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

$599,000

4 Beds ⋅ 3 Baths ⋅ 1050747 MLS

Welcome to your ultimate private riverfront oasis! Perfectly nestled on 1.8 meticulously landscaped acres in the scenic heart of Dover Plains, this breathtaking custom Contemporary Colonial offers an exceptional blend of modern sophistication, premium upgrades, and endless outdoor adventure. Whether you are seeking a serene, year-round residence or a spectacular weekend country getaway, this magnificent property delivers a truly unparalleled, resort-like lifestyle experience that must be seen to be fully appreciated. Step inside to a grand foyer featuring soaring cathedral ceilings that instantly set a tone of spacious elegance. The main level has been thoughtfully designed to maximize effortless daily living and lavish entertaining. It boasts a brilliant, sun-drenched living room serving as the perfect gathering space. Flow seamlessly into the formal dining room, an elegant setting for hosting meals and dinner parties. The heart of the home is the expansive, well-equipped kitchen, offering abundant counter space and cabinetry for culinary creativity. A beautifully appointed, marble-tiled half bathroom completes the spectacular main floor layout, offering convenience for guests. The upper level features four generously sized bedrooms, providing fantastic flexibility to accommodate a home office or personal fitness space. The crown jewel of the second floor is the expansive primary suite. This private sanctuary is complete with a massive walk-in closet providing exceptional storage, and a spa-inspired private en-suite bathroom where you can unwind in tranquility. The upper level also offers a stylish, full guest bathroom designed with elegant finishes, alongside the modern convenience of a dedicated private laundry room conveniently positioned near the bedrooms. Step outside to discover an outdoor enthusiast's dream come true. Entertain large crowds or host summer barbecues on the expansive rear wooden deck, or simply relax with your morning coffee on the classic blue stone patio. The true centerpiece of this resort-like backyard is the immaculate, heated saltwater in-ground swimming pool. The pool now features a brand-new liner, ensuring it is completely ready for endless summer enjoyment. The sprawling grounds are a dedicated horticulturist's delight. The property has beautifully maintained landscaped garden beds ready for seasonal plantings, and several mature fruit trees providing a wonderful seasonal bounty. Beyond the manicured gardens, the property extends to directly abut the gently flowing Tenmile River. Launch a canoe or kayak right from your own property line, or enjoy premier trout fishing from your private backyard riverbank. Complete with a two-car attached garage offering ample room for vehicles and extra storage, reliable above-ground oil heating, and convenient proximity to local public transportation, schools, shopping, and community amenities. This rare offering seamlessly blends the tranquility of a private nature retreat with the modern conveniences of a fully upgraded luxury home. Move right in and begin experiencing resort-like country living at its finest!

46 Craig Lane, Dover Plains

$670,000

3 Beds ⋅ 4 Baths ⋅ 1049190 MLS

Privately set on 3.6 acres in Dover Plains, this spacious Colonial offers a unique and versatile layout with plenty of room to make it your own. Built in 2005, the home features 3 legal bedrooms, 3 full bathrooms and 1 half bathroom, with a standout feature being the legal accessory apartment complete with its own private entrance. The main living space offers a traditional Colonial layout with generous room throughout. Upstairs, the primary bedroom features a walk-in closet and private full bathroom, along with 2 additional bedrooms, a hallway full bathroom and a versatile bonus room ideal for a home office or flex space. The legal accessory apartment adds another level of versatility, featuring its own kitchen, living room, bedroom, full bathroom and separate entrance. Whether used for extended household living, guests or simply additional private space, it is a valuable feature that can be difficult to find. Outside, the 3.6-acre setting provides a sense of privacy and separation with plenty of space to enjoy the property. An above-ground pool offers a great spot to spend summer days, while the surrounding acreage provides room for outdoor entertaining, recreation, gardening and more. Located approximately 15 minutes from the Village of Millbrook, the home offers a private country setting while remaining convenient to local shopping, dining and area amenities. With its acreage, flexible floor plan and legal accessory apartment, this property offers a combination of space and possibilities ready for its next owner.

250 Highview Road, Dover Plains

$59,900

2 Beds ⋅ 2 Baths ⋅ 1049355 MLS

This is a 55 and over community.

100 Park Drive, Dover Plains

$220,000

3 Beds ⋅ 2 Baths ⋅ 1047515 MLS

Welcome to Tally Ho, a desirable 55+ community in Dover Plains, where comfortable living meets convenience. This well-maintained 2021 28'x52' manufactured home offers a 1456 sq. ft. of spacious and inviting floor plan with plenty of room to relax and entertain. The large living room provides a welcoming gathering space, while the generously sized eat-in kitchen features stainless steel appliances, abundant cabinetry, and excellent storage. The kitchen is both functional and comfortable, with plenty of room for dining and everyday living. The spacious primary bedroom offers a full en-suite bathroom and a large walk-in closet, creating a comfortable private retreat. A shed is also included, providing additional storage for tools, outdoor equipment, and more. Enjoy the amenities Tally Ho has to offer, including a clubhouse, in-ground pool, bocce, and a variety of community activities. The lot rent includes taxes, adding to the convenience of ownership. Ideally located just minutes from the Metro-North train station, Harlem Valley Rail Trail, shopping, restaurants, and other local amenities. This move-in-ready home offers low-maintenance living in a welcoming 55+ community in the beautiful Harlem Valley.

60 Celeste Drive, Dover Plains

$315,000

3 Beds ⋅ 1 Baths ⋅ 1028097 MLS

Welcome to 39 N Farm Rd! Choices, choices, choices! Whether you're looking for the ease of single-level living, a private home for your family, or a property with plenty of room to make it your own, this charming 3-bedroom, 1-bath home offers it all. Beautiful hardwood floors flow throughout the main living areas, creating a warm and inviting atmosphere. The eat-in kitchen features ample countertops and cabinet space, with convenient access to the dining and living rooms—perfect for everyday living and entertaining. The full bathroom includes a tub/shower, vanity, and linen closet. The primary bedroom is situated in a corner of the home, offering abundant natural light, while the two additional bedrooms are generously sized and overlook the picturesque yard. The unfinished basement provides abundant storage space, along with a washer and dryer and convenient access to the attached one-car garage. Outside, the gravel driveway leads to a private, level backyard with beautiful views of the fields beyond. With plenty of space and endless possibilities, the backyard is ready for whatever you envision—from a pool or garden to a pitch-and-putt area, play space, or simply a peaceful place to relax and enjoy the outdoors. Come see all the possibilities 39 N Farm Rd has to offer!

39 N Farm Drive, Dover Plains

$89,999

4 Beds ⋅ 2 Baths ⋅ 1041997 MLS

House in need of full rehab. Cash only. Feet away from 10 Mile River in backyard.

70 May Lane Extension, Dover Plains

$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

$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

$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

$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

$795,000

4 Beds ⋅ 4 Baths ⋅ 981862 MLS

Stunning Riverfront Retreat offers serene water views and the luxury of fishing and kayaking right in your own backyard. Beautifully renovated three-bedroom home is complemented by a one-bedroom pool house that works perfectly as a guest cottage - true resort-style living. Open-concept living and dining areas are filled with natural light, featuring two sets of French doors that lead to a spacious deck—ideal for seamless indoor-outdoor entertaining. Expansive windows showcase picturesque views of the famous Duchess County Ten Mile River. Designer kitchen includes recessed lighting, stylish pendant accents, and stainless-steel appliances. Pamper yourself in a primary en-suite with vaulted ceilings, a generous closet and spa-like bathroom complete with Jacuzzi tub, separate tiled shower, double vanity and water closet. A second bedroom with its own en-suite bath provides comfort and privacy for guests. Walkout lower level offers exceptional versatility, featuring a large family room perfect for a home office, gym, or recreation space, along with a third bedroom and full bathroom. The pool house enhances the property with its own open living area, dining space, kitchenette, fourth bedroom and full bath plus additional 2nd floor loft storage. An enclosed sun porch overlooks the inviting in-ground heated pool to extend the swimming season. These three acres feel like a private park, with nearly 700 feet of direct river frontage. Enjoy leisurely afternoons with games like bocce or horseshoes, then gather around the firepit on cool evenings. This one-of-a-kind property blends natural beauty, tranquility, and modern comfort—an exceptional place to call home.

360 Old State Route 22, Dover Plains

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