If you own a tenant occupied property in Massachusetts, you usually fit into one of these situations:

• You are a landlord who wants to cash out

• You inherited a rental and do not want to run it

• You have a “temporary tenant” who became permanent

• You want to sell fast, but the tenant situation feels like a knot

This guide gives you a clean, Massachusetts-friendly path. It covers leases, month to month tenancies, showings, deposits, and the three selling routes that actually work.

This is general info, not legal advice. If you have a high conflict tenant or a court timeline, talk with a Massachusetts attorney who handles landlord tenant and real estate closings.

The big idea: pick the right sale route first

Most “tenant occupied mess” happens when an owner chooses a route that fights reality.

You have three sane routes:

Sell with the tenant in place

Negotiate a voluntary move out

End the tenancy using the legal process

Route one is often the least stressful. Route two can be the fastest way to vacancy. Route three is the slowest and most expensive, but sometimes unavoidable.

Your job is to pick the route that fits the tenancy you have, not the tenancy you wish you had.

Step 1: Identify the tenancy type

In Massachusetts, this is not a small detail. It controls what you can do and how fast you can do it.

Tenant with a written lease

A lease is a fixed term agreement. If the tenant has a valid lease, you should assume it stays in place through its end date.

Massachusetts Legal Help explains that if a building is sold, the new landlord has to honor the agreements in the current lease and accept the old rent amount until the lease ends, or until proper notice applies.

Plain English: you can sell, but you are usually selling a rental, not a vacant home.

Tenant at will (month to month)

This is the common “month to month” setup.

Mass.gov explains that a landlord or tenant can end a month to month tenancy at will by giving a written notice to quit of at least 30 days that expires at the end of a rental period.

That last part matters. “Thirty days” is not always the same as “next month.” Timing can be tricky, especially around February.

Subsidized or special tenancies

If the tenancy is subsidized (like certain state or federal programs), extra rules can apply. Massachusetts Legal Help notes that certain subsidized leases can continue even through foreclosure situations.

If you see Section 8 paperwork or program documents, slow down and get advice before you act.

Step 2: Decide what kind of buyer you want

Tenant occupancy does not kill your sale. It changes who the buyer is.

If you want top dollar from owner occupants

Owner occupant buyers usually want the property vacant, or they need a clear plan for vacancy.

That points you toward:

• waiting out the lease

• negotiating a move out

• or ending a month to month tenancy with proper notice

If you want the cleanest sale with the least disruption

Sell to a buyer who wants a rental.

That points you toward:

• selling with the tenant in place

• marketing to local landlords or small investors

• keeping showings limited and organized

Step 3: Build the “buyer confidence” package

Tenant occupied deals fall apart when buyers feel blind.

If you want a smoother closing, gather these items early:

• lease and any renewals

• rent amount, due date, payment method

• rent ledger (what was paid and when)

• security deposit amount and where it is held

• last month’s rent if collected

• utility responsibility

• list of repairs completed and open issues

• tenant contact info and preferred showing windows

This package does two things:

• It speeds up due diligence.

• It reduces the “risk discount” buyers apply when they feel uncertain.

What changes when the property sells

When you sell a rental, the buyer steps into the landlord role. That means the buyer inherits responsibilities, and your paperwork needs to be clean.

Security deposit rules matter a lot in Massachusetts

Mass.gov explains that if the landlord sells or no longer owns or manages the property, the landlord must transfer the tenant’s security deposit (including interest) to the new owner or manager. The new owner then has 45 days to give the tenant written notice that they received the deposit and where it is held.

Massachusetts Legal Help also stresses the same practical point: after a sale, the new landlord has a deadline to notify the tenant about the deposit and last month’s rent, and the deposit “chain of custody” matters.

If you are selling, do not wing this. Deposit mistakes create legal exposure and can poison a deal.

Showings: what you can do, and what you should not do

Showings are where rental sales often get tense. You want access. Tenants want privacy. Both are reasonable.

Massachusetts has clear limits on entry.

Massachusetts General Laws, Chapter 186, Section 15B says a lease cannot allow entry except to inspect, make repairs, or show the unit to a prospective tenant, purchaser, or mortgagee (and related agents).

The Massachusetts Attorney General’s guide also notes that the landlord must arrange with the tenant in advance to enter for repairs, inspection, or showing to prospective tenants or buyers.

Massachusetts Legal Help explains the same idea in plain language and adds that “extra” entry reasons in a lease can be illegal.

The least messy showing plan

Use structure. Structure reduces conflict.

• Give reasonable notice

• Bundle showings into set windows

• Keep it predictable (same days and times)

• Treat the tenant like a human, not an obstacle

If you try to “surprise” your way into access, the tenant usually fights harder. Then you lose time.

The three routes, explained like you actually have a life

Route 1: Sell with the tenant in place (often the least messy)

This works best when:

• the tenant pays

• the unit is stable

• the lease has time left

• you want fewer moving parts

Pros:

• no vacancy gap

• no rush to clean out or renovate

• investors understand what they are buying

Cons:

• smaller buyer pool

• some buyers discount price due to access limits and risk

What makes it work:

• clean documents

• honest rent ledger

• clear showing plan

• clear deposit transfer plan

Route 2: Negotiate a voluntary move out (fastest path to vacancy)

If you need the property vacant, a voluntary agreement often beats court.

Many landlords call this “cash for keys.” Done right, it is just a written agreement where the tenant leaves by a date and you provide agreed value.

MassLandlords provides an “Agreement to End Tenancy” form and notes it should be executed in coordination with a mediator or attorney, especially if it is your first time.

Pros:

• faster vacancy than court in many cases

• lower conflict when handled respectfully

• you can plan the closing date

Cons:

• it costs money

• it requires cooperation

A clean agreement should cover:

• move out date and time

• condition expectations

• how you handle items left behind

• when and how payment happens

• how keys get returned

Do not promise something you cannot deliver. Trust breaks once. Then you are back to the messy route.

Route 3: End the tenancy using the legal process (slowest, but sometimes needed)

If the tenant stops paying or violates key terms, you may need to end the tenancy through the formal process.

For month to month tenancies at will, Mass.gov explains the 30 day notice to quit rule and timing requirement.

Important: a notice to quit is a starting step. It does not mean the tenant must leave that day, and it is not a physical removal order.

If you are heading toward court, avoid DIY paperwork. Small notice mistakes can cause delays.

How to choose the right route in 60 seconds

If you want a fast decision rule, use this:

• Tenant has a lease and pays: sell with tenant in place

• Tenant is month to month and pays: decide if you want to end tenancy with proper notice or sell occupied

• Tenant does not pay: talk to counsel, consider legal process, and weigh whether an investor purchase still makes sense

• You need vacancy to list retail: negotiate a voluntary move out first

The mistakes that make rental sales ugly

Avoid these and you avoid most problems.

Mistake 1: Treating “sale” like it ends tenant rights

It does not. The tenancy rules keep running. The buyer steps into the landlord role, and leases remain meaningful.

Mistake 2: Entering whenever you want because you “own the house”

Massachusetts limits entry reasons, and the Attorney General’s guide stresses advance arrangement with the tenant.

Mistake 3: Sloppy deposit handling

Ownership change triggers strict deposit transfer and notice rules, including the 45 day written notice requirement for the new owner.

Mistake 4: Trying to bully a tenant into leaving

Pressure tactics usually backfire and can create legal risk. If you need vacancy, negotiate or use the process.

Where this applies across Eastern Massachusetts

Tenant occupied and rental sales come up across Eastern Massachusetts, including Boston, Cambridge, Somerville, Brookline, Newton, Quincy, Chelsea, Revere, Winthrop, Everett, Malden, Medford, Arlington, Belmont, Watertown, Waltham, Lexington, Lincoln, Concord, Bedford, Burlington, Woburn, Winchester, Reading, Wakefield, Melrose, Stoneham, North Reading, Wilmington, Billerica, Tewksbury, Lowell, Chelmsford, Dracut, Framingham, Natick, Needham, Wellesley, Weston, Wayland, Sudbury, Dedham, Westwood, Norwood, Canton, Milton, Braintree, Weymouth, Hingham, Hull, Cohasset, Scituate, Marshfield, Duxbury, Hanover, Norwell, Pembroke, Hanson, Halifax, Plymouth, Kingston, Middleborough, Lakeville, Salem, Beverly, Danvers, Peabody, Lynn, Saugus, Swampscott, Marblehead, Nahant, Gloucester, Rockport, Ipswich, Rowley, Newburyport, Amesbury, Salisbury, Haverhill, Lawrence, Methuen, Andover, North Andover, Middleton, Topsfield, Boxford, Hamilton, Wenham, Manchester by the Sea, and out toward Cape Cod towns like Bourne, Sandwich, Falmouth, Mashpee, Barnstable, Yarmouth, Dennis, Harwich, Brewster, Chatham, Orleans, Eastham, Wellfleet, Truro, and Provincetown.