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Buying a Second Home in Massachusetts

A second home should support your lifestyle first and your long-term financial goals second. I help MetroWest and Greater Boston buyers purchase beach homes and vacation properties with clarity, strategy, and calm guidance.

A Step-by-Step First Time Seller's Guide

Putting your home on the market can be a stressful process, especially when you don’t know what to expect. Fortunately, with the help of an experienced agent and this easy to follow guide, you can smoothly complete the process. Following these steps will help you prepare so you can get organized and sell your home for the best price possible.​​​​​​​

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Buying a Second Home in Massachusetts

More Than a Getaway. A Long-Term Decision.

For many homeowners in Needham, Newton, Wellesley, and across MetroWest Boston, buying a second home isn’t about becoming a real estate investor.

It’s about:

  • Creating a gathering place for family

  • Building memories by the water

  • Planning ahead for retirement

  • Owning something tangible in an uncertain world

  • Possibly offsetting expenses with thoughtful rental income

A second home is emotional.
But it is also a significant financial decision.

The key is approaching it with both heart and strategy.

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Lifestyle First. Strategy Always.

When we look at Cape Cod beach homes or Massachusetts vacation properties, we evaluate more than just how charming the porch looks at sunset.

We look at:

Location & Use

  • Walkability to beaches, town centers, and amenities

  • Flood zones and insurance implications

  • Septic systems and bedroom capacity

  • Year-round usability vs seasonal limitations

  • Long-term neighborhood appeal

Financial Positioning

  • Appreciation history in the area

  • Price per square foot relative to nearby sales

  • Operating costs and maintenance

  • Rental regulations and short-term rental rules

  • Resale flexibility

Even if you plan to use the home primarily for yourself, buying strategically protects your future options.

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Should You Rent It Out?

Many buyers ask:

“Should we rent it part-time to help cover costs?”

The answer depends entirely on your goals.

Some buyers want:

  • Complete privacy and no rentals

  • Rental income during peak summer weeks

  • Flexibility now and retirement potential later

  • A property that performs well if circumstances change

If rental income is part of the conversation, we evaluate:

  • Local short-term rental restrictions

  • Parking requirements

  • Bedroom layout and functionality

  • Beach proximity and demand

  • Management logistics

If you want to explore what makes a strong short-term rental property, I share more here:
👉 What to Look for in a Short-Term Rental Property Investment

But remember — rental potential is a layer of strategy. It should not override lifestyle fit.

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Putting My Money Where My Mouth Is

When I purchased 118 Bay Road in Eastham, I went through the same process I guide my clients through.

Renovation budgeting.
Seasonality analysis.
Rental demand.
Long-term appreciation.

Owning a second home is different from owning your primary residence. There are additional layers:  emotional, financial, and logistical.

That experience allows me to guide buyers with firsthand insight, not just theory.

You can read more about that decision here:
👉 Why I Bought 118 Bay Road – Putting My Money Where My Mouth Is

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Why Real Estate Still Makes Sense Long-Term

Unlike stocks or abstract investments, a second home is:

  • Tangible

  • Usable

  • Inflation-resistant

  • Historically appreciating in desirable markets

  • Multi-functional

It can serve as:

  • A family retreat

  • A retirement option

  • A rental asset

  • A legacy property

When purchased thoughtfully, a beach house in Massachusetts can be both a lifestyle decision and a long-term wealth strategy.

For a deeper perspective on long-term thinking, read:
👉 Why Real Estate Is the Best Long-Term Investment

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My Role in Your Second Home Purchase

A second home purchase requires a slightly different lens than a primary residence.

Here is how I guide you:

  • Clarifying your timeline and long-term goals

  • Connecting you with lenders familiar with second-home financing

  • Structuring competitive offers in strong coastal markets

  • Navigating inspections specific to coastal properties

  • Reviewing flood insurance, zoning, and rental regulations

  • Negotiating beyond just price

  • Connecting you with trusted contractors, property managers, and local vendors

Whether you are buying in Cape Cod, along the South Shore, or elsewhere in Massachusetts, my role is to bring clarity to every step.

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Who This Is Perfect For

This approach is ideal if you are:

  • A MetroWest homeowner considering a Cape Cod second home

  • A Greater Boston family wanting a beach house for long-term use

  • A couple thinking ahead to retirement

  • A buyer who values both lifestyle and financial positioning

  • Someone curious about rental income but not looking to be a full-time investor

If that sounds like you, you’re in the right place.

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Let’s Talk Before You Fall in Love Online

The best time to discuss a second home purchase is before you fall in love with one on a listing site.

We’ll clarify:

  • Your financing strategy

  • Lifestyle priorities

  • Rental flexibility

  • Long-term hold plan

  • Exit strategy

That clarity makes the process calm, not reactive.

Calm guidance. Smart strategy. Exceptional results.

If you are considering buying a Cape Cod beach house or second home in Massachusetts, I would love to help you think through the strategy.

Reach out and let’s explore what the right second property looks like for you.

Alison Borrelli
REALTOR®
Berkshire Hathaway HomeServices Commonwealth Real Estate

Our Testimonials

See why our clients love working with us

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Vadim G.

Alison was the seller's agent when we were buying a house. She was a pleasure to deal with: patient, flexible, and very knowledgeable about the property she represented. She was responsive throughout the whole process, and made...
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Buyer

Keys have been retrieved! Thank you again for everything, Alison. We both really enjoyed getting to know you. We look forward to carrying on the legacy of 29 Cotton!
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Seller

Alison did an exceptional job in every aspect of the sale. She understood the market, helped us price the house correctly, staged it beautifully, negotiated skillfully with the buyers, and handled all of the many logistics nece...
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Elizabeth & David S.

Alison Borrelli came highly recommended to us by our neighbors, who put their home on the market and sold prior to our listing with her and Berkshire Hathaway. We interviewed other realtors and found her to be exceptional. We w...
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Adam D.

Alison was a wonderful partner to have in my search for an office. Her knowledge of Needham real estate and regulations was invaluable as I navigated the process of opening. I look forward to working with Alison in the future a...
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Angelica C.

We had an amazing experience with Allison Borrelli as our realtor. We were moving from California to Massachusetts. The service was beyond what we expected, she never hesitated to help us during the transition making the move e...
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Jenna R.

Alison was amazing from start to finish! She was prompt to return calls and emails and was always available. We’d love to use her again.
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Hicham C.

It was a pleasure working with Alison. She did a great job marketing our Needham property. We loved the accent pieces that were added for staging; the pictures turned out great as a result. Overall it was a smooth transaction.
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Emma B.

We would highly recommend Alison for all your real estate needs. Alison helped us purchase a house while we lived in another state. She truly was our eyes, ears on the ground; Alison has so much local knowledge & expertise. We ...
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Jim R.

I got to know Alison in the Spring of 2023 when I needed to sell a house I owned. Alison was referred to me by a good friend. When Alison and I first met to discuss the sale, Alison came to that meeting fully prepared with a ma...
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Liz S.

Alison Borelli came highly recommended to us by our neighbors, who put their home on the market and sold prior to our listing with her and Berkshire Hathaway. We interviewed other realtors and found her to be exceptional. We wa...
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Carol R.

Being new to the country, Alison has been absolutely Amazing! She helps us every step of the way. Coming from another country, and spoke with her regularly. She kept us updated with what is on the Market. She also took time out...
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Simon F.

Alison gave my wife and I an excellent area tour when we were considering relocating to the Boston area. She was very knowledgeable, easy to interact with and quickly understood what we were looking for. Highly recommended.
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Zoe P.

Alison was fantastic! She was incredibly knowledgeable, helpful and supportive. We could not have asked for a better agent! Would definitely recommend her and if we needed to buy another home - we’d use her again without hesita...
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Nelson H.

Alison Borrelli was everything I could have hoped for in a Realtor. She helped me organize the arduous tasks involved in preparing to put a house on the market in a number of ways. Having been in the home for 42 years, she was ...
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Nestor & Anna

It was a pleasure working with Alison on the sale of our home and we would highly recommend her to anyone buying or selling. Alison impressed us from the first meeting with her preparation, candidness, and experience in the loc...
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MB

Working with Alison Borrelli is a pleasure. She is professional , update to date with the current market. There truly is no one better!
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Jeanne B.

I have been working with Alison now for about a year and half on selling my Mom's home. My daughter and I want to say that Alison was personable, caring, warm, and upbeat! She helped us in so many ways. Always, making great sug...
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Tracey M.

Have dealt with Alison on 2 separate purchases and both experiences were excellent. We highly recommend.
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Giraldo H.

Alison is a delight to work with; from the very start, she made us feel welcome and informed with her amazing knowledge, insight, and recommendations. She clearly listened to what we needed and helped us find the perfect fit fo...
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Contact Details

Alison Borrelli

Phone

(617) 257-3012

Email

[email protected]

Address

1089 Great Plain Ave Needham MA 02492

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