Rupert, VT House for Sale

/29
$499,000
- 2 Beds
- 2 Baths
- 2,250 Sq Ft
100 Holly's Way, Rupert, VT 05768

Long driveway to a Private setting with lots of room to hike, hunt or just enjoy the peace and quite. Possible subdivision. House is warm and cozy with a large sleeping loft on the second floor. There is a foundation in place for an out building.

Charles Mauro Josiah Allen Real Estate, Inc.

100 Holly's Way, Rupert, VT 05768

Vermont Rupert

Why Live in Rupert

In Southwestern Vermont on the border of Upstate New York, Rupert offers rural living in the Taconic Mountains. “It’s a real classic Vermont scene—a little farm village cultivated by all the land around it,” says Scott McChesney, principal broker of McChesney Real Estate, who has worked in the region for more than 40 years. Farms, rolling hills and forested mountains exhibit the natural beauty of Rupert, where a tiny village center captures the small-town atmosphere with a general store, post office and a few churches. There are also a number o ...

Learn more about living in Rupert

Home Trends in Rupert, VT

On average, homes in Rupert, VT sell after 60 days on the market compared to the national average of 49 days. The median sale price for homes in Rupert, VT over the last 12 months is $356,000, down 43% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$356,000

Median Single Family Sale Price

$365,500

Average Price Per Sq Ft

$200

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

1.70

Median List Price

$395,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

-43%

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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.