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Offered at $745,000Active Under Contract
beds
3
baths
2
sq ft
2,034
Built
1825

2238 Upper Michigan Road

Pittsfield, VT 05762

Residential · Active Under Contract · MLS #5097001
Listing Courtesy of Killington Pico Realty | Kyle Kershner

The home

About this home

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.

Property information

Details at a glance

Interior4 property facts
Rooms
6
Heating
Baseboard, Hot Water, Wood, Wood Stove
Cooling
None
Flooring
Carpet, Vinyl, Combination, Softwood
Building6 property facts
Style
Single Family Residence
Year built
1825
Garage
2
Parking
2
Foundation
Stone
Roof
Shingle
Land & utilities4 property facts
Lot size
54.4 acres
Water
Well, Private
Sewer
Septic Tank
Zoning
None
Financial2 property facts
Annual taxes
$6,310
Assessment year
2025

Plan your purchase

Estimated monthly cost

Explore costs at the $745,000 asking price. Adjust the assumptions to your situation.

Known monthly costs$4,293 / monthAdjust
Principal & interest
$3,767
Property tax
$526
Insurance
Not entered
HOA
Not entered

Listing annual taxes: $6,310. Initial monthly tax is one twelfth of that amount. HOA amount was not supplied.

Partial estimate: add insurance, monthly HOA to include those costs. Blank amounts are unknown.

The initial 6.5% rate is illustrative, not a current rate or lender quote. Excludes utilities, maintenance, closing costs and mortgage insurance, which may apply with a down payment below 20%. Taxes and insurance can change.

Listing history

Price and status timeline

No additional listing history is available for public display.

Compare with confidence

Price & market context

See how this home compares with active listings in Pittsfield.

This home compared with active listings in Pittsfield
MetricThis homeLocal listings
List price$745,000$617,45021% above local
Price / sq ft$366$30919% above local
Days on market54288% below local

Active city listing statistics from PrimeMLS as of September 11, 2026. Asking prices are not completed-sale values.

Keep exploring

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Common questions

About 2238 Upper Michigan Road

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Request a tour of 2238 Upper Michigan Road and a Bean Group agent will help coordinate an available time with the listing side.

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Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.

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