Ever wonder what it’s like to live large in­­ one of the nation’s ol­­dest cities?

Boston hosts some of the country’s most iconic colonial landmarks, and also some of the most desired real estate in the country.

Though famous residents like Tom Brady and his wife Gisele Bündchen are listing their mansion in Brookline, Massachusetts for sale, their $39.5 million dollar property isn’t the only luxury spot on the market in New England.

Here’s what it looks like, and how much it costs to live it up on the water in the greater Boston area, courtesy of Compass properties:

Cohasset, Mass.


6 bedrooms

7.5 bathrooms

6,800 sq. feet

The direct waterfront property about an hour outside of Boston hosts easy harbor access with plenty of lawn space and amenities to boot. Built in 1906, the estate showcases panoramic views of the peninsula, while providing an unmatched level of privacy next to downtown Cohasset. According to Compass agent Kevin Lewis, the property is one of the last grand Cohasset estates available on the market.


Custom tennis court

Boathouse & private dock

Outdoor heated pool with spa & pool house

The Cohasset, Mass. home sports a heated outdoor pool. (Courtesy: Compass)

Gloucester, Mass.


9 bedrooms

9.5 bathrooms

9,982 sq. feet

This Eastern Point masterpiece literally hugs the water. The Stoneacre estate’s floor-to-ceiling windows make it seem as if those living inside are almost floating on the Boston blue. Nestled about an hour-and-a-half northeast of Boston, the property has its original wine cellar from the 1920s. According to the listing by The Bushari Team with Compass, “the space is fit for both intimate dinners and grand celebrations.”

Billiards room

The Gloucester, Mass. home has an entertainment area that includes a billiards room. (Courtesy: Compass)

Original wine cellar

The original wine cellar built in the 1920s. (Courtesy: Compass)

Wet bar

The downstairs wet bar meant to host guests on the property. (Courtesy: Compass)

Duxbury, Mass.


5 bedrooms

6.5 bathrooms

8,600 sq. feet

Living on the Cape never felt so historic: this property was built in 1747. Located little over an hour southeast of Boston, the woman who invented the chocolate chip cookie, Ruth Wakefield, once lived here. Count on a chef’s kitchen and plenty of dining room space to appreciate the meal. Listed by The Bushari Team at Compass, anyone enjoying the living space has access to “breathtaking water views from almost every window.”

Koi pond

The home has a path that surrounds a koi pond. (Courtesy: Compass)

Oceanfront dock

The backyard leads to an oceanfront dock. (Courtesy: Compass)

Heated outdoor pool and spa

The yard includes an outdoor heated pool and spa. (Courtesy: Compass)

Wetland nature trail

Access to a nature trail features wetland and conservation areas. (Courtesy: Compass)


Edgartown, Mass.


8 bedrooms

11.5 bathrooms

10,099 sq. feet

Not meant for the average commute, this Katama Bay home could serve as a getaway from the Boston lifestyle. Known locally as “Chappy,” architect Patrick Ahearn designed the home with an open plan, sitting on nearly 6 acres of private property. Bonus: the home is equipped with smart-home technology. Compass listing agent Jamie Curtis describes the soon-to-be-listed Martha’s Vineyard location as one that provides “magical sunsets and extensive sandy beaches [that] combine to create relaxing outdoor environs.”

Outdoor space

Open floor plans

Newport, R.I.


7 bedrooms

9.5 bathrooms

10,000 sq. feet

Also a bit of a drive south of Boston, and just over the border in Rhode Island, Seaward sits on about 45 acres of property located on the waterfront with two homes. Its former owners include the likes of businessman and real estate magnate John Jacob Astor, and later Jimmy Van Alen, the co-founder of the Tennis Hall of Fame.

Jeannemarie Conley, who is listing the estate, describes the outdoor space including an “alluring seaside infinity pool overlooks two private moorings providing water access to a secluded cove.”