19 of the Prettiest Homes That Hit the Market in 2019

From cranberry bogs and 116 acre estates to converted bakeries and churches, here are some of the most popular listings of the year.


Photo via Compass

A Castle-Like Construction in Brookline
Featured in January 2019
120 Rawson Road, Brookline
Price: $6,250,000
Size: 6,313 square feet
Bedrooms: 4
Baths: 3.5

Status: Off market

Photo via Campion & Company

A Massive Manor in Jamaica Plain
Featured in April 2019
96 Rockwood Street, Jamaica Plain
Price: 3,950,000
Size: 15,059
Bedrooms: 11
Baths: 5.5

Status: On the market. Claim this Gothic Victorian and its nearly five acres of land for yourself.

Photo by Jake Belcher

A Converted Firehouse Condo in Jamaica Plain
Featured in May 2019
16 Walk Hill St. #2, Boston
Price: $319,000
Size: 398 square feet
Bedrooms: 1
Baths: 1

Status: Off market

Photo by Joel Gross Architectural and Residential Photography

A 250-Year-Old Former Bakery in Marblehead
Featured in May 2019
9 Merritt St., Marblehead
Price: $825,000
Size: 2,135 square feet
Bedrooms: 4
Baths: 2

Status: On the market. Here’s your chance to own a piece of pre-revolutionary history.

Photo via Maria Mardikis/BostonREP

A Neoclassical Marvel in Manchester-by-the-Sea
Featured in June 2019
3 Colburn Road, Manchester
Price: $2,450,000
Size: 6,120 square feet
Bedrooms: 2
Baths: 3.5

Status: On the market. From its Grand Loggia to its classical rotunda, this manse is fit for royalty.

Photo via Gibson Sotheby’s International Realty

A Luxe Condo in a Converted Catholic Church
Featured in June 2019
45 West Broadway #301, South Boston
Price: $839,000
Size: 877 square feet
Bedrooms: 1
Baths: 1

Status: Off market

Photo via Gibson Sotheby’s International Realty

A Glass House on a Cape Cod Island
Featured in July 2019
113 4th St., Wellfleet
Price: $1,545,000
Size: 2,332 square feet
Bedrooms: 3
Baths: 2

Status: Off market

Photo by Greg Premru

A Manchester Home with Its Own WWII Watchtower
Featured in August 2019
12 Smith’s Point Road, Manchester-by-the-Sea
Price: $11,400,000
Size: 5,944
Bedrooms: 6
Baths: 8

Status: On the market. Got $11.4 million to spend? This oceanfront estate with an infinity pool and 11-story tower is calling your name.

Photo by Elyssa Cohen

A Quaint Oceanfront Cottage in Provincetown
Featured in September 2019
649 Commercial St., Provincetown
Price: $1,649,000
Size: 1,125 square feet
Bedrooms: 5
Baths: 1.5

Status: On the market—and for $150k less than when we first featured it.

Photo by Maria Mardikis at BostonREP

A Ritzy and Historic Manor in Salem
Featured in September 2019
329 Essex St., Salem
Price: $1,395,000
Size: 6,352 square feet
Bedrooms: 5
Baths: 2.5

Status: On the market. Old-school opulence oozes from this Victorian mansion.

Photo by Kirk Erickson/Mainescape Media

A Maine Country Lodge with 16 Bedrooms and 110 Acres
Featured in September 2019
45 E Andover Road, Andover, Maine
Price: $1,200,000
Size: 9,600 square feet
Bedrooms: 16
Baths: 7

Status: On the market—and for a sweet $125 per square foot.

Photo via LandVest

A Grown-Up Treehouse in Western Massachusetts
Featured in October 2019
720 West Road, Richmond
Price: $2,450,000
Size: 4,228 square feet
Bedrooms: 4
Baths: 4

Status: Off market

Photo via Engel & Völkers By the Sea

An Essex Estate with a Cranberry Bog
Featured in October 2019
57 Pond St., Essex
Price: $1,490,000
Size: 5,674 square feet
Bedrooms: 5
Baths: 4

Status: On the market. What could be more New England? Plus, pen the next great novel in its standalone studio.

Photo by Ren Nikerson via William Pitt Sotheby’s International Realty

A Fairy Tale Compound in Tyringham
Featured in November 2019
75 Main Road # 77, Tyringham
Price: $1,295,000
Size: 7,750 square feet
Bedrooms: 7
Baths: 6

Status: On the market. Towers, a lily pond, and a real-life gingerbread house, anyone?

Photo via Berkshire Property Agents

A Breathtaking Estate in the Berkshires
Featured in November 2019
716 Rannapo Road, Sheffield
Price: $790,000
Size: 3,524 square feet
Bedrooms: 6
Baths: 4

Status: On the market. Want a view you’ll never tire of? Take a gander at this gem.

Photo via William Raveis Real Estate

A Historic Bed and Breakfast in Nantucket
Featured in November 2019
10B Cliff Road, Nantucket
Price: $5,950,000
Size: 4,744 square feet
Bedrooms: 17
Baths: 19

Status: On the market. Make your long-held fantasy of owning a B&B a reality.

Photo by Jim Mauchly

An Actual Castle on a Vermont Mountaintop
Featured in November 2019
1599 Cavendish Gulf Road, Vermont
Price: $2,599,000
Size: 7,945 square feet
Bedrooms: 7
Baths: 6

Status: On the market. Get away from it all in this palatial residence with its own amphitheater.

Photo via Jeff Stephens

An Architect’s Townhouse Filled with Lofts and Ladders
Featured in December 2019
178 Harvard St. #178, Cambridge
Price: $1,495,000
Size: 2,341 square feet
Bedrooms: 3
Baths: 2.5

Status: On the market. Complete with store-front style windows, these multi-level digs are some of Cambridge’s coolest.

Photo via Legacy Properties/Sotheby’s International Realty

A Color-Splashed Renovation in Portsmouth
Featured in December 2019
129 State St., Portsmouth, NH
Price: $2,950,000
Size: 3,859 square feet
Bedrooms: 3
Baths: 4

Status: On the market. If you love color, you’ll love this jazzy home.

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