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105 Chestnut Street, 
Brattleboro, VT 05301

$395,000


Bed


Bath


2,715

Sq Ft


Multi-Family

Active

Listed by

Kristen Ziter Taylor

Brattleboro Area Realty

802-257-1335

Last updated:

September 13, 2025, 10:23 AM

MLS#

5060371

Source:

PrimeMLS

About This Home

105 Chestnut Street

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.

Home Facts

Multi-Family

Built in 1895

Price Summary

395,000

$145 per Sq. Ft.

MLS #:

5060371

Last Updated:

September 13, 2025, 10:23 AM

Added:

5 day(s) ago


Rooms & Interior

Interior

Living Area:

2,715 Sq. Ft.


Structure

Structure

Building Area:

3,375 Sq. Ft.

Year Built:

1895


Lot

Lot Size (Sq. Ft):

33,977


Finances & Disclosures

Finances

Price:

$395,000

Price per Sq. Ft:

$145 per Sq. Ft.

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Copyright 2025 Prime MLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of Prime MLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated September 14, 2025

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