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$385,000
2 Beds ⋅ 2 Baths ⋅ 1023851 MLS
Bright and sunny two-bedroom home with a third room ideal for a home office, den, or guest room. Both bedrooms are located on the second floor. The main floor features beautiful hardwood floors, a spacious living room, and a separate dining room. Step out onto the deck and enjoy views of the neighboring pasture. Fantastic location just minutes from the charming town of Amenia and the Metro North train station. Nestled in an area renowned for its scenic beauty, farm to table restaurants, shopping and outdoor recreation. Conveniently located near the Litchfield Connecticut border offering easy access to all the Hudson Valley and Northwest Connecticut have to offer.

5 Lake Amenia Road, Amenia
$299,000
3 Beds ⋅ 1 Baths ⋅ 1021382 MLS
Beautifully maintained three-bedroom cottage overlooking the scenic Harlem Valley Rail Trail in the charming town of Amenia. This move-in-ready home has been thoughtfully updated with new electric, new windows and new insulation, improvements that offer comfort and peace of mind for years to come. Pride of ownership is evident throughout the well maintained interior and exterior. Step outside and enjoy the tranquil setting with direct views of the Harlem Valley Rail Trail, perfect for walking, biking and enjoying the natural beauty of the surrounding countryside. A spacious 10' x 16' utility shed offers excellent storage for tools, outdoor equipment or recreational gear. Whether you're looking for a full-time residence or the perfect weekend retreat, this inviting home is sure to impress. A wonderful opportunity to own a turnkey home in one of Dutchess County's most picturesque communities. 24 Rail Trail Way is a rare opportunity not to be missed.

24 Rail Trail Way, Amenia
$599,000
4 Beds ⋅ 3 Baths ⋅ 1011480 MLS
Elegant & Upscale - Completely renovated 4 bedroom, 2.5 bathroom farmhouse blending timeless charm with modern luxury. This stunning home features a chef-inspired gourmet kitchen with premium finishes, custom cabinetry, and high-end appliances, perfect for entertaining and everyday living. The luxurious primary suite offers a spa-like custom bathroom designed with exceptional craftsmanship, creating a private retreat. Thoughtfully updated throughout, this exceptional property delivers the character of a classic farmhouse with all the comforts of contemporary living. Close to the Harlem Valley Rail Trail, Sharon Playhouse, Silo Ridge, and Wassaic Metro North Train Station.

9 Depot Hill Road, Amenia
$1,250,000
3 Beds ⋅ 3 Baths ⋅ 1012838 MLS
Perfect opportunity to own a historic mixed-use colonial on 6.62 acres, zoned OC, walking distance to the center of Amenia, with extremely low taxes. 2,645 sq ft, masonry foundation, wood floors, asphalt shingle roof, baseboard heat plus heat pump, public water. The main floor is configured as a successful, working restaurant with all kitchen equipment included. The second floor contains a 2-bedroom apartment with a full bath, living room, kitchenette, and lofted office. Ample storage throughout. Grounds include mature gardens with hydrangea trellises. The acreage offers room for further development. Located near Metro-North rail service in the Northeast Central School District (Webutuck High School). Zoning permits continued restaurant use, retail conversion, or single-family residential.

6 Autumn Lane, Amenia
$85,000
977656 MLS
Discover the perfect canvas for your dream home. This BOHA-approved lot offers rare, highly sought-after "select-fill" soil- making it truly build-ready from day one. Just 1 hour and 40 minutes from New York City, this property gives you the best of both worlds: peaceful country living with effortless access to the city. Wake up each morning to breathtaking seasonal views and a sweeping open meadow right outside your window. The location is exceptional- just minutes from the Connecticut border, close to Massachusetts, and less than 5 minutes to the Wassaic train station for easy commuting. If you love recreation, wellness, or simply enjoying life, you’re in the perfect spot. Silo Ridge Field Club is less than 5 minutes away, offering world-class golf, dining, and activities. The Harlem Valley Rail Trail is also moments from your doorstep for biking, walking, and exploring nature. Medical care is conveniently nearby, with facilities within 5 minutes and Sharon Hospital less than15 minutes away. For leisure, you’re only a short drive from the local drive-in theater or the iconic Troutbeck Hotel- where you can dine, relax, or even spot a few Hudson Valley celebrities. This isn’t just a lot. It’s a lifestyle. A rare opportunity to build your future in one of the most beautiful, accessible, and desirable pockets of the Hudson Valley.

Old State Route 22, Amenia
$1,250,000
1008685 MLS
Perfect opportunity to own a historic mixed-use colonial on 6.62 acres, zoned OC, walking distance to the center of Amenia, with extremely low taxes. 2,645 sq ft, masonry foundation, wood floors, asphalt shingle roof, baseboard heat plus heat pump, public water. The main floor is configured as a successful, working restaurant with all kitchen equipment included. The second floor contains a 2-bedroom apartment with a full bath, living room, kitchenette, and lofted office. Ample storage throughout. Grounds include mature gardens with hydrangea trellises. The acreage offers room for further development. Located near Metro-North rail service in the Webutuck (Northeast) Central School District. Zoning permits continued restaurant use, retail conversion, or single-family residential.

6 AUTUMN Lane, Amenia
$549,000
3 Beds ⋅ 3 Baths ⋅ 1001908 MLS
An elevated retreat wrapped in small town charm. Experience airy, sophisticated living with 3 generously proportioned bedroom, 3 full baths, and a flowing floor plan. The lower-level suite framed by natural light is ideal for a mother/daughter set up, studio, workshop, home office or simply the additional open space. Designer touches — hardwood floors, crown molding, newer appliances, and silestone counters — create a polished, luxurious feel throughout. Outdoors, a sweeping wraparound deck reveals panoramic views of your own serene landscape, offering unmatched privacy and beauty. Located just minutes to the Wassaic Train Station and the Harlem Vally Rail Trail is a short walk or bike ride away. Taxes shown reflect full assessment.

21 Ohandley Drive, Amenia
$225,000
997760 MLS
Prime Mixed-use Development Opportunity Route 44 Amenia NY Exceptional mixed use property on highly traveled Route 44 in Amenia level cleared lot Excellent viability and high traffic count Town water available Ideal for retail ,office, residential, or mixed use project Conveniently located close too shopping dining, and local amenities Home on property has been removed Bring your vision to this ready to build property in a growing, high visibility location

5282 Route 44, Amenia
$399,000
3 Beds ⋅ 3 Baths ⋅ 995667 MLS
Welcome to Perrys Corners Rd, where timeless details and future vision come together. This 3 bedroom, 3 bath home features original hardwood floors preserved beneath the carpeting—an opportunity to restore warmth and authenticity. The finished lower level adds flexible space ideal for a creative retreat, home office, or entertainment zone. Step outside and discover private grounds that drift toward a serene stream, creating a natural oasis for gardeners, nature lovers, and anyone seeking quiet moments. With the Harlem Valley Rail Trail and Wassaic Train Station just minutes away, recreation and convenience are always within reach. A home with history, heart, and endless possibility.

126 Perrys Corners Road, Amenia
$189,000
993639 MLS
Westerly Ridge 7.9 acres with an elevated home site and extraordinary vistas of the rural countryside. The sunsets are magnificent, and the sun rises are invigorating. There is a well already installed and the BOHA has been renewed requires no fill. The Westerly Ridge Homeowners Association maintains the private road and keeps an eye on ensuring the integrity of values established from the beginning. The region is blessed with a huge variety of cultural and recreational activities. The Wassaic Train Station is minutes away. The path to the homesite has been cleared you should plan to make the trip to check out the gorgeous Town of Amenia. There is electric underground to the lot. The new purchasers will need to install the utilities and the driveway. Please do not enter this parcel or any other property on Westerly Ridge without the list agent.

#2 Lot #2 Westerly Ridge Drive, Amenia
$365,000
3 Beds ⋅ 1 Baths ⋅ 989555 MLS
Situated on 2.45 acres of land in the Town of Amenia, you will find this three-bedroom ranch style home. The grounds are lovely, with a private, mostly level yard. The home provides single level living and the property includes a detached three bay garage with a one-bedroom apartment on the second floor. Perfect property for a first-time home buyer or an investor. Conveniently located minutes from Metro North train stations and the enjoyable Harlem Valley rail trail. Just a short drive to Millbrook or Sharon, CT.

24 Wilson Eaton Road, Amenia
$8,600,000
986998 MLS
Set amid rolling fields and protected countryside, Hounds Pond Farm captures the essence of Hudson Valley living. Spanning 342 acres in the scenic Amenia Valley, the land unfolds across open meadows, sweeping vistas, and tranquil views over Round Pond, with the foothills of the Berkshire Mountains rising in the distance. Whether envisioned as a private estate, working farm, or recreational retreat, the property offers exceptional flexibility with 70% open land and multiple prime building sites. A newly renovated three-bedroom cottage provides an immediate foothold while future plans take shape. Located just minutes from Millerton, Silo Ridge, and Metro-North service at Wassaic—and bordering the Harlem Valley Rail Trail—this is a rare opportunity to own a significant piece of one of the region’s most beautiful and enduring landscapes.

156 Sharon Station Road, Amenia
$899,000
8 Beds ⋅ 4 Baths ⋅ 979113 MLS
Whether you're seeking a property with positive cash flow, a multigenerational living setup, or the ability to live on-site while generating rental income, this unique offering delivers exceptional versatility. The property features two separate duplex buildings along with an adjacent lot, providing added privacy and future expansion possibilities. Each duplex consists of two well-appointed 2-bedroom units, all with private entrances and ample parking. The units are currently occupied, offering immediate income for investors. Ideally located just minutes from the Village of Amenia, Millerton, and Millbrook, the property offers convenient access to shopping, dining, and everyday amenities. Commuters will appreciate proximity to the Wassaic Metro-North Train Station, while outdoor enthusiasts can enjoy the nearby Harlem Valley Rail Trail—perfect for walking, running, and biking. Don’t miss this opportunity to own a flexible, income-producing property in a highly desirable location.

762-764-766 Old Route 22, Amenia
$2,300,000
13 Beds ⋅ 7 Baths ⋅ 973862 MLS
Step into a turn key investment with 9 years of profitable short term rental history and a business backed by a long standing, proven financing track record! This exceptional 1790 Georgian style estate comes with three standalone cottages, all fully renovated and operating as highly sought after vacation rentals. With commercial zoning already in place, this property blends historic charm, modern luxury, and serious income potential, while also offering a rare opportunity for future conversion into a boutique hotel or resort. Guests flock to this private country escape for its elegant main residence featuring wide plank hardwood floors, high ceilings, a library, music room, billiard room, and wine cellar, and return for the tranquility of the manicured grounds complete with a heated pool, putting green, walking trails, and a serene pond. Currently fully booked, this estate generates significant revenue even after accounting for full service cleaning and lawn maintenance. Whether you choose to live in the main home and rent out the three cottages, lease all four residences, or explore a larger scale hospitality concept, this is a rare chance to own a high performing asset with built in lifestyle benefits. Minutes from local hiking, dining, and the Berkshires, this is your chance to own a legacy property and a cash flowing business in one.

18 Stagecoach Lane, Amenia
$250,000
958125 MLS
8 Yellow City Rd offers a rare opportunity to build your dream home in a prime location. This residential lot is fully approved for four bedroom home and already has underground pow installed, making it truly ready to build Enjoy an incredible setting with great views, just minutes from town and steps from the rail trail-perfect for walking, biking, and out door living. well has been drilled as well

8 yellow city rd, Amenia
$8,650,000
5 Beds ⋅ 7 Baths ⋅ 955653 MLS
Refined Luxury. Rare Direct Lakefront Home within the Coveted Silo Ridge Community. 5 Luxurious En-suite Bedrooms Including 2 on Main Level. Jaw Dropping Great Room with Fireplace & Access out to Large Covered Porch with Major Lake & Mountain Views. Extremely High Quality Construction with Numerous Luxury Appointments Including: Lutron 1-Touch Lighting; Multi-Zone Sound System; 4-Season In Ground Pool/Spa; Heated 3-Car Attached Garage; Electric Shades Throughout; 2 Screened Porches with Powered Screens & Built in Heaters. Finished Lower Level with 2 Bedrooms, 2.5 Baths & Family Room with Direct Access to Heated Pool/Spa & Cabana with Fireplace. 1-Mile to Metro North Train & Arms Distance to all the Hudson Valley has to Offer. The Best of Silo Ridge for Sale. Exceptional!

292 Wood Duck Road, Amenia
$129,000
896113 MLS
Rare opportunity to own vacant land in a Hamlet Mixed Use area. We have a detailed plan for a proposed build that would be 60x 28 and ample parking. The exposure on Route 343 is exceptional. Any building is subject to planning and zoning approval.

Route 343, Amenia
$1,900,000
M419993 MLS
Indulge in breathtaking privacy, featuring a couple of extraordinary homesites harmoniously integrated into the enchanting landscape of meadows and woodlands. This premium land offering maintains a commitment to organic farming, ensuring a connection to nature. Tucked away from the road, this is an optimal setting for those desiring a distinguished location with ample space for exploration, cultivation, animal husbandry, and children's playful adventures. A pristine canvas ready for your dreams to blossom and thrive. Enjoy proximity to the Wassaic Train Station, as well as the charming villages of Millerton, Sharon, Salisbury CT, and the Hamlet of Amenia, just minutes away. Taxes and assessment shown w Ag Exemption

PERRYS CORNERS Road, Amenia
$2,379,000
H6310518 MLS
An opportunity to own a magnificent combination of two rural properties. Explore this enchanting yet tranquil 206.14 acres of rolling hills, mature forests and ample meadow that is currently in organic crop production. There are a couple of steep slopes that contribute to buffering a few captivating and extremely private home sites. The terrain is ideal for a retreat and multiple dwellings. Maybe this becomes the getaway from the getaway. This property fronts both Cascade Mountain Rd as well as Perrys Corners Rd. There are no covenants and restrictions. Located a few miles outside of the Hamlet of Amenia and the Wassaic Train Station is minutes away. Pine Plains, Millerton, Millbrook and Salisbury, Sharon and Kent, CT are scenic drives away.

Cascade Mt / Perrys Corners, Amenia
$479,000
M419986 MLS
Discover the perfect spot for your modern or log home - a private parcel perched on a hill, embraced by the tranquility of the forest. These idyllic home sites provide an ideal retreat from the hustle and bustle of city life. Just minutes away from the Wassaic Train Station and the Harlem Valley Rail Trail, this location invites you to plan your escape. Lace up your hiking boots and schedule a tour to embark on your next adventure. PRIVATE,Wooded Acres:49.63

CASCADE MOUNTAIN Road, Amenia

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . 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.