Rupert, VT Homes for Sale

Q: What are the most popular zip codes in Rupert, VT?

The most popular zip codes in Rupert, VT include 05776 , 12832 , 05251 , 12865 and 05250 .

/59
$269,500
- 2 Beds
- 1 Bath
- 890 Sq Ft
3606 Kent Hollow Rd, Rupert, VT 05776

The details, craftsmanship and enchanting +/-9 surveyed acre setting is right out of a fairy tale. A perfect Vermont getaway retreat with the sounds of Oven Brook at your door- complete with foot bridge to your own back meadow where you can take in the views overlooking the gorgeous Kent Hollow setting. The c1865 antique cabin is loaded with character – wide-plank “bow-tie” floors, log doors

Scott McChesney McChesney RE, Inc.

3606 Kent Hollow Rd, Rupert, VT 05776
/41
$285,000
- 2 Beds
- 1 Bath
- 1,400 Sq Ft
3264 Route 153, West Rupert, VT 05776

This neat and tidy single story home has been completely renovated from top to bottom, offering comfort, efficiency, and style. Updates include all new metal roof, vinyl siding, thermopane windows, propane hot-air heating system with heat pump central air conditioning, appliances, kitchen cabinets, counters, and hardwood flooring. Also updated plumbing, fiber optic internet, new electrical

Scott McChesney McChesney RE, Inc.

3264 Route 153, West Rupert, VT 05776
/51
$675,000
- 3 Beds
- 2.5 Baths
- 2,208 Sq Ft
1148 Kent Hollow Rd, West Rupert, VT 05776

Country charm at the foot of Shatterack Mountain. Nestled in a classic Currier & Ives setting, this exceptional Cape Cod style home and barn sit on over 37 private acres, accessed by a a picturesque bridge over White Creek. Built by craftsman Mark Breen and inspired by a 300 year old Connecticut Cape, this home showcases timeless period detailing with crown molding and picture windows.

Margretta Fischer Wohler Realty Group

1148 Kent Hollow Rd, West Rupert, VT 05776
/57
$1,795,000
- 5 Beds
- 4.5 Baths
- 3,218 Sq Ft
5491 Vt Route 315, Rupert, VT 05776

Luxury home, move-in ready, on 5+ peaceful acres with protected panoramic mountain views and stream frontage, this fully renovated 1909 Federal offers timeless character with a like-new feel—just 2.5 miles from the Dorset Green and dining but away from the bustle. Every inch of the main home has been meticulously updated with premium materials and workmanship. A custom walnut kitchen with

Annette Gallo Real Broker LLC

5491 Vt Route 315, Rupert, VT 05776

Vermont Bennington County Rupert

Why Live in Rupert

Rupert, Vermont, nestled in the Taconic Mountains near the New York border, embodies rural charm with its picturesque farm village setting. The village center, featuring a general store, post office, and churches, reflects a classic small-town atmosphere. Historic buildings, like the Carver House, add to the area's character. Housing options range from historic Colonials and midcentury Cape Cods to large farmhouses and contemporary homes, many offering scenic views of rolling farmland or mountains. The Delaware and Hudson Rail-Trail, running along the Indian River, provides opportunities for hiking, biking, and fishing, while the Merck Forest & Farmland Center offers educational nature programs and trails. Sherman's Store, a staple since the 1850s, sells local products and serves meals, with more shopping available in nearby Dorset and Manchester. Community life is vibrant, with the Rupert Village Trust hosting social events in the historic Sheldon General Store. Students in Rupert have a school choice program, with options in Vermont and New York. Travel is facilitated by Vermont routes 30, 153, and 315, with the Rutland Regional Medical Center 35 miles away and Albany International Airport 60 miles away.

Learn more about living in Rupert

Frequently Asked Questions

What is the average home price in Rupert, VT?

Homes for sale in Rupert, VT have an average home price of $540,140.

Are home prices dropping in Rupert?

Yes, home prices in Rupert are down 35% in the last 12 months.

How many homes have sold over the last 12 months in Rupert, VT?

8 homes have sold in Rupert, VT over the last 12 months.

What are the most popular zip codes in Rupert, VT?

The most popular zip codes in Rupert, VT include 05776, 12832, 05251, 12865 and 05250.

How much do you need to make to afford a house in Rupert?

The median home price in Rupert is $387,000. If you put a 20% down payment of $77,400 and had a 30-year fixed mortgage with an interest rate of 6.35%, your estimated principal and interest payment would be $1,930 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $83K a year to afford the median home price in Rupert.

How are the schools in Rupert, VT?

Rupert, VT has highly rated public and private schools. Some of the best schools in Rupert based on Niche Grades are Mettawee Community School, The Dorset School and Salem Elementary School. Browse all the schools in Rupert, VT to learn more.

Home Trends in Rupert, VT

On average, homes in Rupert, VT sell after 103 days on the market compared to the national average of 52 days. The median sale price for homes in Rupert, VT over the last 12 months is $365,500, down 39% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$365,500

Median Single Family Sale Price

$365,500

Average Price Per Sq Ft

$261

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

3.00

Median List Price

$387,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

-39%

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