Google street view image for 27 Dug Rd, Chester, NY 10918

Off Market May 2012 for $285K

$653,483

Est. refi paymentEst. refi $539/mo

•

3.5 ba

•

2,728

sq ft

27 Dug Rd, Chester, NY 10918

About this home

ROCK BOTTOM PRICE! "Bow House" Cape-Cod sits picture perfect on 2-1/2 partially wooded ac! 1 of a kind! Perfect for the growing family or 1 desiring something refreshingly different! 2 story foyer! Solid wood doors! 2 fireplaces 1 in kit & 1 in formal LR w/ pine floors! Kit/great rm! Mstr BR on main lvl! Pine plank floors on main lvl under carpet. Corian counters! Abv grade lower lvl w/ spa rm w/ jacuzzi, shower + bidet & entertainment rm w/ blt-in b. cases leads to patio! Perfect M/D situation! Lush landscape with stack stone walls! & irrigation/sprink sys. 2 stream fed ponds! Central a/c & vac! Some "Calif. Closets"! 2 car gar & deck. Centrally located in Monroe-Woodbury Sch district!

Single-familyProperty Type

1977Year Built

2.5 acresLot Size

$240Est. Price/Sq.Ft.

2 spacesParking

Listing by • ARC Realty 1 in Sales

Bought with • Weichert Realtors

Redfin checked: over 7 days ago

•Source:HGMLS #516279

Redfin Estimate

$653,483

$368K since sold in May 2012$18K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 4.3% higher than the average sale price ($626K) of 6 comparable homes.

SOLD JUL 14, 2026
$742,500
A
4 beds3.5 baths3,356 sq ft
55 Beverly Rd, Chester, NY 10918
Listing by Howard Hanna Rand Realty
SOLD AUG 18, 2026
$580,000
B
5 beds3 baths2,983 sq ft
9 Mount Ridge Ct, Monroe, NY 10950
Listing by RE/MAX Benchmark Realty Group
SOLD JUL 8, 2026
$700,000
C
4 beds3.5 baths2,780 sq ft
7 Park Pl, Chester, NY 10918
Listing by Century 21 Full Service Realty
SOLD MAR 9, 2026
$550,000
D
4 beds3 baths2,288 sq ft
12 Juniper Ln, Monroe, NY 10950
Listing by Houlihan Lawrence Inc.
SOLD JUN 1, 2026
$660,000
E
4 beds2.5 baths2,506 sq ft
34 Booth Rd, Chester, NY 10918
Listing by Century 21 Full Service Realty
SOLD MAY 7, 2026
$525,000
F
4 beds3.5 baths2,280 sq ft
132 Neptune Dr, Monroe, NY 10950
Listing by eRealty Advisors, Inc

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Earn from this home

Sell

$462,888

Est. take-home

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Refinance

Est. cash available

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Rent

$3,937/mo

Redfin rental estimate

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Market trends in 10918, NY

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

97.1%

1.0% MoM

Median sale price

$445K

$63K MoM

Avg. days on market

48d

14 days MoM

Recently sold homes

7 MoM

New listings for sale

NEW 10 HRS AGO
$380,000
3 beds2.5 baths1,331 sq ft
4704 Whispering Hls, Chester, NY 10918
Listing by Sahagian Realty LLC
$360,000
3 beds2.5 baths1,331 sq ft
3409 Whispering Hls, Chester, NY 10918
Listing by Howard Hanna Rand Realty
NEW 27 HRS AGO
$1,685,000
6 beds7.5 baths— sq ft
69 Cedar Pond Ln, Chester, NY 10918
Listing by Prominent Properties Sotheby's International Realty-Alpine, (201) 768-9300
OPEN SUN, 2PM TO 4PM
$649,999
3 beds3 baths2,902 sq ft
3561 Rte 94, Chester, NY 10918
Listing by Howard Hanna Rand Realty
$374,900
3 beds1.5 baths1,644 sq ft
260 Gibson Hill Rd, Chester, NY 10918
Listing by Keller Williams Realty
3D WALKTHROUGH
$299,000
2 beds1 bath1,084 sq ft
2124 Whispering Hls, Chester, NY 10918
Listing by Howard Hanna Rand Realty
$374,900
3 beds2.5 baths1,331 sq ft
2921 Whispering Hls, Chester, NY 10918
Listing by ARC Realty 1 in Sales
$290,000
2 beds1.5 baths1,053 sq ft
1005 Whispering Hls, Chester, NY 10918
Listing by Century 21 Full Service Realty
OPEN SUN, 3PM TO 5PM
$749,000
4 beds2.5 baths2,599 sq ft
121 Conklingtown Rd, Chester, NY 10918
Listing by MS Realty Group USA, Inc
$550,000
3 beds2 baths1,583 sq ft
50 Hambletonian Ave, Chester, NY 10918
Listing by Howard Hanna Rand Realty
See all

Provided by Redfin

Sale history for 27 Dug Rd

Year

Property tax

Land + Additions

Assessment*

2025

$13,814 (+4.7%)

$61,300 + $136,000

$197,300

2024

$13,194 (+3.1%)

$61,300 + $136,000

$197,300

2023

$12,791 (+1.5%)

$61,300 + $136,000

$197,300

2022

$12,600 (−1.0%)

$61,300 + $136,000

$197,300

2021

$12,722 (−0.9%)

$61,300 + $136,000

$197,300

2020

$12,837 (+1.8%)

$61,300 + $136,000

$197,300

2019

$12,608 (+3.8%)

$61,300 + $136,000

$197,300

2018

$12,152 (+3.9%)

$61,300 + $136,000

$197,300

2017

$11,694 (+2.0%)

$61,300 + $136,000

$197,300

2016

$11,470 (+11.1%)

$61,300 + $136,000

$197,300

2015

$10,321 (+0.3%)

$61,300 + $136,000

$197,300

2014

$10,291

$61,300 + $136,000

$197,300

Tax history for 27 Dug Rd

Year

Property tax

Land + Additions

Assessment*

2025

$13,814 (+4.7%)

$61,300 + $136,000

$197,300

2024

$13,194 (+3.1%)

$61,300 + $136,000

$197,300

2023

$12,791 (+1.5%)

$61,300 + $136,000

$197,300

2022

$12,600 (−1.0%)

$61,300 + $136,000

$197,300

2021

$12,722 (−0.9%)

$61,300 + $136,000

$197,300

2020

$12,837 (+1.8%)

$61,300 + $136,000

$197,300

2019

$12,608 (+3.8%)

$61,300 + $136,000

$197,300

2018

$12,152 (+3.9%)

$61,300 + $136,000

$197,300

2017

$11,694 (+2.0%)

$61,300 + $136,000

$197,300

2016

$11,470 (+11.1%)

$61,300 + $136,000

$197,300

2015

$10,321 (+0.3%)

$61,300 + $136,000

$197,300

2014

$10,291

$61,300 + $136,000

$197,300

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

Public record

Beds

Baths

3.5

Stories

Lot width

—

Lot depth

—

Lot size

2.5 Acres

Year renovated

—

Sq. Ft.

2,728

Year built

1977

Style

Single Family Residential

County

Orange County

APN

332289A00800000010132200000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 13, 2026.

Property details

Parking

Parking Information
2 Car (Detached), Garage Parking

Interior

Bathroom Information
# of Baths (Full): 3
# of Baths (1/2): 1

Interior Features
# of Fireplaces: 2
Attic: Dormer, Scuttle
Basement: Finished, Walk-Out

Cooling & Heating
# of Heating Zones: 4
A/C: Central
Heating: Baseboard

Room Information
# of Finished Rooms (Total): 9

Room 1 Information
Room Type: Living Room
Room Level: 1

Room 2 Information
Room Type: Living Room
Room Level: 2

Room 3 Information
Room Type: Master Bedroom
Room Level: 1

Room 4 Information
Room Type: Additional
Room Level: 2

Room 5 Information
Room Type: Additional
Room Level: Lower

Room 6 Information
Room Type: Bathroom
Room Level: 1

Room 7 Information
Room Type: Bathroom
Room Level: 2

Room 8 Information
Room Type: Bathroom
Room Level: Lower

Room 9 Information
Room Type: Bedroom
Room Level: 2

Room 10 Information
Room Type: Dining Room
Room Level: 1

Room 11 Information
Room Type: Family Room
Room Level: Lower

Room 12 Information
Room Type: Kitchen
Room Level: 1

Room 13 Information
Room Type: Laundry Room
Room Level: Lower

Room 14 Information
Room Type: Lavatory
Room Level: 2

Room 15 Information
Room Type: Bedroom
Room Level: 2

Room 16 Information
Room Type: Bedroom
Room Level: 2

Room 17 Information
Room Type: Bedroom
Room Level: 2

Exterior

Building Information
Year Renovated: 1993
Year Built Exception: Estimated
Vinyl

Property Information
Amenities: Deck, Pantry, Pond Frontage, Privacy, Sprinkler Lawn System, Stream, Wall-to-Wall Carpet, Cul de Sac
Included: Attic Fan, Central Vacuum, Cook Top, Dishwasher, Dryer, Garage Door Opener, Intercom, Oven/Range, Refrigerator, Wall Oven, Washer, Whirlpool Tub

Lot Information
Sq. Ft. (Total): 2,728
Lot Description: Easement, Level, Partially Wooded, Stone/Brick Wall
Lot Size Area: 2.5000
Has Water Access

Financial

Tax Information
Tax Year: 2011
Tax Amount: $10,157

Utilities

Utility Information
Heating Fuel: Above-Ground Oil
Sewer: Septic
Water Heater: Electric Stand-Alone
Water Description: Drilled Well

Location

School Information
School District: Monroe-Woodbury
Elementary School: North Main Street
Junior Middle High School: M.W.M.S
High School: M.W.H.S

Location Information
Village: None
City: Chester Town
County/Parish: Orange County
Hamlet: Chester
Post Office: Chester

Public facts

Beds: 5
Baths: 3.5
Sq. Ft.: 2,728
Stories: 2.0
Lot Size: 2.5 acres
Style: Single Family Residential
Year Built: 1977
Year Renovated: —
County: Orange County
APN: 332289A00800000010132200000

Home facts updated by county records on Aug 13, 2026

Around this home

Schools

North Main Street School

Public 2-5 • Assigned • 3.0mi

5/10

Monroe Woodbury Middle School

Public 6-8 • Assigned • 5.3mi

5/10

Monroe Woodbury High School

Public 9-12 • Assigned • 5.5mi

6/10

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

4/10 Heat Factor

7 days above 96° 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

2 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 8.6 hours in June and 4 hours in December, placing it below the U.S. average for solar exposure.

8.6 hrs

4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$621,000 – $752,000

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Nearby similar homes

$849,900

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3D WALKTHROUGH

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Listing by Preferred Properties Real Esta

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Listing by Keller Williams Realty

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Listing by Serhant LLC

New listings for sale in 10918

NEW 10 HRS AGO

$380,000

3 beds2.5 baths1,331 sq ft

4704 Whispering Hls, Chester, NY 10918

Listing by Sahagian Realty LLC

$360,000

3 beds2.5 baths1,331 sq ft

3409 Whispering Hls, Chester, NY 10918

Listing by Howard Hanna Rand Realty

NEW 27 HRS AGO

$1,685,000

6 beds7.5 baths— sq ft

69 Cedar Pond Ln, Chester, NY 10918

Listing by Prominent Properties Sotheby's International Realty-Alpine, (201) 768-9300

OPEN SUN, 2PM TO 4PM

$649,999

3 beds3 baths2,902 sq ft

3561 Rte 94, Chester, NY 10918

Listing by Howard Hanna Rand Realty

$374,900

3 beds1.5 baths1,644 sq ft

260 Gibson Hill Rd, Chester, NY 10918

Listing by Keller Williams Realty

3D WALKTHROUGH

$299,000

2 beds1 bath1,084 sq ft

2124 Whispering Hls, Chester, NY 10918

Listing by Howard Hanna Rand Realty

$374,900

3 beds2.5 baths1,331 sq ft

2921 Whispering Hls, Chester, NY 10918

Listing by ARC Realty 1 in Sales

$290,000

2 beds1.5 baths1,053 sq ft

1005 Whispering Hls, Chester, NY 10918

Listing by Century 21 Full Service Realty

OPEN SUN, 3PM TO 5PM

$749,000

4 beds2.5 baths2,599 sq ft

121 Conklingtown Rd, Chester, NY 10918

Listing by MS Realty Group USA, Inc

Home values near 27 Dug Rd

Data from public records.

Address	Redfin Estimate
77 Dug Road, Chester, NY 3 Beds \| 2.5 Baths \| 1748 Sq. Ft.	$597,271
40 Dug Road, Chester, NY 3 Beds \| 2 Baths \| 1888 Sq. Ft.	$538,458

Address	Redfin Estimate
37 Dug Road, Chester, NY 4 Beds \| 2.5 Baths \| 2500 Sq. Ft.	$626,204
55 Dug Road, Chester, NY 3 Beds \| 2.5 Baths \| 1944 Sq. Ft.	$641,303

Address	Redfin Estimate
23 Dug Road, Chester, NY 4 Beds \| 2.5 Baths \| 2408 Sq. Ft.	$660,515
51 Dug Road, Chester, NY 3 Beds \| 2 Baths \| 1519 Sq. Ft.	$616,722

Property information provided by HGMLS when last listed in 2011. This data may not match . Learn more.

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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 10918, NY

Sale history for 27 Dug Rd

Tax history for 27 Dug Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 10918

Home values near 27 Dug Rd

More real estate resources