$995,000 $240 per sq.ft. Springfield VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 4144  |  Acres: 48.94
Friday Oct 10, 2025
Description: Once a tavern for travelers and a stagecoach stop in the early 1800s, 1607 Massey Road stands as a testament to Vermont's enduring spirit. This distinguished 1810 Federal style home rests gracefully on over 48 acres of rolling meadow, woodland, and quiet pasture, offering a rare blend of seclusion, scale, and story. With more than 4,100 square feet of living space, the home welcomes you with generous rooms, wide fireplaces in the living room and bedrooms, and a sense of history in every beam and board. A classic kitchen with a center island opens to a breakfast nook bathed in morning light. Upstairs, a vast attic space invites conversion into a workshop, studio, or retreat beneath the eaves. Outside, a wide entertaining deck overlooks a tranquil pond and dock, where summer reflections stretch long into the evening. Beyond the main home, an old sugar house and barn wait patiently for revival and a return to their maple-making roots or transformation into event or creative spaces. A cabin at the summit offers income potential as a short-term rental or a quiet guest escape. From the hilltop, the views roll endlessly across the Vermont valleys below, a scene unchanged for generations. Private. Peaceful. Poised between past and possibility, this is a property that doesn't just hold land and history, but the promise of legacy. See MLS Property & Listing Details & 35 images.

$1,100,000 $410 per sq.ft. Thetford VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2683  |  Acres: 6.4
Tuesday Oct 21, 2025
Description: An architect's personal home in Theford, VT, built for his family 38 years ago, is strategically perched on a very private, 6.4-acre parcel, surrounded by stone walls. The Cape is harmoniously augmented by Greek Revival details, most especially the colonnaded three-sided porch. This open land is complemented by neighboring large, conserved parcels. Quinibeck Road is generally lightly traveled. In addition to the perimeter walls, there is an extraordinary interior wall and sunken terrace built by a noted stone mason. A highlight of the home's interior is the stunning view from the front door directly through the rear door out to Tug Mountain. That dramatic view is amplified by the unexpected central hallway atrium with internal windows on the second floor. The interior of the house features light-filled rooms with an emphasis on intimate, social gatherings. Another fetching feature of the entire house is the use of unexpected niche spaces to accommodate personal flourishes such as small sculptures. The home is replete with other custom features such as built-in bureaus, bookcases, and the recessed porch linked to the primary bedroom. New roof in 2023; three working fireplaces; ample storage throughout; a spacious dry basement; and mature plantings. If desired, opportunities for creative repurposing of rooms abound. Don't miss an opportunity to acquire an elegant yet comfortable country home, close to Lake Fairlee and only 21 minutes from the Green in Hanover. See MLS Property & Listing Details & 44 images.

$169,000 $191 per sq.ft. Weathersfield VT Home »

2 Beds | 1 Baths |   Total Sq. Ft. 884  |  Acres: 0.33
Friday Oct 24, 2025
Description: This sweet ranch style home is located in the village of Perkinsville and features two bedrooms, one bath, living room, dining room and kitchen, nice lay out for easy, one floor living. Walk out basement with a new hot air furnace in 2025, newer hot water heater and updated electrical panel make this home a good candidate for someone looking to cosmetically update a home. Current family has outgrown the home and is excited for the home to start it's next chapter with a new family. Located on a dead-end road with outdoor space along with a fenced yard this could be just the home you are looking for. Please call or ask your agent for additional details. See MLS Property & Listing Details & 22 images.

$825,000 $375 per sq.ft. Weathersfield VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2200  |  Acres: 118
Monday Oct 20, 2025
Description: COUNTRY LIVING ON 118 ACRES WITH FULLY APPLIANCED, 4 BR's, 1.5 BATH HOME WITH ATTACHED GARAGE WITH 2ND FLOOR, A STATE-OF-THE ART PELLET BOILER, ROOF TOP SOLAR SYSTEM, SMALL POND, BARN AND STORAGE BUILDINGS. THE LAND BOAST ONE OF THE MOST BEAUTIFUL AND PLENTIFUL SUGAR BUSH IN THE STATE THAT EASILY ACCOMADATES OVER 4500 TAPS. SEVERAL WELL-MAINTAINED WOOD-LAND TRAILS TRAVERSE THE ACREAGE AND THE MATURE STATELY MAPLES. SPECTACULAR MT. ASCUTNEY VIEWS WITH CLEARING. JUST 1 MILE WEST OF EXIT 8. 30 MINUTE DRIVE TO OKEMO OR MT. SUNAPEE. See MLS Property & Listing Details & 17 images.

$269,000 $204 per sq.ft. Windsor VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1320  |  Acres: 0.13
Tuesday Oct 7, 2025
Description: Step into the timeless appeal of this beautifully maintained 1920s home, ideally situated in the heart of Olde Windsor. The inviting front patio welcomes you into a charming entryway that opens to a cozy living room, perfect for relaxing evenings or entertaining guests. Gleaming hardwood floors flow through the entry and dining areas, adding warmth and character throughout. The spacious dining room connects seamlessly to a well-appointed kitchen, offering both functionality and charm. A conveniently located half bath on the main floor includes an integrated washer and dryer for added ease. From the dining area, step out to the back patio and take in serene views of the expansive backyard, ideal for outdoor gatherings, gardening, or summer barbecues. Upstairs, you'll find three comfortable bedrooms and a full bath, providing plenty of space for family or guests. Perfectly positioned between Mill Pond, Lake Runnenede, and the Connecticut River, this home offers a unique blend of tranquility and convenience. Enjoy a leisurely 15-minute walk to Main Street, where local shops and restaurants create a vibrant small-town atmosphere. Combining vintage charm with thoughtful updates, this Olde Windsor gem is ready to welcome its next chapter. See MLS Property & Listing Details & 33 images.

$329,000 $200 per sq.ft. Windsor VT Home »

2 Beds | 2 Baths |   Total Sq. Ft. 1649  |  Acres: 0.18
Monday Sep 29, 2025
Description: Open House 10/4/1025 11Am-1Pm. This lovingly maintained Cape-style home, perfectly set on a 0.18-acre corner lot. With 2 bedrooms, 1.5 bathrooms, a welcoming covered porch, and spacious basement, this home blends classic Vermont character with everyday comfort. The home has a standing seam roof and a brand new boiler, with timeless features such as built-in cabinetry, hardwood floors, and ample closet space. Bonus rooms on each floor add to its charm and flexibility. The two-car garage with attic storage offers plenty of room for vehicles, tools, and more. Inside, the traditional layout provides a functional, warm, and inviting flow but leaves room for adding your own personal touches. Enjoy the convenience of being within walking distance to local amenities like Kennedy's Pond and the Windsor Fairgrounds all while savoring the peace and space of your corner lot, ideal for gardening, play, or quiet relaxation. See MLS Property & Listing Details & 41 images.

$425,000 $295 per sq.ft. Woodstock VT Home »

2 Beds | 2 Baths |   Total Sq. Ft. 1440  |  Acres: 0.79
Sunday Oct 5, 2025
Description: This charming 2-bedroom ranch house offers a nice layout for main floor living. Features include a sunroom entrance, two bedrooms, a full bath, laundry room, and a main living/dining area with a kitchen, all within a rural setting with ample natural light, local views, and a deck. Recent updates include a primary bedroom ensuite featuring a custom walk-in shower and double sinks, new flooring, a brick accent wall in the living room, fresh paint, and a cleared and seeded backyard. A 3-bedroom septic system installed in 2021, a drilled well replacing the spring water source, and generator wiring for power backup. Situated on a quiet country road between Woodstock and South Woodstock, offering easy access to local amenities and entertainment. See MLS Property & Listing Details & 42 images.

$439,000 $271 per sq.ft. Woodstock VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1617  |  Acres: 0.65
Wednesday Oct 1, 2025
Description: Charming 4 bedroom farmhouse with attached barn/garage with lots of overhead storage is located across the road from the scenic Ottauquechee River. Minutes from Woodstock Village Green with all of its amenities and a short distance from Killington with its world renown Ski Resort. Year round activities abound ! The house has a sunny eat in kitchen, spacious dining room and a living room complete with a wood burning fireplace. A bedroom and full bath on the first floor adds to convenience of living . The charming front porch with views of Killington is a lovely place to enjoy relaxing and entertaining friends . Make an appointment today to view this lovely property . See MLS Property & Listing Details & 45 images.

$725,000 $202 per sq.ft. Woodstock VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 3584  |  Acres: 5.1
Saturday Oct 25, 2025
Description: This South Woodstock contemporary residence was designed by the original architect-owner to showcase Vermont's changing seasons and capture views of the Kedron Brook as it wanders through the property past small meadows tucked in along the banks. The home can be accessed privately at grade level through the heated garage and mudroom, while guests enter via a covered entry to the upper level. The lower walk-out level of the home has two bedrooms, a shared bath, laundry and workshop. The elevated second floor is dedicated to gathering spaces including a great room with cathedral ceilings, eat in kitchen and family room that opens out on to a broad deck with overlooking the brook as it flows to the nearby Woodstock golf course and Athletic Club. The spacious primary bedroom offers an ensuite bathroom and abundant closet space. The main floor guest bedroom with loft is served by an adjacent bathroom. The two-stall multi-purpose barn opens to a small pasture and a fence yard for pets. A home for all seasons and reasons. See MLS Property & Listing Details & 40 images.

$795,000 $249 per sq.ft. Woodstock VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 3190  |  Acres: 2.94
Friday Oct 24, 2025
Description: See MLS Property & Listing Details & 44 images.

$925,000 $321 per sq.ft. Woodstock VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2882  |  Acres: 2.08
Thursday Oct 2, 2025
Description: Stunning contemporary extensively renovated and idyllically situated on a westerly facing hillside overlooking the village of Woodstock offers a coveted Woodstock location for those wanting a peaceful Vermont countryside vibe to unwind but the vibrant Woodstock Village life at the foot of your hill! The interior design presents a more refined open concept design that offers both openness but a more defined layout for functional separation and intimacy. A captivating light filled living room that opens onto a mahogany deck is centered upon a handsome fireplaced wall that is open on both sides to allow flow into a lovely eat-in kitchen detailed with quartz counters. A primary ensuite bedroom, study/office, and full bath complete the main level. The lower level presents a second living room that opens onto a patio and centers upon a second fireplace. Three bedrooms and a terrific laundry room/mudroom complete the lower level. Enjoy relaxing, entertaining, and taking in the sunsets from the westerly facing patio and deck. Perfect as a primary or secondary home with all season recreation, theatre and the arts, dining, and shopping just minutes away and easy access to all the amenities and major employment the Upper Valley has to offer. Showings begin with Public Open House Saturday Oct 4 from 1-3pm. See MLS Property & Listing Details & 31 images. Includes a Virtual Tour

$1,200,000 $439 per sq.ft. Woodstock VT Home »

Price Change! Reduced by $50,000 down 4% on October 14th 2025
4 Beds | 3 Baths |   Total Sq. Ft. 2736  |  Acres: 0.86
Monday Sep 29, 2025
Description: Open House! Saturday Oct 18 from 10-12. Once known as the Sunshine Nursery School, this home's history expands back to ~1870 and now it stands as a spacious and beautifully updated residence with an expansive terraced yard (one of the largest near the village) and elegant interiors. High ceilings, high-quality wood floors, and sun-filled rooms define the main level, where a gracious primary ensuite with step-in shower, and a glass-lined sunroom create an effortless flow. Thoughtful conveniences include a mini-split for year-round comfort, laundry on the main level, and an eight-foot slider off the dining room that opens to a private deck overlooking the backyard. Upstairs, an apartment with private entrance extends the home's versatility with its own kitchen, living area, ¾ bath, and two bedrooms--perfect for guests, extended family, or private quarters. Outdoors, the property is framed by beautifully established perennial gardens and an expansive yard, offering rare in-village green space on +-.89 acres! A paved drive, two-car garage with overhead storage, standby whole-house generator, and public water and sewer add to the ease of ownership. The location is unmatched--just a street away from the elementary school, Vail Fields, the Village Green, and miles of walking trails. Schedule a private showing and see this grand home for yourself! See MLS Property & Listing Details & 35 images.

$1,295,000 $485 per sq.ft. Woodstock VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2668  |  Acres: 8.32
Sunday Oct 5, 2025
Description: This traditional New England Colonial, designed and custom built by Vermont Vernacular Builders, is sited to capture idyllic all-around mountain views and southern light. The spacious four-bedroom home features wide board floors, exposed beams, and a sun-filled chef's kitchen and den. New Thor stainless steel 48" propane range installed October 2025. Privately set on over 8 acres, the property offers true seclusion with the convenience of being just minutes to Woodstock Village, close to Killington and Okemo skiing, and near local favorites including Ramunto's Pizza and nearby event venues. Amenities include a private in-ground pool with expansive mountain views, plus an oversized garage/barn with storage and space above for potential guest quarters. An ideal countryside retreat for year-round living or a second home escape. See MLS Property & Listing Details & 40 images.

$2,600,000 $867 per sq.ft. Woodstock VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 3000  |  Acres: 112.88
Thursday Oct 16, 2025
Description: Gilbert's Hill is one of Vermont's most celebrated properties and a national landmark for its contribution to the sport of alpine skiing. Spanning 112.88± acres in Woodstock (79.31 acres) and Pomfret (33.57 acres), the farm is recognized as the birthplace of lift-served skiing in America, where the first rope tow was installed in 1934. Today, its open pastures, rolling terrain, and historic ski hill remain wonderfully intact -- a living landscape that forever changed the trajectory of winter sport and the development of recreational skiing in the United States. At the heart of the property is a restored circa 1855 Greek Revival brick farmhouse with four bedrooms, two bathrooms, and a classic mid-19th-century clapboard addition with kitchen and garage. Original details have been thoughtfully preserved, blending historic integrity with comfort and charm. Surrounding the main house is a collection of restored historic buildings, including: a 1934 ski hut, now a three-season cottage with two bedrooms, kitchen and full bathroom; a carriage barn with seasonal kitchen and half bathroom; a dairy barn with milking parlor and six stanchions; and the original milk house. There is also a modern greenhouse pavilion with seasonal half bathroom and a detached 4-bay equipment shed. The land, which includes a vineyard with 700 vines, is conserved with the Vermont Land Trust. The house, dairy barn, milk house and 1934 ski hut are also protected by a historic preservation easement. See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

$18,000,000 $1,438 per sq.ft. Woodstock VT Home »

7 Beds | 10 Baths |   Total Sq. Ft. 12520  |  Acres: 183.7
Thursday Oct 16, 2025
Description: Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodstock. From the valley floor to the top of Meetinghouse Hill, you will be inspired by its beauty, a mesmerizing 183.7+/- acre oasis over gorgeous terrain with fields, woodlands, trails, and stone walls. The historic 2-bedroom guest house and party barn are fully restored, and located next to the swimming pond. The main residence, completed in 2010, consists of the center core with porch - for cooking, gathering and entertaining; the owner's quarters with a 2nd floor suite and 2 bedrooms below; the guest wing with 3 first-level bedrooms, second-floor game room and adjacent 8-bed bunk room and a 4-story octagon with wine cellar at the base and flexible multi-use spaces above. All 7 bedrooms are ensuite plus 3 powder rooms. The attached gambrel barn is a professional grade gymnasium with 6-car heated garage underneath. The interior is like a grand lodge in the American West while the exterior with shingles and gambrel barn is traditional New England. The systems and mechanicals are all commercial grade. The finishes and craftsmanship are consistently superb. The atmosphere is relaxed and fun. As a complete fully furnished package, each and every attribute at Star Hill Farm - the location, land, exposure, privacy, views, guest house, barn, pond, residence and gymnasium- is exceptional, creating one of the finest properties in Vermont. See MLS Property & Listing Details & 60 images. Includes a Virtual Tour