Chester, NY Homes for Sale

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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
• Explore Chester

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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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  /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
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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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  /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

  1414 N Gore Rd, Chester, NY 12817
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  /33

  $355,000

  • 3 Beds
  • 2.5 Baths
  • 1,585 Sq Ft

  255 Heritage Ln, Monroe, NY 10950

  Welcome to Windridge! This well-maintained, move-in-ready 3-bedroom, 2.5-bath townhome offers comfortable, carefree living in a convenient Hudson Valley location. The first floor features a spacious eat-in kitchen with new stainless-steel appliances, a powder room, and an open living/dining area with sliding doors leading to the patio. Upstairs offers two bedrooms, a full bath, and a spacious

  

  Elsa Seguinot

  Coldwell Banker Realty

  255 Heritage Ln, Monroe, NY 10950
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  /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
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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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  /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
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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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  /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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  /5

  $49,900

  • Land
  • 1.76 Acres
  • $28,352 per Acre

  Unlisted Address

  Opportunity awaits on this 1.76-acre building lot in the heart of the Adirondacks, just minutes from Gore Mountain. Whether you're dreaming of an affordable year-round home or the perfect basecamp for skiing, hiking, mountain biking, snowmobiling, and everything the Adirondacks have to offer, this property provides an excellent starting point. Existing improvements include electric service, as

  

  Sean Rogge

  Howard Hanna Capital Inc

  Unlisted Address
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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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  /23

  $119,995

  • Land
  • 30.95 Acres
  • $3,877 per Acre

  1.3 Cobble Creek Rd, Chester, NY 12853

  Rarely does a property combine privacy, natural beauty and convenience as well as this 30-acre tract in Chester, New York. Located on a year-round town road, the land offers easy access while maintaining the peaceful feeling of a true Adirondack forest retreat. Several elevated APA-approved building sites are scattered throughout the property, offering ideal locations for an off-grid cabin or

  Marc Christmas Christmas and Associates

  1.3 Cobble Creek Rd, Chester, NY 12853
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  /33

  $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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  /32

  $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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  /5

  $49,000

  $16K PRICE DROP

  • Land
  • 10.14 Acres
  • $4,832 per Acre

  15 Deer Run, Chester, NY 12817

  10+ Acre recreational vacation location in the Town of Chester. Private maintained road with nice camps and homes. The lot feels as if its set in the heart of a wildlife preserve. Small non salvageable cabin on the property that had electric to the site. 6 miles to North Creek the home of Gore Mountain Ski Center. Build your vacation home here in the Adirondacks.

  Patricia Seitz McAlonen Pearsall Realty

  15 Deer Run, Chester, NY 12817
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  /23

  $68,900

  $19K PRICE INCREASE

  • Land
  • 3.11 Acres
  • $22,154 per Acre

  72 Carriage Knoll Rd, Chester, NY 12817

  Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

  Walter Swartz Gallo Realty ADK Inc

  72 Carriage Knoll Rd, Chester, NY 12817
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  /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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  /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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  /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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  /19

  $74,900

  $19K PRICE INCREASE

  • Land
  • 4.17 Acres
  • $17,962 per Acre

  77 Carriage Knoll Rd, Chester, NY 12817

  Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

  Walter Swartz Gallo Realty ADK Inc

  77 Carriage Knoll Rd, Chester, NY 12817
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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
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  /16

  $440,000

  • 3 Beds
  • 1.5 Baths
  • 1,728 Sq Ft

  1367 Kings Hwy, Chester, NY 10918

  Historic Colonial Era Home in the Heart of Sugar Loaf, NY. Located just 60 minutes from NYC. Zoned Residential/Commercial. Step into history with this one-of-a-kind 1,750 sq. ft. Colonial era home, where 18th-century charm meets 21st-century opportunity — right in the heart of the artisan hamlet of Sugar Loaf, NY. Built in 1770, this unique property features:• One of a kind Colonial era home,

  Derek Greene Greene Realty Group

  1367 Kings Hwy, 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
• 

  

  /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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  /18

  $189,000

  • Land
  • 3.14 Acres
  • $60,191 per Acre

  2 Dixon Rd, Chester, NY 12817

  Fish, Paddle, Build! Own an incredible 509' of private frontage on the Schroon River, complete with your very own mini island and over 3 buildable acres to create your Adirondack escape. Driveway is already in place with power available at the road, making your future plans even easier. Located just south of the dam (no direct access to Schroon Lake), this peaceful setting is ideal for fishing,

  Angie Mead Gallo Realty ADK Inc

  2 Dixon Rd, Chester, NY 12817
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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
• 

  

  /23

  $62,000

  • Land
  • 11.11 Acres
  • $5,581 per Acre

  62 Carriage Knolls Rd, Chester, NY 12817

  Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for a

  Walter Swartz Gallo Realty ADK Inc

  62 Carriage Knolls Rd, Chester, NY 12817
• 

  

  /25

  $155,000

  $10K PRICE DROP

  • Land
  • 31,798 Sq Ft
  • $212,329 per Acre

  L3 Emily Ln Unit Lot 3, Chester, NY 12817

  Rare opportunity to own a .73-acre vacant building lot with deeded dock and lake rights on beautiful Loon Lake. Located within the small and intimate Lakemont Association--featuring just 8 members--this property offers a unique chance to secure one of the few lake rights parcels with guaranteed docking. The lot is level and has already undergone selective clearing, making it an ideal canvas for

  Saraha Millington Gallo Realty ADK Inc

  L3 Emily Ln Unit Lot 3, Chester, NY 12817
• 

  

  /42

  $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
• 

  

  /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

Showing Results 1 - 40, Page 1 of 4

Why Live in Chester

Chester, NY, is a rural town with a rich history in the dairy industry, famously known as the birthplace of Philadelphia-style cream cheese. Located minutes from Hudson Valley attractions and retail centers in Woodbury, Chester offers a mix of small-town single-family homes and larger farmhouses on multi-acre lots. The town is accessible via Route 17, making it a convenient location with relatively lower home prices compared to nearby towns like Monroe. Chester features diverse recreational options, including the family-friendly Castle Fun Center with carnival rides, mini golf, and an indoor roller-skating rink. Carpenter Community Park serves as the town's central green space, offering a playground, picnic pavilion, and sports courts, while Goosepond Mountain State Park provides 1,500 acres of trails for hiking and horseback riding. The Orange Heritage Trail, accessible from the historic Erie Depot, runs almost 20 miles through the county. Local attractions include Legoland in nearby Goshen and the Capelli Sports Complex. Chester Mall offers grocery shopping at ShopRite and movies at Flagship Premium Cinemas, while the Chester Agricultural Center provides farm-fresh produce. Dining options include the Rustic Wheelhouse Restaurant, known for its Italian cuisine. Homes in Chester range from older, smaller houses to larger contemporary and Craftsman-style homes on spacious lots. The Windridge Mews condo subdivision offers two to three-bedroom units. The Chester Union Free School District serves the town, with Chester Elementary and Chester Academy providing various after-school activities. Commuters can reach New York City or Newark in about an hour and a half via Interstate 87 or Coach USA buses.

Learn more about living in Chester

Frequently Asked Questions

What is the average home price in Chester, NY?

Homes for sale in Chester, NY have an average home price of $631,466.

Are home prices dropping in Chester?

Yes, home prices in Chester are down 3% in the last 12 months.

How many homes have sold over the last 12 months in Chester, NY?

83 homes have sold in Chester, NY over the last 12 months.

What is the average household income in Chester, NY?

The average household income in Chester, NY is $137K.

What are the most popular zip codes in Chester, NY?

The most popular zip codes in Chester, NY include 10918, 10950, 10990, 10924 and 10921.

How much do you need to make to afford a house in Chester?

The median home price in Chester is $599,000. If you put a 20% down payment of $119,800 and had a 30-year fixed mortgage with an interest rate of 6.65%, your estimated principal and interest payment would be $3,080 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $132K a year to afford the median home price in Chester. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Chester is $137K.

How are the schools in Chester, NY?

Chester, NY has highly rated public and private schools. Some of the best schools in Chester based on Niche Grades are Greenwood Lake Elementary School, Warwick Valley High School and CJ Hooker Middle School. Browse all the schools in Chester, NY to learn more.

Home Prices in Chester, NY

The median home sale price in Chester, NY is $500,000, down 5% year-over-year. Homes in Chester sell in 66 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price $500,000	Median Single Family Sale Price $664,500
Median Townhouse Sale Price $320,000	Median 2 Bedroom Sale Price $310,000
Median 1 Bedroom Sale Price $370,000	Average Price Per Sq Ft $273
Number of Homes for Sale 69	Last 12 months Home Sales 83
Months of Supply 10.00	Median List Price $599,000
Median Change From 1st List Price 1%	Median Home Sale Price YoY Change -5%