A very special two unit! The main house is a spacious 3 bedroom, 1 bath with a primary bedroom and laundry on the first floor. The second unit is a desirable 1 bedroom, 1 bath. This authentic and updated Vermont home is situated on welcoming, dead-end street surrounded by woods on two sides creating a feeling of peacefulness and connection with nature. How fortunate to live in town but also have the calming surroundings of mature plantings, opportunity to garden and de-stress in your private sanctuary. Enjoy outdoor dining on the deck, located just off the dining room/kitchen area. The interior, though updated, with a fully modern kitchen and bath, maintains the best of its original features, such as exposed beams, built-ins, large windows, and hardwood floors. The attached antique barn with a workbench is an inviting space for projects or to utilize as a studio. Perhaps add a third unit? This property offers many choices. The stonework, gardens, and detached, expansive two-car garage all add to the desirability. You will be impressed with the new oil tank in 2024, condition, the privacy, the large lot, and all the accessible amenities in Brattleboro, as well as the eclectic community at large. Delayed showings until Sat Sept. 13th by appointment.
Lot & Building Features
UtilitiesCable Available, Telephone Available
ConstructionVinyl Siding
CoolingNone
HeatingBaseboard, Oil
Parking DescriptionDetached, Paved, Off Street, Garage, Driveway
105 Chestnut Street (MLS #5060371) is a multi-family multi-family listing located in Brattleboro, VT.
This multi-family listing is 2,715 sqft and on a lot of 33,977 sqft (or 0.78 acres) with 4 bedrooms, 2 baths and is 130 years old. This property was listed on 09/09/2025 and has been priced for sale at $395,000.
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Listing information courtesy of: Brattleboro Area Realty
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 11/18/2025