Newest Homes for Sale in Chester, NY

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  /6

  $450,000 Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,882 Sq Ft

  5 Roggia Rd, Chester, NY 10918

  Welcome to this spacious and versatile home nestled in the desirable town of Chester. Offering an abundance of living space, this property is ideal for those seeking comfort, flexibility, and room to grow. The home features a functional layout with generously sized bedrooms, a bright and inviting living area, and a well-appointed kitchen designed for everyday living and entertaining. Enjoy the

  

  Nazma Sooknanan

  Nazma Real Estate LLC

  (845) 606-3972

  5 Roggia Rd, Chester, NY 10918
• Explore Chester

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  /41

  $1,159,900 Coming Soon

  • 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

  (845) 493-2930

  16 Lori Ln, Chester, NY 10918
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  /36

  $875,000

  • 3 Beds
  • 2.5 Baths
  • 2,302 Sq Ft

  2 Pine Hill Rd, Chester, NY 10918

  The Conklin House: A Masterpiece of History & Modern Luxury. Experience the perfect blend of early 20th-century charm and 21st-century comfort. The Conklin House, a classic 1908 Queen Anne Victorian, stands as a commanding presence at the edge of the historic Village of Sugar Loaf. The home has always been used residentially but zoning permits commercial usage as well. Originally ordered from the

  Richard Ellis Ellis Sotheby's Intl Realty

  2 Pine Hill Rd, Chester, NY 10918
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  /44

  $599,000 Open Sat 12PM - 2PM

  • 4 Beds
  • 2 Baths
  • 2,056 Sq Ft

  6 Adams Ct, Monroe, NY 10950

  Stunning Split Ranch with Pool and Gorgeous Curb Appeal, Located in the Town of Chester within the Monroe-Woodbury School District Welcome to this beautifully maintained 4-bedroom, 2 full bath split ranch offering the perfect blend of comfort, style, and functionality. The upper level features a spacious and sun-filled eat-in kitchen, ideal for everyday living, with direct access to a big Trex

  Ida Payne Keller Williams Realty

  6 Adams Ct, Monroe, NY 10950
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  /38

  $349,900 Open Sat 1PM - 3PM

  • 1 Bed
  • 1 Bath
  • 783 Sq Ft

  58 Oxford Springs Rd, Chester, NY 10918

  Tucked away in a serene, wooded setting, this extraordinary private retreat offers a rare blend of craftsmanship and natural beauty. Surrounded by mature trees and complete privacy, this meticulously curated home is a true sanctuary—where every detail has been thoughtfully designed to elevate everyday living. From the moment you arrive, the property makes a lasting impression with its peaceful

  Christine Koenig Keller Williams Realty

  58 Oxford Springs Rd, Chester, NY 10918
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  /28

  $589,000

  • 3 Beds
  • 2.5 Baths
  • 1,854 Sq Ft

  101 Whitetail Run, Chester, NY 10918

  Looking for privacy, yet close to highways, shopping and transit. Look no further. Welcome to your new home on 3 private parklike acres. Spotless, lovingly maintained home featuring spacious open floor plan. Main level offering hardwood floors, large living room with cathedral ceilings, gas fireplace, built ins, eat in kitchen with quartz counters, stainless steel appliances and a formal dining

  Aylin Ippolito Cronin & Company Real Estate

  101 Whitetail Run, Chester, NY 10918
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  /32

  $355,000

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

  1311 Whispering Hills Unit 96, Chester, NY 10918

  Rare Opportunity! Welcome to this stunning 3-bedroom, 2-bathroom end-unit in the highly sought-after Whispering Hills community. This meticulously updated home features a modern kitchen with sleek gray cabinetry and stainless steel appliances. The spacious living area boasts soaring vaulted ceilings, recessed lighting, and a cozy electric fireplace—perfect for entertaining. Relax in the primary

  Michael Jenney Keller Williams Realty

  1311 Whispering Hills Unit 96, Chester, NY 10918
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  /42

  $499,900

  • 3 Beds
  • 2.5 Baths
  • 1,888 Sq Ft

  4 Oak St, Chester, NY 10918

  SPRAWLING BRICK RANCH!!! VILLAGE OF CHESTER! ALMOST 1900 SQ. FT. ON THE MAIN LEVEL!!! X- LARGE 1/2 ACRE LOT!!! Welcome to 4 Oak Street, nestled in the charming Village of Chester, NY. Offered for the very first time, this exceptional home was custom built for its original owners and has been lovingly maintained ever since—a true testament to quality craftsmanship and pride of ownership. Set on a

  Frank Muccari Cronin & Company Real Estate

  4 Oak St, Chester, NY 10918
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  /50

  $725,000

  • 4 Beds
  • 4 Baths
  • 3,908 Sq Ft

  78 Goshen Rd, Chester, NY 10918

  STOP THE SEARCH!!!! THIS ONE, IS ONE OF A KIND!!! HALF-COURT BASKETBALL COURT, RADIANT HEATED PRIVATE POOL, KILLER FINISHED LOWER LEVEL!!!!! Welcome to 78 Goshen Road, a beautifully maintained 4-bedroom Colonial in the Town of Blooming Grove within the sought after Washingtonville School District, set on a quiet country road with 2.3 acres of space and privacy. With over 3,900 square feet of

  Frank Muccari Cronin & Company Real Estate

  78 Goshen Rd, Chester, NY 10918
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  /45

  $590,000

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

  22 Cambridge Cir, Monroe, NY 10950

  Exceptional value in Monroe Woodbury! Well 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

  

  Jade Oliverio

  Howard Hanna Rand Realty

  (329) 666-0425

  22 Cambridge Cir, Monroe, NY 10950
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  /47

  $690,000 Open Sat 12PM - 2PM

  • 4 Beds
  • 3 Baths
  • 3,636 Sq Ft

  10 Hidden Dr, Monroe, NY 10950

  This expansive home offers 4 large bedrooms and 3 full bathrooms, providing the perfect blend of space and comfort. The updated kitchen and baths add a modern touch, while hardwood floors and high hats throughout enhance the home’s warm and inviting feel. An abundance of large windows fills the home with natural light. The full basement offers space galore, A beautiful brick fireplace serves as

  rosemary mcginn Century 21 Full Service Realty

  10 Hidden Dr, Monroe, NY 10950
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  /5

  $759,900

  • 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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  /19

  $450,000

  • 3 Beds
  • 1 Bath
  • 1,134 Sq Ft

  28 Branch St, Monroe, NY 10950

  Completely renovated and full of charm, this adorable Cape Cod in the Town of Monroe offers the perfect blend of comfort, style, and location—with coveted lake rights to Walton Lake. Featuring 3 bedrooms and 1 beautifully updated bath with a tiled shower, this home is truly move-in ready. The thoughtfully designed layout includes two bedrooms upstairs—one enhanced with a charming built-in

  Kassia Connors eXp Realty

  28 Branch St, Monroe, NY 10950
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  /21

  $549,000

  • 3 Beds
  • 1.5 Baths
  • 1,644 Sq Ft

  38 Jefferson Dr, Monroe, NY 10950

  Welcome home! This wonderful quiet neighborhood, Lake Hill Farms, off of Lakes Rd. On the outskirts of Monroe, makes this a great commuter and convenient location, from hiking trails, parks, Woodbury Commons, shopping, train station, and dinning. This home has a nice sized backyard. The deck furniture and gazebo are included, underneath your deck is an enclosed screened in patio which will give

  Lance Gibbs Arrowhead Realty

  38 Jefferson Dr, Monroe, NY 10950
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  /27

  $439,999

  • 3 Beds
  • 2.5 Baths
  • 1,384 Sq Ft

  99 Evan Rd, Warwick, NY 10990

  **Stylish Townhouse Living in the Heart of Warwick** Discover your next chapter at this beautifully updated semi-detached townhouse now available in one of Orange County's most charming communities. Offering three spacious bedrooms and two and a half bathrooms, this home seamlessly blends modern comfort with everyday functionality. Step inside and you'll immediately notice the thoughtful updates

  Derek Greene Greene Realty Group

  99 Evan Rd, Warwick, NY 10990
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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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  $415,000

  • 3 Beds
  • 2.5 Baths
  • 1,392 Sq Ft

  58 Darin Rd, Warwick, NY 10990

  Welcome to this beautifully renovated townhome offering the perfect blend of modern upgrades, natural light, and low-maintenance living in one of the Hudson Valley’s most desirable communities. Step inside to discover gleaming hardwood floors, an open and inviting layout, and a sun-filled living space designed for both comfort and entertaining. The updated kitchen features stainless steel

  Melissa Forsyth Hudson Valley Home Connection

  58 Darin Rd, Warwick, NY 10990
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  /42

  $305,000

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft

  3601 Whispering Hills, Chester, NY 10918

  Welcome to effortless living in the highly sought-after Whispering Hills community! This beautifully maintained 2-bedroom, 1-bath condo with a 1-car garage offers the perfect blend of comfort, style, and convenience.Step inside to discover a warm and inviting space enhanced by custom wall detailing, stylish flooring, and a cozy fireplace, creating the perfect setting for relaxing and

  Janet Rendle Weichert Realtors

  3601 Whispering Hills, Chester, NY 10918
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  /49

  $735,000 Open Sun 12PM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 3,356 Sq Ft

  55 Beverly Rd, Chester, NY 10918

  Welcome to 55 Beverly Road, Chester—A Stunning, Move-In Ready Home This beautifully updated 3,156 square-foot home blends timeless charm with modern upgrades, offering space, comfort, and style throughout. The expansive floor plan features bright, inviting living areas with soaring vaulted ceilings, gleaming hardwood floors throughout, and a cozy masonry fireplace that serves as a perfect focal

  Jay Himelson Howard Hanna Rand Realty

  55 Beverly Rd, Chester, NY 10918
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  /25

  $375,000

  • 3 Beds
  • 2.5 Baths
  • 1,355 Sq Ft

  4116 Whispering Hills, Chester, NY 10918

  Beautifully updated 3-bedroom, 2.5-bath Dogwood model townhouse located in Whispering Hills, a desirable corner unit setting. This home offers a perfect blend of comfort and modern upgrades.Step inside to find a thoughtfully refreshed interior with remodeled and freshly painted bathrooms, along with a bright, open layout. The kitchen is equipped with a brand-new refrigerator and dishwasher,

  Michael Casarella William Raveis-New York, LLC

  4116 Whispering Hills, Chester, NY 10918
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  /48

  $925,000

  • 5 Beds
  • 3.5 Baths
  • 3,680 Sq Ft

  21 Bull Mine Rd, Chester, NY 10918

  Welcome to this distinguished colonial residence offering five bedrooms and three and a half baths, gracefully positioned on 2.3 acres of private, scenic grounds. Set back from the road, the home is surrounded by expansive green lawns, providing an unparalleled sense of privacy and sophistication. The inviting front porch presents an ideal space to enjoy your morning coffee while taking in the

  Donna Gennaro Howard Hanna Rand Realty

  21 Bull Mine Rd, Chester, NY 10918
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  /3

  $48,000

  • Land
  • 3.6 Acres
  • $13,333 per Acre

  1414 N Gore Rd, Chester, NY 12817

  North Gore Lot - Come build your dream on home this 3.6 acre wooded lot with power available roadside and perc test completed. Secluded location, yet only 15 minutes to Gore Mountain and 10 minutes to Minerva Beach with abundant outdoor recreation opportunities.

  

  Amanda Gadway

  Gadway Realty

  (518) 768-9981

  1414 N Gore Rd, Chester, NY 12817
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  /49

  $650,000

  • 5 Beds
  • 3 Baths
  • 2,983 Sq Ft

  9 Mount Ridge Ct, Monroe, NY 10950

  Spacious Center Hall Colonial with open concept kitchen, fireplace, deck, and large primary suite with walk-in closets. A dramatic two-story entry leads to an open concept kitchen with abundant counter space, large dinette area, and sliding doors to a spacious deck --perfect for entertaining. The kitchen flows into the open family room and living room with fireplace, creating an ideal setup for

  Richard Froehlich RE/MAX Benchmark Realty Group

  9 Mount Ridge Ct, Monroe, NY 10950
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  /38

  $350,000

  • 2 Beds
  • 1 Bath
  • 1,272 Sq Ft

  307 Gibson Hill Rd, Chester, NY 10918

  Looking for a solid built home with great bones and a lot of space in the Warwick School District? This spacious ranch home is waiting for your modern touches. Built strong, this home is in need of some cosmetic updates but you can live in the home and enjoy it as you go. This home offers 2 bedrooms (plus a den) and a full bath. The kitchen makes every square inch count with ample storage and

  Donna Gennaro Howard Hanna Rand Realty

  307 Gibson Hill Rd, Chester, NY 10918
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  /24

  $362,900

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

  2203 Whispering Hills, Chester, NY 10918

  Welcome to 2203 Whispering Hills, Chester, NY — Where Comfort Meets ConvenienceThis sun-drenched end-unit townhome offers the perfect blend of space, style, and location in the sought-after Whispering Hills community.Featuring 3 spacious bedrooms and 2.5 bathrooms, this home is designed for both everyday comfort and effortless entertaining. The inviting living room is anchored by a cozy

  Marie Altieri Howard Hanna Rand Realty

  2203 Whispering Hills, Chester, NY 10918
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  /20

  $360,000

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

  4 Maple Ln, Monroe, NY 10950

  If you possess talent and intelligence, this is your moment! Attention First time homebuyers and astute investors! Seize this opportunity to improve this charming Fixer upper home. With a little tender loving care, it can be wonderful once more. Situated in a fantastic area, with all amenities nearby. With some effort you can enjoy the benefits forever!

  Joseph Rosenfeld Flag Realty Group

  4 Maple Ln, Monroe, NY 10950
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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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  /8

  $869,900

  • 4 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  10 Well Sweep Ln, 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

  10 Well Sweep Ln, Chester, NY 10918
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  /48

  $499,999

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

  35 Maple Ln, Monroe, NY 10950

  Is there a 3-bed ranch in Monroe NY under $500K with a finished basement, pool, and commuter convenience? 35 Maple Ln is a 3-bedroom, 2-bathroom ranch offered at $499,999 with 1,460 sq ft of living space, including 960 sq ft above grade and a 500 sq ft finished basement. Built in 1964, this single family residence offers true single level living plus flexible lower level space ideal for

  Kewin Garabito eXp Realty

  35 Maple Ln, Monroe, NY 10950
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  /50

  $820,000

  • 4 Beds
  • 2.5 Baths
  • 3,120 Sq Ft

  558 Pine Hill Rd, Chester, NY 10918

  Beautifully spacious Colonial set on 1.8 private acres on Pine Hill Road, offering 3,120 square feet of rustic, updated charm behind a gated entry and surrounded by magnificent grounds. The main level welcomes you with a spacious eat-in kitchen that flows seamlessly into the dining area, creating an ideal setting for everyday living and effortless entertaining. The massively large living room

  Charnie Guttmann eRealty Advisors, Inc

  558 Pine Hill Rd, Chester, NY 10918
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  /2

  $350,000

  • Land
  • 5.7 Acres
  • $61,404 per Acre

  552 Pine Hill Rd, Chester, NY 10918

  Beautiful 5.7-acre residential parcel located in the Town of chester, offering an exceptional opportunity to build your custom dream home in a peaceful, private setting. With ample space for a spacious residence and outdoor living areas (subject to town approvals), this property combines natural surroundings with convenient access to nearby amenities, schools, and major roadways. Adjacent to 558

  Charnie Guttmann eRealty Advisors, Inc

  552 Pine Hill Rd, Chester, NY 10918
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  /2

  $249,900

  • 2 Beds
  • 1.5 Baths
  • 1,053 Sq Ft

  1005 Whispering Hills, Chester, NY 10918

  ONLY CASH OFFERS!! LOW TAXES! Two Level Living! 2 Bedrooms! 1 1/2 Bathrooms! 1 Car Garage! Updated Kitchen! Updated Bathrooms! Living Room with Fireplace! Sliders To Patio! Perfect Commuter Location! Walk to NYC Bus & Shopping! Close to Major Highways! Country Club Living! Clubhouses! Pools! Tennis! Tot Lot! Basketball! Dog Walk!

  Amanda Dnistrian ARC Realty 1 in Sales

  1005 Whispering Hills, Chester, NY 10918
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  /9

  $149,900

  • Land
  • 0.2 Acre
  • $735,886 per Acre

  2 Imperial Park, Chester, NY 10918

  Large 2 story storage barn approx 80' x 30' with silo for sale in the Town of Chester. 5 garage doors - 4 are 6 feet high, 1 door is 7 foot high with loading dock. Plenty of storage on first and second level. Small office. Has electric, but is turned off. Has well water, but no septic - lot is too small - only .20 acre. Not a buildable lot. Barn was subdivided off from neighboring farm. Has loft

  William Scolza HomeSmart Homes & Estates

  2 Imperial Park, Chester, NY 10918
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  /23

  $410,000

  • 2 Beds
  • 1 Bath
  • 1,026 Sq Ft

  7 Hambletonian Ave, Chester, NY 10918

  This 2 bedroom charmer with additional room offers potential 3 bedrooms. Larger than it looks - need to see. Discover the timeless charm and surprising spaciousness of this delightful carriage house, set on a property rich with character and possibility. Step inside to a generous living room where a wood burning fireplace, hardwood floors, and a large bay window create a bright, welcoming

  William Scolza HomeSmart Homes & Estates

  7 Hambletonian Ave, Chester, NY 10918
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  /46

  $849,999

  • 5 Beds
  • 5.5 Baths
  • 5,403 Sq Ft

  4 Debbie Ct, Chester, NY 10918

  DISCOVER THE EPITOME OF LUXURY LIVING! With 5400 sq ft of breathtaking property, where every corner is designed for both elegance and practicality!! With expansive living areas, high-end finishes, and modern amenities, this home is perfect for entertaining or enjoying quiet moments. Embrace a lifestyle of comfort and sophistication in a space that truly feels like a retreat all year

  Joseph Rosenfeld Flag Realty Group

  4 Debbie Ct, Chester, NY 10918
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  /50

  $1,725,000

  • 4 Beds
  • 2.5 Baths
  • 3,348 Sq Ft

  20 Goshen Rd, Chester, NY 10918

  THE ULTIMATE HUDSON VALLEY LEGACY ESTATE | 53 ACRES OF UNMATCHED POTENTIAL Rarely does a property emerge that perfectly balances refined luxury living with raw, untapped opportunity. Nestled in the heart of scenic Chester, New York, 20 Goshen Road offers an expansive 53-acre canvas designed for the visionary. Whether you envision a world-class equestrian facility, a high-potential residential

  Ramanjit Dhanoa eXp Realty

  20 Goshen Rd, Chester, NY 10918
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  /39

  $319,900

  • 3 Beds
  • 2.5 Baths
  • 1,320 Sq Ft

  607 Mountain Laurel Dr, Monroe, NY 10950

  Monroe-Woodbury Schools Townhouse with Low Taxes — Zoned for highly sought-after Pine Tree & Sapphire Elementary Schools. Step into this inviting 3-bedroom, 2.5-bath townhouse in the desirable Windridge community where space, light, and thoughtful updates come together. The spacious living room showcases younger laminate flooring that looks beautiful and cleans like a dream, while front-facing

  Rosalie Cook Weichert Realtors

  607 Mountain Laurel Dr, Monroe, NY 10950
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  /47

  $725,000 Open Sun 12PM - 4PM

  • 6 Beds
  • 3.5 Baths
  • 4,204 Sq Ft

  487 Black Meadow Rd, Chester, NY 10918

  A Landmark Farmhouse with a Story to Tell.Standing proudly since 1872, this historic Colonial farmhouse is one of the very first homes built on Black Meadow Road and remains a meaningful piece of Chester’s agricultural past. Once surrounded by hundreds of acres of open farmland and dairy cows, the home still carries the soul of a working farm while offering the comforts of modern living. With

  Dominic Santagato Joseph Baratta Company Realty

  487 Black Meadow Rd, Chester, NY 10918
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  /26

  $699,999 Open Sat 12PM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 2,544 Sq Ft

  5 Bens Way, Chester, NY 10918

  Welcome to 5 Bens Way, a beautifully positioned residence tucked away on a quiet cul-de-sac in the highly sought-after Town of Chester, New York. This property offers an exceptional blend of privacy, space, and convenience, making it an outstanding opportunity for buyers seeking a well-rounded Hudson Valley lifestyle with easy access to modern amenities, commuter routes, and recreational

  Anthony Rivas Keller Williams Hudson Valley

  5 Bens Way, Chester, NY 10918
• 

  

  /19

  $83,500

  • Land
  • 2.84 Acres
  • $29,401 per Acre

  38 Granite Ridge Rd, Chester, NY 12817

  Private 2.84-acre partially cleared, buildable lot in a peaceful setting with proposed home and septic locations. Property features a gravel driveway with camper pad, Amish-built shed on gravel base, fire pit, and walking trail. Infrastructure in place includes 200-amp underground electric service plus 30-amp and 50-amp RV hookups. Conveniently located minutes from Cronin's Golf Resort, Friends

  Nicholas Khachadourian KW Platform

  38 Granite Ridge Rd, Chester, NY 12817

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