Listed by David Shehadi • Josiah Allen Real Estate, Inc. Bought with Josiah Allen Real Estate, Inc.
Off Market Nov 2022 for $890K
$1,374,504
5
bd
•
4 ba
•
3,700
sq ft
4145 Route 153, Rupert, VT 05768
About this home
Historic Farmhouse located on 100+ acres in beautiful Rupert, VT! Built around 1850 or before, this home has 5 bedrooms / 4 baths, a beautifully renovated kitchen and a bright airy sunroom that looks towards the mountains. Sensational mountain views throughout the property. Originally settled by Revolutionary Veteran in 1780; known by recent generations as the C. I. Sheldon Farm, its barn was once the most "modern" in Rupert. Along with the larger barn and silo, there is a 3 car detached garage/barn with stalls and room for storage. The rail trail runs through the property which is great for walking, running or biking! There is a pond near the house and beaver ponds out by the headwaters of the Indian river next to the rail trail. There are other trails that adventure through the acres that can be used for many different activities! Equine friendly. Hunters paradise. Subdividable. Whole house generator. High end upgrades throughout. Well insulated. 5 fireplaces housing 2 beautiful VT wood stoves and 2 Regency remote/thermostat controlled high efficiency inserts. . 15 minutes to the villages of Pawlet and Dorset , 20 minutes to Manchester. Great opportunity. School Choice. Come take a look!
Single-familyProperty Type
1850Year Built
100.92 acresLot Size
$371Est. Price/Sq.Ft.
3 car garageParking
Listed by David Shehadi• Josiah Allen Real Estate, Inc.
Bought with David Shehadi• Josiah Allen Real Estate, Inc.
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Earn from this home
Rent
$2,658/mo
Redfin rental estimate
List your home for rent
Market trends in 05776, VT
Last updated August 2026
Sale-to-List Price
102.5%
+2.4% MoM
Median sale price
$405K
$127K MoM
Avg. days on market
10d
36 days MoM
Recently sold homes
1
1 MoM
Provided by Redfin
Sale history for 4145 Route 153
Date
Event
Price
PrimeMLS #4929900
Nov 14, 2022
Sold
$890,000
$241/sq ft
Oct 5, 2022
Contingent
—
Sep 15, 2022
Listed
$995,000
$269/sq ft
As the MLS and public records start to fill up, we'll list the details here.
Public record
Public record
Zoning
Beds
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Baths
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Stories
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Lot width
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Lot depth
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Lot size
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Year renovated
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Sq. Ft.
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Year built
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Style
Single Family Residential
County
Bennington County
APN
537-169-10148
Parking Spaces
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Basement
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Accessible
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HOA Dues
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Garage
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Features
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Last updated by owner on Jun 8, 2023.
RM
Resource Management District
The purpose of this district is to implement the goals and policies of the Rupert Town Plan . Specifically the town plan calls for these regulations to: Allow for resource-based industries in appropriate locations – to include an adequate land base for farming and forestry, needed support services and value-added production; Support the efficient use of land; Allow home-based businesses in suitable rural locations; Incorporate standards that minimize the fragmentation of important agricultural land and forested wildlife habitat; and Require the designation of development envelopes on proposed subdivision plats, along with maximum area and siting requirements, to ensure that new development will be located to avoid adverse impacts to important natural and scenic resources and environmentally sensitive areas.
Permitted uses
Include but are not limited to:
Agriculture
Housing-Group
Housing-Single unit
Housing-Multiple units
Mixed use
Timberland
Property details
Parking
Parking & Garage
Garage Capacity: 3
Location: Detached
Auto Open, Barn
Interior
Virtual Tour
Bathroom Information
# of Baths (full): 2
# of Baths (3/4): 2
Basement Information
Basement: Yes
Basement Access: Interior
Interior Access, Stairs - Basement
Other Interior Features
# of Rooms: 10
Flooring: Tile, Wood
Water Heater: Owned
Attic, Ceiling Fan, Fireplace - Gas, Hot Tub, Kitchen Island, Natural Light, Walk-in Closet, Laundry - 1st Floor
Equipment & Appliance Information
Dishwasher, Dryer, Exhaust Hood, Refrigerator, Washer, Stove - Gas