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Jessica Samples
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2238 Upper Michigan Road, Pittsfield, VT 05762

$745,000
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Active Under Contract
BEDS3 BATHS1 full 1 partial SQUARE FEET2,034 MLS#5097001
STATUSActive Under Contract PROPERTY TYPEResidential - Single Family

Listing Courtesy of: Killington Pico Realty
Agency Phone: 802-422-3600
Associate Name: Kyle Kershner
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Property Description

Tucked away at the end of Upper Michigan Road on 54.4 private acres bordering the Green Mountain National Forest, this remarkable 1825 Vermont farmhouse offers breathtaking long-range mountain views in an unforgettable setting. Rich in authentic character, the home showcases rustic knotty pine walls, exposed hand-hewn beams, wide plank floors, and a fieldstone fireplace hearth. The home's low ceilings and gently uneven floors are not imperfections ? they are reminders of a time when homes were built by hand and meant to last. A thoughtfully designed addition in 1996 blends seamlessly with the original home, providing modern comfort with a spacious primary bedroom featuring 10-foot ceilings and custom built-ins, a guest bedroom, and a beautifully updated full bath. The expansive living area offers inviting spaces to gather around the woodstove, enjoy movie nights, or relax with family and friends. The vintage-inspired kitchen and dining area, with vaulted ceilings, warm pine finishes, and a picnic-style dining table, is ideal for casual entertaining. Upstairs, two additional guest bedrooms and a powder room provide comfortable accommodations. Outside, more than 30 acres of managed woodland extend along both sides of the town road, complemented by open lawns, mature perennial gardens, and endless opportunities to enjoy the spectacular southern views. A detached two-car garage with overhead storage provides ample space for vehicles and outdoor gear. Snowmobiling, ATV riding, hiking, mountain biking, and snowshoeing are all accessible directly from the property. A state wastewater permit for an additional three-bedroom home offers exceptional flexibility for future expansion or a family compound. This is a rare opportunity to own a legacy Vermont property where history, privacy, recreation, and extraordinary natural beauty come together.

2238 Upper Michigan Road | MLS# 5097001

This single family home located at 2238 Upper Michigan Road, Pittsfield, VT 05762 is currently listed for sale with an asking price of $745,000. This property was built in 1825 and has 3 bedrooms and 1 full and 1 partial baths with 2034 sq. ft. Search Pittsfield real estate on jessicasamples.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Crawl Space, Dirt Floor
Cooling: None
Garage: 2
Heating: Baseboard, Hot Water, Wood Stove
Home Style: Antique, Cape, Farmhouse
Lot Size: 54.40 Acres
Roof Type: Architectural Shingle
Stories: 1.5
Taxes: $6,310
Year Built: 1825

Amenities

Dining Area
1 Fireplace
Hearth
Natural Light
Natural Woodwork
Vaulted Ceiling
Wood Stove Insert
Natural Shade

Feature Descriptions

Appliances: Dryer, Electric Range, Refrigerator, Washer
Baths 1/2: 1
Baths Full: 1
Color: Red
Construction: Wood Frame, Clapboard Exterior
Construction Status: Existing
Days on Site: 26
Driveway: Gravel
Electric: Circuit Breaker(s)
Equipment: Wood Stove
Exterior: Wood Frame, Clapboard Exterior
Flood Zone: No
Flooring: Carpet, Combination, Softwood, Vinyl
Foundation: Stone
Lot: Landscaped, Pond, View, Wooded, Adjoins St/Nat'l Forest, Near Skiing, Near Snowmobile Trails, Rural, Near ATV Trail
Number of Rooms: 6
Parking: Driveway, Garage
Road Frontage: 1410
Roads: Gravel, Public
Sewer: Private, Septic
Sq. Ft. Above Grade Finished: 2034
Sq. Ft. Total Finished: 2034
Total Stories: 1.5
Water: Drilled Well, Private

Local Schools

High School: Choice
Middle School: Choice
Elementary School: Choice

Listed By / Shown By

Listed By

Agency Name: Killington Pico Realty
Agent Name: Kyle Kershner
Agency Phone: 802-422-3600

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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

$ 2,401.17 per month $1,658.05 Principal & Interest $525.83 Property Tax $217.29 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 07/23/2026. The listing information on this page last changed on 07/23/2026. 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 Thu 07/23/2026 12:01:56 AM EST) or MLSPIN MLS (last updated Wed 07/22/2026 11:38:32 PM EST) or Prime MLS (last updated Wed 07/22/2026 11:33:29 PM EST) or MREIS (last updated Wed 07/22/2026 11:55:17 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 2026-07-22 23:33:29

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Agency License Information: Better Homes and Gardens® and the Better Homes and Gardens Real Estate Logo are registered service marks owned by Meredith Corporation and licensed to Better Homes and Gardens Real Estate LLC. The Masiello Group Limited fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each franchise is independently owned and operated. Any services or products provided by independently owned and operated franchisees are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC nor any of its affiliated companies.


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