Dover Plains Homes for Sale

Welcome to Dover Plains, New York – a hidden gem nestled in the scenic Dutchess County, where charm meets convenience. This quaint town offers a perfect blend of rural tranquility and urban accessibility. With its picturesque landscapes, vibrant community, and rich history, Dover Plains is an ideal place to call home.

Dover Plains boasts a variety of outdoor activities, from hiking the nearby Appalachian Trail to enjoying leisurely afternoons at local parks. The area is known for its friendly atmosphere and strong sense of community, making it a wonderful place for families, young professionals, and retirees alike. The town is also conveniently located near the bustling hubs of Poughkeepsie and Beacon, providing easy access to shopping, dining, and cultural events.

When it comes to real estate, Dover Plains offers an impressive selection of homes for sale that cater to diverse tastes and budgets. Whether you're searching for a charming single-family home with a spacious yard, a cozy cottage with character, or a modern townhouse, you'll find an array of options that suit your lifestyle. Many properties feature stunning views of the surrounding countryside, providing a serene backdrop for your everyday life.

With a strong sense of community, excellent schools, and a wealth of recreational opportunities, Dover Plains is more than just a place to live – it's a place to thrive. Explore the homes for sale in this delightful town and discover the perfect setting for your next chapter. Your dream home in Dover Plains awaits!

Newest Dover Plains Homes for Sale

$275,000

5 Beds ⋅ 2 Baths ⋅ 1032197 MLS

Surrounded by nature. An affordable compound in the quiet hamlet of Dover Plains—an increasingly rare opportunity to own two dwellings for the price of one. This unique property features a 3-bedroom/1-bath residence and a separate 2-bedroom/1-bath residence, 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, and surrounded by nature. Enjoy the best of both worlds: tranquil rural living with convenient access to Route 22 and the Metro-North train station just 2 miles away. Both offer full, unfinished basements providing excellent storage or future potential. The structures share a common well and septic system. Oil tanks above ground. Ideal for owner-occupants, extended family living, or investment purposes, this is a truly unique opportunity in an excellent location. This is a "Cash Only, "As Is" sale.

14-16 Glen Hill, Dover Plains

$549,000

3 Beds ⋅ 2 Baths ⋅ 1029543 MLS

It is all in the details with this sophisticated Millbrook retreat. Perched high off the main road, this very private property is dreamy. The entrance wrap around porch welcomes you home immediately. The open living space commands attention with beamed ceilings, crown moldings, V-groove plank paneled walls and doors, and more. There is a wood burning stove, hardwood flooring, paned windows, and Central Air Conditioning. Many are double pane thermal windows. The country kitchen is open to the dining area, leading with glass sliders out to the over-sized screened in porch, providing another great living and entertaining space. There is a full bathroom with shower on this level also. This leads to the gorgeous office/bedroom featuring high coffered/beam ceiling, wood paneled walls, custom built in desks, shelving and closet. This room has access both to the front drive with glass sliders and another door to the backyard. Up the stairs you will find a smart wet bar, complete with sink and refrigerator. The guest room is next which includes 6 over 6 paned thermal windows. The extra- large primary bedroom is a sanctuary, including a sitting area, vaulted ceiling and board and batten wood paneling. The large open rain-shower with tub and double sink bathroom is spa-like and calming. Mature trees and forest provide peace and quiet and privacy. This is just minutes from charming Millbrook Village, and also a short ride to Wassaic Metro North train station. Millbrook and other villages nearby provide full dining and shopping options including numerous farm markets and overall country recreation. This is all just two hours from NYC. Welcome to the Hudson Valley!

766 Route 343, Dover Plains

$595,000

3 Beds ⋅ 3 Baths ⋅ 1016112 MLS

A European Inspired Oasis in Dover Plains! This meticulously cared for custom built home is being offered by the original owners for the first time. The impressive front entrance is where the grace and style begins. This 2,409 square foot home has too many custom features to list-making it a MUST SEE! In the primary residence you will find a primary bedroom, 2 additional bedroom, 2 full baths, one with a marble tile shower and floor, updated appliances, recessed lighting. The dining room has glass doors to the expansive, European baluster railed, veranda with breathtaking views overlooking the property, river and distant mountains. The lower level includes a legal 1 bedroom, 1 bath accessory apartment with living room. Perfect for multigenerational living. A one room studio is also on the lower level. A great space for an artist studio or overnight guests. Both lower level spaces open to the grand stone patios with fountain surrounded by stone walls. Sited on over 2 acres of lush gardens with fruit trees, a custom built stone fountain, patios, statuary, masonry stone walls with pillars, two outbuildings and over 325 feet of level backyard and all with access to the 10 Mile River for fishing, kayaking and summer enjoyment. If privacy, tranquility, and living with waterfront accesses is your idea of a dream home-it is all here! 4 Minutes to Dover Plains Metro North Station!

20 Craig Lane, Dover Plains

$575,000

3 Beds ⋅ 3 Baths ⋅ 1008883 MLS

This beautifully maintained 3-bedroom, 2.5-bath Colonial is being offered for sale for the very first time. Lovingly built and cared for by its original owner, the home is set on a scenic 2.7-acre lot with open lawn, mature landscaping, established vegetable garden, and an idyllic creek along the rear of the property. From the moment you arrive, the peaceful setting and classic curb appeal make a lasting impression. A wide covered front porch welcomes you in, and wraps around to a rear deck that offers another inviting outdoor space overlooking the beautiful, well-kept grounds. Inside, high ceiling and large windows fill the home with natural light and highlight a comfortable, well-designed floor plan. Features include hardwood floors, a bright dining area, a spacious living room with fireplace/wood-stove insert, and an easy flow into the kitchen with breakfast bar seating. Thoughtfully maintained over the years, this home offers the rare combination of usable acreage, established landscaping, privacy, and classic Hudson Valley charm. The frontage road is currently in the town paving process, adding another welcome improvement. Conveniently located near Route 22, the Village of Millbrook, Metro-North, the Harlem Valley Rail Trail, Dover-area recreation, and a short drive to the Connecticut border. Don't miss the opportunity to own a rare gem. This happy home is move-in ready and waiting for it's next owner. Come experience the peace and charm of country living at its best.

226 Cart Road Unit #C, Dover Plains

$599,408

4 Beds ⋅ 2 Baths ⋅ 996401 MLS

Sophisticated country living in the desirable Millbrook area within the highly regarded Millbrook Central School District. Ideally located close to the charming village, local amenities, and the Wassaic Station for convenient Metro-North access to New York City. Privately set on 2.06 picturesque acres, this light-filled 4-bedroom, 2-bath Cape offers the perfect blend of comfort, versatility, and lifestyle. Designed to accommodate a variety of needs, the exceptional heated three-bay garage with soaring ceilings and expansive upper level creates endless possibilities for car enthusiasts, artists, writers, entrepreneurs, fitness enthusiasts, or those seeking a spacious home office or creative studio. The inviting interior features wood floors and tile throughout the main level, with an effortless open-concept layout ideal for both everyday living and entertaining. The vaulted-ceiling family room is filled with natural light and showcases tile flooring, a custom built-in entertainment cabinet, and a chimney ready for a pellet or wood stove. The adjoining kitchen flows seamlessly into the living and dining spaces, creating a warm and welcoming atmosphere. A formal dining room and spacious living room continue the home’s airy, connected design, while a first-floor bedroom and full bath with laundry closet provide flexibility for guests or one-level living. Upstairs, the primary suite offers vaulted ceilings and a private ensuite bath, accompanied by two additional bedrooms. Step outside to the rear deck overlooking the peaceful grounds—perfect for outdoor dining, entertaining, or simply enjoying the tranquil setting. A storage shed adds additional convenience to this thoughtfully designed property. A rare offering combining refined country style, functional workspace, and an ideal location in the heart of the Hudson Valley.

810 ROUTE 343, Dover Plains

$499,000

3 Beds ⋅ 2 Baths ⋅ 996553 MLS

Privately nestled on 3 serene acres in the rolling hills of Dover Plains, this beautifully reimagined country retreat offers an exceptional blend of privacy, refined modern updates, and effortless indoor-outdoor living. Set far back from the road and surrounded by mature trees and picturesque natural scenery, 256 Hammond Hill Road delivers a peaceful lifestyle with extraordinary entertaining space both inside and out. Accessed via a deeded right-of-way, the property offers a uniquely private setting while maintaining convenient accessibility. This inviting 3-bedroom, 2-bath residence spans approximately 1,788 square feet and features a bright, open-concept layout filled with natural light and thoughtfully curated finishes throughout. Completely renovated kitchen and bathrooms elevate the home with a sophisticated, modern aesthetic while preserving its warmth and timeless character. The stunning kitchen flows seamlessly into the dining and living areas, creating an airy atmosphere ideal for both everyday living and entertaining on any scale. Rich hardwood flooring, oversized windows, freshly painted interiors, and newly installed designer light fixtures throughout the kitchen, bathrooms, exterior, and hallways further enhance the home’s polished presentation. Major mechanical and functional improvements provide additional peace of mind, including newer appliances with most approximately two years old, a refrigerator replaced within the last year, and a recently updated well pump. The home also includes a newer pellet stove, approximately 3–4 years old, accompanied by both pellets and wood for the wood-burning stove, offering warmth and ambiance throughout the colder seasons. In addition to the primary living spaces, the home features an expansive bonus room offering remarkable versatility for a home office, guest accommodations, recreation space, fitness studio, or additional lounge area tailored to a variety of lifestyle needs. One of the property’s most captivating features is the oversized rear deck spanning the back of the home, creating a spectacular extension of the living space with multiple seating and dining areas overlooking tranquil wooded surroundings. Whether hosting summer gatherings, enjoying quiet mornings with coffee, or relaxing beneath the stars, the outdoor setting captures the essence of refined country living. Additional highlights include central air conditioning, included washer and dryer, a SimpliSafe security system that may be expanded by future owners, and an oversized garage with an additional oil tank for supplemental heat. Town of Washington documentation reflects updated approvals and retroactive Certificates of Occupancy for prior improvements, with no known violations currently on file. Conveniently located in the heart of Dutchess County, just moments from local shops, restaurants, hiking trails, Metro-North, and the charming nearby towns of Pawling, Millbrook, and Amenia, this exceptional offering combines modern enhancements, flexible living space, expansive outdoor entertaining, and timeless country elegance less than two hours from Manhattan.

256 Hammond Hill Road, Dover Plains

$1,950,000

3 Beds ⋅ 1 Baths ⋅ 976571 MLS

A few minutes east of Route 22 on the Dover/Millbrook border in the municipality of Washington, sits 109+ acres of picturesque countryside. Used prior as a dairy farm, this exceptional offering presents a rare opportunity to bring your farming lifestyle dreams to life, or an equestrian property. Comprised of 4 distinct parcels totaling 109+ acres, the property blends open fields, wooded landscapes, water features, and classic agricultural structures to create a truly versatile and inspiring setting. The largest parcel, spanning 88.46 acres, offers a beautiful mix of approximately 25 cleared acres and expansive mature hardwood forest. Portions were fenced for cattle, while a gently meandering stream traces the western border, feeding into a small pond at the southern tip. Trails wind through the woods, inviting exploration, and the land slopes gently to the north, revealing sweeping, breathtaking views from its higher elevations. One could build an incredible estate surrounded by nature and absolute privacy. Just below, the 10.37-acre parcel forms the heart of the former cattle farm, complete with two residences, the continuation of the stream along its western and southern edges, and the iconic red barns and silo that define the property’s rural character. One home is a vintage 1900s 2 story farmhouse offering 3 bedrooms, 1 bath, and 1,482 SF across six rooms, complete with a welcoming open front porch and currently occupied by the property’s caretaker. The second residence is a spacious 2,272 SF ranch-style home featuring 2 bedrooms, 1 1/2 baths, generously sized rooms with high ceilings, and an enclosed porch. This home is currently rented for $2,900 per month, providing immediate income potential. Supporting the agricultural use are several accessory buildings, including a substantial two-story cow barn built in 1920 with 3,800 SF, a 480 SF barn dating to 1950, a detached one-car garage built in 1940 offering 1,056 SF, and additional storage sheds. The 9.82-acre parcel is a level hay field, ideal for crops or livestock, and benefits from its own gated entrance along Tinker Town Road, offering both convenience and flexibility. An additional 1.04-acre parcel sits conveniently across the street, completing the ensemble. If additional land is desired, there is an adjacent 332+ acres that could also be bundled with this purchase, creating a total of 441.99 acres. This offering is not only a picturesque rural retreat but also a savvy investment, with the potential for agricultural tax exemptions to be reinstated if managed accordingly. Despite its serene seclusion, the property is just minutes from Route 22, the Dover Metro North train station, and the charming local villages of the Hudson Valley, offering the perfect balance of country living and modern accessibility.

21-23 Tinker Town Road, Dover Plains

$3,750,000

7 Beds ⋅ 7 Baths ⋅ 990563 MLS

Rarely does an offering of this scale and provenance come to market. Set across more than 114 acres, Honey Lane Farm is a private estate of exceptional beauty—three distinct period residences forming a serene, self-contained retreat in the heart of the Harlem Valley. The four-bedroom mid-19th century main house is both refined and inviting, bathed in southern light and thoughtfully updated for modern living. A spacious chef’s kitchen anchors the home, flowing seamlessly into elegant dining and living rooms, a relaxed family room, and expansive outdoor entertaining spaces. Details such as a wood-burning fireplace, rich hardwood floors, bluestone terraces, and a gracious screened porch elevate the experience. An in-ground pool and tranquil wildlife pond complete the idyllic setting. A stately circular drive leads to the 1860s carriage house, offering a beautifully appointed two-bedroom guest residence. Further along, the 1929 Barn House provides yet another charming haven for hosting gatherings. Winding paths traverse a landscape of remarkable diversity—open meadows, mature woodlands, and picturesque waterways—while multiple elevated sites offer breathtaking panoramic views and future possibilities. Surrounded by over 1,000 acres of protected farmland along the Ten Mile River watershed, the estate ensures privacy without isolation. Just five minutes from Metro-North access in Dover Plains and Ten Mile River, Honey Lane Farm represents a rare convergence of history, scale, and enduring elegance.

151 Benson Hill Road, Dover Plains

$450,000

1 Beds ⋅ 1 Baths ⋅ 932753 MLS

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, featuring commanding glass and skylights, a custom-crafted interior and a cozy wood stove that makes efficiency luxurious. The main geodesic dome is complemented by a studio seamlessly integrated into the landscape — perfect for an art studio, office, or workspace. The infrastructure is robust: on-grid power with off-grid capability, a dedicated well and full septic system. A spring-fed natural swimming pond, aerated and stocked with fish, doubles as a functional fire-safety reservoir (an insurance-advantage you rarely see). A new half-mile gravel driveway ensures privacy and serenity from the main road. Zoned and fully permitted as a short-term rental through Dutchess County, The Geosphere Retreat is income-ready if that is what you seek. Comparable homes in the region are generating $1,000–$2,000 per week. With further subdivision potential (2-acre minimum lots), and agricultural tax incentives available, this isn’t just a home — it’s a platform for both current income potential—and future upside. Positioned in Dover, NY, two hours from New York City, in an area where growth is quietly gathering pace, including nearby Silo Ridge, and One&Only in development, complete with commuter-link access via Metro-North’s Harlem Line. The Geosphere awaits to deliver a statement, a sanctuary, and a truly unique value proposition.

105 Sand Hill Road, Dover Plains

$2,475,000

4 Beds ⋅ 5 Baths ⋅ 929427 MLS

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 spring-fed pond, orchard, and private hiking trails. The architecture balances tradition and innovation, with a glass breezeway linking the historic structure to a stone and glass master wing—winner of multiple 2025 design awards. Large windows, wide doorways, and a barrier-free layout reflect both aesthetic and practical considerations for modern living and aging in place. Period details like exposed beams, wide-plank floors, and a kitchen fireplace ground the home in its heritage, while updates like solar panels and geothermal temperature control bring it into the future. The kitchen, framed by dark soapstone counters and classic cabinetry, opens to a large screened porch overlooking the backyard and pond. A brick fireplace and custom inset pantry bring both warmth and functionality. The home also includes a temperature-controlled 1,000-bottle wine cellar, ideal for collectors. A two-story barn/garage offers additional workspace or storage. Outdoors, Stone Church Creek winds through the property on its way to the iconic Dover Stone Church Preserve, which directly abuts the rear boundary. This 175-acre protected park features over three miles of well-maintained trails and one of Dutchess County’s most photographed natural features: a dramatic waterfall spilling through a cave carved into ancient stone. With the preserve quite literally at the edge of the property, the connection to nature is immediate and immersive—offering an unmatched sense of privacy and place. Whether as a weekend escape or a full-time homestead, 56 Northrup is a rare blend of design, sustainability, and pastoral beauty—anchored by smart systems, architectural pedigree, and extraordinary surroundings.

56 Northrup Road, Dover Plains

Start Your Search

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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.