Google street view image for 199 Gypsy Ln, Bennington, VT 05201

Off Market Sep 2008 for $260K

$414,652

Est. refi paymentEst. refi $1,709/mo

•

2.5 ba

•

2,061

sq ft

199 Gypsy Ln, Bennington, VT 05201

About this home

199 Gypsy Ln is a 2,061 square foot house on a 8.13 acre lot with 4 bedrooms and 2.5 bathrooms. - it last sold on September 12, 2008 for $260,000. Based on Redfin's Bennington data, we estimate the home's value is $414,652.

Single-familyProperty Type

1953Year Built

8.13 acresLot Size

$201Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$414,652

$155K since sold in September 2008$2,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 8.9% higher than the average sale price ($381K) of 6 comparable homes.

SOLD JUN 26, 2026
$350,000
A
4 beds2 baths2,108 sq ft
149 Jewett Dr, Bennington, VT 05201
SOLD JUL 22, 2026
$295,000
B
3 beds2 baths2,753 sq ft
166 Cardinal Ln, Bennington, VT 05201
SOLD NOV 21, 2025
$351,000
C
4 beds3 baths2,994 sq ft
165 Pippin Knl, Bennington, VT 05201
SOLD DEC 19, 2025
$480,000
D
4 beds2.5 baths2,116 sq ft
245 Southshire Dr, Bennington, VT 05201
SOLD JUL 31, 2026
$399,900
E
4 beds2 baths1,896 sq ft
23 Pageant St, Bennington, VT 05201
SOLD JUL 27, 2026
$408,000
F
4 beds3 baths2,119 sq ft
131 Pine Cir, Bennington, VT 05201

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Earn from this home

Refinance

Est. cash available

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Rent

$1,685/mo

Redfin rental estimate

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Market trends in 05201, VT

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

99.2%

1.4% MoM

Median sale price

$295K

$2K MoM

Avg. days on market

60d

1 days MoM

Recently sold homes

1 MoM

New listings for sale

NEW 22 HRS AGO
$315,000
3 beds1.5 baths1,365 sq ft
314 Chester Knoll Dr, Bennington, VT 05201
$579,000
3 beds2 baths2,501 sq ft
856 Matteson Rd, North Bennington, VT 05201
FOR SALE BY OWNER
$160,000
8 beds2 baths2,334 sq ft
1032 Main St, Bennington, VT 05201
$175,000
2 beds1 bath810 sq ft
220 Gage St, Bennington, VT 05201
See all

Provided by Redfin

Sale history for 199 Gypsy Ln

Year

Property tax

Land + Additions

Assessment*

2025

$3,101 (−0.9%)

$53,800 + $152,000

$205,800

2024

$3,129 (+5.4%)

$53,800 + $152,000

$205,800

2023

$2,970 (−37.0%)

$53,800 + $152,000

$205,800

2022

$4,716 (−0.5%)

$53,800 + $152,000

$205,800

2021

$4,740 (+0.2%)

$53,800 + $152,000

$205,800

2020

$4,728 (+5.2%)

$53,800 + $152,000

$205,800

2019

$4,496 (+1.7%)

$53,800 + $152,000

$205,800

2018

$4,421 (−1.0%)

$53,800 + $152,000

$205,800

2017

$4,467 (+1.6%)

$53,800 + $152,000

$205,800

2016

$4,398 (+0.9%)

$53,800 + $152,000

$205,800

2015

$4,358 (−15.8%)

$53,800 + $152,000

$205,800

2014

$5,174

$53,800 + $152,000

$205,800

2013

$53,800 + $152,000

$205,800

Tax history for 199 Gypsy Ln

Year

Property tax

Land + Additions

Assessment*

2025

$3,101 (−0.9%)

$53,800 + $152,000

$205,800

2024

$3,129 (+5.4%)

$53,800 + $152,000

$205,800

2023

$2,970 (−37.0%)

$53,800 + $152,000

$205,800

2022

$4,716 (−0.5%)

$53,800 + $152,000

$205,800

2021

$4,740 (+0.2%)

$53,800 + $152,000

$205,800

2020

$4,728 (+5.2%)

$53,800 + $152,000

$205,800

2019

$4,496 (+1.7%)

$53,800 + $152,000

$205,800

2018

$4,421 (−1.0%)

$53,800 + $152,000

$205,800

2017

$4,467 (+1.6%)

$53,800 + $152,000

$205,800

2016

$4,398 (+0.9%)

$53,800 + $152,000

$205,800

2015

$4,358 (−15.8%)

$53,800 + $152,000

$205,800

2014

$5,174

$53,800 + $152,000

$205,800

2013

$53,800 + $152,000

$205,800

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Property details

Interior

Basement Information
Basement Sq. Ft: 1,372
Basement Type: Full

Bathroom Information
# of Full Baths: 2
# of 1/2 Baths: 1

Heating & Cooling
Heating Type: Forced Hot Water

Room Information
# of Rooms: 7

Exterior

Exterior Information
Physical Condition: Average
Building Style Type: Cape Cod
Exterior Wall: Vinyl
Building Type: Single Family

Property Information
Living Sq. Ft: 2,061
Building Sq. Ft: 3,433
Legal Description: HSE OBS & 8.13A

Lot Information
# of Buildings: 1
Land Sq. Ft: 354,143
Municipality Name: BENNINGTON
Acres: 8.13
County Use Description: RESIDENTIAL-2

Financial

Assessor Information
Assessment Year: 2025

Public facts

Beds: 4
Baths: 2.5
Sq. Ft.: 2,061
Stories: —
Lot Size: 8.13 acres
Style: Single Family Residential
Year Built: 1953
Year Renovated: —
County: Bennington County
APN: 05101564130

Home facts updated by county records on Jul 15, 2026

Around this home

Schools

Mt. Anthony Union Middle School

Public 6-8 • Assigned • 2.5mi

3/10

Mt. Anthony Senior Uhsd #14

Public 9-12 • Assigned • 1.9mi

5/10

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

3/10 Fire Factor

0.15% chance of being in a wildfire in next 30 years

2/10 Heat Factor

7 days above 90° expected this year, 16 days in 30 years

3/10 Wind Factor

6% 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

Bennington, VT • 05201

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.6 hours in June and 3.6 hours in December, placing it below the U.S. average for solar exposure.

8.6 hrs

3.6 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$394,000 – $477,000

Sell confidently with a local market expert in Bennington. 3 minutes to get started.

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New listings for sale in 05201

NEW 22 HRS AGO

$315,000

3 beds1.5 baths1,365 sq ft

314 Chester Knoll Dr, Bennington, VT 05201

$579,000

3 beds2 baths2,501 sq ft

856 Matteson Rd, North Bennington, VT 05201

FOR SALE BY OWNER

$160,000

8 beds2 baths2,334 sq ft

1032 Main St, Bennington, VT 05201

$175,000

2 beds1 bath810 sq ft

220 Gage St, Bennington, VT 05201

Home values near 199 Gypsy Ln

Data from public records.

Address	Redfin Estimate
157 Gypsy Ln, Bennington, VT 4 Beds \| 1 Baths \| 1361 Sq. Ft.	$305,064
85 Gypsy Ln, Bennington, VT 3 Beds \| 2 Baths \| 1190 Sq. Ft.	$282,340

Address	Redfin Estimate
112 Gypsy Ln, Bennington, VT 4 Beds \| 2.5 Baths \| 2662 Sq. Ft.	$467,177
25 Gypsy Ln, Bennington, VT 3 Beds \| 2 Baths \| 1382 Sq. Ft.	$279,226

Address	Redfin Estimate
125 Gypsy Ln, Bennington, VT 2 Beds \| 1.5 Baths \| 1698 Sq. Ft.	$228,052
152 Gypsy Ln, Bennington, VT 3 Beds \| 2.5 Baths \| 2664 Sq. Ft.	$529,321

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 05201, VT

Sale history for 199 Gypsy Ln

Tax history for 199 Gypsy Ln

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 05201

Home values near 199 Gypsy Ln

More real estate resources