336 properties for sale in South Shaftsbury

If you are seeking privacy and serenity, look no further. Your private drive will lead you to your home on the hill with no neighbors in sight. You will enjoy this peaceful spot, yet you are just 5 miles to downtown Bennington. 52+ acres that include open land perfect for kids, animals, gardens, sledding, or all of the above. The blueberry bushes are big producers. This home was built by the owners in the '80s. The 3300+ square feet of living area on the upper level and another 3300+ on the lower level ready to be finished. As you can see, the lower level has plenty of windows and will be very flexible space to use. The two-car garage is attached to the house. From there, into the mudroom. The kitchen is very generous. There's room for your breakfast table, a couple of easy chairs and a love seat, and the woodstove will make this a cozy country kitchen to be. This is a 'cooks dream'. The commercial range will make your friends jealous, as will the pantry and stained glass on the upper

Welcome to the Fox Hill Community and a beautiful modern home tucked away on a private road in Shaftsbury, Vermont offering the perfect blend of privacy, comfort, and stunning Vermont scenery. The home offers 3 bedrooms and 3 bathrooms along with gorgeous mountain views. There is a cozy fireplace in the living room with ample space provided for a family, friends and entertaining. The landscaping is built around the property to accent the outdoors as a beautiful, serene retreat. Whether you're entertaining outdoors, unwinding by the fire, or taking in the breathtaking views, this home offers a lifestyle that's hard to match. Contact me today to schedule your private showing and experience this exceptional property for yourself!

Set on 2.5 beautiful acres, this inviting Cape-style home offers a wonderful combination of comfortable living space, character, and versatile outbuildings. The primary suite is conveniently located on the main level, with two additional bedrooms and a full bath upstairs. An attached two-car garage provides convenient parking and additional storage. The spacious living room features wide pine floors, built-in cabinetry, a fireplace, and a slider leading to the deck. The dining room continues the charm with wide pine flooring, a large window, and a built-in corner cabinet. Outside, the property offers a large barn with two stalls and an expansive workshop, along with two additional sheds for plenty of storage. There is also the possibility of restoring the property's former pond, adding another attractive feature to the landscape. The kitchen is ready for renovation, offering an opportunity to create a space tailored to your own style and needs. With 2.5 acres, a barn, workshop, attache

Discover quintessential Vermont living in this charming home, ideally situated on 6.9 serene acres in scenic Shaftsbury, a picturesque town in Southern Vermont. This meticulously maintained residence offers a blend of rustic charm and modern sophistication, providing a tranquil retreat with convenient access to area amenities and attractions. Thoughtful renovations have elevated its interior, particularly in the two full bathrooms, which now showcase exquisite glazed Italian subway tiles, natural river stones, and other elegant natural surfaces, creating spa-like environments. A recently added Danish wood stove promises cozy evenings and efficient heating, adding to the homes inviting ambiance. One of the three bedrooms has been artfully transformed into a versatile library/office. This beautiful space is perfect for quiet contemplation or remote work, and is designed to gracefully accommodate overnight guests, offering both comfort and privacy. Enjoy the expansive Vermont outdoors fro

Gorgeous, renovated Colonial offering exceptional flexibility, thoughtful design, and timeless charm. This beautifully updated property features a spacious main residence along with a stunning addition that includes a full in-law suite and a private studio above ideal for guests, extended family, a home office, or potential rental income. Solar panels installed above the garage power efficient mini-split systems, and a Tesla Powerwall provides added energy independence and peace of mind. The main house offers four bedrooms, a fabulous chef's kitchen with quality finishes and generous workspace, and warm, inviting living areas filled with abundant natural light. Magnificent views of Mount Anthony and the sweeping five-acre meadow below can be enjoyed from the kitchen, dining room, living room, and screened porch-where wildlife is often part of the daily landscape. A new large enclosed porch further expands the living space, creating the perfect setting to relax or entertain year-round.

Welcome to easy Vermont living in this beautifully maintained ranch-style home offering more than 2,000 finished square feet in one of North Bennington's most desirable neighborhoods. Set on a quiet cul-de-sac with lovely mountain views, Harvest Hills offers a wonderful sense of community, including a large neighborhood pond for residents to enjoy. The location is equally appealing; close to the village school, market, restaurants, and the popular Mile Around Woods trail. Inside, a spacious living room with a traditional brick fireplace flows into the bright, open dining and kitchen areas, creating an inviting layout for everyday living and entertaining. The charming kitchen features a breakfast bar, pantry, stainless steel appliances, and abundant natural light. Three comfortable bedrooms and two full baths include a primary bedroom with its own en suite bath. The finished lower level adds valuable flexibility with a generous family room, recreation space, or home office, complemented

The Dexter Road Farmhouse, Circa 1800 In 1922, poet laureate and Shaftsbury resident Robert Frost was inspired by the bucolic nearby backroads to write Stopping by the Woods on a Snowy Evening. Dating back more than 225 years, this charming farmhouse offers a rare opportunity to own a piece of Vermont history while embracing the slower pace and natural beauty that define the region. Tucked away at the end of a peaceful, tree-lined town road, the property is ideally suited as a second home, creative retreat, or year-round residence. Lovingly cared for by the same family for over 70 years, the home retains much of its original character and craftsmanship. Wide pine floors, original moldings, classic woodwork, traditional wall and ceiling boards, and a gracious entrance hall create a warm and authentic farmhouse atmosphere. Set on approximately 40 acres with a picturesque skating pond, the property offers abundant space to explore, garden, walk, and enjoy the pastoral surroundings. Writer

Discover quintessential Vermont along this idyllic country road embodying peace and serenity. The property features mature trees and a peaceful, quiet location. Close to Lake Shaftsbury State Park and Lake Paran as well as many hiking trails and ski areas. This would make a perfect weekend getaway,, or full-time home. New vinyl siding, a recent metal roof, and newer furnace. Enjoy the convenience of a drive through garage and circular driveway which can easily fit five or six cars when hosting picnics in the large backyard. With high speed internet, working from home is a breeze. The flexible bonus room would make an ideal home office, playroom, guest room, or a future bedroom by adding insulation and a heat source. Wonderful neighborhood full of friendly folk. The tree lined road is perfect for walking, running, biking, and dog walking. Conveniently located halfway between Manchester and Bennington for food, friends, and shopping. It may be small, but it's full of potential!

Set privately on 25.34 acres, this 3BR/2BA contemporary-style home offers expansive views and a peaceful setting just 15 minutes from Bennington. Kitchen with breakfast nook opens out onto a back deck and the spacious living room features a cathedral ceiling and dramatic floor-to-ceiling fieldstone fireplace, creating an impressive focal point and inviting gathering space. First floor also includes a formal dining room and first floor bedroom or office as well as a full bath. On the second floor, the primary suite includes a large bathroom with a walk-in shower and tub, with a layout that may accommodate accessibility needs and a second guest bedroom includes a half bath. Basement-level 2-car garage provides workspace and a dedicated laundry area. The property offers a wonderful combination of privacy, acreage, and convenience, with plenty of room to enjoy nature and and the surrounding landscape. There is ample room for gardening and play! The home needs some repairs and updating, pro

Set on 2.5 beautiful acres, this inviting Cape-style home offers a wonderful combination of comfortable living space, character, and versatile outbuildings. The primary suite is conveniently located on the main level, with two additional bedrooms and a full bath upstairs. An attached two-car garage provides convenient parking and additional storage. The spacious living room features wide pine floors, built-in cabinetry, a fireplace, and a slider leading to the deck. The dining room continues the charm with wide pine flooring, a large window, and a built-in corner cabinet. Outside, the property offers a large barn with two stalls and an expansive workshop, along with two additional sheds for plenty of storage. There is also the possibility of restoring the property's former pond, adding another attractive feature to the landscape. The kitchen is ready for renovation, offering an opportunity to create a space tailored to your own style and needs. With 2.5 acres, a barn, workshop, attache

Nestled in a peaceful five acre setting just minutes from the shopping, dining, and everyday conveniences of both Bennington and Manchester, this beautifully maintained home offers privacy, comfort, and accessibility. Thoughtfully updated, this home offers a timeless, inviting style designed to feel welcoming for years to come. The newly renovated high end kitchen is both beautiful and functional, while two spacious primary en-suites provide exceptional flexibility and privacy. The first floor primary suite wing is a true retreat, featuring a luxurious bathroom with marble tile, frameless glass shower, double vanity and walk in closet. Upstairs, the brand new second primary ensuite offers an impressive private living area, spa like full bath, and generous closet space, perfect for guests, extended family, or a luxurious personal retreat. The inviting living room features a gas fireplace, creating a warm and comfortable space for relaxing and entertaining. The kitchen and dining area fl

Tucked away on a private road, this stunning brick colonial offers over 30 acres of peaceful Vermont countryside-yet is less than 2 miles from the Village of North Bennington and Bennington College. A classic barn and separate studio provide endless possibilities for hobbies, storage, or creative space. The main level features a spacious living room with a fireplace, warm pine floors, and plenty of room for a dining area. The kitchen is a cook's dream with cherry cabinets, a gas range, and a large island, plus a slider that opens to a pergola for outdoor dining and relaxation. A private office and half bath complete the first floor. Upstairs, beautiful pine floors continue throughout. The primary suite offers comfort and style, joined by two additional bedrooms and a full bath. From nearly every window, take in sweeping views of the surrounding landscape. A truly special property combining timeless charm with acreage, views, and versatile outbuildings-while still being just minutes fro

This Charming country home is currently being used as a primary home with a vacant 2nd in-law rental home. This property could be either a single family residence with/without an in-law house or as a 2 unit multifamily with 2 separate houses, This quiet country location has 2 homes located on its 2 acres. The main home is a 3 bedroom ranch featuring a large eat-in kitchen opening into a large living room. 3 bedrooms, including an addition with a large primary with 2 closets inlcuding one whick is a large walk-in closet. A large full bath with washer/dryer hookups completes the living area. The house has a partial concrete basement under the older portion, with a crawlspace under the addition. This main house needs some TLC including interior paint and could use new carpet and vinyl flooring. The smaller second house is located a few hundred feet from the main house and has its own separate driveway and a separate septic system (the 2 houses do share a common drilled well) This house fe

Nearly Lakefront Living in the Heart of North Bennington! Come for the space, stay for the location! This spacious home offers over 2,500 sq. ft. of living space, including 5 bedrooms, 3 full bathrooms, a large home office in the finished basement, and a versatile 250 sq. ft. bonus room attached to one of the upstairs bedrooms. The original garage has been thoughtfully transformed into a 600 sq. ft. primary suite, featuring energy-efficient mini-split heating and cooling, with a large main bedroom and an adjoining space ideal for a walk-in closet or private retreat. A new steel two-car garage was added, ensuring your vehicles stay protected year-round. The property's outdoor space is just as impressive with beautifully maintained perennial gardens (featuring lilacs, peonies, lilies, and phlox), fruit trees (peach and plum), and graceful white birches. A small backyard storage shed with electricity adds extra convenience. Located just steps from picturesque Lake Paran and nestled in the

Welcome to Hidden Ponds Farm - a breathtaking retreat set on 40 sprawling acres where history and refined country living meet in perfect harmony. This extraordinary early 1800s post-and-beam converted barn has been thoughtfully reimagined, preserving its authentic character while seamlessly integrating modern comforts. A magnificent 1,000-foot hand-placed stone wall winds gracefully across the landscape, framing two picturesque ponds and twin orchards that offer seasonal beauty and fresh harvests. The outdoor amenities elevate this property into a private resort: an inviting in-ground pool, hot tub, propane fire pit, and an impressive 90-foot deck with retractable awning, ideal for effortless entertaining and long summer evenings under the Vermont sky. For collectors, hobbyists, or outdoor enthusiasts, the property offers exceptional versatility. A detached four-bay garage with second-story loft provides abundant storage, while an additional outbuilding easily accommodates a large Clas

Tucked away in a private setting in Shaftsbury, this inviting home sits on 2.12 acres, offering both tranquility and convenience-just a short drive to both Manchester and Bennington. With 2,350 square feet of living space, the home features 3 bedrooms and 2.5 baths, thoughtfully designed for comfort and functionality. Many upgrades were completed in 2006, enhancing both efficiency and livability. The updated kitchen with granite couuntertops flows into an open dining and living area highlighted by soaring cathedral ceilings, creating a bright and airy atmosphere ideal for both everyday living and entertaining. A spacious family room provides additional gathering space, while the main-floor primary suite offers ease and privacy. An outdoor pellet furnace adds energy efficiency, complementing the home's practical upgrades. Attached to the rear of the home is an 18x24 workshop/storage area-perfect for hobbies, equipment, or additional workspace. Outside, enjoy a paved driveway leading to

Nestled in a peaceful five acre setting just minutes from the shopping, dining, and everyday conveniences of both Bennington and Manchester, this beautifully maintained home offers privacy, comfort, and accessibility. Thoughtfully updated, this home offers a timeless, inviting style designed to feel welcoming for years to come. The newly renovated high end kitchen is both beautiful and functional, while two spacious primary en-suites provide exceptional flexibility and privacy. The first floor primary suite wing is a true retreat, featuring a luxurious bathroom with marble tile, frameless glass shower, double vanity and walk in closet. Upstairs, the brand new second primary ensuite offers an impressive private living area, spa like full bath, and generous closet space, perfect for guests, extended family, or a luxurious personal retreat. The inviting living room features a gas fireplace, creating a warm and comfortable space for relaxing and entertaining. The kitchen and dining area fl

Stone Meadows a quintessential Vermont farmhouse set on more than 72 acres of rolling meadows, historic stone walls and peaceful countryside in Shaftsbury. Tucked along a quiet country road, this is the kind of property that captures the feeling so many people come to Vermont to find privacy, open land, character and and a home that feels connected to its surroundings. Serene and peaceful yet 17 minutes to Manchester. The farmhouse has been thoughtfully updated for today's living while retaining the architectural details and charm of its era. A brand-new kitchen with marble countertops is the heart of the home, complemented by spacious rooms, abundant natural light and a comfortable, inviting floor plan. Just off the kitchen, the screened porch offers the perfect place for morning coffee, summer dinners or simply taking in the quiet and beauty of the surrounding land. The living room, with its fireplace, provides a warm and welcoming place to gather. The updates continue behind the sce

The Dexter Road Farmhouse, Circa 1800 In 1922, poet laureate and Shaftsbury resident Robert Frost was inspired by the bucolic nearby backroads to write Stopping by the Woods on a Snowy Evening. Dating back more than 225 years, this charming farmhouse offers a rare opportunity to own a piece of Vermont history while embracing the slower pace and natural beauty that define the region. Tucked away at the end of a peaceful, tree-lined town road, the property is ideally suited as a second home, creative retreat, or year-round residence. Lovingly cared for by the same family for over 70 years, the home retains much of its original character and craftsmanship. Wide pine floors, original moldings, classic woodwork, traditional wall and ceiling boards, and a gracious entrance hall create a warm and authentic farmhouse atmosphere. Set on approximately 40 acres with a picturesque skating pond, the property offers abundant space to explore, garden, walk, and enjoy the pastoral surroundings. Writer

Tucked away on a private road, this stunning brick colonial offers over 30 acres of peaceful Vermont countryside-yet is less than 2 miles from the Village of North Bennington and Bennington College. A classic barn and separate studio provide endless possibilities for hobbies, storage, or creative space. The main level features a spacious living room with a fireplace, warm pine floors, and plenty of room for a dining area. The kitchen is a cook's dream with cherry cabinets, a gas range, and a large island, plus a slider that opens to a pergola for outdoor dining and relaxation. A private office and half bath complete the first floor. Upstairs, beautiful pine floors continue throughout. The primary suite offers comfort and style, joined by two additional bedrooms and a full bath. From nearly every window, take in sweeping views of the surrounding landscape. A truly special property combining timeless charm with acreage, views, and versatile outbuildings-while still being just minutes fro

Some homes simply have a way of making you slow down. Built in 1863, the original Twitchell Farmhouse is one of them. Rich in history and craftsmanship, this beautifully maintained four-bedroom, 2.5-bath home offers the warmth and authenticity that only a true Vermont farmhouse can provide. Original hardwood floors, handcrafted woodwork by a master carpenter, and thoughtful updates create a home that feels both timeless and comfortable. The country kitchen has been tastefully renovated while respecting the home's heritage, and the spacious primary bath features a generous double vanity with classic farmhouse styling. Whether it's curling up beside the fireplace on a snowy evening, enjoying a quiet morning in the bright enclosed sunroom, or unwinding on the private back yard surrounded by gardens, every space invites you to linger just a little longer. Outside, the property's agricultural roots remain proudly intact. The impressive tri-level hand-hewn and pegged barn, with silo, offers

Set privately on 25.34 acres, this 3BR/2BA contemporary-style home offers expansive views and a peaceful setting just 15 minutes from Bennington. Kitchen with breakfast nook opens out onto a back deck and the spacious living room features a cathedral ceiling and dramatic floor-to-ceiling fieldstone fireplace, creating an impressive focal point and inviting gathering space. First floor also includes a formal dining room and first floor bedroom or office as well as a full bath. On the second floor, the primary suite includes a large bathroom with a walk-in shower and tub, with a layout that may accommodate accessibility needs and a second guest bedroom includes a half bath. Basement-level 2-car garage provides workspace and a dedicated laundry area. The property offers a wonderful combination of privacy, acreage, and convenience, with plenty of room to enjoy nature and and the surrounding landscape. There is ample room for gardening and play! The home needs some repairs and updating, pro

Some homes simply have a way of making you slow down. Built in 1863, the original Twitchell Farmhouse is one of them. Rich in history and craftsmanship, this beautifully maintained four-bedroom, 2.5-bath home offers the warmth and authenticity that only a true Vermont farmhouse can provide. Original hardwood floors, handcrafted woodwork by a master carpenter, and thoughtful updates create a home that feels both timeless and comfortable. The country kitchen has been tastefully renovated while respecting the home's heritage, and the spacious primary bath features a generous double vanity with classic farmhouse styling. Whether it's curling up beside the fireplace on a snowy evening, enjoying a quiet morning in the bright enclosed sunroom, or unwinding on the private back yard surrounded by gardens, every space invites you to linger just a little longer. Outside, the property's agricultural roots remain proudly intact. The impressive tri-level hand-hewn and pegged barn, with silo, offers

Well designed and newer home on 10.085 acres in Shaftsbury, VT. Offering 3 bedrooms, including main level primary bedroom and 2 full bathrooms. Cathedral ceiling formal dining room and modern kitchen with dining area and breakfast bar. Large living room with vaulted ceiling and lots of light. Main level laundry and rear mudroom finish the first floor. Upstairs there is a wonderful loft area, 2 more bedrooms and a full bathroom. The basement is large and could possible have finished space. The outside is where this home truly shines. Great location, large sitting porch to watch the fauna. Rear deck for relaxing and large yard space. Large barn for either shop work or you could use it as a garage, as well as a storage shed. Short walk to the creek and lots of hiking trails

Vermont Home with Mountain, Meadow and Garden views Nestled in the Green Mountains of Vermont, this 3 bedroom 3 bath home offers scenic views, open spaces, and the tranquility of Vermont living. Situated on three separately surveyed lots, the beautifully maintained property features Heirloom apple trees, park like forests and lush perennial gardens bursting with color throughout the seasons and ample room to enjoy the outdoors. The property is conveniently located across from Lake Shaftsbury State Park ideal for hiking, swimming, fishing, making it an ideal year-round retreat with 5 Ski Resorts with in an hour drive. Inside, the thoughtfully designed home features an open-concept main floor centered around a cozy fireplace, creating a warm and inviting gathering space. A bright sunroom opens up to the second deck overlooking gardens and heirloom apple trees. Providing the perfect spot for relaxing, reading, or enjoying nature views. The finished basement offers additional living and en

Welcome to easy Vermont living in this beautifully maintained ranch-style home offering more than 2,000 finished square feet in one of North Bennington's most desirable neighborhoods. Set on a quiet cul-de-sac with lovely mountain views, Harvest Hills offers a wonderful sense of community, including a large neighborhood pond for residents to enjoy. The location is equally appealing; close to the village school, market, restaurants, and the popular Mile Around Woods trail. Inside, a spacious living room with a traditional brick fireplace flows into the bright, open dining and kitchen areas, creating an inviting layout for everyday living and entertaining. The charming kitchen features a breakfast bar, pantry, stainless steel appliances, and abundant natural light. Three comfortable bedrooms and two full baths include a primary bedroom with its own en suite bath. The finished lower level adds valuable flexibility with a generous family room, recreation space, or home office, complemented

Vermont Home with Mountain, Meadow and Garden views Nestled in the Green Mountains of Vermont, this 3 bedroom 3 bath home offers scenic views, open spaces, and the tranquility of Vermont living. Situated on three separately surveyed lots, the beautifully maintained property features Heirloom apple trees, park like forests and lush perennial gardens bursting with color throughout the seasons and ample room to enjoy the outdoors. The property is conveniently located across from Lake Shaftsbury State Park ideal for hiking, swimming, fishing, making it an ideal year-round retreat with 5 Ski Resorts with in an hour drive. Inside, the thoughtfully designed home features an open-concept main floor centered around a cozy fireplace, creating a warm and inviting gathering space. A bright sunroom opens up to the second deck overlooking gardens and heirloom apple trees. Providing the perfect spot for relaxing, reading, or enjoying nature views. The finished basement offers additional living and en

Nestled on 16.96 picturesque acres, this spacious 3-4 bedroom, 2 full bath home offers the perfect blend of privacy, comfort, and breathtaking Vermont scenery. Built in 1993, the home features a bright, open-concept great room with expansive windows that capture stunning views of the surrounding landscape. The inviting living area is anchored by a beautiful fireplace, creating a warm and welcoming space for relaxing or entertaining. The flexible floor plan provides three bedrooms plus an additional room that can easily serve as a fourth bedroom, home office, or hobby space. The walkout unfinished basement offers endless possibilities for future expansion, storage, or a workshop. Outside, you'll find an attached two-car garage along with a separate bonus garage, providing ample space for vehicles, recreational equipment, or additional storage. Set well back from the road, the property's 16.96 acres offer room to explore, garden, or simply enjoy the peace and beauty of Vermont. The home

Welcome to your paradise! This exquisite 30 acre estate offers extreme privacy, a custom home with architectural details throughout, a modern 1 BR guest apartment, an oversized 2 car garage, top notch equestrian facilities, a trout pond, playhouse and the list goes on and on. The winding driveway leads one to an enchanting compound, as it opens to overlook the exclusive estate in all of it's glory. The 3 Bedroom, 4000SF home boasts 10 foot ceilings, with reclaimed antique oak pocket doors from a nearby mansion, inlaid floors, stained glass windows, arches and a custom cherry and granite eat in island kitchen. The foyer, gracious leads to the expansive living room and kitchen overlooking the fantastic spring fed pond. there is a main level primary suite, and second floor gathering space with pond-side balcony and 2 bedrooms. The finished basement hosts a family recreation room and a sauna. Equestrian facilities are comprised of a recently built barn with 4, 12 X 12 stalls boasting Thuro

This Charming country home is currently being used as a primary home with a vacant 2nd in-law rental home. This property could be either a single family residence with/without an in-law house or as a 2 unit multifamily with 2 separate houses, This quiet country location has 2 homes located on its 2 acres. The main home is a 3 bedroom ranch featuring a large eat-in kitchen opening into a large living room. 3 bedrooms, including an addition with a large primary with 2 closets inlcuding one whick is a large walk-in closet. A large full bath with washer/dryer hookups completes the living area. The house has a partial concrete basement under the older portion, with a crawlspace under the addition. This main house needs some TLC including interior paint and could use new carpet and vinyl flooring. The smaller second house is located a few hundred feet from the main house and has its own separate driveway and a separate septic system (the 2 houses do share a common drilled well) This house fe