Listing provided courtesy of RE/MAX REALTY UNLIMITEDas Distributed by MLSGrid- MLS# MFRTB8508434MLS Provider

5305 WINDY GROVE DRIVEWIMAUMA, FL 33598

Single Family · 4 Beds · 3 Full Baths · 2,856 Sq. ft. | 0.25 Acres
$636,000 Active

5305 WINDY GROVE DRIVE Overview

Time on Site:
43 days
Visits:
0

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

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5305 WINDY GROVE DRIVE Facts & Features

  • Type Single Family
  • Sq. ft. 2,856
  • Price/Sq.ft. $223
  • Lot 0.25 Acres

Details

General

Association/HOA

  • Association Amenities: Cable TV,Clubhouse,Fitness Center,Gated,Lobby Key Required,Maintenance,Pickleball Court(s),Pool,Recreation Facilities,Security
  • Association Fee: 435.88
  • Association Fee 2: 272
  • Association Fee 2 Frequency: Quarterly
  • Association Fee Frequency: Monthly
  • Association Fee Includes: Guard - 24 Hour,Cable TV,Pool,Internet,Maintenance Structure,Maintenance Grounds,Management,Private Road,Recreational Facilities,Security
  • Association Name: Castle Management - Medley HOA
  • Association Name 2: Southshore Bay
  • Association: Yes

Green Features

  • Green Indoor Air Quality: HVAC UV/Elec. Filtration

Building Information

  • Builder Model: RAY
  • Builder Name: Lennar
  • New Construction: No
  • Year Built: 2022

Location/Region

  • Country: US
  • County Or Parish: Hillsborough
  • MLS Area Major: 33598 - Wimauma
  • Subdivision Name: MEDLEY AT SOUTHSHORE BAY
  • Township: 32

Community/Development

  • 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

Tax Information

  • Tax Annual Amount: 8462.51
  • Tax Year: 2025

General Information

  • Furnished: Negotiable
  • Listing Terms: Cash,Conventional,FHA,VA Loan
  • Ownership: Fee Simple
  • Parcel Number: U-17-32-20-C6K-000036-00004.0
  • Pets Allowed: Cats OK,Dogs OK,Number Limit
  • Property Condition: Completed
  • Property Sub Type: Single Family Residence
  • Property Type: Residential
  • Senior Community: Yes
  • Special Listing Conditions: None
  • Zoning: PD

Interior

Parking Information

  • Garage Spaces: 3
  • Garage: Yes

Beds/Baths

  • Bathrooms Full: 3
  • Bathrooms Half: 0
  • Bathrooms Total: 3
  • Bedrooms Total: 4

Building Interior

  • Building Area Source: Public Records
  • Building Area Total: 4261
  • Building Area Units: Square Feet

General Information

  • Appliances: Built-In Oven,Cooktop,Dishwasher,Disposal,Gas Water Heater,Microwave,Range,Refrigerator,Tankless Water Heater,Washer,Wine Refrigerator
  • Cooling: Central Air
  • Fireplace: No
  • Flooring: Ceramic Tile,Luxury Vinyl
  • Foundation Details: Slab
  • Heating: Electric,Natural Gas
  • 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
  • Laundry Features: Gas Dryer Hookup,Inside,Laundry Room,Washer Hookup
  • Levels: One
  • Living Area: 2856
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Security Features: Fire Alarm,Gated Community,Security System
  • Stories Total: 1
  • Window Features: Shades,Shutters,Window Treatments

Exterior

Parking Information

  • Parking Features: Driveway,Garage Door Opener,Ground Level,Oversized

Lot Information

  • Additional Parcels: No
  • Lot Features: Conservation Area,Landscaped,Level
  • Lot Size Acres: 0.25
  • Lot Size Dimensions: 89x120
  • Lot Size Square Feet: 10450
  • Road Responsibility: Private Maintained Road
  • Road Surface Type: Asphalt,Paved
  • Vegetation: Trees/Landscaped
  • Water Source: Public

Waterfront/View

  • View: Park/Greenbelt
  • Waterfront: No

Building Exterior/Construction

  • Architectural Style: Mediterranean
  • Attached Garage: Yes
  • Construction Materials: Block,Concrete,Stucco
  • Direction Faces: South
  • Patio And Porch Features: Covered,Front Porch,Rear Porch,Screened
  • Roof: Tile

General Information

  • Carport: No
  • Exterior Features: Hurricane Shutters,Lighting,Sidewalk,Sliding Doors,Sprinkler Metered
  • Other Structures: Storage
  • Pool Private: No
  • Sewer: Public Sewer
  • Utilities: Cable Available,Electricity Connected,Natural Gas Connected,Public,Sewer Connected,Underground Utilities,Water Connected

Room Information

Room: Bathroom 2

  • Level: First
  • Features: Garden Bath

Room: Bathroom 3

  • Level: First
  • Features: Double Vanity

Room: Bedroom 2

  • Level: First
  • Features: Ceiling Fan(s)

Room: Bedroom 3

  • Level: First
  • Features: Jack & Jill Bathroom

Room: Bedroom 4

  • Level: First
  • Features: Jack & Jill Bathroom

Room: Dining Room

  • Level: First

Room: Kitchen

  • Level: First
  • Features: Kitchen Island

Room: Laundry

  • Level: First

Room: Living Room

  • Level: First
  • Features: Ceiling Fan(s)

Room: Primary Bathroom

  • Level: First
  • Features: Built-In Shower Bench

Room: Primary Bedroom

  • Level: First
  • Features: En Suite Bathroom

5305 WINDY GROVE DRIVE Neighborhood

Community

33598 (WIMAUMA) Demographics

35
Median Age
208
Population Density (per sq. mile)
27%
College Educated
$66,709
Estimated Median Income
5,573
Estimated Total Home Owners
1,153
Estimated Total Renters
83% / 17%
Estimated Owner / Renter Divide
3
Estimated Average Household Size
Community data courtesy of LiveBy, Inc.

Schools

School data courtesy of LiveBy, Inc. School ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating.

5305 WINDY GROVE DRIVE Monthly Cost

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* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

5305 WINDY GROVE DRIVE Market Data

Based on the last 30 days in this zip code

$434,267
Average List Price
$204
Average Price per Square Foot
59
Properties Sold
115
Average Days on Market
369
Properties for Sale
Calculations provided by Reliance Network

5305 WINDY GROVE DRIVE History

Date Event Value Agent
5/19/2026Source: My Florida Regional MLS Added to Database
May 19, 2026