206 Greycourt Rd

Chester, NY 10918

$1,200,000
Price
—
Beds
—
Baths
4,032 Sq. Ft.
$298 / Sq. Ft.
4,032
Sq. Ft.
$298
per Sq. Ft.
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Description

Incredible property! Municipal water! Monroe woodbury school district! Welcome to 206 Greycourt Road, Chester, NY A truly rare and remarkable offering in the heart of Orange County, Presenting an extraordinary opportunity to acquire a standout property with exceptional visibility, flexible “ OP” zoning, multiple structures, and limitless potential. Positioned on one of Chester's most highly visible corridors with easy access to Route 17, this distinctive property combines historic character, income...Incredible property! Municipal water! Monroe woodbury school district! Welcome to 206 Greycourt Road, Chester, NY A truly rare and remarkable offering in the heart of Orange County, Presenting an extraordinary opportunity to acquire a standout property with exceptional visibility, flexible “ OP” zoning, multiple structures, and limitless potential. Positioned on one of Chester's most highly visible corridors with easy access to Route 17, this distinctive property combines historic character, income potential, and future development possibilities in one compelling package. Situated within the Town of Chester's “OP” Zoning District, the property offers a level of flexibility seldom found in today's market. Whether your vision includes professional offices, hospitality related uses, boutique commercial ventures, residential income production, event oriented concepts, or a mixed-use redevelopment, the foundation is already in place for something truly special. At the heart of the property stands a magnificent Victorian residence, thoughtfully expanded in 1850 from the original home dating back to 1790, which now serves as the garage. Rich in history, architectural character, and timeless craftsmanship, this remarkable structure offers a rare glimpse into the region's past while providing an inspiring setting for the future. A classic rocking chair front porch sets a welcoming tone, inviting guests to slow down and appreciate the property's timeless charm. Beyond the front door, a grand foyer unfolds into an elegant formal living room that transitions effortlessly into a spacious family room, where soaring ceilings, original hardwood floors, and beautifully preserved period details create an atmosphere of warmth, character, and enduring sophistication. A formal dining room, beautiful kitchen, and convenient first-floor powder room complete the main level. Ascending the impressive staircase, the second floor offers four spacious bedrooms, an additional sitting room that could easily function as a fifth bedroom or office, a large full bathroom, and a dedicated laundry room. Above, a substantial walk-up attic provides exceptional storage or future expansion opportunities. Complementing the main residence is a second detached home featuring two bedrooms and one full bathroom, ideal for rental income (currently rented), caretaker accommodations, employee housing, or additional business flexibility. Two substantial barn structures further elevate the property's possibilities. One stands proudly as a striking architectural centerpiece ready for adaptive reuse, while the second offers the opportunity to restore and reimagine a piece of the property's rich history. Together, these structures provide endless potential for creative redevelopment, storage, workshops, event space, or specialty commercial applications. Infrastructure is equally impressive, with public water service and three separate water meters already in place, providing flexibility for multiple users or future configurations. Location remains one of the property's strongest assets. With unparalleled visibility, easy access to Route 17, and close proximity to the Villages of Chester, Goshen, and Monroe, this property is positioned at the crossroads of commerce, convenience, and growth. Nearby amenities include The Heritage Trail, award winning shopping, renowned local restaurants, farm markets, recreational destinations, and the highly sought after Monroe Woodbury School District. Properties of this caliber, character, and versatility are rarely available. Whether you're seeking a trophy investment, a headquarters location, an income producing asset, or the canvas for your next transformative project, 206 Greycourt Road offers an opportunity limited only by imagination. Additional property across the street also be available for the right buyer. Schedule your private tour today and discover the extraordinary potential of one of Chester's most captivating properties.
  1. Listed by Frank Muccari • Cronin & Company Real Estate
    P: (845)-744-6275 C: (845)-494-3678 frankmproperties@gmail.com

Property Details for 206 Greycourt Road

City/Township
Chester Town
Garage Spaces
2.00
Waterfront
No
LISTING UPDATED: 06/03/2026 08:44 PM

Property Details for 206 Greycourt Road

StatusActive
MLS #1003998
Days on Market7
Taxes$14,463 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeMulti Family
MLS TypeQuadruplex
Year Built1870
Lot Size3.20 AC / 139,392 SF
CountyOrange County
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Location

Listing Courtesy of Cronin & Company Real Estate
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Building Information for 206 Greycourt Road

Stories-Residences3Year Built1870Building Size-Lot Size3.20 AC / 139,392 SF

Payment Calculator

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$7,185 per month

30 year fixed, 6.36% Interest

Principal and Interest

$5,980

Property Taxes

$1,205

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 206 Greycourt Road

Summary
Location and General Information
  • Senior Community YN: No
  • Property Attached: No
  • Structure Type: Detached
  • State Or Province: NY
School Information
  • School District: Monroe-Woodbury
  • Elementary School District: Monroe-Woodbury
  • Elementary School: North Main Street
  • Middle Or Junior School District: Monroe-Woodbury
  • Middle Or Junior School: Monroe-Woodbury Middle School
  • High School District: Monroe-Woodbury
  • High School: Monroe-Woodbury High School
Unit Information
Unit Information
  • Number Of 1 Bedrooms: 0.0
  • Number Of 2 Bedrooms: 0.0
  • Number Of 3 Bedrooms: 0.0
  • Number Of 4 Bedrooms: 0.0
  • Building Units Total: 3
Taxes and HOA Information
Taxes and HOA Information
  • Parcel Number: 332289-003-000-0001-009.310-0000
  • Tax Assessed Value: $200,000.00
  • Tax Source: Municipality
  • Tax Year: 2025.0
Interior and Exterior Features
Interior Features
  • Amenities: Entrance Foyer, Formal Dining, Hardwood Floors As Seen, High Ceilings, Natural Woodwork, Original Details, Pantry, Public, Washer/Dryer Hookup
  • Interior Features: Entrance Foyer, Formal Dining, High Ceilings, Natural Woodwork, Original Details, Pantry, Washer/Dryer Hookup
  • Basement: Full, Unfinished
  • Attic Description: Walkup
  • Fireplace: Yes
  • Fireplaces Total: 3
  • Location Amenities: Hardwood Floors As Seen, Entry Foyer, Foyer, Formal Dining Room, High Ceilings, Original Details, Pantry, WD Hookup
  • Flooring: Hardwood
  • Basement: Yes
Exterior Features
  • Exterior Property Features: Driveway, Garage
  • Elevation Certificate: No
  • Construction Materials: Frame
Lot Information
  • Building Area Units: Square Feet
Parking
  • Parking Features: Driveway, Garage
  • Garage: Yes
  • Carport: No
Utilities
  • Cooling: None
  • Heating: Forced Air
  • Heat Fuel Type: Forced Air
  • Sewer: Septic Tank
  • Water Source: Public
  • Utilities: Electricity Connected
Green Features
  • Green Features: Forced Air
Agent
Payment and Rate
  • Down Payment Resource: Yes

Property History for 206 Greycourt Road

DateEvent & SourcePriceAppreciation
Jun 1, 2026

Listed (Active)

ONEKEY #1003998

$1,200,000—
DateEvent & SourcePrice
06/01/2026

Listed (Active)

ONEKEY #1003998

$1,200,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Schools near 206 Greycourt Road

This home is within Monroe-Woodbury Central School District.
Rating
School
Type
Grades
Distance
North Main Street School
Public - 2 to 5
Monroe Woodbury Middle School
Public - 6 to 8
Monroe Woodbury High School
Public - 9 to 12
Pine Tree Elementary School
Public - 2 to 5
Rating
School
Distance
North Main Street School
Public2 to 5

Monroe Woodbury Middle School
Public6 to 8

Monroe Woodbury High School
Public9 to 12

Pine Tree Elementary School
Public2 to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 206 Greycourt Road, Chester, NY 10918

206 Greycourt Road is a multi-family home for sale in Chester, NY 10918. This property was listed for sale on June 1, 2026 by Cronin & Company Real Estate, it's currently listed at $1,200,000. This listing's school district is Monroe-Woodbury Central School District. Nearby schools include North Main Street School, Monroe Woodbury Middle School and Monroe Woodbury High School. 206 Greycourt Road is a 0-bed, 0-bath, 4,032 sqft multi-family home built in 1870.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Cronin & Company Real Estate

Based on information submitted to the MLS GRID as of 06/03/2026 08:44 PM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. Use of the MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS of the Member Participant, if any, and as amended from time to time.