Before You Sell Your Home: The 3 Prongs of a Truly Successful Massachusetts Home Sale

If you’re preparing to sell your home in Massachusetts, you’ve likely started by interviewing real estate agents—and rightly so. Choosing the right agent is often the most consequential decision a seller will make.

That said, recent changes in Massachusetts real estate and tax law mean that a truly successful home sale now depends on three critical prongs, not just one:

1. Marketing

2. Financial planning and taxes

3. Legal readiness

Focusing on all three before you list can help protect your proceeds, avoid delays, and reduce stress once you’re under agreement.

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Prong #1: Marketing – Why Hiring the Right Real Estate Agent Still Matters Most

An experienced real estate agent remains the foundation of a strong home sale. Proper pricing, professional marketing, and skilled negotiation can significantly affect the final sale price and the smoothness of the transaction.

A good agent doesn’t simply list your property—they position it strategically to attract qualified buyers and create leverage. This part of the process hasn’t changed.

What has changed is how important it is for sellers to prepare financially and legally before the first showing.

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Prong #2: Financial Planning and Taxes – What Sellers Should Understand Before Listing

Many sellers assume tax issues can wait until after closing. In today’s regulatory environment, that assumption can lead to unexpected complications.

* Will You Owe Capital Gains Tax When You Sell?

Depending on how long you’ve owned the property, how it was used, and whether you qualify for the primary residence exclusion, capital gains tax may apply to some or all of your sale proceeds.

This issue is especially relevant for investment properties, second homes, and long-held residences in rapidly appreciating markets.

For a plain-English overview of how capital gains tax works in real-world home sales, see our article Capital Gains Tax for Dummies.

* New Massachusetts Tax Withholding Rules for $1M+ Home Sales

Massachusetts has recently implemented new tax withholding requirements that may apply to certain real estate sales over $1 million—even when no tax is ultimately owed.

These rules can affect the amount withheld at closing, the timing of your proceeds, and whether a post-closing refund is required.

We discuss these rules in more detail in New Tax Withholding Law for Massachusetts Sales.

* Estimating Your Net Sale Proceeds Before You List

Knowing your likely “walk-away” number is critical for financial planning—whether you’re buying another home, downsizing, or reallocating assets.

Many sellers are surprised to learn they can estimate net proceeds within a few hundred dollars before listing using our Walk-Away Cash Calculators.

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Prong #3: Legal Readiness – Identifying Issues Before They Delay the Sale

Legal issues rarely derail a transaction entirely, but they often cause delays, added expense, or last-minute renegotiations.

A pre-sale legal review by a Massachusetts real estate attorney can identify common issues such as:

• Undischarged or improperly discharged prior mortgages

• Open Orders of Conditions or municipal restrictions

• Title issues involving deceased owners or unprobated estates

• Easements, shared driveways, or access rights

• Old liens that should have been cleared years ago

Addressing these matters before listing helps ensure a smoother transaction and a more predictable closing timeline.

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The Bottom Line: A Successful Home Sale Takes More Than Marketing

Selling your home is not just a transaction—it’s a significant financial and legal event.

Yes, hire a great real estate agent. But also consider speaking with your tax advisor, real estate attorney, and—where appropriate—your financial planner.

A modest amount of planning on the front end can help protect your proceeds and make

closing day far less stressful.

If you’re considering selling and would like guidance on the legal or tax issues involved, our office is always happy to talk.

📞 Have questions? Reach out anytime: www.vanderveen-law.com

***This article is intended for general informational purposes and should not be construed as legal, tax or other professional advice. Prior to acting on any information in this article, you should seek legal, tax or other relevant professional counsel.***