307 houses for sale in South Shaftsbury

Rehabbers rejoice! This 4-bedroom lakehouse has been in the family since it was built in the late 1980s, and is now available on the cheap for you to restore and enjoy! A short stroll from Big Pond and backing up to a tremendous amount of National Forest, this property puts you near the water for summer enjoyment and near VAST trails for the winter. Enjoy the amenities of neighboring Bennington and then come back to the solace of the woods. Foundation needs serious repair or replacement. 3 bedrooms upstairs along the balcony and one downstairs by the kitchen and living room. Inquire today!

Located just minutes from the slopes of Mount Snow, the pristine waters of Lake Raponda, and the expansive Harriman Reservoir, this property offers the ideal combination of convenience, recreation, and opportunity. With ample space and zoning flexibility, you have the unique chance to build an Accessory Dwelling Unit (ADU) on-site, perfect for generating rental income, hosting guests, or creating a private retreat. Whether you're a winter sports enthusiast, a lover of water activities like kayaking, paddleboarding, and fishing, or simply seeking a peaceful escape, this location is a gateway to year-round adventure. Explore skiing and snowboarding, hike and bike scenic trails, or enjoy the vibrant local food and arts scene in nearby downtown Wilmington. Imagine the possibilities: your dream home, an income-producing property, or a combination of both, all in a setting that perfectly captures the beauty and charm of Vermont

Roll up your sleeves! This property needs complete rehab but will be well worth the effort. Private location set back from the road, large yard ready to enjoy. Short drive to North Adams for shopping. Don't hesitate to take a look this may be the one for you

This well maintained 2-unit home exceptional flexibility for buyers, allowing for a variety of living arrangements to suit your needs. Whether you choose to enjoy it as a spacious two-story single family. use it as an owner-occupied property with a rental unit to help offset your mortgage, or maximize rental income with separate 2-bedroom and 3-bedroom units, this property is designed to adapt to your lifestyle. Each unit is equipped with independent Utilities, ensuring privacy and convenience. Located village neighborhood, a short distance from The Bennington Bike path, the Bennington are trail system and downtown Bennington's vibrant shops and restaurants, and Southwestern Vermont Medical Center. 15 minutes to Prosepct Ski area 30 minutes to Mt Snow 1 hour to Albany Airport, Boston. Manhatten and Hartford are all within 3 hours

Welcome home to this meticulously maintained 3 bedroom, 1.5 bath ranch, perfectly nestled in a highly desirable neighborhood. Offering over 1,400 square feet of single level living space, this home combines classic charm, everyday comfort, and an unbeatable location. Rich hardwood floors flow throughout most of the home creating a warm and inviting atmosphere from the moment you step inside. The spacious layout offers comfortable living areas filled with natural light, generous-sized bedrooms, and a floor plan designed for effortless everyday living and easy entertaining. A charming breezeway connects the home to the attached one-car garage, providing a practical transition space that's perfect in every season while adding timeless New England character. Outside, the yard offers room to garden, play, or simply relax and enjoy the peaceful surroundings. Location is everything, and this home delivers. Tucked into an established neighborhood known for its welcoming feel, you'll be just mi

Experience refined living in this beautifully appointed tri-level townhouse-style condominium, ideally situated just moments from downtown, the hospital, shopping, and dining. Rich in vintage character while thoughtfully updated for modern living, this exceptional residence showcases elegant quartz and butcher block countertops, a designer tile backsplash, and striking marble flooring that create a sophisticated culinary space. An updated powder room and engineered hardwood flooring throughout further enhance the home's timeless appeal. The second level offers three well-appointed bedrooms and a tastefully renovated full bath designed with both style and comfort in mind. A walk-up attic provides abundant storage, while the partially finished lower level expands the living space with a dedicated laundry area, a versatile bonus room ideal for a home office, fitness studio, or media room, and a utility room featuring a newer heating system (2020), oil tank (2022), and upgraded 200-amp ele

Welcome to Peaceful Pines, your cottage in the woods near the entrance to the Green Mountain National Forest. The charming two-bedroom cottage/camp was lovingly maintained. Key updates include a completely rebuilt chimney and masonry work, a wood stove ( in addition to baseboard heat) to take the chill out of those fall and winter evenings, T11 siding, a newer roof, and a private back deck with potential views of Glastonbury Mountain and beyond. The property also features an outdoor shower, a large shed, a drilled well, and a concrete block foundation. The lot offers plenty of space for outdoor activities and relaxation on +/-.8 acres. Inside, the cozy living room is open to the kitchen and a large family room addition, providing a comfortable and inviting living space. Priced at $159,000, this property is an excellent way to break into the seasonal home market or pick up an affordable getaway in the Green Mountains. Peaceful Pines is conveniently located less than 10 minutes from Benn

Well-maintained two-family home offering spacious units, each featuring 2 bedrooms, a cozy kitchen, dining room, living room, full bath, and convenient in-unit washer and dryer hookups. Enjoy relaxing on the inviting covered front porch or the private covered back decks for each unit. Situated on a level half-acre lot, this property also includes off-street parking with a driveway and a 2-car garage. Ideally located just minutes from downtown shops, restaurants, and nightlife. A fantastic opportunity for owner-occupants or investors alike!

Thoughtfully crafted with a distinctive European-inspired character and beautifully updated throughout, this custom-built 4-bedroom, 3-bath home offers the perfect blend of quality craftsmanship, privacy, and convenience on a picturesque, landscaped lot just minutes from downtown Bennington. The bright and inviting interior features a beautifully renovated kitchen, spacious living areas with hardwood floors, and a stunning primary suite featuring a custom walk-in closet and a spa-inspired bath with heated tile floors. Offering exceptional flexibility, two of the four bedrooms are currently configured as home offices, while the versatile floor plan easily adapts to a variety of lifestyles. The bonus room includes plumbing for a future kitchenette, creating excellent potential for an in-law suite or multi-generational living. Step outside to enjoy the expansive deck, impressive stone patio, terraced gardens, and peaceful outdoor spaces designed for relaxing or entertaining. The detached

Set on 3.11 peaceful acres with mountain views and a wonderful sense of privacy, 193 Finley Drive offers the rare combination of one-floor living, generous finished space, and excellent garage capacity in a convenient Bennington location. This 2-bed/3-bath home features a thoughtful main-level layout, with each bedroom offering direct access to a 3/4 bathroom. The primary bath also includes laundry, creating true one-floor convenience. Main living spaces are warm, bright, and inviting, with hardwood floors, bay windows, abundant natural light, and a distinctive two-sided brick fireplace with gas insert anchoring both the living and dining rooms. Built-in shelving adds character and function, while the easy flow between rooms makes the home comfortable for everyday living and welcoming for guests. The galley kitchen sits at the center of the home, with space for a breakfast table and direct access to the large deck. Big picture windows frame the surrounding greenery and mountain view, b

Six oversized garage bays across two multi-level outbuildings, direct access to Green Mountain National Forest, backyard waterfalls, and 5.4 private acres make this gated Southern Vermont retreat unlike anything else near Wilmington. Just five miles from downtown Wilmington and less than 12 miles from Mount Snow, the property combines substantial space for living and entertaining with exceptional room for vehicles, boats, equipment, collections, creative pursuits, and outdoor recreation. The multi-level outbuildings expand the possibilities well beyond vehicle storage, with flexible finished and unfinished areas suitable for recreation, hobbies, collections, equipment, workshop use, or additional gathering space. Inside, post-and-beam warmth, hardwood floors, neutral finishes, a spacious kitchen with a large center island, updated baths with custom tile, and two oversized stone fireplaces create an inviting Vermont atmosphere. A private primary suite wing offers a well-appointed bath,

Uncommonly Superb View - A Vermont Meadow Retreat Tucked quietly into a broad meadow and surrounded by lush Vermont landscape, this property enjoys one of those rare, completely unspoiled western vistas: a full, harmonious sweep of the Taconic Mountain ridgeline, framed perfectly within human scale. The almost 40 acre setting-meadow bordered by deep woodland-creates a sense of arrival, privacy, and permanence that is difficult to replicate. The architect designed home blends natural materials inside and out, offering a calming, organic environment that feels inseparable from the land around it. One of the sellers' guiding goals the architect skillfully interpreted, was harmony with the landscape, expressed most beautifully in the roofline: a broad expanse of split shake cedar shingles that subtly echoes the rolling contours of the surrounding mountains, allowing the home to settle into the meadow as though it has always belonged there. After watching the setting sun from the screened p

Blending vintage charm with modern updates, this beautifully refreshed 3-bedroom, 2-bath home offers comfortable in-town living close to local amenities. Recent improvements include a newer roof installed just three years ago and new flooring throughout, creating a fresh and inviting atmosphere. Other additions include new kitchen appliances, furnace, and heat pump hybrid water heater, making the home incredibly efficient. The bright, open, kitchen is filled with natural light and features a sliding door leading directly to the private brick patio, perfect for outdoor dining, entertaining, or relaxing. A covered front entrance adds welcoming curb appeal, while the enclosed porch provides excellent potential as a practical mudroom entry. Upstairs, you'll find generous attic space offering abundant storage possibilities. Outside, the backyard is enhanced by a charming newly added shed complete with a screened-in section, creating an ideal retreat for hobbies, gardening, or enjoying warm

Versatile mixed-use property with strong potential as a duplex or owner-occupied investment in a highly visible downtown North Street location. Currently configured with a beautifully renovated 1-bedroom, 1-bath apartment on the second floor and a spacious first-floor commercial unit, this property offers multiple paths for income and future use. Zoning supports multi-family, single-family, and a wide range of commercial uses including retail, food and beverage, office, studio, and personal services. The second-floor apartment, renovated by a prior owner approximately 10 years ago, provides comfortable living space ideal for an owner-occupant or steady rental income. The first floor and basement, formerly home to a long-standing florist shop, now offer a bright, open layout with the removal of the walk-in cooler, making the space feel larger and more adaptable than ever. Recent updates include fresh paint, new flooring, LED lighting, and a convenient half bath. For investors or those s

MOVE RIGHT IN AND MAKE YOURSELF AT HOME This beautifully maintained residence is perfect for those looking for the convenience of first floor living. Featuring tastefully painted rooms, bamboo flooring and modern appliances. The kitchen includes a dedicated eating area for family dining while the living room offers a warm and cozy gathering space. Both bedrooms are generously sized with large closets and a full bath, plus a dedicated laundry area, all conveniently located on one level. The large, finished basement provides additional space, ideal for a home office, guest area or hobbies. The attached garage ensures easy access and the back deck offers a peaceful spot to relax while enjoying the soothing sounds of the Roaring Branch river. Situated in a quiet, friendly neighborhood. This house is a wonderful place to settle in and enjoy life

Opportunity is knocking. answer the door! This home in a sought-after neighborhood on an almost half acre lot is the investment you've been looking for. Close to downtown shopping and dining, as well as the award-winning Southwestern Vermont Medical Center. Features include an attached two car garage, wood floors, mini-split in living room, fireplace, wood floors, dining room, primary bedroom with ensuite 3/4 bathroom, deck, and more. All four bedrooms and two bathrooms are on one level. The walk-out basement was once partially finished and could be plenty of extra living space. Come bring this property back to life! Offered well below appraised value

Luxury Timber Frame Estate on 52+ Acres in Southern Vermont. This exceptional custom post-and-beam retreat is privately set amid rolling hardwood forestland, offering expansive mountain views, remarkable privacy, and a rare sense of peace and connection to nature. Designed for both elegance and efficiency, the home features solar panels with two Tesla Powerwalls for optional off-grid independence, paired with energy-efficient mini-split systems providing low-cost heating and air conditioning throughout the seasons. The residence offers three bedrooms and three baths, two versatile lofts, bonus room, gym and a spacious attached two-car heated and insulated garage, complemented by a flexible office, studio, or guest space above-perfect for today's work-from-home lifestyle, supported by high-speed internet in a truly serene setting. A newly designed chef's kitchen with premium appliances flows effortlessly into refined living spaces anchored by a Vermont stone fireplace, blending warmth,

Perched above the Battenkill River Valley and surrounded by mountain views this two story Vermont Gem is waiting for you. The perfect size two bedrooms, two bath home offers maple hardwood flooring, oversized windows and soaring mountain views. Lovely perennial gardens, flowering apple trees and large meadows grace the 3.90 acre property. This thoughtfully constructed home was built in 2000 with meticulous details, including; crown molding, built-in bookshelves, solid wood pocket doors and large closets are just a snipit of the construction. The soapstone wood stove and attached garage offer convenience and practical living. Don't miss the large, heated, unfinished basement with high ceilings an additional 700 sqft. The front porch and back patio offer a nice mix of outside living. The second meadow parcel would make a fabulous garden or horse pasture. Fishing, Swimming and floating on the Battenkill River, The picturesque West Arlington Covered Bridge and Wayside Country Store are jus

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

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

Have you dreamed of a home on a quiet cul-de-sac with over an acre of land and seasonal mountain views? Look no further! Situated on a wooded lot in a very desirable neighborhood, this spacious home has all you need. Flooded with natural light, the large living room includes a gas fireplace, cozy reading nook, and cute sunroom that is perfect for plants. It leads to a wraparound deck, also accessible from the formal dining room. The kitchen has plenty of counter and storage space. Some rooms have hand-painted touches done by a local artist - adding to the uniqueness and charm of the home. A dedicated laundry room with double closets is convenient. Rounding out the first floor are two bedrooms, including a primary with ample closet space and a massive en suite bathroom complete with a bidet and whirlpool tub. Upstairs you will find an additional bedroom with enough space to convert to two separate rooms. A deep heated garage with entrance to the huge dry basement (with high enough ceili

Extensively Renovated Classic Vermont ColonialThis beautifully updated 1935 Vermont Colonial offers the perfect blend of classic charm and modern convenience, with thoughtful additions completed in 1972 and 2016. With nearly 3, 900 square feet of living space, this spacious home features 4 bedrooms, 4.5 bathrooms, two dedicated office spaces, and a versatile third-story bonus room, ideal for a playroom, studio, or guest space.The large kitchen is the heart of the home, featuring a generous center island perfect for casual dining, cooking, or entertaining. Adjacent to the kitchen is a spacious dining area, ideal for hosting large gatherings. The family room offers a cozy yet airy atmosphere with its vaulted ceiling and a slider leading to a private back deck, perfect for relaxing or entertaining outdoors.A large mudroom entry provides a practical and welcoming space before entering the main living area. The main-level primary suite offers potential for a separate in-law suite setup, wit

Got a toolbelt, a dangerous amount of Pinterest boards, and an active imagination? It's your time to shine! Tucked away on 3.52 blissfully serene, wooded acres in beautiful Sandgate, this rural retreat is the dictionary definition of a diamond in the rough just waiting for your grand vision! Born in 1983 and being sold as-is, this ranch has fantastic bones. The main house is completely liveable right now, sporting 2 bedrooms (plus a bonus room!) and 1 full bath. Vaulted ceilings, exposed beams, and a massive stone fireplace deliver that quintessential, cozy Vermont vibe. The kitchen already rocks an island and stainless steel appliances. All it needs is your culinary genius and a few finishing touches. And fear not, digital nomads: high-speed fiber optic internet is available, so you can stream DIY tutorials (or just binge-watch Netflix while ignoring your to-do list) without a hitch. Now for the awesome part: The property includes a second structure that used to be a dentist's office!

Freshly Updated Vermont Home with Mountain Views and Battenkill River Access Move right in and enjoy the many recent upgrades, including a brand-new roof, mini-splits for AC and heat, fresh interior paint, new stainless steel appliances, and a beautifully renovated first-floor bathroom with radiant heated floors. This warm and welcoming 4-bedroom, 2-bath home offers comfortable living spaces with plenty of room to gather, relax, and entertain. The fresh updates give the home a bright, clean feel while still keeping its Vermont charm. Whether you're hosting family and friends or enjoying a quiet weekend away, the layout works beautifully for everyday living. The spacious insulated basement and attached two-car garage adds convenience and extra storage for all your gear. Step outside and take in the mountain views, peaceful setting, and easy access to the Battenkill River. This stretch of the river is known for being one of the widest and deepest nearby-perfect for fishing, kayaking, swi

Beautifully maintained split-level home offering a wonderful combination of comfort, flexibility, and privacy! Situated on a large, one-acre private lot, the property features a circular driveway and loose-laid rock wall that frames the landscape with classic rural charm. The main level boasts an open-concept layout with gleaming hardwood floors throughout, a spacious living room, and a kitchen with Corian countertops. Two generously sized bedrooms benefit from a thoughtful addition/expansion, including a primary bedroom with slider access to the back deck. A full bath w/ a jetted bathtub and first floor laundry. Enjoy your bright sunroom, which features vaulted ceilings, recessed lighting, a propane stove, and a slider leading to an oversized deck. This space provides the perfect setting to relax and entertain while overlooking the private backyard with a serene Vermont atmosphere. The finished lower level is ideal for extended family or in-law living, featuring an open kitchen/living