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Jessica Samples
REALTOR®
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253 Perkins Road, Rupert, VT 05776

$430,000
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Active
BEDS4 BATHS2 full SQUARE FEET2,768 MLS#5098562
STATUSActive PROPERTY TYPEResidential - Single Family SCHOOLBennington-Rutland

Listing Courtesy of: Four Seasons Sothebys Intl Realty
Agency Phone: 802-362-4551
Associate Name: Derryl Lang
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Property Description

Tucked away on a quiet, town-maintained dead-end dirt road, this inviting Rupert, Vermont property offers the kind of peaceful country setting that's becoming increasingly hard to find. Set on 6.79 acres, it's a place where morning walks, afternoon bike rides, and evenings under the stars can become part of everyday life. At the heart of the property is a circa 1850 Greek Revival home, rich with architectural character and topped by a classic slate roof. A substantial steel barn offers exceptional space for hobbies, equipment, vehicles, a workshop, or the projects you've always wanted room to pursue. Significant improvements have already been completed, including a new septic system, ductless mini-split heating and cooling, all new windows and exterior doors, a whole-house water filtration and softener system, an updated bathroom and a generator hookup. These investments provide a solid foundation while leaving room for the next owner to add their own vision. Offered as-is and priced accordingly, the home presents an opportunity to complete additional improvements and finishing work while creating a property that reflects your own style and needs. Conveniently located just 20 minutes from Dorset, 30 minutes from Manchester, and about an hour from Rutland, Bennington, and Saratoga Springs, you'll enjoy the tranquility of country living with easy access to shopping, dining, recreation, and cultural attractions. If you're looking for a Vermont property with authentic character, open space, and the opportunity to make it your own, schedule your private showing today and experience all this special property has to offer. Interior photos will be forthcoming.

253 Perkins Road | MLS# 5098562

This single family home located at 253 Perkins Road, Rupert, VT 05776 is currently listed for sale with an asking price of $430,000. This property was built in 1850 and has 4 bedrooms and 2 full baths with 2768 sq. ft. Perkins Road is located within the Bennington-Rutland school district. Search Rupert real estate on jessicasamples.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Bulkhead, Full, Gravel, Unfinished, Interior Access
Basement: Yes
Cooling: Multi Zone, Mini Split
Garage: 2
Heating: Oil, Heat Pump, Mini Split, Boiler
Home Style: Greek Revival
Lot Size: 6.79 Acres
Roof Type: Metal, Slate
Stories: 2.0
Taxes: $5,636
Year Built: 1850

Amenities

Garden Space
Outbuilding
Enclosed Porch
Double Pane Window(s)

Feature Descriptions

Baths 3/4: 1
Baths Full: 1
Color: White
Construction: Steel Frame, Wood Frame, Clapboard Exterior, Metal Clad Exterior
Construction Status: Existing
Days on Site: 14
Driveway: Paved
Electric: Circuit Breaker(s)
Exterior: Steel Frame, Wood Frame, Clapboard Exterior, Metal Cl
Flood Zone: No
Foundation: Stone
Lot: Agricultural, Country Setting, Farm, Field/Pasture, Open, Secluded, Stream, Trail/Near Trail, Wooded, Near Paths, Rural, Private
Number of Rooms: 8
Road Frontage: 380
Roads: Dead End, Gravel, Unpaved, Public Maintained Road
Sewer: 1000 Gallon, Concrete, Leach Field, Septic
Sq. Ft. Above Grade Finished: 2768
Sq. Ft. Total Finished: 2768
Total Stories: 2
Water: Drilled Well, Purifier/Soft, Reverse Osmosis, Ultravi
Zoning: Rural Residential

Room Sizes

Living Room: 12.-6x24.-6 Level - 1
Den: 13.-9x13.-2 Level - 1
Bedroom: 10.-6x11 Level - 1
Eat-in Kitchen: 27.-4x16.-5 Level - 1
Bedroom: 12.-6x15.4 Level - 2
Office/Study: 10.-11x8.-10 Level - 2
Bedroom: 13.-9x9.-11 Level - 2
Bedroom: 11.-4x11 Level - 2

Local Schools

High School: Choice
Middle School: Choice
Elementary School: Mettawee Community School
School District: Bennington-Rutland

Listed By / Shown By

Listed By

Agency Name: Four Seasons Sothebys Intl Realty
Agent Name: Derryl Lang
Agency Phone: 802-362-4551

agent picture

Shown By

Agent Name: Jessica Samples
Agent Phone:
Agency Title: Better Homes and Gardens Real Estate The Masiello Group

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Estimated Payment

$ 1,552.08 per month $956.99 Principal & Interest $469.67 Property Tax $125.42 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 07/22/2026. The listing information on this page last changed on 07/22/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 07/22/2026 12:00:31 AM EST) or MLSPIN MLS (last updated Tue 07/21/2026 11:38:24 PM EST) or Prime MLS (last updated Tue 07/21/2026 11:33:17 PM EST) or MREIS (last updated Tue 07/21/2026 11:55:21 PM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

Listing data compilation and photo(s) 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. Data Last Updated 2026-07-21 23:33:17

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