475 Upper Dummerston Road, Brattleboro, VT 05301
OFF MARKET
Listed by Rebecca Seymour, Brattleboro Area Realty, (802) 257-1335 . Bought with Brattleboro Area Realty

475 Upper Dummerston Road
Brattleboro, VT 05301

  • 4 Beds
  • 2.5 Baths
  • 2,860 sqft (on 21.77 acres)

$925,700

Trulia Estimate
as of May 14, 2026
Est. Refi. Payment $6,087/mo*
Refinance Your Home

$925,700

Trulia Estimate
as of May 14, 2026
Est. Refi. Payment $6,087/mo*
Refinance Your Home
4 Beds
2.5 Baths
2,860 sqft
(on 21.77 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination
Last check for updates: about 1 hour ago
Listed by Rebecca Seymour
Brattleboro Area Realty, (802) 257-1335
Bought with: Rebecca Seymour, Brattleboro Area Realty, (802) 257-1335
Source: PrimeMLS, MLS#4945883

Description

Rare opportunity to own an elegant 1880's farmhouse with attached 2-car garage & 21+ protected acres just minutes from downtown Brattleboro & with quick access to I91 where you're 2.5 hours from Boston & 3.5 from NY. This gorgeous home sits across the street from the Country Club with 18 holes of golf, a restaurant, & groomed nordic trails in the winter, if you prefer alpine skiing you're only 30 minutes from Mt Snow. This gracious home offers 4 bedrooms, an office, 2 1/2 baths, a kitchen open to a spacious family room that is ideal for entertaining & cozy with a woodstove or use the heat pump to cool in the warmer months, if you prefer a more intimate space adjourn to the dining room with a vintage tin ceiling, the living room is spacious & overlooks the kitchen garden & the wrap around extra wide country porch. The refinished wood floors throughout the house gleam in the sun from the oversized windows which overlook the barn, tunnel greenhouse, & the many established gardens. If homesteading is your dream then you'll be all ready to farm and garden with an expansive meadow, currently being hayed by a neighbor, 6 stall barn, 50' caterpillar tunnel, 18 established beds for low till gardening complete with drip irrigation system. Special option to purchase farm LLC separately. If you'd rather not, then consider leasing to an appreciative local farmer! This home has been repainted inside & out, insulated, & is ready for the next owner. Showings start w/open house on 3/25 11-1
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from May 12, 2023

Home Highlights

Parking
Garage
Outdoor
Porch
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 475 Upper Dummerston Road

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: Interior Stairs,Unfinished,Interior EntryNumber of Rooms: 10
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 1Number of Bathrooms (three quarters): 1Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2860 Square Feet
Appliances & Utilities
Utilities: Cable at SiteAppliances: Dishwasher, Dryer, Electric Range, Refrigerator, Washer, Electric Water Heater, Rented Water Heater, Water HeaterDishwasherDryerLaundry: Laundry Hook-upsRefrigeratorWasher
Heating & Cooling
Heating: Oil,Wood,Electric,Heat Pump,Radiator,Steam,Wood Stove,Mini SplitNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Oil
Fireplace & Spa
Number of Fireplaces: 2Fireplace: Wood Burning, 2 FireplacesHas a Fireplace
Gas & Electric
Electric: 200+ Amp Service
Windows, Doors, Floors & Walls
Window: Screens, Storm Window(s)Flooring: Carpet, Hardwood, Softwood
Levels, Entrance, & Accessibility
Stories: 2.5Levels: 2.5Accessibility: 1st Floor 1/2 Bathroom, 1st Floor Hrd Surfce Flr, Hard Surface Flooring, 1st Floor LaundryFloors: Carpet, Hardwood, Softwood
View
No View
Security
Security: Carbon Monoxide Detector(s), Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: Asphalt Shingle SlatePatio / Porch: Porch, Covered PorchFencing: PartialOther Structures: Barn(s), Outbuilding, Greenhouse, Stable(s)Exterior: Building, Garden, Natural Shade, Shed, StorageFoundation: Block, StoneGarden
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas Open ParkingParking Spaces: 2Parking: Circular Driveway,Gravel,Direct Entry,Driveway,Garage,Attached
Frontage
Road Frontage: PublicRoad Surface Type: Paved
Water & Sewer
Sewer: 1000 Gallon, Leach Field, On-Site Septic Exists
Farm & Range
Frontage Length: Road frontage: 273
Finished Area
Finished Area (above surface): 2860 Square Feet

Property Information

Year Built
Year Built: 1880
Property Type / Style
Property Type: ResidentialProperty Subtype: FarmStructure Type: FarmhouseArchitecture: Antique,Colonial
Building
Construction Materials: Wood Frame, Aluminum SidingNot a New Construction
Property Information
Usage of Home: Agricultural, Farm, Horse/Animal Farm, Field/Pasture, Mixed Use, Tillable

Price & Status

Price
List Price: $795,000
Status Change & Dates
Possession Timing: Close Of Escrow

Media

Location

Direction & Address
City: Brattleboro
School Information
Elementary School: Brattleboro Elem SchoolsJr High / Middle School: Brattleboro Area Middle SchoolHigh School: Brattleboro High School

Building

Building Area
Building Area: 3844 Square Feet

Lot Information

Lot Area: 21.77 Acres

Energy

Energy Efficiency Features: Insulation

Miscellaneous

BasementMls Number: 4945883Above Grade Unfinished Area: 2860Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area: 984Below Grade Unfinished Area Source: Public RecordsBelow Grade Unfinished Area Units: Square Feet

Price History for 475 Upper Dummerston Road

DatePriceEventSource
05/12/2023$850,000Sold
PrimeMLS #4945883
04/14/2023$795,000PendingToActivePrimeMLS #4945883
03/29/2023$795,000ContingentPrimeMLS #4945883
03/17/2023$795,000Listed For SalePrimeMLS #4945883
09/27/2019$568,000Sold
PrimeMLS #4654810
08/15/2019$585,000PendingToActiveAgent Provided
08/15/2019$585,000PendingAgent Provided
07/25/2019$585,000PriceChange
Agent Provided
07/15/2019$600,000PriceChange
Agent Provided
05/22/2019$629,500PriceChange
Agent Provided
09/24/2018$670,000PriceChange
Agent Provided
07/30/2018$695,000PriceChange
Agent Provided
05/25/2018$745,000PriceChange
Agent Provided
08/21/2017$750,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2024
Tax
Assessment$463,120
Home facts updated by county records

Comparable Sales for 475 Upper Dummerston Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
672 East Orchard Street, Brattleboro, VT
0.47
Single-Family Home
$470,000
09/26/25
3
3
3,148
135 Upper Dummerston Road, Brattleboro, VT
0.71
Single-Family Home
$525,000
05/16/25
5
3.5
3,600
395 Hillwinds Road, Brattleboro, VT
0.98
Single-Family Home
$668,000
08/12/25
4
2.5
2,226
155 Upper Dummerston Road, Brattleboro, VT
0.66
Single-Family Home
$407,000
11/21/25
3
1.5
1,655
1073 Upper Dummerston Road, Brattleboro, VT
0.90
Single-Family Home
$525,000
08/19/25
3
2
2,456
84 Magnolia Drive, Brattleboro, VT
0.87
Single-Family Home
$570,000
04/29/26
2
2
1,900
23 Meetinghouse Lane, Brattleboro, VT
1.21
Single-Family Home
$495,000
12/29/25
3
2.5
3,415
139 Buttonwood Drive, Brattleboro, VT
0.87
Single-Family Home
$455,000
03/04/26
2
2
1,390
387 Meadow Brook Road, Brattleboro, VT
1.16
Single-Family Home
$439,000
05/13/26
4
2
1,568
187 Hillwinds Road, Brattleboro, VT
1.33
Single-Family Home
$476,000
11/20/25
4
3
2,372

Assigned Schools

These are the assigned schools for 475 Upper Dummerston Road.
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The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Brattleboro

At least 47 Trulia users voted on each feature.

  • 92 % Say parking is easy

  • 91 % Say it's dog friendly

  • 82 % Say yards are well-kept

  • 81 % Say there's holiday spirit

  • 80 % Say car is needed

  • 80 % Say there's wildlife

  • 72 % Say people would walk alone at night

  • 65 % Say it's walkable to restaurants

  • 62 % Say there are sidewalks

  • 60 % Say neighbors are friendly

  • 58 % Say it's walkable to grocery stores

  • 55 % Say kids play outside

  • 50 % Say there are community events

  • 49 % Say streets are well-lit

  • 48 % Say they plan to stay for at least 5 years

  • 38 % Say it's quiet

Learn more about our methodology.
  • Brenda Nichols
    "Yes! Lots of space for walking and running around with dogs. Quiet countryside with not a lot of traffic."
    0
    Flag
  • Kelly Dias
    "People watch out for each other, sometimes we go Christmas caroling, we watch each others’ pets; we have a messaging group for neighborhood news"
    1
    Flag
  • Kelly Dias
    "It’s a great neighborhood to walk dogs. Sometimes bears come through so if it’s bear season you have to be careful. People are respectful and greet each other and we know each others’ dogs. "
    0
    Flag
  • Jessica Brown
    "I drive through downtown to work and there is some negativity on the streets by way of homelessness and drug abuse/ mental illness. But this neighborhood is still overall a place that I love to live . "
    0
    Flag
  • Kelly Dias
    "Pet friendly, willing to help out and get to know pets. Lots if grass and forested trails for walking and hiking with dogs. "
    0
    Flag
  • Isaac S.
    "Great small town in New England-artsy, funky, liberal. Nice amenities for the size of the town. Still some amount of crime-like everywhere these days."
    5
    Flag
  • Isaac S.
    "Dogs are welcome. Neighbor s are friendly. Houses are well maintained. I feel safe. Walkable neighborhood."
    3
    Flag
  • Jcoursem3
    "Neighbors are friendly and help each other out. Get together’s are organic and easy because of our close proximity. "
    0
    Flag
  • Deanshippee
    "A lot of people trust their dogs without a leash. It’s really annoying especially when every dog owner in. Brattleboro should know about our leash law."
    7
    Flag
  • Isaac S.
    "Car, 5 minutes to work. Few stoplights in town. Friendly drivers except those from Massachusetts and New York. Main Street gets bogged down with traffic but there are several back ways to get around town. Good city for driving in general."
    3
    Flag
  • Grace
    "I grew up in this neighborhood & am raising my daughter here. I love how bike friendly the neighborhood is and that we can walk both downtown & to the farmer’s market."
    11
    Flag
  • rhc3vt
    "Deteriorating economics, falling home prices, difficult to sell homes, few jobs, really bad schools, more and more poor people in trailer parks. There's not much of a future here."
    0
    Flag

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Copyright 2026 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 2026-05-14 12:49:43 PDT.
This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information.

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Off Market Homes Near 475 Upper Dummerston Road

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Explore by feature

475 Upper Dummerston Road, Brattleboro, VT 05301 is a 4 bedroom, 3 bathroom, 2,860 sqft single-family home built in 1880. This property is not currently available for sale. 475 Upper Dummerston Road was last sold on May 12, 2023 for $850,000 (7% higher than the asking price of $795,000). The current Trulia Estimate for 475 Upper Dummerston Road is $925,700.