Listed by Chris Long • BHG Masiello Brattleboro. Bought with Berkley & Veller Greenwood Country.
Off Market Nov 2022 for $370K
$414,368
Est. refi paymentEst. refi$2,355/mo
3
bd
•
2 ba
•
1,404
sq ft
203 Hillwinds Rd, Brattleboro, VT 05301
About this home
This classic dormered cape with attached 2 car garage sits on 1.1 acres and abuts conserved land with woodland trails on hundreds of acres of protected land to explore out the back door. The house features a main floor bedroom and two large upstairs bedrooms with plenty of closet and storage space, two full baths (one per floor), a first-floor office/den, living/dining area with a wood burning fireplace (insert), hardwood floors throughout the main living area, a private back deck and a full walk-out basement that could easily be finished into additional living space. On the outside you'll find a side yard firepit, ample room for a garden, a level front yard and the paved driveway. HILLWINDS is one of the more sought-after locations in the area in which to live mainly due to its unique combination of close proximity to downtown (5 min), exposure and elevation and the sense of rural country living, and peaceful quiet living normally found much further from town. Perhaps the greatest attribute is the hundreds of acres of conserved land that abuts the parcel. Not only is there direct access to the trail that winds through the large protected common land tract out back but the property also enjoys the view across the street of the 30 plus acre agricultural field owned by the Retreat Farm and other conserved land creating a situation that cannot change with the times. This is truly a special spot to call home.
Single-familyProperty Type
1976Year Built
1.09 acresLot Size
$295Est. Price/Sq.Ft.
2 car garageParking
Listed by Chris Long• BHG Masiello Brattleboro
Bought with Dan Normandeau• Berkley & Veller Greenwood Country
Located in one of Brattleboroâs most desirable neighborhoods and sitting on over an acre of land is this wonderful cape style home. The house boasts of a welcoming living/dining room combination featuring a brick hearth fireplace and a sliding glass door that opens to a large deck. The convenient kitchen has its own door to the deck so that grill isnât far away. Thereâs a first floor full bath and bedroom and office/study room. Upstairs, features 2 large bedrooms and another full bath. An attached 2 car garage tops off this offering. The property abuts the Hillwinds Conservation Area, over 200 acres of conserved land with hiking trails through out. A gem waiting for the next owner.
Year
Property tax
Land + Additions
Assessment*
2025
$4,324 (−1.9%)
$67,000 + $160,670
$227,670
2024
$4,407 (+20.6%)
$67,000 + $160,670
$227,670
2023
$3,655 (−44.9%)
$67,000 + $160,670
$227,670
2022
$6,630 (−0.9%)
$67,000 + $160,670
$227,670
2021
$6,692 (+1.3%)
$67,000 + $160,670
$227,670
2020
$6,606 (−0.1%)
$67,000 + $160,670
$227,670
2019
$6,615 (+1.6%)
$67,000 + $160,670
$227,670
2018
$6,508 (+1.4%)
$67,000 + $160,670
$227,670
2017
$6,418 (+5.3%)
$67,000 + $160,670
$227,670
2016
$6,094 (−5.7%)
$67,000 + $160,670
$227,670
2015
$6,460 (+42.4%)
$67,000 + $160,670
$227,670
2014
$4,537
$67,000 + $160,670
$227,670
Tax history for 203 Hillwinds Rd
Year
Property tax
Land + Additions
Assessment*
2025
$4,324 (−1.9%)
$67,000 + $160,670
$227,670
2024
$4,407 (+20.6%)
$67,000 + $160,670
$227,670
2023
$3,655 (−44.9%)
$67,000 + $160,670
$227,670
2022
$6,630 (−0.9%)
$67,000 + $160,670
$227,670
2021
$6,692 (+1.3%)
$67,000 + $160,670
$227,670
2020
$6,606 (−0.1%)
$67,000 + $160,670
$227,670
2019
$6,615 (+1.6%)
$67,000 + $160,670
$227,670
2018
$6,508 (+1.4%)
$67,000 + $160,670
$227,670
2017
$6,418 (+5.3%)
$67,000 + $160,670
$227,670
2016
$6,094 (−5.7%)
$67,000 + $160,670
$227,670
2015
$6,460 (+42.4%)
$67,000 + $160,670
$227,670
2014
$4,537
$67,000 + $160,670
$227,670
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Public record
Zoning
Beds
3
Baths
2
Stories
2
Lot width
—
Lot depth
—
Lot size
1.1 Acres
Year renovated
—
Sq. Ft.
1,404
Year built
1976
Style
Single Family Residential
County
Windham County
APN
08102514413
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 8, 2026.
RR
Rural Residential District
The Rural Residential District encompasses land primarily west of Interstate 91 that is rural in character but is relatively close to the developed areas of town and accessible from improved public roads, which has made these areas a suitable and attractive location for low-density residential development. This land is generally not served by municipal water and sewer, and extension of infrastructure into this district is discouraged. The purpose of this district is to provide opportunities for rural housing and to encourage thoughtful siting of new development in order to protect rural character, farmland, forestland, open space and important natural resources in accordance with the policies of the Brattleboro Town Plan.
Permitted uses
Include but are not limited to:
Agriculture
Religious facility
Housing-Single unit
Housing-Multiple units
Housing-Senior
Infrastructure
Golf related
Cemetery
Park & open space
Timberland
Property details
Parking
Parking & Garage
Garage Capacity: 2
Location: Attached
Direct Entry
Interior
Virtual Tour
Bathroom Information
# of Baths (full): 2
Basement Information
Basement: Yes
Basement Access: Walkout
Concrete, Full, Walkout, Exterior Access
Other Interior Features
# of Rooms: 7
Flooring: Carpet, Hardwood
Water Heater: Off Boiler
Fireplace - Wood, Hearth
Equipment & Appliance Information
Dishwasher, Dryer, Range - Gas, Refrigerator, Washer
Room 1 Information
Kitchen
Kitchen
Dimensions: 10' X 11'
Level: 1
Room 2 Information
Dining Room
Dimensions: 9'6" X 9'6"
Level: 1
Room 3 Information
Living Room
Dimensions: 14' X 15'
Level: 1
Room 4 Information
Bedroom
Dimensions: 11'6" X 12'
Level: 1
Room 5 Information
Office/Study
Dimensions: 9' X 11'
Level: 1
Room 6 Information
Bedroom
Bedroom
Dimensions: 14' X 14'
Level: 2
Room 7 Information
Bedroom
Dimensions: 14' X 18'
Level: 2
Exterior
Building Information
Construction Status: Existing
Approximate Sq. Ft. Total Finished: 1404
Approximate Sq. Ft. Total: 2340
Color: White
Deck, Garden Space
Construction: Wood Frame
Foundation: Poured Concrete
Roof: Shingle - Asphalt
Exterior: Clapboard, Combination
Driveway
Paved
Lot, Zoning, & Easement Information
Common Land Acres: 209
Conserved Land, Country Setting, Rolling, Trail/Near Trail, Walking Trails
Survey Information
Surveyed: Yes
Other Property & Lot Information
Year Built: 1976
Financial
Assessment Information
Assessment Amount: 227670
Assessment Year: 2022
Tax Information
Tax Year: 2022
Gross Amount Tax: 6629.96
SPAN Number: 081-025-14413
Other Tax Information
Page Deed: 205
Utilities
Heating & Cooling Information
Heat: Baseboard, Hot Water, Stove - Wood
Heat Fuel: Oil, Wood
Sewer Information
On-Site Septic Exists, Private
Electric Information
100 Amp
Water Information
Drilled Well
Other Utilities Information
Cable - At Site, High Speed Intrnt -AtSite
Location
Neighborhood Information
Abuts Conservation, Near Country Club, Near Golf Course, Near Shopping, Near Skiing, Neighborhood, Rural, Near Public Transportatn, Near Hospital
Road Information
Road Frontage: Yes
Road Frontage Length: 175
Dead End, Paved, Public
Other Location Information
Directions: From Upper Dummerston Road take Hillwinds Road to 203 on right at the top of the hill.
Public facts
Beds: 3
Baths: 2.0
Sq. Ft.: 1,404
Stories: 2.0
Lot Size: 1.1 acres
Style: Single Family Residential
Year Built: 1976
Year Renovated: —
County: Windham County
APN: 08102514413
Home facts updated by county records on Jul 8, 2026