SOLD OCT 19, 2026

Listed by Daire Gibney • Barrett and Valley Associates Inc. Bought with Town and Country Realty.

Off market oct 2026 for $560K

$537,837

Est. refi paymentEst. refi $3,672/mo

•

8.5 ba

•

6,078

sq ft

225 Pleasant St, Chester, VT 05143

About this home

Don't miss this comfortable Victorian home, having been a successful Inn for many years, will also be a wonderful location for the life style of your family, be it a business or a residence. With 9 bedrooms and 8 bathrooms plus parking for 8-10 vehicles there is ample space to run an Airbnb or host a large family retreat. With several ski resorts all under 30 minutes away this is an ideal property for a ski/recreational club house. There is plenty of room to entertain with a large dining room, living rooms and the old tavern with a large deck for lounging, after a day of exploring the area. The property has been lovingly maintained and it shows. Just moments from the quaint Village of Chester and quick access to I-91, it is conveniently situated to access all the wonders Vermont has to offer. This is without doubt a special place with the value you are seeking! Come, look, see for yourself!

Single-familyProperty Type

1861Year Built

1.3 acresLot Size

$88Est. Price/Sq.Ft.

2 car garageParking

Listed by Daire Gibney • Barrett and Valley Associates Inc.

Bought with Don Chabot • Town and Country Realty

Source:PrimeMLS #4826630

Redfin Estimate

$537,837

$22K since sold in October 2026$21K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 25.8% higher than the average sale price ($428K) of 6 comparable homes.

SOLD AUG 6, 2026
$275,000
A
4 beds3 baths3,332 sq ft
397 River St, Chester, VT 05143
SOLD APR 2, 2026
$550,000
B
— beds— baths3,850 sq ft
534 Elm St, Chester, VT 05143
SOLD OCT 9, 2026
$335,000
C
4 beds3 baths2,012 sq ft
196 Union St, Springfield, VT 05156
SOLD APR 13, 2026
$563,000
D
4 beds3 baths2,794 sq ft
95 Church St, Chester, VT 05143
SOLD JUN 2, 2026
$515,000
E
5 beds5 baths3,880 sq ft
514 First Ave, Chester, VT 05143
SOLD MAR 27, 2026
$327,000
F
5 beds3 baths2,963 sq ft
513 Giddings St, North Springfield, VT 05150

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Earn from this home

Refinance

Est. cash available

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Rent

$4,038/mo

Redfin rental estimate

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Market trends in 05143, VT

Last updated October 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-list price

96.0%

0.9% MoM

Median sale price

$374K

$110 MoM

Avg. days on market

66d

8 days MoM

Recently sold homes

4 MoM

New listings for sale

$279,000
3 beds1 bath992 sq ft
212 Cambridgeport Rd, Chester, VT 05143
$269,000
4 beds1 bath1,324 sq ft
426 Vermont Route 103, Chester, VT 05143
$549,000
4 beds2 baths2,190 sq ft
204 Fletcher Rd, Chester, VT 05143
$129,900
2 beds1 bath756 sq ft
473 Elm St, Chester, VT 05143
See all

Provided by Redfin

Sale history for 225 Pleasant St

Date

Event

Price

Public Records

Oct 19, 2026

Sold

$560,000

$92/sq ft

PrimeMLS #4826630

Sep 8, 2021

Sold

$375,000

$62/sq ft

Aug 27, 2021

Pending

—

Aug 26, 2021

Delisted

—

Aug 25, 2021

Pending

—

Aug 25, 2021

Delisted

—

Jul 5, 2021

Contingent

—

Jun 20, 2021

Relisted

—

Apr 2, 2021

Contingent

—

Oct 20, 2020

Price Changed

$374,000

$62/sq ft

Sep 3, 2020

Listed

$399,000

$66/sq ft

+35

PrimeMLS #4408789

May 21, 2015

Sold

$71,600

$12/sq ft

May 4, 2015

Delisted

—

Apr 23, 2015

Contingent

—

Mar 31, 2015

Price Changed

$74,900

$12/sq ft

Mar 24, 2015

Listed

$114,900

$19/sq ft

Come one come all! Ski clubs, large families and groups of friends. We have just the spot for you. Situated in the sweet village of Chester just a short ride to Okemo, Stratton, Magic and Bromley is this 9 bedroom 9 bath home. There is lots of common space, storage and yard. You can walk to area restaurants and stores. Previously used as a B & B. Don't hesitate this opportunity won't last long! Propery is sold "AS IS" with right to inspect by Limiited Warranty Deed. No property disclosure as owner has never occupied this home.

PrimeMLS #3021797

Mar 31, 2006

Sold

$510,000

$84/sq ft

Aug 8, 2005

Listed

$535,000

$88/sq ft

Public Records

Apr 7, 1999

Sold

$200,000

$33/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$6,102 (+4.8%)

$39,500 + $287,400

$326,900

2024

$5,823 (+12.2%)

$39,500 + $287,400

$326,900

2023

$5,190 (−33.4%)

$39,500 + $287,400

$326,900

2022

$7,795 (−2.8%)

$39,500 + $287,400

$326,900

2021

$8,022 (+4.0%)

$39,500 + $287,400

$326,900

2020

$7,710 (+7.6%)

$39,500 + $287,400

$326,900

2019

$7,164 (+2.0%)

$49,500 + $291,800

$341,300

2018

$7,024 (+2.0%)

$49,500 + $291,800

$341,300

2016

$6,888 (−32.2%)

$49,500 + $291,800

$341,300

2014

$10,156

Tax history for 225 Pleasant St

Year

Property tax

Land + Additions

Assessment*

2025

$6,102 (+4.8%)

$39,500 + $287,400

$326,900

2024

$5,823 (+12.2%)

$39,500 + $287,400

$326,900

2023

$5,190 (−33.4%)

$39,500 + $287,400

$326,900

2022

$7,795 (−2.8%)

$39,500 + $287,400

$326,900

2021

$8,022 (+4.0%)

$39,500 + $287,400

$326,900

2020

$7,710 (+7.6%)

$39,500 + $287,400

$326,900

2019

$7,164 (+2.0%)

$49,500 + $291,800

$341,300

2018

$7,024 (+2.0%)

$49,500 + $291,800

$341,300

2016

$6,888 (−32.2%)

$49,500 + $291,800

$341,300

2014

$10,156

*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: 2,010
Basement Finish: Finished
Basement Type: Partial

Bathroom Information
# of Full Baths: 8
# of 1/2 Baths: 1

Heating & Cooling
Heating Type: Forced Air

Room Information
# of Rooms: 24

Exterior

Exterior Information
Physical Condition: Average
Exterior Wall: Wood Siding/Shingle
Building Type: Single Family

Property Information
Living Sq. Ft: 6,078
Building Sq. Ft: 7,798
# of Stories: 2
Stories Type: 2
Legal Description: QUAIL HOLLOW

Lot Information
# of Buildings: 1
Land Sq. Ft: 56,628
Municipality Name: CHESTER
Acres: 1.3
County Use Description: RESIDENTIAL < 6 ACRES

Financial

Assessor Information
Assessment Year: 2025

Public facts

Beds: 9
Baths: 8.5
Sq. Ft.: 6,078
Stories: 2.0
Lot Size: 1.3 acres
Style: Single Family Residential
Year Built: 1861
Year Renovated: —
County: Windsor County
APN: 14404510354

Home facts updated by county records on Oct 29, 2026

Around this home

Schools

Some nearby schools may not be within this home's attendance zone. Please check the Green Mountain Unified School District website to verify.

Chester-Andover Unified School District #29

Public PreK-6 • 0.6mi

7/10

Green Mountain Uhsd #35

Public 7-12 • 0.5mi

4/10

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

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

2/10 Heat Factor

7 hot days expected this year, 17 days in 30 years

Wind Factor

We're working on getting current and accurate wind risk information for this home.

1/10 Air Factor

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

Provided by First Street

Historical weather

Chester, VT • 05143

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

$511,000 – $619,000

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

Nearby similar homes

$599,000

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New listings for sale in 05143

$279,000

3 beds1 bath992 sq ft

212 Cambridgeport Rd, Chester, VT 05143

Nine private acres • Modern kitchen • Inviting loft

$269,000

4 beds1 bath1,324 sq ft

426 Vermont Route 103, Chester, VT 05143

Hardwood floors • Level lot • Finished office

$549,000

4 beds2 baths2,190 sq ft

204 Fletcher Rd, Chester, VT 05143

2.03 acre lot • 2 garage spots • Built 1977

$129,900

2 beds1 bath756 sq ft

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Eat in kitchen • 1 car garage • Close to ski areas

Home values near 225 Pleasant St

Data from public records.

Address	Redfin Estimate
245 Pleasant Street, Chester, VT 4 Beds \| 2 Baths \| 1500 Sq. Ft.	$371,411
230 Pleasant Street, Chester, VT 3 Beds \| 1.5 Baths \| 1846 Sq. Ft.	$358,752

Address	Redfin Estimate
279 Pleasant Street, Chester, VT 4 Beds \| 2 Baths \| 3804 Sq. Ft.	$430,643
157 Pleasant Street, Chester, VT 7 Beds \| 4 Baths \| 2755 Sq. Ft.	—

Address	Redfin Estimate
183 Pleasant Street, Chester, VT 4 Beds \| 2.5 Baths \| 2686 Sq. Ft.	$407,320
193 Talc Mill Road, Chester, VT 2 Beds \| 1 Baths \| 792 Sq. Ft.	$125,327

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About this home

Redfin Estimate

Earn from this home

Market trends in 05143, VT

Sale history for 225 Pleasant St

Tax history for 225 Pleasant St

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 05143

Home values near 225 Pleasant St

More real estate resources