5305 WINDY GROVE DRIVE | Wimauma

$636,000 | 4 Beds | 3 Baths (3 Full) | 2,856 Sq. Ft.

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 StellarMLS TB8508434

Directions to property: From 674 headed East turn right onto Lagoon Shore Blvd. Enter the community on the GUEST lane and provide the guard with your business card and property address. Once through the gate proceed straight on Lagoon Shore Blvd, continue around round about. The Lagoon will be on your right, turn left onto Sailor Pines. You will need to enter your gate code provided with your showing confirmation. At the stop sign (the clubhouse is in front of you) turn right onto Scuba Crest. Follow Scuba Crest down and proceed straight around the round about. At the next intersection Windy Grove turn right. Home is second on the right, 3 car garage

MLS Listing ID: 
StellarMLS TB8508434
Basic Property Information
Fields containing basic information about the property.
Property Type: 
Residential
Property Sub Type: 
Single Family Residence
Primary Market Area: 
Wimauma
Address: 
5305 WINDY GROVE DRIVE, Wimauma, FL 33598, US
County: 
Hillsborough
Community Information
Subdivision: 
MEDLEY AT SOUTHSHORE BAY
Association Fee: 
$436
Building Details
Details about the building on a property.
Year Built: 
2022
New Construction: 
0
Living Area: 
2,856
Interior: 
Coffered Ceiling(s), Crown Molding, In Wall Pest System, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Tray Ceiling(s), Walk-In Closet(s),
Construction
Construction Materials: 
Block, Concrete, Stucco
Foundation Details: 
Slab
Roof: 
Tile
Exterior Features: 
Hurricane Shutters, Lighting, Sidewalk, Sliding Doors, Sprinkler Metered
Porch: 
Covered, Front Porch, Rear Porch, Screened
Room Details
Details about the rooms in the building.
Total Rooms: 
11
Total Bedrooms: 
4
Total Bathrooms: 
3
Total Full-Bathrooms: 
3
Total Half-Bathrooms: 
0
Utilities
Information about utilities available on the property.
Heating System: 
Electric, Natural Gas
Cooling System: 
Central Air
Water Source: 
Public
Sewer: 
Public Sewer
Lot/Land Details
Details about the lots and land features included on the property.
Acres: 
0.25
Lot Size (Area): 
10,420
Lot Size (Dimensions): 
89 x 120
Waterfront: 
0
Lot Features
Parking Type: 
Driveway, Garage Door Opener, Ground Level, Oversized
Public Record
Parcel Number: 
U173220C6K00003600004.0
Annual Tax: 
$8,462.51
Property Zoning: 
PD
Listing Dates
Dates involved in the transaction.
Listing Entry Date/Time: 
5/18/2026
Listing Participants
Participants (agents, offices, etc.) in the transaction.
Listing Agent Name: 
Lori Rivero
Listing Co-Agent Name: 
Adam Rivero
Listing Office Name: 
RE/MAX REALTY UNLIMITED
Listing Co-Office Name: 
RE/MAX REALTY UNLIMITED