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Shaftsbury Real Estate

Explore current real estate for sale in Shaftsbury, Vermont. If you have any questions or if you'd like to see any of these properties in person, call 802-793-2002 or contact us online.

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5055 Vt Route 7a Shaftsbury VT 05262

Shaftsbury, VT5055 Vt Route 7a

Price$1,500,000

MLS Number 5013220

  • Commercial
  • County Bennington
  • Square Feet 4,911
  • Acreage 5

RARE opportunity to become the third owner in nearly 50 years of the chocolate barn, a local landmark known for its commitment to high-quality ingredients and exceptional customer service. Fully turnkey with proven track records of success and growth provides fantastic opportunities for new ownership stepping in to continue the momentum. Strategically positioned along Historic Route 7a, the business attracts steady streams of locals and tourists year-round. Years of commitment results in premium products sold in-house retail and numerous high-profile wholesale accounts (restaurants, inns, country stores). Sale includes fully operational retail chocolate/ice-cream/gift shop. Known for high-quality offerings resulting in high-volume repeat customer base and strong online web order presence creating year-round steady cash flow. Opportunities to expand wholesale ice-cream sales, explore additional markets and/or increase offerings. Rare chance to acquire a successful, beloved business perfect for an entrepreneur looking to enter the food industry or expand their current portfolio. Owner-provided training with purchase. An 1842 Greek Revival farmhouse located on the property is included. Stunning home beautifully updated with original architectural features. This once-in-a-lifetime opportunity sits on +/- 5.0 acres of rolling lawns and old-growth sugar maples with quintessential panoramic views of The Green Mountains. NDA and buyer questionnaire required before showing.

Listed by Kristin Comeau and Elliott Nachwalter of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5055 Vt Route 7a Shaftsbury VT 05262

Shaftsbury, VT5055 Vt Route 7a

Price$1,500,000

Est. Mortgage: $/month

MLS Number 5013489

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 2

RARE Vermont Live & Work opportunity to become the third owner in nearly 50 years of the chocolate barn, a local landmark known for its commitment to high-quality ingredients and exceptional customer service. Fully turnkey with proven track records of success and growth provides fantastic opportunities for new ownership stepping in to continue the momentum. Strategically positioned along Historic Route 7a, the business attracts steady streams of locals and tourists year-round. Years of commitment results in premium products sold in-house retail and numerous high-profile wholesale accounts (restaurants, inns, country stores). Sale includes fully operational retail chocolate/ice-cream/gift shop. Known for high-quality offerings resulting in high-volume repeat customer base and strong online presence creating year-round steady cash flow. Opportunities to expand wholesale ice-cream sales, explore additional markets and/or increase offerings. Rare chance to acquire a successful, beloved business perfect for an entrepreneur looking to enter the food industry or expand current portfolio. Owner-provided training with purchase. An 1842 Greek Revival farmhouse located on the property is included. Stunning home beautifully updated with original architectural features. This once-in-a-lifetime opportunity sits on +/- 5.0 acres of rolling lawns and old-growth sugar maples with quintessential panoramic views of The Green Mountains. NDA and buyer questionnaire required before showing.

Listed by Kristin Comeau and Elliott Nachwalter of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1516 West Mountain Road Shaftsbury VT 05262

Shaftsbury, VT1516 West Mountain Road

Price$685,000

Est. Mortgage: $/month

MLS Number 5020098

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 3

Discover your dream retreat in this immaculate 3-bedroom, 3-bath, single level home, nestled on over 4 acres of breathtaking landscape. Enjoy expansive mountain views of the Taconic range, Bennington Monument, and Mount Graylock. Relax on the spacious deck or in the screened-in porch, soaking in the stunning vistas. This updated one-level home, features hardwood floors throughout and an open chef's kitchen equipped with a Viking gas range, granite countertops and custom cabinetry. Cozy up by the handsome wood-burning fireplace or the efficient pellet stove. With new insulation and updated windows, comfort and efficiency are prioritized. The fenced-in yard is ideal for outdoor entertaining, complete with a platform deck for grilling and ample space for your four-legged friends. Don't miss the unfinished dry basement and the attached two-car garage. This property offers a perfect blend of private modern living and natural beauty! Call today.

Listed by Margretta Fischer of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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196 Glastenview Drive Shaftsbury VT 05262

Shaftsbury, VT196 Glastenview Drive

Price$587,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5018699

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 2

Fully Renovated 4 bedroom plus office, Ranch-Rambler with stunning views. This home has undergone a complete transformation, featuring a reconfigured floor plan, new roof, siding, furnace, bathrooms, kitchen, flooring, deck, and landscaping. Enjoy open-concept living with a spacious kitchen, dining area, and living room that seamlessly flow together. Step outside onto the back deck for panoramic views that are truly breathtaking in every season. The lower level offers versatile living space perfect for additional living, guest areas, or even transforming into a primary bedroom suite. A bar area provides a great spot for gatherings, and the potential for a kitchenette adds even more flexibility if a separate living area is ever needed. This is an absolute must see.

Listed by Lori Hurley of Four Corner Properties LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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972 Vt Route 7a Shaftsbury VT 05262

Shaftsbury, VT972 Vt Route 7a

Price$550,000

MLS Number 5027649

  • Commercial
  • County Bennington
  • Acreage 0.15

MIXED USE INVESTMENT PROPERTY boasts two rental apartments and first floor retail space. The “Shaftsbury Country Store Building” on Historic Route 7A has stood the test of time. This landmark building dates back to 1850, when 10% of Vermont's population was destined to serve in the Union Army and fight in the Civil War. The back apartment is on the second and third floors with a large deck offering lovely mountain views. Three bedrooms, a spacious living room, a large eat-in kitchen, and plenty of extra space for your home office make this a most sought-after living space. The roomy front sunlit apartment has been recently updated and boasts three bedrooms with an open kitchen, dining, and living area. As a tenant, the thoroughly transformed Shaftsbury Country Store contributes to the rental income of this property. While this listing is for the real estate property, interested parties are encouraged to inquire for further details on opportunities tied to this unique retail location. We welcome your inquiry about this historic property...

Listed by Kristin Comeau and Elliott Nachwalter of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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972 Vt Route 7a Shaftsbury VT 05262

Shaftsbury, VT972 Vt Route 7a

Price$550,000

Est. Mortgage: $/month

MLS Number 5027950

  • Multifamily
  • County Bennington
  • Bathroom 2
  • Square Feet 5,878
  • Acreage 0.15

MIXED USE INVESTMENT PROPERTY boasts two rental apartments and first floor retail space. The “Shaftsbury Country Store Building” on Historic Route 7A has stood the test of time. This landmark building dates back to 1850, when 10% of Vermont's population was destined to serve in the Union Army and fight in the Civil War. The back apartment is on the second and third floors with a large deck offering lovely mountain views. Three bedrooms, a spacious living room, a large eat-in kitchen, and plenty of extra space for your home office make this a most sought-after living space. The roomy front sunlit apartment has been recently updated and boasts three bedrooms with an open kitchen, dining, and living area. As a tenant, the thoroughly transformed Shaftsbury Country Store contributes to the rental income of this property. While this listing is for the real estate property, interested parties are encouraged to inquire for further details on opportunities tied to this unique retail location. We welcome your inquiry about this historic property...

Listed by Kristin Comeau and Elliott Nachwalter of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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263 Elm Street Shaftsbury VT 05262

Shaftsbury, VT263 Elm Street

Price$439,000

Est. Mortgage: $/month

MLS Number 5028838

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 2

Fabulous Four Bedroom Farmhouse. Updated kitchen with new stainless steel appliances. Take in the mountain view through your newer windows over the new stainless steel sink and subway tile backsplash. Natural light floods this spacious home. The first-floor primary bedroom has a private walk-out deck overlooking the large level backyard. The generous living room opens up to a dining area just off the eat-in kitchen. The first floor laundry room, full bathroom, and a second bedroom round out the first floor. The second level features two additional bedrooms, a second bath and an office/ bonus space. Easy first-floor living and comfortable family flow. The full poured concrete basement with a new Buderus Boiler, 200 amp electrical service, and a spacious workshop. Enjoy newer windows, fresh paint, a metal roof, two generous decks and large storage shed all on a lovely corner lot. This home is located in Shaftsbury, bordering the Village of North Bennington so school choice may be an option. Don't miss out on this spacious home with mountain views, close to beautiful walking trails and all amenities. Such as restaurants, deli, library, Lake Paran's swimming and fishing, the Park -McCullough Historic Governor's Mansion with Farmer's Markets and so much more. Some photos have been digitally staged.Come discover the charming Village of North Bennington! Call today.

Listed by Margretta Fischer of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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296 Tinkham Road Shaftsbury VT 05262

Shaftsbury, VT296 Tinkham Road

Price$425,000

Est. Mortgage: $/month

Pending

MLS Number 5029437

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 3

At the base of West Mountain in a beautiful country setting on 3.68 acres with many undeveloped acres surrounding is this completely renovated cape cod style home. All new flooring throughout, all freshly painted interior and exterior with new front deck. New appliances and new primary bathroom, new laundry room with half bath, new full bathroom upstairs and Added a walk in closet to upstairs bedroom. Cozy living room with exposed beams and pellet stove. New wood stair case. New Exterior custom ordered black doors for front and back decks. Extensive landscaping including new gravel on driveway, removal of extensive brush and trees around the house and driveway. Above ground pool, shed, rock walls, 2 firepits front and back and 2 decks front and back, plus patio. Generator with brand new owned propane tank. Newer energy efficient Buderus boiler. Under house garage and walk out basement, ready for finishing for additional square footage. Hike through the woods and Enjoy the mountain views and quietness, star gazing and sunrises. Agent owned.

Listed by Lillian West of Maple Leaf Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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202 Cedar Circle Shaftsbury VT 05262

Shaftsbury, VT202 Cedar Circle

Price$330,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5029565

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 2

Private end of road Shaftsbury two level home built in 1985 with three bedrooms and two full bathrooms on three wooded acres, located on a quiet cul de sac. This home offers many fine features: air conditioning - wall unit, baseboard hot water heating system, supplementary pellet stove, attached two car garage, full roof replacement 2018, ceiling fans, formal dining room. The bright living room has an energy efficient Harman pellet stove, sliding glass doors to elevated balcony, formal dining room (12 x 11) seats eight comfortably, galley style kitchen with stainless appliances, plenty of cabinets for storage & direct access to large sun deck through sliding double glass doors. The remainder of the main level includes three good sized bedrooms, and a full bathroom. The bathroom has direct access from the primary suite, as well as the hallway, and has a double vanity sinks. The lower level has a nice size family room (25x15) with a cozy wood burning brick fireplace, second full bathroom, utilities room, and attached two car garage. The home is serviced by a drilled well with water softener and filtration, and a conventional septic system. The flooring is a combination of carpeting, tile, and vinyl. Outside has an inviting yard with paved driveway, large wood sun deck, and walking trails. The overall property appears to be in excellent condition, and awaits a new owner. We invite you to come take a look, as properties in this condition are in high demand, well worth your time.

Listed by David Halligan of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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0 Myers Road Shaftsbury VT 05262

Shaftsbury, VT0 Myers Road

Price$234,000

Est. Mortgage: $/month

MLS Number 5022242

  • Land
  • County Bennington
  • Square Feet 232,610
  • Acreage 5.34

Don't miss the opportunity to own a piece of Vermont paradise! This rare 5+ acre parcel offers the perfect combination of peace and natural beauty, making it the ideal spot for your future home, vacation retreat, or weekend getaway. Nestled on a quiet country road, the property boasts breathtaking mountain views that change with every season, from the lush greens of summer to the crisp, snow-capped peaks of winter. Whether you're relaxing by the pond, taking in the views from your deck, or enjoying the crisp winter air as the landscape transforms, this property offers a rare opportunity to immerse yourself in the majesty of the Green Mountain State year-round. The private pond is a true centerpiece of the property, offering both serenity and recreation. Dip your feet into the cool water, enjoy a quiet afternoon fishing, or ice skate on the pond, creating lasting memories and embracing the simplicity of country living. With over 5 acres of gently sloping land, there is ample space to build your dream home, create a hobby farm, or simply enjoy the open space. Whether you're planning a custom home, a seasonal retreat, or just a space to escape and explore, this land can accommodate it all. You'll enjoy the peace and serenity of rural life while being just a short drive to Bennington and Manchester for dining and shopping.

Listed by Angela Bevin of Maple Leaf Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2017 East Road Shaftsbury VT 05262

Shaftsbury, VT2017 East Road

Price$225,000

Est. Mortgage: $/month

MLS Number 5027108

  • Mobile
  • County Bennington
  • Bedrooms 3
  • Square Feet 1200
  • Acreage 1.49

3 bedroom 2 bath, double wide on 1.49 acres in Shaftsbury. Offering good location, large yard, and convenient travel to town. Living room with pellet stove, kitchen with modern appliances and dining area. Outside a 2 car detached garage, storage sheds and front and rear porches.

Listed by Max Squiers of KW Vermont - Brenda Jones Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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164 Laclair Road Shaftsbury VT 05262

Shaftsbury, VT164 Laclair Road

Price$209,900

Active With Contract

MLS Number 4765589

  • Commercial
  • County Bennington
  • Square Feet 21,600
  • Acreage 5.8

Rare opportunity to purchase a working horse farm with 21 stalls, indoor and outdoor riding arenas, 4 fenced training areas and so much more. The upper level of the barn could be made to suit many needs. Ample parking, stunning landscape and great horse country. Must see for anyone interested in equestrian arts. 5.8 acres. Potentially available as a lease for $2,000 per month.

Listed by Brenda Jones of KW Vermont - Brenda Jones Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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883 Vt Route 7a Shaftsbury VT 05262

Shaftsbury, VT883 Vt Route 7a

Price$199,000

Est. Mortgage: $/month

MLS Number 5005228

  • Residential Single Family
  • County Bennington
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 4

A classic Victorian home in the village of Shaftsbury is waiting for your imagination and perseverance to bring this once charming residence back to its original luster. Each room has its own character from dining room built-ins, shelving throughout the entire house to display your precious treasures, living room fireplace for those cozy winter nights, exposed brick and extra large eat-in kitchen. There are four bedrooms on the second floor, one is an office. The back entrance brings you into a very spacious mudroom, always a plus for Vermont's ever changing seasons. A stairway that leads to the cellar from the back entrance was once an apartment with a kitchenette and full bathroom.There are two sources of heat, an oil furnace and a wood furnace. The grounds need some reshaping and in-ground pool could be a plus for the hot summer days and entertaining. Sidewalks for safe walking, close to the post office, Shaftsbury Elementary School and the Shaftsbury Country Store. Easy drive to shopping and restaurants in either Bennington, or Manchester. Three hours to NYC and Boston, one hour to Albany International airport for travel. Come and take a look, I'd love to show you! House is being sold "as is."

Listed by Monique Geannelis of Mahar McCarthy Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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0 Glastenbury Road Shaftsbury VT 05262

Shaftsbury, VT0 Glastenbury Road

Price$75,000

Est. Mortgage: $/month

MLS Number 5017901

  • Land
  • County Bennington
  • Square Feet 448,668
  • Acreage 10.3

Find your Vermont getaway. 10.30 acres in Shaftsbury, VT. At the end of the publicly maintained Glastenbury Road sits this gorgeous piece of property. Mostly wooded but ready for your getaway. This area has scattered logging roads, camps, cabins and is perfect for the outdoorsman. Currently camp/cabin only changing this requires petition signed by 5% of voters and then a Town Meeting vote.

Listed by Max Squiers of KW Vermont - Brenda Jones Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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0 Vt Route 7a Shaftsbury VT 05262

Shaftsbury, VT0 Vt Route 7a

Price$50,000

Est. Mortgage: $/month

Pending

MLS Number 5029626

  • Land
  • County Bennington
  • Square Feet 130,680
  • Acreage 3

Secluded 3 acre parcel in the woods, set far back from VT 7A. Deeded Right of Way (ROW) guarantees permanent access by vehicle or on foot. ROW is shared with adjacent land owners (some have hunting camps) and has always been used seasonally, so it's not plowed. Prospective buyers are welcome to snowshoe or hike in along the ROW until the snow melts and road becomes usable. Road is mostly level and this parcel slopes gently uphill. Spectacular mountain views to the east (sunrise). Suitable for recreation or residential development. R-80 zoning has 2 acre minimum so it cannot be further subdivided. Seller has not done perk testing; state permit for private well and wastewater would be needed for a residential building permit.

Listed by Jenifer Hoffman of Hoffman Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Glastenbury Road Shaftsbury VT 05262

Shaftsbury, VTGlastenbury Road

Price$49,000

Est. Mortgage: $/month

MLS Number 5019171

  • Land
  • County Bennington
  • Square Feet 361,548
  • Acreage 8.3

Wooded lot on Shaftsbury / Glastenbury line.

Listed by Chrissy Carroccio of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Mar 13, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated March 19, 2025 11:24 AM EDT