$529,000
3 Bed • 3 Bath • 2,504 Sq. Ft.
104 Ayers Court
Montgomery, NY 12549
Listed with KW Hudson Valley United
$440,000
Est. $3,029/moChester, NY 10918 · Orange County
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Historic Colonial Era Home in the Heart of Sugar Loaf, NY. Located just 60 minutes from NYC. Zoned Residential/Commercial. Step into history with this one-of-a-kind 1,750 sq. ft. Colonial era home, where 18th-century charm meets 21st-century opportunity — right in the heart of the artisan hamlet of Sugar Loaf, NY. Built in 1770, this unique property features:• One of a kind Colonial era home, featuring original exposed hand-hewn beams, barn siding walls, and a fireplace• Two spacious workshops/studios – ideal for artists, entrepreneurs, or makers – currently a woodcarvers workshop. • A must-see, living piece of history full of soul and story• Stunning view of Sugar Loaf Mountain right out your front door. Zoned commercial/residential, this home offers the perfect blend of live-work potential — ideal for a workshop, gallery, studio, or cozy retreat. Just steps away:• 2 popular restaurants• A vibrant performing arts center• Local breweries with live music• Coffee shop/ Roaster & Brunch House• Year-round craft markets & community events. Sugar Loaf is a renowned creative hub, and this home is at the very center of it all. Nestled in the heart of Sugar Loaf’s artisan community, this unique home and shop was long owned by a cultural mainstay — a woodcarver, painter, entertainer, and local luminary whose influence helped shape Sugar Loaf’s identity as an artists’ village back in the mid 1960’s.  This property offers more than walls and beams. Full of character and creative potential, this property is perfect for artists, craftsmen, woodworkers or anyone drawn to a vibrant, storied community. It offers a living canvas for makers and dreamers to carry forward a tradition of creativity. Don't miss your chance to own a timeless treasure in one of the Hudson Valley’s most beloved villages.
As reported by the listing office; verify enrollment with the district.
Listed with Greene Realty Group · Derek J. Greene · Source: OneKey MLS
Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Sep 17, 2026, 3:09 PM ET. ©2026 One Key MLS.
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Market Insights
Current Listings
New in the last 30 days
28
Sep 2026
Average Price
Active listings
$911,991
Sep 2026
Average Days on Market
Active listings
136 days
Sep 2026
Computed from 108 active OneKey MLS listings in Chester, NY.
$529,000
3 Bed • 3 Bath • 2,504 Sq. Ft.
104 Ayers Court
Montgomery, NY 12549
Listed with KW Hudson Valley United
$465,000
3 Bed • 1 Bath • 1,320 Sq. Ft.
13 Columbia Avenue
Middletown, NY 10940
Listed with eXp Realty
$355,000
2 Bed • 2.5 Bath • 1,150 Sq. Ft.
49 Matthews Lane
Washingtonville, NY 10992
Listed with RE/MAX Benchmark Realty Group