Courtesy: HomeSmart Homes & Estates
845-547-0005
Great new price! Come take a look at this 2 bedroom charmer with additional room offers potential 3+ bedrooms. Larger than it looks - need to see. Discover the timeless charm and surprising spaciousness of this delightful carriage house, set on a property rich with character and possibility. Step inside to a generous living room where a wood burning fireplace, hardwood floors, and a large bay window create a bright, welcoming atmosphere. Wall sconces add a soft glow, and a wall A/C unit ensures comfort throughout the warmer months. The eat in kitchen blends practicality with charm, offering tile floors, a newer refrigerator, a handy island, abundant cabinetry, and a pantry for extra storage. Another bay window brings in natural light and enhances the home’s cozy appeal. A full bathroom with a classic pedestal sink and tub completes the main living space. The primary bedroom features hardwood floors, newer windows, two closets, and its own wall A/C unit. A second bedroom—equally charming—also offers hardwood floors and plenty of natural light. Throughout the home, you’ll find generous storage options, including ample closets and a pull down attic. The property is thoughtfully equipped with a natural gas generator, a paved driveway, and multiple outbuildings that expand its functionality. The main house includes an attached two car garage, while a separate two car detached garage showcases original carriage house doors that add a touch of historic character. A small shed provides additional storage, and an oversized outbuilding—with an 8' garage door, separate electric and gas meter, and gas boiler heat—offers exceptional versatility. Above it sits a caretaker’s apartment, ideal for guests, extended family, or workspace needs. All structures are being sold as is. An additional parcel with a storage barn is also available, offering even more room to grow, store, or create. This property blends charm, practicality, and potential in a way that’s increasingly rare—inviting you to imagine the many ways it can fit your lifestyle.
Courtesy: eRealty Advisors, Inc
914-712-6330
Beautifully spacious Colonial set on 1.8 private acres on Pine Hill Road, offering 3,120 square feet of rustic, updated charm behind a gated entry and surrounded by magnificent grounds. The main level welcomes you with a spacious eat-in kitchen that flows seamlessly into the dining area, creating an ideal setting for everyday living and effortless entertaining. The massively large living room serves as the heart of the home, offering abundant space, a warm fireplace, and a comfortable gathering atmosphere. Upstairs, the serene primary bedroom retreat features a private balcony overlooking the expansive backyard, providing a peaceful place to relax and take in the property’s beautiful surroundings. Additional highlights include a partially finished full basement, central air, alarm system, new generator, and expansive rear deck ideal for entertaining or relaxing. Conveniently located with easy access to Route 17 and shopping, this property offers the perfect blend of privacy, comfort, and convenience.
Courtesy: eXp Realty
888-276-0630
THE ULTIMATE HUDSON VALLEY LEGACY ESTATE 53 ACRES OF UNMATCHED POTENTIAL Rarely does a property emerge that perfectly balances refined luxury living with raw, untapped opportunity. Nestled in the heart of scenic Chester, New York, 20 Goshen Road offers an expansive 53-acre canvas designed for the visionary. Whether you envision a world-class equestrian facility, a high-potential residential development, or a private sustainable sanctuary, this estate delivers on every front. THE RESIDENCE Built in 2002, the custom-designed 3,348 sq. ft. home features 4 spacious bedrooms and 3 full baths. The layout is thoughtfully crafted to maximize natural light and views of the sprawling grounds. The infrastructure is built for the enthusiast, featuring an oversized 3-car garage with 10-foot doors—perfect for car collections, boats, or equipment. THE GROUNDS & EQUESTRIAN APPEAL Step outside into a nature lover’s paradise. The property is crisscrossed with miles of well-maintained horse trails, making it a premier choice for equestrian pursuits. The land is rich with resources, including an estimated $30,000 in marketable timber and a thriving, mature orchard boasting over 40 trees including pear, cherry, apple, and peach varieties. SUSTAINABILITY & UTILITY Embrace a self-sufficient lifestyle with an infrastructure designed for resilience. The property features a large-scale chicken coop with a capacity for up to 200 birds and an incredibly efficient heating system powered by an outdoor wood-burning furnace, significantly reducing utility costs while utilizing the property's natural resources. INVESTMENT & DEVELOPMENT Positioned in one of Orange County’s most investment-friendly regions, the 53.00-acre lot size offers significant subdivision possibilities. Investors and developers will recognize the rare value in the expansive road frontage and the desirable Chester location, just moments from local amenities yet completely secluded. Discover the endless possibilities of 20 Goshen Road—where your private retreat meets a high-yield investment.
Courtesy: Joseph Baratta Company Realty
800-628-3119
A Landmark Farmhouse with a Story to Tell. Standing proudly since 1872, this historic Colonial farmhouse is one of the very first homes built on Black Meadow Road and remains a meaningful piece of Chester’s agricultural past. Once surrounded by hundreds of acres of open farmland and dairy cows, the home still carries the soul of a working farm while offering the comforts of modern living. With over 4,000 square feet of living space, the home blends authenticity with thoughtful updates. Original architectural elements—including wide-plank floors, carefully refinished—add warmth and character throughout. Two staircases provide access to the second floor, reflecting the home’s natural evolution over time. The kitchen is rich in historic detail, highlighted by authentic hand-hewn wood support beams, original to the house and a true testament to 19th-century craftsmanship. Modern enhancements integrate seamlessly, including granite countertops, custom cabinetry, stainless steel appliances, and new high-performance HPL flooring designed for durability. The layout includes six bedrooms and four bathrooms, with twin primary suites located on opposite wings of the home, each offering walk-in closets and a sense of privacy. The welcoming foyer features new hardwood floors, while the spacious mudroom has been updated with new tile flooring and a full bathroom, ideal for everyday country living. A sunken family room with a fireplace creates a cozy gathering space, and the large formal dining room, featuring newly refinished hardwood floors, is perfectly suited for holidays and special occasions. At the rear of the home, a sun-filled sunroom offers a peaceful retreat—ideal for indoor plants, a reading nook, or a creative space that enjoys natural light throughout the day and connects the home to its surrounding landscape. The basement reflects the home’s practical history. While rustic, it once served as a working space where wine was produced beginning in the 1950s, complete with original shelving used for canning and seasonal storage. Outside, raised garden boxes invite you to plant vegetables, herbs, or flowers—continuing the tradition of working the land and enjoying the rewards of homegrown living. Additional features include a two-car garage with upper-level storage and a location that offers the peace of country life with convenience—just one hour from NYC. This is more than a residence—it is a historic home, lovingly maintained, ready to welcome its next chapter.
Courtesy: Karten Real Estate Svcs LLC
917-502-2635
Historic Colonial Era Home in the Heart of Sugar Loaf, NY Located just 60 minutes from NYC Zoned Residential/Commercial Step into history with this one-of-a-kind 1,750 sq. ft. Colonial era home, where 18th-century charm meets 21st-century opportunity — right in the heart of the artisan hamlet of Sugar Loaf, NY. Original building was built in 1770, this unique property features: • One of a kind Colonial era home, featuring original exposed hand-hewn beams, barn siding walls, and a fireplace • Two spacious workshops/studios – ideal for artists, entrepreneurs, or makers – currently a woodcarvers workshop. • A must-see, living piece of history full of soul and story • Stunning view of Sugar Loaf Mountain right out your front door Zoned commercial/residential, this home offers the perfect blend of live-work potential — ideal for a workshop, gallery, studio, or cozy retreat. Just steps away: • 2 popular restaurants • A vibrant performing arts center • Local breweries with live music • Coffee shop/ Roaster & Brunch House • Year-round craft markets & community events Sugar Loaf is a renowned creative hub, and this home is at the very center of it all. Nestled in the heart of Sugar Loaf’s artisan community, this unique home and shop was long owned by cultural mainstay Jarvis Boone — a woodcarver, painter, entertainer, and local luminary whose influence helped shape Sugar Loaf’s identity as an artists’ village back in the mid 1960’s. Boone’s legacy lives on through his son Clay, who apprenticed with his father beginning at age 7. He has carried on the woodcarving tradition as Sugar Loaf’s resident woodcarver for the last 58 years. This property offers more than walls and beams. Full of character and creative potential, this property is perfect for artists, craftsmen, woodworkers or anyone drawn to a vibrant, storied community. It offers a living canvas for makers and dreamers to carry forward a tradition of creativity. Don't miss your chance to own a timeless treasure in one of the Hudson Valley’s most beloved villages.
Courtesy: MS Realty Group USA, Inc
845-367-7470
Welcome to 12 Damian Court, a spacious Colonial set on a quiet cul-de-sac. This well-maintained home offers 5 bedrooms and 4 bathrooms, with four bedrooms on the upper level and one additional bedroom in the finished basement. The main level features generous living and dining areas, perfect for everyday living and entertaining. The finished basement adds excellent flexibility with a second kitchen and additional living space, ideal for an extended family or guests. Enjoy outdoor living with an inground pool and a large, private yard. Complete with a 3-car garage and located in the Monroe-Woodbury School District, this home offers space, comfort, and versatility.
Courtesy: Tuxedo Hudson Realty Corp
845-915-4567
Set atop a gentle hill with sweeping eastern views of Round Hill and Schunnemunk Ridge, this pristine 1860 farmhouse blends preserved historic character with thoughtful modern updates. Originally part of the Sears family dairy pasture, the 3,866 sq ft home has been meticulously maintained and features original wide-plank hardwood floors, a striking hand-carved banister, five fireplaces with original wooden and stone mantles, 10' ceilings, and large sun-filled windows throughout. The main level offers two gracious living rooms, a formal dining room, a dedicated office, and an updated kitchen outfitted with a Wolf range, cherry cabinetry, generous storage, and a walk-in pantry. A dedicated first-floor laundry room adds convenience. Upstairs are four spacious bedrooms and two full bathrooms, including a generous primary suite with a large walk-in closet and a 5-piece ensuite bath. These spaces reflect the thoughtful renovation completed in 2014 by previous owners, which also included a living room extension, upgraded kitchen, and a 1,250 sq ft three-car garage designed to complement the home’s historic profile. The lower level is just as impressive. The dry, clean basement contains a unique wine-tasting room set against the original hand-stacked stone foundation, offering a charming and unexpected entertaining space. The 5-acre property offers level, usable land framed by mature native trees—including two historic Linden trees dating to the late 1800s—and expansive lawn. In 2022, the owners installed an 8,000 sq ft organic vegetable garden complete with deer fencing and a full irrigation system, creating a highly productive and beautiful outdoor space. Additional improvements include new trees and screening, newly added parking, a ground-floor repaint, refinished wood floors, an EV charger (CCS), and the conversion of the former stable into a functional workshop. Three outbuildings expand the estate’s potential for creative, professional, or commercial work. The 3,036 sq ft workshop is fully equipped with 6" concrete floors for heavy machinery, 220V power, propane heat, ventilation systems, a bathroom with independent septic, and a four-bay garage. The 1,300 sq ft former stable has been transformed into another heated workspace with 220V power, a kitchenette, a sink, and large sliding barn doors for easy access. The charming 144 sq ft red barn, believed to predate the house and possibly dating back to the 1700s, features traditional mortise-and-tenon joinery and hand-tooled beams. Today it serves as a functional landscape shed while retaining its historic character. History runs deep on the property. The grounds include the historic Sears Cemetery, an 11-memorial family graveyard with stones predating the home's construction. Among those buried here is Hector Craig, a U.S. Congressman and father-in-law to William Havemeyer, part of a family central to the development of early Washingtonville. A rare opportunity to own a fully modernized historic estate, this property seamlessly merges historic integrity, architectural detail, and contemporary comfort across home, land, and workspaces. One Hour to NYC, Close to All Transportations, Dining, Hiking, Shopping and other Conveniences.
Courtesy: Howard Hanna Rand Realty
845-928-9691
Discover the perfect blend of comfort, convenience, and community in this 2-bedroom, 1-bath end-unit townhouse. Situated in a quiet corner of the neighborhood, this home offers extra privacy and natural light, along with the added benefit of an attached 1-car garage for secure parking and storage. Inside, you'll find a thoughtfully designed layout that maximizes space and livability - ideal for first-time buyers, downsizers, or anyone seeking a low-maintenance lifestyle. But this home is more than just what's inside. Located in a commuter-friendly community, you'll have access to an impressive selection of amenities designed to enhance your daily life: Two (2) sparkling swimming pools perfect for cooling off in the summer; Two (2) tennis courts, plus basketball and handball courts to keep you active; A fully equipped fitness center just steps from your door; Two (2) playgrounds for little ones to enjoy; and two (2) dedicated dog runs - a dream for your furry friends. Whether you're relaxing poolside, getting in a workout, or taking a stroll with your pup, this community truly offers something for everyone.
Beautiful setting with 3.45 cleared and mostly flat acres next to Crossroads store in Chestertown. Manufactured home (year-round) with added porches, 2-car garage, and several outbuildings. Drilled-well, septic system and 200-amp electric panel. 2-designated bedrooms with a 3rd flex room that could be a bedroom or overflow sleeping. less than a minute drive from exit 25 off I87 for easy access. Must see this property to appreciate.
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Chester is located in New York. Chester, New York has a population of 12,477. Chester is more family-centric than the surrounding county with 37.24% of the households containing married families with children. The county average for households married with children is 36.93%.
The median household income in Chester, New York is $120,288. The median household income for the surrounding county is $85,640 compared to the national median of $69,021. The median age of people living in Chester is 39.1 years.
The average high temperature in July is 83.4 degrees, with an average low temperature in January of 16.3 degrees. The average rainfall is approximately 47.1 inches per year, with 39.1 inches of snow per year.
