Snowbird Guide to Tampa Bay 55+ Living: Wimauma and Southshore Bay

For Northeastern and Midwestern buyers considering winters in Florida, the Tampa Bay area offers an alternative to South Florida with access to Gulf Coast destinations, active-adult communities and newer one-story homes.

This guide is for people researching a seasonal home, future retirement move or full-time relocation to the Tampa Bay region. It focuses on Wimauma and the Southshore area, including the 55+ community of Medley at Southshore Bay.

Why Northern Buyers Research Tampa Bay for a Florida Home

Florida continues to draw interstate movers from major northern states. Recent Census-based migration data show New York as Florida's largest source of interstate newcomers, with Pennsylvania, Illinois, New Jersey and Massachusetts also among the leading origin states. Tampa remains a relocation destination for online home searchers, with New York identified as its leading out-of-state origin in 2026 relocation search data.

For seasonal residents and future retirees, the decision is usually about more than escaping winter. Buyers often compare maintenance responsibilities, one-story floor plans, community amenities, airport access, insurance, HOA and CDD costs, recreation and whether a community works for both seasonal and eventual full-time living.

Medley at Southshore Bay in Wimauma

Medley at Southshore Bay is a gated 55+ active-adult neighborhood in Wimauma, Florida, in southern Hillsborough County. The community offers an active-adult setting with clubhouse and social spaces, resort-style recreation, pickleball and bocce opportunities, and access to the broader Southshore Bay lifestyle.

Buyers who prefer a newer Florida home without a large property to maintain can compare villa-style and single-level residences in the community.

A Real Example: 17523 Holly Well Avenue

One example of the type of home found in Medley is 17523 Holly Well Avenue, a never-occupied 2024 one-story pond-view villa. The property is currently off market and is presented on this website only as a property and community resource. Its floor plan and setting provide a useful example for buyers researching newer, single-level villa living in Wimauma.

Questions Snowbirds and Relocating Buyers Should Ask

• Will this be a seasonal residence, eventual retirement home or full-time move?
• Do you want a one-story home or villa with lower exterior maintenance?
• What do the HOA and CDD fees cover?
• What are the current lagoon and amenity access provisions?
• What are the community's current age-qualification, guest, pet and leasing rules?
• How will you insure the property while living there seasonally?
• How important are pickleball, fitness, social activities and golf-cart access?
• How close do you want to be to Tampa, airports, medical services and Gulf Coast destinations?

Planning a Florida Move from the North?

If you live in New York, New Jersey, Pennsylvania, Massachusetts, Connecticut, Illinois, Ohio, Michigan or another cold-weather state and are beginning to research a Florida winter home or retirement move, you do not need to start with a specific property. Start with the lifestyle, location, carrying costs and type of community you want.

Kelly M. DeCarlucci, LLC, REALTOR with Dalton Wade Realty Group can help you compare Medley at Southshore Bay and other Tampa Bay-area options, understand the questions to ask about Florida ownership, and narrow the search before you travel.

Kelly M. DeCarlucci, LLC - REALTOR
Dalton Wade Realty Group
813-495-1616
Contact Kelly

Researching Medley specifically? Explore the Medley at Southshore Bay and 17523 Holly Well Avenue community guide.

Community information, fees, assessments, amenities and rules can change. Buyers should independently verify current information and governing documents for any property or community they consider.