Tired Landlord? How to Sell a Rental Property with Tenants in Boston
Navigating Massachusetts tenant laws to sell your investment property
Being a landlord in Boston isn't what it used to be.
Between the strict eviction laws in Massachusetts, the high cost of maintenance in neighborhoods like Dorchester and Allston, and the late-night calls about broken boilers, many investors eventually hit a wall. You are "house rich but cash poor," and you just want out.
Important: Selling a rental property isn't like selling a vacant home. If you have tenants living in the unit, you face a unique set of hurdles.
Common Landlord Concerns:
- What if they refuse to leave during showings?
- What if they stop paying rent once they know you are selling?
- Can you even legally ask them to leave?
Here is the "Tired Landlord's Guide" to liquidating your Boston investment property without the legal headaches.
1. The "Lease" vs. "Tenancy-at-Will" (The Critical Difference)
Before you list the property, you need to know exactly what kind of legal agreement you have. In Massachusetts, this changes everything.
Scenario A: Fixed-Term Lease
If your tenant has a lease that expires on August 31st, you generally cannot kick them out before that date.
- Even if you sell the house, the lease "runs with the land." The new buyer must honor the lease and become the new landlord.
- The Problem: Most traditional buyers looking for a family home won't touch a property with a tenant locked in for another 6 months.
Scenario B: Tenancy-at-Will (Month-to-Month)
If there is no written lease, or the lease has expired, you have a "Tenancy-at-Will."
- The Rule: You must give the tenant a full rental period's notice to vacate (usually 30 days, ending on a rent day).
- The Risk: Just because you give them a "Notice to Quit" doesn't mean they will leave. If they stay past the date, you cannot just change the locks. You have to start a formal eviction.
2. The Nightmare of "Showings" with Unhappy Tenants
Imagine trying to sell your house while someone else is living in it—someone who doesn't want you to sell.
We see this all the time in Boston:
- Tenants leaving the house messy on purpose during open houses
- Tenants bad-mouthing the property to potential buyers
- Tenants refusing access, claiming they didn't get "reasonable notice"
If your tenant decides to sabotage the sale, your property could sit on the MLS for months.
3. The "Cash for Keys" Strategy
If you need the tenants out but don't want to go to housing court (which can take 6+ months in Boston), many landlords use a strategy called "Cash for Keys."
This is essentially a buyout agreement.
- You offer the tenant a sum of money (e.g., $2,000–$5,000) to move out voluntarily by a specific date
- You only pay them after they have handed over the keys and you have inspected the empty unit
Warning: This requires a strictly worded legal agreement to ensure they don't take the cash and stay.
4. The Eviction Reality in Massachusetts
If the tenant stops paying rent or refuses to leave, you have to evict. In Massachusetts, this is slow and expensive.
14-Day or 30-Day Notice to Quit
The first formal step
Summary Process Summons
You have to serve them court papers
The Court Date
Mediation is often required before you see a judge
The Stay of Execution
Even if you win, a judge can give the tenant months to find a new place
Total Time: 4 to 9 months
Total Cost: $5,000+ in attorney fees and lost rent
The Solution: Sell the Property With the Tenants
This is where a cash buyer like All Vest Group solves the problem.
We buy occupied rental properties in Boston every month. We don't care if the tenants are messy, if they are paying below market rent, or even if they have stopped paying altogether.
✓ No Eviction Needed
We inherit the tenants. You transfer the lease to us at closing, and you are done.
✓ No Awkward Showings
We don't need to parade strangers through their living room. We do one quick inspection.
✓ We Buy "Bad" Leases
Stuck with a tenant paying below market rent? We have the resources to handle that.
How it Works
We make you an offer based on the property's potential. Learn more about our process.
We close. You hand over the keys and the leases. See how we buy houses fast.
You never have to answer a tenant phone call again.
Ready to retire from being a landlord?
Don't let a bad tenant situation hold your equity hostage.
Get a Cash Offer for Your Rental PropertyServing Boston and surrounding areas including Boston, MA and Essex, MA.
