414 Hillwinds Road

Closed 12/9/05

Sold

Last Sold Price

$295,000

3 beds2 baths1,720 sqft$172/sqft

414 Hillwinds Rd, Brattleboro, VT 05301

Single FamilyProperty Type

1 acresLot Size

1974Year Built

$172/sq ftPrice per sq ft

1 carParking Spaces

Description

This handsome seven room cape is sited on a lovely lot at the end of Hillwinds and includes beautifully landscaped grounds that provide privacy and access to The Hillwinds Conservation Lands. Large sunny deck, hardwood flooring, fireplace in the living room and full walk-out basement all add to it`s appeal. A wonderful home in a superb Hillwinds location!This handsome seven room cape is sited on a lovely lot at the end of Hillwinds and includes beautifully landscaped grounds that provide privacy and access to The Hillwinds Conservation Lands. Large sunny deck, hardwood flooring, fireplace in the living room and full walk-out basement all add to it`s appeal. A wonderful home in a superb Hillwinds location!

Sold By Berkley & Veller Greenwood Country

Listed by: Robert Doyle • Berkley & Veller Greenwood Country

Listing closed: 12/09/2005 12:00 AM • Source: New England Real Estate Network, MLS#: 3023067

Recent comparable sales

Median sold price

$330,000

Avg days on market

Sale-to-list ratio

98.8%

1/31

$320,000

Sold 07/31/26

3
Bedrooms: 2
Bathrooms: 1,703
Square Feet: 0.56
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1089 Marlboro Road, Brattleboro, VT 05301

1/34

$310,000

Sold 07/03/25

3
Bedrooms: 2
Bathrooms: 1,666
Square Feet: 0.29
Acres

34 Hampshire Circle, Brattleboro, VT 05301

1/34

$350,000

Sold 04/01/25

3
Bedrooms: 2
Bathrooms: 1,754
Square Feet: 0.36
Acres

113 Stockwell Drive, Brattleboro, VT 05301

1/28

$342,500

Sold 12/20/24

3
Bedrooms: 2
Bathrooms: 1,683
Square Feet: 0.17
Acres

35 South Street, Brattleboro, VT 05301

1/25

$370,000

Sold 04/02/26

3
Bedrooms: 2
Bathrooms: 1,820
Square Feet: 0.36
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115 Country Hill, Brattleboro, VT 05301

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3
Bedrooms: 2
Bathrooms: 1,631
Square Feet: 0.18
Acres

70 Greenleaf Street, Brattleboro, VT 05301

1/26

$315,000

Sold 02/28/25

3
Bedrooms: 2
Bathrooms: 1,971
Square Feet: 0.36
Acres

334 Carriage Hill Road, Brattleboro, VT 05301

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$330,000

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3
Bedrooms: 2
Bathrooms: 1,521
Square Feet: 0.5
Acres

255 Guilford Street, Brattleboro, VT 05301

1/39

$315,000

Sold 01/03/25

3
Bedrooms: 2
Bathrooms: 2,061
Square Feet: 0.1
Acres

106 Western Avenue, Brattleboro, VT 05301

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Property Information for 414 Hillwinds Road

Property Details

Taxes: $4,604 / year
MLS Type: Residential / Single Family
County: Windham County
Development / Subdivision: None (Bratt)

Building Information

Stories: 2
Year Built: 1974
Lot Size: 1.00 AC / 43,560 SF

Summary

Location and General Information

City: Brattleboro
County: VT-Windham

Directions: At the very end of Hillwinds Road.
Road Frontage: Yes
State: VT
Zip: 05301

Taxes and HOA Information

Tax - Gross Amount: $4,604.00
Tax Year: 2005

School Information

School - High: Brattleboro High School
School - Elementary: Brattleboro Elem Schools

Parking

Garage: Yes
Garage Capacity: 1.00

Driveway: Paved

Property

Lot Information

Common Land Acres: 0.0
Lot Size Acres: 1.0

Road Frontage Length: 0.0
Square Feet Apx Finished Above Grade: 1720.0
Square Feet Apx Finished Below Grade: 0.0
Square Feet Apx Total Finished: 1720.0

Property and Assessments

Property Class: Residential
Property Type: Single Family

Foundation: Concrete
Owned Land: Yes
Resort: No
ROW - Parcel Access: No
Year Built: 1974

Utilities

Electric: Circuit Breaker(s)
Sewer: Septic

Interior and Exterior Features

Exterior Features

Color: GREY
Features - Exterior: Deck

Roads: Cul-de-Sac
Roof: Shingle - Other

Interior Features

Appliances: Dishwasher, Disposal, Dryer, Microwave, Range - Electric, Refrigerator, Washer
Basement Access Type: Walkout

Basement Description: Full, Other
Baths - Total: 2
Baths - Full: 2
Half Baths: 0
Rooms - Total: 7
Bedrooms - Total: 3
Features - Interior: Fireplace - Wood, Fireplaces - 1, Kitchen Island
Flooring: Carpet, Hardwood, Vinyl
Heat Fuel: Oil
Heating: Hot Water, Multi Zone
Cooling: Multi Zone
Total Stories: 2

Room Information

Room 1

Room Dimensions: 18x11`6
Room Level: 1

Room Type: Kitchen

Room 2

Room Dimensions: 12`2x8`8
Room Level: 1

Room Type: Dining Room

Room 3

Room Dimensions: 18x12`6
Room Level: 1

Room Type: Living Room

Room 4

Room Dimensions: 13`6x12`6
Room Level: 1

Room Type: Family Room

Room 7

Room Dimensions: 13x18
Room Level: 2

Room Type: Master Bedroom

Room 8

Room Dimensions: 13x18
Room Level: 2

Room Type: Bedroom

Room 9

Room Dimensions: 12`6x10
Room Level: 1

Room Type: Bedroom

Room 16

Room Level: 1
Room Type: Bath - Full

Room 17

Room Level: 2
Room Type: Bath - Full

Rental

Rent Information

Rented: No

Property History for 414 Hillwinds Road

Date	Event & Source	Price	Appreciation
Dec 9, 2005	Sold New England Real Estate Network #3023067	$295,000	—
Oct 26, 2005	Pending New England Real Estate Network #3023067		—
Sep 29, 2005	Price Change New England Real Estate Network #3023067	$314,900	—
Sep 29, 2005	Listed (Active) New England Real Estate Network #3023067	$297,500	—
Nov 2, 2000	Sold New England Real Estate Network #3004322	$195,000	—
Oct 19, 2000	Pending New England Real Estate Network #3004322		—
Aug 30, 2000	Listed (Active) New England Real Estate Network #3004322	$197,500	—

Date	Event & Source	Price
12/09/2005	Sold New England Real Estate Network #3023067	$295,000
10/26/2005	Pending New England Real Estate Network #3023067	—
09/29/2005	Price Change New England Real Estate Network #3023067	$314,900
09/29/2005	Listed (Active) New England Real Estate Network #3023067	$297,500
11/02/2000	Sold New England Real Estate Network #3004322	$195,000
10/19/2000	Pending New England Real Estate Network #3004322	—
08/30/2000	Listed (Active) New England Real Estate Network #3004322	$197,500

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

Public Records for 414 Hillwinds Road

Taxable ValueLand$65,000Additions$164,250Total$229,250

Tax Record2025$4,354 ($363 / month)

Home Facts

Beds3Baths2Total Finished SqFt1,504 SqFtAbove Grade Finished SqFt1,504 SqFtStories2Lot Size43,560 SqFtStyleSingle Family ResidenceYear Built1974Year Renovated1974ZoningRRCountyWINDHAMAPN(025) 00070179.000

Schools near 414 Hillwinds Road

This home is within Windham Southeast Unified Union School District #96.


Rating	School	Type	Grades	Distance
6/10	Academy School	Public - Nearby school	PK to 6	2.3 mi
6/10	Brattleboro Area Middle School	Public - Serves this home	7 to 8	3.8 mi
7/10	Brattleboro Senior Uhsd #6	Public - Serves this home	9 to 12	3.8 mi
8/10	Green Street School	Public - Nearby school	PK to 6	2.8 mi
5/10	Canal Street/Oak Grove Schools	Public - Nearby school	PK to 6	3.6 mi
NR	Windham Regional Career Center	Public - Choice school	9 to 12	3.8 mi
NR	Neighborhood Schoolhouse	Private - Nearby school	PK to 8	2.4 mi


Rating	School	Distance
6/10	Academy School PublicPK to 6 Nearby school	2.3 mi
6/10	Brattleboro Area Middle School Public7 to 8 Serves this home	3.8 mi
7/10	Brattleboro Senior Uhsd #6 Public9 to 12 Serves this home	3.8 mi
8/10	Green Street School PublicPK to 6 Nearby school	2.8 mi
5/10	Canal Street/Oak Grove Schools PublicPK to 6 Nearby school	3.6 mi
NR	Windham Regional Career Center Public9 to 12 Choice school	3.8 mi
NR	Neighborhood Schoolhouse PrivatePK to 8 Nearby school	2.4 mi

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

Address	Sold price	Beds	Baths	Sqft	Lot (Sqft)
This home: 414 Hillwinds Road, Brattleboro, VT 05301	$295,000	3	2	1,720	43,560
410 Hillwinds Road, Brattleboro, VT 05301	$450,000	5	2	3,158	60,984
373 Hillwinds Road, Brattleboro, VT 05301	–	3	3	1,292	45,302
1030 Upper Dummerston Road, Brattleboro, VT 05301	–	3	2	1,920	278,784
357 Hillwinds Road, Brattleboro, VT 05301	$270,000	3	2	2,180	65,340
348 Hillwinds Road, Brattleboro, VT 05301	$56,652	2	2	1,138	47,916
1004 Upper Dummerston Road, Brattleboro, VT 05301	$50,000	1	3	2,948	235,224
345 Hillwinds Road, Brattleboro, VT 05301	–	3	2	2,650	60,984
964 Upper Dummerston Road, Brattleboro, VT 05301	–	2	3	1,710	141,570
336 Hillwinds Road, Brattleboro, VT 05301	$705,000	4	3	3,257	51,400
904 Upper Dummerston Road, Brattleboro, VT 05301	$355,000	3	3	2,935	355,014
902 Meadowbrook Road, Brattleboro, VT 05301	$85,000	–	–	–	470,448
1053 Upper Dummerston Road, Brattleboro, VT 05301	–	3	2	1,851	82,764
321 Hillwinds Road, Brattleboro, VT 05301	–	4	2.5	2,464	108,900
7 Capy Way, Unit 15, Brattleboro, VT 05301	–	–	1	951	108,900
306 Hillwinds Road, Brattleboro, VT 05301	–	4	3.5	2,590	58,370

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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 05:25 PM

Brattleboro, VT

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