$999,900

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… Read More 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. Read Less

Listing Courtesy of Cronin & Company Real Estate.

Listing Snapshot

Days Online

Last Updated

Aug 13, 2026

Property Type

Quadruplex

Square Ft.

4,032

Lot Size

3.2 Acres

Year Built

1870

Property Tax

$14,463

MLS Number

1003998

30 Days Snapshot Of 10918

$593k

(avg) sold price

-100%

homes sold

135

(avg) days on market

Snapshot

Area Map

Additional Details

Basement

Description: Full, Unfinished

Building

Building Area: 4032, Construction Materials: Frame, Year Built: 1870

Cooling

Details: None

Fireplaces

Total Fireplaces: 3

Floors

Flooring: Hardwood

Garage

Garage Spaces: 2

Heating

Heating: Forced Air

Lot

Acres: 3.2

Utilities

Sewer: Septic Tank, Water Source: Public, Utilities: Electricity Connected

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