Dover Plains Homes with Detached Parking features

Welcome to Dover Plains, New York – a charming gem nestled in the heart of Dutchess County. Known for its picturesque landscapes and friendly community, Dover Plains offers a perfect blend of rural tranquility and modern conveniences. With its rich history and stunning natural beauty, this quaint town is an ideal place to call home.

Dover Plains is characterized by its welcoming neighborhoods, where you’ll find a variety of homes that cater to diverse lifestyles. One of the standout features of many properties in this area is the availability of detached parking. Whether you have multiple vehicles, enjoy tinkering with your car, or simply value the convenience of extra storage space, homes with detached parking options provide both functionality and ease. This feature not only enhances your living experience but also adds an extra layer of privacy and security.

As you explore Dover Plains, you’ll discover a vibrant community filled with local shops, delightful eateries, and recreational opportunities. The nearby scenic parks and hiking trails invite outdoor enthusiasts to immerse themselves in nature, while the community events foster a strong sense of belonging. With easy access to major highways and public transportation, commuting to nearby cities is a breeze, making Dover Plains an appealing choice for those who work in the bustling metropolitan areas but prefer the serenity of small-town living.

Whether you’re a first-time homebuyer or looking to settle down in a peaceful environment, Dover Plains offers a unique lifestyle with homes that feature the convenience of detached parking. Come discover your dream home in this idyllic town today!

Newest Dover Plains Homes with Detached Parking features

$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

$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

$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

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.