Chester, NY Homes for Sale with Garage

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  $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
• Explore Chester

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  /36

  $749,900

  • 4 Beds
  • 4 Baths
  • 3,080 Sq Ft

  20 Mountainside Dr, Chester, NY 10918

  20 Mountainside Drive, Chester, NY offers a spacious Colonial-style single-family home on approximately 1.6 acres with 4 bedrooms, 2 full baths, 2 half baths, 10 total rooms, and approximately 3,080 sq. ft. of above-ground living space. Built in 2021, this Chester residence features central cooling, gas heat, a full basement, fireplace, covered porch, patio, and Attached garage. Located in Orange

  

  Randolph Rogers

  eXp Realty

  20 Mountainside Dr, Chester, NY 10918
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  /39

  $489,000

  • 4 Beds
  • 1.5 Baths
  • 1,820 Sq Ft

  32 Surrey Rd, Chester, NY 10918

  Welcome to this well-maintained raised ranch in Chester, NY, offering 4 bedrooms and 1.5 bathrooms with plenty of space and flexibility. The home features hardwood floors, a bright and inviting layout, and comfortable living spaces throughout. Step outside onto the large deck overlooking a spacious backyard, perfect for outdoor entertaining, recreation, or simply enjoying the outdoors.

  

  Ammar Iqbal

  eXp Realty

  32 Surrey Rd, Chester, NY 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
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  /49

  $700,000

  • 4 Beds
  • 2.5 Baths
  • 3,296 Sq Ft

  13 Bianca Blvd, Chester, NY 10918

  Gracious Colonial home features the best of the traditional style with the appeal of a contemporary open floor plan in the kitchen - family room area. Meticulously maintenance and stylish updates create easy living spaces that are great for daily relaxation as well as entertainment. The full-length deck, large seating area around the fire pit and expansive yard provide outdoor areas to relax,

  Theresa Powers

  Keller Williams Realty

  13 Bianca Blvd, Chester, NY 10918
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  /49

  $495,000

  $95K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,916 Sq Ft

  22 Cambridge Cir, Monroe, NY 10950

  Impeccably maintained contemporary raised ranch in Lake Region Estates on prime corner lot, featuring an open floor plan ideal for everyday living and entertaining. Updated kitchen with center island, stainless steel appliances, and a bright garden window perfect for herbs and plants. Spacious living room offers a cathedral ceiling and oversized windows for abundant natural light. Dining area

  

  Jade Oliverio

  Howard Hanna Rand Realty

  22 Cambridge Cir, Monroe, NY 10950
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  /50

  $565,000

  • 3 Beds
  • 2 Baths
  • 1,724 Sq Ft

  1 Bell Way, Chester, NY 10918

  COLOR AT THE CURB. A POP OF PERSONALITY AT THE DOOR. FROM THE FIRST HELLO, THIS ONE FEELS LIKE HOME.Before you even step inside, this home makes a memorable first impression. The perennial garden, natural stone walkway, and inviting front door adds just the right pop of color and personality, setting the tone for a home that feels fresh, welcoming and anything but cookie-cutter. Tucked away

  

  Christina Rowan

  Howard Hanna Rand Realty

  1 Bell Way, Chester, NY 10918
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  /30

  $750,000

  • 4 Beds
  • 3 Baths
  • 2,280 Sq Ft

  1 Sanford Ave, Chester, NY 10918

  Welcome to 1 Sanford Avenue, a beautifully designed 4-bedroom, 3-bath Bilonial offering over 2,200 square feet of thoughtfully finished living space in Chester. The inviting exterior features a welcoming entry, attached 2-car garage, and attractive curb appeal.Inside, the open-concept layout is enhanced by soaring high ceilings, hardwood floors throughout, and a tiled foyer. The spacious

  Danielle Hinton Redfin Real Estate

  1 Sanford Ave, Chester, NY 10918
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  $290,000

  $25K PRICE DROP

  • 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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  $1,199,000

  $100K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 5,712 Sq Ft

  16 Sunset Ridge, Monroe, NY 10950

  NEW PRICE! Ready to sell! Highly motivated seller. Sold as-is. Recent updates include fresh paint in select areas and new pavers for enhanced curb appeal. Located approximately one hour from NYC with convenient access to major roadways.Welcome to this secluded Colonial in desirable Trout Brook Estates, set on nearly 6 private acres with over 5,700 sq ft of living space. This spacious

  Carmela Lopez Borrazas Serhant LLC

  16 Sunset Ridge, Monroe, NY 10950
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  /2

  $360,000

  Coming Soon

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

  3409 Whispering Hills, Chester, NY 10918

  Welcome to this inviting 3 bedroom, 2.5 bath condo nestled in the sought-after Whispering Hills community! Perfectly situated for commuters, this home combines comfort and convenience, with easy access to public transportation and proximity to major highways.Step inside to discover a well-maintained interior with an open-concept living and dining area featuring a wood burning fireplace,

  Bernadette Giordano Howard Hanna Rand Realty

  3409 Whispering Hills, Chester, NY 10918
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  $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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  /40

  $634,999

  $15K PRICE DROP

  • 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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  $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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  /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
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  /7

  $900,000

  • 4 Beds
  • 2 Baths
  • 2,466 Sq Ft

  651 Lakes Rd, Monroe, NY 10950

  Rare opportunity to purchase this gorgeous property that consists of 3 homes nestled on 3.5 beautiful acres. The main Colonial residence has been gutted and will need to be renovated/rebuilt, however, you can live in one of the additional two residences while you renovate! The 2nd residence called the “stone cottage” has 2 fieldstone fireplaces, a full kitchen, a vaulted ceiling in the bedroom, a

  Sandra Spector Howard Hanna Rand Realty

  651 Lakes Rd, Monroe, NY 10950
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  /19

  $429,000

  • 3 Beds
  • 1.5 Baths
  • 1,460 Sq Ft

  4 Maple Ln, Monroe, NY 10950

  Welcome to this beautifully updated Monroe home, ideally located just about 50 minutes from New York City. Set on a lush, well-kept property with mature trees and excellent curb appeal, this move-in-ready home offers a fresh modern look inside and out. The exterior features gray siding, white trim, a black front door, manicured landscaping, a newly paved driveway, and a spacious rear deck

  Joseph Rosenfeld Flag Realty Group

  4 Maple Ln, Monroe, NY 10950
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  /48

  $699,000

  • 3 Beds
  • 2.5 Baths
  • 2,533 Sq Ft

  173 Creamery Pond Rd, Chester, NY 10918

  Welcome to this charming three bedroom, two and a half bath colonial nestled in a welcoming neighborhood just minutes from the highway and the charming hamlet of Sugar Loaf. This inviting home offers a comfortable layout with plenty of space for everyday living and gathering. Outside, enjoy a flat, level yard that provides space for relaxing, entertaining, gardening, or outdoor activities.

  Michele Tobin Keller Williams Realty

  173 Creamery Pond Rd, Chester, NY 10918
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  /46

  $839,000

  • 4 Beds
  • 4 Baths
  • 2,707 Sq Ft

  34 Boville Ct, Chester, NY 10918

  Welcome to 34 Boville Court, a stunning, fully updated farmhouse colonial tucked away on a peaceful cul-de-sac and set on just shy of two acres. Thoughtfully designed with timeless style and modern functionality, this completely move-in-ready home offers an exceptional blend of space, comfort, and sophistication. Step inside to beautiful hardwood floors and a bright, inviting layout made for both

  Jillian Laga Keller Williams Valley Realty

  34 Boville Ct, Chester, NY 10918
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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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  $549,000

  $10K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,374 Sq Ft

  44 Wilson Rd, Monroe, NY 10950

  Welcome to this beautifully maintained 3-bedroom, 3-bath ranch nestled on a quiet dead-end street in the Lake Hill Farms community in the Town of Chester, within the Monroe-Woodbury School District. Offering municipal services, central air conditioning, and exceptional pride of ownership, this home is truly move-in ready. Step inside to a bright and inviting floor plan featuring a spacious living

  Claudia Lepore Keller Williams Realty

  44 Wilson Rd, Monroe, NY 10950
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  $750,000

  $50K PRICE DROP

  • 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
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  /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
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  /8

  $425,000

  • 3 Beds
  • 2 Baths
  • 2,460 Sq Ft

  23 Pike Ct, Monroe, NY 10950

  Welcome to 23 Pike Court. Unlock the potential of this spacious 3-bedroom, 2-bath raised ranch, which offers 2,460 square feet of living space on a generous .75 acre lot, giving you the space and flexibility to create something truly special. Perfect for an investor, contractor, or DIY enthusiast, this home is ready for someone with vision. While it needs work, it is move-in ready and offers an

  Patricia Sassi RE/MAX Benchmark Realty Group

  23 Pike Ct, Monroe, NY 10950
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  /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
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  /23

  $520,000

  $70K 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

  Craig Watters Compass Greater NY, LLC

  94 Booth Rd, Chester, NY 10918
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  /50

  $449,000

  • 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

  Soleil Jackman Howard Hanna Rand Realty

  66 Whitetail Run, Chester, NY 10918
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  /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
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  $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
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  /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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  /34

  $650,000

  • 3 Beds
  • 4 Baths
  • 2,520 Sq Ft

  29 Murray Dr, Chester, NY 10918

  Welcome to a contemporary retreat where refined design, exceptional craftsmanship, and a seamless connection to nature come together in one of Chester’s most desirable settings. Thoughtfully designed for both everyday living and effortless entertaining, this light-filled residence offers three bedrooms, two full bathrooms, and two half baths with an open, flowing floor plan that balances

  Liudmila Lobeeva eXp Realty

  29 Murray Dr, Chester, NY 10918
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  /28

  $539,000

  $41K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,698 Sq Ft

  24 Walnut St, Chester, NY 10918

  Welcome to 24 Walnut Street, Flexibility, Space & Endless Possibility in the Heart of Chester, NYTucked 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

  Tara Roufanis Keller Williams Village Sq Rlt

  24 Walnut St, Chester, NY 10918
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  /32

  $389,900

  • 3 Beds
  • 2.5 Baths
  • 1,694 Sq Ft

  213 Eagleton Dr, Monroe, NY 10950

  Some homes simply make everyday life easier, and 213 Eagleton Drive is one of them. This 3-bedroom, 2.5-bath townhome offers a practical layout with comfortable living spaces, an attached garage, additional driveway parking, and an unfinished basement for lots of storage. During the winter months, the home offers views of the community lake, adding a peaceful backdrop to the changing

  Deborah Warner Keller Williams Valley Realty

  213 Eagleton Dr, Monroe, NY 10950

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