Single 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 Single 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 5060368
Status Active Under Contract
DOM 69 days
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. In addition, this is an income-producing property with an accessory living apartment that has a separate entrance. Offset expenses, enjoy multigenerational living, or merge and expand the home back to a single family. 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. This property offers many choices. The stonework, gardens, and detached, expansive two-car garage all add to the desirability. New oil tank in 2024 and you will be impressed with the 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.

Room Features

Bathroom Full 7.3x12.2
Bedroom 14.5x15.2
Bedroom 2 9.4x14.8
Bedroom 3 9.10x11.9
Kitchen/Dining 11.8x21.2
Living/Dining 12.9x21.4

Lot & Building Features

Appliances Dishwasher, Washer, Refrigerator, Microwave, Gas Stove, Dryer
Features Interior 1st Floor Laundry, Soaking Tub, Kitchen/Dining, In-Law/Accessory Dwelling, Dining Area
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 Stone
Lot Description Sidewalks, Street Lights
Roof Asphalt Shingle, Slate, Metal
Features Exterior Barn, Outbuilding, Deck
Total Rooms 11
Garage Yes
Full Baths 2
Half Baths 0

Community and Schools

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

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.

Comparable Properties Sold Near By

Low
$315,000
$123 / sqft
Average
$439,375
$160 / sqft
High
$487,500
$172 / sqft

Address City Zip Beds Baths Price Sq. Ft. $/SQFT Sold Date
This Listing Brattleboro 05301 4 2.0 $395,000 2,715 $145 N/A
60 Moonlight Lane Brattleboro 05301 3 2.0 $480,000 2,767 $173 01/24/2025
502 Oxbow Road Hinsdale 03451 3 2.0 $315,000 2,552 $123 03/27/2025
101 Washington Street Brattleboro 05301 5 3.0 $475,000 2,823 $168 04/23/2025
32 Christie Lane Brattleboro 05301 3 3.0 $487,500 2,832 $172 07/25/2025

Map of 105 Chestnut Street, Brattleboro, VT

Location Map Street View
Listed by Brattleboro Area Realty, Kristen Ziter Taylor
Photo of Crissa Kounavis
Direct: 301-648-7886
Office
655 Wallis Road.
Rye, NH 03870
603-964-7000
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20%
1.6275949367089%
6.75%
$
$
$
Monthly Payment
Principal & Interest
Monthly Taxes
Monthly HOA
Monthly Home Ins.
Monthly PMI

105 Chestnut Street (MLS #5060368) is a multi-family single family home located in Brattleboro, VT. This single family home 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.

The 5 bedroom single family home at 101 Washington Street in Brattleboro is nearby and sold for $475,000 on 04/23/2025. Another nearby 3 bedroom single family home, 32 Christie Lane in Brattleboro sold for $487,500 on 07/25/2025.

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