Historic & Antique Homes

This search features single-family homes built before 1945. Properties are listed by price in order from high to low. You may change your sort order below, and you can refine your search by checking or unchecking the search criteria (or sliding the criteria bar) along the right side of this page.

1284 Upper Hollow Road Dorset VT 05251

Dorset, VT1284 Upper Hollow Road

Price$1,175,000

Est. Mortgage: $/month

MLS Number 4806732

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3,938

Offered for the first time in 65 years take the park like drive on Upper Hollow to 1284 at its pinnacle, this historic Vermont hill farm is ideally situated to provide 360 degree views of the mountains forming the Dorset Hollow. Mature plantings shield the property from the road with open rolling meadows all around. Originally built in 1855, total rebuild in 1955 and there's a circa 2000 addition creating a main level vaulted & beamed ceiling primary suite, two walk-in closets, south west facing morning room, walk out substantial guest quarters or in-law space below. The L-shaped living / dining room has numerous windows providing views and light, wood floors, exposed beams and a central wood burning fireplace. The corner eat-in kitchen is open and light-filled with plentiful cabinetry and access to all living areas, a sunny deck and fenced in side yard. Exposed ceiling beams, two walk-in closets, wood floor and a white tile bath comprise the master. Upstairs there are two additional spacious bedrooms, one with wood burning fireplace and loaded with architectural detail. Antique wide pine floor, light, views and a third tile bath complete this floor. 1020 sqft detached garage. 25 pastoral acres that shall service agriculture, equine or the animals desired! Private Retreat, family compound or develop as the property offers long road frontage of tremendous quality open land!!! A sanctuary that self sustains!!!

Listed by Laura Beckwith of Josiah Allen Real Estate, Manchester Branch Office

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$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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389 Cobble Hill Road Londonderry VT 05148

Londonderry, VT389 Cobble Hill Road

Price$999,500

Est. Mortgage: $/month

MLS Number 4763028

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 3,227

In the heart of the desirable Mountain towns of Vermont, Cobble Hill Farm offers complete privacy and stunning views of Glebe Mountain. The farm is sited at the end of a dirt road on 149 acres with ancient stone walls that crisscross the land, a spring-fed pond and trails throughout the property. The residence is a c1790s Noah's Ark design, a style of Cape architecture unique to the area. The addition includes a magnificent great room with a 15 ft. ceiling and a floor-to-ceiling stone fireplace. The farmhouse is 3,227 square feet in estate-condition and was last renovated about 25 years ago. There are highly skilled design/builders in the area who have a sensitivity to historic homes and the requirements of 21st century families. The house has good bones and all the elements to support the value - end of the road privacy, views, historic house and a very convenient location. The trails connect into a 32 km network of trails run by the Viking Nordic Center and the location is within walking distance to Lowell Lake. Cobble Hill Farm is 2.8 miles from the center of Londonderry, 8 miles from the nationally renowned Weston Playhouse, 10 miles from Bromley, 17 miles from Stratton and 19 miles from Manchester.

Listed by Dia Jenks and T Story Jenks of LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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310 Dale Road Weston VT 05161

Weston, VT310 Dale Road

Price$995,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4762534

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 3,790

Built in 1830, this Noah's Ark style farmhouse on a quiet road has awe-inspiring mountain views south to Glebe Mountain and Stratton and overlooks a large, clear swimming pond. Located just outside the village of Weston, Quill Hill is a house with soul and charm and loveliness. There are stone walls, fragrant lilacs and perennial beds that bloom all summer. The 3,790-square-foot home was renovated by R.H. Adams whose work on historic homes in the area is legendary. This is a comfortable house with architectural detail, wide pine floors, original doors and exposed hand hewn beams. The well-appointed kitchen with its Dynasty gas stove, Sub-Zero refrigerator and Bosch dishwasher, opens to a sitting area. The main level includes the living room with windows on three sides and a reading room-both with fireplaces; a dining room; and a screened porch, which looks out to expansive views. Completing the first floor is the master bedroom wing with a fireplace. On the second floor there are 4 bedrooms and a large space to be used as an office, studio or for yoga. 12 miles to Bromley, 17 miles to Stratton, and 4.4 miles to Viking Nordic Center. It is under 3 hours to Boston, and less than 4 hours to New York.

Listed by Dia Jenks and T Story Jenks of LandVest, Inc/Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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108 Church Street Dorset VT 05251

Dorset, VT108 Church Street

Price$775,000

Est. Mortgage: $/month

MLS Number 4722827

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 6
  • Square Feet 4,110

Built in 1905, The Musser House exudes all the charm & character that one would expect from a Dorset Village property. Located on the Green next door to the Dorset Field club, you can walk to the historic Dorset Inn, the Dorset Union Store, or the Dorset Playhouse. A covered front porch is the perfect place to gather with family and friends or relax solo & watch the quiet happenings of a quintessential VT village. Recently renovated, it was updated to meet the needs of the modern homeowner while maintaining the historic character of the home's age- slate roof, hardwood floors throughout, hearty moldings & wood details, & clawfoot tubs, among other details. The front living room is perfect for warming up in front of a wood burning fire or wander out to the screened in porch in the rear of the house. The dining room with corner hutches is great for entertaining. A kitchen with plenty of storage & marble counter space & updated appliances really feels like the epicenter of the home. At the back of the house is a family room & casual dining area with access to a deck or a mudroom entry. A detached two-car garage is out back. Perfect for hide-and-seek, there are two staircases leading to the second floor, which offers five spacious bedrooms and closets to boot and three baths. A third floor is perfect for a media space, office or guest overflow. This Dorset Village home offers the charm of yesterday with the conveniences of today! A must see! ALL MEASUREMENTS APPROXIMATE

Listed by Katherine Zilkha of Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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1115 River Road Manchester VT 05255

Manchester, VT1115 River Road

Price$529,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4685620

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 3,472

2 houses, 5 outbuildings + 25 acres with desirable River Rd address. For weekenders, agriculturalists, at-home entrepreneurs, or historic preservation buffs. The White house, circa 1840, has period features and 4 bdrms. The Red house, with 3 bdrms, was converted from a carriage barn in 1949. Both are livable with 2 baths in each and older kitchens. They share a splendid view of the river, field, and mountain. Important note: the landowners have indicated plans to keep the meadow forever open which means that the view should not be obstructed in the future. Barn has 6 horse stalls and an attached 3-bay shed. Corn house can be used for storage; a small building now houses a home office; there is a 1-car garage and a second barn. 25 wooded acres on the north abut the Hildene museum. There is no property in Manchester like this one. 2 houses give many options: live in one and rent the other for income or to house a caretaker; use the second house for an allowed, at-home business; or use one building as a bed-and-breakfast or private guesthouse. The property could work as an artists' or writers' retreat. Outbuildings are ideal for keeping horses/sheep/goats. Raise llamas or start a plant nursery. With work and imagination, the outbuildings could be converted into other living quarters, greenhouses, or edifices for at-home businesses. Although work is needed, there are ways of raising funds from the land. 3 potential building lots have been identified in the rear acreage.

Listed by Greg Cutler of TPW Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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665 10 Route Chester VT 05143

Chester, VT665 10 Route

Price$399,000

Est. Mortgage: $/month

MLS Number 4776152

  • Residential Single Family
  • Construction Existing
  • Bathroom 7
  • Bedrooms 9
  • Square Feet 5,482

Are you ready to live the ultimate dream of running your own business in Vermont? Once featured in Country Inns of New England this property could be yours! Current owner once operated a successful 24 seat restaurant that includes commercial kitchen, 6 nicely appointed rooms for guests (plus two additional rooms) and owner's quarters. What do you want to do? inn, bed and breakfast, retreat, events...you name it! Located conveniently to I91, Okemo Mountain (only a few minutes drive), several other ski resorts, the shopping in Manchester and villages of Chester, Weston and Cavendish you could not ask for a better spot to live and work in Southern Vermont. There is much to love about this antique farmhouse from the ornate woodwork to the hardwood floors this property feels like home. The barn offers a multitude of possibilities (woodworking shop, dance space, yoga space, events). The outdoor space speaks to country living with gardens, pond and level yard.

Listed by Lisa Kelley and Tyleen Murray of Kelley Real Estate, Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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8273 Windham Hill Road Windham VT 05359

Windham, VT8273 Windham Hill Road

Price$399,000

Est. Mortgage: $/month

MLS Number 4645210

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 5
  • Square Feet 4,274

Lovingly restored Vermont historic home. Over 10 acres of private land with a pond, fire pit, and vistas for you to enjoy! Snowmobile right from this home to the VAST trail, or take a short drive to your choice of 4 ski mountains plus many waterfalls and hikes just a short drive away! This seller paid Vtel to run phone, cable, and internet to the house. Two college students and two adults were able to work/school from home with outstanding wifi service!

Listed by Carrie Mathews of William Raveis Winhall

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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21 Tapper Street Ludlow VT 05149

Ludlow, VT21 Tapper Street

Price$350,000

Est. Mortgage: $/month

MLS Number 4811530

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 6
  • Square Feet 3,523

The Chapman House is an historic eclectic Victorian home in the Village of Ludlow. It has been in the same loving hands of the current owner for over 30 years and he has maintained and improved it with great care over the years. The entire first level is a fantastic space to socialize with large groups. It features a TV room, dining room, eat-in kitchen, game room and bar room with a giant brick hearth. The second floor consists of four bedrooms and two bathrooms. The third floor has two large bedrooms, another bathroom and a relaxing sitting area in the tower. There is a large yard with a spring fed brook and sledding hill, plus plenty of room for parking. There is enough land to add another building if one desires and the house is on town water and sewer. This is a perfect year round getaway home for family and friends and is suitable as a multi-family vacation home. Also offers great rental potential for large groups. The location is prime...on the shuttle route and less then a half mile to Okemo Mountain. It's easy to take ski shuttle back to house and walk to restaurants and shops. Get ready for fun times in Vermont! Ask for a list of the recent improvements to this home.

Listed by Gail Beardmore and Uli Donohue of Engel & Volkers Okemo-Woodstock

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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92 Barrows Heights Dorset VT 05251

Dorset, VT92 Barrows Heights

Price$340,000

Est. Mortgage: $/month

MLS Number 4726148

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 2,771

The best of both worlds - quiet, peaceful location on Barrows Heights road within a few blocks of bucolic of Dorset Village Green. Enjoy evening strolls to restaurants, stores and theatre. The property is adjacent to the historic Barrows House Resort offering summer tennis and swimming pool club. This two story "salt box" home is ready for you to make it your own. School choice is with Dorset Elementary and Middle School, Burr and Burton Academy and Long Trail School for High School. With 5 bedrooms, 4 baths and home office space in almost 2500 square feet - there is plenty of room for the whole family. Unfinished In-Law suite extension of attached garage can serve extended family or guests. Walk to all village amenities while being privately tucked away on charming 3.43 acre wooded lot. House in reasonable "average" condition. Being sold "AS IS".

Listed by R. Diedrich August of RE/MAX Four Seasons

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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3056 Shunpike Road Mount Holly VT 05758

Mount Holly, VT3056 Shunpike Road

Price$339,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4805174

  • Residential Single Family
  • Construction Existing
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 3,072

Wonderful listing offered in Mount Holly! This 5 bedroom antique home is filled with lots of country charm of yesteryear. Exposed beams, pretty fixtures, hardwood floors and decorative trim not found in newer homes. This home boasts many possibilities for entertaining with large kitchen and living room, back sun room and great outdoor space. The property offers large level yard, roomy shed, barn and two car garage. There is an outdoor sauna (not functional) that could be brought back for enjoying and relaxing after a full day of skiing! The kitchen is modern with cooktop, wine cooler, large oven, pantry and gorgeous copper farmers sink. Owners have loved this home and done many upgrades over the years but now its time to pass it on. One bathroom upstairs is in process of remodel and large bedroom nearby would make ideal in-law suite.

Listed by Lisa Kelley and Sean Williams of Kelley Real Estate, Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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2155 VT Route 11 East Route Chester VT 05143

MLS Number 4813504

  • Residential Single Family
  • Construction Existing
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 1,889

Dreaming of having your own business space and live on-premises? This charming 1830's brick home with fully restored barn, might be just the right property! The home was carefully renovated with keeping all the original character in mind. Welcome yourself through the main entry to find an interior brick wall in the open concept kitchen and dining area. This room is warmed with beautiful softwood floors and plenty of natural light from the large picture windows on both south and north side of the home. The living area is equipped with a soapstone wood stove and will surely provide ample heat. An office, 3/4 bath, and first floor master complete the main living level. Two spacious bedrooms on the second story are bright and perfect for extra guest space if needed. The barn is what will really pique your interest having been fully renovated structurally and cosmetically. This was once home to a bustling antique shop and offered great exposure being on Route 11, nestled between Chester and Springfield. Let your imagination soar with all the possibilities this unique property has to offer!

Listed by Amanda Stearns and Joan Morey of Barrett and Valley Associates, Inc/Chest

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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4976 Vermont 30 Route Dorset VT 05251

Dorset, VT4976 Vermont 30 Route

Price$215,000

Est. Mortgage: $/month

MLS Number 4814566

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,398

This c1900 immaculate and well maintained cape offers easy living and rustic charm conveniently located on the edge of historic Dorset Village with private back yard with a gazebo and pond for your enjoyment. The main level has a gorgeous open kitchen/dining space recently updated with newer appliances, new wood floors and attention to detail with unique tile and woodwork, a cozy living room with wood burning fireplace with hearth, light filled Master bedroom with bay window and renovated master bath and entry/mudroom with slate tile floors. Upstairs boasts 2 more generous bedrooms with great built-ins, newer wall to wall carpet and a second newly tiled bath. Escape to the attached 1 car garage with wood stove and old reclaimed barn doors that has been thoughtfully redone with newly poured concrete floor with an impressive 16 foot bar with fixed bar stools made from antique tractor seats. Other amenities include, a new septic (2017), freshly painted exterior, new 16x20 deck, slate patio, pond deck, stonewalls and attached carport. Incredible value and opportunity!

Listed by Melissa Genovart of Rhodes Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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1280 Simonsville Road Andover VT 05143

Andover, VT1280 Simonsville Road

Price$189,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4806865

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,698

This historic 1850's school house has been wonderfully renovated and is ready to go. Every inch has been painted and improved and it is move in ready. With Large living room and over sized fireplace this will make for a perfect cozy night in or for entertaining a large crowd. The spacious eat in kitchen, first floor laundry is ideal for a growing family while the affordable price makes this a first time home buyers dream. Access to the VAST trail is just a few hundred feet away and in 20-30 minutes you can be on Stratton, Okemo and Magic mountain which makes this a great vacation home too. Move quick, this one wont last long!

Listed by Daire Gibney of Barrett and Valley Associates, Inc/Chest

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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442 Main Street Chester VT 05143

Chester, VT442 Main Street

Price$175,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4799855

  • Residential Single Family
  • Construction Existing
  • Bathroom 1
  • Bedrooms 4
  • Square Feet 2,264

This antique home maintains many characteristics of it's time. Always a family home, and ready for your upgrades . Live on Main Street and enjoy the benefits of sidewalks, conveniences, and meeting your neighbors on a stroll. Enjoy an outdoor covered patio, attached barn, garage, and an exceptionally large rear and side yard. The home has 4 bedrooms, plenty of common area and super extended space on the second floor over the barn. Bring your creativity when you visit and imagine how you can nurture this home and make it your own!

Listed by Amanda Stearns and Joan Morey of Barrett and Valley Associates, Inc/Chest

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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1425 Trebo Road Chester VT 05143

Chester, VT1425 Trebo Road

Price$160,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4775710

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,296

Located on a long country road in the town of Chester is an antique cape well worth visiting. Perched just right on 2 acres, it offers a private rear yard and easy access to the village. This substantial home has spacious rooms including master on the main level, wide pine floors, updated bathroom and four bedrooms! A great workshop as well as a country covered porch and an incredible location all complete this property. Come and see what country living, yet a short drive to town, is all about!

Listed by Amanda Stearns of Barrett and Valley Associates, Inc/Chest

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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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33 100 N Route Jamaica VT 05155

Jamaica, VT33 100 N Route

Price$155,000

Est. Mortgage: $/month

MLS Number 4680489

  • Residential Single Family
  • Construction Existing
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 1,329

Charming historical farmhouse with barn located within minutes of the mountains! On the first floor you will find a full kitchen with walk-in pantry and soapstone sink next to separate dining and living rooms. A bathroom, master bedroom and full washer/dryer set can also be found on the main level. The second story has 2 bedrooms, one enjoys a spacious sitting room or office space. Upstairs has 2 large closets with plenty of storage space for all of your gear. This unique property is zoned for both commercial and residential use. The Winhall River borders the lot and it is located in a Flood Zone.

Listed by Annie Bessette and Peggy O'Neill of TPW Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.07% last updated on Jul 2, 2020
* 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 2020 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. 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 July 7, 2020.