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$449,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 1 Full Bath
  • 1 Partial Bath
  • 1 Car Garage
  • Updated 13 days ago
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See This Home
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Welcome to 66 Whitetail Run - Chester, NY. Tucked back from the road on an ample, tree-lined lot, this charming contemporary colonial offers the perfect blend of privacy and convenience in the Monroe-Woodbury school district. Surrounded by nature and filled with birdsong, this peaceful setting feels like a retreat while still being close to all local amenities. Step inside to a bright, open living room featuring soaring ceilings, a wood-burning fireplace, and oversized windows that flood the space with natural light. Hard floors flow throughout the main level, leading to a spacious eat-in kitchen with granite countertops, plus a formal dining room perfect for hosting gatherings and special occasions. This 3-bedroom, 1.5-bath home also offers both bathrooms newly renovated, along with the convenience of a main-floor laundry room with a new washer and dryer. An attached one-car garage adds everyday practicality, while the back patio invites you to unwind and enjoy the tranquil, wooded surroundings. Don't miss your opportunity to make this move-in ready home yours!

Full Property Details for 66 Whitetail Run

General

  • Price: $449,000
  • Taxes: $11,768
  • Status: Active
  • Type: Single Family
  • Source: Long_Island
  • MLS ID: 1033721
  • Updated: 8/14/2026
  • Added to Site: 26 day(s) ago

Interior

  • Number of Rooms: 10
  • Interior Features: Chefs Kitchen, Eat-in Kitchen, Entrance Foyer, Formal Dining, Granite Counters, High Ceilings, Natural Woodwork, Original Details, Primary Bathroom, Stone Counters, Storage, Walk Through Kitchen, Washer/Dryer Hookup
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Living Room, Masonry, Wood Burning
  • Appliances: Dishwasher, Dryer, Electric Oven, Electric Range, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Oil Water Heater
  • Laundry Facilities: Yes

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 1
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Electric Dryer Hookup, In Hall, Inside, Washer Hookup

Parking

  • Garage: Yes
  • Garage Spaces: 1
  • Parking Features: Attached, Driveway, Garage, Off Street, Private

Location

  • County: Orange County

School Information

  • High School District: Monroe-Woodbury
  • Elementary School: North Main Street
  • Middle School: Monroe-Woodbury Middle School
  • High School: Monroe-Woodbury High School

Heating & Cooling

  • Cooling Type: Wall/Window Unit(s)
  • Heating Type: Baseboard, Oil

Utilities

  • Sewer: Septic Tank
  • Water: Well
  • Utility Description: Cable Connected, Electricity Connected

Structural Information

  • Architectural Style: Colonial, Contemporary
  • Detached/Attached: Detached
  • Construction: Frame
  • Sq. Ft. Source: Public Records
  • Year Built: 1983

Lot Features

  • Lot Size (Acres): 0.9183
  • Lot Size (Sq. Ft.): 40,002

Financial Considerations

  • Tax Amount: $11,768.52

Disclosures and Reports

  • Special Conditions: None
  • Property ID: 332089-052-000-0001-105.000-0000

Listed by Howard Hanna Rand Realty

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Listing agents

— 66 Whitetail Run —

  • Howard Hanna Rand Realty

  • Howard Hanna Rand Realty

845-928-9691

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 66 Whitetail Run

School District:Monroe-Woodbury Central School District
NameGradesDistance
North Main Street School
212 North Main Street, Monroe, NY 10950
2-53.4 mi
Smith Clove Elementary School
21 Smith Clove Rd, Woodbury, NY 10917
K-16.3 mi
Monroe Woodbury Middle School
199 Dunderberg Rd, Woodbury, NY 10917
6-86 mi
Monroe Woodbury High School
155 Dunderberg Rd, Woodbury, NY 10917
9-126 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 66 Whitetail Run Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/02/2026
Listed
$449,000
66.3%
MLS
8/07/2018
Sold
$270,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 66 Whitetail Run

Year
Property Taxes
Change
Tax Assessment
Change
2024
$11,025
100%
$42,700
—
2021
-100%
$42,700
—
2021
$10,149
-41%
$42,700
—
2020
$17,143
113%
$42,700
—
2018
$8,066
6%
$42,700
—
2017
$7,604
—
$42,700
—
2016
$7,592
—
$42,700
—
2015
$7,594
-1%
$42,700
—
2015
$7,657
3%
$42,700
—
2013
$7,450
—
$42,700
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 66 Whitetail Run

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Down Payment
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*These costs are estimates, and the interest rates assume exceptional credit standing.

Listed by Howard Hanna Rand Realty

66 Whitetail Run, Chester, NY 10918 (MLS# 1033721) is a Single Family property with 3 bedrooms, 1 full bathroom and 1 partial bathroom. 66 Whitetail Run is currently listed for $449,000 and was received on August 02, 2026. Want to learn more about 66 Whitetail Run? Do you have questions about finding other Single Family real estate for sale in Chester? You can browse all Chester real estate or contact a Coldwell Banker agent to request more information.

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