559 Upper Dummerston Rd, Brattleboro, VT 05301
OFF MARKET

559 Upper Dummerston Rd
Brattleboro, VT 05301

  • 3 Beds
  • 2 Baths
  • 2,536 sqft (on 0.48 acres)

$533,500

Trulia Estimate
as of May 15, 2026
Est. Refi. Payment $3,539/mo*
Refinance Your Home

$533,500

Trulia Estimate
as of May 15, 2026
Est. Refi. Payment $3,539/mo*
Refinance Your Home
3 Beds
2 Baths
2,536 sqft
(on 0.48 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

This handsome contemporary single level home is located on prestigious Upper Dummerston Road and provides lovely views of Fairwinds Farm, The Country Club and distant mountains. Just minutes from downtown, the location is choice and country. The interior is bright and inviting and includes large principal rooms, notably: Spectacular country Kitchen/Family Room, spacious Living Room with fireplace, formal Dining Room, Bedroom wing with master with en suite bath and two additional bedrooms with shared second bath and a lower level office. Beautiful stone walls, 2-car garage, stone house accents and large rear deck all add to the appeal. A wonderful place to call home!!!
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.

Home Highlights

Parking
No Info
Outdoor
Porch, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 559 Upper Dummerston Rd

Interior Features

Heating & Cooling
Heating: Baseboard, Gas, Oil, Wood PelletCooling System: OtherHeating Fuel: Baseboard
Interior Details
Additional StorageNumber of Rooms: 8Types of Rooms: Dining RoomStorageCeiling Fan
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Tile, Carpet, Hardwood

Exterior Features

Exterior Home Features
Roof: AsphaltDeckPorch

Property Information

Year Built
Year Built: 1960
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Building

Levels, Entrance, & Accessibility
Disabled Access

Lot Information

Lot Area: 0.48 acres

Price History for 559 Upper Dummerston Rd

DatePriceEventSource
06/29/2015$329,500Sold
N/A
06/02/2015$339,500PendingAgent Provided
08/08/2014$339,500PriceChange
Agent Provided
04/19/2014$359,000Listed For SaleAgent Provided
12/06/2006$314,900Sold
N/A
02/14/2000$213,000Sold
N/A
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Property Tax and Assessment

Year2024
Tax
Assessment$343,540
Home facts updated by county records

Comparable Sales for 559 Upper Dummerston Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
672 East Orchard Street, Brattleboro, VT
0.27
Single-Family Home
$470,000
09/26/25
3
3
3,148
155 Upper Dummerston Road, Brattleboro, VT
0.77
Single-Family Home
$407,000
11/21/25
3
1.5
1,655
387 Meadow Brook Road, Brattleboro, VT
0.96
Single-Family Home
$439,000
05/13/26
4
2
1,568
1073 Upper Dummerston Road, Brattleboro, VT
0.87
Single-Family Home
$525,000
08/19/25
3
2
2,456
135 Upper Dummerston Road, Brattleboro, VT
0.82
Single-Family Home
$525,000
05/16/25
5
3.5
3,600
395 Hillwinds Road, Brattleboro, VT
0.90
Single-Family Home
$668,000
08/12/25
4
2.5
2,226
1082 W River Road, Brattleboro, VT
1.02
Single-Family Home
$305,000
09/23/25
3
1
1,222
84 Magnolia Drive, Brattleboro, VT
1.08
Single-Family Home
$570,000
04/29/26
2
2
1,900
23 Meetinghouse Lane, Brattleboro, VT
1.04
Single-Family Home
$495,000
12/29/25
3
2.5
3,415
139 Buttonwood Drive, Brattleboro, VT
1.08
Single-Family Home
$455,000
03/04/26
2
2
1,390

Assigned Schools

These are the assigned schools for 559 Upper Dummerston Rd.
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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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Homes for sale near 559 Upper Dummerston Rd

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Off Market Homes Near 559 Upper Dummerston Rd

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559 Upper Dummerston Rd, Brattleboro, VT 05301 is a 3 bedroom, 2 bathroom, 2,536 sqft single-family home built in 1960. This property is not currently available for sale. 559 Upper Dummerston Rd was last sold on Jun 29, 2015 for $329,500. The current Trulia Estimate for 559 Upper Dummerston Rd is $533,500.