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$636,000 Just Listed
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Property Description
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
Full Property Details
Full Property Details for 5305 Windy Grv Dr
General
- Price: $636,000
- HOA FEE: $436/month
- Taxes: $8,462 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: TB8508434
- Updated: 5/19/2026
- Added to Site: 1 day(s) ago
Rental Information
- Min. Lease: 8-12 Months
Interior
- Number of Rooms: 11
- Interior Features: Built-in Features, Ceiling Fan(s), Coffered Ceiling(s), Crown Molding, High Ceilings, In Wall Pest System, Kitchen and Family Room Combination, 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
- Furnishings: Negotiable
- Flooring: Ceramic Tile, Luxury Vinyl
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 3
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Gas Dryer Hookup, Inside, Laundry Room, Washer Hookup
Additional Information
- Shared Amenities: Cable TV, Clubhouse, Fitness Center, Gated, Lobby Key Required, Maintenance, Pickleball Court(s), Pool, Recreation Facilities, Security
- Security/Safety: Fire Alarm, Gated Community, Security System
Exterior
- Exterior Features: Hurricane Shutters, Lighting, Sidewalk, Sliding Doors, Sprinkler Metered
- Deck/Patio: Covered, Front Porch, Rear Porch, Screened
- Porch/Patio/Deck: Covered, Front Porch, Rear Porch, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Covered Spaces: 3
- Parking Features: Driveway, Garage Door Opener, Ground Level, Oversized
Location
- Area: 33598 - Wimauma
- County: Hillsborough
- Development Name: 33598 - Wimauma
- Subdivision: MEDLEY AT SOUTHSHORE BAY
- 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
- Direction Faces: South
Community
- Community Name: 33598 - Wimauma
- 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
- Optional Amenities: Cable TV, Clubhouse, Fitness Center, Gated, Lobby Key Required, Maintenance, Pickleball Court(s), Pool, Recr
- Association: Yes
- Assoc. Name: Castle Management - Medley HOA
- Assoc. Fees Include: 24-Hour Guard, Cable TV, Community Pool, Internet, Maintenance Structure, Maintenance Grounds, Manager, Pool Maintenance, Private Road, Recreational Facilities, Security
- Number of Pets: 2
- Pet Restrictions: Buyer to Verify Current Restrictions with HOA
- Adult Community: Yes
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Electric, Natural Gas
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Cable TV Available, Electricity Connected, Natural Gas Connected, Public, Sewer Connected, Street Lights, Underground Utilities, Water Connected
Structural Information
- Architectural Info: Mediterranean
- Architectural Style: Mediterranean
- Builder: Lennar
- Exterior Const.: Block, Concrete, Stucco
- Roof: Tile
- Windows: Shades, Shutters, Window Treatments
- Stories/Levels: One
- Square Feet: 2,856
- Sq. Ft. Source: Public Records
- Year Built: 2022
Additional Structures
- Other Structures: Storage
Lot Features
- Property View: Park/Greenbelt
- Lot Size (Acres): 0.25
- Lot Size (Sq. Ft.): 10,420
- Lot Size: 10420
- Lot Dimensions: 89 x 120
- Street/Road Desc.: Asphalt, Paved
Green Features
- Indoor Air Quality: HVAC UV/Elec. Filtration
Financial Considerations
- Association Fee: $436
- Assoc Fee Freq.: Monthly
- Assoc Fee Desc.: Required
- CDD: Yes
- Tax Amount: $8,462.51
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: FOREST BROOKE ACTIVE ADULT PH 4 5B 6B 8B AND COLLECTOR RD 2ND EXT PH 2 LOT 4 BLOCK 36
- Flood Zone Info: X
- APN: U173220C6K00003600004.0
- Property ID: U173220C6K00003600004.0
- Block/Lot/Section: 36
Listed by Re/Max Realty Unlimited
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Schools
Schools serving 5305 Windy Grv Dr
School District:Hillsborough County School District
| Name | Grades | Distance |
|---|---|---|
Reddick Elementary School 325 West Lake Drive, Wimauma, FL 33598 | K-5 | 1.5 mi |
Shields Middle School 15732 Beth Shields Way, Ruskin, FL 33573 | 6-8 | 4.1 mi |
Jule F Sumner High School 10650 County Road 672, Riverview, FL 33579 | 9-12 | 5.1 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 5305 Windy Grv Dr
Date
Details
Price
Change
Source
5/18/2026
Listed
$636,000
17.65%
MLS
11/02/2022
Sold
$540,600
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 5305 Windy Grv Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$8,463
6%
$431,845
—
2024
$7,999
-9%
$431,845
-7%
2023
$8,810
943%
$465,560
5442%
2022
$845
—
$8,400
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 5305 Windy Grv Dr
5305 Windy Grove Drive, Wimauma, FL 33598 (MLS# TB8508434) is a Single Family property with 4 bedrooms and 3 full bathrooms. 5305 Windy Grove Drive is currently listed for $636,000 and was received on May 18, 2026. Want to learn more about 5305 Windy Grove Drive? Do you have questions about finding other Single Family real estate for sale in Wimauma? You can browse all Wimauma real estate or contact a Coldwell Banker agent to request more information.

