Welcome to 65 Oxford Springs Road! This stunning 5-bedroom, 3.5-bath Colonial offering approximately 3,400 square feet of thoughtfully designed living space in a peaceful, wooded setting. From the inviting covered front porch, step inside to spacious, light-filled rooms that blend comfort and elegance. Rich hardwood floors, soaring ceilings, abundant windows, and a beautiful stone fireplace create a warm and welcoming atmosphere. The heart of the home is the expansive open kitchen, featuring modern appliances, generous cabinetry, and plenty of counter space, making it ideal for everyday living and entertaining. The kitchen flows seamlessly into the dining and living areas, offering both open gathering spaces and cozy nooks. Five generously sized bedrooms provide flexibility and room for everyone. Enjoy the outdoors from the extensive decks overlooking the mature, wooded surroundings, complete with a charming koi pond that adds to the property's peaceful, natural setting. Whether enjoying morning coffee, entertaining guests, or simply unwinding, this outdoor space offers a tranquil retreat. Adding exceptional versatility, a separate approximately 800-square-foot building offers endless possibilities as an art studio, workshop, private office, creative space, or whatever best suits your needs. With its combination of generous living space, distinctive character, privacy, and flex outbuilding space, this property offers a truly special place to call home.
Welcome to this charming three bedroom, two and a half bath colonial nestled in a welcoming neighborhood just minutes from the highway and the charming hamlet of Sugar Loaf. This inviting home offers a comfortable layout with plenty of space for everyday living and gathering. Outside, enjoy a flat, level yard that provides space for relaxing, entertaining, gardening, or outdoor activities. Conveniently located near shopping, restaurants, and all that the Hudson Valley has to offer, and located in the Warwick School District. A wonderful opportunity to make this colonial your new home! Pictures coming soon!
Welcome to 1 Sanford Avenue, a beautifully designed 4-bedroom, 3-bath Bilonial offering over 2,200 square feet of thoughtfully finished living space in Chester. The inviting exterior features a welcoming entry, attached 2-car garage, and attractive curb appeal. Inside, the open-concept layout is enhanced by soaring high ceilings, hardwood floors throughout, and a tiled foyer. The spacious kitchen features custom cabinetry, granite countertops, and a custom wine rack with wine fridge, creating a stylish and functional space for everyday living and entertaining. The main level includes a bedroom and full bath for added flexibility, while the spacious primary bedroom offers a private ensuite full bath. The lower level provides additional finished living space with plenty of flexibility for a recreation room, home office, gym, media area, or other needs. Additional interior features include surround sound and smart thermostats. The attached 2-car garage includes an EV charger, while the property also features solar panels leased through Sunrun and a backup generator. Additional highlights include spray foam insulation, central air, on-demand hot water, and forced-air propane heating. Located in a desirable Chester setting, this home offers convenient access to shopping, dining, parks, major roadways, and commuter routes, providing a comfortable setting with everyday convenience.
Welcome to this well-maintained raised ranch in Chester, NY, offering 4 bedrooms and 1.5 bathrooms with plenty of space and flexibility. The home features hardwood floors, a bright and inviting layout, and comfortable living spaces throughout. Step outside onto the large deck overlooking a spacious backyard, perfect for outdoor entertaining, recreation, or simply enjoying the outdoors. Conveniently located close to shopping, dining, and major highways, this home offers a great combination of space, comfort, and accessibility. Don't miss the opportunity to make it yours!
Welcome to 34 Boville Court, a stunning, fully updated farmhouse colonial tucked away on a peaceful cul-de-sac and set on just shy of two acres. Thoughtfully designed with timeless style and modern functionality, this completely move-in-ready home offers an exceptional blend of space, comfort, and sophistication. Step inside to beautiful hardwood floors and a bright, inviting layout made for both everyday living and effortless entertaining. The beautifully updated kitchen is complemented by a butler’s pantry, offering additional storage and prep space while making hosting a breeze. Spacious living and gathering areas flow seamlessly throughout the home, creating the perfect setting for everything from intimate nights in to large celebrations. Upstairs, retreat to the impressive primary suite, along with generously sized additional bedrooms featuring beautiful cathedral ceilings that add character and an airy, elevated feel. The fully finished walk-out basement provides an entire additional level of versatile living and entertaining space, with direct access to the expansive property beyond. Set on nearly two private acres, there is plenty of room to relax, entertain, play, and enjoy the outdoors. Situated on a cul-de-sac, with gorgeous updates, a spacious floor plan, and picture-perfect farmhouse appeal, 34 Boville court is truly turnkey and ready to welcome its next owners home.
Welcome Home to 63 Hubshop! This charming colonial boasts 2,100 square feet, 4 Bedrooms, 3 Bathrooms and sits on just under an acre of land. With a spacious kitchen, and both a designated living room and dining room, this home offers an easy-flowing layout, making you feel right at home the moment you walk through the door. Off the kitchen you will find a bonus room that can be transformed into a gym, playroom for the kids, entertainment room for guests or whatever your needs may be. Upstairs, you’ll find four generously sized bedrooms, including a primary suite with its own full bathroom. Last but certainly not least, is the tranquility and calmness this property has to offer. As you venture outside, you will find yourself tucked away on a quiet road with an inviting backyard that has access to Cromline Creek! This offers the perfect setting for those early morning coffees or long days of entertainment . Add easy highway access, an easy commute to NYC, and proximity to shopping destinations like Woodbury Commons, and you've found a location that truly checks all the boxes. Schedule your showing today and make this beautiful home yours before the new school year begins!
COLOR AT THE CURB. A POP OF PERSONALITY AT THE DOOR. FROM THE FIRST HELLO, THIS ONE FEELS LIKE HOME. Before you even step inside, this home makes a memorable first impression. The perennial garden, natural stone walkway, and inviting front door adds just the right pop of color and personality, setting the tone for a home that feels fresh, welcoming and anything but cookie-cutter. Tucked away on a private cul-de-sac shared by just two other homes, this seven-year-young Contemporary, Raised Ranch proves you don’t have to choose between privacy and convenience. Built in 2019 and beautifully maintained, this 3-bedroom, 2-bath home pairs modern finishes with an easygoing, move-in-ready layout designed for the way you actually live. Upstairs, beautiful hardwood flooring flows throughout the home, while cathedral ceilings bring an airy sense of volume to the open living, dining and kitchen spaces. The kitchen brings plenty of personality of its own with rich espresso shaker-style cabinetry, granite countertops and island, a decorative metal tile backsplash and a hammered copper farmhouse apron sink, complemented by stainless steel appliances. Sliding glass doors extend everyday living onto the deck overlooking the level, partially fenced backyard because weekend lounging, al fresco dinners and evenings under the stars are simply better outdoors. The primary bedroom with en-suite bath offers its own private retreat, complete with a dual vanity and walk-in shower. Two additional bedrooms and a second full bath complete the main level. Downstairs, the finished laundry/flex space is ready to work however you need it… home office, gym, storage or hobby space while direct hallway access to the oversized garage keeps everyday life convenient. And about that garage: car enthusiasts, hobbyists and serious storage seekers, take note. Two garage bays include one extended bay with room to accommodate a third vehicle or substantial bonus storage, plus a utility sink for added practicality. Outside, a romantic, cottage-style botanical landscape creates a colorful, ever-changing welcome out front, with established flowering perennials, ornamental grasses, mature shrubs and natural stone coming together in a free-flowing tapestry of color, texture and greenery while the backyard vegetable garden is ready for your own farm-to-table harvest. Gardeners, this one may have your name on it. Set within the Village of Chester with municipal services, natural gas and central air, you’re minutes to major highways, NYC bus transportation, shopping and everyday amenities yet tucked away enough to leave the hustle behind. Young. Modern. Welcoming. Private without feeling remote. And refreshingly free of a renovation to-do list. The door brings the personality. The rest makes you want to stay.
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. 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 a cultural mainstay — 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. 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.
20 Mountainside Drive, Chester, NY offers a spacious Colonial-style single-family home on approximately 1.6 acres with 4 bedrooms, 2 full baths, 2 half baths, 10 total rooms, and approximately 3,080 sq. ft. of above-ground living space. Built in 2021, this Chester residence features central cooling, gas heat, a full basement, fireplace, covered porch, patio, and Attached garage. Located in Orange County within the Chester School District, this home offers space, privacy, and convenient access to shopping, dining, parks, recreation, commuter routes, and Hudson Valley attractions. Some listing photographs have been virtually decluttered and/or virtually staged for visualization purposes. Virtual furnishings shown are not included with the property. Come make it your own.
This well-maintained 4-bedroom, 2.5-bath home on 3 private acres is anchored by an expansive 3-tier Trex deck system and an on ground pool with 8-foot deep end, complemented by a sun deck and pool-surround walkway. The 2,516 square-foot home features 9-foot ceilings with wood molding, with hardwood floors and tile throughout the main floor. The main floor flows from a welcoming foyer through the kitchen and family room, with a separate living room and formal dining room, plus laundry and a half bath. Upstairs, four bedrooms and two full baths provide ample space. The basement offers generous storage, and the 2-car garage completes the layout with a spacious driveway for multiple vehicles. The property is move-in ready with significant recent upgrades: oil furnace replaced October 2020, central air replaced June 2022, and a whole-house filter and water softener system installed April 2024. Propane gas serves the kitchen and dryer, while the fireplace has been converted to propane for convenience but retains the option to revert to wood burning. The home features a sub-panel electric system with manual transfer switch for seamless generator backup in the event of power outages. Located in a quiet Chester cul-de-sac with mountain and woodland views, the home is perfectly positioned for both primary residence and weekend getaway living. Just steps from the Heritage Trail system for outdoor recreation, and only minutes from Legoland, shopping, dining, and all area conveniences.
Welcome to 8 Bridle Lane, Chester, NY, located in the desirable Surrey Meadows neighborhood. Lovingly owned by just one family, this well-maintained 4-bedroom, 1.5-bath has been beautifully cared for and is truly move-in ready. Inside, you'll find beautiful hardwood floors, a comfortable floor plan, and tastefully updated kitchen and baths that blend timeless style with everyday functionality. Pride of ownership is evident throughout, making this a home you can enjoy from day one. Step outside to a fabulous level backyard featuring a super spacious deck, perfect for entertaining, relaxing, or enjoying outdoor gatherings. Additional highlights include an attached garage, generator, natural gas, and municipal water and sewer for added convenience and peace of mind. Ideally located just minutes from shopping, restaurants, schools, parks, and major commuter routes, this home offers easy access to everything that makes Chester and Orange County such wonderful places to call home. If you're searching for a move-in ready 4-bedroom home in Chester, NY with modern updates, a great yard, and an outstanding location, 8 Bridle Lane is ready to welcome you home.
Imagine coming home to your own private retreat, nestled on over 2 beautiful acres in the heart of the Hudson Valley. This stunning home offers the perfect blend of comfort, style, and tranquility, creating an oasis both inside and out. Step inside to a sun-drenched living room featuring soaring cathedral ceilings and a dramatic wall of windows that fills the space with natural light. The spacious dining area flows seamlessly into the heart of the home, a beautifully renovated kitchen designed to impress. Showcasing crisp white cabinetry, quartz countertops, a large farmhouse sink, stainless steel appliances, behind barn doors a large pantry and a stunning center island, this kitchen is perfect for both everyday living and entertaining. Enjoy casual meals in the bright breakfast area, which opens to a generously sized deck overlooking the peaceful backyard an ideal setting for morning coffee, outdoor dining, or simply relaxing in nature. Gleaming hardwood floors and recessed lighting add warmth and elegance throughout the main level. The spacious primary suite offers cathedral ceilings, two large closets, and plenty of room for a king-sized bed. Two additional generously sized bedrooms and a full bathroom complete the main level. Downstairs, you'll find a welcoming tiled family room with direct access to the porch and backyard, making indoor-outdoor living effortless. A versatile bonus room provides endless possibilities as a home office, gym, playroom, or guest space. The lower level also features a newly renovated full bathroom and a private laundry room. Outside, the expansive property is a true sanctuary, complete with an above-ground pool, playground, and plenty of open space to enjoy recreation, gardening, or peaceful evenings under the stars. Conveniently located for commuters and just minutes from the Hudson Valley's renowned wineries, breweries, restaurants, shopping, and outdoor recreation, this exceptional home offers the lifestyle you've been searching for. Come experience all the beauty and charm the Hudson Valley has to offer you'll be ready to call this one home.
Welcome to this impeccably maintained raised ranch in the highly sought-after Surrey Meadows Community. Upon entering the foyer, you'll find a practical area beneath the stairs, providing convenient storage for coats and shoes. The lower level features a spacious bedroom with access to a full bathroom, complemented by a versatile bonus room perfect for a cozy den or guest accommodation. Ascend the hardwood stairs to the living room, which boasts hardwood flooring and abundant natural light. This level also includes two generously sized bedrooms and an additional bonus room, ideal for a home office. Newly installed pocket doors maximize space. The fully renovated kitchen is a culinary enthusiast's dream, featuring hidden spice cabinets, a copper farmhouse sink, and a glass-door pantry. From the kitchen, step out onto the deck that overlooks a substantial yard. The home includes a convenient garage and a shed, ideal for storage or lawn equipment. Enjoy year-round activities such as Legoland Resort, artisanal eateries and wineries, orchards, and Orange County's recreational lakes. Within walking distance to both the Middle School and High School and approximately an hour's drive from New York City, with public transportation to NYC nearby. This residence is truly a must-see.
Step into the timeless charm of this historic 1800s farmhouse, where character and history come together in a warm, inviting setting. Original details, classic craftsmanship, and the unique character of a bygone era create a home unlike today’s new construction. Adding to its rich history, the original deed to the property is included and will be conveyed to the new owner—a rare keepsake that reflects the home’s remarkable past. As is typical of homes built during this period, some ceilings, doorways, and stairwells are lower than modern standards, enhancing the home’s authentic historic appeal. If you’ve been searching for a property with personality, charm, and a story to tell, this unique home is ready for its next chapter.
Welcome to 70 Main Street, a village gem situated right in the heart of historic Chester! This versatile 4-bedroom, 2.5-bathroom home combines classic architectural character with generous living spaces and modern convenience. The main residence features an inviting floor plan with bright, sunlit rooms and comfortable living areas throughout. A standout highlight of this property is the separate detached barn/garage, featuring a private loft perfect for an artist studio, or a dedicated work-from-home space. Enjoy classic Village of Chester living with walkable access to schools, local dining, boutique shopping, parks, and effortless commuter routes. A rare find offering space and charm.
Welcome to this comfortable 3-bedroom, 3-bathroom, end unit condo with a 2-car garage in the Whispering Hills community of Chester, NY. It’s the kind of place that feels easy the moment you walk in—spacious enough for everyday living, yet low-maintenance so you can actually enjoy your free time. Whispering Hills is one of those communities that just works. Residents get access to two outdoor pools, tennis and basketball courts, a clubhouse with a gym, playgrounds, walking paths, and even a dog run. HOA covers the lawn care, snow removal, and trash, so weekends stay yours. Location is a big plus. You’re just minutes from ShopRite, local restaurants, and everyday shopping in the Village of Chester. Castle Fun Center is right nearby for family outings, and LEGOLAND New York is a short drive away in Goshen. The Heritage Trail is close for walking or biking, and you’re surrounded by Hudson Valley favorites—apple orchards, wineries, and plenty of outdoor spots when you want to get out. Commuters will appreciate the Short Line/Coach bus stop right in the complex for an easy ride into the city, plus quick access to Route 17 and the Thruway. You’re also not far from Woodbury Common for outlet shopping when the mood strikes. This is a solid, practical home in a well-kept community with real conveniences close by. Come take a look and see if it feels like the right fit.
Highly sought-after Warwick Schools, this Colonial offers curb appeal with custom stone entrance pillars featuring illuminated house numbers, an inlaid driveway address, professionally landscaped grounds accented by natural stone and in-ground lighting, and an insulated two-car carriage-style garage with glass doors. A grand two-story foyer with soaring ceilings, elegant wainscoting, and abundant natural light. The dramatic two-story living room showcases vaulted ceilings, a fireplace, and expansive windows with Sugar Loaf Mountain views. The spacious kitchen features stainless steel appliances, a center island, built-in wine cooler, and a bright eat-in dining area with access to the rear deck. Generously sized family, formal, and dining rooms provide the perfect setting for everyday living and entertaining. The primary suite offers a walk-in closet, dressing area, whirlpool soaking tub, and separate walk-in shower. Three additional spacious bedrooms, a finished basement with a bonus room ideal for a pantry, or additional storage. Minutes from wineries, farms, Woodbury Outlets, Metro-North, major highways, and more.
Welcome to Whispering Hills! Discover easy living, comfort and privacy while living within a neighborhood community. Perfect for first time home buyers or if you're downsizing for care free, low maintenance living. Enjoy this spacious 3 bedroom, 3 bath townhouse with lots of storage and your private garage with direct entry into your home. Comfortable and spacious bedroom layouts with baths and ample closet space throughout. Cozy up with your living room fireplace anytime you want to relax. Enjoy morning coffee on your patio directly off the kitchen. This very bright end unit offers extra windows and a large open yard area that affords much outdoor space for your enjoyment. Home features a newer air conditioning conditioner and double patio slider. Location is perfect for commuters and convenient to all major shopping, restaurants and entertainment. The complex offers access to amenities that everyone can enjoy: swimming, handball, tennis, basketball and dog runs too. No need for gym memberships as you have a fully equipped fitness center. Quick access to Route 17 and 94 centered between NYS Thruway and Route 84. Minutes to Legoland, Woodbury Common Outlets, Chester, Sugar Loaf , Warwick and the Heritage Trail. Don't miss this quiet and private inside home off the main road!
Welcome to 66 Whitetail Run – Chester, NY. Tucked back from the road on an ample, tree-lined lot, this charming contemporary colonial offers the perfect blend of privacy and convenience in the Monroe-Woodbury school district. Surrounded by nature and filled with birdsong, this peaceful setting feels like a retreat while still being close to all local amenities. Step inside to a bright, open living room featuring soaring ceilings, a wood-burning fireplace, and oversized windows that flood the space with natural light. Hard floors flow throughout the main level, leading to a spacious eat-in kitchen with granite countertops, plus a formal dining room perfect for hosting gatherings and special occasions. This 3-bedroom, 1.5-bath home also offers both bathrooms newly renovated, along with the convenience of a main-floor laundry room with a new washer and dryer. An attached one-car garage adds everyday practicality, while the back patio invites you to unwind and enjoy the tranquil, wooded surroundings. Don't miss your opportunity to make this move-in ready home yours!
One floor living at it best! Walk out your front door, sit on your rocking chair front porch with your morning coffee & enjoy the mountain views! This 3 bedroom 1 bath ranch offers hardwood flooring throughout main living area & newly update kitchen and bath. Kitchen with plenty of cabinet & counter space. Entertain or BBQ on your private private deck. Plenty of parking in your 1 car garage. Walk to the village!
Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 10 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s kitchen. Every detail is thoughtfully upgraded for comfort and style. Enjoy the privacy of a modern retreat in a warm, vibrant community—the perfect setting to make new memories.
A Diamond in the Rough! Calling all handymen to bring this Village Charmer back to its' original glory. This home has a large Living Room with a cozy alcove, spacious Dining Room and large Kitchen with sliders to a rear deck and yard. It also features 4 nice sized bedrooms. With a "little love and vision" this home could be a lovely family home! Could be a wonderful opportunity for investors! Close to shops and restaurants! Great commuter location! Come preview today!
Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 10 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s kitchen. Every detail is thoughtfully upgraded for comfort and style. Enjoy the privacy of a modern retreat in a warm, vibrant community—the perfect setting to make new memories.
Move in ready townhome with a NYC bus stop within the community!! Whispering Hills in Chester is perfectly positioned for commuters being 2 miles to Route 17. Enjoy a prefect blend of comfort and convenience with a maintenance free lifestyle in this two bedroom townhome. The main floor has brand new flooring, a living room with a wood burning fireplace,and a separate dining area ideal for entertaining.The kitchen has a tile backsplash, and a natural gas range. A convenient half bath and laundry area complete the first floor. Upstairs,the primary bedroom offers vaulted ceilings,a generous walk in closet and a full bath with private access to the hallway. The second bedroom is of ample size with a double door closet. A skylight in the hallways brightens the home. Additional features and highlights include central air, natural gas heating, an attached one car garage with extra storage, building roof replaced in 2022, HVAC 2013, skylight 2013, municipal water and sewer,reasonable hoa fees, snow removal and beautifully maintained grounds. Community amenities feature a dog park, playground, two pools, a gym and more. Just 5 minutes from the heart of Chester where you'll find local shopping,dining and entertainment all while remaining 70 miles from NYC, 10 minutes to LegoLand and close to Woodbury Common, Resorts Casino and Bethel Woods Concert Venue. Visit our nearby breweries, cafes,farmer market and historic Sugarloaf Village. Come see why everyone wants to live here!
Welcome to 2007 Whispering Hills Drive! This 2-bedroom, 1.5-bath condo offers comfortable living in one of Chester’s most desirable communities. The main level features a spacious living room with a real wood-burning fireplace, a dining area, and a kitchen with stainless steel appliances. Luxury vinyl plank flooring adds a modern touch throughout the main living areas. Upstairs, you’ll find two generously sized bedrooms and a full bath, while a convenient first-floor powder room is perfect for guests. Additional features include an attached two-car garage and access to Whispering Hills’ outstanding amenities, including a swimming pool, clubhouse, tennis courts, and basketball courts. Conveniently located close to shopping, restaurants, and major highways, this home offers easy, low-maintenance living with an unbeatable location.

Chester is located in New York. Chester, New York 10918has a population of 12,477. Chester 10918 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 10918 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 10918 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.