Dover Real Estate

Welcome to Dover, NY – a picturesque town nestled in the heart of Dutchess County, renowned for its charming small-town atmosphere and vibrant community spirit. One of the standout features of this lovely area is its exceptional school district, which plays a crucial role in attracting families to the region.

The Dover Union Free School District is dedicated to providing a high-quality education that nurtures both academic excellence and personal growth. With a strong commitment to fostering a supportive learning environment, the district prides itself on its dedicated educators who inspire students to reach their full potential. The schools in Dover are equipped with modern facilities and resources, ensuring that students have access to the tools they need to succeed.

Parents will appreciate the district's emphasis on a well-rounded education, which includes a variety of extracurricular activities, from sports to arts programs. These opportunities not only enhance students’ educational experiences but also help them develop essential life skills such as teamwork, leadership, and creativity.

Dover's scenic surroundings provide an ideal backdrop for outdoor activities, further enriching the lives of students and families alike. With a strong sense of community and a commitment to excellence, the Dover school district is a cornerstone of this charming town, making it a wonderful place to call home.

Whether you're considering moving to the area or simply exploring your options, you'll find that Dover offers not just a place to live, but a vibrant community where education and family values thrive. Come and discover the magic of Dover, where your dreams of a perfect home and a bright future can become a reality!

Newest Listings in Dover

$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

$680,000

3 Beds ⋅ 2 Baths ⋅ 1047398 MLS

A little bit of magic lives at 16 Carlson Road. Built in 1850, this charming home feels like something out of a fairytale, surrounded by nearly nine acres of mature gardens and old-growth trees. Walking paths wind through the acreage, and the beautifully established landscape gives the property a character all its own. While the history of the home is felt throughout, recent thoughtful updates have been made, creating comfortable, beautifully considered spaces while preserving the character that makes it so special. Inside, natural light fills the rooms, with skylights overhead and windows framing views of the surrounding gardens. The main level unfolds through a series of inviting spaces, including a sunroom, formal and informal dining rooms, and a living room anchored by a wood-burning stove. A deck just off the dining room sits beneath an extraordinary mature hydrangea, creating a natural canopy for long summer lunches and dinners outside. The primary suite is on the main level, with radiant floor heating extending through both the bedroom and spacious bathroom. Two generously sized walk-in closets provide ample storage, while French doors open directly onto a bluestone patio. Just off the bedroom, a charming home office with built-ins makes working from home feel decidedly less like work. Upstairs, two sun-filled bedrooms share a bathroom with a clawfoot tub, with ample storage throughout. The property also includes two outbuildings: a one-car garage and a separate garage/workshop with a loft above, ready for projects, studio space, or whatever creative pursuits the property inspires. Just five minutes from the Harlem Valley Metro-North station, the property offers easy access to New York City, with Grand Central just over two hours away. Wassaic Metro-North is 20 minutes away, with Kent, Connecticut just 10 minutes away and Millbrook approximately 25 minutes. It’s a rare kind of Hudson Valley retreat, where beautiful gardens, a sense of history, and just a little everyday magic come together.

16 Carlson Road, Wingdale

$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

$404,444

2 Beds ⋅ 1 Baths ⋅ 1045289 MLS

WELCOME TO YOUR OWN LITTLE PIECE OF HEAVEN IN SOUGHT AFTER PAWLING NY. PROPERTY HAS TWO SEPARATE LOTS WITH A TOTAL OF 23.50 ACRES AND HAS OUTSTANDING OUTSTANDING MOUNTAIN VIEWS. OWNER HAS NOT TRIED TO SUBDIVIDE, HOWEVER THERE ARE TWO WELLS ON PROPERTY. THERE IS A NEWLY CONSTRUCTED DECK OFF THE KITCHEN. LIVING ROOM HAS A PELLET STOVE WHICH WAS INSTALLED IN 2020 AND KEEPS THE WHOLE HOUSE WARM AND COZY!! HOME HAS AN UNFINISHED BASEMENT WITH RECENT BLOWN IN INSULATION INSTALLED. HOME WAS RENOVATED IN 2019 WHICH INCLUDES A NEW FURNACE. IF YOU LOVE NATURE, THIS IS THE PLACE TO BE, YOU WILL NOT BE DISAPPOINTED, COME TAKE A LOOK.

265 Old Pawling Road, Pawling

$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

$499,000

3 Beds ⋅ 3 Baths ⋅ 1043677 MLS

Tastefully updated 3 bedroom, 2.5 bathroom raised ranch with incredible backyard oasis. Ideal for relaxing or entertaining, this home includes an updated kitchen w/quartz counters & stainless appliances, large living room loaded with natural light and dining room with sliding glass door leading to deck and incredible backyard complete with heated pool & massive patio. Primary bedroom w/ensuite bathroom plus two additional bedrooms and full bathroom on main level. Lower level includes huge family room, laundry room, half bathroom and office/den. New flooring & fresh paint throughout. One car garage for storage. Enjoy the conveniences of 200 amp electric plus a 17kw standby generator. Easy access to local amenities, Wassaic train station, Route 22 and Route 55. Attractively low taxes.

45 Nicole Lane, Wingdale

$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

$585,000

3 Beds ⋅ 3 Baths ⋅ 1036661 MLS

Welcome to this well-maintained 3-bedroom, 2.5-bath Colonial, beautifully situated on over 2 private acres near the Pawling border. Surrounded by mature trees, established gardens, and fruit trees, this property offers a peaceful and picturesque setting with plenty of room to relax, garden, and entertain. The main level features a spacious kitchen, attractive parquet wood flooring throughout much of the first floor, and a cozy wood-burning stove. A standout feature is the first-floor full bath with a Jacuzzi tub and separate shower, along with a convenient powder room for guests. Upstairs, you’ll find three spacious bedrooms and an additional full bath, offering a comfortable and functional layout. The huge unfinished basement is filled with possibilities, featuring large windows and direct egress to the backyard, making it ideal for future recreational, fitness, office, or additional living space. Additional highlights include central air conditioning, a two-car garage, generator hookup, and a water catchment system. With its generous acreage, privacy, mature landscaping, fruit trees, and convenient location near the Pawling border, this inviting Colonial offers space, comfort, thoughtful features, and wonderful potential both inside and out.

36 Hillside Avenue, Wingdale

$575,000

4 Beds ⋅ 3 Baths ⋅ 1036001 MLS

Great Colonial home features a wonderful, 40 ft covered front porch, where you can relax and enjoy the lovely view! Spacious Foyer with closet, large, very nice Living Rm with popular LVP flooring, Family Rm with Fireplace & door to deck. The Kitchen features a spacious Dining Area, an Island with a granite top, stainless appliances, propane range. There is also a formal Dining Rm, currently used as an office. Also on the first floor is a pretty half bath and a laundry area. Upstairs, you will find 4 Bedrooms, one of which is the Primary suite. Hall full bath offers a great vanity with a granite top. All bedrooms have ceiling fans! Large 21x23 Two-Car Garage features a very high ceiling. Basement is 24x40. All dimensions are approximate. Siding, Windows, and Roof 2019. Not far from the home are the Dover Schools, Town Library, Dykeman’s Farm and farm stand. Boyce Park in Wingdale offers a playground, baseball field, basketball court and a pavilion. *Metro-North has two nearby train stations, Wingdale and Pawling. Nature lovers will enjoy hiking the Appalachian Trail and exploring the beautiful area of well-known Stone Church in Dover. Short drive to Pawling, where you will find quaint shops, restaurants & pubs, grocery store, gym, medical offices, more.

125 Sheldon Road, Wingdale

$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

$299,900

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

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