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$370,000
3 Beds ⋅ 1 Baths ⋅ 1033159 MLS
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!

33 Meadow Avenue, Chester
$750,000
5 Beds ⋅ 3 Baths ⋅ 1031147 MLS
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.

3 Hilltop Lane, Chester
$279,999
2 Beds ⋅ 2 Baths ⋅ 1030827 MLS
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.

2007 Whispering Hills, Chester
$350,000
4 Beds ⋅ 1 Baths ⋅ 1031155 MLS
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!

151 Main Street, Chester
$750,000
5 Beds ⋅ 3 Baths ⋅ 1031045 MLS
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.

1 Hilltop Lane, Chester
$315,000
2 Beds ⋅ 2 Baths ⋅ 1027838 MLS
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!

4008 Whispering Hills Drive, Chester
$599,900
3 Beds ⋅ 2 Baths ⋅ 1029645 MLS
Located in the heart of the Village of Chester, this beautifully updated home offers the rare combination of modern comfort, privacy, and convenience. Just steps from Chester Academy and the Heritage Trail, this property provides easy access to walking, biking, running, local events, and community amenities while offering the peaceful retreat of your own private acreage. Set on 4 private acres, this home is a nature lover’s dream. The expansive property offers the perfect balance of open space and natural beauty, providing endless opportunities for outdoor enjoyment, family adventures, gardening, recreation, and creating your own private oasis. The large yard gives children plenty of room to play, explore, and connect with nature, while offering the space and flexibility for a hobby farm, gardens, chickens, outdoor activities, or other homesteading dreams. The entire home has been thoughtfully renovated within recent years, offering a fresh, updated feel throughout. A new HVAC system provides added comfort, efficiency, and peace of mind. The home also offers excellent future expansion potential with a full walk-out basement ready to be finished—perfect for a recreation room, guest suite, home gym, office, playroom, or media area. A standout feature is the oversized garage, providing exceptional space for vehicles, storage, hobbies, a workshop, or additional workspace. Step outside and enjoy the wrap-around back porch, the perfect place to relax, entertain, and take in the peaceful surroundings of your expansive yard. Whether enjoying morning coffee, hosting friends and family, or watching kids explore the outdoors, this space truly embraces the best of country-style living with village convenience. Property Highlights • Beautifully renovated home with modern updates • Just steps from Chester Academy and the Heritage Trail • Prime Village of Chester location close to schools, shops, and amenities • 4 private acres with beautiful natural surroundings • Perfect property for nature lovers and outdoor enthusiasts • Large yard ideal for kids to play, explore, and create memories • Endless possibilities for gardens, recreation, and hobby farming • New HVAC system • New roof • Full walk-out basement with finishing potential • Oversized garage with ample storage and workspace • Wrap-around back porch overlooking the property A rare opportunity to own a move-in ready home with land, updates, and endless possibilities—all in one of Chester’s most convenient locations. Whether you’re looking for space to grow, room for your family to explore, or the opportunity to create your own private retreat, 50 Hambletonian Ave offers the lifestyle you’ve been searching for.

50 Hambletonian Avenue, Chester
$575,000
6 Beds ⋅ 2 Baths ⋅ 992189 MLS
Rare opportunity. Come in and see this multi-family property in Chester, NY, and very close to main highways. This features 2 separate structures with their own utilities and natural gas. The main house presents 4 bedrooms, a kitchen, a dining room, and a living room with 1 full bath. main house is fully professional painted recently and now floors and roof on this house is 2 years old. The Second beautiful structure offers hardwood floors, as seen, 2 bedrooms, a kitchen, a living room, and 1 full bath. In addition, there is a garage about 750 sq that can be rented out for another few hundred dollars a month. Enjoy the beautiful 1.1-acre property. This unique property has multiple opportunities!

68 Conklingtown Road Unit #1&2, Chester
$389,900
3 Beds ⋅ 2 Baths ⋅ 1027245 MLS
WOW! Move right into this 3 Bedroom 2 Full bath "all on one level" (almost 1400 sq.ft.) beautifully maintained and updated END UNIT condo style home! You'll love the bright and open concept layout featuring the living room with vaulted ceilings and a gorgeous floor to ceiling fireplace as the focal point of the space. Within this area is easy access to the private deck (with new slider door) perfect for outdoor enjoyment and relaxation overlooking the pretty landscape. The kitchen has been thoughtfully renovated with new modern cabinetry, quartz countertops, updated backsplash, newer appliances (dishwasher, gas range and microwave), dedicated pantry with roll outs and ample shelving, new sink and pull out garbage drawer. Through the main entry level you have immediate access to the 1 car garage, which also has a dedicated storage space. This home has its own private entrance and the two story foyer offers a warm welcome to the unit. Notice how well maintained this home is as you tour. The primary bedroom is spectacular. This room is spacious and it has a large walk in closet and a gorgeous newly designed on suite full bathroom that feels like a "spa". Throughout the home, new flooring and window blinds have been installed, along with recessed lighting and a modern dining room chandelier. An added perk is that the entire condo was freshly painted in 2023. Further, additional significant updates offering peace of mind for years to come include: New furnace (2022) and new air conditioning unit (2023). There is also a smart thermostat system. This property is located in the Chester school district. Whispering Hills is an in-demand location - just minutes from shopping, restaurants, parks and more. Also, you'll love the easy access to main routes while enjoying the peaceful setting this development has to offer! Within Whispering Hills is the community pool for Summer fun, tennis court and sidewalks. Call for your private tour. Welcome home! *Special features sheet with more details and a floor-plan are available*

4114 Whispering Hills, Chester
$750,000
5 Beds ⋅ 3 Baths ⋅ 1025992 MLS
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.

2 Hemlock Court, Chester
$350,000
3 Beds ⋅ 3 Baths ⋅ 1025165 MLS
Welcome to 2604 Whispering Hills! This beautifully maintained, move-in-ready 3-bedroom, 2.5-bath townhome offers comfort, style, and numerous recent updates. Major improvements completed within the last five years include new windows, furnace, water heater, washer, and dryer, providing peace of mind for the new owner. The bright, spacious floor plan is perfect for everyday living and entertaining. Enjoy your own private patio with exceptional privacy—ideal for relaxing or hosting guests. A two-car garage provides ample parking and storage. Located in the highly desirable Whispering Hills community with access to outstanding amenities, and just minutes from shopping, restaurants, parks, commuter transportation, and Routes 17 and 94. This turnkey home combines convenience, low-maintenance living, and an unbeatable location. Don't miss this opportunity—schedule your showing today!

2604 Whispering Hills, Chester
$399,999
4 Beds ⋅ 2 Baths ⋅ 1024779 MLS
Discover the timeless charm and endless potential of this classic Colonial farmhouse, ideally situated on just under one level acre in the heart of Chester, NY. Offering approximately 1,560 square feet of living space, this 4 bedroom, 2 bath home is filled with character and craftsmanship. Step inside to find original hardwood floors, a cozy wood-burning stove, and an artistic, welcoming atmosphere that highlights the home's authentic farmhouse appeal. Rich with historic charm and original details, this property is ready for its next owner to restore and make it their own. Enjoy peaceful, scenic views of the surrounding greenery while benefiting from a highly convenient commuter friendly location. Just minutes from the highway, downtown Chester, Goshen, Monroe, and Warwick, you'll have easy access to local shops, restaurants, parks, wineries, farmers markets, and everything the Hudson Valley has to offer. Priced with the home's restoration needs in mind, this is a rare opportunity to invest in a property with incredible potential, generous outdoor space, and an unbeatable location. Whether you're searching for a primary residence, weekend retreat, or renovation project, this farmhouse is ready to be brought back to life. Schedule your private tour today and imagine the possibilities!

241 Meadow Avenue, Chester
$725,000
3 Beds ⋅ 3 Baths ⋅ 1024518 MLS
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 9 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.

1 Arborvitae Court, Chester
$349,999
3 Beds ⋅ 2 Baths ⋅ 974398 MLS
Welcome home to this beautifully updated 3-bedroom, 2-bathroom condominium with a 1-car garage, perfectly situated in the highly sought-after Whispering Hills community. Offering modern upgrades, spacious living, and resort-style amenities, this home is truly move-in ready. Step inside to discover a bright, open floor plan featuring gleaming hardwood floors, an updated chef-inspired kitchen with granite countertops, ample cabinetry, and plenty of prep space for entertaining. The renovated bathrooms offer stylish finishes and a fresh, modern feel with all new windows to help keep the indoor temperature steady. The spacious living room is filled with natural light and features a cozy wood-burning fireplace, creating the perfect place to relax year-round. The living room also opens through a brand-new sliding glass door to a private deck—ideal for morning coffee, outdoor dining, or simply enjoying the peaceful surroundings. The primary suite offers generous closet space and easy access to an updated full bath, while two additional bedrooms provide flexibility for family, guests, or a home office.

3414 Whispering Hills, Chester
$329,000
2 Beds ⋅ 2 Baths ⋅ 1018748 MLS
Beautifully maintained two bedroom condo with a two car garage in an excellent location within the highly desirable Whispering Hills community. Updated kitchen and newer flooring on the main level. Wood burning fireplace in the spacious living room. Sliding door from the dining area to the patio. The primary bedroom with tall vaulted ceilings has a large walk-in closet with custom California-closets style design features floor-to-ceiling shelves and cabinetry. Bedroom #2 also has custom closets. The outdoor patio with privacy fence overlooks the green area. Laundry area with storage shelves and full sized washer and dryer included. Central air conditioning and forced air heating. Natural gas and municipal water and sewer services. This home is in a fantastic location within Whispering Hills - tucked in the rear side of the community alongside the green area near the tennis courts, clubhouse, pool area, playground and dog run. Included with monthly HOA fee: Water, garbage and recycling, snow removal, landscaping, pool pass to two separate pool areas, use of tennis courts, basketball court, playground and clubhouse. Low taxes!!! Excellent commuter location. Bus stop to NYC/NJ in the complex. Close to the highway, supermarket, and shopping. Minutes from Woodbury Common, LegoLand NY, Garnet Health Medical Center, Chester Mall Shopping Center.

4118 Whispering Hills Drive, Chester
$850,000
5 Beds ⋅ 3 Baths ⋅ 1020076 MLS
Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new colonial-style residence invites you in with 12 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.

5 Hilltop Lane, Chester
$750,000
5 Beds ⋅ 3 Baths ⋅ 1020128 MLS
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.

3 Hemlock Court, Chester
$295,000
2 Beds ⋅ 2 Baths ⋅ 1019548 MLS
Step into this gorgeous Townhouse.Upon entering you’ll be welcomed by a perfect floor plan. The inviting living room features wooden floors, a cozy fireplace, and windows. The stylish kitchen has a functional layout and is outfitted with stainless steel appliances and granite countertops. The master-bedroom offers a modern feel and a walk in closet. Enjoy the amenity centers. Stop dreaming and start living, come and take a look today! The Condo charges $475 , HOA $250

2119 Whispering Hills, Chester
$649,999
4 Beds ⋅ 3 Baths ⋅ 1013375 MLS
Private 2.5-Acre Contemporary Retreat with Expansive Deck – Chester, NY Welcome to 424 Laroe Road — a rare opportunity to own 2.5 private acres in sought-after Chester. This solid 1974 contemporary home offers 2,316 square feet of flexible living space with 4 bedrooms and 3 bathrooms, perfectly positioned to take full advantage of its peaceful, tree-lined setting. Step outside onto the expansive multi-level deck and immediately feel the difference that true privacy and land can make. Ideal for entertaining, morning coffee, or simply enjoying the quiet, the outdoor living space is a standout feature rarely found at this price point. The generous lot offers room to expand, garden, play, or create your own outdoor oasis. Inside, the home provides a comfortable layout with bright living areas, multiple bedrooms, and the potential to personalize to your style. Ample garage and parking space add everyday convenience. Located in Orange County with easy access to major routes, this property delivers the space and privacy so many buyers are searching for — without sacrificing convenience. Whether you’re looking for a primary residence with room to grow or a peaceful retreat, 424 Laroe Road offers a strong foundation and exceptional land value. Key Features: 4 bedrooms | 3 bathrooms 2,316 sq ft 2.5 private acres Expansive deck for outdoor living Built 1974 – solid bones with modern potential Convenient Chester location Schedule your private showing today and experience the space, privacy, and potential for yourself.

424 Laroe Road, Chester
$789,900
5 Beds ⋅ 4 Baths ⋅ 1012919 MLS
Welcome to 19 Grand View Terrace in Chester, NY, an impressive Colonial offering approximately 4,697 square feet, five bedrooms, and four full bathrooms. Set on approximately 0.42 acres, this expansive Orange County residence provides the space, comfort, and flexibility needed for everyday living, entertaining, working from home, and hosting guests. The generous interior features multiple living areas, well-proportioned bedrooms, central air conditioning, and a versatile floor plan designed to accommodate a variety of lifestyle needs. At the heart of the home is a chef’s kitchen equipped with professional-grade appliances, offering an exceptional setting for preparing meals, entertaining guests, and gathering with family and friends. The finished lower level provides additional flexible space for a recreation room, media area, home gym, private office, or guest accommodations. An attached garage adds convenient parking and storage. Step outside and enjoy an inviting outdoor setting highlighted by an outdoor fireplace, creating the perfect atmosphere for relaxing evenings, seasonal gatherings, and memorable moments under the Hudson Valley sky. Located within the Chester School District, the property offers convenient access to local shopping, dining, recreation, commuter routes, and the many attractions of Orange County and the Hudson Valley. Buyers searching for a spacious five-bedroom home in Chester, NY, with a chef’s kitchen, professional-grade appliances, flexible living space, a finished lower level, and exceptional indoor-outdoor entertaining features will appreciate everything this property has to offer. 19 Grand View Terrace combines generous living space, elevated amenities, and a desirable Chester location—an exceptional opportunity to create the home and lifestyle you have been searching for.

19 Grand View Terrace, Chester
$849,999
4 Beds ⋅ 3 Baths ⋅ 1015381 MLS
Welcome to 24 Boville Court that sits on 3.7 acres a beautifully maintained home perfectly positioned on a quiet cul-de-sac in the highly desirable Town of Chester. Nestled on a premium end corner lot that extends all the way to Route 94, this exceptional property offers the perfect blend of privacy, comfort, and convenience. Step inside to discover bright, inviting living spaces, generously sized rooms, and a thoughtfully designed floor plan that’s ideal for both everyday living and effortless entertaining. Abundant natural light fills the home, creating a warm and welcoming atmosphere throughout. Outside, enjoy a peaceful backyard with plenty of space to relax, entertain, garden, or simply take in the surrounding nature. The spacious lot provides added privacy while still being just minutes from shopping, dining, parks, schools, and major commuter routes. This home is loaded with valuable upgrades and extras that will remain for the new owners, including beautiful landscaping, designer light fixtures, custom window shades throughout, a hardwired Lorex 6-camera outdoor security system, a reverse osmosis water filtration system in the kitchen, and a whole-house water softener—providing both comfort and peace of mind. Ideally located near the charming Village of Chester, you’ll also enjoy easy access to wineries, breweries, hiking trails, farm markets, and all the beauty and recreation the Hudson Valley has to offer. Whether you’re looking for your forever home, a weekend escape, or a smart investment, 24 Boville Court offers a rare opportunity to own a move-in-ready home in one of Orange County’s most sought-after communities. Schedule your private showing today and experience everything this exceptional property has to offer!

24 Boville Court, Chester
$990,000
4 Beds ⋅ 3 Baths ⋅ 1006113 MLS
Welcome to Brook Farm - Village of Chester, New York - Circa 1851 - 6.8 Acres. There's a moment, just after you turn onto Main Street and the house comes into view above the lawn, when you understand that this is not an ordinary property. The covered porch stretches wide across the front, the slate roof catches the afternoon light, and the whole thing sits there with the quiet confidence of something that has absolutely nothing to prove. Brook Farm has been here since 1851. It will be here long after you. This is the kind of home that changes the way you think about time. Originally the crown jewel of financier Richard Delafield's 128-acre Brook Farm estate — named after his Tuxedo Park retreat — the manor was designed from the very beginning for a life lived generously. For gathering people. For long dinners that drift into evening. For the kind of entertaining that doesn't need a theme, because the house is the occasion. Step through the front door and the ceilings rise to greet you — twelve feet of plaster and molding, the proportions of a home that was never meant to feel small. The formal rooms flow one into the next: parlor, drawing room, dining room, each anchored by original fireplaces, each telling you without a word that whoever built this place understood how a house should feel. The hardwood oak floors, the walnut trim, the two grand staircases with their original woodwork — these aren't period details. They're the bones of the place, still standing, still beautiful, still doing exactly what they were put here to do. Upstairs, four bedrooms carry the same unhurried character — rooms with depth and soul, served by two full baths and a dressing room. A walk-up third floor adds two finished bonus rooms: a studio, a library, a playroom, a quiet office above the treetops. The house keeps offering more. And then there's the basement. Name it what you want — a tavern, a speakeasy, a rumpus room — but nothing quite prepares you for it. A massive brick fireplace. A built-in bar. Full-size windows flooding the space with light. And a door that opens directly onto a sunken pebbled courtyard, walled and private, where summer evenings could easily become a habit. Beyond the main house, the estate unfolds across 6.8 acres of lawn, mature trees, and open land. A charming 882-square-foot guest cottage — two bedrooms, one bath, fully independent utilities — sits privately apart from the manor. It's the kind of setup that solves problems you haven't had to solve yet: visiting loved ones, aging parents, a long-term guest, a rental income stream, a caretaker's quarters. The dairy barn and outbuildings hint at the property's agricultural past and offer a footprint ready for whatever comes next — a workshop, a studio, a small farm, a vision that hasn't quite taken shape yet but will the moment you walk the land. There's even a tennis court. Fifty-five minutes from Midtown Manhattan, charming village setting, close to the Rail Trail, highways, the Goshen Historic Track, Legoland, the Shawangunk Wine Trail, and some of the best farm-to-table dining in the Hudson Valley — Brook Farm is private without being remote, historic without being frozen in time. Properties like this — with this much land, this much character, this much history — don't come back on the market. This one hasn't been available in over seventy years. The people who have lived here understood what they had. Now it's your turn. A special property steeped in character, with a story already written… and a bold new one waiting to begin. Full of soul and raw possibility, it’s ready for reinvention, for reimagination, for a whole new energy. Awaken its potential, elevate its spirit, and make it entirely your own. The next chapter is yours to craft. Your vision. Your legacy.

1 Oakland Avenue, Chester
$549,900
3 Beds ⋅ 2 Baths ⋅ 1008703 MLS
This beautifully updated homes features wood floors throughout, three spacious bedrooms, two den/office spaces, formal dining room, and two full baths. The expansive primary suite has an additional 10 X 10-ft. sitting room, generous walk-in closet, an en-suite with linen closet, walk-in shower and Venetian soaking tub. The main floor bathroom is equally large with a jetted bathtub. Both the living room ams the Primary have soaring cathedral ceilings and the dining room has a 10-ft. tray ceiling. Light pours into this homemaking the oversized living area bright and cherry. The inviting eat in kitchen features stainless appliances, and for extra storage a basement pantry features floor to ceiling shelves. There is also a basement laundry with included, oversized washer and dryer. An Additional laundry hook up is also available right outside the Primary suite. The living room has a fireplace clad in beautiful cultured stone with a wood burning insert for extra heat. Outside, mature landscaping frames this beautiful house. Enjoy relaxing on a two-tiered ,massive, low maintenance Trex deck surrounded by colorful perennial flowers that bloom every spring and summer. A stone fire pit sits center stage on the lower deck, and a large shed will hold all your gardening tool. In front a quaint porch provides more outside seating. There ia a garage and plenty of additional outdoor parking. The house has upgraded Hardie plank siding and stone. Enjoy country living and pace while still only being minutes from shopping, dining and the highway.

3318 State Route 94, Chester
$559,000
4 Beds ⋅ 3 Baths ⋅ 1004369 MLS
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.

24 Walnut Street, Chester
$399,000
1002697 MLS
Rare opportunity to own approximately 46 acres in the desirable Black Meadow Road area of Chester, New York. Tucked privately behind a subdivision entrance at the end of a cul-de-sac, this parcel offers a peaceful natural setting surrounded by mature woods, wetlands, scenic surroundings, and abundant wildlife. Ideal for recreational use including hiking, hunting, nature walks, bird watching, photography, and enjoying the outdoors. A perfect escape for those seeking privacy, tranquility, and a connection to nature while still being conveniently located within approximately 60 miles of New York City. Located in the heart of Orange County and the Hudson Valley, Chester is one of the region’s most sought-after destinations known for its beautiful countryside, rolling hills, farms, orchards, wineries, breweries, and year-round outdoor recreation. Enjoy close proximity to Goosepond Mountain State Park, Harriman State Park, Sterling Forest, the Heritage Trail, and countless hiking and biking opportunities throughout the area. Orange County offers a unique balance of rural beauty and everyday convenience with nearby shopping, restaurants, golf courses, farmers markets, ski areas, and entertainment. Just minutes from Woodbury Common Premium Outlets, Legoland New York, local equestrian facilities, and major commuter routes including Route 17/I-86, Route 6, and I-87. Convenient access to NJ Transit, Metro-North connections, and park-and-ride locations makes travel to New York City and surrounding areas easily accessible. Whether you are looking for a private nature retreat, recreational land, or a long-term investment opportunity, this property offers a rare chance to own a large parcel in one of the Hudson Valley’s most desirable locations.

492 Black Meadow Road, Chester
$749,999
3 Beds ⋅ 3 Baths ⋅ 995624 MLS
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.

58 Nancy Lane, Chester
$1,145,000
9 Beds ⋅ 7 Baths ⋅ 995148 MLS
Own One of America's Great Equestrian Landmarks Steeped in history and unlike anything else on the market, The Hambletonian House is a magnificent Victorian estate built in the 19th century by William Rysdyk, owner of the legendary Hambletonian 10—the foundation sire of nearly every modern Standardbred racehorse. More than a remarkable home, this is an opportunity to become the next steward of one of the most significant equestrian properties in history. Gracefully set atop a scenic knoll on nearly three private acres in the heart of Chester, New York, the estate offers exceptional privacy while remaining just 40 miles from Manhattan. From the moment you arrive, the home's commanding presence, timeless architecture, and beautifully maintained grounds create an unforgettable first impression. The stately main residence features seven bedrooms and four-and-a-half bathrooms, where authentic Victorian craftsmanship has been meticulously preserved. Soaring ceilings, original hardwood floors, intricate millwork, marble fireplaces, elegant pocket doors, and exquisite architectural details reflect the grandeur of a bygone era, while thoughtful modern updates provide today's expected comforts. Designed for both elegant entertainment and everyday living, the home's expansive gathering spaces flow effortlessly to the surrounding grounds, creating an ideal setting for celebrations, family gatherings, or quiet evenings enjoying the beauty of the property. Adding to the estate's resort-style appeal is a separate pool house, complete with a full bathroom and private sauna, offering the perfect retreat for relaxation, wellness, or entertaining guests throughout the seasons. One of the property's most compelling features is its detached second residence, offering a beautifully appointed two-bedroom apartment with exceptional flexibility. Beyond providing luxurious accommodation for guests or extended family, this separate living space creates an outstanding opportunity for additional income. Whether utilized as a premium long-term rental, short-term vacation rental, executive housing, caretaker's residence, or owner's quarters while operating the main home as a hospitality property, it provides the versatility today's buyers are seeking. Beyond its architectural beauty, the property presents an exceptional opportunity to offset ownership costs through multiple revenue streams. This rare combination of a landmark residence and an income-producing secondary dwelling makes the estate equally attractive to homeowners, investors, and entrepreneurs. With its iconic history, breathtaking setting, and expansive layout, The Hambletonian House is ideally suited as a luxury bed and breakfast, boutique inn, private event venue, executive retreat, or premier destination rental—offering limitless possibilities for both lifestyle and investment. The current owner has invested extensively in preserving the estate's historic integrity while making significant improvements to major mechanical systems and the roof, ensuring modern reliability without compromising its timeless character. This careful stewardship allows the next owner to enjoy the confidence of updated infrastructure while preserving a truly irreplaceable piece of history. Ideally located near the shops, restaurants, and conveniences of the Village of Chester, with easy access to major highways and the best of the Hudson Valley, the property offers the perfect balance of peaceful country living and metropolitan accessibility. Properties of this significance rarely become available. Combining rich history, exceptional architecture, income-producing potential, and an irreplaceable legacy, The Hambletonian House represents a once-in-a-generation opportunity to own one of the most celebrated equestrian landmarks. Some homes are purchased. Others become part of history. This is one of them.

19 High Street, Chester
$489,900
3 Beds ⋅ 3 Baths ⋅ 990509 MLS
Welcome to 35 Maple Avenue, a bright 3 bedroom, 3 full bath Raised Ranch in the desirable Village of Chester ideally located near the Village Park & School. This spacious 2,032 sq. ft. residence built in 2002 & Updated in 2020 including bathrooms & New Kitchen in 2024. The open main level features a White EIK with Quartz Counters & Island, stylish white tile backsplash, Pantry, Black Appliances, Recessed lighting & durable Vinyl plank floors -low maintenance & stylish for a busy lifestyle. Enjoy everyday living & entertaining with a formal dining room that opens to a sliding door to the back deck with a view. Sunny Living room with Bay window, cozy gas fireplace with a striking surround tile & vinyl plank floors perfect for relaxing evenings at home. . Down the hallway to a Primary suite with Full Private Primary bath, 2 additional bedrooms & second Full bath serves the remaining bedrooms. The finished lower level offers flexibility with a private full bath and family room with vinyl flooring and an additional room for an office, guest room or playroom. Laundry room. Practical conveniences include a spacious 2 car garage with Mechanicals and storage. Blacktop driveway with room for 4 cars. Public Water & Sewer is included in the taxes. In 2020 a new gas heating system was installed and updated Air conditioning in 2018. Set on .26 acre landscaped lot with road frontage in a quiet residential neighborhood. A generous back yard with a view of the Village Park. This home offers the perfect balance of comfort and convenient living in a sought-after village location. This is an excellent home for buyers seeking convenience, updates and flexible living. Includes a Shed. Solar Panels are leased. Close to major highways and shopping.

35 Maple Avenue, Chester
$3,400,000
4 Beds ⋅ 4 Baths ⋅ 988789 MLS
Set behind a gated entrance with a private guard house and unfolding across 8.4 private acres, The Retreat at Greentree is a true estate in every sense, engineered for privacy, designed for lifestyle, and positioned as one of the most unique offerings in the Hudson Valley. A cascading waterfall greets you on arrival, establishing a sense of calm and separation from the outside world. From that moment forward, every detail reinforces the same idea. This property was built intentionally, without compromise. Originally designed by renowned architect Paul Rudolph, the residence carries a level of architectural pedigree rarely available. Spanning over 7,750 square feet, the home blends that design legacy with modern performance, including radiant heated floors, geothermal systems, and thoughtfully curated living spaces that feel both refined and highly functional. What truly sets this property apart is the lifestyle it delivers. A private helipad offers direct access to Manhattan in approximately 14 minutes, redefining convenience at the highest level. The grounds unfold as a resort-caliber setting, anchored by a heated saltwater pool, three private cabanas, and a fully equipped outdoor kitchen with a dedicated dining space designed for effortless indoor outdoor living. A rare white sand beach introduces an unexpected element, creating a setting that feels more like a destination resort than a private residence. Inside, the home takes on a spa-like atmosphere, with wellness-driven features including a private sauna and spaces designed to restore and recharge. The primary suite is its own retreat, complete with a three-season room that extends the experience outdoors while maintaining complete privacy. A fully built-out home theater adds another layer to the lifestyle, bringing a true cinematic environment into the comfort of your own home. Beyond the property itself, the location adds another dimension. This is the perfect getaway for winter weekends, fall retreats, or summer escapes, surrounded by some of the Hudson Valley’s most sought-after destinations. Just minutes from LEGOLAND New York Resort, Woodbury Common Premium Outlets, Warwick Valley Winery & Distillery, local apple orchards throughout Warwick, Bear Mountain State Park for skiing and outdoor recreation, and the five-star Glenmere Mansion, the area offers a rare blend of recreation, luxury, and accessibility. Hiking, camping, fishing, skiing, biking, horseback riding, fine dining, and shopping are all within reach, creating a year-round lifestyle that is both active and refined. This is more than a residence. It is a fully realized compound, private, efficient, and architecturally significant, built for someone who values time, discretion, and a level of living that cannot be replicated.

19 Greentree Lane, Chester
$500,000
3 Beds ⋅ 2 Baths ⋅ 976521 MLS
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.

5 N Hudson Street, Chester
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