Village of Hillsborough

Why Hillsborough has its own page

Because the numbers support it. 15 homes closed in Hillsborough in 2026 so far, enough to publish a median without guessing, and every listing is placed here by street against the District's own directory rather than by the MLS subdivision field. Villages with fewer than ten closings are covered on the CR 466A to SR 44 guide instead.

A village gets its own page here only when it has ten or more closed sales in the period, or something written about it that no other page says. Every other village is covered on its section guide, at its own anchor, so the numbers earn the page rather than the name.

What do homes sell for in Hillsborough?

In 2026 so far, 15 homes closed in Hillsborough at a median $390,000, a median $241 per square foot, and a median 78 days on market, on a median 1,559 square feet. Listings are placed in Hillsborough by street against the District's own directory, so these figures cover the whole village.

What kind of homes these are

Source: Stellar MLS, January 1 to September 21, 2026, compiled by Cristian Gonzalez, eXp Realty. Each listing is assigned to Hillsborough by matching its street to The Villages Community Development Districts street directory (September 2026), not by the MLS subdivision field, which names the village on only about one listing in eleven. Information deemed reliable but not guaranteed. Updated September 2026.

What kind of housing is in Hillsborough?

Of the 23 2026 listings on Hillsborough's streets, 78 percent single family homes and 22 percent villas. Homes were built between 2013 and 2014, median 2013, and the closed sales ran a median 1,559 square feet. The District lists 2 villa sections here: New Haven Villas, Ventura Villas.

What to check before you buy in Hillsborough

1. Roof and insurance. Homes here were built 2013 to 2014. This is the newest band where roofs are old enough to matter at all. A 2012 home is reaching the age where insurers start asking questions; a 2017 home generally is not. The five-year spread inside this section is larger than it sounds.
2. Bond. Set per parcel and issued when each unit was platted, so two homes in Hillsborough can carry very different balances. Ask for the exact balance before comparing prices.
3. Price range. Closed sales in 2026 so far ran from $257,500 to $879,000. The median describes the middle of that range, not any one street or floor plan.
4. Negotiating room. Closed sales came in at a median 98 percent of list price after a median 78 days on market.

Bonds issued in the 2010s still have most of their term left, so annual assessments here are meaningfully higher than north of CR 466. This is the band where failing to check the bond distorts a comparison most often, because the homes look modern enough to feel comparable to Southern Oaks while the bond sits between the two. The bond explainer covers how to pull an exact balance, or send me an address and I will run it.

Which district is Hillsborough in?

Hillsborough belongs to District 10 of The Villages Community Development Districts. Your district determines your bond amortization schedule, your utility provider and your sanitation schedule. Villages sometimes span more than one district, so confirm it by address rather than by village name.

Source: district assignment from The Villages Community Development Districts, retrieved September 2026. Section grouping and square proximity are editorial descriptions used for navigation on this site and are not official District designations. Updated September 2026.