Rupert, VT Homes

/39
Not Listed For Sale

4145 Route 153, Rupert, VT 05768
- 5 Beds
- 4 Baths
- 3,700 Sq Ft
- Built 1850
4145 Route 153, Rupert, VT 05768

Last Sold Summary
- $241/SF
- 19 Days On Market
Last Sold Price $890,000

Last Listing Agent David Shehadi Josiah Allen Real Estate, Inc.

/30
Not Listed For Sale

5491 Vt Route 315, Rupert, VT 05776
- 3 Beds
- 2.5 Baths
- 2,654 Sq Ft
- Built 1905
5491 Vt Route 315, Rupert, VT 05776

Last Sold Summary
- $268/SF
- 30 Days On Market
Last Sold Price $712,000

Last Listing Agent David Halligan Four Seasons Sotheby's Int'l Realty

/38
Not Listed For Sale

455 Pawlet Mountain Rd, Rupert, VT 05768
- 3 Beds
- 2.5 Baths
- 3,955 Sq Ft
- Built 1988
455 Pawlet Mountain Rd, Rupert, VT 05768

Last Sold Summary
- $173/SF
- 3 Days On Market
Last Sold Price $685,000

Last Listing Agent Kristin Comeau TPW Real Estate

/40
Not Listed For Sale

2528 Vt Route 30, Rupert, VT 05768
- 4 Beds
- 1.5 Baths
- 1,800 Sq Ft
- Built 1805
2528 Vt Route 30, Rupert, VT 05768

Last Sold Summary
- $66/SF
- 30 Days On Market
Last Sold Price $118,000

Last Listing Agent Scott McChesney McChesney RE, Inc.

/33
Not Listed For Sale

166 McKeighan Rd, Rupert, VT 05776
- 4 Beds
- 5 Baths
- 5,956 Sq Ft
- Built 2000
166 McKeighan Rd, Rupert, VT 05776

Last Sold Summary
- $294/SF
- 226 Days On Market
Last Sold Price $1,750,000

Last Listing Agent Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

/17
Not Listed For Sale

0 Vt Route 315 Unit 4867138, Rupert, VT 05768
0 Vt Route 315 Unit 4867138, Rupert, VT 05768

Last Sold Summary
- 184 Days On Market
Last Sold Price $33,000

Last Listing Agent Laura Beckwith Josiah Allen Real Estate, Inc.

/40
Est $412,695 Not Listed For Sale

193 East St, West Rupert, VT 05776
- 3 Beds
- 3 Baths
- 1,984 Sq Ft
- Built 1950
193 East St, West Rupert, VT 05776

Last Sold Summary
- 18% Above List Price
- $176/SF
- 8 Days On Market
Last Sold Price $350,000

Last Listing Agent Scott McChesney McChesney RE, Inc.

/40
Not Listed For Sale

2528 Vermont 30, Pawlet, VT 05761
- 4 Beds
- 1.5 Baths
- 1,952 Sq Ft
- Built 1805
2528 Vermont 30, Pawlet, VT 05761

Last Sold Summary
- $51/SF
- 13 Days On Market
Last Sold Price $99,500

Last Listing Agent Scott McChesney McChesney RE, Inc.

/5
Est $736,116 Not Listed For Sale

486 Rogers Rd, Dorset, VT 05251
- 3 Beds
- 2 Baths
- 2,068 Sq Ft
- Built 1771
486 Rogers Rd, Dorset, VT 05251

Last Sold Summary
- 43% Above List Price
- $249/SF
- 0 Days On Market
Last Sold Price $515,000

Last Listing Agent David Shehadi Josiah Allen Real Estate, Inc.

/36
Not Listed For Sale

348 Neilson Rd, Dorset, VT 05251
- 3 Beds
- 2.5 Baths
- 2,970 Sq Ft
- Built 1970
348 Neilson Rd, Dorset, VT 05251

Last Sold Summary
- $572/SF
- 236 Days On Market
Last Sold Price $1,700,000

Last Listing Agent David Shehadi Josiah Allen Real Estate, Inc.

/30
Not Listed For Sale

529 Antone Mountain View Rd, Rupert, VT 05768
- 3 Beds
- 2 Baths
- 2,016 Sq Ft
- Built 1976
529 Antone Mountain View Rd, Rupert, VT 05768

Last Sold Summary
- $308/SF
- 100 Days On Market
Last Sold Price $620,000

Last Listing Agent David Halligan Four Seasons Sotheby's Int'l Realty

/36
Est $313,912 Not Listed For Sale

1205 Sandgate Rd, Rupert, VT 05776
- 3 Beds
- 1.5 Baths
- 1,167 Sq Ft
- Built 1805
1205 Sandgate Rd, Rupert, VT 05776

Last Sold Summary
- 26% Above List Price
- $214/SF
- 147 Days On Market
Last Sold Price $250,000

Last Listing Agent Scott McChesney McChesney RE, Inc.

/17
Not Listed For Sale

0 Vermont 153, West Rupert, VT 05776
0 Vermont 153, West Rupert, VT 05776

Last Sold Summary
- 1 Day On Market
Last Sold Price $299,000

Last Listing Agent Scott McChesney McChesney RE, Inc.

/37
Not Listed For Sale

595 Antone Mountain View Rd, Rupert, VT 05768
- 2 Beds
- 2 Baths
- 1,382 Sq Ft
- Built 1980
595 Antone Mountain View Rd, Rupert, VT 05768

Last Sold Summary
- $253/SF
- 94 Days On Market
Last Sold Price $350,000

Last Listing Agent Laura Beckwith Josiah Allen Real Estate, Inc.

/40
Not Listed For Sale

625 Sykes Hollow Rd, Dorset, VT 05251
- 8 Beds
- 6 Baths
- 3,800 Sq Ft
- Built 1778
625 Sykes Hollow Rd, Dorset, VT 05251

Last Sold Summary
- $322/SF
- 174 Days On Market
Last Sold Price $1,225,000

Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

/20
Not Listed For Sale

2 Main St, Rupert, VT 05768
- 5 Beds
- 3 Baths
- 3,979 Sq Ft
- Built 1808
2 Main St, Rupert, VT 05768

Last Sold Summary
- $79/SF
- 8 Days On Market
Last Sold Price $314,900

Last Listing Agent Dick Thackston R.H. Thackston & Company

/31
Not Listed For Sale

63 Sykes Hollow Rd, Dorset, VT 05251
- 3 Beds
- 3.5 Baths
- 3,060 Sq Ft
- Built 2017
63 Sykes Hollow Rd, Dorset, VT 05251

Last Sold Summary
- $260/SF
- 551 Days On Market
Last Sold Price $795,000

Last Listing Agent Elena Atwill Four Seasons Sotheby's Int'l Realty

/14
Est $414,549 Not Listed For Sale

2826 Pawlet Mountain Rd, Pawlet, VT 05761
- 5 Beds
- 2 Baths
- 2,430 Sq Ft
- Built 1976
2826 Pawlet Mountain Rd, Pawlet, VT 05761

Last Sold Summary
- 94% Above List Price
- $88/SF
- 119 Days On Market
Last Sold Price $213,542

Last Listing Agent Lori Andrus-Winn New England Lakeside Realty

/25
Not Listed For Sale

521 Edgerton Road St, Rupert, VT 05761
- 6 Beds
- 4 Baths
- 2,400 Sq Ft
- Built 1988
521 Edgerton Road St, Rupert, VT 05761

Last Sold Summary
- $154/SF
- 361 Days On Market
Last Sold Price $369,900

Last Listing Agent Scott McChesney Lee D McChesney Real Estate

/79
Not Listed For Sale

2929 Vermont State Route 153, Rupert, VT 05768
- 4 Beds
- 3 Baths
- 4,000 Sq Ft
- Built 1818
2929 Vermont State Route 153, Rupert, VT 05768

Last Sold Summary
- $107/SF
- 13 Days On Market
Last Sold Price $429,500

Last Listing Agent Scott McChesney Lee D McChesney Real Estate

/48
Not Listed For Sale

60 Vermont State Route 313, Rupert, VT 05768
- 3 Beds
- 2 Baths
- 1,860 Sq Ft
- Built 1848
60 Vermont State Route 313, Rupert, VT 05768

Last Sold Summary
- $112/SF
- 179 Days On Market
Last Sold Price $209,000

Last Listing Agent Scott McChesney Lee D McChesney Real Estate

/40
Not Listed For Sale

60 Route 315, Rupert, VT 05768
- 3 Beds
- 2 Baths
- 1,860 Sq Ft
- Built 1850
60 Route 315, Rupert, VT 05768

Last Sold Summary
- $109/SF
- 13 Days On Market
Last Sold Price $202,500

Last Listing Agent Scott McChesney McChesney RE, Inc.

/40
Not Listed For Sale

4035 Kent, Rupert, VT 05776
- 2 Beds
- 2 Baths
- 1,400 Sq Ft
- Built 1970
4035 Kent, Rupert, VT 05776

Last Sold Summary
- $189/SF
- 754 Days On Market
Last Sold Price $265,000

Last Listing Agent Scott McChesney McChesney RE, Inc.

/12
Not Listed For Sale

xx By Rail Trail Corner Lewis and 153, Rupert, VT 05768
xx By Rail Trail Corner Lewis and 153, Rupert, VT 05768

Last Sold Summary
- 149 Days On Market
Last Sold Price $176,000

Last Listing Agent Laura Beckwith Josiah Allen Real Estate, Inc.

/10
Not Listed For Sale

863 Rogers Rd, Rupert, VT 05768
863 Rogers Rd, Rupert, VT 05768

Last Sold Summary
- 563 Days On Market
Last Sold Price $412,500

Last Listing Agent Andy Reed Four Seasons Sotheby's Int'l Realty

/40
Not Listed For Sale

6958 Route 153, Rupert, VT 05768
- 4 Beds
- 3.5 Baths
- 3,100 Sq Ft
- Built 1820
6958 Route 153, Rupert, VT 05768

Last Sold Summary
- $141/SF
- 581 Days On Market
Last Sold Price $438,000

Last Listing Agent Laura Beckwith Josiah Allen Real Estate, Inc.

/26
Not Listed For Sale

5251 Suncrest Rd, Rupert, VT 05768
5251 Suncrest Rd, Rupert, VT 05768

Last Sold Summary
- 321 Days On Market
Last Sold Price $295,000

Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

/22
Est $485,749 Not Listed For Sale

1271 Kent Hollow Rd, West Rupert, VT 05776
- 5 Beds
- 2.5 Baths
- 3,400 Sq Ft
- Built 1975
1271 Kent Hollow Rd, West Rupert, VT 05776

Last Sold Summary
- 143% Above List Price
- $59/SF
- 239 Days On Market
Last Sold Price $199,500

Last Listing Agent Scott McChesney Lee D McChesney Real Estate

/13
Est $271,305 Not Listed For Sale

166 East St, West Rupert, VT 05776
- 3 Beds
- 2 Baths
- 1,393 Sq Ft
- Built 1850
166 East St, West Rupert, VT 05776

Last Sold Summary
- 82% Above List Price
- $107/SF
- 5 Days On Market
Last Sold Price $149,000

Last Listing Agent William Mariano

/40
Not Listed For Sale

2774 Route 315, Pawlet, VT 05761
- 3 Beds
- 2 Baths
- 1,500 Sq Ft
- Built 2003
2774 Route 315, Pawlet, VT 05761

Last Sold Summary
- $166/SF
- 290 Days On Market
Last Sold Price $249,000

Last Listing Agent Michael Campbell Michael Craig Campbell Realty

/25
Est $372,220 Not Listed For Sale

262 Hidden Valley Rd, West Rupert, VT 05776
- 2 Beds
- 2 Baths
- 2,500 Sq Ft
- Built 1902
262 Hidden Valley Rd, West Rupert, VT 05776

Last Sold Summary
- 69% Above List Price
- $88/SF
- 65 Days On Market
Last Sold Price $220,000

Last Listing Agent Scott McChesney Lee D McChesney Real Estate

/22
Est $668,613 Not Listed For Sale

14 Sykes Hollow Rd, Pawlet, VT 05761
- 3 Beds
- 2 Baths
- 1,845 Sq Ft
- Built 1790
14 Sykes Hollow Rd, Pawlet, VT 05761

Last Sold Summary
- 52% Above List Price
- $238/SF
- 131 Days On Market
Last Sold Price $440,000

Last Listing Agent David Halligan Four Seasons Sotheby's Int'l Realty

/37
Not Listed For Sale

2438 Vt Route 30, Pawlet, VT 05761
- 4 Beds
- 1 Bath
- 1,986 Sq Ft
- Built 1850
2438 Vt Route 30, Pawlet, VT 05761

Last Sold Summary
- $101/SF
- 236 Days On Market
Last Sold Price $200,000

Last Listing Agent Rebecca Cramer Cramer Realty, PLC

/5
Not Listed For Sale

0 Ebenville Rd Unit 4242946, Dorset, VT 05251
0 Ebenville Rd Unit 4242946, Dorset, VT 05251

Last Sold Summary
- 1,352 Days On Market
Last Sold Price $16,500

Last Listing Agent Scott McChesney McChesney RE, Inc.

/7
Not Listed For Sale

0 Suncrest Rd Unit 4431366, Rupert, VT 05768
0 Suncrest Rd Unit 4431366, Rupert, VT 05768

Last Sold Summary
- 58 Days On Market
Last Sold Price $287,500

Last Listing Agent David Shehadi Josiah Allen Real Estate, Inc.

/3
Not Listed For Sale

tbd Sandgate Rd, Rupert, VT 05776
tbd Sandgate Rd, Rupert, VT 05776

Last Sold Summary
- 232 Days On Market
Last Sold Price $26,250

Last Listing Agent Josh Wien Northshire Realty

/6
Not Listed For Sale

1566 Vt Rte 315, Rupert, VT 05768
1566 Vt Rte 315, Rupert, VT 05768

Last Sold Summary
- 324 Days On Market
Last Sold Price $109,500

Last Listing Agent Scott McChesney McChesney RE, Inc.

/36
Est $404,107 Not Listed For Sale

1035 Sandgate Rd, West Rupert, VT 05776
- 3 Beds
- 2 Baths
- 1,716 Sq Ft
- Built 1970
1035 Sandgate Rd, West Rupert, VT 05776

Last Sold Summary
- 103% Above List Price
- $116/SF
- 10 Days On Market
Last Sold Price $199,000

Last Listing Agent Scott McChesney McChesney RE, Inc.

/7
Not Listed For Sale

0 Ike Wright Rd Unit 4627119, Rupert, VT 05776
0 Ike Wright Rd Unit 4627119, Rupert, VT 05776

Last Sold Summary
- 13 Days On Market
Last Sold Price $100,000

Last Listing Agent Scott McChesney McChesney RE, Inc.

/31
Not Listed For Sale

5688 Route 315, Rupert, VT 05768
- 4 Beds
- 2.5 Baths
- 2,900 Sq Ft
- Built 1860
5688 Route 315, Rupert, VT 05768

Last Sold Summary
- $103/SF
- 3 Days On Market
Last Sold Price $299,000

Last Listing Agent Dan Mason Perrott Realty

Showing Results 41 - 80, Page 2 of 15

Vermont Bennington County Rupert

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Copyright 2026 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.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage