494-564 Goodaleville Road

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Active
$2,430,000
9 beds4,996 sqft
494-564 Goodaleville Rd, Jamaica, VT 05343
Est: $14,562/moGet pre-approved
Single FamilyProperty Type
13.66 acresLot Size
1860Year Built
$486/sq ftPrice per sq ft
1 carParking Spaces

Description

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, a restored vintage barn, and more than 13 acres along the Winhall River. Thoughtfully renovated by Vermont Country Builders, Winhall River Farm 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...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, a restored vintage barn, and more than 13 acres along the Winhall River. Thoughtfully renovated by Vermont Country Builders, Winhall River Farm 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, a 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 & #5101689. Seller is the listing broker.
30 days on Market
  • Listed by: Cheyanne Pugliese • The Haven Group
Last updated: 09/06/2026 01:37 PM • Source: New England Real Estate Network, MLS#: 5107418

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Location

Listing Courtesy of The Haven Group
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$14,562 per month

30 year fixed, 7.03% Interest

Principal and Interest

$12,973

Property Taxes

$1,590

HOA Dues

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Property Information for 494-564 Goodaleville Road

Property Details
  • Taxes: $19,076 / year
  • MLS Type: Residential / Single Family
  • County: Windham County
  • Water Body Type: Stream
  • Water View: Yes
  • Waterfront Property: Yes
  • Zoning: None
Building Information
  • Stories: 3
  • Year Built: 1860
  • Lot Size: 13.66 AC / 595,029 SF
Summary
Location and General Information
  • City: Jamaica
  • County: VT-Windham
  • Directions: From Honeypie at the intersection of Route 30 and Route 100, head south on Route 100 for approximately 0.2 miles. Turn left onto Goodaleville Road. Continue for approximately 0.5 miles. 494-498 Goodaleville Road is the white farmhouse with two barns and 564 is the white house in field.
  • Latitude: 43.152581310673391
  • Longitude: -72.834793457221991
  • Road Frontage: TBD
  • Seasonal: No
  • State: VT
  • Street Designation: Road
  • Zip Code: 05343
Taxes and HOA Information
  • SPAN Number: 324-101-11170
  • Tax Year: 2026
  • Taxes TBD: Yes
Parking
  • Garage: Yes
  • Garage Capacity: 1.00
  • Driveway: Gravel
Property
Lot Information
  • Lot Features: Country Setting, Landscaped, Ski Area, Trail/Near Trail, Walking Trails, Near Paths, Near Skiing, Rural
  • Lot Size Acres: 13.66
  • Water Body Access: Yes
  • Water Body Name: Winhall River
  • Waterfront Property Rights: Exclusively Owned
  • Total Finished Area: 4996.0
  • Above Grade Finished Area: 3947.0
  • Above Grade Finished Area Source: Other
  • Above Grade Unfinished Area: 0.0
  • AboveGradeUnfinishedAreaSource: Other
  • Below Grade Finished Area: 1049.0
  • Below Grade Finished Area Source: Other
  • Below Grade Unfinished Area: 0.0
  • BelowGradeUnfinishedAreaSource: Other
  • Lot Size Square Feet: 595030.0
  • Total Area: 4996.0
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Property Condition: Existing
  • Flood Zone: Land Only
  • PreConstruction: No
  • Surveyed: Yes
  • Water Body Restrictions: Unknown
  • Year Built: 1860
Utilities
  • Electric: Circuit Breaker(s)
  • Sewer: Septic
  • Water Source: Drilled Well
  • Utilities: Cable Available
  • Water Access Details: Other
  • Internet: High Speed Intrnt Avail
Interior and Exterior Features
Exterior Features
  • Color: White
  • Construction Materials: Post and Beam
  • Roof: Standing Seam
Interior Features
  • Appliances: Dishwasher, Dryer, Microwave, Electric Range, Refrigerator, Washer, Gas Stove, Induction Cooktop
  • Basement: Yes
  • Basement Access Type: Interior
  • Basement Description: Finished
  • Flooring: Carpet, Tile, Wood
  • Heating: Propane, Baseboard, Radiant, Radiant Floor, Mini Split, Boiler
  • Cooling: Mini Split
  • Total Stories: 3
  • Rooms Total: 19
  • Bathrooms Full: 4
  • Bathrooms Half: 0
  • Bathrooms One Quarter: 0
  • Bathrooms Three Quarter: 3
  • Bedrooms Total: 9
  • Bathrooms Total: 7

Property History for 494-564 Goodaleville Road

DateEvent & SourcePriceAppreciation
Aug 30, 2026

Listed (Active)

New England Real Estate Network #5107418

$2,700,000—
DateEvent & SourcePrice
08/30/2026

Listed (Active)

New England Real Estate Network #5107418

$2,700,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Schools near 494-564 Goodaleville Road

This home is within West River Valley Modified Union Education District #72a.
Rating
School
Type
Grades
Distance
Leland & Gray Uhsd #34
Public - 6 to 12
Rating
School
Distance
Leland & Gray Uhsd #34
Public6 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 494-564 Goodaleville Road, Jamaica, VT 05343

494-564 Goodaleville Road is a single family home for sale in Jamaica, VT 05343. This property was listed for sale on August 30, 2026 by The Haven Group, it's currently listed at $2,430,000. This listing's school districts are West River Valley Modified Union Education District #72a, West River Valley Modified Union Education District #72b. Nearby schools include Leland & Gray Uhsd #34. 494-564 Goodaleville Road is a 9-bed, 7-bath, 4,996 sqft single family home built in 1860.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of The Haven Group

Copyright 2026 PrimeMLS, Inc. 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. Data last updated 09/29/2026 10:29 PM