2 Main Street

Closed 2/7/23
Closed 2/7/23
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Sold
Last Sold Price
$314,900
5 beds3,979 sqft$79/sqft
2 Main St, Rupert, VT 05776
Single FamilyProperty Type
5.03 acresLot Size
1808Year Built
$79/sq ftPrice per sq ft
1 carParking Spaces

Description

Endless possibilities and a pastoral view! Situated on 5+ acres sits this country style Colonial. Hardwood and brick inlay flooring, 3700+/- square feet, 10 rooms, 5 bedrooms, grand fireplace, 2 barns, 2 stalls, and plenty of storage. Come bring this home back to what it once was!Endless possibilities and a pastoral view! Situated on 5+ acres sits this country style Colonial. Hardwood and brick inlay flooring, 3700+/- square feet, 10 rooms, 5 bedrooms, grand fireplace, 2 barns, 2 stalls, and plenty of storage. Come bring this home back to what it once was!

    Sold By McChesney RE, Inc.

    • Listed by: Dick Thackston • R.H. Thackston & Company
    • Listed by: Emily Lagerberg • R.H. Thackston & Company/Winchester
    Listing closed: 02/07/2023 12:00 AM • Source: New England Real Estate Network, MLS#: 4939751

    Recent comparable sales

    Median sold price

    $363,000

    Avg days on market

    68

    Sale-to-list ratio

    95.8%

    Rupert, VT

    9 comparable properties found

    $355,000 | 401 18th Street, Rupert, ID 83350
    1

    $355,000

    Sold 04/03/26

    5
    Bedrooms
    3
    Bathrooms
    2,912
    Square Feet
    0.47
    Acres

    401 18th Street, Rupert, ID 83350

    $470,000 | 1717 Cedar Street, Rupert, ID 83350
    2

    $470,000

    Sold 08/18/25

    5
    Bedrooms
    3
    Bathrooms
    3,774
    Square Feet
    0.48
    Acres

    1717 Cedar Street, Rupert, ID 83350

    $295,000 | 1617 Pine Street, Rupert, ID 83350
    3

    $295,000

    Sold 09/04/25

    5
    Bedrooms
    3
    Bathrooms
    1,737
    Square Feet
    0.43
    Acres

    1617 Pine Street, Rupert, ID 83350

    $399,000 | 921 North 900 East, Rupert, ID 83350
    4

    $399,000

    Sold 09/25/25

    5
    Bedrooms
    3
    Bathrooms
    1,380
    Square Feet
    1.52
    Acres

    921 North 900 East, Rupert, ID 83350

    $385,000 | 610 19th Street, Rupert, ID 83350
    5

    $385,000

    Sold 10/23/25

    5
    Bedrooms
    3
    Bathrooms
    2,410
    Square Feet
    0.33
    Acres

    610 19th Street, Rupert, ID 83350

    $550,000 | 72 Pelican Drive, Rupert, ID 83350
    6

    $550,000

    Sold 08/18/26

    5
    Bedrooms
    3
    Bathrooms
    3,300
    Square Feet
    0.5
    Acres

    72 Pelican Drive, Rupert, ID 83350

    $225,000 | 47 Lewis Road, Rupert, VT 05775
    1/46
    7

    $225,000

    Sold 03/04/25

    4
    Bedrooms
    2,338
    Square Feet
    6.48
    Acres

    47 Lewis Road, Rupert, VT 05775

    $499,000 | 26 East 100 North, Rupert, ID 83350
    8

    $499,000

    Sold 10/21/24

    5
    Bedrooms
    3
    Bathrooms
    3,183
    Square Feet
    1.66
    Acres

    26 East 100 North, Rupert, ID 83350

    $405,000 | 130 Clark Road, Rupert, VT 05776
    1/57
    9

    $405,000

    Sold 12/17/25

    4
    Bedrooms
    2,120
    Square Feet
    2.9
    Acres

    130 Clark Road, Rupert, VT 05776

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    $2,587 per month

    30 year fixed, 6.55% Interest

    Principal and Interest

    $1,601

    Property Taxes

    $987

    HOA Dues

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    Property Information for 2 Main Street

    Property Details
    • Taxes: $11,838 / year
    • MLS Type: Residential / Single Family
    • County: Bennington County
    • Zoning: res
    Building Information
    • Stories: 2
    • Year Built: 1808
    • Lot Size: 5.03 AC / 219,106 SF
    Summary
    Location and General Information
    • City: Rupert
    • County: VT-Bennington
    • Directions: please use GPS to map directions from your current location
    • Latitude: 43.259715626654156
    • Longitude: -73.223310728836054
    • Road Frontage: TBD
    • Seasonal: No
    • State: VT
    • Street Designation: Street
    • Zip Code: 05768
    Taxes and HOA Information
    • SPAN Number: 537-169-10235
    • Tax - Gross Amount: $11,838.00
    • Tax Year: 2022
    • Taxes TBD: No
    Parking
    • Garage: Yes
    • Garage Capacity: 1.00
    • Driveway: Crushed Stone, Gravel, Other
    Property
    Lot Information
    • Lot - Sqft: 219107.0
    • Lot Size Acres: 5.03
    • Square Feet Apx Finished Above Grade: 3979.0
    • Square Feet Apx Finished AG Source: Public Records
    • Square Feet Apx Finished Below Grade: 0.0
    • Square Feet Apx Total: 3979.0
    • Square Feet Apx Total Finished: 3979.0
    • Square Feet Apx Unfinished Above Grade: 0.0
    • Square Feet Apx Unfinished Below Grade: 0.0
    Property and Assessments
    • Property Class: Residential
    • Property Type: Single Family
    • Flood Zone: No
    • Foundation: Stone
    • PreConstruction: No
    • Surveyed: No
    • Year Built: 1808
    Utilities
    • Electric: Other
    • Sewer: Private, Septic
    • Utilities: Other
    Interior and Exterior Features
    Exterior Features
    • Color: Taupe
    • Features - Exterior: Barn, Deck, Outbuilding, Porch
    • Roads: Public
    • Roof: Slate
    Interior Features
    • Basement: Yes
    • Basement Access Type: Interior
    • Basement Description: Unfinished
    • Baths - Total: 3
    • Baths - Full: 3
    • Half Baths: 0
    • One Quarter Baths: 0
    • Three Quarter Bath: 0
    • Rooms - Total: 10
    • Bedrooms - Total: 5
    • Features - Interior: Fireplace - Wood, Walk-in Pantry, Laundry - 1st Floor
    • Heat Fuel: Oil
    • Heating: Hot Air
    • Cooling: None
    • Total Stories: 2

    Property History for 2 Main Street

    DateEvent & SourcePriceAppreciation
    Feb 7, 2023

    Sold

    New England Real Estate Network #4939751

    		$314,900—
    Jan 6, 2023

    Pending

    New England Real Estate Network #4939751

    		—
    Dec 29, 2022

    Listed (Active)

    New England Real Estate Network #4939751

    		$314,900—
    DateEvent & SourcePrice
    02/07/2023

    Sold

    New England Real Estate Network #4939751

    $314,900
    01/06/2023

    Pending

    New England Real Estate Network #4939751

    —
    12/29/2022

    Listed (Active)

    New England Real Estate Network #4939751

    $314,900

    For completeness, we often displays two records for one sale: the MLS record and the public record.

    Schools near 2 Main Street

    This home is within Mettawee School District.
    Rating
    School
    Type
    Grades
    Distance
    Mettawee Community School Usd #47
    		Public - PK to 6
    Rating
    School
    Distance
    Mettawee Community School Usd #47
    PublicPK to 6

    School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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    AddressSold priceBedsBathsSqftLot (Sqft)
    This home: 2 Main Street, Rupert, VT 05776
    $314,900
    5
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    219,106
    2910 Highway 153, Rupert, VT 05768
    $206,000
    6
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    27,007
    2929 Highway 153, Rupert, VT 05776
    $429,500
    4
    4,000
    56,628
    1 Rupert Mountain Road, Pawlet, VT 05761
    –
    –
    –
    –
    41,818
    60 Vermont State Route 313, Rupert, VT 05768
    $209,000
    3
    1,860
    26,136
    2890 Highway 153, Rupert, VT 05768
    $76,000
    3
    1,990
    13,503

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    No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

    Listing Courtesy of R.H. Thackston & Company; R.H. Thackston & Company/Winchester

    Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site 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 09/07/2026 08:57 AM