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Jessica Samples
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957 Pleasant Valley Road, Benson, VT 05743

$2,249,000
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Active
BEDS12 BATHS5 full 1 partial SQUARE FEET6,491 MLS#5098593
STATUSActive PROPERTY TYPEResidential - Single Family SCHOOLBenson

Listing Courtesy of: Four Seasons Sothebys Intl Realty
Agency Phone: 802-864-0541
Associate Name: Alex Pintair
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Property Description

A once-in-a-lifetime opportunity to own an extraordinary 460-acre estate where timeless character, modern functionality, and breathtaking natural beauty converge. Nestled within a pristine valley of rolling pastures, mature forests, and pastoral views, this remarkable property offers limitless possibilities from a thriving agricultural enterprise to an unparalleled private family retreat. At the heart of the farm are two exceptional residences. The charming vintage farmhouse features four bedrooms and four baths, blending historic warmth with classic VT living. Complementing it is an elegant estate home with five bedrooms and four baths, providing refined accommodations ideal for extended family, guests, or multi-generational living. A separate guest cottage adds even more flexibility for visitors, caretakers, or rental opportunities. Designed for serious agricultural production while offering exceptional lifestyle appeal, the property includes a dairy barn, equipment barn, hay barn, workshop, bunkhouse, fuel depot and more. Nine electrified beef cattle paddocks create an efficient rotational grazing system, while an extensive solar array powers the operation, enhancing sustainability and reducing operating costs. The land itself is simply extraordinary. Expansive open fields transition seamlessly into peaceful woodlands, creating a landscape equally suited for livestock, equestrian pursuits, recreation, hunting, hiking, conservation, or simply enjoying the serenity of country living. Whether your vision is a productive working farm, an equestrian estate, a self-sufficient gentleman's farm, a luxury family compound, a corporate retreat, or a legacy property to be cherished for generations, this exceptional offering provides the foundation to make it a reality. Rarely does a property of this scale, quality, and versatility become available. More than a farm, this is an opportunity to create a lasting legacy limited only by your imagination.

957 Pleasant Valley Road | MLS# 5098593

This single family home located at 957 Pleasant Valley Road, Benson, VT 05743 is currently listed for sale with an asking price of $2,249,000. This property was built in 1887 and has 12 bedrooms and 5 full and 1 partial baths with 6491 sq. ft. Pleasant Valley Road is located within the Benson school district. Search Benson real estate on jessicasamples.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Concrete, Storage Space, Sump Pump, Unfinished, Walkout, Exterior Access
Cooling: Wall AC Units, Mini Split
Garage: 2
Heating: Oil, Baseboard,2 Stoves, Wood Stove, Wood Boiler
Home Style: Farmhouse
Lot Size: 461.00 Acres
Roof Type: Metal, Asphalt Shingle, Slate
Stories: 2.5
Taxes: $27,000
Year Built: 1887

Amenities

Cathedral Ceiling
Ceiling Fan
Dining Area
Gas Fireplace
Wood Fireplace
In-Law/ADU
In-Law Suite
Kitchen Island
Kitchen/Dining
Kitchen/Living
Primary BR w/ BA
Natural Light
Natural Woodwork
Skylight
Soaking Tub
Indoor Storage
Vaulted Ceiling
Walk-in Closet
1st Floor Laundry
2nd Floor Laundry
Barn
Building
Deck
Guest House
Outbuilding
Covered Porch
Shed
Storage
Double Pane Window(s)
Stable(s)
Poultry Coop

Feature Descriptions

Appliances: Gas Cooktop, Dishwasher, Disposal, Dryer, Freezer, Microwave, Electric Range, Gas Range, Refrigerator, Washer, Exhaust Fan, Vented Exhaust Fan
Baths 1/2: 1
Baths Full: 5
Color: gray
Construction: Wood Frame, Vinyl Siding, Wood Exterior, Wood Siding
Construction Status: Existing
Days on Site: 15
Driveway: Gravel
Electric: 200+ Amp Service, Circuit Breaker(s), Generator, On-Site
Equipment: Smoke Detector, Hardwired Smoke Detector, Wood Stove, Standby Generator
Exterior: Wood Frame, Vinyl Siding, Wood Exterior, Wood Siding
Flood Zone: No
Flooring: Laminate, Marble, Slate/Stone, Tile, Wood
Foundation: Concrete, Fieldstone, Concrete Slab
Lot: Alternative Lots Avail, Conserved Land, Country Setting, Farm, Dairy Farm, Horse/Animal Farm, Field/Pasture, Pond, Rolling, Secluded, Wooded, Abuts Conservation, Rural
Number of Rooms: 20
Parking: Driveway, Garage, On-Site, Parking Spaces 1 - 10, Unpaved, Barn
Road Frontage: 1330
Roads: Gravel, Public Maintained Road
Sewer: Septic
Sq. Ft. Above Grade Finished: 6491
Sq. Ft. Total Finished: 6491
Total Stories: 2.5
Units: 1
Water: Drilled Well
Zoning: agricultural

Local Schools

High School: Assigned
Middle School: Assigned
Elementary School: Benson Village School
School District: Benson

Listed By / Shown By

Listed By

Agency Name: Four Seasons Sothebys Intl Realty
Agent Name: Alex Pintair
Agency Phone: 802-864-0541

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

$ 7,911.26 per month $5,005.30 Principal & Interest $2,250.00 Property Tax $655.96 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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