For sale

$549,000

Est. $4,014/mo —

•

2,824

sq ft

147 Main St, Chester, NY 10918

About this home

Bring your vision to **147 Main Street in the Village of Chester**. Zoned **Duplex with Neighborhood Business use**, this spacious property offers an excellent opportunity for investors, business owners or buyers looking to renovate and create value. The property features multiple living areas, four bedrooms, a large kitchen with center island, one full bathroom, a half bathroom, laundry and storage space. An additional apartment includes its own entrance, kitchen, living area, bedroom and full bathroom. Multiple entrances provide flexibility throughout the property. Outside, enjoy several patio areas, a spacious fenced yard, mature trees and off-street parking. Conveniently located in the heart of the Village of Chester, near local shopping, dining, services and major roadways. The property requires repairs and updating and is being offered as an investment and renovation opportunity. Buyers should independently verify all property information, square footage, zoning, permitted uses and certificate-of-occupancy requirements with the Village of Chester.

Multi-familyProperty Type

1800Year Built

8,640 sq ftLot Size

$194Price/Sq.Ft.

Listing by Samantha Ortiz • Howard Hanna Rand Realty

Contact: 845-634-4202

Listing updated: Sep 21, 2026 at 03:44pm

Redfin checked: 3 minutes ago

•Source:OneKey® MLS as Distributed by MLS Grid #1052484

Payment calculator

$4,014 per month

Principal and interest$2,959

Property taxes

$968

HOA dues

Home insurance

$87

Utilities

Add

5 minutes to get started. No credit impact.

Discover your buying power

Find out if this home is within budget

Down payment assistance

View down payment assistance programs for this home

See this home in person

We'll connect you with a local agent to show you this home, answer your questions, and assist you on your buying journey.

Next available tour time: Tomorrow

Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN THU, 4PM TO 6PM3D WALKTHROUGH
$412,000
3 beds1 bath1,288 sq ft
21 Midway Dr, Monroe, NY 10950
Listing by Howard Hanna Rand Realty
OPEN THU, 5:30PM TO 7PM
$525,000
3 beds2.5 baths2,441 sq ft
94 Booth Rd, Chester, NY 10918
Listing by Howard Hanna Rand Realty
OPEN SAT, 11AM TO 1PM
$350,000
4 beds1 bath1,155 sq ft
14 Mohin Park, New Hampton, NY 10958
Listing by Keller Williams Realty
OPEN SAT, 12PM TO 3PM
$987,000
5 beds4 baths5,593 sq ft
4 Fox Hollow Dr, Blooming Grove, NY 10914
Listing by Howard Hanna Rand Realty
OPEN SAT, 12PM TO 2:30PM
$525,000
2 beds2 baths1,910 sq ft
19 Meadow Ave, Chester, NY 10918
Listing by RE/MAX Town & Country
OPEN SAT, 12PM TO 2PM
$269,000
2 beds1 bath1,084 sq ft
1212 Whispering Hls, Chester, NY 10918
Listing by Keller Williams Realty
OPEN SAT, 12PM TO 2PM
$479,000
3 beds2 baths1,590 sq ft
30 Glenmere Ave, Florida, NY 10921
Listing by J C Realty International Inc.
OPEN SAT, 12PM TO 3PM
$584,000
2 beds2 baths1,520 sq ft
14 Pond Hill Ave, Warwick, NY 10990
Listing by BHG Real Estate Green Team
OPEN SAT, 1PM TO 3PM3D WALKTHROUGH
$449,555
3 beds1.5 baths1,751 sq ft
132 Ridge Rd, Highland Mills, NY 10930
Listing by Century 21 Full Service Realty
REDFIN OPEN SAT, 2PM TO 4PM3D WALKTHROUGH
$750,000
4 beds3 baths2,280 sq ft
1 Sanford Ave, Chester, NY 10918
Listing by Redfin Real Estate

Around this home

Schools

K - 12
Preschool & daycare

Chester Elementary School

Public PreK-5 • Assigned • 1.2mi

6/10

Chester Academy Middle High School

Public 6-12 • Assigned • 0.9mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Offer insights

147 Main St · $549,000

Strong offer

$572K and above

75% chance or better to win

Why $572K+ is a strong offer

DAYS ON MARKET

The average home goes pending in 50 days.

SALE-TO-LIST

Most homes are selling 6% below list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Breakfast bar
Open floor plan
Washer/dryer hookup
Laundry room
Basement is unfinished
Full, unfinished walkup attic

Bedrooms
One 4-bedroom unit (multi-unit property)

Bathrooms
Two full bathrooms

Kitchen
Breakfast bar (kitchen pass-through/open concept)

Laundry & utility
Washer/dryer hookup
Dedicated laundry room

Flooring
Carpet
Laminate
Wood

Heating & cooling
Hot water heating
Steam heating
Wall/window air conditioning units

Sale and tax history for 147 Main St

Sale History
Tax History

Year

Property tax

Land + Additions

Assessment*

2025

$11,312 (+2.1%)

$25,100 + $119,600

$144,700

2024

$11,075 (+4.8%)

$25,100 + $119,600

$144,700

2023

$10,567 (+5.4%)

$25,100 + $119,600

$144,700

2022

$10,025 (−0.2%)

$25,100 + $119,600

$144,700

2021

$10,048 (+4.7%)

$25,100 + $119,600

$144,700

2020

$9,600 (+88.6%)

$25,100 + $119,600

$144,700

2019

$5,091 (−7.3%)

$25,100 + $119,600

$144,700

2018

$5,494 (−18.0%)

$25,100 + $119,600

$144,700

2017

$6,700 (−28.3%)

$25,100 + $119,600

$144,700

2016

$9,341 (+44.4%)

$25,100 + $119,600

$144,700

2015

$6,469 (−0.3%)

$25,100 + $119,600

$144,700

2014

$6,488

$25,100 + $119,600

$144,700

Public record

Beds

Baths

2.5

Stories

Lot width

96 ft.

Lot depth

90 ft.

Lot size

8,640 Sq. Ft.

Year renovated

1916

Finished Sq. Ft.

2,824

Unfinished Sq. Ft.

—

Total Sq. Ft.

2,824

Year built

1800

Style

Multi-Family (2-4 Unit)

County

Orange County

APN

332201A11100000020322000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 13, 2026.

Climate risks

1/10 Flood Factor

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

3/10 Fire Factor

0.31% chance of being in a wildfire in next 30 years

4/10 Heat Factor

7 days above 97° expected this year, 15 days in 30 years

4/10 Wind Factor

15% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 2 days in 30 years

Provided by First Street

Historical weather

Chester, NY • 10918

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 8.7 hours in June and 3.9 hours in December, placing it below the U.S. average for solar exposure.

8.7 hrs

3.9 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 147 Main St

We cannot show automated home-value estimates for this home.

Nearby homes have recently sold between $560,000 and $785,000.

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $560K to $785K.

SOLD SEP 15, 2026
$700,000 Last sold price
3 beds2.5 baths2,600 sq ft
1 Hemlock Ct, Chester, NY 10918
Listing by MK Realty Inc
$75/sq ft
smaller lot
222 years newer
SOLD SEP 10, 2026
$740,000 Last sold price
5 beds2.5 baths2,700 sq ft
7 Hilltop Ln, Chester, NY 10918
Listing by MK Realty Inc
$80/sq ft
smaller lot
222 years newer
SOLD SEP 5, 2026
$710,000 Last sold price
5 beds2.5 baths3,200 sq ft
2 Gate Way, Port Chester, NY 10918
Listing by MK Realty Inc
$28/sq ft
smaller lot
222 years newer
SOLD SEP 8, 2026
$745,000 Last sold price
5 beds2.5 baths2,700 sq ft
1 Periwinkle Ct, Chester, NY 10918
Listing by MK Realty Inc
$82/sq ft
smaller lot
222 years newer
SOLD SEP 2, 2026
$560,000 Last sold price
4 beds2 baths2,076 sq ft
85 Surrey Rd, Chester, NY 10918
Listing by Keller Williams Realty
$76/sq ft
larger lot
168 years newer
SOLD JUL 17, 2026
$785,000 Last sold price
4 beds3.5 baths3,005 sq ft
17 Laurel Cir, Goshen, NY 10924
Listing by Howard Hanna Rand Realty
$67/sq ft
larger lot
219 years newer

Tour for free, no strings attached

Instant answers, or connect with a local agent

Start an offer