396 East Orchard Street, Brattleboro, VT 05301
Property image
Property image
OFF MARKET
Listed by Kathy Dowd, Bellville Realty, (802) 257-7979 . Bought with Engel & Volkers Okemo

396 East Orchard Street
Brattleboro, VT 05301

  • 4 Beds
  • 5 Baths
  • 4,300 sqft (on 4 acres)

$808,100

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $5,527/mo*
Refinance Your Home

$808,100

Trulia Estimate
as of Aug 8, 2026
Est. Refi. Payment $5,527/mo*
Refinance Your Home
4 Beds
5 Baths
4,300 sqft
(on 4 acres)

Local Information

  • Map ViewExplore the area around 396 East Orchard Street.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1985
Lot Size
4 acres
Living Area
4,300 sqft
Price/Sqft
$188
Last check for updates: about 2 hours ago
Listed by Kathy Dowd
Bellville Realty, (802) 257-7979
Bought with: Mendi Michael, Engel & Volkers Okemo, (802) 975-0338
Source: PrimeMLS, MLS#4953757

About this House

Lifestyle choices! This distinctive contemporary is situated on a country road with stately maple trees on the front lawn, an antique barn and four acres of tree lined meadows bordered on two sides by conserved land of the Retreat Farm. Designed and built by the owner as a single family residence it is currently arranged as a duplex, a home for her with rental income. Designed to be easily returned to its original 4 bedroom, 5 bathroom one family home it offers lifestyle choices for now and later. There is a separately deeded and surveyed two acre unimproved lot for future needs! The antique barn is ready for restoration. The Brattleboro Country Club golf course is across the road and shopping, schools and vibrant downtown Brattleboro are minutes away. Pictures show owner's residence on left side of house. On right side on the first level is a large open kitchen and dining area with glass doors to back deck, a living room and a 3/4 bath, upstairs are two bedrooms and a full bath. Laundry area and office in finished basement. Showings begin on Saturday May 27, 2023.
396 East Orchard Street, Brattleboro, VT 05301 is a 4 bedroom, 5 bathroom, 4,300 sqft single-family home built in 1985. It last sold for $750,000 on Aug 7, 2023 (3% above the $727,000 asking price). It is currently off market. The Trulia Estimate is $808,100, with a rent estimate of $4,673/month.

Home Details for 396 East Orchard Street

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: Bulkhead,Concrete,Concrete Floor,Full,Interior Access,Basement Stairs,Interior EntryNumber of Rooms: 13
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 5Number of Bathrooms (full): 2Number of Bathrooms (three quarters): 3
Dimensions and Layout
Living Area: 4300 Square Feet
Appliances & Utilities
Utilities: Cable Available, Underground Utilities, Underground Oil TankAppliances: Electric Water Heater
Heating & Cooling
Heating: Oil,Baseboard,Hot WaterNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Oil
Gas & Electric
Electric: 100 Amp Service, 200+ Amp Service
Levels, Entrance, & Accessibility
Stories: 2Levels: Two
View
No View

Exterior Features

Exterior Home Features
Roof: Asphalt ShingleFoundation: Concrete
Parking & Garage
No GarageParking: Gravel
Frontage
Road Frontage: PublicRoad Surface Type: Gravel
Water & Sewer
Sewer: 1250 Gallon, Mound Septic, Septic Tank
Farm & Range
Frontage Length: Road frontage: 463
Finished Area
Finished Area (above surface): 3530 Square FeetFinished Area (below surface): 770 Square Feet

Property Information

Year Built
Year Built: 1985
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Contemporary
Building
Construction Materials: Wood Frame, Combination Exterior, Stone Exterior, Wood ExteriorNot a New Construction

Price & Status

Price
List Price: $727,000

Location

Direction & Address
City: Brattleboro
School Information
Elementary School: Brattleboro Elem SchoolsElementary School District: Brattleboro School DistrictJr High / Middle School: Brattleboro Area Middle SchoolJr High / Middle School District: Brattleboro School DistrictHigh School: Brattleboro High SchoolHigh School District: Brattleboro School District

Building

Building Area
Building Area: 4300 Square Feet

Lot Information

Lot Area: 4 Acres

Miscellaneous

BasementMls Number: 4953757Above Grade Unfinished Area: 3530Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area Source: OtherBelow Grade Unfinished Area Units: Square Feet

Price History for 396 East Orchard Street

DatePriceEventSource
08/07/2023$750,000Sold
PrimeMLS #4953757
06/18/2023$727,000ContingentPrimeMLS #4953757
05/22/2023$727,000Listed For SalePrimeMLS #4953757

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$429,080
Home facts updated by county records

Comparable Sales for 396 East Orchard Street

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
23 Meetinghouse Lane, Brattleboro, VT
0.47
Single-Family Home
$495,000
12/29/25
3
2.5
3,415
672 East Orchard Street, Brattleboro, VT
0.52
Single-Family Home
$470,000
09/26/25
3
3
3,148
10 Ethan Hill, Brattleboro, VT
0.86
Single-Family Home
$447,700
12/08/25
3
2.5
2,399
204 Meetinghouse Lane, Brattleboro, VT
0.76
Single-Family Home
$497,408
04/10/26
4
2
2,656
11 Strawberry Hill, Brattleboro, VT
1.11
Single-Family Home
$580,000
06/30/26
4
2.5
2,573
387 Meadow Brook Road, Brattleboro, VT
0.60
Single-Family Home
$439,000
05/13/26
4
2
1,568
395 Hillwinds Road, Brattleboro, VT
1.30
Single-Family Home
$668,000
08/12/25
4
2.5
2,226
155 Upper Dummerston Road, Brattleboro, VT
0.89
Single-Family Home
$407,000
11/21/25
3
1.5
1,655
65 Hillwinds North Road, Brattleboro, VT
1.86
Single-Family Home
$925,000
10/01/25
5
4.5
4,150

Nearby homes

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Assigned Schools

These are the assigned schools for 396 East Orchard Street.
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

8 pet-friendly rentals in Brattleboro, VT

Explore by feature - Air Conditioning

13 rentals with air conditioning in Brattleboro, VT

Explore by feature - Washer/dryer

11 rentals with a washer/dryer in Brattleboro, VT

Homes for sale near 396 East Orchard Street

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Off Market Homes Near 396 East Orchard Street

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Frequently asked questions about 396 East Orchard Street

  • What is 396 East Orchard Street estimated to be worth?
    Trulia's estimated value for 396 East Orchard Street in Brattleboro, VT is $808,100.
  • What is the price history for 396 East Orchard Street?
    396 East Orchard Street in Brattleboro, VT last sold for $750,000 in August 2023.
  • 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.
  • How big is the lot at 396 East Orchard Street?
    The lot at 396 East Orchard Street in Brattleboro, VT is about 4 acres.
  • Does 396 East Orchard Street have parking?
    Yes, 396 East Orchard Street in Brattleboro, VT has on-site parking.
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 2026-08-07 16:44:51 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.