Why Right-Sizing Is Better Than Downsizing when Buying Your Next Home

How to find your just-right home in The Pinehills

October 23, 2026    

Thinking about downsizing South of Boston? At The Pinehills, in Plymouth, MA, we call it right-sizing: finding a home that fits the life you're living now, with less upkeep, and without giving up beautiful finishes or a full, connected life.

Has Your Home Started to Feel Like More Than You Need?

It's a story we hear often. Someone comes to see us from a large home, maybe elsewhere on the South Shore or on the Cape. The kids are grown. The rooms that once held birthday parties and holiday chaos are mostly quiet now, and the house has become a job: more rooms to clean, more roof and lawn to worry about, more of the year spent maintaining instead of enjoying. They aren't looking to give anything up. They're looking for a home that fits.

2019 05 PH Beer Garden WEB Cutrona 2131

What Is the Difference Between Downsizing and Right-Sizing?

Downsizing is about less. Right-sizing is about fit. For some people, that means one-level living and fewer rooms. For others, it means a first-floor primary suite with space for visiting grandkids, a home office, or a parent moving in. And for some, it means an apartment home where you can lock up and travel without a second thought. Growing families, blended families, multigenerational families: since The Pinehills began, we've known the answer is never one-size-fits-all.

How Much Home Maintenance Is Handled for You?

More than you might expect. Every home in The Pinehills, single-family or condominium, new or resale, has its driveway and walkways shoveled, roads plowed, trash picked up, and common areas beautifully maintained. In condominium neighborhoods, much of the exterior upkeep is handled, too. For anyone who has spent a February morning digging out the end of the driveway, snow removal isn't a small perk. It's a whole new winter.

Everyday life is close by, too. The Pinehills Village Green has more than 30 shops, restaurants, and services, including The Market, the Mayflower Beer Garden, the post office, and Mirbeau Inn & Spa. And 10+ miles of walking trails connect neighborhoods to it all.

Walking Trail in Winter Ken Grille

What Kinds of Homes Are Available in The Pinehills?

With more than 60 neighborhoods and thousands of homes, from cottages to condominiums, single-family and apartment homes, there are many ways to right-size:

Neighborhood Builder Home style Prices from
Aurora Sky The Green Company New 55+ Condominium townhomes on The Pinehills Ridge, some with Cape Cod Bay views upper $800s
Broadleaf Toll Brothers New condominium townhomes near the Village Green upper $800s
Jones Pond Way Barefoot Cottage Company New pond-front and park-front cottages, condominium ownership the $800s
Owls Nest Toll Brothers New single-family homes with first-floor primary suites; Regency Collection is 55+ the $900s
Symington Woods Whitman Homes New attached single-family townhomes, close to the Village Green upper $700s
Apartment Homes Various Luxury apartment homes for rent Rent varies, contact
leasing offices
directly
Resale Homes Many builders Single-family homes, cottages, townhomes, and condominiums upper $600s to $2 million

Our new home neighborhoods are active construction sites, so please start at the model homes where applicable and visit only with a builder or sales representative. Call 508.209.2000 for information about visiting any neighborhood.
Barefoot Cottage Company Cobblestone Street with Dog Pinehills

Why Do Resale Homes in The Pinehills Feel So Young?

They are! The first home in The Pinehills was sold in 2000, so even the earliest homes here are only about 25 years old, and many are much newer. That's quite a difference from the rest of Massachusetts, where the typical home is about 60 years old, according to U.S. Census data, one of the oldest housing stocks in the country.

Pinehills Brokerage Services REALTORS® sell homes in The Pinehills every day. They know who built each home and how, and they understand the details that vary from one neighborhood to the next: association rules and fees, amenities, and the things a buyer should know that aren't obvious to anyone who doesn't sell here regularly. When you're shopping for a home in The Pinehills, that knowledge gives you a real edge. Browse resale homes

Poets walking

Will a Smaller Home Mean a Quieter Life?

Only if you want it to. Everyone who lives in The Pinehills belongs to the Stonebridge Club, our amenity center, with two pools, tennis, fitness and wellness classes, and more than 80 resident clubs and groups. Neighbors become friends over coffee on the Village Green, on the trails, or on Pinehills Golf Club's two championship daily-fee courses. Or simply enjoy a quiet walk through 3,200 acres, where only one-third of the land is built upon and two-thirds remains for open space and recreational use. Additional amenities vary by neighborhood.

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Right-Sizing in The Pinehills: Common Questions

Is The Pinehills a good place to downsize?
Yes. People come to The Pinehills in Plymouth, MA, from larger homes around Boston, on the South Shore, Cape Cod, and well beyond, looking for less upkeep without giving up quality, comfort, or connection.

Where is The Pinehills?
The Pinehills is an award-winning village
in "America's Hometown," beautiful Plymouth, MA. Located right off Route 3 at Exit 7, about an hour from Boston and ten minutes from Cape Cod. At 5 square miles, The Pinehills is larger than some Massachusetts towns!

What kinds of homes are available in The Pinehills?
New construction includes cottages at Jones Pond Way by Barefoot Cottage Company, single-family homes at Owls Nest and condominium townhomes at Broadleaf by Toll Brothers, attached single-family townhomes at Symington Woods by Whitman Homes, and condominium townhomes at Aurora Sky by The Green Company. Resale homes and luxury apartment homes are also available.

Are resale homes in The Pinehills a good option?
Yes. The first home in The Pinehills was sold in 2000, so the oldest homes are only about 25 years old, young by New England standards, and many are much newer.

Do you have to be a certain age to live in The Pinehills?
No. A few neighborhoods are designated 55+, which generally means one member of the household must be 55 or older, and most are open to all ages.

What maintenance is included for every home?
Every home in The Pinehills, single-family or condominium, gets driveway and walkway shoveling, road plowing, trash pickup, and maintained common areas. Additional maintenance varies by neighborhood.

Ready to See What Fits?

If your home has started to feel like more (or less!) than you need, trust that feeling. Call us at 508.209.2000 to plan your visit, or make an appointment here. (For apartment homes, please contact the leasing offices directly.)

Let's find your just right! Use the form below and let us know what your heart desires:

Welcome Center

The Summerhouse

33 Summerhouse Drive   •   Plymouth, MA 02360
Open by appointment Wednesday–Sunday, 10am–4pm
888.209.8880

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