Off market jul 2020 for $344K

$590,006

Est. refi paymentEst. refi $2,742/mo

•

1,992

sq ft

66 Dug Rd, Chester, NY 10918

About this home

Look no further for the perfect commuter home away from the city . Renovated Bi-Level nestled on top of a woodland hill in a private setting. Enjoy scenic views and a picturesque mountain backdrop. Inside you will find 3 Bedrooms and 2 full gorgeous bathrooms. The kitchen is also well appointed with new stainless appliances, double oven, custom lighting , shaker style cabinets , contemporary tile and gleaming quartz counters. There is plenty of room outside to entertain on your front and rear decks. Relax in your lower level family room as well as an extra bonus flex space downstairs for a guest room, home office or playroom. Two car garage and circular driveway with plenty of space for your vehicles. Highly sought after Monroe Woodbury School District. Removed but yet central to all the amenities of Chester & Monroe. 8 Mins to the park and ride and 5 Mins to Walton & Round Lakes. Low taxes make this a fantastic deal. Ready for new owners.Move in ready and that perfect escape from the city. Additional Information: ParkingFeatures:2 Car Attached,

Single-familyProperty Type

1972Year Built

2 acresLot Size

$296Est. Price/Sq.Ft.

2 spacesParking

Listing by Darnell Williams • Charles Rutenberg Realty, Inc.

Listing by Maritza Ruiz • Charles Rutenberg Realty, Inc.

Bought with Darnell Williams • Charles Rutenberg Realty, Inc.

Bought with Maritza Ruiz • Charles Rutenberg Realty, Inc.

Redfin checked: a minute ago

•Source:OneKey® MLS as Distributed by MLS Grid #H5127656

Redfin Estimate

$590,006

$245K since sold in July 2020$8,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 6.5% higher than the average sale price ($554K) of 6 comparable homes.

SOLD FEB 9, 2026
$535,000
A
4 beds2 baths1,928 sq ft
219 Bull Mill Rd, Chester, NY 10918
Listing by Keller Williams Realty
SOLD OCT 1, 2026
$495,000
B
4 beds3 baths1,792 sq ft
18 Southside Dr, Monroe, NY 10950
Listing by Keller Williams Realty
SOLD AUG 13, 2026
$500,000
C
3 beds2 baths1,600 sq ft
65 Ludlam Rd, Monroe, NY 10950
Listing by Weichert Realtors
SOLD JUN 24, 2026
$580,000
D
3 beds2 baths1,680 sq ft
135 Highland Ave, Monroe, NY 10950
Listing by Keller Williams Realty
SOLD AUG 17, 2026
$580,000
E
3 beds2.5 baths1,830 sq ft
11 Cunningham Dr, Monroe, NY 10950
Listing by MS Realty Group USA, Inc
SOLD JUN 22, 2026
$635,000
F
3 beds2.5 baths1,954 sq ft
25 Sugarloaf Mountain Rd, Chester, NY 10918
Listing by Cronin & Company Real Estate

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Earn from this home

Sell

$312,055

Est. take-home

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Refinance

Est. cash available

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Rent

$2,813/mo

Redfin rental estimate

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Market trends in 10950, NY

Last updated September 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

98.2%

0.3% MoM

Median sale price

$530K

$18K MoM

Avg. days on market

55d

9 days MoM

Recently sold homes

8 MoM

New listings for sale

COMING SOON
$239,900
2 beds1 bath1,084 sq ft
2313 Whispering Hls, Chester, NY 10918
Listing by R2M Realty Inc
$1,725,000
4 beds2.5 baths3,348 sq ft
20 Goshen Rd, Chester, NY 10918
Listing by eXp Realty
$1,850,000
3 beds2.5 baths2,404 sq ft
7 Greycourt Rd, Chester, NY 10918
Listing by KW Hudson Valley United
$599,000
4 beds4.5 baths3,326 sq ft
111 Ayr Rd, Chester, NY 10918
Listing by Curasi Realty, Inc.
$750,000
4 beds3.5 baths3,100 sq ft
985 Craigville Rd, Chester, NY 10918
Listing by Houlihan Lawrence Inc.
See all

Provided by Redfin

Sale history for 66 Dug Rd

Date

Event

Price

OneKey® MLS as Distributed by MLS Grid #H5127656

Jul 17, 2020

Sold

$344,900

$173/sq ft

Jun 8, 2020

Relisted

—

Mar 25, 2020

Pending

—

Mar 19, 2020

Pending

—

Feb 20, 2020

Relisted

—

Feb 19, 2020

Listing Removed

—

Dec 24, 2019

Relisted

—

Dec 23, 2019

Listing Removed

—

Dec 18, 2019

Listed

$339,500

$170/sq ft

OneKey® MLS as Distributed by MLS Grid #H5034527

Nov 5, 2019

Listing Removed

—

Aug 25, 2019

Listed

$339,900

$171/sq ft

OneKey® MLS as Distributed by MLS Grid #H4927569

Jun 21, 2019

Sold

$189,900

$95/sq ft

Jun 6, 2019

Pending

—

May 2, 2019

Listed

$189,900

$95/sq ft

Bilevel located in Chester Town on 2.0 acres. This home has two bedrooms on the main level along with kitchen, dining room, family room, and bathroom. The lower level features a family room with wood burning stove, another bedroom, bathroom, laundry room and two car garage. Enjoy the two decks in the front and back of the house. Bring this home back to its original state. Additional Information: ParkingFeatures:2 Car Attached,

OneKey® MLS as Distributed by MLS Grid #H4837940

May 1, 2019

Listing Removed

—

Jan 4, 2019

Price Changed

$209,900

$105/sq ft

Dec 5, 2018

Price Changed

$214,900

$108/sq ft

Sep 19, 2018

Price Changed

$229,900

$115/sq ft

Aug 11, 2018

Listing Removed

—

Aug 11, 2018

Listed

$239,900

$120/sq ft

Public Records

Nov 14, 2007

Sold

$378,010

$190/sq ft

Public Records

Jun 23, 1995

Sold

$134,000

$67/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$12,442

$57,500 + $119,600

$177,100

2025

$12,442 (+4.7%)

$57,500 + $119,600

$177,100

2024

$11,884 (+3.2%)

$57,500 + $119,600

$177,100

2023

$11,516 (+1.7%)

$57,500 + $119,600

$177,100

2022

$11,329 (−1.0%)

$57,500 + $119,600

$177,100

2021

$11,439 (−0.9%)

$57,500 + $119,600

$177,100

2020

$11,541 (−41.5%)

$57,500 + $119,600

$177,100

2019

$19,722 (+80.5%)

$57,500 + $119,600

$177,100

2018

$10,926 (+3.9%)

$57,500 + $119,600

$177,100

2017

$10,515 (+1.9%)

$57,500 + $119,600

$177,100

2016

$10,315 (+1.5%)

$57,500 + $119,600

$177,100

2015

$10,163 (+0.2%)

$57,500 + $119,600

$177,100

2014

$10,140

$57,500 + $119,600

$177,100

Tax history for 66 Dug Rd

Year

Property tax

Land + Additions

Assessment*

2026

$12,442

$57,500 + $119,600

$177,100

2025

$12,442 (+4.7%)

$57,500 + $119,600

$177,100

2024

$11,884 (+3.2%)

$57,500 + $119,600

$177,100

2023

$11,516 (+1.7%)

$57,500 + $119,600

$177,100

2022

$11,329 (−1.0%)

$57,500 + $119,600

$177,100

2021

$11,439 (−0.9%)

$57,500 + $119,600

$177,100

2020

$11,541 (−41.5%)

$57,500 + $119,600

$177,100

2019

$19,722 (+80.5%)

$57,500 + $119,600

$177,100

2018

$10,926 (+3.9%)

$57,500 + $119,600

$177,100

2017

$10,515 (+1.9%)

$57,500 + $119,600

$177,100

2016

$10,315 (+1.5%)

$57,500 + $119,600

$177,100

2015

$10,163 (+0.2%)

$57,500 + $119,600

$177,100

2014

$10,140

$57,500 + $119,600

$177,100

*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

Stories

Lot width

—

Lot depth

—

Lot size

2 Acres

Year renovated

—

Sq. Ft.

1,992

Year built

1972

Style

Single Family Residential

County

Orange County

APN

332289A00800000010161100000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Oct 8, 2026.

Property details

Parking

Parking Information
Parking Total: 2
Parking Features: Attached, Driveway, Garage Door Opener

Interior

Fireplace Information
Fireplace Features: Wood Burning Stove

Heating & Cooling
Cooling: Attic Fan, Wall/Window Unit(s)
Heating: Baseboard, Electric, Propane

Interior Features
Interior Features: Chandelier,Eat-in Kitchen,Granite Counters
Appliances: Dishwasher, Electric Water Heater, ENERGY STAR Qualified Appliances, Microwave, Refrigerator
Levels: Bi-Level, Two
Patio And Porch Features: Deck

Room Information
Basement YN: No
Attic: Pull Stairs
Rooms Total: 8
Basement: None

Bathroom Information
Bathrooms Full: 2

Exterior

Exterior Features
Construction Materials: Frame
Waterfront YN: No

Lot Information
Additional Parcels YN: No
Lot Features: Near Public Transit, Near School, Near Shops, Sloped, Views, Wooded

Property Information
Stories: 2
Living Area Source: Public Records
Property Sub Type: Single Family Residence
Property Condition: Estimated

Financial

Tax Information
Tax Year: 2018
Tax Source: Municipality
Tax Annual Amount: $10,515

Financial Information
Buyer Financing: FHA

Utilities

Utility Information
Electric Company: Orange & Rockland
Sewer: Septic Tank
Utilities: Trash Collection Private

Location

HOA Information
Association Amenities: Park

School Information
Elementary School: Pine Tree Elementary School
Middle Or Junior School: Monroe-Woodbury Middle School
High School: Monroe-Woodbury High School
High School District: Monroe-Woodbury

Location Information
Directions: Bull Mill Rd to Dug Rd , GPS
County Or Parish: Orange County

Community Information
Community Features: Park

Public facts

Beds: 3
Baths: 2.0
Sq. Ft.: 1,992
Stories: 1.0
Lot Size: 2 acres
Style: Single Family Residential
Year Built: 1972
Year Renovated: —
County: Orange County
APN: 332289A00800000010161100000

Home facts updated by county records on Oct 8, 2026

Around this home

Schools

North Main Street School

Public 2-5 • Assigned • 2.8mi

5/10

Monroe Woodbury Middle School

Public 6-8 • Assigned • 5.1mi

5/10

Monroe Woodbury High School

Public 9-12 • Assigned • 5.3mi

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 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

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

$561,000 – $679,000

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Home values near 66 Dug Rd

Data from public records.

Address	Redfin Estimate
77 Dug Road, Chester, NY 3 Beds \| 2.5 Baths \| 1748 Sq. Ft.	$579,931
69 Dug Road, Chester, NY 4 Beds \| 3 Baths \| 3006 Sq. Ft.	$667,549

Address	Redfin Estimate
37 Dug Road, Chester, NY 4 Beds \| 2.5 Baths \| 2500 Sq. Ft.	$630,992
55 Dug Road, Chester, NY 3 Beds \| 2.5 Baths \| 1944 Sq. Ft.	$642,187

Address	Redfin Estimate
40 Dug Road, Chester, NY 3 Beds \| 2 Baths \| 1888 Sq. Ft.	$545,037
51 Dug Road, Chester, NY 3 Beds \| 2 Baths \| 1519 Sq. Ft.	$610,271

Property information provided by OneKey® MLS as Distributed by MLS Grid when last listed in 2019. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 10950, NY

Sale history for 66 Dug Rd

Tax history for 66 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 66 Dug Rd

More real estate resources