Woodstock, Vermont listings for sale

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$595,000 - Woodstock, VT
20 Gully Road Woodstock, VT - Classic Historic Vermont Farmhouse just outside of Woodstock Village! This sale even includes an extra subdivided lot! C.1903 Dormered Cape set on approx. 2.6 acres of level, open land bordered by a tranquil brook. The property offers a picturesque setting with extensive perennial gardens, a patio by the stream, firepits, covered front porch, rear porch, and deck—perfect for relaxing or entertaining. Inside, the home exudes warmth and comfort, featuring 2,600+ sqft, four bedrooms & three bathrooms. The inviting family room boasts a wood-burning fireplace, while the cozy living room is enhanced by a gas fireplace. The kitchen, with its soapstone Hearthstone brand woodstove and charming breakfast nook, is a delightful gathering space. Updates include newer windows, septic, appliances, and mechanicals, ensuring modern efficiency while maintaining the home’s classic appeal. An oversized one-car garage provides ample storage and parking. There is additional storage above the garage with room for potential expansion into an office, game room or studio apartment. This classic Vermont farmhouse offers the perfect balance of historic charm and modern convenience, just 4 minutes from Woodstock’s vibrant village center. The Woodstock Green is only a 5 minute drive, as is skiing at Saskadena Six. Close to everything the Upper Valley has to offer!
1903 | 4 | 1 | 2,678 sqft.
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$549,999 - Woodstock, VT
1613 West Woodstock Road Woodstock, VT - WOODSTOCK-TURNKEY AND CONVENIENT! This totally renovated, move-in ready home located a few minutes to Woodstock Village, 20 minutes to Killington, 30 minutes to DHMC. Enjoy loads of recreational trails of all kinds, just minutes away.  Excellent spot with walking distance to the abutting Woodstock Union Middle School/High School. Newly Renovated inside and out. Spacious open concept living on main floor. The large, finished basement has a TV recreation area, workout space and pool table area. Custom built in cabinetry in the upstairs bedrooms. Private and wooded back yard with a covered porch, perennials, berries and gardens.  Huge potential to add-on, start a home business, create a rental unit or leave quaint and cozy as it is.  This property would be ideal for a primary residence or short-term rental investment property. Schedule your tour today of this sweet Woodstock GEM! PUBLIC OPEN HOUSE MAY 24, 2025, FROM 10AM TO 2PM. COME STOP BY TO SEE THIS TURNKEY HOME!
1944 | 3 | 2 | 1,344 sqft.
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$239,000 - Woodstock, VT
442 E Woodstock Road Woodstock, VT - Airy, tranquil and quiet, this former yoga studio space has been converted into a two bedroom condo. Sweeping views through the Palladian window, large living area with soaring vaulted ceiling, newer kitchen with granite counters and newer bath with walk in shower. Spacious entry can accommodate bikes, skis and more. Walking distance to shops, restaurants, entertainment and recreation in the beautiful historic village of Woodstock. This unit is part of Twin Pines Housing Trust's affordable housing program. Full price is $399,000. Twin Pines will pay the downpayment, so price to buyer is $239,000. An application to Twin Pines Housing Trust Homeownership Program is required to purchase this condo. Household income limits are based on 120% AMI for Vermont Nonmetro.
1980 | 2 | 0 | 1,190 sqft.
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$226,000 - Woodstock, VT
67-1 Safford Commons Way Woodstock, VT - This affordable 1,025 square foot condominium was built in 2022 and is conveniently located near amenities, shopping, and schools. 2 bedrooms, 2 baths. This unit is part of the Twin Pines Housing Trust's affordable housing program. Full price is $360,000. Twin Pines will pay the downpayment, so price to buyer is $226,000. An application to Twin Pines Housing Trust Homeownership program is required to purchase this condo. Household income limits are based on 120% AMI for Vermont Nonmetro.
2022 | 2 | 1 | 1,025 sqft.