$699,999
0.17 Acres0.17 ac
9 Park Avenue
Highland Mills, NY 10930
Listed with Keller Williams Realty
$999,900
Est. $6,330/moChester, NY 10918 · Orange County
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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.
As reported by the listing office; verify enrollment with the district.
Listed with Cronin & Company Real Estate · Frank Muccari · Source: OneKey MLS
Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Nov 14, 2026, 7:07 PM ET. ©2026 One Key MLS.
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Market insights
Current listings
New in the last 30 days
16
Nov 2026
Average price
Active listings
$969,727
Nov 2026
Average days on market
Active listings
139 days
Nov 2026
Computed from 97 active OneKey MLS listings in Chester, NY.
$699,999
0.17 Acres0.17 ac
9 Park Avenue
Highland Mills, NY 10930
Listed with Keller Williams Realty
$950,000
5 Bed • 2.5 Bath • 3,206 Sq. Ft.5 bd · 2.5 ba · 3,206 sqft
36 Pearce Drive
Highland Mills, NY 10930
Listed with Keller Williams Hudson Valley
$949,900
7 Bed • 6 Bath • 5,625 Sq. Ft.7 bd · 6 ba · 5,625 sqft
10 Willys Court
Rock Tavern, NY 12575
Listed with Real Broker NY LLC