Wimauma › Medley at Southshore Bay

17255 Holly Well Ave

Wimauma, FL 33598
$298,900
2 bed2 bath1,614 sqftVilla · built 2024

What stands out about this home

Compared with villas like it, within product classi
Size
Larger than 39% of villas sold in Wimauma
61 villa sales · Jan 2024 - Oct 2026
Price
The seller has not permitted automated price comparisons
Standout feature
No standout feature to report
Age
Newer than 73% of villas in Wimauma
113 homes · Aug 2022 - Oct 2026
Compared against 40 similar homes sold within 1.8 mi.

About this property

COME FOR THE HOME, STAY FOR THE NEIGHBORS, FRIENDSHIPS, AND LIFESTYLE. There’s something special about life on this street in Medley, where neighbors quickly become friends and a welcoming sense of community makes it easy to feel right at home. Whether you’re enjoying neighborhood get-togethers, taking advantage of the many activities and amenities, or simply relaxing with friends, this is more than a place to live—it’s a lifestyle to enjoy. Welcome to 17255 Holly Well Ave, a gorgeous 2024-built villa offering 1,614 sq. ft. of beautifully designed living space in Medley at Southshore Bay, a vibrant 55+ community located on the outskirts of Sun City Center. Situated on a desirable corner lot in a no-flood zone, this home combines modern finishes, energy efficiency, low-maintenance living, and an impressive resort lifestyle.

Step inside through the charming side-entry front door to an inviting open-concept living and dining area accented by crown molding throughout the entire home. The oversized kitchen is designed for both entertaining and everyday living, featuring quartz countertops, upgraded cabinetry, a gas range, generous workspace, and a large walk-in pantry. Smart-home technology, ultra-efficient features, natural gas, and a tankless water heater add convenience and efficiency.

The thoughtfully designed split-bedroom floor plan provides privacy, with two spacious bedrooms plus a versatile flex room that’s perfect for a home office, den, craft room, or hobby space. The primary suite offers an impressive 11-foot walk-in closet, while the ensuite bath features dual sinks and plenty of room to get ready.

One of the home’s best features is the outdoor living space. Step onto the screened lanai overlooking a large pond and enjoy peaceful water views—the perfect setting for morning coffee, evening cocktails, or simply relaxing and enjoying the Florida lifestyle.

Additional features include a tile roof, paver driveway, one-car garage with upgraded overhead storage, and low-maintenance villa living. The HOA makes ownership even easier by covering roof and exterior maintenance, landscaping, irrigation water, high-speed internet, and cable.

Living in Medley at Southshore Bay is about much more than the home. Residents enjoy a beautiful clubhouse, resort-style pool, pickleball courts, dog park, and access to the incredible Southshore Bay Lagoon, where you can enjoy water activities, entertainment, and live concerts—all without leaving your community.

If you’re looking for a nearly new Florida home where you can spend less time maintaining and more time enjoying life, 17255 Holly Well Ave delivers the perfect combination of comfort, style, water views, and resort-style 55+ living.

Property details

Year built2024
Lot size0.14 ac
HOA + Association 2 + Other monthly fees$432/mo HOA + $236.30/qtr second association + $108/mo other
Parking1-car
Days on market32
MLS#TB8542705
Hurricane shuttersLightingSidewalkCeiling fansCrown moldingEat-in kitchen
All features →
  • Hurricane shutters
  • Lighting
  • Sidewalk
  • Ceiling fans
  • Crown molding
  • Eat-in kitchen
  • High ceilings
  • Living/dining combo
  • Open floorplan
  • Primary bedroom main floor
  • Split bedroom
  • Stone counters
  • Thermostat
  • Walk-in closets
  • Window treatments
  • Convection oven
  • Dishwasher
  • Disposal
  • Dryer
  • Exhaust fan
  • Microwave
  • Range hood
  • Refrigerator
  • Tankless water heater
  • Washer
  • Carpet flooring
  • Tile flooring
  • Central air conditioning
  • Central heating
  • Tile roof
  • Slab foundation
  • Brick construction
  • Stucco construction
  • Single story
  • Laundry room
  • Cable connected
  • Electricity connected
  • Fire hydrant
  • Natural gas connected
  • Public utilities
  • Water connected
  • Gated community
  • Key card entry
  • Smoke detectors
  • Garage
  • Quartz countertops

The market for homes like this

Wimauma, as its listings describe it

What agents stated on listings, 2019 – 2026i
Community pool86%of 435 listings
HOA fee, median$75/moof 436 listings
Has an association97%of 536 listings
Pets allowed92%of 666 listings
Minimum lease, most common1-2 Years31% of 373 listings · next: 8–12 Months
Lease restrictions75%of 374 listings
Association approval required48%of 370 listings
Private pool7%of 690 listings
Gated34%of 435 listings
Public water · sewer94% · 95%of 465 · 494 listings
Flood zone (A or V)2%of 494 listings
55+ communityNo83% of 545 listings · next: Yes
Homestead share69%of 5,706 homes · county tax roll
Also stated: waterfront 8% of 545 listings; CDD 90% of 453.

Price and time on market

This listing against homes like iti
Price per sq ft
The seller has not permitted automated price comparisons
Time on market
The seller has not permitted automated comparisons
Price history
Listed at $299,900 originally; now $298,900, 0.3% lower after at least one price reduction. The most recent: down $1,000 on Sept. 28, 2026
at least one price reduction visible

Cost of ownership

What this home costs to hold, from public recordsi
Current owner's taxes
i
$5,242 for 2025 on the listing; about $3,559 on the 2026 roll
The listing and the county roll disagree materially; both are shown
Estimated taxes at this price
i
About $3,500/yr homesteaded, $4,200/yr as an investor
Estimated: the asking price through the county's price-to-value factor, at the parcel's published millage; assessments reset at sale
Typical electric bill
i
$166/mo (2024)
Typical: the utility's average residential bill for 2024 (not this home's)
Typical water and sewer
i
$98/mo at 5,000 gallons
Typical: the provider's published schedule at 5,000 gallons a month on a standard residential meter
THE NEIGHBORHOOD

Living in Wimauma

unincorporated Hillsborough County · Hillsborough County · ZIP 33598 · Wimauma (census-designated place) · Flood zone X
Explore Wimauma →
Homes5,706residential parcels
Median sold price$351,540291 sales · last 12 months
Vs. the prior year+0.4%291 sales this year · 391 sales the prior year
Median rent$2,525/mo90 leases · last 12 months
Homes that changed hands5%291 sales of 5,706 homes
Homestead share69%of 5,706 homes · county tax roll
Villas in Wimauma, by bedroomsFigures appear once a group has 40 sales
GROUPSALESMEDIAN SOLDMEDIAN RENT
All villas · 12 months8Not enough sales yet to report on their own
2 bed · this home8Not enough sales yet to report on their own
All villas · 24 months18Not enough sales yet to report on their own
Median price

Wimauma homes sold for a median of $351,540 in the 12 months to Oct. 11, 2026.

291 sales
Price trend

That's 0.4% above the median for the 12 months before, $350,000.

291 sales this year · 391 sales the prior year
What's selling

Single-family detached homes made up 271 of the 291 sales in the same 12 months, at a median of $356,005.

271 of 291 sales

Location

17255 HOLLY WELL AVE, WIMAUMA, FL 33598

Nearby homes for sale in Wimauma

Based on information from Stellar MLS® for the period May 30, 2019 through October 11, 2026.

Listings courtesy of Stellar MLS as distributed by MLS GRID

HomeProp is a licensed Florida real estate brokerage (License CQ1055163). Regulated by the Florida Real Estate Commission (FREC), 400 W Robinson St, Orlando, FL 32801. All information deemed reliable but not guaranteed.

← Browse homes for sale
Request a showing