Dover Plains Homes with Dover School district

Welcome to Dover Plains, a quaint and inviting community nestled in the heart of Dutchess County, New York. Known for its picturesque landscapes and small-town charm, Dover Plains offers a unique blend of rural tranquility and easy access to urban amenities. With its rich history and friendly atmosphere, this delightful town is an ideal place for families and individuals seeking a peaceful lifestyle.

Dover Plains is conveniently located near major highways, making it easy to commute to nearby cities like Poughkeepsie and Beacon, where you can explore vibrant dining, shopping, and cultural experiences. The town is surrounded by lush greenery, providing ample opportunities for outdoor activities such as hiking, fishing, and enjoying the serene beauty of nature.

One of the standout features of Dover Plains is its commitment to education, with homes situated in the highly regarded Dover School District. This district is known for its dedicated educators and strong community support, ensuring that students receive a quality education in a nurturing environment. Families will appreciate the emphasis on academic excellence, as well as the variety of extracurricular activities available to students.

The real estate market in Dover Plains boasts a diverse selection of homes, from charming historic properties to modern family residences. Whether you’re searching for a cozy cottage, a spacious family home, or a serene retreat, you’ll find the perfect fit in this welcoming community. Experience the warmth of Dover Plains, where a sense of belonging and community spirit thrives. Come discover your dream home in this enchanting corner of Dutchess County!

Newest Dover Plains Homes with Dover School district

$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

$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

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

$40,000

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

$130,000

2 Beds ⋅ 2 Baths ⋅ 1008053 MLS

Second chance at 30 Tally-Ho Drive! Back on the market due to buyer circumstances, with no fault to the seller. 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

Start Your Search

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

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.