307 houses for sale in South Shaftsbury

Open House Sunday, 12-2. Set on over 5 picturesque acres in a peaceful country setting with beautiful Green Mountain views, this spacious 4 bedroom, 3 bath home offers the perfect blend of comfort, flexibility, and Vermont charm. Nestled just south of Manchester, the property provides an ideal balance of rural tranquility and convenient access to shopping, dining, recreation, and year-round attractions. Inside, you'll find generous living spaces designed to accommodate a variety of lifestyles, whether you're looking for room to gather and entertain guests, or create dedicated home office or hobby spaces. Large windows frame the surrounding landscape, bringing natural light and scenic views indoors. Some photos have been digitally staged. All measurements are approximate. Outside, the expansive acreage offers endless possibilities from gardening and recreation to simply enjoying the privacy and beauty of the countryside. Whether you're seeking a full-time residence, a Vermont retreat, o

Welcome to 89 Merson Street! This charming Cape style home offers 3 bedrooms, 1 full bathroom and a half bathroom, and nearly an acre of land on a quiet in town street. Inside, you'll find beautifully refinished hardwood floors, an updated kitchen, a spacious family room with a fireplace, and a new Weil-McLain boiler installed in February 2026. What truly sets this property apart is its incredible versatility. The bonus space presents endless possibilities for a home based business, professional office, hobby space, expanded living area, or potential in-law accommodations. Whether you're looking for room to grow, work from home, or create a space tailored to your lifestyle, this home offers the flexibility to make it happen. The generous lot and rear garage access provide additional opportunities for future improvements. Buyers may appreciate the potential to enhance accessibility and functionality with a redesigned driveway configuration, such as a circular drive, while maximizing the

This beautifully renovated 2-unit home by JDN Properties offers 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 residence with a luxurious upstairs primary suite and kitchenette, use it as an owner-occupied property with a rental unit to help offset your mortgage, or maximize rental income with separate 1-bedroom and 2-bedroom units, this property is designed to adapt to your lifestyle. Each unit is equipped with independent Utilities, ensuring privacy and convenience. The estimated monthly rental income ranges from $2,200 to $2,600, based on current market conditions. Located in a tranquil village neighborhood, within walking distance of downtown Bennington's vibrant shops and restaurants, and just two blocks from Southwestern Vermont Medical Center. The iconic Elm Street Market is close by, while Bennington College is only a short four-mile drive away. Recent ren

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

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

Offered as a peaceful Upstate retreat in the heart of Rensselaer County. Set within the scenic countryside of Hoosick Falls, this inviting property offers a rare opportunity to enjoy privacy, natural beauty, and small-town charm. Located in the quiet Mapletown area-one of the historic hamlets within the Town of Hoosick-this residence is surrounded by rolling hills, open skies, and the tranquil character that defines Upstate New York living.This home presents an ideal setting for a primary residence, weekend escape, or investment property. The surrounding landscape provides a sense of seclusion while still offering convenient access to nearby amenities, regional routes, and neighboring communities in both New York and Vermont.Hoosick Falls is a historic village of approximately 3,200 residents, known for its rich heritage and revitalized downtown district. Originally settled in the 1700s, the area grew around the Hoosic River, where early mills powered a thriving industrial communRefere

Offered as a peaceful Upstate retreat in the heart of Rensselaer County. Set within the scenic countryside of Hoosick Falls, this inviting property offers a rare opportunity to enjoy privacy, natural beauty, and small-town charm. Located in the quiet Mapletown areaone of the historic hamlets within the Town of Hoosickthis residence is surrounded by rolling hills, open skies, and the tranquil character that defines Upstate New York living.This home presents an ideal setting for a primary residence, weekend escape, or investment property. The surrounding landscape provides a sense of seclusion while still offering convenient access to nearby amenities, regional routes, and neighboring communities in both New York and Vermont.Hoosick Falls is a historic village of approximately 3,200 residents, known for its rich heritage and revitalized downtown district. Originally settled in the 1700s, the area grew around the Hoosic River, where early mills powered a thriving industrial community.Refe

Offered as a peaceful Upstate retreat in the heart of Rensselaer County. Set within the scenic countryside of Hoosick Falls, this inviting property offers a rare opportunity to enjoy privacy, natural beauty, and small-town charm. Located in the quiet Mapletown area-one of the historic hamlets within the Town of Hoosick-this residence is surrounded by rolling hills, open skies, and the tranquil character that defines Upstate New York living.This home presents an ideal setting for a primary residence, weekend escape, or investment property. The surrounding landscape provides a sense of seclusion while still offering convenient access to nearby amenities, regional routes, and neighboring communities in both New York and Vermont.Hoosick Falls is a historic village of approximately 3,200 residents, known for its rich heritage and revitalized downtown district. Originally settled in the 1700s, the area grew around the Hoosic River, where early mills powered a thriving industrial communRefere

Offered as a peaceful Upstate retreat in the heart of Rensselaer County. Set within the scenic countryside of Hoosick Falls, this inviting property offers a rare opportunity to enjoy privacy, natural beauty, and small-town charm. Located in the quiet Mapletown areaone of the historic hamlets within the Town of Hoosickthis residence is surrounded by rolling hills, open skies, and the tranquil character that defines Upstate New York living.This home presents an ideal setting for a primary residence, weekend escape, or investment property. The surrounding landscape provides a sense of seclusion while still offering convenient access to nearby amenities, regional routes, and neighboring communities in both New York and Vermont.Hoosick Falls is a historic village of approximately 3,200 residents, known for its rich heritage and revitalized downtown district. Originally settled in the 1700s, the area grew around the Hoosic River, where early mills powered a thriving industrial community.Refe

Offered as a peaceful Upstate retreat in the heart of Rensselaer County. Set within the scenic countryside of Hoosick Falls, this inviting property offers a rare opportunity to enjoy privacy, natural beauty, and small-town charm. Located in the quiet Mapletown areaone of the historic hamlets within the Town of Hoosickthis residence is surrounded by rolling hills, open skies, and the tranquil character that defines Upstate New York living.This home presents an ideal setting for a primary residence, weekend escape, or investment property. The surrounding landscape provides a sense of seclusion while still offering convenient access to nearby amenities, regional routes, and neighboring communities in both New York and Vermont.Hoosick Falls is a historic village of approximately 3,200 residents, known for its rich heritage and revitalized downtown district. Originally settled in the 1700s, the area grew around the Hoosic River, where early mills powered a thriving industrial community.Refe

Investment opportunities like this are few and far between! Located in a desirable mixed use district, this well maintained four unit one bedroom apartment building offers an excellent opportunity for both seasoned and first time investors. The property features four one bedroom apartments with full bathrooms, each with its own unique character and appeal. Two of the front/lower units have been thoughtfully renovated within the past five years and feature updated appliances, fresh paint throughout, and modern finishes. The two rear units are occupied by long term tenants who are happy to remain, providing immediate rental income and stability. Outside, you'll find a spacious yard, ample off street parking, and a convenient walkable location close to local amenities. Tenants are responsible for their own electricity and hot water, with each unit having its own dedicated hot water heater. The owner currently pays for heat, water, sewer, trash removal, snow removal, master insurance, and

This charming village home offers the perfect blend of tranquility and convenience. Situated on a spacious double lot, you'll enjoy plenty of room for outdoor activities and relaxation, all while listening to the soothing sounds of a nearby babbling brook. The home is well maintained and located at the edge of town, providing easy access to amenities yet offering a peaceful back deck. Featuring replacement windows for energy efficiency, a paved driveway, and ample yard space, this property is ideal for anyone seeking extra room to play and entertain. Sidewalks and streetlights make evening strolls safe and pleasant, and the proximity to downtown ensures you're close to shopping, dining, and public transportation. For outdoor enthusiasts, the location is unbeatable: just 10 minutes from Prospect Ski Area, 30 minutes to Mt. Snow, 45 minutes to Albany Airport, 3 hours to New York City or Boston, and 2 hours to Hartford. This home is ready for your finishing touches to make it truly your o

Your wait is over-an exceptional opportunity to own in the highly sought-after Woodford Lake Estates! This unique property offers direct access to the beauty of the surrounding Green Mountain National Forest and is ideally located near VAST snowmobile trails, making it a year-round haven for outdoor enthusiasts. Enjoy cross-country skiing just minutes away at Prospect Mountain, along with beach and boat rights to the lake. Set in a peaceful, nature-filled setting, this property is ready for your vision. The existing cottage requires significant foundation repair or replacement, presenting the perfect chance to restore the structure or start fresh and build your dream mountain lake retreat. A rare opportunity for investors, builders, or buyers looking to create something special in a truly desirable Vermont location. Being sold As-Is. This is a cash-only sale

A once-in-a-generation estate, this 125 acre property offers the rare combination that you almost never find: true privacy, two residences, forest trails, cultivated grounds, and river frontage on the Battenkill. Nestled at the base of Red Mountain on a private road, with the far shore protected by parkland, the property feels like its own secluded world while remaining minutes from Manchester dining, shopping, arts and recreation. A graceful connection to the landscape invites quiet moments, easy gatherings, and a deep appreciation of the extraordinary setting. The main residence is warm and thoughtfully designed, with a light-filled layout. River-reclaimed heart pine floors, new Andersen windows, central air, a wood-burning fireplace, and screened porches create a restorative Vermont retreat. Highly desirable one level living with a kitchen and dining with direct access to the garden, laundry room and walk-in pantry, powder room, library, and primary suite with French doors to the re

Approximately 10 years new, this well-maintained and recently refreshed home offers the perfect combination of modern construction and country charm in the Green Mountains. Set on 2.0+/- acres in Searsburg, Vermont, a one-lane dirt road separates you from thousands of acres of National Forest land to explore literally right outside your door. The lot offers plenty of mature plantings, a stonewall border, manageable yard and garden space, multiple outbuildings, and an adorable bonus cottage. Enter the main house through the screened-in porch, an excellent spot for morning coffee. Soak in the hot tub on the private back deck with your evening cocktail! Inside, find 1,302 square feet of living space with 2 bedrooms, 1.5 baths, open kitchen/dining/living with breakfast bar, coffee bar, and plenty of counter space. Offered mostly furnished, it is ready to enjoy from day one. Low-maintenance vinyl siding, architectural shingle roof, and gravel driveway. The property includes three versatile

Set on a 0.25-acre corner lot, this classic 4-bedroom home offers the space, character, and friendly atmosphere that make Elm Street so appealing. Sidewalks invite evening strolls and dog walks, neighbors gather on their porches, and it's a favorite destination for trick-or-treaters each Halloween. Next to the Elm Street Market, one block from Southwestern Vermont Medical Center, and close to downtown restaurants, theater, and parks, the location is exceptionally convenient while still feeling like a true residential neighborhood. Inside, generous rooms, abundant natural light, hardwood floors, wide moldings, and original architectural details give the home warmth and personality. The spacious living room offers flexibility for gathering, relaxing, or creating multiple seating areas, while the adjoining dining room provides an inviting setting for everyday meals and entertaining. The bright kitchen features abundant wood cabinetry, generous counter space, a farmhouse-style sink, gas ra

Build Your Dream Home-Without Starting From Scratch Now is your chance to own a brand-new home and still make it your own. This beautifully designed new construction home is currently underway and offers buyers the exciting opportunity to select their own finishing touches and create a space that reflects their style and vision. Featuring 4 bedrooms and 2 full bathrooms, this thoughtfully designed floor plan offers the flexibility and convenience of one-level living-with a bedroom, full bath, laundry, kitchen, dining area, and living room all located on the main level. Love the idea of extra space? The walkout basement provides incredible future potential and may be finished for an additional price-perfect for expanding living space, creating a family room, home office, gym, or guest suite. Enjoy all the benefits of energy-efficient new construction in a location close to walking trails, shopping, healthcare, and everything Bennington has to offer. ? New Construction ? 4 Bedrooms | 2 F

Welcome to this 3 bedroom, 1.5-bath Cape style home located in a planned commercial zone. Offering 1,688 square feet of well-designed living space on a manageable 0.26-acre lot, this inviting residence is perfect for comfortable family living. Offers beautiful hardwood floors gracing the upstairs bedrooms, as well as the spacious living and dining rooms-ideal for gathering with loved ones. The sunroom provides a bright and tranquil spot to relax or enjoy morning coffee, while the two-car garage ensures plenty of space for vehicles and storage

Welcome to this well-maintained, solid income-producing two-family home located in the heart of town-just steps from shops, dining, and downtown events. Perfect for owner-occupants or savvy investors, this property combines classic charm with modern efficiency and low operating costs. Each two-bedroom unit features spacious, light-filled living areas, eat-in kitchen and comfortable bedrooms. Recent energy-efficient upgrades include newer windows, oil tank, insulation, and high-efficiency heating system, helping to keep utility expenses low while enhancing year-round comfort. The property offers separate utilities, off-street parking, private outdoor space, and a strong rental history with consistent cash flow. Whether you're looking to live in one unit and rent the other or add a solid asset to your investment portfolio, this two-family checks all the boxes. Don't miss this rare opportunity for affordable in-town living with excellent long-term upside!

Set along tree-lined Monument Avenue in prestigious and historic Old Bennington, the Spargo House offers a rare opportunity to own a distinctive piece of Vermont history. Dating to circa 1800, this remarkable home was once the longtime residence of noted author, historian and collector John Spargo, founder and longtime director of the Bennington Museum. Just below the Bennington Battle Monument, the home blends historic character with thoughtful updates throughout its 2,692 square feet of living space. The bright kitchen features abundant cabinetry, generous counter space, stainless appliances and a center island, while exposed brick, arched openings and period details preserve the character of the home. Four bedrooms include an expansive primary suite with an exposed beam, sitting area, recently renovated bath and convenient in-suite laundry, while mini-split cooling adds modern comfort throughout the home. Outside, the deep one-acre lot stretches from Monument Avenue to Catamount Lan

You can make this home your own! With a little TLC, this charming 3 bedroom, 2 bath, Cape has the potential to become the perfect home. Featuring a large, level yard, a two-car, detached garage, with attached outdoor room, mudroom to the kitchen, wood floors, fireplace (condition unknown) and with this central location, it offers endless possibilities. Whether you are looking to renovate, personalize, or invest, this is a fantastic opportunity to create your vision. Close to downtown, schools, skiing, shopping and a short ride to Albany NY and Williamstown, MA. Next to most everything you will need

A rare opportunity to acquire one of Southern Vermont's most adaptable residential investment properties. Currently known as the South Shire Inn, this landmark Victorian estate offers investors immediate income potential along with exceptional opportunities for future residential or mixed-use redevelopment. The property includes nine guest accommodations, owner's quarters, expansive common areas, a detached carriage house with additional guest accommodations, a commercial kitchen, and an established Thai restaurant providing existing rental income. Its flexible floor plan and MU1 zoning support a variety of permitted residential and mixed-use possibilities, including multifamily conversion, long-term or short-term rentals, workforce housing, owner occupancy, senior living, residential care, and other redevelopment opportunities, subject to local approvals. Originally built in 1887 by renowned architect William C. Bull, the property has been thoughtfully restored while preserving its ar

Bright 3 bedroom, 1 and a half bath home in Bennington. Close to the hospital and offering kitchen, formal dining room, living room, and 2 main level bedrooms. Upstairs a loft office area and another bedroom. The basement is partially finished with laundry, family room and half bath. Outside there is a great deck with a separate, heated sun room and 2 car detached garage. A must see home in a must see location

Nestled in the scenic beauty of Clarksburg, this charming thirty acre farmhouse property offers endless potential and peaceful country living, Surrounded by rolling landscapes and natural beauty. The property includes a former barn on site that will have to be removed and a quaint chicken coop adds to the rustic charm and country feel, perfect for hobby farming or enjoying a simpilar lifestyle. Whether you're looking for a serene getaway, a homestead opportunity or property with room to grow, this unique Clarksburg property might be for you. Conveniently located near outdoor recreation, hiking and local amenities while still offering the tranquility of rural living

This is a farmhouse that is currently under construction. Selling as is, with the remaining materials included. It is off grid and was lived in up until last year. Construction started in November 2025. Large barn that used to be a dairy farm. House has 3 woodstoves for heat. 10 cords of wood are included. Very nice setting along side a beautiful brook. 16.5 acres of open and wooded land that is mostly level. The adjacent property of 279 acres is also listed by the owner. Call for pricing to purchase both. Blueprint and house plans are attached to show what the home would look like finished