Homes for Sale in 10918

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  /48

  $1,100,000

  • 5 Beds
  • 4 Baths
  • 5,312 Sq Ft

  53 Gibson Hill Rd, Chester, NY 10918

  Tucked away on over 3 private acres, this recently renovated custom residence offers a rare blend of seclusion, craftsmanship, and elevated living. Surrounded by hundreds of acres of protected state land, the setting ensures unmatched privacy with direct access to nature, including trails that connect to the Appalachian Trail just beyond your backyard. A natural waterfall adds to the serene

  

  Ammar Iqbal

  eXp Realty

  53 Gibson Hill Rd, Chester, NY 10918
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  /37

  $789,900

  • 5 Beds
  • 4 Baths
  • 4,697 Sq Ft

  19 Grand View Terrace, Chester, NY 10918

  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

  

  Randolph Rogers

  eXp Realty

  19 Grand View Terrace, Chester, NY 10918
• 

  

  

  /41

  $1,139,900

  $20K PRICE DROP

  • 4 Beds
  • 5 Baths
  • 4,624 Sq Ft

  16 Lori Ln, Chester, NY 10918

  Welcome to Chester, NY, a resort-style luxury colonial set on a private 1.1-acre cul-de-sac lot in the Monroe-Woodbury area of Orange County. This custom residence delivers the space, craftsmanship, and lifestyle today's relocation and move-up buyers are searching for, with approximately 4,624 square feet, refined architectural detail, mountain views, and seamless indoor-outdoor living. From the

  

  Randolph Rogers

  eXp Realty

  16 Lori Ln, Chester, NY 10918
• 

  

  

  /50

  $990,000

  $10K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,955 Sq Ft

  1 Oakland Ave, Chester, NY 10918

  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

  

  Christina Rowan

  Howard Hanna Rand Realty

  1 Oakland Ave, Chester, NY 10918
• 

  

  

  /18

  $399,000

  • Land
  • 46 Acres
  • $8,674 per Acre

  492 Black Meadow Rd, Chester, NY 10918

  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,

  

  Ewa Kusmierek

  eXp Realty

  492 Black Meadow Rd, Chester, NY 10918
• 

  

  /35

  $374,999

  $25K PRICE DROP Pre-Foreclosure

  • 4 Beds
  • 1.5 Baths
  • 1,560 Sq Ft

  241 Meadow Ave, Chester, NY 10918

  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

  

  Chativa Bowen

  Keller Williams Realty

  241 Meadow Ave, Chester, NY 10918
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  /33

  $315,000

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft

  4008 Whispering Hills Dr, Chester, NY 10918

  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

  Karen Taphorn Howard Hanna Rand Realty

  4008 Whispering Hills Dr, Chester, NY 10918
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  /36

  $375,000

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft

  1310 Whispering Hills, Chester, NY 10918

  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

  Joseph Williams Hudson Premium Realty

  1310 Whispering Hills, Chester, NY 10918
• 

  

  /38

  $1,200,000

  • 4 Beds
  • 2.5 Baths
  • 2,711 Sq Ft

  63 Whitetail Run, Chester, NY 10918

  This stunning 4 bedroom, 3 bathroom home with a beautifully updated kitchen is the perfect place to call home. With plenty of space to entertain and relax, you'll love the open layout and modern amenities that this home has to offer. Whether you're enjoying a meal in the spacious kitchen or unwinding in the cozy living room, you'll feel right at home in this charming and inviting space.

  Artan Kukaj SPIRAL NY Real Estate LLC

  63 Whitetail Run, Chester, NY 10918
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  /50

  $280,000

  $161K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 2,016 Sq Ft

  815 Craigville Rd, Chester, NY 10918

  We are proud to introduce this cornerstone property, located within what was once a thriving enclave of artists. The same owner since 1946, this home and studio are part of a small collection of historic properties that helped define the character of the area. Now, an extraordinary opportunity awaits for the next steward to write the next chapter of this remarkable property.Originally built

  MaryBeth O'Hara Ellis Sotheby's Intl Realty

  815 Craigville Rd, Chester, NY 10918
• 

  

  /37

  $749,000

  • 6 Beds
  • 3 Baths
  • 3,066 Sq Ft

  3 Grand View Terrace, Chester, NY 10918

  Discover refined living at 3 Grand View Terrace, a beautiful 6-bedroom, 3-bath Colonial in Chester's sought-after Valley View Phase II subdivision. This impressive home boasts 3,066 sq ft of living space, with a full walkout basement and an attached 2-car garage. Built in 2003, it features central air and forced air heat. Relax by the fireplace or enjoy the outdoor space on the 0.55-acre lot.

  Shalom Landau eRealty Advisors, Inc

  3 Grand View Terrace, Chester, NY 10918
• 

  

  /40

  $649,999

  • 4 Beds
  • 3 Baths
  • 2,316 Sq Ft

  424 Laroe Rd, Chester, NY 10918

  Rare opportunity in Chester! This 4-bedroom, 3-bath raised ranch sits on a private 2.5-acre lot and features a true 6-car garage — an uncommon and highly desirable feature that sets this home apart. The oversized garage offers exceptional flexibility: perfect for the car enthusiast, contractor, large family, or anyone who needs serious storage, a workshop, or space for boats, RVs, or equipment.

  Jeffrey Morrissey Epique Realty

  424 Laroe Rd, Chester, NY 10918
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  /24

  $295,000

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft

  2113 Whispering Hills Unit 178, Chester, NY 10918

  Welcome Home! 2 Bedrooms 1 Bathroom move in ready end unit. Recently renovated including a new kitchen with granite counter tops and stainless steel appliances, new bathroom, new windows, new laminate flooring, new water heater, new light fixtures and recessed lighting. Nothing to do but move in! Close to supermarket, post office, restaurants, urgent care, highway. Perfect commuter location.

  Valerie Quinn Keller Williams Realty

  2113 Whispering Hills Unit 178, Chester, NY 10918
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  /2

  $750,000

  • 5 Beds
  • 2.5 Baths
  • 2,700 Sq Ft

  3 Hilltop Ln, Chester, NY 10918

  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

  Moshe Kaufman MK Realty Inc

  3 Hilltop Ln, Chester, NY 10918
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  /5

  $759,900

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,250 Sq Ft

  90 Pewter Cir, Chester, NY 10918

  This beautiful custom home is planned to be built in the highly sought-after Sugar Loaf area, offering the convenience of municipal water and sewer. The main level welcomes you with warm hardwood floors and a kitchen featuring a choice of elegant granite or quartz countertops, a stainless steel appliance package, a center island perfect for meal preparation, and a spacious dining area with a

  Carla Terranova Keller Williams Realty

  90 Pewter Cir, Chester, NY 10918
• 

  

  /23

  $650,000

  $49K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,260 Sq Ft

  35 Peddler Hill Rd, Monroe, NY 10950

  "High-Value Property – Exceptional Location, Endless Potential" Discover an exceptional investment opportunity in a highly sought-after area! This charming home sits on over half an acre of prime real estate, making it perfect for investors, builders, or anyone looking to secure a valuable asset. With its spacious lot and desirable location, this property promises not only immediate returns but

  Joseph Rosenfeld Flag Realty Group

  35 Peddler Hill Rd, Monroe, NY 10950
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  /29

  $389,900

  • 3 Beds
  • 2 Baths
  • 1,393 Sq Ft

  4114 Whispering Hills, Chester, NY 10918

  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)

  Gzim Hakanjin Coldwell Banker Realty

  4114 Whispering Hills, Chester, NY 10918
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  /50

  $1,145,000

  $50K PRICE DROP

  • 9 Beds
  • 6.5 Baths
  • 4,965 Sq Ft

  19 High St, Chester, NY 10918

  Own One of America's Great Equestrian LandmarksSteeped 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

  Beth Palma Keller Williams Realty

  19 High St, Chester, NY 10918
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  /28

  $500,000

  • 3 Beds
  • 2 Baths
  • 2,688 Sq Ft

  5 N Hudson St Unit N, Chester, NY 10918

  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.

  Bernadette Corrigan Keller Williams Realty

  5 N Hudson St Unit N, Chester, NY 10918
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  /3

  $750,000

  • 5 Beds
  • 2.5 Baths
  • 2,700 Sq Ft

  2 Boville Ct, Chester, NY 10918

  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

  Moshe Kaufman MK Realty Inc

  2 Boville Ct, Chester, NY 10918
• 

  

  /47

  $825,000

  • 4 Beds
  • 2.5 Baths
  • 2,732 Sq Ft

  45 Whitetail Run, Chester, NY 10918

  Set on over 10 private acres in the rolling hills of Orange County, this exceptional custom colonial offers the rare combination of luxury, privacy, and convenience AND just minutes from the heart of Chester and major commuter routes. Built in 2017 and thoughtfully designed with over 2,700 square feet of living space, 45 Whitetail Run delivers the kind of lifestyle buyers dream about but rarely

  Melissa Forsyth Hudson Valley Home Connection

  45 Whitetail Run, Chester, NY 10918
• 

  

  /36

  $800,000

  • 4 Beds
  • 3.5 Baths
  • 3,100 Sq Ft

  985 Craigville Rd, Chester, NY 10918

  Welcome to your own private retreat, where timeless design, exceptional outdoor living, and over three acres of peaceful surroundings come together to create an unforgettable place to call home.Inside, the heart of the home is anchored by a stunning double sided fireplace that effortlessly connects the main living areas, creating warmth, character, and an inviting atmosphere for both everyday

  DAVID DEBERARDINIS Serhant LLC

  985 Craigville Rd, Chester, NY 10918
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  /49

  $749,999

  $50K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,718 Sq Ft

  58 Nancy Ln, Chester, NY 10918

  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

  Gina Dudgeon Howard Hanna Rand Realty

  58 Nancy Ln, Chester, NY 10918
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  /9

  $879,900

  • 4 Beds
  • 2.5 Baths
  • 3,200 Sq Ft

  1414 Kings Hwy, Chester, NY 10918

  Beautiful custom new homes to be built in Golden Meadows Estates, offering the rare combination of municipal water and sewer, thoughtfully designed floor plans, and stunning lots in a highly desirable location in the Warwick school district. Homes will start at $780,000, with multiple design options available to suit a variety of lifestyles. Lots 1 and 2 will feature custom Bilonial designs with

  Carla Terranova Keller Williams Realty

  1414 Kings Hwy, Chester, NY 10918
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  /29

  $549,900

  • 3 Beds
  • 2 Baths
  • 2,138 Sq Ft

  3318 State Route 94, Chester, NY 10918

  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

  Asha Keegan Howard Hanna Rand Realty

  3318 State Route 94, Chester, NY 10918
• 

  

  /37

  $340,000

  • 2 Beds
  • 1 Bath
  • 1,004 Sq Ft

  166 Bull Mill Rd, Chester, NY 10918

  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

  Stephen Ramundo Keller Williams Valley Realty

  166 Bull Mill Rd, Chester, NY 10918
• 

  /2

  $1,975,000

  • Land
  • 79.2 Acres
  • $24,937 per Acre

  0 Route 94 Unit KEY1035933, Blooming Grove, NY 10914

  A once-in-a-generation opportunity to acquire 79.2 acres in the highly sought-after Town of Blooming Grove. Rarely does a parcel of this size become available in one of Orange County's fastest-growing and most desirable communities. Whether you're a long-term investor, developer, or land banker, this exceptional property offers tremendous upside and the potential to capitalize on the area's

  Yoel Kornbluh Mount Realty

  0 Route 94 Unit KEY1035933, Blooming Grove, NY 10914
• 

  

  /35

  $377,000

  $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft

  1221 Whispering Hills, Chester, NY 10918

  Update: Last buyers financing fell through so this wonderful property can be yours!! This is a must see! Will not last! Welcome to this beautifully renovated, spacious 3-bedroom, 2.5-bathroom, end-unit condo offering privacy, comfort, and elevated living in the desirable Whispering Hills community in picturesque Chester, NY! Perfectly positioned at the end of the row for added privacy and natural

  Malia Leonard BUY NY REALTY LLC

  1221 Whispering Hills, Chester, NY 10918
• 

  

  /34

  $349,999

  • 3 Beds
  • 2 Baths
  • 1,316 Sq Ft

  3414 Whispering Hills, Chester, NY 10918

  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

  Kevin Grier KW Hudson Valley United

  3414 Whispering Hills, Chester, NY 10918
• 

  

  /20

  $894,000

  $105K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 3,535 Sq Ft

  220 Oxford Rd, Chester, NY 10918

  220 Oxford Road is a Truly Impressive Property! Offering over 3,500 sq ft of beautifully maintained living space, this home features 3 bedrooms plus an additional upper-level room, 3 full baths, and 1 half bath. Spacious living room, stunning family room, and a practical, well-designed kitchen. The home showcases elegant finishes throughout along with brand new flooring that adds a fresh modern

  Moche Halpern Blooming Realty

  220 Oxford Rd, Chester, NY 10918
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  /50

  $475,000

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft

  21 Trotting Dr, Chester, NY 10918

  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

  Michele Kayser Keller Williams Realty

  21 Trotting Dr, Chester, NY 10918
• 

  /2

  $725,000

  • 3 Beds
  • 2.5 Baths
  • 2,677 Sq Ft

  1 Arborvitae Ct, Chester, NY 10918

  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

  Moshe Kaufman MK Realty Inc

  1 Arborvitae Ct, Chester, NY 10918
• 

  

  /23

  $529,000

  $61K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,083 Sq Ft

  94 Booth Rd, Chester, NY 10918

  Some lots just have good bones. This one has it's own private nature trail, stocked pond rights, and a cul-de-sac that dead-ends into miles of nature trails anchored by a solid, spacious raised ranch on 1.8 acres. Inside, the home has been partially updated and offers solid bones with room to add your own touch over time. The house delivers where it counts. Three bedrooms, two and a half baths,

  Craig Watters Compass Greater NY, LLC

  94 Booth Rd, Chester, NY 10918
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  /46

  $775,000

  $113K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,740 Sq Ft

  149 Creamery Pond Rd, Chester, NY 10918

  Welcome to the highly sought-after Creamery Estate, located in the award-winning Warwick school district!. This inviting waterfront Colonial-style home offers the perfect blend of comfort, charm, and scenic beauty, set on an acre of beautifully maintained grounds with peaceful views of Creamery Pond. This 3-bedroom, 3 full bath home features hardwood floors throughout and a spacious, easy-flow

  Carla Terranova Keller Williams Realty

  149 Creamery Pond Rd, Chester, NY 10918
• 

  

  /50

  $449,000

  Open Sat 12PM - 2PM

  • 3 Beds
  • 1.5 Baths
  • 1,500 Sq Ft

  66 Whitetail Run, Chester, NY 10918

  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

  Soleil Jackman Howard Hanna Rand Realty

  66 Whitetail Run, Chester, NY 10918
• 

  

  /50

  $750,000

  • 5 Beds
  • 2.5 Baths
  • 2,700 Sq Ft

  3 Boville Ct, Chester, NY 10918

  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

  Dovid Hoffman MK Realty Inc

  3 Boville Ct, Chester, NY 10918
• 

  

  /46

  $615,000

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft

  412 Laroe Rd, Chester, NY 10918

  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

  Nathalie Sessoms Howard Hanna Rand Realty

  412 Laroe Rd, Chester, NY 10918
• 

  /2

  $350,000

  • Land
  • 2 Acres
  • $175,000 per Acre

  220 Oxford Rd, Chester, NY 10918

  A rare opportunity in Blooming Grove! This beautiful and flat 2-acre property offers endless potential in a calm and peaceful setting with a road frontage. Conveniently located just minutes from Prospect Garden, the land sits within the Monroe-Woodbury School District. With easy access to permits, this property is ideal for building your dream home or future investment. The neighborhood holds

  Chaim Weiss MS Realty Group USA, Inc

  220 Oxford Rd, Chester, NY 10918
• 

  

  /32

  $295,000

  • 2 Beds
  • 1.5 Baths
  • 1,086 Sq Ft

  2119 Whispering Hills, Chester, NY 10918

  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

  Jasmine Wadhwa Howard Hanna Rand Realty

  2119 Whispering Hills, Chester, NY 10918
• 

  

  /50

  $3,400,000

  • 4 Beds
  • 4 Baths
  • 7,750 Sq Ft

  19 Greentree Ln, Chester, NY 10918

  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

  Jake Garay Serhant LLC

  19 Greentree Ln, Chester, NY 10918

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