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- Description
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Street View
$999,900
Monthly Est:$4,977
-- Bed
- -- Bath
4,032sqft
206 Greycourt Rd, Chester, NY 10918
$999,900
$4,977/moEst:
Get Pre-Approved
Quadruplex
Built in 1870
$-- HOA
3.2 acres lot
$248/sq.ft
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 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.
- Houzeo last checked: 12 hours ago
- Listing updated: August 20, 2026 at 7:10 am
- Listing Provided by: Frank Muccari (845) 494-3678 | Cronin & Company Real Estate (845) 744-6275
- Source: OneKey MLS-NY as distributed by MLS GRID | MLS#: 1003998

Property Details
Status
Pending
Type
Multi Family
No. of Stories
-
County
City
Neighborhood
--
Year Built
1870
HOA Fees
-
Finished Area
4,032 sqft
Lot Size
3.2 acres lot
Basement Area
- sqft
MLS Name
OneKey MLS
MLS Number
1003998
MLS Status
Pending
Days on Market
154
Cumulative Days on Market
79

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Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedroom: --
Bathroom: --
Interior
Flooring
Hardwood
Sewer
Septic Tank
Heating
Forced Air
Interior Features
Entrance Foyer, Formal Dining, High Ceilings, Natural Woodwork, Original Details, Pantry, Washer/dryer Hookup
Cooling
None
Construction
Year Built
Year Built: 1870
Home type
Quadruplex
Construction Materials
Frame
Utilities & Energy
Water Source
Public
Utilities
Electricity Connected
Basement
Full, Unfinished
Parking Features
Driveway, Garage
Price History
| Date | Event | Price |
|---|---|---|
08/19/2026 Source: | Pending | $999,900 -16.68% $248/sqft |
06/01/2026 Source: | Listed for Sale | $1,200,000 $298/sqft |
Find Homes by Property Features in Chester, NY
Based on information from OneKey MLS® through Nov 02, 2026, 02:16PM as submitted to and distributed by MLS GRID. 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. IDX information is provided exclusively for consumers’ personal non-commercial use. It 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. The use of the MLS GRID Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. © 2026 OneKey MLS. All rights reserved.
Advertising Broker: Derek Greene | The Greene Realty Group
