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Shaftsbury VT Real Estate

Located in the beautiful Bennington County of Vermont, hiking, local restaurants, and historic architecture are just a few of the wonderful things Shafstbury has to offer. Bordered by New York State, those in Shaftsbury enjoy a unique combination of a quiet, rural lifestyle with easy access to bigger cities. Shaftsbury's community shares an appreciation for culture and arts and is close by to Bennington College, home of the Robert Frost Stone Museum. 

Search the latest real estate in Shaftsbury, Vermont with Maple Sweet Real Estate. Find the right property for you from a variety of listings. ​Register to save your favorite listings and you can get email notifications when similar properties are posted. Have an account? Log in here.

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2167 Myers Road Shaftsbury VT 05262

Shaftsbury, VT2167 Myers Road

Price$1,995,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5014689

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3

Welcome to Hidden Ponds Farm!!! Nestled amidst 40 sprawling acres, this historic early 1800's post and beam converted barn is a rare gem combining rustic charm with modern comforts. The property is highlighted by a stunning 1,000-foot hand-placed stone wall, two picturesque ponds, and two orchards offering seasonal beauty and fresh fruit. The expansive outdoor space also features a hot tub, propane fire-pit and an in-ground pool perfect for summer relaxation, along with a 90 foot deck complete with retractable awnings for shaded outdoor gatherings. For those seeking ample storage or hobby space, the property includes a separate 4-bay garage with a second-story loft for additional storage needs. A pond and a pool pump house. Another outbuilding provides the perfect setup to house a large class A motor home or a boat, making this an ideal retreat for adventurers. In 1997, a striking post and beam great room addition was added to the home, showcasing a floor-to-ceiling stone fireplace as the room's centerpiece. The loft above offers a cozy perch, ideal for a reading nook or office space. Inside, you'll find a renovated kitchen, seamlessly blending modern appliances with the home's original character. With three spacious bedrooms and three updated bathrooms including one with a steam shower, this home offers comfort and privacy for family and guests alike. A rare blend of history, nature, and modern living, this property is truly one-of-a-kind.

Listed by Kelley McCarthy of Mahar McCarthy Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.79% last updated on 2024-11-07

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

5055 Vt Route 7a Shaftsbury VT 05262

Shaftsbury, VT5055 Vt Route 7a

Price$1,500,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5013489

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • 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

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.79% last updated on 2024-11-07

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

5055 Vt Route 7a Shaftsbury VT 05262

Shaftsbury, VT5055 Vt Route 7a

Price$1,500,000The price has recently decreased

MLS Number 5013220

  • Commercial
  • Year Built 1850
  • Square Feet 4,911
  • Acreage 5
  • Area Near Skiing, Rural

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

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.79% last updated on 2024-11-07

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1058 Granger Hollow Road Shaftsbury VT 05262

Shaftsbury, VT1058 Granger Hollow Road

Price$1,350,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5017874

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3

Rejuvenate your mind, body, and soul at your very own Vermont sanctuary. Over 40 acres of open meadows, rolling hills, fruit trees, berry bushes, stone walls, and a mature forest surround this sophisticated modern farmhouse. This is the perfect environment for buyers seeking privacy, beauty, and quiet broken only by birdsong. The owners spared no expense in developing this exceptional property. The house blends in perfectly with the land and has just been renovated to accommodate buyers with high standards and excellent taste. Its flooded with light, and each large Marvin window has a unique vista. Its fully custom kitchen cabinets with in-setdoors/drawers, worktable, marble countertops, Sub-Zero refrigerator, and Viking range will please any chef. A solid walnut countertop, bead board ceiling, and antique lighting accent the pantry. The large, light-filled master bedroom features a cathedral ceiling and offers spectacular views every season. Its bathroom features an exquisite marble floor, a bear-claw tub, and high-end fixtures. Two other bedrooms, a fully renovated bathroom, and a new laundry complete the second floor. This property offers a unique opportunity to the discriminating buyer. All measurements are approximate.

Listed by Carol O'Connor of Four Seasons Sotheby's Int'l Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.79% last updated on 2024-11-07

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1858 Trumbull Hill Road Shaftsbury VT 05262

Shaftsbury, VT1858 Trumbull Hill Road

Price$1,000,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5018303

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 4
  • Bathroom 3

Embrace the wisdom of Ralph Waldo Emerson: "Adopt the pace of nature. Her secret is patience." At Trumbull Hill, you'll discover over 60 acres of untouched Vermont beauty, perfect for those seeking tranquility and serenity. This custom-built timber-frame home is designed to showcase breathtaking panoramic views. Featuring four spacious bedrooms, this residence combines peace and privacy with thoughtful design elements. Large windows fill the space with natural light, while outdoor decks offer the perfect spot to stargaze and unwind. Inside, enjoy the warmth of a cozy wood stove, striking post-and-beam architecture, and inviting pine flooring. The open-concept kitchen flows seamlessly into the living areas, creating an ideal space for gatherings. With two and a half bathrooms, large kitchen, formal dining room, cozy living room, an oversized unfinished basement, and a sizable barn, this property has everything you need. The picturesque, tree-lined driveway adds to the charm. Don't miss your chance to experience this Vermont gem-schedule a visit today!

Listed by Faith Rhodes of Maple Leaf Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.79% last updated on 2024-11-07

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

1516 West Mountain Road Shaftsbury VT 05262

Shaftsbury, VT1516 West Mountain Road

Price$699,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5020098

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • 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

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.79% last updated on 2024-11-07

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

143 Cedar Circle Shaftsbury VT 05262

Shaftsbury, VT143 Cedar Circle

Price$595,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5009935

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4

Custom Built home and never before offered for sale in the lovely Hidden Valley of Shaftsbury, close to the lake and the farm fresh food stand and delicious chocolate barn. This spacious home boasts a recent addition custom built post and beam attached barn with a loft and full basement. The custom built stone fireplace in family room to the custom cherry cabinets in the kitchen will impress you. Full basement with den, bathroom and laundry and walks out to stamped concrete covered patio. Incredible storage in the dry basement and ask me about a cool surprise there. Off the back of the home, you can go on the deck from the living room or the foyer. There is an office with another room that also leads to the deck, this is a perfect space for a first floor bedroom or in law set up or home business office. Attached 2 car garage on the opposite side as the barn. Upstairs there are 4 bedroom spaces including primary with large bathroom and attach storage as well as 2 walk in closets. Paved driveway, beautifully landscaped with stonework and a frog pond, plus perennials galore and fruit trees and berry bushes, a hobby farmers dream! You will fall in love!

Listed by Lillian West of Maple Leaf Realty

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.79% last updated on 2024-11-07

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

196 Glastenview Drive Shaftsbury VT 05262

Shaftsbury, VT196 Glastenview Drive

Price$587,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5018699

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 5
  • Bathroom 2

Fully Renovated 4-5 bedroom 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

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.79% last updated on 2024-11-07

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

764 Myers Road Shaftsbury VT 05262

Shaftsbury, VT764 Myers Road

Price$499,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5012795

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2

Come see this Charming Cape in Serene Rural Setting … nestled among rolling meadows with mountain views. This picturesque home offers the perfect blend of rural charm and modern comfort. Step inside to discover a warm and inviting country kitchen, complete with a large island, perfect for casual meals or entertaining guests. The adjacent dining area is perfect for lazy family dinners. The large living room with fireplace and built-ins offer the perfect room to curl up with a good book or jig saw puzzle while watching the snow come down. Work in your private office or unwind in the out of the way den (a versatile space that can be tailored to your needs). The spacious primary bedroom offers a peaceful retreat, while an additional bedroom provides comfort for family or guests. With two full baths, mornings are a breeze. Outside, the expansive property invites you to explore the surrounding nature, whether it's a morning walk on this bucolic rural road greeting the early birds, expanding on the beautiful gardens or an evening spent under the stars at the fire pit toasting marshmallows. This home is more than just a place to live; it's a lifestyle waiting for you to come and put on your personal touches … being sold As Is .... All measurements are approximate.

Listed by Carol O'Connor of Four Seasons Sotheby's Int'l Realty

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.79% last updated on 2024-11-07

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

4799 Vt 7a Shaftsbury VT 05262

Shaftsbury, VT4799 Vt 7a

Price$475,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5006234

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2

So much to love, starting with the BRAND NEW SEPTIC! Sprawling 4 bed, 2 bath Ranch brimming with character PLUS two big outbuildings. Set back from 7A near Clearbrook Farm and The Chocolate Barn, close to Lake Shaftsbury. Just 12 mins to Bennington or 22 mins to Manchester. Formerly a hobby farm, wood shop, and mechanic's garage, these 3.3 acres are a sanctuary. One level house for comfort and convenience. From the covered porch you'll first enter the mudroom, with 3 bedrooms and full bath with laundry nearby. Custom Kitchen with butternut cabinets, live edge countertops, 3-bay commercial sink, Stainless Steel gas range and fridge. Dining + Living with soapstone woodstove and unique feature wall: the former barback from the Sirloin Saloon! Timberframe sunroom added in 1998: tile floor, cathedral ceiling, abundant natural light... your plants will thrive! Office with French doors and built-in desk is an accessible work-from-home space. Primary bedroom has built-in dresser and vaulted pine ceiling, and its own 3/4 bath with step-in tiled shower and Danby marble counter. Unfinished concrete basement has Buderus boiler, oil tank, 200 amps, and double-door exterior entry (great for storing firewood). Abundant spring water source! New roof in 2022. Enjoy the above-ground pool, gazebo, decks, and perennial gardens. Two-story barn (built 2014) and heated garage (1996) share a separate 200 amp service, plus there's a shed and coop. Ideal for a home-based business.

Listed by Jenifer Hoffman of Hoffman Real Estate

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4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.79% last updated on 2024-11-07

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

450 Cleveland Avenue Shaftsbury VT 05262

Shaftsbury, VT450 Cleveland Avenue

Price$289,900The price has recently decreased

Est. Mortgage: $/month

MLS Number 5021547

  • Residential Single Family
  • Full Bath 2
  • Village Shaftsbury
  • Construction Existing
  • Bedrooms 4

This charming Craftsman home located in beautiful Shaftsbury is just a short walk to the Post Office, the Shaftsbury Country Store and the Shaftsbury Elementary School! This quiet neighborhood offers peacefulness, and your private backyard boasts plenty of room for outdoor enjoyment and gardening. You can enjoy coffee in the mornings or your favorite beverage in the evening out on the covered porch. The first floor offers a spacious living room and dining room along with a kitchen, den and bedroom and a full bath. On the second floor you can have your choice of 3 bedrooms with a hallway bath to share. There's plenty of room to convert one of the bedrooms into an office space. The location of this home makes it very appealing to all being just 15 minutes to Bennington or Manchester. Come invision how this gorgeous house come become your home.

Listed by Floyd Amidon of Maple Leaf Realty

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.79% last updated on 2024-11-07

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

566 Vt Route 7a Shaftsbury VT 05262

Shaftsbury, VT566 Vt Route 7a

Price$280,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5014259

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2

Located on historic 7a in Shaftsbury, Vermont. House is listed as a 2 bedroom, but there is an office on the main floor should you need additional multi use space for guests. This property is ready for the next new owner to continue making the updates that have been started. Look at these beautiful, refinished hardwood floors! Don't miss an opportunity to own this solid home with large backyard, fenced in garden area, attached one car garage with additional separate detached two car garage for all your vehicles and toys! Situated on 6 acres of land, zoned for both commercial and residential use! Come take a look, don't let this one pass by you!

Listed by Julie Lowe of Lowe's Real Estate,LLC

{$office->Name}


4403 Main Street PO Box 703
Waitsfield VT, 05673
Office: 1.802.496.9800

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.79% last updated on 2024-11-07

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Broker Reciprocity 

Copyright 2024 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 November 12, 2024 9:53 PM EST

 

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