes
- Special Listing Conditions: None
- Zoning: PD
Interior
Parking Information
- Garage Spaces: 3
- Garage: Yes
Beds/Baths
- Bathrooms Full: 3
- Bathrooms Half: 0
- Bathrooms Total: 3
- Bedrooms Total: 4
Building Interior
- Building Area Source: Public Records
- Building Area Total: 4261
- Building Area Units: Square Feet
General Information
- Appliances: Built-In Oven,Cooktop,Dishwasher,Disposal,Gas Water Heater,Microwave,Range,Refrigerator,Tankless Water Heater,Washer,Wine Refrigerator
- Cooling: Central Air
- Fireplace: No
- Flooring: Ceramic Tile,Luxury Vinyl
- Foundation Details: Slab
- Heating: Electric,Natural Gas
- Interior Features: Built-in Features,Ceiling Fans(s),Coffered Ceiling(s),Crown Molding,High Ceilings,In Wall Pest System,Kitchen/Family Room Combo,Living Room/Dining Room Combo,Open Floorplan,Primary Bedroom Main Floor,Smart Home,Solid Surface Counters,Solid Wood Cabinets,Split Bedroom,Stone Counters,Thermostat,Tray Ceiling(s),Walk-In Closet(s),Window Treatments
- Laundry Features: Gas Dryer Hookup,Inside,Laundry Room,Washer Hookup
- Levels: One
- Living Area: 2856
- Living Area Source: Public Records
- Living Area Units: Square Feet
- Security Features: Fire Alarm,Gated Community,Security System
- Stories Total: 1
- Window Features: Shades,Shutters,Window Treatments
Exterior
Parking Information
- Parking Features: Driveway,Garage Door Opener,Ground Level,Oversized
Lot Information
- Additional Parcels: No
- Lot Features: Conservation Area,Landscaped,Level
- Lot Size Acres: 0.25
- Lot Size Dimensions: 89x120
- Lot Size Square Feet: 10450
- Road Responsibility: Private Maintained Road
- Road Surface Type: Asphalt,Paved
- Vegetation: Trees/Landscaped
- Water Source: Public
Waterfront/View
- View: Park/Greenbelt
- Waterfront: No
Building Exterior/Construction
- Architectural Style: Mediterranean
- Attached Garage: Yes
- Construction Materials: Block,Concrete,Stucco
- Direction Faces: South
- Patio And Porch Features: Covered,Front Porch,Rear Porch,Screened
- Roof: Tile
General Information
- Carport: No
- Exterior Features: Hurricane Shutters,Lighting,Sidewalk,Sliding Doors,Sprinkler Metered
- Other Structures: Storage
- Pool Private: No
- Sewer: Public Sewer
- Utilities: Cable Available,Electricity Connected,Natural Gas Connected,Public,Sewer Connected,Underground Utilities,Water Connected
Room Information
Room: Bathroom 2
- Level: First
- Features: Garden Bath
Room: Bathroom 3
- Level: First
- Features: Double Vanity
Room: Bedroom 2
- Level: First
- Features: Ceiling Fan(s)
Room: Bedroom 3
- Level: First
- Features: Jack & Jill Bathroom
Room: Bedroom 4
- Level: First
- Features: Jack & Jill Bathroom
Room: Dining Room
- Level: First
Room: Kitchen
- Level: First
- Features: Kitchen Island
Room: Laundry
- Level: First
Room: Living Room
- Level: First
- Features: Ceiling Fan(s)
Room: Primary Bathroom
- Level: First
- Features: Built-In Shower Bench
Room: Primary Bedroom
- Level: First
- Features: En Suite Bathroom
5305 WINDY GROVE DRIVE Neighborhood
Community
33598 (WIMAUMA) Demographics
Schools
School data courtesy of LiveBy, Inc. School ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating.5305 WINDY GROVE DRIVE Monthly Cost
5305 WINDY GROVE DRIVE Market Data
Based on the last 30 days in this zip code
5305 WINDY GROVE DRIVE History
| Date | Value | Agent |
|---|---|---|
| 5/19/2026Source: My Florida Regional MLS | May 19, 2026 |









































































