WINTER SEASON RENTAL ! 4 BEDROOMS ! JAMAICA VILLAGE ! 15 MINUTES TO STRATTON $18,000 FOR 5-MONTH WINTER SEASON ! OWNER NEGOTIABLE ! Spend the winter in the heart of Southern Vermont at this charming 4-bedroom, 2-bath historic home in Jamaica Village. Offering more than 2,500 square feet of living space, the home combines classic Vermont character with comfortable, updated living spaces and plenty of room for family and guests. The spacious floor plan includes a well-appointed kitchen with center island, formal dining room, generous living room, and an expansive primary suite along with three additional bedrooms. Wood floor, original architectural details, and inviting gathering spaces give the home the warmth and character of a quintessential Vermont retreat. Ideally located in Jamaica Village, the property is approximately 15 minutes from Stratton Mountain Resort and 25 minutes from Mount Snow, making it an excellent home base for a full winter of skiing and riding. Jamaica State Park, the West River, village library, general store, and local dining are also nearby. A comfortable and convenient seasonal retreat with space to settle in, entertain, and enjoy everything Southern Vermont has to offer throughout the winter.
This property is priced $15,315 above the rental estimate.
Asking rent
$18,000
Rental estimate
$2,685
Nearby comparable rentals
The Rental Estimate uses 0 recent nearby rental.
Sale and tax history for 29 Pikes Falls Rd
Sale History
Tax History
Date
Event
Price
NEREN #5109606
Sep 14, 2026
Listed for Rent
$18,000
$10/sq ft
PrimeMLS #5078084
Jul 15, 2026
Sold
$315,000
$168/sq ft
Jun 22, 2026
Contingent
—
May 20, 2026
Price Changed
$325,000
$174/sq ft
Mar 3, 2026
Listed
$349,000
$186/sq ft
+27
MOTIVATED SELLERS! Bring your offers! Experience the timeless appeal of this beautifully preserved 1800s Greek Revival residence in the center of Jamaica Village. Offering more than 2,500 square feet of living space, the home pairs classic architectural detail with thoughtful modern updates for effortless year-round living. Ideally situated just 15 minutes from Stratton Mountain and 25 minutes to Mount Snow, the location balances village convenience with premier access to Southern Vermont’s ski resorts and outdoor recreation. From the covered porch to the deck and veranda, the property invites relaxed outdoor living amid established gardens and peaceful surroundings. Jamaica State Park, River & Rye, the West River, the village library, and the local general store are all within easy walking distance. Inside, generous proportions define the layout. The expansive primary suite is complemented by three additional well-sized bedrooms, providing flexibility for guests or remote work. A well-appointed kitchen with a center island opens seamlessly to a formal dining room designed for memorable gatherings. The spacious living room offers a warm and welcoming setting, while the back porch and veranda create additional spaces to unwind. Blending historic character, modern comfort, and an exceptional village location, this property represents a rare opportunity to own a quintessential Vermont home—equally suited as a primary residence, seasonal retreat, or investment opportunity.
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29 Pikes Falls Rd is a 2520 square foot property with 4 bedrooms and 2 bathrooms. We estimate that 29 Pikes Falls Rd would rent between $2,685 / mo.29 Pikes Falls Rd is located in Jamaica, the 05343 zipcode, and the West River Valley Modified Union Education District #72a.