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Windsor VT Real Estate

Windsor has one of the finest collections of Federal Period houses in all of New England. Many, along with the Congregational Church, were designed by the renowned 18 th century architect, Asher Benjamin. The Old Constitution House, a Vermont State Historic Site, was the site of the drafting of Vermont’s State Constitution in 1777. Hence, Windsor is known as the birthplace of Vermont. Windsor is also home to the American Precision Museum, recounting and preserving the local manufacturing legacy.

Found 35 listings using search criteria.
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$695,000
Year Built 1791
Acres 0.92

Cross the longest covered bridge in the United States to our old Vermont mill town where the homestead of Dr. Isaac Green has fireplaced bedchambers all with private baths, and a unique combination of historical elements and details. The property is a collection of original late 18th and early 19th century buildings joined around a central open courtyard. Underground stone chambers, messages from the past, mysterious rooms and elegant "Indian Shuttered" parlors are a part of an intensive historical and architectual fabric that was woven around an important Vermont family in Vermont’s most historic town. Currently operating as an owner ocupied historic "Inn at Windsor".

$695,000
Bedrooms 5
Bathrooms 5
Sq. Ft. 4200.00
Year Built 1791
Acres 0.92

Cross the longest covered bridge in the United States to our old Vermont mill town where the homestead of Dr. Isaac Green has fireplaced bedchambers all with private baths, and a unique combination of historical elements and details. The property is a collection of original late 18th and early 19th century buildings joined around a central open courtyard. Underground stone chambers, messages from the past, mysterious rooms and elegant "Indian Shuttered" parlors are a part of an intensive historical and architectual fabric that was woven around an important Vermont family in Vermont’s most historic town.

$569,000
Bedrooms 3
Bathrooms 3
Sq. Ft. 2865.00
Year Built 1800
Acres 17.92

This property is a charming antique center chimney cape with a new addition consisting of the 2 car attached garage with a fabulous vaulted ceiling family/library/music room, and guest suite above. 2 working fireplaces, one with wood stove. Custom cherry kitchen, pantry, laundry and many original features of the old cape. The master bath has a deep soaking tub as well as a shower with glass surround looking out onto the orchard and gardens. Fenced back yard for dogs, a wood shed and apple trees.

$442,000
Sq. Ft. 8599
Year Built 1900
Acres 0.32

Great opportunity to have 9 units all together for ease of maintenance. New roof on 77 Union and 1/2 of a new roof on 45-47 Ascutney ( slate on the other side). Almost all windows are replacements, wood floors, very spacious units, some tin ceilings, some fireplaces, some have their own basement space for storage. Vinyl and metal exteriors. Coin op laundry in Union Street for both buildings. Easy walk to downtown.

$425,000
Bedrooms 3
Bathrooms 2
Sq. Ft. 2400.00
Year Built 1998
Acres 14.00

Beautiful home situated along country lane with southern views of Mt. Ascutney. Privately sited on 14 acres of mostly wooded land with trails and potential pond site.Modern kitchen with maple cabinetry, granite countertops, butcherblock island, ceramic tiled floors and commercial grade Vulcan propane stove. Spacious dining room with maple hardwood floors. Mudroom, entered from rear, has wood stove hook up and slate floor. The den/study offers nice view from bow window. Living room has cathedral ceiling, with exposed beams and atrium door to deck & hot tub. Second floor offers sunny, spacious master bedroom w/walkin closets, 3rd BR and full bath. Outbuildings include 2 car garage w/leanto, 2 bay open shed and 2 story horse barn. Great country property displaying pride of ownership in all directions. Location is convenient to MT Ascutney Resort, golf and riding trails. Eyecatching landscaping and abundant stone walls greet you upon arrival!

$395,000
Year Built 1929
Acres 0.39

What a unique opportunity! 14,400 square feet with 10’ and 15’ ceilings throughout the building, lovely woodwork, hardwood floors, almost floor to ceiling windows! With a location in the central business district it will allow you to grow in so many directions. Presently, some tenants who would like to stay on. Underground oil tanks are covered by an indemnification agreement from the town of Windsor. ROW in the back of the building - see deed. Lovely stone patio in the front of the building just crying out for tables and chairs! New oil boiler was installed on March 11,2011 with new insulation on the hot water pipes.

$299,000
Bedrooms 3
Bathrooms 3
Sq. Ft. 2600.00
Year Built 1874
Acres 3.50

This 1874 home on 3.5 acres has been tastefully updated while retaining much of its period elegance, including a great hall and library.The living rm is charming and warm featuring a working fireplace. Mstr suite on the main level with full bath, a stone patio and view of Mt. Ascutney. In village location, walk to everything but with quaint privacy

$299,000
Sq. Ft. 0.00
Acres 73.90

Old Mill Pond is comprised of a total of 73.9 acres, of which roughly 15 acres are open field. It has frontage on a 60 acre pond, and entirely encompasses a picturesque 15 acre pond immediately up stream. The property has access to municipal water and sewer and has high density residential development potential. However, it is equally suited as the site of a single residence, or potentially divided into a few building lots. Readily accessed from Interstates 91 and 89, and is an easy 2 hour drive from Boston. The ski resort of Mt Ascutney is 6 miles away and other major ski mountains such as Killington and Okemo are located within one hour’s drive.

$289,000
Bedrooms 3
Bathrooms 3
Sq. Ft. 2400.00
Year Built 2005
Acres 1.47

Superb 3 bedroom, 3 bathroom home, in brand new condition with many updates since construction. Bring your family home to spacious rooms, finished basement, ideal mudroom, paved driveway for shooting hoops, and a perfect setting for relaxing on 2 decks. Beautiful hardwood floors, a woodstove in living room, and wonderful master suite complete this package.

$249,000
Bedrooms 3
Bathrooms 2
Sq. Ft. 2452.00
Year Built 2003
Acres 0.97

Gorgeous newer cape on quiet cul-de-sac nestled privately on nearly an acre. Enjoy the covered front porch surrounded by attractive landscaping and stone walkway. Extra large deck to the rear is fabulous for gatherings and cookouts. Kitchen boasts granite and upgraded appliances. You will be thrilled with the gleaming hardwood floors, oversized Great Room with woodstove and excellent flowing floor plan. This is move-in ready!

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