494-564 Goodaleville Road Jamaica, VT $ 2,430,000
494-564 Goodaleville Road
$ 2,430,000
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494-564 Goodaleville Road

Jamaica, VT, 05343
$ 2,430,000
Bedrooms9 Baths7.0 Sq 4,996

Monthly Estimate*

$ 15,343

Listed by Cheyanne Pugliese, The Haven Group, 802-548-6320, cheyanne@thehavenvt.com
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Single Family Home for sale in Jamaica, VT

for $2,430,000 with 9 bedrooms and 7 full baths. This 4,996 square foot home was built in 1860 on a lot size of 13.66.

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.

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Single Family Active

Price

$ 2,430,000

Bedrooms

9

Full Bath

7

Property Type

Single Family

Taxes

$ 0

Style

Contemporary,Farmhouse

Lot Size

13.66

Year Built

1860

Town/City

Jamaica

County/Region

Windham

MLS | Web ID

5107418

Features
Interior
Basement Description Finished
Interior Amenities Gas Fireplace 1 Fireplace Hot Tub In-Law/ADU Primary BR w/ BA
Basement Yes
Flooring Carpet Tile Wood
Beds 9
Total Rooms 19
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General
Road Frontage TBD
Sewer Septic
Heating Propane Baseboard Radiant Radiant Floor Mini Split Boiler
Cooling Mini Split
Utilities Cable Available
Roof Standing Seam
Appliances Dishwasher Dryer Microwave Electric Range Refrigerator Washer Gas Stove Induction Cooktop
Garage Yes
Flood Zone Land Only
Zoning None
3/4 Baths 3
Full Baths 4
Half Baths 0
Bathrooms 7
Year Built 1860
Electric Circuit Breaker(s)
Style Contemporary Farmhouse
Stories Count 3
Type Single Family
Property Condition Existing
Tax Year 2026
Status Detail 0
Covenants No
Construction Materials Post and Beam
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 Goodal
City Jamaica
Other Equipment Air Conditioner Dehumidifier Whole BldgVentilation Standby Generator
Seasonal No
DOM 7
Price Per Sq Ft Total AG 615.66
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Exterior
Lot Features Country Setting Landscaped Ski Area Trail/Near Trail Walking Trails Near Paths Near Skiing Rural
Exterior Amenities Barn Guest House Hot Tub Patio Covered Porch Screened Porch Storage
Driveway Gravel
Water View Yes
Lot Size Area 13.66
Water Source Drilled Well
Garage Capacity 1
Water Body Name Winhall River
Foundation Concrete
Waterfront Property Yes
Water Body Type Stream
Water Body Access Yes
Water Access Details Other
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* Excluded Features
List By
Cheyanne Pugliese

Listing Agent

The Haven Group

Broker

(802) 548-6320

Phone

cheyanne@thehavenvt.com

Email

Affordability Calculator

$15,343
Per Month
100%
0%
0%
Monthly Principal & Interest
$15,343
Monthly Property Taxes
--
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
451920 Elementary School
452237 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
9/6/2026$2,430,000 -10.00% Price Down
8/31/2026$2,700,000 Listed Price

Map


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494-564 Goodaleville Road, Jamaica, VT, 05343 is a Single Family Home for sale at $2,430,000 with 4,996 sqft and a lot size of 13.66. 494-564 Goodaleville Road has 9 bedrooms, 7.0 baths, and was built in 1860. The property's zip code is 05343 which is in Jamaica, VT