799 Upper Dummerston Rd, Brattleboro, VT 05301
The apartment is upstairs/downstairs. Upstairs bath down the hall.
Upstairs bath.
OFF MARKET

799 Upper Dummerston Rd
Brattleboro, VT 05301

  • 2 Beds
  • 1 Bath
  • 1,300 sqft

$589,100

Trulia Estimate
as of Aug 11, 2026

$589,100

Trulia Estimate
as of Aug 11, 2026
2 Beds
1 Bath
1,300 sqft

Local Information

  • Map ViewExplore the area around 799 Upper Dummerston Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Living Area
1,300 sqft
Price/Sqft
$453

About this House

Bright 2-story 1830 home. Use the mudroom entry off driveway to drop boots and coats and enter through galley kitchen with granite counters and deep drawer storage, through large doorway to fireplaced living/dining room, or use private entry from big south-facing porch. Carpeted stairway goes from the living room up to the full-width front bedroom with historic south-facing bay window, original wide-plank floors, and ample closet. Second bedroom/office (11x11) with closet is down the hall. Also sunny bathroom with classic porcelain bathtub/shower combo and new large vanity with drawer storage.

All 5 minutes from downtown cinema, coop, great library & shops/restaurants/services, on 38 non-smoking acres of organic flowers, field and forest. Rent includes ALL utilities for this 1300sqft duplex: heat w/programmable thermostat, HW, electricity, shared high speed internet, laundry, plowing.

Note: Some extra storage available in barn; pets and add'l space for winter storage, workshop, stalls, grazing, greenhouse use all negotiable/TBD.
799 Upper Dummerston Rd, Brattleboro, VT 05301 is a 2 bedroom, 1 bathroom, 1,300 sqft single-family home. It last sold for $350,000 on Jul 18, 2017 (14,483% above the $2,400 asking price). More recently, it was listed as a rental in December 2025 with an asking price of $2,400 per month. That rental listing was removed on February 14, 2026. It is currently off market. The Trulia Estimate is $589,100, with a rent estimate of $2,124/month.

Home Details for 799 Upper Dummerston Rd

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: Wall UnitHeating Fuel: Forced Air
Appliances & Utilities
DishwasherRefrigerator
Levels, Entrance, & Accessibility
Floors: Carpet, Hardwood
Room & Shared Space
Shared space is furnished

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 Year

Exterior Features

Exterior Home Features
Garden
Parking & Garage
Parking: Off Street Parking, On Site

Price History for 799 Upper Dummerston Rd

DatePriceEventSource
02/14/2026$2,400ListingRemovedZillow Rentals
12/10/2025$2,400Listed For RentZillow Rentals
07/18/2017$350,000Sold
PrimeMLS #4462578
05/12/2016$399,000ListingRemovedAgent Provided
03/29/2016$399,000PendingAgent Provided
09/29/2015$399,000PriceChange
Agent Provided
06/30/2015$450,000PriceChange
Agent Provided
06/27/2014$485,000PriceChange
Agent Provided
04/12/2014$550,000Listed For SaleAgent Provided

Market trends in Brattleboro

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
32
9MoM
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Property Tax and Assessment

Year2024
Tax
Assessment$366,640
Home facts updated by county records

Comparable Sales for 799 Upper Dummerston Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1082 W River Road, Brattleboro, VT
0.62
Single-Family Home
$305,000
09/23/25
3
1
1,222
1073 Upper Dummerston Road, Brattleboro, VT
0.46
Single-Family Home
$525,000
08/19/25
3
2
2,456
672 East Orchard Street, Brattleboro, VT
0.43
Single-Family Home
$470,000
09/26/25
3
3
3,148
137 Pleasant Valley Road, Brattleboro, VT
0.81
Single-Family Home
$389,000
05/08/26
1
1
650
395 Hillwinds Road, Brattleboro, VT
0.52
Single-Family Home
$668,000
08/12/25
4
2.5
2,226
131 Pleasant Valley Rd, Brattleboro, VT
0.77
Single-Family Home
$15,000
05/13/26
2
1
792
139 Buttonwood Drive, Brattleboro, VT
1.20
Single-Family Home
$455,000
03/04/26
2
2
1,390
155 Upper Dummerston Road, Brattleboro, VT
1.12
Single-Family Home
$407,000
11/21/25
3
1.5
1,655
84 Magnolia Drive, Brattleboro, VT
1.16
Single-Family Home
$570,000
04/29/26
2
2
1,900
387 Meadow Brook Road, Brattleboro, VT
1.11
Single-Family Home
$439,000
05/13/26
4
2
1,568

Nearby homes

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Assigned Schools

These are the assigned schools for 799 Upper Dummerston Rd.
View nearby schools on GreatSchools
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

  • 81 % Say car is needed

  • 80 % Say there's wildlife

  • 72 % Say people would walk alone at night

  • 66 % 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 streets are well-lit

  • 50 % Say there are community events

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

  • 38 % Say it's quiet

Sourced by Trulia users. Learn more about our methodology.
  • Greycella
    "Great neighborhood for learning to ride bikes, trick-or-treating, making friends with other families."
    0
    Flag
  • 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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Apartments for Rent

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Explore by feature - Pet Friendly

10 pet-friendly rentals in Brattleboro, VT

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Explore by feature - Air Conditioning

19 rentals with air conditioning in Brattleboro, VT

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14 rentals with a washer/dryer in Brattleboro, VT

Homes for sale near 799 Upper Dummerston Rd

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Off Market Homes Near 799 Upper Dummerston Rd

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Frequently asked questions about 799 Upper Dummerston Rd

  • What is 799 Upper Dummerston Rd estimated to be worth?
    Trulia's estimated value for 799 Upper Dummerston Rd in Brattleboro, VT is $589,100.
  • What is the price history for 799 Upper Dummerston Rd?
    799 Upper Dummerston Rd in Brattleboro, VT last sold for $350,000 in July 2017.
  • Is Brattleboro a buyer's or seller's market?
    Brattleboro is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Brattleboro?
    Residents describe Brattleboro, VT as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See recently sold homes in Brattleboro, VT.
  • Does 799 Upper Dummerston Rd have air conditioning?
    Yes, 799 Upper Dummerston Rd in Brattleboro, VT has air conditioning.
  • Does 799 Upper Dummerston Rd have parking?
    Yes, 799 Upper Dummerston Rd in Brattleboro, VT has on-site parking.