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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
$629,000
4 Beds ⋅ 2 Baths ⋅ 1030227 MLS
Gorgeous corner fully fenced in Bi-Level house for sale in Town of Goshen. State of the art heating system, central air, beautiful sunroom, modern kitchen and bathrooms. House was fully remodeled in 2014. The main level features three bedrooms, master bathroom has walk in closet with access to the bathroom, spacious living room, dinning room, kitchen and sunroom. The lower level offers additional living space with a fully finished basement, 4th bedroom, modern bathroom, additional storage space and laundry room. Extra large deck, above ground pool with paver patio. House is conveniently located to major highways, shopping, dinning and bus stations. Move in ready! Must come and see!

14 Larchwood Drive, Goshen
$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
$540,000
4 Beds ⋅ 2 Baths ⋅ 963560 MLS
Lovely raised ranch on a cul de sac. Updated kitchen and bathrooms. Open floor plan with a deck off the kitchen/dining area. The deck is fabulous and large, perfect for entertaining, dining al fresco, enjoying a beverage of your choice or lounging with a good read. Beautiful, large backyard. Don't miss the opportunity to own a home that gives you a lot for your money. Come explore the lay out see if it works for you.

5 Walnut Court, Goshen
$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
$579,999
4 Beds ⋅ 2 Baths ⋅ 1009268 MLS
MOVE-IN READY BI-LEVEL AVAILABLE IN GOSHEN/CHESTER AREA! If you're searching for an exceptional home in the desirable Goshen/Chester area with low property taxes, this beautifully updated bi-level is a must-see. Renovated in 2022 and offering nearly 2,000 square feet of meticulously maintained living space, this home combines modern style with everyday comfort. Step inside to discover beautifully refinished hardwood floors throughout the main level and a practical open-concept layout that’s ideal for today's lifestyle. The stunning eat-in kitchen serves as the heart of the home, featuring popular shaker-style cabinetry, abundant cupboard storage, elegant quartz countertops, modern stainless-steel appliances, and a functional center island with bar seating overlooking the large living room and adjacent dining area. The seamless flow between the kitchen, dining area and living room is perfect for daily living and entertaining. The cozy screened-in porch just off the dining area offers comfortable indoor-outdoor lounging space overlooking an inviting swimming pool with wraparound sun deck and a private patio area complete with BBQ grill (included). Situated on nearly half an acre of usable land, the property is fenced on three sides and offers ample space for a playground, pets, gardening, and outdoor gatherings. The main level includes three generously sized bedrooms, including a spacious primary suite with a walk-in closet and convenient access to the full hall bathroom. The fully finished lower level adds exceptional versatility, featuring a large family/game room with a charming wood-burning fireplace, a powder room, a fourth bedroom or home office, a dedicated laundry room with included washer and dryer, utility room access, and an attached one-car garage/workshop. Location is everything, and this home delivers. Tucked away in a quiet neighborhood and conveniently situated near shopping, dining, entertainment, and recreation, you're less than 10 minutes from Chester Commons (ShopRite, Flagship Cinemas, Tractor Supply, etc.) Castle Fun Center, Heritage Trail, and Legoland New York. You'll also enjoy easy access to Woodbury Common Premium Outlets, the Galleria Mall at Crystal Run, Angry Orchard & local wineries, Warwick, and Greenwood Lake. Commuters will appreciate the proximity to US-6 and the home's location just 60 miles from New York City. With its desirable location, modern updates, and strong short-term rental potential (Airbnb/VRBO), this property presents a rare opportunity for homeowners and investors alike. Don't miss your chance to make this exceptional home your own.

3 Elmwood Drive, Goshen
$550,000
4 Beds ⋅ 2 Baths ⋅ 1004057 MLS
Charming Split Three-Level fenced in property located Hudson Valley's Chester School District in Goshen, New York. Don't miss the opportunity to preview this beautiful home featuring three bedrooms, den, family room, two bathrooms, open and inviting floor plan designed for comfortable everyday living and entertaining. Step outside to a spacious rear yard complete with an above-ground pool and gazebo, creating the perfect setting for summer gatherings, relaxation, and outdoor enjoyment. Don't miss the opportunity to preview this beautiful home featuring an open and inviting floor plan designed for comfortable everyday living and entertaining. Conveniently located near major highways, public transportation, shopping, dining, and commuter routes to New York City, this property offers the ideal balance of accessibility and tranquility. Experience the charm and beauty of Hudson Valley living at its finest—where country comfort meets modern convenience.

2 Sycamore Lane, Goshen
$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
$3,200,000
5 Beds ⋅ 4 Baths ⋅ 956598 MLS
Set on 1.6 private acres overlooking Greenwood Lake and directly bordering the Appalachian Trail and protected state parkland, this nearly 5,920 SF modern residence feels suspended between civilization and nature. You’re not just buying a home. You’re securing protected views, mountain air, and lasting privacy. The architecture sets the tone immediately. Clean lines. A refined blend of metal and wood. Intentional design. Enter through a private mudroom and the scale unfolds. The main living space rises to ceilings nearing 30 feet, anchored by a dramatic double-height living and dining area framed by large-format, high-performance Wythe windows that capture the lake and mountain backdrop. Natural light floods the interior. European White Oak floors warm up the primary living areas, balancing the modern aesthetic. The open kitchen was designed for gathering, with a Bosch appliance package, exterior-vented hood, Sandy Shaker-style cabinetry by RTA, natural stone countertops and backsplashes, and contemporary Kohler fixtures flowing seamlessly into the entertaining spaces. An open loft overlooks the main level, complemented by a dedicated home office and a separate library or reading room, creating quiet retreats within an expansive layout. The primary suite feels restorative. A spa-inspired bath features large-format tile, a Kohler freestanding soaking tub, and a walk-in rain shower with ceiling-mounted head and linear drain. Natural stone counters, custom vanity cabinetry, integrated mirrored medicine cabinets, and layered lighting complete the space. Secondary baths carry the same elevated, durable finishes. The finished lower level offers flexible space for a gym, media room, bar, or lounge. Outside, nearly 2,000 square feet of decks and terraces extend the living areas outward, framing lake and parkland views with complete privacy. Built using Passive House principles, the home features a high-performance envelope and net-positive energy strategy supported by on-site solar. Advanced insulation, Passive House–certified windows, smart power monitoring, EV charging, and LED lighting throughout ensure exceptional efficiency and air quality. A fully integrated Savant system controls lighting, HVAC, sound, security, and energy management from your phone, delivering intuitive, connected living. A private two-car garage, dedicated laundry area, and thoughtful storage complete the functionality. What defines 95 Jersey Ave isn’t just its size or finishes. It’s the experience of living in architecture that respects its setting, opening to Greenwood Lake on one side and permanently protected land on the other. Modern mountain-lake living, executed at the highest level.

95 Jersey Avenue, Greenwood Lake
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