Charming Traditional New England cape built in 1871 with many upgrades. Located on a lovely cul-de-sac street. Enter through your classic mudroom, with a newly replaced floor, into a fabulous renovated kitchen that has a retro flare with lively yellow tile, & framed black & white tile backsplash. The kitchen is impressive with a nook & granite table & a combination of closed cabinets & open oak shelving. There is a graceful flow from the eat-in kitchen to the formal dining room & then to the spectacular living room. All rooms have over 9-foot ceilings & an abundance of southeastern light. The first floor also has a private laundry room & full bath. Upstairs are four bedrooms with a half bath. A very private, sweet fenced in backyard with a lovely low maintenance garden & a sprinkle of pear trees. There is also an attached garage, & a 21 x 28 barn that can offer endless possibilities. Upgrades to include a renovated kitchen, upgraded electric system, new plumbing, refinished all of the beautiful first-floor hardwood & staircase, insulated second-floor bathroom with ceiling, repairs to roof in 2022, newly rebuilt front porch, replaced stairway & upstairs hall carpet, installed sliding glass shower door, & new electric garage door. This home is close to town conveniences & all our beautiful Brattleboro has to offer. Easy access to I91, close to Boston and New York City. A very charismatic yet practical home. Showings start Saturday, May 10th by appointment.
Closed
Listed by: Brattleboro Area Realty • Kristen Ziter Taylor
Bought with: Brattleboro Area Realty
$322,280
108 Chestnut Street, Brattleboro, VT 05301
4beds
1,544sqft
Single Family Residence
Built in 1871
9,583 Square Feet Lot
$336,500 Zestimate®
$209/sqft
$2,453 Estimated rent
Home value
$336,500
Estimated sales range
Not available
$2,453/mo
Zestimate® history
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List your homeWhat's special
Low maintenance gardenPrivate laundry roomRenovated kitchenLovely cul-de-sac streetAbundance of southeastern lightFenced in backyard
Zillow last checked:
Listing updated:
Listed by:
Kristen Ziter Taylor,
Brattleboro Area Realty 802-257-1335
Bought with:
Christine M Lewis
Brattleboro Area Realty
Source: PrimeMLS,MLS#: 5039492
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 2
- Full bathrooms: 1
- 1/2 bathrooms: 1
Heating
- Oil, Baseboard
Cooling
- Mini Split
Appliances
- Included: Dishwasher, Dryer, Refrigerator, Washer, Electric Stove, Domestic Water Heater
- Laundry: 1st Floor Laundry
Features
- Dining Area, Kitchen/Dining, Living/Dining, Natural Light, Natural Woodwork
- Flooring: Carpet, Hardwood, Vinyl, Wood
- Basement: Dirt Floor,Full,Interior Stairs,Unfinished,Interior Access,Interior Entry
Interior area
- Total structure area: 2,138
- Total interior livable area: 1,544 sqft
- Finished area above ground: 1,544
- Finished area below ground: 0
Property
Parking
- Total spaces: 1
- Parking features: Paved, Auto Open, Driveway, Garage, Off Street, Barn, Attached
- Garage spaces: 1
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: 1st Floor Full Bathroom, 1st Floor Laundry
Features
- Levels: Two
- Stories: 2
- Patio & porch: Covered Porch
- Frontage length: Road frontage: 60
Lot
- Size: 9,583 Square Feet
- Features: Level, Sidewalks, Street Lights, In Town, Near Shopping, Neighborhood, Near Hospital
Details
- Additional structures: Barn(s)
- Parcel number: 8102515577
- Zoning description: Res
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape
- Property subtype: Single Family Residence
Materials
- Wood Frame, Asbestos Exterior
- Foundation: Stone
- Roof: Slate
Condition
- New construction: No
- Year built: 1871
Utilities & green energy
- Electric: 200+ Amp Service
- Sewer: Public Sewer
- Utilities for property: Cable Available, Phone Available
Community & HOA
Community
- Security: Battery Smoke Detector
Location
- Region: Brattleboro
Financial & listing details
- Price per square foot: $209/sqft
- Tax assessed value: $155,570
- Annual tax amount: $4,818
- Date on market: 5/6/2025
- Road surface type: Paved
Price history
| Date | Event | Price |
|---|---|---|
| 6/27/2025 | Sold | $322,280+1%$209/sqft |
Source:  PrimeMLS #5039492 Report a problem | ||
| 5/13/2025 | Contingent | $319,000$207/sqft |
Source: PrimeMLS #5039492 Report a problem | ||
| 5/6/2025 | Listed for sale | $319,000+32.9%$207/sqft |
Source: PrimeMLS #5039492 Report a problem | ||
| 2/16/2022 | Sold | $240,000+6.7%$155/sqft |
Source: PrimeMLS #4892484 Report a problem | ||
| 12/12/2021 | Pending sale | $225,000$146/sqft |
Source: Better Homes and Gardens Real Estate The Masiello Group #4892484 Report a problem | ||
| 12/3/2021 | Listed for sale | $225,000+106.4%$146/sqft |
Source: PrimeMLS #4892484 Report a problem | ||
| 11/19/2015 | Sold | $109,000-22.1%$71/sqft |
Source: Public Record Report a problem | ||
| 8/20/2015 | Price change | $139,900-9.7%$91/sqft |
Source: 2519-12 #4426115 Report a problem | ||
| 5/30/2015 | Listed for sale | $154,900$100/sqft |
Source: Better Homes and Gardens Real Estate The Masiello Group #4426115 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | -- | $155,570 |
| 2023 | -- | $155,570 |
| 2022 | -- | $155,570 |
| 2021 | -- | $155,570 |
| 2020 | -- | $155,570 |
| 2019 | -- | $155,570 |
| 2018 | -- | $155,570 |
| 2017 | -- | $155,570 -17.2% |
| 2016 | -- | $187,970 +9898.4% |
| 2015 | -- | $1,880 |
| 2014 | -- | $1,880 |
| 2013 | -- | $1,880 |
| 2012 | -- | $1,880 |
| 2011 | -- | $1,880 |
| 2010 | -- | $1,880 +7.4% |
| 2009 | -- | $1,751 |
| 2008 | -- | $1,751 |
| 2007 | -- | $1,751 |
Find assessor info on the county website
Neighborhood: 05301
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Nearby schools
GreatSchools rating
- 8/10Green Street SchoolGrades: PK-6Distance: 0.6 mi
- 6/10Brattleboro Area Middle SchoolGrades: 7-8Distance: 0.9 mi
- NAWindham Regional Career CenterGrades: 9-12Distance: 0.9 mi
Schools provided by the listing agent
- Elementary: Brattleboro Elem Schools
- Middle: Brattleboro Area Middle School
- High: Brattleboro High School
Source: PrimeMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Vermont
- Windham County
- Brattleboro
- 05301
- 108 Chestnut Street
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