New Listing
In-Person: 09/05 3:00 PM - 5:00 PM
494-564 Goodaleville Road,Jamaica, VT 05343
Jamaica, VT 05343
Description
10 MINUTES TO STRATTON RESORT | TWO HOMES | 1BR BARN APARTMENT | RESTORED VINTAGE BARN | 13+ ACRES. A rare Vermont multi-residence estate offering two beautifully renovated homes, a separate 1BR barn apartment, restored vintage barn, and more than 13 acres along the Winhall River. Thoughtfully renovated by Vermont Country Builders, the property blends authentic character, exceptional craftsmanship, and modern four-season comfort. One residence is a restored 4BR farmhouse once used as the summer home of renowned art historian Meyer Schapiro, with wide-plank floors, antique doors, an expanded kitchen with soapstone counters, updated baths, and custom built-ins. Schapiro's former art studio now serves as a self-contained 1BR apartment with SMEG appliances, screened porch, and heated storage below. The second home is a reimagined historic schoolhouse with a timber-frame addition, high ceilings, generous windows, two sunrooms, restored floors, and warm architectural detail throughout. Private hot tubs and inviting outdoor living spaces complement all three residences. Extensive improvements across the property include standing-seam roofs, new Marvin windows, updated electrical and plumbing, modern insulation, mini-split heating and cooling, high-efficiency systems, new appliances, generators, and EV chargers. The 13+ acres include open fields, woods, apple trees, gardens, extensive stonework, patios, decks, and opportunities for trails, recreation, and equestrian use. Set along the Winhall River with direct access to the West River Rail Trail for walking, biking, swimming, and exploring. In the heart of ski country, just minutes from Stratton, Bromley, and Magic Mountain. An exceptional family estate, multi-generational retreat, or investment opportunity. Offered furnished and ready to enjoy, with additional acreage also available. All the hard work has been done--move in and start enjoying Vermont. Properties also offered individually as MLS #5101688 and #5101689.
Details
| MLS # | 5107418 |
|---|---|
| Listing Type | For Sale |
| Style | House |
| Sub-Type | Resale |
| Status | (10) Active - Active |
| Year | 1860 |
| Days On Site | 1 |
| Listing Provided By | The Haven Group | Cheyanne Pugliese |
Features
| Bed(s) | 9 |
|---|---|
| Bath(s) | 7 Total |
| Garage | 1 |
| Basement | Y |
| Story(s) | 3 |
| Zoning | None |
| Acreage | 13.66 |
| Water Front | Yes |
Interior
| Rooms Total | 19 |
|---|---|
| Cooling | Mini Split |
| Heating | Propane, Baseboard, Radiant, Radiant Floor, Mini Split, Boiler |
| Interior Features | Gas Fireplace, 1 Fireplace, Hot Tub, In-Law/ADU, Primary BR w/ BA |
| Appliances | Dishwasher, Dryer, Microwave, Electric Range, Refrigerator, Washer, Gas Stove, Induction Cooktop |
Exterior
| Exterior Features | Barn, Guest House, Hot Tub, Patio, Covered Porch, Screened Porch, Storage |
|---|---|
| Roof | Standing Seam |
| Construction Materials | Post and Beam |
| Foundation Details | Concrete |
| Lot Features | Country Setting, Landscaped, Ski Area, Trail/Near Trail, Walking Trails, Near Paths, Near Skiing, Rural |
Parking
| Garage Yes / No | Yes |
|---|
Utilities
| Utilities | Cable Available |
|---|---|
| Electric | Circuit Breakers |
| Sewer | Septic Tank |
Taxes
| Tax Annual Amount | 19076 |
|---|---|
| Tax Year | 2026 |
Area Information
| State | VT |
|---|---|
| County | Windham |
| City | Jamaica |
| Zip Code | 05343 |
| Area | VT Windham |
| Listing VS Median (in 05343) | |
Price: $2,700,000 low | high Med: $2,399,000 On site: 1 low | high Med: 1066 | |
Market Activity 05343
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Copyright 2026 PrimeMLS. 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.
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Learn More About This Property
| Open House |
|---|
| In-Person 09/05 3:00 PM - 5:00 PM |
| State | VT |
|---|---|
| County | Windham |
| City | Jamaica |
| Zip Code | 05343 |
| Area | VT Windham |
| Listing VS Median (in 05343) | |
Price: $2,700,000 low | high Med: $2,399,000 On site: 1 low | high Med: 1066 | |
 | $1,450,000494-498 Goodaleville RoadJamaica, VT 05343 |
 | $1,250,000564 Goodaleville RoadJamaica, VT 05343 |
Copyright 2026 PrimeMLS. 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.
