Sold
Last Sold Price
4 beds2,632 sqft
208 Hillwinds Rd, Brattleboro, VT 05301
Single FamilyProperty Type
1.28 acresLot Size
1988Year Built
$122/sq ftPrice per sq ft
$8/moHOA Fees
2 carsParking Spaces

Description

This 4 bedroom spacious colonial is located in one of Brattleboro`s finest neighborhoods. Lovely views, end of road location and access to Hillwinds conserved land. There is a large wraparound porch and private rear deck.This 4 bedroom spacious colonial is located in one of Brattleboro`s finest neighborhoods. Lovely views, end of road location and access to Hillwinds conserved land. There is a large wraparound porch and private rear deck.

    Sold By Berkley & Veller Greenwood Country

    • Listed by: Janet Walkiewicz • Berkley & Veller Greenwood Country
    Listing closed: 06/01/2007 12:00 AM • Source: New England Real Estate Network, MLS#: 3036944

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    Recent comparable sales

    Median sold price

    $408,065

    Avg days on market

    77

    Sale-to-list ratio

    93.8%

    Brattleboro, VT

    9 comparable properties found

    $405,000 | 156 Sherwood Circle, Brattleboro, VT 05301
    1/45
    1

    $405,000

    Sold 07/28/25

    4
    Bedrooms
    2,132
    Square Feet
    0.86
    Acres
    $339,000 | 65 Cedar Street, Brattleboro, VT 05301
    1/41
    2

    $339,000

    Sold 08/14/26

    4
    Bedrooms
    2,250
    Square Feet
    0.2
    Acres
    $365,000 | 85 Stockwell Drive, Brattleboro, VT 05301
    1/26
    3

    $365,000

    Sold 05/26/26

    5
    Bedrooms
    2,254
    Square Feet
    0.4
    Acres
    $450,000 | 214 Putney Road, Brattleboro, VT 05301
    1/47
    4

    $450,000

    Sold 05/15/26

    4
    Bedrooms
    2,756
    Square Feet
    0.79
    Acres
    $495,000 | 41 Chapin Street, Brattleboro, VT 05301
    1/52
    5

    $495,000

    Sold 07/30/26

    4
    Bedrooms
    2,874
    Square Feet
    0.19
    Acres
    $580,000 | 11 Strawberry Hill, Brattleboro, VT 05301
    1/38
    6

    $580,000

    Sold 06/30/26

    4
    Bedrooms
    2,573
    Square Feet
    1.9
    Acres
    $497,408 | 204 Meeting House Lane, Brattleboro, VT 05301
    1/31
    7

    $497,408

    Sold 04/10/26

    4
    Bedrooms
    2,656
    Square Feet
    1.28
    Acres
    $408,065 | 76 Spruce Street, Brattleboro, VT 05301
    1/45
    8

    $408,065

    Sold 03/12/26

    4
    Bedrooms
    3,314
    Square Feet
    0.36
    Acres
    $385,000 | 135 Country Hill, Brattleboro, VT 05301
    1/27
    9

    $385,000

    Sold 06/01/26

    3
    Bedrooms
    2,128
    Square Feet
    0.33
    Acres

    Location

    Add your commute

    Payment Calculator

    $2,338 per month

    30 year fixed, 7.03% Interest

    Principal and Interest

    $1,719

    Property Taxes

    $611

    HOA Dues

    $8

    The Payment Calculator is for illustrative purposes only.

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    Property Information for 208 Hillwinds Road

    Property Details
    • Taxes: $7,330 / year
    • MLS Type: Residential / Single Family
    • Development / Subdivision: None (Bratt)
    Building Information
    • Stories: 2
    • Year Built: 1988
    • Lot Size: 1.28 AC / 55,756 SF
    Summary
    Location and General Information
    • City: Brattleboro
    • County: VT-Windham
    • Directions: Route 30 to Upper Dummerston Road to Hillwinds on left. Up hill 1st right onto Hillwinds North. Last house on left. See sign.
    • Road Frontage: Yes
    • State: VT
    • Zip: 05301
    Taxes and HOA Information
    • Fee: $8.00
    • Fee Frequency: Monthly
    • Tax - Gross Amount: $7,330.00
    • Tax Year: 2006
    School Information
    • School - High: Brattleboro High School
    • School - Elementary: Brattleboro Elem Schools
    Parking
    • Garage: Yes
    • Garage Capacity: 2.00
    • Driveway: Paved
    Property
    Lot Information
    • Common Land Acres: 0.0
    • Lot Size Acres: 1.28
    • Road Frontage Length: 232.0
    • Square Feet Apx Finished Above Grade: 2632.0
    • Square Feet Apx Finished Below Grade: 0.0
    • Square Feet Apx Total Finished: 2632.0
    Property and Assessments
    • Property Class: Residential
    • Property Type: Single Family
    • Foundation: Concrete
    • Owned Land: Yes
    • Resort: No
    • ROW - Length: 0
    • ROW - Parcel Access: No
    • Year Built: 1988
    Utilities
    • Electric Company: CVPS
    • Cable Company: Comcast
    • Fuel Company: Suburban
    • Electric: Circuit Breaker(s)
    • Sewer: Leach Field, Septic
    • Utilities: Cable
    Interior and Exterior Features
    Exterior Features
    • Color: Grey
    • Features - Exterior: Deck, Porch - Covered, Window Screens
    • Roof: Shingle - Other
    Interior Features
    • Appliances: Dishwasher, Dryer, Exhaust Hood, Range - Gas, Refrigerator, Washer
    • Basement Description: Bulkhead, Full, Other, Stairs - Interior, Unfinished
    • Baths - Total: 3
    • Baths - Full: 2
    • Half Baths: 1
    • Rooms - Total: 9
    • Bedrooms - Total: 4
    • Features - Interior: Fireplace - Wood, Fireplaces - 1, Kitchen/Family, Master BR w/ BA, Laundry - 1st Floor
    • Flooring: Ceramic Tile, Hardwood, Vinyl
    • Heat Fuel: Gas - LP/Bottle, Wood
    • Heating: Hot Water, Multi Zone
    • Cooling: Multi Zone
    • Total Stories: 2
    Room Information
    Room 1
    • Room Dimensions: 25x14
    • Room Level: 1
    • Room Type: Kitchen
    Room 2
    • Room Dimensions: 14x14
    • Room Level: 1
    • Room Type: Dining Room
    Room 3
    • Room Dimensions: 22x14
    • Room Level: 1
    • Room Type: Living Room
    Room 4
    • Room Dimensions: 16x15
    • Room Level: 1
    • Room Type: Family Room
    Room 5
    • Room Type: Foyer
    Room 7
    • Room Dimensions: 16x15
    • Room Level: 2
    • Room Type: Master Bedroom
    Room 8
    • Room Dimensions: 14x13
    • Room Level: 2
    • Room Type: Bedroom
    Room 9
    • Room Dimensions: 15x13
    • Room Level: 2
    • Room Type: Bedroom
    Room 10
    • Room Dimensions: 14x13
    • Room Level: 2
    • Room Type: Bedroom
    Room 13
    • Room Dimensions: 16x15
    • Room Level: 1
    • Room Type: Other
    Room 16
    • Room Level: 2
    • Room Type: Bath - Full
    Room 17
    • Room Level: 2
    • Room Type: Bath - Full
    Room 18
    • Room Level: 1
    • Room Type: Bath - 1/2
    Rental
    Rent Information
    • Rented: No

    Property History for 208 Hillwinds Road

    DateEvent & SourcePriceAppreciation
    Jun 1, 2007

    Sold

    New England Real Estate Network #3036944

    $322,000—
    Feb 26, 2007

    Pending

    New England Real Estate Network #3036944

    —
    Feb 16, 2007

    Listed (Active)

    New England Real Estate Network #3036944

    $329,000—
    DateEvent & SourcePrice
    06/01/2007

    Sold

    New England Real Estate Network #3036944

    $322,000
    02/26/2007

    Pending

    New England Real Estate Network #3036944

    —
    02/16/2007

    Listed (Active)

    New England Real Estate Network #3036944

    $329,000

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

    Schools near 208 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.

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    Nearby home values

    AddressSold priceBedsBathsSqftLot (Sqft)
    This home: 208 Hillwinds Road, Brattleboro, VT 05301
    $322,000
    4
    2,632
    55,756
    –
    4
    2.5
    2,400
    91,476
    $370,000
    3
    1,404
    47,654
    –
    4
    1.5
    1,440
    71,438
    $192,500
    3
    1,300
    65,340
    $370,000
    3
    3,010
    50,965

    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 09/28/2026 04:18 AM