$636,000
5305 Windy Grove Drive
Wimauma, FL 33598
Property type
Year built
Lot size
Price / sq ft
HOA dues
Day on market
Garage spaces
Flood zone
About this home
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
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history1 days on market
- Status: ActiveMay 19, 2026
- Listed$636,000May 18, 2026
- Price increased$636,000
Virtual Tour
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 1
- Subdivision
- Medley At Southshore Bay
- County
- Hillsborough
- Year built
- 2022
- Living area
- 2,856 sq ft
- Price/sq ft
- $223
- Building area
- 4,261 sq ft (Public Records)
- Lot size
- 10,420 sq ft
- Lot category
- 1/4 to less than 1/2
- Flood zone
- X (12057C0680H)
- Garage
- 3 spaces
- Annual taxes
- $8,463 (2025)
- Parcel #
- U-17-32-20-C6K-000036-00004.0
- Zoning
- PD
- MLS #
- TB8508434
Interior Details
- Bedrooms
- 4
- Full bathrooms
- 3
- Flooring
- Ceramic Tile, Luxury Vinyl
- Appliances
- Built-In Oven, Cooktop, Dishwasher, Disposal, Gas Water Heater, Microwave, Range, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
- 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
- Gas Dryer Hookup, Inside, Laundry Room, Washer Hookup
- Stories / Levels
- One
- Direction faces
- South
Heating & Cooling
- Heating
- Electric, Natural Gas
- Cooling
- Central Air
Parking
- Garage spaces
- 3
- Attached garage
- Yes
- Parking features
- Driveway, Garage Door Opener, Ground Level, Oversized
HOA & Financial
- HOA fee
- $436 / Monthly
- Monthly HOA
- $436/mo
- Total monthly fees
- $572/mo
- Total annual fees
- $6,867
- HOA name
- Castle Management - Medley HOA
- CDD
- Yes
- Homestead exemption
- Yes
- Min lease term
- 8-12 Months
- Listing terms
- Cash, Conventional, FHA, VA Loan
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- Buyer to Verify Lease Restrictions with HOA
- Approval process
- Owner to provide copy of the executed lease to the HOA Management with a deposit equal to one months rent.
Exterior & Construction
- Exterior features
- Hurricane Shutters, Lighting, Sidewalk, Sliding Doors, Sprinkler Metered
- Construction materials
- Block, Concrete, Stucco
- Roof
- Tile
- Foundation
- Slab
- Road surface
- Asphalt, Paved
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- Cable Available, Electricity Connected, Natural Gas Connected, Public, Sewer Connected, Underground Utilities, Water Connected
Community
- Pets allowed
- Cats OK, Dogs OK, Number Limit
- Senior community
- Yes
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Primary Bedroom | First | |
| Primary Bathroom | First | |
| Bedroom 2 | First | |
| Bedroom 3 | First | |
| Bedroom 4 | First | |
| Bathroom 2 | First | |
| Bathroom 3 | First | |
| Kitchen | First | |
| Dining Room | First | |
| Laundry | First | |
| Living Room | First |
Listing Details
- Listing date
- 2026-05-18
- On market date
- 2026-05-18
- Original list price
- $636,000
- Occupant type
- Owner
- MLS area
- 33598 - Wimauma
- Listing AOR
- Suncoast Tampa
- Status changed
- 2026-05-19
- Tax legal description
- FOREST BROOKE ACTIVE ADULT PH 4 5B 6B 8B AND COLLECTOR RD 2ND EXT PH 2 LOT 4 BLOCK 36
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
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
More homes like this
$380,000
17414 Holly Well Ave
Wimauma, FL 33598
2 bd · 2 ba · 1,683 sqft
Medley At Southshore Bay
MLS# A4683158
$410,000
17418 Holly Well Ave
Wimauma, FL 33598
2 bd · 2 ba · 1,956 sqft
Medley At Southshore Bay
MLS# TB8464345
$587,500
16805 Banner Shell Pl
Wimauma, FL 33598
3 bd · 3 ba · 2,651 sqft
Medley At Southshore Bay
MLS# TB8482544
Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of May 19, 2026 at 6:52 AM ET. 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.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA