559 Upper Dummerston Rd

2,536 Sq. Ft.
$130 / Sq. Ft.
2,536
Sq. Ft.
$130
per Sq. Ft.

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...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!
  1. Listed by Robert Doyle • Berkley & Veller Greenwood Country • Off: 802-254-6400

Sold By BHG Masiello Brattleboro

Property Details for 559 Upper Dummerston Road

Parking
Auto Open, Direct Entry, Parking Spaces 2, Underground
Zoning
R1
LISTING CLOSED: 06/25/2015 12:00 AM

Property Details for 559 Upper Dummerston Road

StatusClosed
MLS #4348671
Days on Market407
Taxes$8,891 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family
Year Built1960
Lot Size0.48 AC / 20,908 SF
CountyWindham County

Location

Add your commute

Building Information for 559 Upper Dummerston Road

Stories1Year Built1960Building Size-Lot Size0.48 AC / 20,908 SF

Payment Calculator

$2,416 per month

30 year fixed, 6.55% Interest

Principal and Interest

$1,675

Property Taxes

$741

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 559 Upper Dummerston Road

Summary
Location and General Information
  • City: Brattleboro
  • County: VT-Windham
  • Directions: Route 30 North from Brattleboro. Turn left onto Upper Dummerston Road. House on the right across from The Country Club. See sign.
  • Latitude: 42.875917333209
  • Longitude: -72.585510527028
  • Road Frontage: Yes
  • Seasonal: No
  • State: VT
  • Zip Code: 05301
Taxes and HOA Information
  • SPAN Number: 08102511809
  • Tax Year: 2014
  • Taxes TBD: No
Parking
  • Garage: Yes
  • Garage Capacity: 2.00
  • Driveway: Paved
Property
Lot Information
  • Lot - Sqft: 20908.0
  • Lot Features: Country Setting, Landscaped, Mountain View, View
  • Lot Size Acres: 0.48
  • Road Frontage Length: 151.0
  • Square Feet Apx Finished Above Grade: 2270.0
  • Square Feet Apx Finished Below Grade: 266.0
  • Square Feet Apx Tot Below Grade: 2000.0
  • Square Feet Apx Total Finished: 2536.0
  • Square Feet Apx Unfinished Below Grade: 1734.0
Property and Assessments
  • Property Class: Residential
  • Property Type: Single Family
  • Construction Status: Existing
  • Flood Zone: Unknown
  • Foundation: Concrete
  • Surveyed: Yes
  • Year Built: 1960
Utilities
  • Electric: 100 Amp, Circuit Breaker(s)
  • Sewer: 1000 Gallon, Septic
  • Water Source: Drilled Well
  • Internet: DSL
Interior and Exterior Features
Exterior Features
  • Construction Materials: Wood Frame, Clapboard Exterior
  • Features - Accessibility: 1st Floor Bedroom, 1st Floor Full Bathroom
  • Features - Exterior: Deck, Outbuilding, Porch - Covered
  • Roof: Shingle - Asphalt
Interior Features
  • Appliances: Cooktop - Gas, Dishwasher, Dryer, Range Hood, Microwave, Other, Oven - Wall, Refrigerator, Washer, Stove - Gas, Water Heater - Domestic
  • Basement: Yes
  • Basement Access Type: Walkout
  • Basement Description: Concrete, Full, Partially Finished, Stairs - Interior, Storage Space
  • Baths - Total: 2
  • Baths - Full: 2
  • Half Baths: 0
  • One Quarter Baths: 0
  • Three Quarter Bath: 0
  • Rooms - Total: 8
  • Bedrooms - Total: 3
  • Equipment: CO Detector, Radon Mitigation, Satellite Dish, Smoke Detector
  • Features - Interior: Cathedral Ceiling, Ceiling Fan, Dining Area, Fireplace - Wood, Fireplaces - 1, Hearth, Kitchen/Family, Primary BR w/ BA
  • Flooring: Carpet, Ceramic Tile, Hardwood
  • Heating: Propane, Oil, Pellet Stove, Alternative Heat Stove, Baseboard, Hot Water, Other, Stove, Stove - Gas, Stove - Pellet
  • Cooling: Other
  • Total Stories: 1
Room Information
Room 1
  • Room Dimensions: 32X18 Irreg.
  • Room Level: 1
  • Room Type: Kitchen
Room 2
  • Room Dimensions: 15X15
  • Room Level: 1
  • Room Type: Dining Room
Room 3
  • Room Dimensions: 16X20.5
  • Room Level: 1
  • Room Type: Living Room
Room 4
  • Room Dimensions: In Kitchen
  • Room Level: 1
  • Room Type: Family Room
Room 5
  • Room Dimensions: 14X19
  • Room Level: Basement
  • Room Type: Office/Study
Room 7
  • Room Dimensions: 18X13'6"
  • Room Level: 1
  • Room Type: Primary Bedroom
Room 8
  • Room Dimensions: 10'2X17'6"
  • Room Level: 1
  • Room Type: Bedroom
Room 9
  • Room Dimensions: 15'8"X14
  • Room Level: 1
  • Room Type: Bedroom
Room 13
  • Room Dimensions: 16X17'8"
  • Room Level: 1
  • Room Type: Other

Property History for 559 Upper Dummerston Road

DateEvent & SourcePriceAppreciation
Jun 29, 2015

Sold (Public Record)

Public Record #551433770

$329,500

+0.5% / yr

Jun 25, 2015

Sold

New England Real Estate Network #4348671

$329,500—
Jun 25, 2015

Pending

New England Real Estate Network #4348671

—
DateEvent & SourcePrice
06/29/2015

Sold (Public Record)

Public Record #551433770

$329,500

+0.5% / yr

06/25/2015

Sold

New England Real Estate Network #4348671

$329,500
06/25/2015

Pending

New England Real Estate Network #4348671

—

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 559 Upper Dummerston Road

Taxable ValueLand$49,000Additions$294,540Total$343,540
Tax Record2024$11,155 ($930 / month)
Home Facts
Beds3Baths2Total Finished SqFt2,186 SqFtAbove Grade Finished SqFt2,186 SqFtStories1Lot Size20,909 SqFtStyleSingle Family ResidenceYear Built1963ZoningRRCountyWINDHAMAPN(025) 00070334.000

Schools near 559 Upper Dummerston Road

This home is within Windham Southeast Unified Union School District #96.
Rating
School
Type
Grades
Distance
Public - PK to 6
Public - 7 to 8
Public - 9 to 12
Public - 9 to 12
Rating
School
Distance
Canal Street/Oak Grove Schools
PublicPK to 6

Brattleboro Area Middle School
Public7 to 8

Brattleboro Senior Uhsd #6
Public9 to 12

Windham Regional Career Center
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Berkley & Veller Greenwood Country

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site 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 07/26/2026 09:08 AM