Google street view image for 20 Winding Hill Rd

Listing provided courtesy of Bellville Realty. Bought with zHelp-U-Sell Region of NH, ME, VT.

Off Market Jun 2000 for $24K

$82,605

•

—

sq ft

20 Winding Hill Rd, Brattleboro, VT

About this home

Single-familyProperty Type

1983Year Built

Listed by • Bellville Realty

Bought with • zHelp-U-Sell Region of NH, ME, VT

Redfin checked: 2 minutes ago

•Source:PrimeMLS #3079468

Redfin Estimate

$82,605

$58K since sold in June 2000$9,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 65.6% lower than the average sale price ($240K) of 5 comparable homes.

SOLD AUG 20, 2026
$325,000
A
3 beds2 baths1,272 sq ft
184 Carriage Hill Rd, Brattleboro, VT 05301
SOLD MAR 31, 2026
$93,000
B
2 beds2 baths1,008 sq ft
26 Lynwood Dr, Brattleboro, VT 05301
SOLD JAN 23, 2026
$89,900
C
2 beds2 baths910 sq ft
2 Wagon Dr, Brattleboro, VT 05301
SOLD AUG 17, 2026
$305,000
D
3 beds1.5 baths1,056 sq ft
15 Lawton Dr, Brattleboro, VT 05301
SOLD JUL 24, 2026
$389,000
E
3 beds2 baths1,377 sq ft
366 Hague Rd, Dummerston, VT 05301

Claim this home to receive a free report every month with insights on the changing estimate.

Market trends in 05301, VT

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

99.7%

+0.5% MoM

Median sale price

$387K

$2K MoM

Avg. days on market

59d

9 days MoM

Recently sold homes

8 MoM

New listings for sale

$830,000
5 beds5.5 baths5,064 sq ft
253 Sugar House Hl, Guilford, VT 05301
$149,900
3 beds2 baths1,232 sq ft
14 Deepwood Park, Brattleboro, VT 05301
$395,000
2 beds2 baths1,400 sq ft
215 Gilbert Rd, Marlboro, VT 05344
$190,000
2 beds1 bath930 sq ft
39 Brookside Dr #5, Brattleboro, VT 05301
$120,000
2 beds1 bath924 sq ft
21 Winding Hl, Brattleboro, VT 05301
$499,000
2 beds2 baths1,775 sq ft
171 Buttonwood Dr, Brattleboro, VT 05301
$525,000
3 beds2.5 baths2,330 sq ft
205 Wantastiquet Dr, Brattleboro, VT 05301
$479,000
2 beds2 baths1,775 sq ft
162 Buttonwood Dr, Brattleboro, VT 05301
$439,000
2 beds2 baths1,550 sq ft
77 Buttonwood Dr, Brattleboro, VT 05301
$289,000
2 beds1 bath925 sq ft
45 Kopkind Rd, Guilford, VT 05301

Provided by Redfin

Sale history for 20 Winding Hill Rd

Tax history for 20 Winding Hill Rd

*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

Baths

Stories

Lot width

—

Lot depth

—

Lot size

104.07 Acres

Year renovated

—

Sq. Ft.

1,018

Year built

1983

Style

Mobile/Manufactured Home

County

Windham County

APN

08102514968

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 8, 2026.

Residential Neighborhood District

The Residential Neighborhood District is composed of high- to moderate-density residential neighborhoods extending outward from downtown Brattleboro and West Brattleboro village, and along the Route 9 corridor. While primarily residential in use, these neighborhoods vary significantly in the form and density of housing they offer, and include traditional neighborhoods, post-war suburban-style neighborhoods, multi-family developments, townhouses and mobile home parks. The land within this district is generally served by municipal water and sewer. Walkability and proximity to public transit service, neighborhood stores, schools, parks and other amenities varies by neighborhood. The purpose of this district is to allow a diverse range of housing, encourage an increase in and improvement of the town’s housing stock, and promote more compact, walkable neighborhoods in balance with protection of neighborhood character and quality of life, and in accordance with the policies of the Brattleboro Town Plan.

Property details

Parking

Parking & Garage
None

Interior

Bathroom Information
# of Baths (full): 2

Basement Information
None, Other

Other Interior Features
# of Rooms: 6
Water Heater: Electric
Other

Equipment & Appliance Information
Dishwasher, Dryer, Exhaust Hood, Other, Refrigerator, Washer

Room 1 Information
Kitchen
Kitchen
Dimensions: 14X11

Room 2 Information
Dining Room
Dimensions: 09X08

Room 3 Information
Living Room
Dimensions: 19X14

Room 7 Information
Master Bedroom
Dimensions: 12X14

Room 8 Information
Bedroom
Dimensions: 11X11

Room 9 Information
Bedroom
Dimensions: 08X10

Room 16 Information
Full Bath
Level: 1

Room 17 Information
Full Bath
Level: 1

Exterior

Building Information
Approximate Sq. Ft. Total Finished: 0
Patio
Foundation: Slab w/ Frost Wall
Roof: Metal
Exterior: Vinyl

Driveway
Other

Other Property & Lot Information
Year Built: 1983

Financial

Tax Information
Gross Amount Tax: 887.7

Financing Information
Conventional

Utilities

Heating & Cooling Information
Cooling: Other
Heat: Other

Sewer Information
Public

Water Information
Public

Location

Other Location Information
Directions: TAKE 2ND ENT. TO MT. HOMES FOLLOW WINDING HILL R D. ABOUT 3/10 MILE, BLUE TRAILER ON THE LEFT 20, ACROSS FROM A WHITE DOUBLE WIDE.

Public facts

Beds: 2
Baths: 2.0
Sq. Ft.: 1,018
Stories: 1.0
Lot Size: 104.07 acres
Style: Mobile/Manufactured Home
Year Built: 1983
Year Renovated: —
County: Windham County
APN: 08102514968

Home facts updated by county records on Jul 8, 2026

Other

Documents & Disclosures
Documents Available: None

Around this home

Schools

Some nearby schools may not be within this home's attendance zone. Please check the Windham Southeast Unified Union School District #96 website to verify.

Academy School

Public PreK-6 • 1.7mi

6/10

Neighborhood Schoolhouse

Private PreK-8 • 2.5mi

Hilltop Montessori School

Private PreK-8 • 2.8mi

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

3/10 Heat Factor

7 days above 93° expected this year, 16 days in 30 years

4/10 Wind Factor

10% chance of strong winds in next 30 years

2/10 Air Factor

0 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Brattleboro, VT • undefined

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

Is this your home?

Track this home’s value and nearby sales activity

Nearby similar homes

$1,650,000

4 beds3.5 baths3,268 sq ft

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6 beds2.5 baths3,682 sq ft

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Studio— baths1,200 sq ft

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New listings for sale in 05301

$830,000

5 beds5.5 baths5,064 sq ft

253 Sugar House Hl, Guilford, VT 05301

$149,900

3 beds2 baths1,232 sq ft

14 Deepwood Park, Brattleboro, VT 05301

$395,000

2 beds2 baths1,400 sq ft

215 Gilbert Rd, Marlboro, VT 05344

$190,000

2 beds1 bath930 sq ft

39 Brookside Dr #5, Brattleboro, VT 05301

$120,000

2 beds1 bath924 sq ft

21 Winding Hl, Brattleboro, VT 05301

$499,000

2 beds2 baths1,775 sq ft

171 Buttonwood Dr, Brattleboro, VT 05301

$525,000

3 beds2.5 baths2,330 sq ft

205 Wantastiquet Dr, Brattleboro, VT 05301

$479,000

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162 Buttonwood Dr, Brattleboro, VT 05301

$439,000

2 beds2 baths1,550 sq ft

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Home values near 20 Winding Hill Rd

Data from public records.

Address	Redfin Estimate
5 Hillwinds N, Brattleboro, VT 2 Beds \| 1 Baths \| 1032 Sq. Ft.	—
9 Hillwinds Rd, Brattleboro, VT 3 Beds \| 1 Baths \| 924 Sq. Ft.	—

Address	Redfin Estimate
3 Hillwinds Rd, Brattleboro, VT 2 Beds \| 1 Baths \| 792 Sq. Ft.	—
15 Hillwinds Rd, Brattleboro, VT 2 Beds \| 1.5 Baths \| 953 Sq. Ft.	$143,703

Address	Redfin Estimate
18 Hillwinds Rd, Brattleboro, VT 2 Beds \| 1.5 Baths \| 952 Sq. Ft.	$89,747
22 Hillwinds Rd, Brattleboro, VT 2 Beds \| 1 Baths \| 852 Sq. Ft.	$76,653

Property information provided by PrimeMLS when last listed in 1999. This data may not match . Learn more.

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