- 4 beds
- 3 baths
- 2,856 sq ft
5305 Windy Grove Dr, Wimauma, FL, 33598
Community: Southshore Bay
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Home type
Single family
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Year built
2022
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Lot size
10,420 sq ft
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Price per sq ft
$223
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Taxes
$8463 / Yr
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HOA fees
$436 / Mo
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Last updated
Today
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Views
3
Questions? Call us: (727) 513-2427
Overview
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
Interior
Appliances
- Built-In Oven, Cooktop, Dishwasher, Disposal, Gas Water Heater, Microwave, Range, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
Bedrooms
- Bedrooms: 4
Bathrooms
- Total bathrooms: 3
- Full baths: 3
Laundry
- Gas Dryer Hookup
- Inside
- Laundry Room
- Washer Hookup
Cooling
- Central Air
Heating
- Electric, Natural Gas
Features
- Built-in Features, Ceiling Fan(s), Coffered Ceiling(s), Crown Molding, High Ceilings, In-Wall Pest Control, Kitchen/Family Room Combo, Living/Dining Room, Open Floorplan, Main Level Primary, Smart Home, Solid Surface Counters, Solid-Wood Cabinets, Split Bedrooms, Stone Counters, Thermostat, Tray Ceiling(s), Walk-In Closet(s), Window Treatments
Levels
- One
Size
- 2,856 sq ft
Exterior
Private Pool
- No
Patio & Porch
- Covered, Front Porch, Rear Porch, Screened
Roof
- Tile
Garage
- Attached
- Garage Spaces: 3
- Driveway
- Garage Door Opener
- Ground Level
- Oversized
Carport
- None
Year Built
- 2022
Lot Size
- 0.25 acres
- 10,420 sq ft
Waterfront
- No
Water Source
- Public
Sewer
- Public Sewer
Community Info
HOA Information
- Association Fee: $436
- Association Fee Frequency: Monthly
- Association Fee 2: $272
- Association Fee Includes: Cable TV, Clubhouse, Fitness Center, Gated, Lobby Key Required, Maintenance, Pickleball, Pool, Recreation Facilities, Security, 24 Hour Guard, Cable TV, Pool(s), Internet, Maintenance Structure, Maintenance Grounds, Association Management, Private Roads, Recreation Facilities, Security
Taxes
- Annual amount: $8,462.51
- Tax year: 2025
Senior Community
- Yes
Features
- Association Recreation - Owned, Clubhouse, Community Mailbox, Deed Restrictions, Dog Park, Fitness Center, Gated, Guarded Entrance, Golf Carts Permitted, Pool, Restaurant, Sidewalks, Street Lights
Location
- City: Wimauma
- County/Parrish: Hillsborough
- Township: 32
Listing courtesy of: Lori Rivero, RE/MAX REALTY UNLIMITED, 813-684-0016
MLS ID: TB8508434
Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of May 19, 2026, 06:37am PDT. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS.
Southshore Bay Real Estate Agent
Want to learn more about Southshore Bay?
Here is the community real estate expert who can answer your questions, take you on a tour, and help you find the perfect home.
Get started today with your personalized 55+ search experience!
Want to learn more about Southshore Bay?
Get in touch with a community real estate expert who can answer your questions, take you on a tour, and help you find the perfect home.
Get started today with your personalized 55+ search experience!
Homes Sold:
55+ Homes Sold:
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Community Key Facts
Age Restrictions
- 55+
Amenities & Lifestyle
- See Southshore Bay amenities
- See Southshore Bay clubs, activities, and classes
Homes in Community
- Total Homes: 655
- Home Types: Single-Family, Attached
Gated
- Yes
Construction
- Construction Dates: 2017 - Present
- Builder: Lennar, WCI, D.R. Horton
Similar homes in this community
Popular cities in Florida
The following amenities are available to Southshore Bay - Wimauma, FL residents:
- Clubhouse/Amenity Center
- Restaurant
- Fitness Center
- Outdoor Pool
- Billiards
- Walking & Biking Trails
- Tennis Courts
- Pickleball Courts
- Bocce Ball Courts
- Volleyball Court
- Parks & Natural Space
- Outdoor Patio
- Pet Park
- Multipurpose Room
There are plenty of activities available in Southshore Bay. Here is a sample of some of the clubs, activities and classes offered here.
- Billiards
- Bocce Ball
- Pickleball
- Tennis
- Volleyball




