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  • Home type

    Single family

  • Year built

    2022

  • Lot size

    10,420 sq ft

  • Price per sq ft

    $223

  • Taxes

    $8463 / Yr

  • HOA fees

    $436 / Mo

  • Last updated

    Today

  • 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

Stellar

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.


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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.

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Homes Sold:

55+ Homes Sold:

Sold for this Community:

Avg. Response Time:

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Community Key Facts

Southshore Bay

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

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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:

Sold for this Community:

Avg. Response Time:

Global - Lead Form - Buyer Only
*55places does not provide or maintain community HOA information.
By requesting more information, you agree that 55places placeholder may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com's Privacy Policy and Terms of Use.

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