Cypress Mill vs Southshore Bay
Two Hillsborough communities, compared on the numbers that decide it — price, pace, and supply — from live MLS data as of 2026-09-19.
| Metric | Cypress Mill | Southshore Bay |
|---|---|---|
| Median sale price | $338K | $320K |
| Price per sq ft | $174 | $169 |
| Avg days on market | 69 days | 103 days |
| Months of supply | 5.5 mo | 9.6 mo |
| Market | Buyer-Leaning Market | Buyer-Leaning Market (limited data) |
| 1-year price change | False | False |
| Recent closings | 24 | 5 |
The verdict
Cypress Mill carries the higher median price — about 6% above Southshore Bay. Homes in Cypress Mill sell faster (69 days on market vs 103). Cypress Mill is the tighter market on inventory (5.5 months of supply).
Where each one is
| Cypress Mill | Southshore Bay | |
|---|---|---|
| County | Hillsborough County, FL | Hillsborough County, FL |
| City / area | Sun City Center | Wimauma |
| ZIP | 33573 | 33570, 33598 |
| FEMA flood zones (sampled parcels) | all 25 sampled homes outside a flood zone | 90% of 10 homes outside a flood zone (Zone X) |
Distances are straight-line; driving distance is usually 15 to 30 percent more. Flood-zone shares come from FEMA flood maps matched to sampled parcels; always check the exact address before you close.
What is for sale today
| Cypress Mill | Southshore Bay | |
|---|---|---|
| Homes for sale now | 11 | 4 |
| Under contract | 4 | 1 |
| Asking prices today | $280K to $420K | $260K to $330K |
| Property types listed | Single Family Residence | Single Family Residence, Townhouse |
Live MLS counts, refreshed with every listing pull. Browse them: Cypress Mill homes for sale · Southshore Bay homes for sale.
The homes themselves
| Cypress Mill | Southshore Bay | |
|---|---|---|
| Homes (parcels) | 529 | 94 |
| Built | 2018–2023 (median 2021) | 2018–2023 (median 2020) |
| Typical living area | 2,151 sq ft | 2,521 sq ft |
| Homesteaded (owner-occupied) share | 70% | 72% |
Housing-stock figures from the Florida Department of Revenue 2025 assessment roll (public records).
Price history, year by year
| Year | Cypress Mill median | Southshore Bay median |
|---|---|---|
| 2021 | $282K (20 sales) | $287K (17 sales) |
| 2022 | $364K (110 sales) | $370K (75 sales) |
| 2023 | $370K (66 sales) | $388K (67 sales) |
| 2024 | $351K (26 sales) | $305K (66 sales) |
| 2025 | $350K (19 sales) | $293K (48 sales) |
| 2026 | $330K (17 sales) | $255K (5 sales) |
Since 2021, Cypress Mill's median sale price is +17% and Southshore Bay's is -11% — Cypress Mill has appreciated faster over that stretch.
How each one trades
| Cypress Mill | Southshore Bay | |
|---|---|---|
| Sale-to-original-list | 94.9% | 100.0% |
| New-construction share of sales | 0% | 100% |
| Typical sold home | 1,914 sq ft | 1,787 sq ft |
Last 12 months of recorded closings; sale-to-original-list is the share of the first asking price sellers actually got.
Schools the listings are zoned for
| Cypress Mill | Southshore Bay | |
|---|---|---|
| Elementary | Cypress Creek-Hb | Reddick Elementary School |
| Middle | Shields-Hb | Shields-Hb |
| High school | Sumner High School | Sumner High School |
The school most often recorded on each community's MLS listings. Always confirm a specific address with the district.
Which one fits
On budget alone, Southshore Bay is the lower entry point (median $320K vs $338K). Buyers who want newer construction (fewer near-term roof, HVAC and re-plumb items, and easier insurance quotes in Florida) will find it in Cypress Mill; Southshore Bay trades that for a more established street and, typically, larger lots. Sellers get a faster sale in Cypress Mill (69 days on market on average); buyers get more negotiating room where homes sit longer.
Neither number set decides it: drive both on a weekday evening, check the HOA documents and the flood zone for the exact street, and price the insurance before you write an offer. A Momentum agent who works both communities can pull the comparable sales for any two specific homes.
Questions people ask
Is Cypress Mill more expensive than Southshore Bay?
Yes, on recent sales: the median sale price in Cypress Mill is $338,000 versus $320,000 in Southshore Bay, about 6% higher.
Which has newer homes, Cypress Mill or Southshore Bay?
Cypress Mill: its homes were built 2018–2023 with a median year of 2021, versus a median of 2020 in Southshore Bay (Florida DOR assessment roll).
Which has bigger homes?
Southshore Bay. The typical home there is 2,521 sq ft of living area, versus 2,151 sq ft in Cypress Mill.
Which has appreciated more, Cypress Mill or Southshore Bay?
From 2021 to 2026 the median sale price rose 17% in Cypress Mill and -11% in Southshore Bay (recorded MLS closings by calendar year).
Where do sellers get closer to asking price?
Southshore Bay — sellers there received 100.0% of the original list price over the last 12 months versus 94.9% in Cypress Mill.
What high schools serve Cypress Mill and Southshore Bay?
Listings in Cypress Mill most often report Sumner High School; listings in Southshore Bay report Sumner High School. Zoning is set by the district and can change - verify by address.
Go deeper on each: Cypress Mill homes, photos & schools · Southshore Bay homes, photos & schools
Figures are aggregates from realMLS / DBAAR, updated regularly. Thinking about either? Talk to Momentum Realty.