304 houses for sale in South Shaftsbury

Much larger than it looks and completely redone in 2022, with the only evidence remaining of the 1934 construction being a crawlspace through a hatch in the rear of the basement. Offering 3 bedrooms and 2 bathrooms this home is very much like new. All the systems are modern. Living room/dining room/kitchen, mud room with laundry and bedroom on the main level. Upstairs is the primary bedroom with private bathroom and an additional bedroom. Outside you'll find a large front yard that has been partially fenced, a large covered, wrapping deck for entertaining and outdoor dining and a dog fenced area. Great location across the road from a calm river. This home is larger than it appears from the road. A must see home in move in ready condition that could possibly sold furnished

Nestled on 9.89 secluded acres in North Bennington, this exceptional 4-bedroom, 3-bath home offers the perfect blend of character, comfort, and versatility. The sprawling residence features a beautiful interior highlighted by stunning post-and-beam cathedral ceilings and inviting living spaces designed for both everyday living and entertaining. The heart of the home is the large open space combining a kitchen and spacious living room, where a cozy wood stove creates a warm and welcoming atmosphere. Additional living spaces include a formal dining room, private office, library space and a large mudroom with attractive brick flooring that provides a practical transition from the outdoors. Upstairs, you'll find a wonderful studio space ideal for artists, hobbyists, or anyone seeking a creative retreat. The property also boasts a huge, heated workshop, offering endless possibilities for craftspeople, entrepreneurs, or storage needs. Adding to the home's versatility is a second-floor studio

Opportunity awaits at this unique property with an exceptional setting along the Walloomsac River. A true Vermont farmhouse offering three bedrooms and two bathrooms, situated on a flat, park-like lot with mature landscaping, open green space, and beautiful river frontage. The serene setting creates a peaceful atmosphere rarely found in properties with such versatile potential. A large barn provides abundant storage, workshop space, or the opportunity for a variety of future uses. Inside, the home is ready for renovation and updates, making it an ideal project for investors, entrepreneurs, or buyers looking to bring their own vision to life. The main level features a well designed layout, highlighted by a spacious eat-in kitchen, a full bathroom, and a cozy living room with a pellet stove. The front door leads to a covered porch overlooking the scenic golf course at Mount Anthony Country Club. A separate dining room and a versatile room that can serve as a bedroom, den, or home office

Welcome to your own private oasis! Set on 30 private wooded acres, this well-maintained three-bedroom, 2.5-bath Colonial presents a rare opportunity to enjoy expansive acreage, exceptional mountain views (including the Bennington Battle Monument!), and peaceful surroundings in a highly versatile tri-state location near the Vermont, Massachusetts, and New York borders. The 2,083 square-foot home blends classic character with modern convenience, featuring wide pine floors across the main level, fiber-optic internet, and thoughtfully designed living spaces. The light-filled kitchen wing offers vaulted ceilings, a skylight, garden window, and KraftMaid cabinetry, while the spacious dining/keeping room is anchored by a striking Rumford fireplace crafted by a master mason. Flexible living areas include a TV room/library and a main-level bedroom with an attached bathroom with walk-in shower. Upstairs are two very generously sized bedrooms with a shared full bathroom and ample closet spaces. A

Elegant and stately, this distinguished 1910 home is beautifully set in the heart of Old Bennington, Vermont. Thoughtful renovations began in 2000, carefully preserving the home's historic character while enhancing comfort and functionality throughout. Offering over 6,000 square feet of gracious living space, the residence features seven bedrooms, six baths, and six fireplaces, with timeless architectural details at every turn. Enter into a large, welcoming foyer highlighted by a grand staircase that sets the tone for the home's classic elegance. Generous living and gathering spaces flow seamlessly, while the chef's kitchen enjoys dramatic eastern views, filling the home with morning light. The primary suite is a true retreat, complete with its own fireplace and a large sunroom perfect for quiet mornings or evening relaxation. A convenient second-floor laundry area enhances everyday living. Outside, the 4.5-acre setting is framed by stacked stone walls, a serene spring-fed pond, and lo

This well-maintained New Englander offers the perfect balance of classic character and comfortable living. Featuring four bedrooms and two updated bathrooms. The home provides spacious, comfortable living throughout. The recently renovated kitchen is both stylish and functional, while the updated bathrooms add contemporary appeal. Large rooms and a thoughtful layout create a welcoming atmosphere for everyday living and entertaining. Outside, you'll find a deep, fully fenced backyard with plenty of room for recreation, gardening, or pets. A beautiful deck provides the perfect setting for outdoor dining, relaxing, and entertaining. Enjoy the convenience of an in-town location within walking distance of downtown restaurants, shops, and local attractions. The property is also just minutes from services and all the amenities Bennington has to offer. Albany airport is 45 minutes driving, ski areas to the north and east, also approximately 45 minutes, NYC and Boston are both a 3 hour drive

Filled with natural light and designed for comfortable living, this charming 3-bedroom, 3-bath contemporary home offers a spacious, versatile floor plan with room to live, work, and create. Light wood flooring and multiple skylights enhance the warm, inviting interior, while thoughtfully designed living spaces provide comfort and flexibility for today's lifestyle. The main level features two generous living areas, making it easy to entertain, relax, or create separate spaces for family, guests, or a home office. A dedicated dining room offers the perfect setting for holiday gatherings and everyday meals, while the convenient first floor bathroom and laundry room add to the home's everyday functionality. Two of the three bedrooms are exceptionally spacious (one of which has an ensuite bathroom), providing peaceful retreats with ample room for sitting areas, home offices, or expanded storage. A dedicated art studio is a rare and inspiring bonus, ideal for artists, makers, remote work, or

Secure a smart, low-maintenance income property featuring four well-kept units-two 2-bedroom and two 1-bedroom-on a dead-end road. This is turnkey living for tenants and hassle-free ownership for you. Each unit has dedicated washer/dryer hookups and fully separated utilities (electric, gas or oil, hot water), so tenants manage their own bills and turnover is smooth. With reliable, long-term renters in place, enjoy immediate cash flow and minimal management effort. The private setting offers privacy and minimal traffic, while consistent occupancy make this an ideal buy-and-hold investment. Don't miss this rare opportunity to own a dependable, income-producing asset in an out of the way location

This cute 3-bedroom, 1-bath cape offers comfortable in-town living with a fully fenced yard and recently renovated kitchen and bath. The laundry hookups are on the first floor which adds everyday convenience. Enjoy morning coffee or evening relaxation in the enclosed 3-season porch with outdoor fenced space perfect for pets, play, or gardening. The upstairs bedroom features unique built-ins that add both charm and storage. Conveniently located close to shopping, dining, recreation, and just minutes to the Bennington Recreation Center, this home combines comfort, character, and accessibility in a desirable neighborhood

This cute 3-bedroom, 1-bath cape offers comfortable in-town living with a fully fenced yard and recently renovated kitchen and bath. The laundry hookups are on the first floor which adds everyday convenience. Enjoy morning coffee or evening relaxation in the enclosed 3-season porch with outdoor fenced space perfect for pets, play, or gardening. The upstairs bedroom features unique built-ins that add both charm and storage. Conveniently located close to shopping, dining, recreation, and just minutes to the Bennington Recreation Center, this home combines comfort, character, and accessibility in a desirable neighborhood

Welcome to one of the most coveted locations in Bennington, Vermont known to locals as the West End. Steeped in history, this remarkable property was built c.1928 with ties to the Colgate Estate located on Mount Anthony. A stones throw away is the original Fillmore Farm, primarily known for its sheep. In 1929, the farm began production of milk and then built its large dairy plant in 1939. It can be surmised that this property was for the intent of upper management housing for the farm. With sprawling views to the north, south and west, this location does not disappoint! A typical farmhouse style home that esthetically blends rustic and modern elements for easy living. A generously sized kitchen is perfection for entertaining and for spending time with family and friends. The living room invites a space for conversation, a cozy fire during the chilly Vermont evenings, or simply relaxing taking in the divine views at sunset. More casually, the family room offers exposed beams, vaulted ce

Gorgeous setting for this newly constructed home built in 2025, offering breathtaking views from the expansive front porch on 10+/- private acres. Thoughtfully designed with quality craftsmanship throughout, the custom kitchen features beautiful cabinetry, a large center island, gas range, and classic farmhouse sink, all open to the inviting living room with a cozy gas fireplace. The stunning sunroom serves as the dining area and showcases cathedral wood ceilings that fill the space with warmth and natural light. Rich hickory floors flow throughout the main living areas, adding character and style. The main-level primary suite offers convenience and comfort with a spacious full bath, creating easy one-level living in a peaceful country setting. The second floor features oversized bedrooms with vaulted ceilings, connected by a Jack-and-Jill bath with tiled floors and separate vanities. At the center of the upper level is a welcoming sitting area complete with a wet bar, leading out to a

Terrific in town location for this 3 bedroom, 2 bathroom home in Bennington. Offering living room, large kitchen, formal dining room and office/study. Covered porch and patio. Privacy bushes and yard. Property is being sold as-is

Over 3 acres, a brook and lots of woods for walking. Room for a terraced garden, tons of parking and minutes to Bennington! This 2 bedroom ranch style home has a huge eat in kitchen and a lovely big living room with lots of windows. There is a bonus sun room with laundry. Owners are using an attached shed as a chicken coop! Sweet find at this affordable price!

Lovingly custom built in 1989 and offered for the first time, this beautifully maintained expanded Cape is a rare opportunity to own a home that has been cherished by its original family from the very beginning. Thoughtfully designed with generous room sizes and a timeless floor plan, the home offers warmth, comfort, and quality throughout. Inside, generous room sizes, timeless design, and quality craftsmanship create a warm and inviting atmosphere. Rich hardwood floors, a wood-burning fireplace, and tasteful decor blend traditional charm with everyday comfort. The spacious kitchen features a desirable walk-in pantry, while the home's exceptional condition makes it completely move-in ready. A new roof installed in 2021 adds peace of mind. The grounds are equally impressive, showcasing mature landscaping, retractable awnings, and a charming garden shed. Beautifully maintained inside and out, this turnkey home reflects decades of pride of ownership and offers a rare opportunity to become

This historic house, built in 1880, is nestled in the quiet village of North Pownal. It is situated on a large, level lot and offers the timeless charm of yesteryear. The first floor features a roomy kitchen with Kenmore Plus Stainless-Steel appliances, an open-concept living room and dining room, an updated bathroom, and a convenient first-floor laundry room. The back porch has been partially converted into a mudroom and a first-floor master suite, which just needs a few finishing touches to be complete. The partially finished master bath boasts a beautiful custom stone/tile shower. The second level includes three bedrooms and a full bathroom. Many upgrades have been made in recent years, including a new heating system (2019), water heater (2019), oil tank, and well pump (2024). The property also benefits from town sewer, vinyl replacement windows, and low-maintenance vinyl siding. For winter enthusiasts, numerous ski resorts are within an hour's drive, such as Mt. Snow, Stratton Moun

Recently this home was a 2 unit (up and down). The current owner has doing work to convert it into a large single family home. Currently 4 bedrooms, 2 bathrooms and many possible room configurations. Also could easily be converted back to a 2 Unit. Many possibilities to put your finishing touches on this property with a lot of square footage

Well-built and lovingly maintained through the years, this 3-bedroom, 2-bath ranch offers the ease of single-level living with both a deck and covered porch to take in the mountain views. An attached two-car garage, full basement, and storage shed provide plenty of room for hobbies, outdoor gear, and all the extras. Perched atop 1.4 acres on a gentle hill in Pownal, you'll enjoy a peaceful setting while remaining just minutes from both Bennington and Williamstown, Massachusetts for dining, shopping, cultural attractions, and everyday conveniences. Outdoor enthusiasts will appreciate nearby access for hiking, ATV riding, and exploring all that Southern Vermont has to offer. Come see and make it yours!

Welcome to Spruce Peak. Situated on 21.1 private acres, this beautifully maintained center hall colonial offers 2,439 square feet of thoughtfully designed living space. Built in 2001, the home features 3 bedrooms, 3 baths, quality craftsmanship, and a functional floor plan. Warm hardwood floors extend throughout the main living areas, creating an inviting interior. The spacious kitchen is appointed with cherry cabinetry, updated stainless steel appliances (2024), radiant heated floors, a large double-door pantry, and seamless access to the dining and living areas. French doors open to the rear deck, providing an easy transition to the outdoor living space. A wood stove adds both warmth and character to the main living area.Designed for convenient first-floor living, the primary suite includes a walk-in closet and a private 3/4 bath, along with easy access to the first-floor laundry. Two additional bedrooms each feature walk-in closets, providing generous storage throughout the home. Ab

Welcome to Spruce Peak. Situated on 21.1 private acres, this beautifully maintained center hall colonial offers 2,439 square feet of thoughtfully designed living space. Built in 2001, the home features 3 bedrooms, 3 baths, quality craftsmanship, and a functional floor plan. Warm hardwood floors extend throughout the main living areas, creating an inviting interior. The spacious kitchen is appointed with cherry cabinetry, updated stainless steel appliances (2024), radiant heated floors, a large double-door pantry, and seamless access to the dining and living areas. French doors open to the rear deck, providing an easy transition to the outdoor living space. A wood stove adds both warmth and character to the main living area.Designed for convenient first-floor living, the primary suite includes a walk-in closet and a private 3/4 bath, along with easy access to the first-floor laundry. Two additional bedrooms each feature walk-in closets, providing generous storage throughout the home. Ab

This is a RARE two lot offering! It is located on Cemetery Rd in Arlington,VT with quiet, secluded lots. Great opportunity for multi-generational living, guest house, rental income, air bnb, extra space or great re opportunity. House #1 is a two story house on 2.29 surveyed acres with 4 bedrooms and 1 3/4 bathrooms. The living room features a cathedral ceiling with skylights and a wood burning fireplace with beautiful river stone hearth. Has all new appliances. This house has a cozy light-filled layout and character. There is also a hand built 10x12 wood shed for extra storage. House #2 is on a separate 1.5 surveyed acre lot. It has a well maintained double wide trailer that has 3 bedrooms and 2 bathrooms. This house features a primary suite with a walk in closet and en-suite bathroom. These houses currently share a driveway that can easily be separated. This provides excellent flexibility for a new home owner. Both homes are being sold as is and are ready for you to bring your vision

OPEN HOUSE SCHEDULED FOR 6/21/26 HAS BEEN CANCELED! SELLER HAS ACCEPTED AN OFFER! Completely Updated with Stunning Views and a Prime Central Location! This exceptional home truly has it all. From the moment you step inside, you'll be welcomed by a warm and inviting atmosphere that instantly feels like home. Thoughtfully designed with a seamless flow, the living spaces are both comfortable and functional. Featuring extensive updates throughout, this home is truly move-in ready-simply unpack and start enjoying all it has to offer. Take in breathtaking views of the Green Mountains from the comfort of your home. Enjoy year-round comfort with newly installed central air conditioning, perfect for Vermont's warmer summer months. Adding to the home's versatility is an unfinished room on the first level with legal egress windows, offering excellent potential to be finished as an additional bedroom, guest suite, home office, or hobby space. This flexible area provides an opportunity to customize

Move right into this beautifully updated 3-bedroom, 1-bath home situated on 0.61 acres on a private dead-end road in Arlington. Offering a peaceful setting just minutes from town, this property combines privacy with convenience. The level yard features a mix of sunny and shaded spaces, perfect for outdoor enjoyment, while a year-round stream adds to the natural beauty of the property. Inside, you'll find numerous recent improvements, including an updated kitchen, new roof, hot water heater, garage concrete floor, basement bulkhead, flooring, fresh paint, and more. With so many major updates already completed, this home is truly move-in ready and offers an excellent opportunity to enjoy Vermont living in a quiet, inviting location

The historic Arlington Inn and Spa is the centerpiece of scenic Arlington, Vermont. It features a tavern, restaurant and massage spa room. There are 15 guest rooms in 3 buildings, and an antique event barn on over 3.5 beautifully landscaped acres. This unique property can easily be configured in many creative ways. It could remain as an inn with a restaurant and bar. It could become a restaurant and event destination for weddings and parties. And it would make a wonderful family compound or corporate retreat. In addition to three guest suites, the c. 1848 Main Inn offers a commercial kitchen serving formal and informal dining spaces and the fully renovated Deming Tavern. The romantic Tavern features an antique bar front crafted from a pulpit from the Old First Church in Bennington and Pullman Railcar lighting in a nod to Martin Chester Deming, the original owner of the property and a railroad magnate. While respecting historical detail, the current owners have added modern conveniences

The historic Arlington Inn and Spa is the centerpiece of scenic Arlington, Vermont. It features a tavern, restaurant and massage spa room. There are 15 guest rooms in 3 buildings, and an antique event barn on over 3.5 beautifully landscaped acres. This unique property can easily be configured in many creative ways. It could remain as an inn with a restaurant and bar. It could become a restaurant and event destination for weddings and parties. And it would make a wonderful family compound or corporate retreat. In addition to three guest suites, the c. 1848 Main Inn offers a commercial kitchen serving formal and informal dining spaces and the fully renovated Deming Tavern. The romantic Tavern features an antique bar front crafted from a pulpit from the Old First Church in Bennington and Pullman Railcar lighting in a nod to Martin Chester Deming, the original owner of the property and a railroad magnate. While respecting historical detail, the current owners have added modern conveniences