Refine Search
Map
Sort by
$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
$314,900
2 Beds ⋅ 1 Baths ⋅ 1028548 MLS
Two bedroom, one bath cottage on an amazing pastoral setting on a 6.16 acre lot in the town of Dover. Great place for a weekend retreat or year-round home. Bring your imagination and renovate this home to your needs. Amazing setting! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with rehab loan financing must be accompanied by a pre-qualification letter; cash offers with proof of funds. Please see agent remarks for access, showing instructions and offer presentation remarks.

122 Weil Road, Wingdale
$450,000
3 Beds ⋅ 3 Baths ⋅ 1025570 MLS
Welcome to the sought-after Wood Winds subdivision in the heart of Wingdale! This beautifully maintained 3-bedroom, 3-full bath home offers over 1,700 square feet of comfortable living space. Luxury vinyl plank flooring flows throughout, while the spacious kitchen features stainless steel appliances, granite countertops, and abundant cabinet space. The dining room opens through sliding glass doors to your own backyard retreat, where a heated in ground pool creates the perfect setting for relaxing, entertaining, and making the most of summer. Large windows throughout the home fill the space with natural light. The primary suite features a private ensuite bath, while two additional generously sized bedrooms share a full hall bath. The finished lower level offers a spacious recreation room or flexible living area complete with a third full bath—ideal for a mother/daughter set up, family room, home office, gym, or guest space. Conveniently located just minutes from the Harlem Valley-Wingdale Metro-North station, Route 22, local shops and restaurants, the Appalachian Trail, Dover Stone Church, and numerous parks and recreational opportunities, this home offers the perfect balance of neighborhood living and everyday convenience. Community water and sewer!

6 Hemlock Lane, Wingdale
$649,000
3 Beds ⋅ 3 Baths ⋅ 1025768 MLS
New construction home to be built ! This raised ranch home features 3 bedrooms and 3 full bathrooms and 2 car garage. The open floor plan connects the kitchen, dining room and living room. The primary bedroom with ensuite bathroom features a spa like walk in shower. The plans are approved and ready to build, don't miss the opportunity to customize this home

149 Johnson Road, Wingdale
$100,000
1025733 MLS
Beautiful flat building lot, no clearing needed! Board of health approved for 4 bedroom home and you only need a small septic on this lot which makes building a home here more cost effective! This level lot is perfect to build your dream home. Bring your own builder or use ours! We can help and assist the first time homebuyer build their dream home through the whole process.

9 Ter Bar Court, Dover Plains
$100,000
1025750 MLS
Land for sale with board of health approval- Approved plans for a 3 bedroom, 3 bathroom raised ranch home. Well is drilled, land is ready to start building your dream home today

149 Johnson Road, Wingdale
$110,000
1021316 MLS
Private country setting with abundant wildlife to enjoy. Ideally located a short driving distance from Millbrook to the West, Amenia to the North, on the East by Kent, CT, and the South by Pawling. BOHA until 2029, no fill required for a 3 or 4 bedroom home. Close to railroad for NYC commuters. Specific area is known as Ridgebrook Country Estates. Must see to appreciate!

7 BROOKVIEW Road, Dover Plains
$50,000
1020201 MLS
An expansive 2.7-acre parcel of land nestled serenely along a picturesque country road, offering a charming and tranquil setting.The land goes downhill from the road to a designated wetland and then rises quite sharply through mature woodland. This idyllic property is conveniently situated near the highly accessible and major thoroughfare, Route 22, ensuring ease of travel and connectivity to essential amenities and services.

Old Pawling Road, Dover Plains
$899,000
3 Beds ⋅ 2 Baths ⋅ 1015591 MLS
A rare opportunity for the dedicated equestrian, this beautiful gentleman’s farm is set on nearly 9 acres of gently rolling countryside, offering the ideal balance of privacy, usability and convenience. Whether you’re an active competitor, trail rider or simply seeking a peaceful horse property, this special offering provides the setting to pursue your passion. Perfect as a full-time residence or idyllic weekend getaway, the property offers a welcome escape from city life while remaining easily accessible. Horse show enthusiasts will appreciate the convenient proximity to many of the regions’ premier equestrian venues, training facilities and riding opportunities. The nearly 9 acres parcel provides ample space for paddocks, turnout and a sand riding ring. Beyond its equestrian appeal, the property also caters to the automotive enthusiasts. A spacious garage equipped with a vehicle lift provides the ideal place to work on your projects. Adding to the property’s versatility is a legal accessory apartment, perfect for extended family, guests, a caretaker or trainer. Spend your days riding, relaxing and enjoying the beauty of the surrounding countryside, then take advantage of the property’s convenient access to the Harlem Vally-Wingdale train station for seamless travel to and from NYC. Combining the charm for a gentleman’s farm with the lifestyle and conveniences sought by today’s horse owners, car enthusiasts and weekend retreat seekers, this exceptional property is a place where passions can flourish and country living is enjoyed to its fullest.

73 Lake Ellis Road, Wingdale
$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
$899,000
4 Beds ⋅ 4 Baths ⋅ 1015365 MLS
Beautifully situated on 5.5 private acres, this impressive home offers a gated entrance and a long private driveway leading to breathtaking mountain views and a peaceful setting. Relax on the charming rocking-chair front porch and enjoy the serenity of the surrounding landscaped front lawn. Step inside to a dramatic two-story foyer and an abundance of natural light. The spacious kitchen features granite countertops, ample cabinetry, and large windows that showcase the scenic mountain views and doors out to trex decking. Adjacent to the kitchen is a comfortable family room with access to the laundry room and the attached 3-car garage. A formal dining room and formal living room provide excellent spaces for entertaining, while numerous windows throughout the home bring the outdoor in. The main level also includes a convenient half bath. upstairs, the elegant staircase leads to the expansion primary suite that you enter through double doors. The primary bath features a jacuzzi, separate shower, and dual vanities, creating a private retreat. Additional 3 more bedrooms, one with its own bathroom. And one more bonus on the top floor enjoy your oversized great room down the hallway. Basement is waiting to be finished with 10 ft ceilings, a walk-out double door and regular size windows. 4.4 miles to Metro North and the Village of Pawling. Dover Schools. CT border is just down the road. Full house generator. Original Owners. "90 minutes from Manhattan.Mountain views. Work remotely, escape every weekend."

128 Old Pawling Road, Pawling
$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
$130,000
2 Beds ⋅ 2 Baths ⋅ 1008053 MLS
Welcome to this beautifully maintained 2-bedroom, 2-bath mobile home in a 55+ community in Dover Plains. Renovated approximately 10 years ago and thoughtfully cared for since, this home offers a warm blend of comfort, character, and practical living space. Inside, you'll find an open-concept layout connecting the living room, dining area, and kitchen, creating an easy flow for everyday living and entertaining. The kitchen features updated cabinetry, ample counter space, and charming farmhouse-inspired details that add personality throughout the home. Natural light fills the living spaces, while the spacious primary bedroom and second bedroom provide flexibility for guests, hobbies, or a home office. One of the standout features is the inviting enclosed porch, offering additional living space to enjoy throughout the seasons. The home's décor and finishes create a welcoming atmosphere with a mix of updated amenities and timeless charm. Outside, the property showcases beautifully landscaped grounds with colorful flowers, mature plantings, garden pathways, and peaceful outdoor seating areas. A work bench and storage shed provides extra space for gardening tools, seasonal items, and outdoor equipment. The carefully designed gardens create a picturesque setting for enjoying the outdoors right at home. Located in Dover Plains within the Dover School District, this property offers convenient access to local shopping, dining, parks, and commuter routes such as the train station, while providing a comfortable, low-maintenance lifestyle in a 55+ community.

30 Tally-Ho Drive, Dover Plains
$385,000
2 Beds ⋅ 1 Baths ⋅ 1006396 MLS
Estate property being sold AS, including contents. 5+/-acre parcel of lovely land with meadows, views of rolling hill tops and majestic trees. There is an old growth of grape vines and an orchard with various fruit trees. A truly special piece of property conveniently located to communte to NYC either by car or train. Just the land and improvements alone proof the value of this offering. The winding driveway leads to newly constructed, oversized garage (25'9x26'5) and an existing one bedroom house. The house was built to be energy efficient- a good portion of the living space is built into a hill. There is underground electric to the house, which is 200 amps, as well as a separate 100 amp service in the garage House is in need of significant rehab, or tear down. Could be a great project.

884 Camby Road, Millbrook
$1,250,000
4 Beds ⋅ 4 Baths ⋅ 1001139 MLS
Set on four beautiful acres with sweeping long range views of the foothills and ridges around Litchfield Hills and The Taconic Mountains, this thoughtfully designed contemporary home offers exceptional privacy, tranquility, and quality throughout. Built by the owners for their own use, no expense was spared, with high end materials and meticulous attention to detail. Incredible natural light fills the home, enhanced by oversized windows that capture the surrounding landscape and bring the outdoors in. A gracious front entry welcomes you into the formal living and dining rooms. The living room features a wood-burning fireplace and beautiful views overlooking the backyard and surrounding landscape. The spacious kitchen is designed for both everyday living and entertaining, featuring a large center island, pantry, and sunny eat-in area. The kitchen opens seamlessly to the family room, where oversized windows frame peaceful nature views and fill the space with light. Both rooms open onto a tiered deck overlooking the gardens and distant mountain views, an ideal setting for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. The expansive primary suite offers a true retreat with a spacious en-suite bath, walk-in closet, and separate sitting area. A large laundry room is conveniently located off the kitchen and two car garage, while a half bathroom and private office complete the main level. The second floor includes three additional bedrooms, including one with its own en-suite bath, while the remaining two bedrooms share a full bathroom. The lower level offers tremendous flexibility and is currently used as workspace. With large windows and direct exterior access, it presents endless possibilities for future finishing as recreation space, studio, gym, media room, or guest area. A newly built two-story barn is a standout addition to the property, featuring durable Hardie Board siding and superior construction quality. Beautifully landscaped and private, this property offers a rare combination of craftsmanship, comfort, and natural beauty. This property is located in an area of the Hudson Valley known for its scenic beauty, and farm to table restaurants. Less than ten minutes to Metro North Railroad.

110 Hillside Avenue, Wingdale
$5,000,000
995039 MLS
Nestled in the heart of the Town of Washington’s breathtaking countryside, this extraordinary 332+ acre property offers a rare opportunity to own an expansive and remarkably diverse landscape in the scenic Harlem Valley. A stunning blend of rolling hay fields, open pastures, mature hardwood forests, three peaceful ponds, and a meandering stream, the land unfolds with incredible natural beauty in every direction. Rising steadily from east to west, the property reaches elevations of approximately 1,175 feet, where vast level areas capture commanding panoramic views stretching across the Harlem Valley. With numerous potential homesites positioned throughout the acreage, each offering its own spectacular vantage point, the possibilities are endless for creating a private estate, compound, working farm, equestrian retreat, or recreational paradise. The combination of open meadows and wooded terrain, along with an extensive network of trails, provides exceptional opportunities for hiking, horseback riding, ATV use, hunting, wildlife observation, and year-round outdoor enjoyment, all with a remarkable sense of privacy and seclusion. The land is exceptionally well suited for organic farming, livestock, and horses, with fertile fields and varied topography that make the property both functional and picturesque. An existing agricultural tax exemption adds tremendous value, currently reducing taxes from $91,728 to $54,001 annually, a savings of $37,727 per year. For those seeking an even larger landholding, an adjacent 109.69 acre parcel is also available, bringing the combined acreage to an impressive 441.99 acres. This neighboring former dairy farm includes four separate lots consisting of an 88.46 acre parcel previously used for cattle, a 10.37 acre parcel featuring two homes, iconic red barns, and a silo, a 9.82 acre hayfield, and an additional 1.04 acre parcel. A property of this scale, beauty, and versatility is truly a once-in-a-generation offering. Don’t miss the opportunity to own this remarkable piece of countryside paradise with unmatched views, endless potential, and extraordinary natural surroundings. Be sure to click on the virtual tour icon to experience the stunning 360-degree panoramic views from multiple locations throughout this incredible property.

1297 Route 343, Dover Plains
$89,999
3 Beds ⋅ 2 Baths ⋅ 1000972 MLS
Spacious 3-Bed, 2-Bath Double-Wide on Premium Corner Lot in Dover Plains Welcome to this large and bright 3-bedroom, 2-full-bath double-wide home, beautifully situated on a meticulously landscaped corner lot. Offering a wonderful blend of private outdoor space and community perks, this property boasts a lush, thick green lawn and a fantastic rear covered deck that is absolutely perfect for relaxing or entertaining guests. Best of all, you are located just steps away from the community clubhouse and the pool, giving you effortless access to amenities right outside your door. This home is an incredible opportunity to bring your personal style and build quick equity. While it needs some cosmetic updates, the high-ticket structural and mechanical work has already been done for you. You will enjoy massive savings on your utility bills and year-round comfort thanks to premium upgrades, including full spray-foam insulation throughout the entire underbelly, an updated furnace, and central air conditioning. The monthly HOA fee of $510 covers your water, sewer, trash removal, snow removal, common area maintenance, mailboxes, and full access to the pool and clubhouse. Please note that park approval is required for all buyers, and there is a $250 application fee. With the major mechanicals already taken care of, this home is the perfect canvas to make your own—schedule your viewing today!

160 Holesapple Road Unit #52, Dover Plains
$175,000
2 Beds ⋅ 2 Baths ⋅ 997318 MLS
Beautifully maintained and absolutely gorgeous double manufactured home offering spacious open-concept living in the desirable Tally Ho 55+ community. This home features a large living room with a cozy electric fireplace and a gourmet kitchen loaded with extras, including refrigerator, dishwasher, microwave, propane stove, abundant cabinetry, and a breakfast island perfect for casual dining and entertaining. The dining area offers additional custom built-in cabinetry with faux granite countertops and its own electric fireplace, creating a warm and inviting atmosphere throughout the home. A separate laundry room with washer/dryer hookups includes a rear entrance leading to a small stairway, landscaped yard, and paved driveway. The spacious primary bedroom offers excellent closet space and an elevated electric fireplace for added comfort. The primary bath features a tub/shower combination and high countertops. The second bedroom includes its own bathroom with a corner shower featuring a rain-style shower head, faux granite countertop, and high vanity. Additional highlights include central air conditioning, full-house generator, and a 10x10 storage shed. Conveniently located just minutes from the Metro-North train station, the Harlem Valley Rail Trail, shopping, and restaurants, with the mall only 20 minutes away. Tally Ho is a wonderful 55+ community offering an active lifestyle with an on-site clubhouse featuring scheduled activities, lounge area with big-screen TV, pool table, seasonal outdoor swimming pool, and BBQ area.

110 Gina Drive, 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
$699,000
3 Beds ⋅ 4 Baths ⋅ 991179 MLS
A One-of-a-Kind Custom Ranch on Nearly 4 Private Acres. Discover exceptional space, quality, and versatility in this expansive custom-built 3+ bedroom ranch, perfectly tucked away in a serene country setting. Designed for comfort and flexibility, this home is ideal for extended family living, multi-generational needs, or a spacious mother-daughter layout. The main floor offers true single-level convenience with 3 bedrooms and 2.5 baths. A chef’s kitchen anchors the home, featuring abundant cabinetry, granite countertops, a range and a wall oven for large gatherings and a sunny breakfast nook. A dedicated main-level laundry room sits just off the kitchen for added ease. Entertain in style in the formal dining room or relax in the stunning living room with vaulted ceilings, skylights, and a stone fireplace. Oversized sliding doors in both rooms flood the space with natural light and open to a large deck overlooking the property. The primary suite includes an ensuite bath, walk-in closet, and its own brand-new private deck with sweeping views of the fenced backyard. Two additional bedrooms and a full hall bath complete the main level. The full, Finished walk-out Lower Level offers exceptional flexibility and includes a large great room with wet bar and cabinetry. Three additional rooms perfect for guest space, office, gym, or hobbies and a full bath as well as a second laundry area. There is also a spacious utility/storage room. This level functions beautifully for extended family or perhaps a mother/daughter. A large portion of the level backyard is fully fenced—ideal for pets, play, or gardening. The home also includes a two-car attached garage and sits at the end of a private driveway, offering peace and privacy while still being under 10 minutes to the Village of Pawling and the train station. This truly unique property blends quality construction, thoughtful design, and an unbeatable setting. You’ll fall in love with this one-of-a-kind home.

921 W Dover Road, Pawling
$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
$199,000
976107 MLS
Just north of the Town of Pawling border, you will find this 2.4 acre parcel. Convenient location is close to schools, town library, Thomas Boyce Park, Wingdale Metro-North train station. This is a residential parcel, zoned RU.

Route 22, Wingdale
$45,000
971928 MLS
This 0.64-acre parcel on Aldrich Road in Wingdale, NY is offered at $45,000. This property presents a unique opportunity for an investor or a visionary builder looking to create a custom residence in a quiet, rural setting. Property Highlights Acreage: 0.64 acres of land in a serene, off-the-beaten-path location. Price: Competitive entry-point pricing at $45,000, reflecting the current approval status. Status: The parcel is not currently Board of Health (BOH) approved. Buyers will need to conduct their own due diligence regarding well and septic requirements to secure future building permits. Privacy: Located on Aldrich Road, known for its peaceful atmosphere and proximity to natural landscapes. Local Amenities & Lifestyle Wingdale offers a perfect balance of country living and essential convenience: Commuter Friendly: Close to the Wingdale Metro-North station, providing a direct link for those traveling to New York City or lower Westchester. Outdoor Recreation: Enjoy easy access to the Appalachian Trail and nearby trout streams for hiking and fishing. Community: Residents describe the area as a tight-knit, friendly community that takes pride in local holiday traditions and a quiet environment. Schools: Served by the Dover Union Free School District, which locals highly value for its community-focused upbringing. This property is ideal for someone looking to secure a piece of the Hudson Valley at an affordable price and take the next steps toward development.

Aldrich Road, Wingdale
$375,000
3 Beds ⋅ 1 Baths ⋅ 960070 MLS
Located on 1.54 acres of scenic land, this charming overbuilt home has a perfect blend of comfort, privacy, and natural beauty. Enjoy open field views across the street from your living room, creating a peaceful backdrop for everyday living and relaxing evenings. The home features a warm and inviting layout, in the living room and kitchen, walls are tongue and groove knotty pine from ceiling to floor, brick fireplace in living room will keep the house cozy day/night. Retro knotty-pine cabinets from Crown Kitchen Cabinet Corporation (Brooklyn, NY) with a Tracy spacious stainless steel sink. Park your car (electric garage door) and walk through basement to upstairs, basement also has Bilco doors. Potential for wine cellar in pantry/cold room, have a project you would like to work on.....additional heating is already in basement. There is a separate well that can be used for gardening. Each room has original cast iron baseboards, keeping house warm in winter months. Surrounded by open space and mature landscape (grape vine can be found in the backyard) the property provides ample room for outdoor enjoyment, gardening, or future expansion. Minutes from Wingdale Metro North Station. Whether you’re seeking a serene retreat or a place to call home year-round, this property delivers space, views, and timeless appeal in a picturesque setting.

113 Dog Tail Corners Road, Wingdale
$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
$205,000
H6290984 MLS
Located on Route 22 in the town of Dover Plains, this Eight-acre site consists of four lots: 1.66-acre(lot 1), 1.85-acre(lot 2), 2.03-acre(lot 3), and 2.5-acre(lot 4) development sites. It is currently being re-zoned to Gateway Commercial (GC) by the municipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office, light retail, and residential uses. The property was previously BOH-approved for Four, four-bedroom residences along with site plans. The site is an open meadow with high visibility, a daily traffic count of 6924 vehicles a day, and less than one mile from the Dover Plains Metro North Train Station. Purchase one or more for your development needs. The town is looking to increase the growth of its commercial districts; take advantage of this excellent opportunity to join in its efforts while creating a profitable investment.

Route 22, Dover Plains
$195,000
H6290986 MLS
Located on Route 22 in the town of Dover Plains, this Eight-acre site consists of four lots: 1.66-acre(lot 1), 1.85-acre(lot 2), 2.03-acre(lot 3), and 2.5-acre(lot 4) development sites. It is currently being re-zoned to Gateway Commercial (GC) by the municipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office, light retail, and residential uses. The property was previously BOH-approved for Four, four-bedroom residences along with site plans. The site is an open meadow with high visibility, a daily traffic count of 6924 vehicles a day, and less than one mile from the Dover Plains Metro North Train Station. Purchase one or more for your development needs. The town is looking to increase the growth of its commercial districts; take advantage of this excellent opportunity to join in its efforts while creating a profitable investment.

Route 22, Dover Plains
$190,000
H6290988 MLS
Located on Route 22 in the town of Dover Plains, this Eight-acre site consists of four lots: 1.66-acre(lot 1), 1.85-acre(lot 2), 2.03-acre(lot 3), and 2.5-acre(lot 4) development sites. It is currently being re-zoned to Gateway Commercial (GC) by the municipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office, light retail, and residential uses. The property was previously BOH-approved for Four, four-bedroom residences along with site plans. The site is an open meadow with high visibility, a daily traffic count of 6924 vehicles a day, and less than one mile from the Dover Plains Metro North Train Station. Purchase one or more for your development needs. The town is looking to increase the growth of its commercial districts; take advantage of this excellent opportunity to join in its efforts while creating a profitable investment.

Route 22, Dover Plains
board logo

© 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.