20 of the Prettiest Homes That Hit the Market in 2020

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Our On the Market series features extraordinary homes for sale in the region every day. But even among the standouts, there are standouts. Here are 20 of our favorites from 2020.


Photo by Ren Nickson

Midcentury Modern Digs with an Airstream Trailer Guest House
Featured in January
10 Paradise Lane, New Milford, CT
Price: $1,450,000
Size: 3,035 square feet
Bedrooms: 3
Baths: 3

Status: Off market

Photo via Four Seasons Sotheby’s International Realty

A New Hampshire Estate with a Ski Lodge, “Chocolate House,” and 96 Acres
Featured in February
248 Huntington Road, Henniker, New Hampshire
Price: $3,300,000
Size: 14,214 square feet
Bedrooms: 14
Baths: 16

Status: Off market

Photo by Marc Bartholomew

A Blissful Island Escape off the Coast of Maine
Featured in March
82 Common Lane, Southwest Harbor, ME
Price: $5,950,000
Size: 7,100 square feet
Bedrooms: 7
Baths: 7

Status: Off market

Michael Bowman/Michael Bowman Photography

An A-Frame Oasis with Midcentury Modern Appeal
Featured in March
112 Norfolk Road, Litchfield, CT
Price: $835,000
Size: 4,234 square feet
Bedrooms: 4
Baths: 4

Status: Off market

Photo via The Knowles Company

A Lighthouse Keeper’s Enchanting Island Home
Featured in April
99 Lighthouse Road, Isle Au Haut, ME
Price: $1,975,000
Size: 2,500 square feet
Bedrooms: 4
Baths: 2

Status: On the market. It doesn’t get more idyllic than this.

Photo by Drone Home Media

A Versailles-Inspired Chateau in Worcester
Featured in April
28 Westwood Drive, Worcester
Price: $2,188,000
Size: 5,419 square feet
Bedrooms: 5
Baths: 5.5

Status: Off market

Photo by Scott Miele, Honey Bee Productions

A Playful Victorian Condo in Portland
Featured in May
73 Spruce St. #1, Portland, ME
Price: $625,000
Size: 1,517 square feet
Bedrooms: 2
Baths: 1.5

Status: Off market

Photo via Lila Delman Real Estate

An Indoor-Outdoor Living Resort in Rhode Island
Featured in May
79 Shore Road, Bristol, RI
Price: $5,750,000
Size: 5,735 square feet
Bedrooms: 6
Baths: 9

Status: Off market

Photo by Brian Doherty Photography

A Radiant Haven in Hingham
Featured in May
25 Rockwood Road, Hingham
Price: $929,000
Size: 1,940 square feet
Bedrooms: 3
Baths: 2

Status: Off market

Photo by Kallmekg Visuals

A Roaring Twenties Great Estate in Lenox
Featured in June
101 & 95 Yokun Ave., Lenox
Price: $5,900,000
Size: 11,748 square feet
Bedrooms: 13
Baths: 10.5

Status: On the market. Create your own Jazz Age in this rambling Western Mass home.

Photo via Steven Cohen Team/Keller Williams Realty

A Splendid Duplex Condo in Concord Square
Featured in June
15 Concord Square #2, South End
Price: $1,375,000 square feet
Size: 1,270 square feet
Bedrooms: 2
Baths: 1.5

Status: Off market

Photo by Anfuso Imaging

An Extravagant, Literary Brownstone Duplex in Back Bay
Featured in July
86 Marlborough St. #3, Boston
Price: $3,250,000
Size: 2,520 square feet
Bedrooms: 3
Baths: 3

Status: On the market. It’s a book lover’s paradise.

Photo via Keller Williams Realty

A Shining and Serene Retreat in Freeport
Featured in July
230 Flying Point Road, Freeport, ME
Price: $1,375,000
Size: 2,600 square feet
Bedrooms: 3
Baths: 3

Status: Off market

Photo by Jonathan Watkins, JFW Photography

A Cute and Distinctive Estate in Truro
Featured in August
91 Castle Road, Truro
Price: $1,875,000
Size: 2,646 square feet
Bedrooms: 3
Baths: 3

Status: On the market—and the price has dropped by a cool $120,000 since we first featured it.

Photo by Michael Bowman Photography

A Connecticut Cottage Inspired by a Castle
Featured in September
299 Great Hollow Road, Cornwall, CT
Price: $1,395,000
Size: 2,599 square feet
Bedrooms: 4
Baths: 3.5

Status: Off market

Photo via The Knowles Company

A Petite Charmer on a Maine Island
Featured in September
56 Hillcrest Circle, Southwest Harbor, ME
Price: $460,000
Size: 820 square feet
Bedrooms: 2
Baths: 2

Status: On the market. It’s less than 1,000 square feet but it’s chock-full of charm.

Photo by Jake Rubin

A Stately, Sprawling Victorian Townhouse in Newton
Featured in October
53 Vista Ave. Unit A and B, Newton
Price: $2,450,000
Size: 3,707 square feet
Bedrooms: 2
Baths: 3.5

Status: Off market

Photo by Madore Photography

A Cheerful, Historical Gem in Westborough
Featured in November
9 Central St., Westborough
Price: $799,900
Size: 3,100 square feet
Bedrooms: 4
Baths: 2

Status: Off market 

Photo via Engel & Völkers Boston

A Glorious Gloucester Compound on the Oceanfront
Featured in December
9 Drumhack Road, Gloucester
Price: $9,000,000
Size: 10,400 square feet
Bedrooms: 3
Baths: 6

Status: On the market. Does a heated pool at the edge of the ocean interest you?

Photo by Michael Osean

A Whimsical Work of Art in Newport
Featured in December
5 Third St., Newport, RI
Price: $620,000
Size: 1,098 square feet
Bedrooms: 2
Baths: 1.5

Status: On the market. You’ve just gotta see this ridiculously adorable cottage for yourself.

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Source URL: https://www.bostonmagazine.com/property/2020/12/24/prettiest-homes-on-the-market-2020/