Sold
Last Sold Price
3 beds2,180 sqft$124/sqft
357 Hillwinds Rd, Brattleboro, VT 05301
Single FamilyProperty Type
1.5 acresLot Size
1997Year Built
$124/sq ftPrice per sq ft
2 carsParking Spaces

Description

Tucked back from the road, surrounded by woodland and bordering conserved land, is this Japan-influenced, passive-solar home, designed with clean, simple lines, a close connection to nature, and light-filled rooms from plentiful windows and carefully placed skylights. The main floor open-concept living/dining/kitchen area has large open spaces, lovely birch flooring warmed by radiant heat, walls of windows, and a three-sided central fireplace. There is a master bedroom, a bath with clawfoot tub and...Tucked back from the road, surrounded by woodland and bordering conserved land, is this Japan-influenced, passive-solar home, designed with clean, simple lines, a close connection to nature, and light-filled rooms from plentiful windows and carefully placed skylights. The main floor open-concept living/dining/kitchen area has large open spaces, lovely birch flooring warmed by radiant heat, walls of windows, and a three-sided central fireplace. There is a master bedroom, a bath with clawfoot tub and a 12x25 screened porch overlooking the woods--perfect for warm weather meals, yoga, and bird watching. The lower level has 2 bedrooms, bath, laundry and a huge family room or studio with a woodstove hookup and radiant heat. All the lower level rooms are walk-out and bright, with sliders overlooking the conserved woodlands with miles of hiking and groomed x-c ski trails. Excellent downhill skiing is only 30 minutes away. The house design provides passive solar and passive cooling which is supplemented by a new photovoltaic--solar panel--system. This is a remarkable, inviting home in a desirable location that is both private and convenient. The Hillwinds area, on the edge of Brattleboro, offers a strong community, and is a wonderful place to raise children, walk your dog, and get to know your friendly neighbors.

    Sold By Berkley & Veller Greenwood Country

    • Listed by: John Hatton • Berkley & Veller Greenwood Country
    Listing closed: 12/27/2018 12:00 AM • Source: New England Real Estate Network, MLS#: 4722950

    Recent comparable sales

    Median sold price

    $325,000

    Avg days on market

    51

    Sale-to-list ratio

    96.2%

    Brattleboro, VT

    9 comparable properties found

    $315,000 | 106 Western Avenue, Brattleboro, VT 05301
    1/39
    1

    $315,000

    Sold 01/03/25

    3
    Bedrooms
    2,061
    Square Feet
    0.1
    Acres
    $315,000 | 334 Carriage Hill Road, Brattleboro, VT 05301
    1/26
    2

    $315,000

    Sold 02/28/25

    3
    Bedrooms
    1,971
    Square Feet
    0.36
    Acres
    $320,000 | 1089 Marlboro Road, Brattleboro, VT 05301
    1/31
    3

    $320,000

    Sold 07/31/26

    3
    Bedrooms
    1,703
    Square Feet
    0.56
    Acres
    $310,000 | 34 Hampshire Circle, Brattleboro, VT 05301
    1/34
    4

    $310,000

    Sold 07/03/25

    3
    Bedrooms
    1,666
    Square Feet
    0.29
    Acres
    $325,000 | 184 Carriage Hill Road, Brattleboro, VT 05301
    1/44
    5

    $325,000

    Sold 08/20/26

    3
    Bedrooms
    1,272
    Square Feet
    0.32
    Acres
    $370,000 | 115 Country Hill, Brattleboro, VT 05301
    1/25
    6

    $370,000

    Sold 04/02/26

    3
    Bedrooms
    1,820
    Square Feet
    0.36
    Acres
    $350,000 | 113 Stockwell Drive, Brattleboro, VT 05301
    1/34
    7

    $350,000

    Sold 04/01/25

    3
    Bedrooms
    1,754
    Square Feet
    0.36
    Acres
    $590,000 | 299 Sunset Lake Road, Brattleboro, VT 05301
    1/43
    8

    $590,000

    Sold 05/18/26

    3
    Bedrooms
    1,995
    Square Feet
    10.01
    Acres
    $325,000 | 91 Sunny Acres Road, Brattleboro, VT 05301
    1/33
    9

    $325,000

    Sold 12/30/25

    3
    Bedrooms
    1,890
    Square Feet
    0.22
    Acres

    Location

    Add your commute

    Payment Calculator

    $2,028 per month

    30 year fixed, 6.55% Interest

    Principal and Interest

    $1,372

    Property Taxes

    $656

    HOA Dues

    $0

    The Payment Calculator is for illustrative purposes only.

    Know your buying power with a preapproval and custom rate in minutes

    Rocket Mortgage1

    Property Information for 357 Hillwinds Road

    Property Details
    • Taxes: $7,866 / year
    • MLS Type: Residential / Single Family
    • Parking: Driveway, Garage
    • Zoning: Rural residential
    Building Information
    • Stories: 1
    • Year Built: 1997
    • Lot Size: 1.50 AC / 65,340 SF
    Summary
    Location and General Information
    • City: Brattleboro
    • County: VT-Windham
    • Directions: Rt. 30 to Upper Dummerston Rd. to Hillwinds. #357, see sign.
    • Latitude: 42.885674000000023
    • Longitude: -72.598840542327878
    • Mount Location: Roof
    • Mount Type: Fixed Rack
    • Road Frontage: Yes
    • Seasonal: No
    • State: VT
    • Street Designation: Road
    • Zip: 05301
    Taxes and HOA Information
    • SPAN Number: 081-025-15688
    • Tax - Gross Amount: $7,866.00
    • Tax Year: 2018
    • Taxes TBD: No
    School Information
    • School - High: Brattleboro High School
    • School - District: Brattleboro School District
    • School - Elementary: Brattleboro Elem Schools
    • School - Middle/Jr: Brattleboro Area Middle School
    Parking
    • Garage: Yes
    • Garage Capacity: 2.00
    • Driveway: Gravel
    Property
    Lot Information
    • Lot - Sqft: 65340.0
    • Lot Size Acres: 1.5
    • Road Frontage Length: 180.0
    • Square Feet Apx Finished Above Grade: 1380.0
    • Square Feet Apx Finished AG Source: Public Records
    • Square Feet Apx Finished Below Grade: 800.0
    • Square Feet Apx Finished BG Source: Public Records
    • Square Feet Apx Total: 2760.0
    • Square Feet Apx Total Finished: 2180.0
    • Square Feet Apx Unfinished Above Grade: 0.0
    • Square Feet Apx Unfinished AG Source: Public Records
    • Square Feet Apx Unfinished Below Grade: 580.0
    • Square Feet Apx Unfinished BG Source: Public Records
    Property and Assessments
    • Current Use: No
    • Property Class: Residential
    • Property Type: Single Family
    • Flood Zone: No
    • Foundation: Concrete, Poured Concrete
    • Power Production Ownership: Seller Owned
    • Power Production Type: Photovoltaics
    • Power Production Year Install: 2017
    • PreConstruction: No
    • Resort: No
    • ROW - Parcel Access: No
    • Surveyed: Unknown
    • Year Built: 1997
    Utilities
    • Electric: 100 Amp, Circuit Breaker(s)
    • Sewer: Leach Field, Septic
    • Utilities: Internet - Cable
    Interior and Exterior Features
    Exterior Features
    • Color: Brown
    • Features - Exterior: Porch - Screened, Windows - Double Pane
    • Roads: Paved, Public
    • Roof: Shingle - Asphalt
    Interior Features
    • Basement: Yes
    • Basement Access Type: Interior
    • Basement Description: Concrete Floor, Partially Finished, Walkout
    • Baths - Total: 2
    • Baths - Full: 2
    • Half Baths: 0
    • One Quarter Baths: 0
    • Three Quarter Bath: 0
    • Rooms - Total: 7
    • Rooms: Level 1: Level 1: Bath - Full, Level 1: Dining Room, Level 1: Kitchen, Level 1: Living Room, Level 1: Master Bedroom, Level 1: Other, Level 1: Porch
    • Rooms: Level B: Level B: Bedroom, Level B: Bath - Full, Level B: Den
    • Bedrooms - Total: 3
    • Features - Interior: Dining Area, Walk-in Pantry
    • Flooring: Concrete, Hardwood
    • Heat Fuel: Gas - LP/Bottle
    • Heating: Hot Water, Radiant
    • Cooling: None
    • Total Stories: 1
    Room Information
    Room 1
    • Room Dimensions: 11'2 x 17'1
    • Room Level: 1
    • Room Type: Kitchen
    Room 2
    • Room Dimensions: 163 x 14'11.5
    • Room Level: 1
    • Room Type: Dining Room
    Room 3
    • Room Dimensions: 24'9 x 12'9.75
    • Room Level: 1
    • Room Type: Living Room
    Room 5
    • Room Dimensions: 17'11.5 x 29'4.75
    • Room Level: Basement
    • Room Type: Den
    Room 6
    • Room Dimensions: 7'2.5 x 3'5.75
    • Room Level: 1
    • Room Type: Other
    Room 7
    • Room Dimensions: 10' x 32'
    • Room Level: 1
    • Room Type: Porch
    Room 10
    • Room Dimensions: 15'7 x 18'5.75
    • Room Level: 1
    • Room Type: Master Bedroom
    Room 11
    • Room Dimensions: 10'5 x 10'8.5
    • Room Level: Basement
    • Room Type: Bedroom
    Room 12
    • Room Dimensions: 13'1 x 10'5
    • Room Level: Basement
    • Room Type: Bedroom
    Room 16
    • Room Dimensions: 9'9.25 x 9
    • Room Level: 1
    • Room Type: Bath - Full
    Room 17
    • Room Dimensions: 8'3 x 8'6
    • Room Level: Basement
    • Room Type: Bath - Full

    Property History for 357 Hillwinds Road

    DateEvent & SourcePriceAppreciation
    Dec 28, 2018

    Sold (Public Record)

    Public Record #638532766

    $270,000

    +0.9% / yr

    Dec 27, 2018

    Sold

    New England Real Estate Network #4722950

    $270,000
    Oct 10, 2018

    Listed (Active)

    New England Real Estate Network #4722950

    $297,000
    DateEvent & SourcePrice
    12/28/2018

    Sold (Public Record)

    Public Record #638532766

    $270,000

    +0.9% / yr

    12/27/2018

    Sold

    New England Real Estate Network #4722950

    $270,000
    10/10/2018

    Listed (Active)

    New England Real Estate Network #4722950

    $297,000

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

    Public Records for 357 Hillwinds Road

    Taxable ValueLand$75,000Additions$200,180Total$275,180
    Tax Record2025$4,826 ($402 / month)
    Home Facts
    Beds1Baths2Total Finished SqFt1,380 SqFtAbove Grade Finished SqFt1,380 SqFtStories1Lot Size65,340 SqFtStyleSingle Family ResidenceYear Built1997Year Renovated1997ZoningRR / RCountyWINDHAMAPN(025) 00070170.000

    Schools near 357 Hillwinds 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 - PK to 6
    Rating
    School
    Distance
    Academy School
    PublicPK to 6

    Brattleboro Area Middle School
    Public7 to 8

    Brattleboro Senior Uhsd #6
    Public9 to 12

    Green Street School
    PublicPK to 6

    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.

    Similar Homes

    New listings in 05301

    $250,000 | 556 South Main Street, Brattleboro, VT 05301
    1/5

    $250,000

    6
    Bedrooms
    2,112
    Square Feet
    0.15
    Acres
    $350,000 | 10 Birge Street, Brattleboro, VT 05301

    $350,000

    5
    Bedrooms
    3,002
    Square Feet
    0.15
    Acres
    $350,000 | 573 South Main Street, Brattleboro, VT 05301

    $350,000

    2
    Bedrooms
    3,312
    Square Feet
    0.65
    Acres
    $380,000 | 25 Cottage Street, Brattleboro, VT 05301
    1/5

    $380,000

    6
    Bedrooms
    3,264
    Square Feet
    0.15
    Acres
    $225,000 | 16 Washington Street, Brattleboro, VT 05301
    1/32

    $225,000

    4
    Bedrooms
    2,209
    Square Feet
    0.21
    Acres
    $225,000 | 16 Washington Street, Brattleboro, VT 05301
    1/33

    $225,000

    5
    Bedrooms
    2,209
    Square Feet
    0.21
    Acres
    $899,800 | 925 Hinesburg Road, Brattleboro, VT 05301
    1/51

    $899,800

    5
    Bedrooms
    7,430
    Square Feet
    18.11
    Acres
    $350,000 | 109 Central Street, Brattleboro, VT 05301
    1/2

    $350,000

    4
    Bedrooms
    1,808
    Square Feet
    0.12
    Acres
    $350,000 | 109 Central Street, Brattleboro, VT 05301
    1/2

    $350,000

    4
    Bedrooms
    1,808
    Square Feet
    0.12
    Acres

    Nearby home values

    AddressSold priceBedsBathsSqftLot (Sqft)
    This home: 357 Hillwinds Road, Brattleboro, VT 05301
    $270,000
    3
    2,180
    65,340
    3
    3
    1,292
    45,302
    3
    2
    2,650
    60,984
    $56,652
    2
    2
    1,138
    47,916
    $450,000
    5
    2
    3,158
    60,984
    $705,000
    4
    3,257
    51,400

    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 09/06/2026 01:27 PM