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Julia Vakulenko - Broker -

Welcome Home! TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434 TB8508434
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5305 WINDY GROVE DR, WIMAUMA, 33598



Property highlights

  • MLS#: TB8508434
  • 10,420.00 lot size Sq.Ft.
  • Year built: 2022
  • Parking spaces: 3
  • Pool: Community pool
  • Listed: 05/18/2026
  • Taxes: $8,462.51
  • Annual CDD fee (inc. in Taxes): $547.00
  • HOA fees (monthly): $435.88
  • Average Monthly Fees (not including CDD, if any): $572.21
  • Maintenance fee includes: Guard - 24 Hour, Cable TV, Pool, Internet, Maintenance Structure, Maintenance Grounds, Management, Private Road, Recreational Facilities and Security
  • Virtual Tour

Property 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

Driving directions : 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

Property Features

Rooms Dimension Description
Primary Bedroom First level , Luxury Vinyl , En Suite Bathroom
Primary Bathroom First level , Ceramic Tile , Built-In Shower Bench
Bedroom 2 First level , Ceramic Tile , Ceiling Fan(s)
Bedroom 3 First level , Luxury Vinyl , Jack & Jill Bathroom
Bedroom 4 First level , Luxury Vinyl , Jack & Jill Bathroom
Bathroom 2 First level , Ceramic Tile , Garden Bath
Bathroom 3 First level , Ceramic Tile , Double Vanity
Kitchen First level , Ceramic Tile , Kitchen Island
Dining Room First level , Ceramic Tile
Laundry First level , Ceramic Tile
Living Room First level , Ceramic Tile , Ceiling Fan(s)

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

Appliances

  • Built-In Oven
  • Cooktop
  • Dishwasher
  • Disposal
  • Gas Water Heater
  • Microwave
  • Range
  • Refrigerator
  • Tankless Water Heater
  • Washer
  • Wine Refrigerator

Heating

  • Electric
  • Natural Gas

Laundry features

  • Gas Dryer Hookup
  • Inside
  • Laundry Room
  • Washer Hookup

Air Conditioning

  • Central Air

Floor Covering

  • Ceramic Tile
  • Luxury Vinyl

Utilities

  • Cable Available
  • Electricity Connected
  • Natural Gas Connected
  • Public
  • Sewer Connected
  • Underground Utilities
  • Water Connected

Exterior features

  • Hurricane Shutters
  • Lighting
  • Sidewalk
  • Sliding Doors
  • Sprinkler Metered

Parking features

  • Driveway
  • Garage Door Opener
  • Ground Level
  • Oversized

View

  • Park/Greenbelt

Patio and porch features

  • Covered
  • Front Porch
  • Rear Porch
  • Screened

Pets restrictions

  • Buyer to Verify Current Restrictions with HOA
  • 2 pet(s) allowed
  • Extra Large (101+ Lbs.)

Architectural Style

  • Mediterranean

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

Association Amenities

  • Cable TV
  • Clubhouse
  • Fitness Center
  • Gated
  • Lobby Key Required
  • Maintenance
  • Pickleball Court(s)
  • Pool
  • Recreation Facilities
  • Security

Security Features

  • Fire Alarm
  • Gated Community
  • Security System

Construction Materials

  • Block
  • Concrete
  • Stucco

Other Structures

  • Storage

Road Surface Type

  • Asphalt
  • Paved

Property Condition

  • Completed

Roof

  • Tile

Foundation

  • Slab

Vegetation

  • Trees/Landscaped

Lot Features

  • Conservation Area
  • Landscaped
  • Level

Listing information courtesy of RE/MAX REALTY UNLIMITED

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Listing data comes from My Florida Regional MLS.