Selling and Buying a Home at the Same Time on the South Shore of Massachusetts: Your 4 Smartest Options
You may be wondering: How do I sell my current home and buy my next one without losing my mind (or losing the house I love)?
Buying and selling simultaneously is one of the most common and most stressful real estate situations I help South Shore clients navigate.
The truth? There isn’t one “right” way to do it.
Your ideal strategy depends on:
Current South Shore market conditions
Your risk tolerance
Your finances
Inventory levels in the towns you are interested in
And how flexible your timing can be
Below are the four most common strategies I use with South Shore homeowners, along with their pros and cons.
Option 1: List Your Home With a Suitable Housing Contingency
You list your home with language in MLS stating the sale is contingent upon you finding suitable housing. Once you accept an offer, we actively search for your next property.
Tip: When accepting an offer, negotiate a longer-than-usual closing timeline, ideally 60 days or more. This gives you time to secure your next home.
Pros:
You know exactly what your home sold for
Stronger negotiating position when making an offer
Cons:
Pressure to find a home quickly
The perfect home may not come on the market in time
Important: Sellers typically want you past inspection with a signed Purchase & Sale before accepting your offer. Once you're through inspection, the deal becomes much more secure.
I’ve had clients in towns like Lakeville sell and then aggressively pursue homes in The Pinehills in Plymouth because they didn’t want to move twice. In competitive South Shore neighborhoods, sometimes timing requires decisive action.
Option 2: Buy First, Then List Your Home
In this scenario, we find the right home and submit an offer before putting your current house on the market.
This can work, but usually not on brand-new listings in highly competitive South Shore towns. It’s more successful when a property has been sitting for a few weeks.
Pros:
✔ Less pressure while searching
✔ Avoids a double move
Cons:
Weaker negotiating position
You don’t know what your house will sell for.
If you pursue this route, your home should be fully prepped, photographed, and ready to hit MLS immediately once your offer is accepted.
Option 3: Sell First and Move into Temporary Housing (Strongest Negotiating Position)
This option gives you the most leverage.
You sell your home, close, and move into temporary housing while searching for your next home.
Pros:
✔ No home-sale contingency
✔ Strongest offer position in competitive South Shore markets
✔ Cleaner, simpler transactions
Cons:
Double move
Temporary housing requires flexibility
Tip: Rent-Back Agreement
Negotiate a rent-back agreement. You close on your home (often 45–60 days), then rent it back from the buyer. Lenders typically allow this for up to two months. Cash buyers may allow longer. Your rent usually matches the buyer’s new mortgage payment. This can give you 2–3 extra months to find the right home without scrambling.
Option 4: Use a Bridge Loan
A bridge loan allows you to purchase your next home before selling your current one.
It provides funds for:
Down payment
Closing costs
Transition expenses
Once your current home sells, you pay off the bridge loan.
Pros:
✔ Buy without contingencies
✔ Avoid double move
✔ Less emotional pressure
Cons:
Possible short-term double mortgage payments
Qualification depends on credit, equity, income, and lender guidelines
Many South Shore homeowners don’t realize this is even an option. It requires a detailed conversation with a lender to understand the financial risks.
Which Strategy Works Best in the South Shore Market?
There is no one-size-fits-all solution.
The right approach depends on:
Inventory levels
Your home equity
Market competitiveness
Your comfort level with risk
How urgently do you need to move
If you’re considering moving within the South Shore of Massachusetts, this is just an overview.
The real answer requires a tailored strategy conversation. Every client’s timeline, finances, and goals are different. Reach out anytime for a confidential strategy conversation, no pressure, just clarity.