Location: Medley At Southshore Bay, Wimauma
Do Not Show Listings
17414 HOLLY WELL AVE, WIMAUMA, FL 33598
$370,000103 Days on yellowkey MLS ID: A4683158
REDUCED by $20,000 (5.1%) on 05/31/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1683 Built: 2024Monthly Fee: $560 Tax: $5,396 (2025)Community: Medley At Southshore BaySingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,396
Elementary School: Reddick Elementary School
High School: Sumner High School
Tax Year: 2025
Middle School: Shields-HB
Remarks: Welcome to this move-in ready single-family home located in the highly sought-after Medley at Southshore Bay, a gated, maintenance-free community where only one resident is required to be 55 or better. Designed for comfortable, low-maintenance living, this home offers 2 bedrooms, 2 bathrooms, and a versatile flex room with a custom door, ideal for a home office, den, or guest space. The open-concept layout features white cabinetry, quartz countertops, and stainless steel appliances, including a gas cooktop and oven, allowing the kitchen to flow seamlessly into the main living and dining areas. Additional features include a tankless gas water heater and a full-house water filtration system, providing added efficiency and peace of mind. Step outside to the screened-in lanai overlooking a fully fenced backyard with open views and no rear neighbors, offering a peaceful sense of privacy rarely found within the community. This inviting outdoor space is perfect for enjoying quiet mornings or relaxing evenings. Additional highlights include ample storage and a 2-car garage. Lawn care is included, allowing residents to fully enjoy Medley’s resort-style amenities, including a lagoon-style pool, on-site restaurant and bar, pickleball courts, fitness center, golf cart-friendly streets, and a full calendar of social activities. This home offers an excellent opportunity to enjoy privacy, simplicity, and an active lifestyle in one of Wimauma’s most desirable communities. Schedule your private showing today.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Kristyn Haster (303-257-8945)
5305 WINDY GROVE DR, WIMAUMA, FL 33598
$636,00015 Days on yellowkey MLS ID: TB8508434
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2856 Built: 2022Monthly Fee: $436 Tax: $8,463 (2025)Community: Medley At Southshore BaySingle Family
Taxes:$8,463
Elementary School: None
High School: None
Middle School: None
Remarks: 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
Listing is courtesy of: RE/MAX REALTY UNLIMITED (813-684-0016)
Listing Agent: Lori Rivero (941-465-6794)
17418 HOLLY WELL AVE, WIMAUMA, FL 33598
$410,000139 Days on yellowkey MLS ID: TB8464345
INCREASED by $11,000 (2.8%) on 04/25/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1956 Built: 2024Monthly Fee: $482 Tax: $7,819 (2025)Community: Medley At Southshore BaySingle Family
Taxes:$7,819
Remarks: Welcome to elevated Florida living in the highly sought-after 55+ community of Medley at Southshore Bay — where resort-style amenities, low-maintenance living, and designer upgrades come together beautifully at 17418 Hollywell Ave. This beautifully upgraded home offers the perfect blend of comfort, style, and lifestyle. From the moment you walk in, you’ll notice the calming designer paint palette, upgraded lighting, and thoughtful finishes that make this home feel like a private retreat. The kitchen is a standout feature with premium KitchenAid appliances, gorgeous cabinetry, and an open-concept layout perfect for entertaining or quiet nights at home. The flex room has been beautifully enclosed with custom barn doors, creating the ideal office, guest space, hobby room, or cozy den. The primary suite features a custom-designed closet that adds both luxury and functionality, while the fenced backyard provides privacy and space to relax outdoors. But what truly sets this home apart is the lifestyle that comes with it. Your HOA includes high-speed internet, cable, and premium streaming services including Disney+, Hulu, Paramount+, and more — making everyday living both convenient and cost-effective. Residents also enjoy access to the incredible crystal lagoon with guest passes for visiting family and friends, a resort-style clubhouse, fitness center, pickleball courts, social events, and a gated golf-cart-friendly community designed for active living and connection. Lawn maintenance is included, giving you more time to enjoy the Florida lifestyle instead of maintaining it. Why wait to build when this home already offers the upgrades, privacy, and move-in-ready features buyers are searching for — all in one of the area’s most vibrant resort-style communities? Sellers are Offering to Pay the Capital Contribution Fee for the Buyers at Closing!!! A $2200 SAVINGS!
16805 BANNER SHELL PL, WIMAUMA, FL 33598
$587,50091 Days on yellowkey MLS ID: TB8482544
REDUCED by $7,500 (1.3%) on 05/03/2026
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2651 Built: 2020Monthly Fee: $436 Tax: $7,148 (2024)Community: Medley Southshor BaySpa: YesSingle Family
Taxes:$7,148
Tax Year: 2024
Remarks: Welcome to your Florida LUXURY Dream Pool Home! This custom-built residence showcases a SPECTACULAR Heated and Chilled Private Pool featuring a Raised Spa, Oversized Bubbling Sun Shelf Island, sheer descent waterfall, color-changing lighting, and an expansive 37-foot pool design creating your own tropical oasis. The extended paver patio is fully fenced for privacy and ideal for entertaining. Inside, you’ll find a bright and spacious open-concept floor plan with soaring ceilings and a stunning 12-foot custom sliding glass door that seamlessly blends indoor and outdoor living. The gourmet kitchen is beautifully appointed with UPGRADED White Quartz Countertops with crystal accents (installed last year), UPGRADED stainless steel appliances including refrigerator, dishwasher, washer and dryer, extensive recessed lighting, and a flexible bonus room perfect for a home office, gym, or additional living space. LUXURY PLANK VINYL Flooring newly installed in the guest bedrooms! The primary suite offers a peaceful retreat with abundant natural light and a generous walk-in CUSTOM closet. The spa-inspired primary bath features dual sinks, a LUXURIOUS soaking tub, walk-in shower, custom cabinetry, and elegant finishes. Additional highlights include: • Custom crown molding in main living areas • Three-car garage plus upstairs storage room • Custom built-in cabinetry and additional storage • Modern neutral finishes throughout • Option to purchase PARTIALLY furnished Located in the gated community of Medley at Southshore Bay, residents enjoy resort-style amenities including a clubhouse with ballroom, fitness center, card rooms, pickleball courts, tennis, bocce ball, shows and entertainment, tropical beach entry pool, indoor and outdoor dining, and full bar service. Membership also includes access to the 5-acre Southshore Bay Crystal Lagoon and Splash Pad. Golf cart friendly community with year-round activities and lifestyle events.
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