Multi-Family for Sale: 105 Chestnut Street, Brattleboro, VT 05301

4 beds
2 full baths
2,715 sqft
$395,000
$395,000
105 Chestnut Street, Brattleboro, VT 05301
4 beds
2 full baths
2,715 sqft
$395,000
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Price:
$395,000

Type Multi-Family
Style Multi-Family
Beds 4
Baths 2 full baths
Square Feet 2,715 sqft
Lot Size 0.78 acres
Year Built 1895
Taxes Paid $6,429

City Brattleboro
County Windham

MLS 5060371
Status Active Under Contract
DOM 69 days
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

Utilities Cable Available, Telephone Available
Construction Vinyl Siding
Cooling None
Heating Baseboard, Oil
Parking Description Detached, Paved, Off Street, Garage, Driveway
Sewer Public
Tax Year 2025
Taxes Paid $6,429
Water Public
Basement Description Concrete Floor, Interior Stairs, Full, Dirt
Foundation Brick, Stone
Lot Description Level, Street Lights, Sidewalks
Roof Asphalt Shingle, Slate, Metal
Features Exterior Barn, Outbuilding, Deck
Garage Yes

Community and Schools

Elementary School Brattleboro Elem Schools
Junior High School Brattleboro Area Middle School
Senior High School Brattleboro High School

Unit Features

Unit 1 Baths 1
Unit 1 Bedrooms 3
Unit 1 Rental Agreement No
Unit 1 Rooms 5
Unit 2 Baths 1
Unit 2 Bedrooms 1
Unit 2 Rental Amount 700.00
Unit 2 Rental Amt Freq Monthly
Unit 2 Rooms 3
Unit 2 Status Leased

Price History of 105 Chestnut Street

Date Name Price Difference
09/09/2025 Listing Price $395,000 N/A
*Information provided by REWS for your reference only. The accuracy of this information cannot be verified and is not guaranteed.

Map of 105 Chestnut Street, Brattleboro, VT

Location Map Street View
Listed by Brattleboro Area Realty, Kristen Ziter Taylor
Photo of Maureen Carey
Direct: 603-944-7834
Office
560 High Street
Hampton, NH 03842
603-929-1100
$
20%
1.6275949367089%
6.75%
$
$
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Monthly Payment
Principal & Interest
Monthly Taxes
Monthly HOA
Monthly Home Ins.
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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.

Nearby zip codes are 03446, 03451, 03466, 05350 and 05354. This property neighbors other cities such as Chesterfield, Dummerston, Guilford, Hinsdale and Vernon.

PrimeMLS

Listing Last updated . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available. Walk Score map and data provided by Walk Score. Google map provided by Google. Bing map provided by Microsoft Corporation.

All information provided is deemed reliable but is not guaranteed and should be independently verified.

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