Dover Plains Real Estate

Welcome to Dover Plains, a charming gem nestled in the heart of Dutchess County, New York. This picturesque town offers a delightful blend of rural tranquility and modern conveniences, making it a perfect haven for families, retirees, and anyone seeking a serene lifestyle. With its rich history and vibrant community, Dover Plains invites you to explore its unique character.

Dover Plains is known for its stunning natural beauty, dotted with lush landscapes and scenic views that change with the seasons. The town is surrounded by rolling hills and picturesque farmlands, providing ample opportunities for outdoor enthusiasts to hike, bike, or simply enjoy the fresh air. The nearby Appalachian Trail and various local parks offer a plethora of recreational activities for nature lovers.

The town's historic charm is evident in its quaint downtown area, where you'll find a delightful mix of local shops, cozy cafes, and friendly eateries. The community is tight-knit, hosting various events throughout the year that bring neighbors together, fostering a sense of belonging and camaraderie.

Education is a cornerstone of Dover Plains, with access to quality schools that prioritize student growth and development. Families can feel confident in the educational opportunities available to their children.

Conveniently located near major highways and the Metro-North Railroad, Dover Plains provides easy access to nearby cities such as Poughkeepsie and New York City, making it an ideal spot for commuters who wish to escape the hustle and bustle while still enjoying the conveniences of urban living.

Come discover the charm and warmth of Dover Plains, where community spirit and natural beauty create a perfect place to call home!

Newest Listings in 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

$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

$110,000

1021316 MLS

Located approximately 6.5 miles from the Village of Millbrook on a private road off Cart Road. Trains to New York City are available only 3.3 miles away at the Metro North Station in Dover Plains. Picturesque Stone Church Brook traverses the property. Ideal for your weekend or year-round dream home. BOHA and Road Maintenance Agreement on file.

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

$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

$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

$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

$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

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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.