585 E Orchard St, Brattleboro, VT 05301
Property image
Property image
OFF MARKET

$832,500

Trulia Estimate
  • 4 Beds
  • 4.5 Baths
  • 4,686 sqft (on 2.06 acres)

585 E Orchard St, Brattleboro, VT 05301

Est. Refi. Payment $5,608/mo*
Refinance Your Home
Currently Off Market - Sold Dec 18, 2020 for $575,000

Home Value

Trulia Estimate
$833K
Since last month
Decreased$20K (-2.3%)
Since last year
Decreased$32K (-3.7%)
Since last sale
Increased$255K (+44.3%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +76% in the last 10 years
MonthEstimated value
2026
August 2026$830K
August 2026$830K
July 2026$849K
June 2026$860K
May 2026$856K
April 2026$842K
March 2026$839K
February 2026$820K
January 2026$823K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
672 East Orchard Street, Brattleboro, VT
0.21
Single-Family Home
$470,000
09/26/25
3
3
3,148
23 Meetinghouse Lane, Brattleboro, VT
0.74
Single-Family Home
$495,000
12/29/25
3
2.5
3,415
204 Meetinghouse Lane, Brattleboro, VT
1.05
Single-Family Home
$497,408
04/10/26
4
2
2,656
387 Meadow Brook Road, Brattleboro, VT
0.62
Single-Family Home
$439,000
05/13/26
4
2
1,568
11 Strawberry Hill, Brattleboro, VT
1.42
Single-Family Home
$580,000
06/30/26
4
2.5
2,573
10 Ethan Hill, Brattleboro, VT
1.15
Single-Family Home
$447,700
12/08/25
3
2.5
2,399
187 Hillwinds Road, Brattleboro, VT
1.36
Single-Family Home
$476,000
11/20/25
4
3
2,372
65 Hillwinds North Road, Brattleboro, VT
1.54
Single-Family Home
$925,000
10/01/25
5
4.5
4,150
65 Hillwinds N, Brattleboro, VT
1.55
Single-Family Home
$925,000
10/06/25
5
5
4,150
143 Hillwinds Road, Brattleboro, VT
1.42
Single-Family Home
$615,000
06/26/26
5
3.5
2,520

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
0 Gibson Road Lot #56, Brattleboro, VT 05301
0.11
-
-
-
-
Off Market
0 East Orchard Street, Brattleboro, VT 05301
0.14
-
-
-
-
Off Market
672 East Orchard Street, Brattleboro, VT 05301
0.21
$492,100
3
3
3,148
Off Market
396 East Orchard Street, Brattleboro, VT 05301
0.32
$787,400
4
5
4,300
Off Market
0 Orchard Street Lot 59, Brattleboro, VT 05301
0.45
$70,000
-
-
-
Recently Sold
94 Brets Road, Brattleboro, VT 05301
0.52
$475,000
3
2.5
2,594
Recently Sold
387 Meadow Brook Road, Brattleboro, VT 05301
0.62
$439,000
4
2
1,568
Recently Sold
863 Upper Dummerston Road, Brattleboro, VT 05301
0.65
$579,700
3
2.5
2,112
Off Market
680 West River Road, Brattleboro, VT 05301
0.67
$145,000
-
-
-
Recently Sold
Lot #4 Bittersweet Lane, Brattleboro, VT 05301
0.71
-
-
-
-
Off Market
137 Pleasant Valley Road, Brattleboro, VT 05301
0.69
$389,000
1
1
650
Recently Sold
Lot #5 Bittersweet Lane, Brattleboro, VT 05301
0.74
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 585 E Orchard St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2005
Lot Size
2.06 acres
Living Area
4,686 sqft
Price/Sqft
$178
Parking
Garage

About this House

This single-family home is located at 585 E Orchard St, Brattleboro, VT. 585 E Orchard St is in Brattleboro, VT and in ZIP code 05301. This property has 4 bedrooms, 5 bathrooms and approximately 4,686 sqft of floor space. This property has a lot size of 2.06 acres and was built in 2005.
585 E Orchard St, Brattleboro, VT 05301 is a 4 bedroom, 5 bathroom, 4,686 sqft single-family home built in 2005. It last sold for $575,000 on Dec 18, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $832,500, with a rent estimate of $5,530/month.

Home Details for 585 E Orchard St

Interior Features

Heating & Cooling
Heating: Baseboard, Radiant, Gas, Wood PelletHeating Fuel: Baseboard
Interior Details
Number of Rooms: 11Types of Rooms: Walk In Closet, Dining Room, Family Room, Mud Room, Office
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows
Levels, Entrance, & Accessibility
Floors: Tile, Carpet, Hardwood, Laminate, Linoleum Vinyl
Security
Security System

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: OtherGardenPatio
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 2005
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Lot Information

Lot Area: 2.06 acres

Price and Tax history

DateEventPrice
Dec 18, 2020
Source: PrimeMLS #4807794
Sold
$575,000
Aug 1, 2020
Source: Agent Provided
PriceChange
$599,000
Price decreased by 4%
May 29, 2020
Source: Agent Provided
Listed For Sale
$625,000
Oct 14, 2014
Source: N/A
Sold
$455,000
Aug 27, 2014
Source: Agent Provided
PriceChange
$469,000
Price decreased by 6%

Market trends in Brattleboro

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
32

Around this home

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

LGBTQ Local Legal Protections

Frequently asked questions about 585 E Orchard St

  • What is 585 E Orchard St estimated to be worth?
    Trulia's estimated value for 585 E Orchard St in Brattleboro, VT is $832,500.
  • What is the price history for 585 E Orchard St?
    585 E Orchard St in Brattleboro, VT last sold for $575,000 in December 2020.
  • 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 585 E Orchard St have laundry facilities?
    Yes, 585 E Orchard St in Brattleboro, VT has in-unit laundry.
  • How big is the lot at 585 E Orchard St?
    The lot at 585 E Orchard St in Brattleboro, VT is about 2.1 acres.

Explore by feature - Pet Friendly

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Off Market Homes Near 585 E Orchard St

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