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23 Homes For Sale in Rupert, VT

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house for sale
3 bds | 3 ba | 1,800 sqft

57 Ike Wright Road Trail, Rupert, VT 05768

Built in 2005 with large addition added in 2017 this home in the country is picturesque! This 162 acre property features...
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$495,000
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house for sale
4 bds | 4 ba | 3,350 sqft

318 Antone Mountain View, Rupert, VT 05768

Incredible mountain views, total privacy on 10 acres off a dead-end private road, and a great Rupert location just 5 mil...
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$389,000
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house for sale
4 bds | 3 ba | 2,988 sqft

369 Sykes Hollow Rd, Rupert, VT 05761

This is the quintessential Vermont horse property located minutes from the Dorset green. The farm has it all: 33 acres o...
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$2,400,000
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house for sale
2 bds | 2 ba | 1,445 sqft

119 Watrous Rd, Rupert, VT 05776

This classic log home equally well suited as an idyllic vacation retreat or a comfortable year round residence! The prop...
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$267,800
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Lots/Land for sale
122.12 acres

5251 Suncrest Road, Rupert, VT 05768

Extraordinary122 acre +/- land parcel with views, pastures, hayfields, stream, woodlands and multiple house sites with s...
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$299,000
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house for sale
-- bds | 2 ba | 3,584 sqft

115 Main Street, Rupert, VT 05776

Amazing opportunity! Commercially zoned Antique Center formally the J.H. Gould Company, this has serious potential. Live...
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$235,000
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house for sale
5 bds | 6 ba | 4,950 sqft

926 Hebron Road, Rupert, VT 05768

Within 15 minutes of Dorset, Stone Ridge Farm offers complete privacy and commanding views of the Taconic Mountains. The...
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$995,000
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Lots/Land for sale
26 acres

0 Kent Hollow Rd, Rupert, VT 05776

Set privately in the hills of West Rupert is this special +/-26 acre parcel with gorgeous mountain views and nice open m...
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$49,000
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$30,000
house for sale
3 bds | 2 ba | 1,845 sqft

14 Sykes Hollow Rd, Rupert, VT 05768

A Small Slice of Heaven. This property offers the best of both worlds; the style & charm of a vintage 1790's Vermont Far...
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$535,000
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house for sale
3 bds | 2 ba | 1,650 sqft

363 Ebenville, Rupert, VT 05776

Charming restored antique cape home with five fireplaces. Lovely stone patio that overlooks the pond. Nice eat in kitche...
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$395,000
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$55,000
house for sale
7 bds | 9 ba | 5,541 sqft

195 Derby Hill Road, Rupert, VT 05768

A truly special property with loads of room including the 3700 square foot main house with 5 bedrooms, 1800 square foot ...
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$640,000
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$60,000
house for sale
3 bds | 4 ba | 3,033 sqft

251 Youlin Rd, Rupert, VT 05776

Total privacy set back amidst 60 acres of woods and gorgeous rolling meadowland is this 3+ bedroom, 3.5 bath beautifully...
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$399,000
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$10,000
house for sale
5 bds | 2 ba | 2,430 sqft

2826 Pawlet Mountain Rd, Rupert, VT 05768

Set privately back off a town gravel road on a beautiful +/-5 acre parcel- rolling meadowland and a manicured yard is th...
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$239,900
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$23,500
house for sale
2 bds | 2 ba | 1,700 sqft

4035 Kent Hollow, Rupert, VT 05776

Tucked back off of a town gravel road in the hills of Rupert is this special property offering total privacy and views. ...
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$274,500
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house for sale
4 bds | 4 ba | -- sqft

321 Rogers, Rupert, VT 05251

Seller is now saying BRING ME AN OFFER! Located exactly 2.5 miles from the DORSET INN, DORSET GREEN & THE DORSET UNION S...
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$645,000
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$294,000
house for sale
3 bds | 3 ba | 3,300 sqft

334 Dole Road, Rupert, VT 05776

Mountain View Farm is a horseman's paradise. Panoramic far reaching views. Center chimney reproduction saltbox home with...
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$1,295,000
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$9,000
house for sale
3 bds | 3 ba | 2,346 sqft

4451 Route 315, Rupert, VT 05768

Spacious 3 bedroom, 2.5 bath colonial on 28 private acres of meadows and woods is only 3.5 miles to the Dorset Village G...
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$290,000
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