164 Chestnut St

Brattleboro, VT 05301

$285,000
Price
3
Beds
1,323 Sq. Ft.
$215 / Sq. Ft.
1,323
Sq. Ft.
$215
per Sq. Ft.
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Description

Just right for new beginnings! This raised ranch affords the new home buyer a cozy place to start with a big, level yard with lots of flowering shrubs to look pretty when you drive up, and a perfect spot for ball in the back! The dead end street is a bit safer for bikes and strolls than others and creates a nice comfortable neighborhood for smiling greetings. With an eat in kitchen with sliders to the back for grilling and a living room with a picture window to the front yard, you can tuck in and...Just right for new beginnings! This raised ranch affords the new home buyer a cozy place to start with a big, level yard with lots of flowering shrubs to look pretty when you drive up, and a perfect spot for ball in the back! The dead end street is a bit safer for bikes and strolls than others and creates a nice comfortable neighborhood for smiling greetings. With an eat in kitchen with sliders to the back for grilling and a living room with a picture window to the front yard, you can tuck in and enjoy. Half of the lower level is finished and is perfect for a den, at home office or playroom. Plenty of storage in the unfinished portion, so stock up on those sale items! Please be prequalified before making an appointment to view.
  1. Listed by Christine Lewis • Brattleboro Area Realty

Property Details for 164 Chestnut Street

Zoning
R
LISTING UPDATED: 03/14/2026 10:06 PM

Property Details for 164 Chestnut Street

StatusActive
MLS #5044816
Days on Market282
Taxes$5,140 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1984
Lot Size0.22 AC / 9,583 SF
CountyWindham County
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Location

Listing Courtesy of Brattleboro Area Realty
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Building Information for 164 Chestnut Street

Stories1Year Built1984Building Size-Lot Size0.22 AC / 9,583 SF

Payment Calculator

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$1,811 per month

30 year fixed, 6.11% Interest

Principal and Interest

$1,383

Property Taxes

$428

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 164 Chestnut Street

Summary
Location and General Information
  • City: Brattleboro
  • County: VT-Windham
  • Directions: Canal Street/RT 5 to Maple St, right on Locust, left on Chestnut, home on left.
  • Latitude: 42.846814397499344
  • Longitude: -72.574304347221371
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Street Designation: Street
  • Zip Code: 05301
Taxes and HOA Information
  • SPAN Number: 081-0255-10431
  • Tax Year: 2024
  • Taxes TBD: No
Parking
  • Garage: No
  • Driveway: Paved
Property
Lot Information
  • Footprint: 24x37
  • Lot Features: Landscaped, Level, Open, Slight, Sloping
  • Lot Size Acres: 0.22
  • Road Frontage Length: 82.0
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: No
  • PreConstruction: No
  • Surveyed: Unknown
  • Year Built: 1984
Utilities
  • Electric Company: GMP
  • Cable Company: Comcast
  • Fuel Company: Dead River
  • Electric: Circuit Breaker(s)
  • Sewer: Public
  • Water Source: Public
  • Utilities: Cable, Telephone Available
  • Internet: Cable Internet, Fiber Optic Internt Avail
Interior and Exterior Features
Exterior Features
  • Color: yellow
  • Construction Materials: Wood Frame, Vinyl Siding
  • Roof: Metal
Interior Features
  • Appliances: Dryer, Range Hood, Microwave, Mini Fridge, Electric Range, Refrigerator, Washer, Tank Water Heater
  • Basement: Yes
  • Basement Access Type: Interior
  • Basement Description: Concrete, Concrete Floor, Finished, Frost Wall, Full, Insulated, Interior Access, Interior Stairs, Storage Space, Sump Pump, Unfinished
  • Rooms: Level 1: Level 1: Bedroom, Level 1: Full Bathroom, Level 1: Kitchen/Dining, Level 1: Living Room
  • Rooms: Level B: Level B: Bedroom, Level B: Office/Study, Level B: Utility Room
  • Flooring: Vinyl
  • Heating: Oil, Pellet Stove, Forced Air, Hot Air
  • Cooling: Other
  • Total Stories: 1
Room Information
Room 1
  • Room Dimensions: 11x19
  • Room Level: 1
  • Room Type: Kitchen/Dining
Room 2
  • Room Dimensions: 12x14
  • Room Level: 1
  • Room Type: Living Room
Room 3
  • Room Dimensions: 11x12
  • Room Level: 1
  • Room Type: Bedroom
Room 4
  • Room Dimensions: 10x16
  • Room Level: 1
  • Room Type: Bedroom
Room 5
  • Room Dimensions: 10x12
  • Room Level: Basement
  • Room Type: Bedroom
Room 6
  • Room Dimensions: 05x08
  • Room Level: 1
  • Room Type: Bathroom Full
Room 7
  • Room Dimensions: 11x134
  • Room Level: Basement
  • Room Type: Utility Room
Room 8
  • Room Dimensions: 10x13
  • Room Level: Basement
  • Room Type: Office/Study

Property History for 164 Chestnut Street

DateEvent & SourcePriceAppreciation
Jun 5, 2025

Listed (Active)

New England Real Estate Network #5044816

$319,900—
Feb 5, 2019

Sold (Public Record)

Public Record #639261453

$165,000

+1.0% / yr

Feb 5, 2019

Sold

New England Real Estate Network #4725063

$165,000—
Feb 5, 2019

Pending

New England Real Estate Network #4725063

—
Oct 24, 2018

Listed (Active)

New England Real Estate Network #4725063

$169,000—
Nov 9, 2017

Expired

New England Real Estate Network #4632635

—
May 8, 2017

Listed (Active)

New England Real Estate Network #4632635

$165,000—
Oct 4, 2011

Sold (Public Record)

Public Record #316336903

$153,000

-4.4% / yr

Oct 3, 2011

Sold

New England Real Estate Network #3072753

$153,000—
Oct 3, 2011

Pending

New England Real Estate Network #3072753

—
Aug 21, 2009

Price Change

New England Real Estate Network #3072753

$192,000—
Aug 21, 2009

Listed (Active)

New England Real Estate Network #3072753

$155,000—
Dec 27, 2006

Sold (Public Record)

Public Record #301084862

$189,900—
Dec 13, 2006

Sold

New England Real Estate Network #3030666

$189,900—
Nov 21, 2006

Pending

New England Real Estate Network #3030666

—
Jul 31, 2006

Price Change

New England Real Estate Network #3030666

$193,500—
Jul 31, 2006

Listed (Active)

New England Real Estate Network #3030666

$189,900—
Jun 27, 2002

Sold

New England Real Estate Network #3011425

$91,000—
May 14, 2002

Pending

New England Real Estate Network #3011425

—
Nov 2, 2001

Listed (Active)

New England Real Estate Network #3011425

$95,000—
DateEvent & SourcePrice
06/05/2025

Listed (Active)

New England Real Estate Network #5044816

$319,900
02/05/2019

Sold (Public Record)

Public Record #639261453

$165,000

+1.0% / yr

02/05/2019

Sold

New England Real Estate Network #4725063

$165,000
02/05/2019

Pending

New England Real Estate Network #4725063

—
10/24/2018

Listed (Active)

New England Real Estate Network #4725063

$169,000
11/09/2017

Expired

New England Real Estate Network #4632635

—
05/08/2017

Listed (Active)

New England Real Estate Network #4632635

$165,000
10/04/2011

Sold (Public Record)

Public Record #316336903

$153,000

-4.4% / yr

10/03/2011

Sold

New England Real Estate Network #3072753

$153,000
10/03/2011

Pending

New England Real Estate Network #3072753

—
08/21/2009

Price Change

New England Real Estate Network #3072753

$192,000
08/21/2009

Listed (Active)

New England Real Estate Network #3072753

$155,000
12/27/2006

Sold (Public Record)

Public Record #301084862

$189,900
12/13/2006

Sold

New England Real Estate Network #3030666

$189,900
11/21/2006

Pending

New England Real Estate Network #3030666

—
07/31/2006

Price Change

New England Real Estate Network #3030666

$193,500
07/31/2006

Listed (Active)

New England Real Estate Network #3030666

$189,900
06/27/2002

Sold

New England Real Estate Network #3011425

$91,000
05/14/2002

Pending

New England Real Estate Network #3011425

—
11/02/2001

Listed (Active)

New England Real Estate Network #3011425

$95,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 164 Chestnut Street

Taxable ValueLand$45,800Additions$105,830Total$151,630
Tax Record2024$4,923 ($410 / month)
Home Facts
Baths1Total Finished SqFt882 SqFtAbove Grade Finished SqFt882 SqFtStories1Lot Size9,583 SqFtStyleMobile / Manufactured HomeYear Built1984CountyWINDHAMAPN(025) 00315303.400

Schools near 164 Chestnut Street

This home is within Windham Southeast Unified Union School District #96.
Rating
School
Type
Grades
Distance
Academy School
Public - PK to 6
Brattleboro Area Middle School
Public - 7 to 8
Brattleboro Senior Uhsd #6
Public - 9 to 12
Windham Regional Career Center
Public - 9 to 12
Rating
School
Distance
Academy School
PublicPK to 6

Brattleboro Area Middle School
Public7 to 8

Brattleboro Senior Uhsd #6
Public9 to 12

Windham Regional Career Center
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 164 Chestnut Street, Brattleboro, VT 05301

164 Chestnut Street is a single family home for sale in Brattleboro, VT 05301. This property was listed for sale on June 5, 2025 by Brattleboro Area Realty, it's currently listed at $285,000. It has been on the market for a total of 282 days and was last sold on February 5, 2019. This listing's school district is Windham Southeast Unified Union School District #96. Nearby schools include Academy School, Brattleboro Area Middle School and Brattleboro Senior Uhsd #6. 164 Chestnut Street is a 3-bed, 1-bath, 1,323 sqft single family home built in 1984.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Brattleboro Area Realty

Copyright 2026 PrimeMLS, 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 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 03/29/2026 10:59 AM