Dover Plains, NY Homes for Sale

23 Clearview Rd, Wingdale, NY – Multi-Family OpportunityTwo homes for the price of one! This unique multi-family property sits on a .38-acre lot and includes a detached two-car garage—perfect for extra storage or workshop space. The main home features a primary bedroom with an ensuite bath, plus two additional bedrooms, a spacious kitchen, and a comfortable living room. The second home offers

Peggy MacLeay-Generoso McGrath Realty Inc

A true country retreat on 109 picturesque acres on one of Millbrook’s most coveted roads, Tower Hill. This extraordinary country estate offers a rare blend of elegance, comfort, and timeless charm. The main residence, originally built in 1909 and remodeled in 2002, features five or six bedrooms, four full bathrooms, and three half bathrooms, designed for both everyday living and grand

Byron Anderson Compass Greater NY, LLC

This home is in good condition and is located in a well maintained 55 and over community. Monthly rentincludes: taxes, water, streetlights and garbage pickup.

Richard Rennia Richard A. Rennia

ONE OF A KIND PROPERTY HUNTING LAND AND 1,368 sq ft cabin.plus 462 sq ft loft. sleeps 8. three land parcels. 70 ACRES 50 ACRES and 12.4 ACRES for a total of 132.4 Acres. Part in forestry program as you might know. DBH over every 13 inches diameter Brest high is considered marketable trees approx. every 13 or 14 years a percentage of the younger trees have reached maturity to be harvested.

John Melchior Howard Hanna Rand Realty

This home is in good condition and located in a well maintained 55 and over community. Monthly rent includes: taxes, water, streetlights and garbage pickup.

Richard Rennia Richard A. Rennia

An affordable multifamily compound in the quiet hamlet of Dover Plains—an increasingly rare opportunity to own two homes for the price of one. This unique property features a 3-bedroom/1-bath residence and a separate 2-bedroom/1-bath home, both in solid condition with some TLC needed to make them your own. Set on a picturesque parcel at the end of a country road, the setting is peaceful, private,

Barry Malawer Coldwell Banker Realty

The Geosphere is a convergence of visionary design, tactical investment and natural sanctuary. Set on 7.18 secluded acres in the heart of Dover Plains, this fully legal, architect-designed geodesic residence and studio building give you something unmistakably distinctive: a home that feels like art, and a property that can perform like an asset. Inside, the striking residence is fully winterized,

Sheneur Menaker Hudson Modern Co

Welcome to your private equestrian retreat, just 4 miles from the Harlem–Valley Wingdale Train Station, 4 miles to charming Kent, CT, a mile away to the Appalachian Trail & easy access to Route 7 & Route 22. Set on a secluded private road off Lake Ellis, this property offers both convenience & privacy. Equestrian amenities include a main barn with 6 (12x10) stalls w/ hay loft, heated wash stall,

Christine Ricci Keller Williams NY Realty

This two-family home offers both flexibility and steady potential—ideal for investors or owner-occupants. Whether you’re looking to move in and enjoy the setting or rent out both units, the choice is yours. Conveniently located near transportation, shops, and daily amenities, the home offers a peaceful and private setting.Both 2 bedroom units are currently rented. The upstairs unit rents for

Crystal Colombo Compass Greater NY, LLC

This 2900+ colonial on an 8+ acre lot offers mountain views and beautiful sunrise views. Bring your vision to customize and update this home to your taste. This property is eligible under the Freddie Mac First Look initiative through 1/11/2026. Sold as-is. ***AGENTS – MUST see confidential remarks and all MLS listing attachments for additional instructions***

Igor Krasnoperov Rising Star Realty

Located in Dover Plains, this charming 3-bedroom, 2-bath Colonial offers 2,230 sq. ft. of living space on a 1.27-acre corner lot and includes a detached 2-car garage. Inside, you’ll find an inviting open-concept layout. The main level is perfect for entertaining or everyday living and features a spacious living room with hardwood floors, a large dining room that flows seamlessly to an eat-in

Robert Washburn RE/MAX Ace Realty

Just 90 miles from New York City, at the end of a winding, tree-lined drive, a world unfolds where time slows down, and life takes on a different rhythm. This is the Hudson Valley escape you’ve been waiting for. A custom-built home with detached workshop on nearly five private acres, where every detail was designed to bring comfort, inspiration, and beauty into daily living.The moment you

Lindsay Stevens eXp Realty

Discover an incredible investment opportunity in highly desirable Dover Plains! This multi-family property sits on a beautiful, private lot just shy of an acre, offering endless potential for expansion, added income, or future development. Surrounded by a serene landscape and located in a prime location, this property appeals to both investors and end-users alike. Whether you’re looking to

German Nielsen Newman Realty Inc

At the very end of a quiet country road, you'll find 56 Northrup — a stunning, architect-designed retreat blending 19th-century farmhouse charm with thoughtful, award-winning modern design. Originally built in 1870 and reimagined by NYC architects Neumann & Rudy, this 33-acre property includes a restored main house, a sleek single-story primary suite addition, and expansive grounds featuring a

Adam Hade Compass Greater NY, LLC

Perched above the rolling hills of Millbrook Hunt Country with sweeping Catskill Mountain views, this idyllic retreat and exceptional equestrian estate spans 185 ultra-private acres. Once the beloved property of Margaret Carnegie, only child of Andrew Carnegie, the estate preserves a rich legacy of elegance and prestige. Originally built in 1865, it has been thoughtfully expanded to blend

John Oliveira Douglas Elliman of Connecticut