Back to Search
5305 Windy Grove Dr, Wimauma, FL 33598
5305 Windy Grove Dr, Wimauma, FL 33598 3D Tour
5305 Windy Grove Dr, Wimauma, FL 33598 Explore 3D Tour
5305 Windy Grove Dr, Wimauma, FL 33598
5305 Windy Grove Dr, Wimauma, FL 33598
5305 Windy Grove Dr, Wimauma, FL 33598
5305 Windy Grove Dr, Wimauma, FL 33598

5305 Windy Grove Dr Wimauma, FL 33598

$636,000

ACTIVE
Beds
4
Baths
3
Sqft
2,856
Acres
0.25
Year
2022
Days on Site
4
Property Type
Residential
Sub Type
Single Family
Per Square Foot
$223
Date Listed
May 18, 2026

Description of 5305 Windy Grove Dr, Wimauma, FL 33598

Listing details for 5305 Windy Grove Dr, Wimauma, FL 33598 : 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
Listing Updated : 05-20-2026 at 2:05 AM EDT
Listing Provided By : Lori Rivero, 813-684-0016, RE/MAX REALTY UNLIMITED
Source :

Stellar MLS as distributed by MLS GRID, MLS#: MFRTB8508434

Property History

DateEventPrice
5/18/2026
Listed for sale
$636,000
$223/sqft
Source:Stellar MLS #MFRTB8508434
Home Worth Check

Interested in 5305 Windy Grove Dr, Wimauma FL, 33598?

I agree to be contacted by Smith & Associates Real Estate via call, email, and text for real estate services. To opt out, you can reply 'stop' at any time or reply 'help' for assistance. You can also click the unsubscribe link in the emails. Message and data rates may apply. Message frequency may vary. For more information, please review our Privacy Policy.

Location of 5305 Windy Grove Dr, Wimauma, FL 33598

Google Map
Mortgage Calculator
Listing Price
Down Payment
Interest Rate

Schools Near 5305 Windy Grove Dr, Wimauma, FL 33598

Homes Similar to 5305 Windy Grove Dr, Wimauma, FL 33598

Source Logo
Based on information submitted to the MLS GRID as of 2026-05-20. 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

HomeWimaumaMedley At Southshore Bay
Popular Cities

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 consumer 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.

Listing data comes from My Florida Regional MLS DBA Stellar MLS.