Courtesy: Keller Williams Village Sq Rlt
201-445-4300
Welcome to 24 Walnut Street, Flexibility, Space & Endless Possibility in the Heart of Chester, NY Tucked on a generous half-acre lot in the charming Village of Chester, this versatile 4-bedroom, 2.5-bath home offers a rare mother-daughter layout that delivers the best of both worlds, income potential, or simply more space to grow. Set on a quiet, tree-lined street just minutes from the Orange Heritage Trail, local dining, and easy commuter access, this property is as practical as it is inviting. The main residence spans three spacious bedrooms and 1.5 baths, offering comfortable everyday living with room for the whole family. The private secondary suite features a bright one-bedroom, one-bath layout, ideal for in-laws, extended family, an au pair, or a long-term rental opportunity. Whether you're seeking to offset your mortgage or keep loved ones close while preserving everyone's privacy, this thoughtful configuration checks every box. With a 2,698 sq ft footprint, a full basement, attached garage, hardwood floors, central air, and a sweeping 0.56-acre lot with park views, this home combines classic charm with everyday function. Located in the Chester Union Free School District and just a short drive to Legoland, the Capelli Sports Complex, and Coach USA transit to NYC — 24 Walnut Street isn't just a home. It's a lifestyle. Opportunity like this doesn't last. Schedule your private showing today.
Courtesy: Compass Greater NY, LLC
914-238-0676
Some lots just have good bones. This one has it's own private nature trail, stocked pond rights, and a cul-de-sac that dead-ends into miles of nature trails anchored by a solid, spacious raised ranch on 1.8 acres. Inside, the home has been partially updated and offers solid bones with room to add your own touch over time. The house delivers where it counts. Three bedrooms, two and a half baths, large kitchen, a two-car garage, and a three-season room and deck that make the most of a property this beautiful. The woodburning stove in the basement helps the winter months stay cozy while saving on fuel oil bills. Multiple outbuildings including a shed and a playhouse that will get more use than you'd expect. The lawn and mature landscaping are genuinely impressive — the kind that takes years to establish and shows the moment you pull in the driveway. Then there's everything else. When not playing on the impeccable lawn, the kids could be kids catching frogs and fish, climbing trees and building forts in the woods.. All without leaving the property. When they do, the trail into Goosepond Mountain State Park is just a few doors down, at the end of the Cul de Sac.. The street itself is unhurried and unpretentious — picture dads teaching kids to ride bikes in the road, strollers, joggers, dogs on leashes and kids swarming ice cream trucks. With easy access to amenities and a realistic commute to NYC, Booth Rd means you don't have to choose between the life you want and the job that funds it. Come feel it. The land speaks for itself.
Courtesy: Howard Hanna Rand Realty
845-928-9691
Imagine ending every day watching the sun set from your front porch, with breathtaking views that change beautifully through every season. Sunset views, a fenced backyard, brand-new Trex deck, above-ground pool, home office, and the flexibility of **four sleeping spaces** make this property truly stand out. Perched atop the highly sought-after Fieldcrest subdivision, this stunning Colonial is officially listed as a **three-bedroom home** but offers a **spacious bonus room that provides the perfect opportunity for a fourth sleeping space**. Whether you need an additional bedroom, guest room, nursery, home office, or playroom, this versatile space adapts to your lifestyle. Set on 1.3 beautifully landscaped acres, the home blends comfort, functionality, and exceptional outdoor living. The fenced backyard features a newer oversized Trex deck, an above-ground pool, and plenty of room to relax, entertain, and create lasting memories with family and friends. Inside, sun-filled living spaces showcase hardwood floors, recessed lighting, a striking stone fireplace, and an expansive family room with a pellet stove capable of heating the entire home. The spacious kitchen serves as the heart of the home, complete with granite countertops, abundant cabinetry, stainless steel appliances, double ovens, and direct access to the backyard for seamless indoor-outdoor living. Upstairs, you'll find three generously sized bedrooms along with the versatile bonus room that provides valuable additional living and sleeping flexibility. The primary suite offers a private retreat with a Jacuzzi soaking tub and separate shower, while second-floor laundry adds everyday convenience. A walk-up attic, full basement, newer major systems, and exceptional curb appeal complete this impressive property. Offering the versatility of **three official bedrooms plus a bonus room that functions beautifully as a fourth sleeping space**, this home delivers the space, flexibility, and lifestyle today's buyers are searching for in one of the area's most desirable neighborhoods.
Courtesy: Weichert Realtors
845-782-4646
Welcome to this stunning Colonial, perfectly blending comfort, style, and functionality. Offering 2,370 sq ft plus full walkout basement, this beautifully designed home features 4 spacious bedrooms and 3 full bathrooms, creating an inviting layout ideal for everyday living and entertaining. Step inside to a grand, sun-filled foyer with soaring ceilings that set the tone for the home’s warm and elegant feel. The thoughtfully designed kitchen is perfect for cooking, gathering, and hosting. Outdoors, enjoy your own private retreat with an above-ground pool, play area, and a beautiful, wooded setting. With over 18 acres, the land offers exceptional privacy, natural beauty, and a peaceful buffer around the home. A rare opportunity to own a spacious Colonial with room to live, relax, and entertain—inside and out. Schedule your private showing today!
Courtesy: Keller Williams Realty
845-928-8000
Welcome to the highly sought-after Creamery Estate, located in the award-winning Warwick school district!. This inviting waterfront Colonial-style home offers the perfect blend of comfort, charm, and scenic beauty, set on an acre of beautifully maintained grounds with peaceful views of Creamery Pond. This 3-bedroom, 3 full bath home features hardwood floors throughout and a spacious, easy-flow layout designed for everyday living. The updated kitchen, complete with brand new LG appliances, center island, and a stylish tiled backsplash, opens into a formal dining room—perfect for hosting friends. Enjoy multiple living spaces, including a sun-filled living room and a cozy family room with a fireplace, creating a warm and welcoming atmosphere. A dedicated home office offers the flexibility you need for remote work or a quiet study space. Upstairs, the primary suite is a true retreat, featuring a private full bath with double vanities, a whirlpool tub, and a private balcony overlooking Creamery Pond—the perfect place to start or end your day. Two additional generously sized bedrooms and a full hall bath complete the upper level. The finished basement (not included in square footage) provides even more room to spread out, offering ideal space for a playroom, home gym, or guest area, along with walkout access and egress windows for added convenience. Step outside to your expansive deck and enjoy your private, fenced-in waterfront backyard—perfect for summer barbecues, morning coffee, or simply taking in the peaceful surroundings. Spend your days fishing, kayaking, or relaxing by the water from your own private dock. Conveniently located near schools, the Village of Sugar Loaf, boutique shops, and dining, and just about an hour to NYC. Enjoy easy access to local orchards, wineries, ski areas, the Appalachian Trail, and the Heritage Bike Trail—making this home ideal for both relaxation and year-round recreation. A rare opportunity to own a true waterfront gem!
Courtesy: eXp Realty
888-276-0630
Tucked away on over 3 private acres, this recently renovated custom residence offers a rare blend of seclusion, craftsmanship, and elevated living. Surrounded by hundreds of acres of protected state land, the setting ensures unmatched privacy with direct access to nature, including trails that connect to the Appalachian Trail just beyond your backyard. A natural waterfall adds to the serene landscape, creating a truly one-of-a-kind backdrop. A dramatic entry introduces the home with soaring ceilings and heated marble floors, setting the tone for the refined interiors throughout. The layout flows effortlessly into expansive formal living and dining spaces, ideal for both everyday living and entertaining. At the heart of the home is a thoughtfully designed chef’s kitchen featuring premium appliances, custom stone and tile finishes, a gas range with griddle, double ovens, and an oversized two-tier island with prep sink. A walk-in pantry and elegant butler’s area provide both function and style. The family room is a standout space, offering scale, natural light, and architectural character, making it the perfect gathering area. Designed with entertaining in mind, the outdoor living experience is just as impressive, complete with a full stone kitchen and bar, a spacious stamped concrete patio, and a private hot tub retreat, all surrounded by custom masonry. Upstairs, the primary suite serves as a private sanctuary with its own balcony and spa-inspired bath featuring a soaking tub, custom shower setup with steam capability, and refined finishes throughout. Additional bedrooms are generously sized, offering comfort and flexibility for guests or extended living. The fully finished lower level expands the living space with a recreational area, full gym, and wet bar, perfect for hosting or unwinding. Throughout the home, hardwood flooring, an integrated sound system, and high-efficiency construction with spray foam insulation and multiple heating zones enhance both comfort and performance. Completing the property is a spacious three-car garage, a beautifully maintained yard with room to enjoy, and infrastructure already in place for a future gated entrance. A truly exceptional offering where design, privacy, and lifestyle come together seamlessly.
Courtesy: Ellis Sotheby's Intl Realty
845-353-4250
The Conklin House: A Masterpiece of History & Modern Luxury. Experience the perfect blend of early 20th-century charm and 21st-century comfort. The Conklin House, a classic 1908 Queen Anne Victorian, stands as a commanding presence at the edge of the historic Village of Sugar Loaf. The home has always been used residentially but zoning permits commercial usage as well. Originally ordered from the Sears & Roebuck catalogue and delivered by rail, this "pre-fab" pioneer was famously the first electrified home in the area. The current owner has meticulously performed a full-scale reconstruction, ensuring the home is entirely turn-key while honoring its heritage. The home features modern infrastructure with all-new mechanical systems, walls, and energy-efficient windows. Its preserved character is astounding. Every period molding, the original grand staircase, panel doors and authentic flooring have been salvaged and restored. The architectural heritage is monumental as it features its signature steeply pitched hipped roof and a dominant front-facing gable that defines its Victorian silhouette. Built for Howard Conklin—the local postmaster/general store owner—and later by his son, Dr. Roger Howard Conklin, this residence has been a cornerstone of the community for over a century. It represents a rare opportunity to own a piece of Hudson Valley history without the burden of historic maintenance. The lifestyle in Sugar Loaf and Chester, NY is refreshing, especially to New Yorkers getting away from the city. Nestled in a tight-knit arts and crafts hamlet, one is steps away from 18th-century buildings housing artisan studios, galleries, and boutique eateries. And there is rich Outdoor Adventure to take advantage of too! The area has direct access to the 18-mile Heritage Trail for biking and walking, plus proximity to Goosepond Mountain State Park and the Birnberg Nature Preserve. Its rural serenity offers a quiet, creative lifestyle surrounded by majestic mountains and rolling meadows, all while being part of a bustling weekend destination. Driving to and from the Conklin House to NYC is about 1 hour and 15 minutes and using mass transit a little longer. This is more than a house; it is a storied landmark reimagined for the modern connoisseur. Nothing compares to the character, lifestyle and wilderness that the Conklin House has to offer.
Courtesy: eXp Realty
888-276-0630
Welcome to Chester, NY, a resort-style luxury colonial set on a private 1.1-acre cul-de-sac lot in the Monroe-Woodbury area of Orange County. This custom residence delivers the space, craftsmanship, and lifestyle today's relocation and move-up buyers are searching for, with approximately 4,624 square feet, refined architectural detail, mountain views, and seamless indoor-outdoor living. From the bluestone entry and custom foyer to the arched windows, detailed millwork, and stone fireplace, every major room has been designed to make a statement. The chef's granite kitchen, expansive family room, and finished lower level with theater, gym, and additional recreation space create flexibility for entertaining, working from home, and everyday luxury. Outside, the backyard becomes the headline feature: saltwater in-ground pool, firepit, koi pond, extensive pavers, and a 3-season outdoor kitchen that gives this home true vacation-at-home appeal. For buyers looking for a luxury home in Chester NY, a Hudson Valley estate near NYC, or a Monroe-Woodbury area home with pool, privacy, and commuter convenience, This is the kind of property that sells both a residence and a lifestyle.
Courtesy: Keller Williams Realty
845-928-8000
This beautiful custom home is planned to be built in the highly sought-after Sugar Loaf area, offering the convenience of municipal water and sewer. The main level welcomes you with warm hardwood floors and a kitchen featuring a choice of elegant granite or quartz countertops, a stainless steel appliance package, a center island perfect for meal preparation, and a spacious dining area with a slider that opens to a spacious deck. The cozy family room, complete with a fireplace, creates an ideal spot for gatherings. Also on this level are three comfortable bedrooms, including a primary suite with a bathroom showcasing a double vanity, a relaxing soaking tub, and a tiled shower, along with a stylish main hall bath. The finished lower level offers additional space with an extra bedroom or home office, along with a large recreation or living room—perfect for relaxing or entertaining. Enjoy extra features and the chance to choose custom finishes that make your home uniquely yours. Located conveniently near shopping, charming boutique stores, restaurants, wineries, breweries, apple orchards, lakes, Appalachian trails, and major commuter routes, with just about an hour to reach NYC.
Courtesy: Keller Williams Realty
845-928-8000
3 bedroom 2 bath contemporary home tucked away on a quiet street. Modern renovation already started, put your finishing touches on it. Home sold as is. Open concept living, spacious kitchen, private primary suite on 2nd floor with 2 additional bedrooms on 1st floor. Peaceful setting and still close to all amenities. 1,000 sq ft 2 car detached garage.
Courtesy: North Country Sothebys Int Rlt
914-271-5115
From morning coffee in Bronxville Village to an easy commute into Manhattan, this inviting two-bedroom co-op at the sought-after Vincent Arms Cooperative makes everyday living effortless. Offering generous living spaces and an unbeatable location, it's the perfect place to enjoy all that this vibrant community has to offer. The spacious living room provides an ideal setting for both relaxing and entertaining, with ample room for a dining area. The adjacent kitchen is appointed with granite countertops and stainless steel appliances, while both generously sized bedrooms offer comfortable accommodations and abundant closet space. Perfectly positioned directly across from a neighborhood park featuring a playground, basketball court, and peaceful sitting area, this home also offers exceptional convenience for commuters. Enjoy quick access to the Bronx River Parkway, the Bronxville and Fleetwood Metro-North stations, and the Sarah Lawrence College campus, all just minutes away. Whether you're searching for your first home, looking to simplify your lifestyle, or seeking a home in one of Westchester's most desirable communities, this residence offers the perfect blend of comfort, convenience, and location. Vincent Arms also features a ground-floor laundry room, a live-in superintendent, and the convenience of nearby shops, restaurants, parks, and transportation. Building amenities include a ground-floor laundry room and a live-in superintendent.
Courtesy: Keller Williams Realty
845-928-8000
Beautiful custom new homes to be built in Golden Meadows Estates, offering the rare combination of municipal water and sewer, thoughtfully designed floor plans, and stunning lots in a highly desirable location in the Warwick school district. Homes will start at $780,000, with multiple design options available to suit a variety of lifestyles. Lots 1 and 2 will feature custom Bilonial designs with open-concept living spaces ideal for modern living. Lot 3 will showcase an approximately 3200 sq. ft. colonial offered at $879,900, and Lot 4 will feature a beautiful traditional colonial approx. 3000 sq ft., priced at $869,900. Buyers also have the opportunity to bring their own custom plans and collaborate with the builder to create a home tailored to their vision. Each residence will be crafted with quality finishes and attention to detail throughout. The heart of the home will be a beautifully designed custom kitchen featuring a selection of cabinetry styles, granite or quartz countertops, farmhouse sinks, and a generous $27,000 allowance toward kitchen and bathroom cabinetry and surfaces. These thoughtfully curated options allow buyers to personalize their space while maintaining a high standard of design. Hardwood floors will be installed throughout the home, creating warmth and continuity from room to room, while the bathrooms will feature beautifully selected tile finishes for both style and durability. The spacious family room will serve as a welcoming gathering space, complete with a stunning 36-inch fireplace. The open layout flows seamlessly into a large dining area perfect for hosting holidays and special occasions, along with a comfortable living room designed for everyday relaxation and entertaining. Upstairs, each home will offer four generously sized bedrooms. The primary suite is designed as a private retreat, complete with a spa-inspired bathroom featuring a soaking tub, double vanity, and separate shower—creating a serene space to unwind at the end of the day. Golden Meadows offers exceptional convenience, located just minutes from major highways, shopping centers, apple orchards, wineries, and a wide selection of restaurants. Residents will also enjoy close proximity to the charming boutiques and the Sugar Loaf Performing Arts Center, the scenic Heritage Trail for biking and walking, and the vibrant community atmosphere that makes this area so desirable. This is a rare opportunity to build a new custom home in a prime location while enjoying modern amenities, refined finishes, and the ability to personalize your dream home from the ground up.
Courtesy: Keller Williams Realty
845-928-8000
Beautiful custom new homes to be built in Golden Meadows Estates, offering the rare combination of municipal water and sewer, thoughtfully designed floor plans, and stunning lots in a highly desirable location in the Warwick school district. Homes will start at $780,000, with multiple design options available to suit a variety of lifestyles. Lots 1 and 2 will feature custom Bilonial designs with open-concept living spaces ideal for modern living. Lot 3 will showcase an approximately 3200 sq. ft. colonial offered at $879,900, and Lot 4 will feature a beautiful traditional colonial approx. 3000 sq ft., priced at $869,900. Buyers also have the opportunity to bring their own custom plans and collaborate with the builder to create a home tailored to their vision. Each residence will be crafted with quality finishes and attention to detail throughout. The heart of the home will be a beautifully designed custom kitchen featuring a selection of cabinetry styles, granite or quartz countertops, farmhouse sinks, and a generous $27,000 allowance toward kitchen and bathroom cabinetry and surfaces. These thoughtfully curated options allow buyers to personalize their space while maintaining a high standard of design. Hardwood floors will be installed throughout the home, creating warmth and continuity from room to room, while the bathrooms will feature beautifully selected tile finishes for both style and durability. The spacious family room will serve as a welcoming gathering space, complete with a stunning 36-inch fireplace. The open layout flows seamlessly into a large dining area perfect for hosting holidays and special occasions, along with a comfortable living room designed for everyday relaxation and entertaining. Upstairs, each home will offer four generously sized bedrooms. The primary suite is designed as a private retreat, complete with a spa-inspired bathroom featuring a soaking tub, double vanity, and separate shower—creating a serene space to unwind at the end of the day. Golden Meadows offers exceptional convenience, located just minutes from major highways, shopping centers, apple orchards, wineries, and a wide selection of restaurants. Residents will also enjoy close proximity to the charming boutiques and the Sugar Loaf Performing Arts Center, the scenic Heritage Trail for biking and walking, and the vibrant community atmosphere that makes this area so desirable. This is a rare opportunity to build a new custom home in a prime location while enjoying modern amenities, refined finishes, and the ability to personalize your dream home from the ground up.
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: 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: 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: Keller Williams Hudson Valley
845-639-0300
Welcome to this luxurious 4+1 bedroom condo, perfectly situated in a prime location. Featuring fabulous high-end finishes, a stunning designer kitchen, beautiful views, and immaculate landscaping, this home is unlike anything you’ll see on the market today. This unit features a built up basement for lots of living space and guest room. A true dream home you’ll fall in love with the moment you walk in. P.s. There are floor plans by the images. Please be aware that this is approximate, might not be this exact unit.
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.
