Chester, NY Homes for Sale

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  $730,000

  • 4 Beds
  • 3.5 Baths
  • 2,780 Sq Ft

  7 Park Place, Chester, NY 10918

  Welcome to your private, wooded oasis! This charming home perfectly blends convenience with comfort, featuring an ideal layout for multi-generational living or guests with two bedrooms and a full bathroom on the main floor. A cozy wood insert is the heart of the main living space, creating both warmth and a wonderful ambiance on chilly evenings. Beyond the existing bedrooms, there is additional

  

  Luanne McGann

  Century 21 Full Service Realty

  (845) 447-0221

  7 Park Place, Chester, NY 10918
• Explore Chester

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  $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
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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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  /8

  $699,990

  • 4 Beds
  • 3 Baths
  • 1,867 Sq Ft

  34 Mountainside Dr, Chester, NY 10918

  ONE LEVEL LIVING/ EASY COMMUTE- with additional space upstairs and down! ... Don't miss this beautiful TURN-KEY Arts & Crafts-style FARMHOUSE TO BE BUILT! ..... COME AND FULLY CUSTOMIZE this 4-bdrm, 3 bath, 2,106+/- sq. ft home (including bonus room)! LARGE MAIN FLOOR PRIMARY BEDROOM with ENSUITE BATH & WALK-IN CLOSET plus A SECOND MAIN FLOOR BEDROOM (NURSERY, OFFICE, CRAFT ROOM ETC.). FANTASTIC

  Karen Gauvin Our House Real Estate Group

  34 Mountainside Dr, Chester, NY 10918
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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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  /27

  $999,999

  • 5 Beds
  • 2.5 Baths
  • 4,772 Sq Ft

  2 Garnett Hill Rd, Chester, NY 10918

  A Private Suburban Retreat on Prestigious Garnet Hill. This Center Hall Colonial offers an exceptional residence- refined suburban living with the space, privacy, and sophistication sought by discerning buyers—just about an hour from Manhattan. Positioned on a beautifully landscaped 3+ acre property, the home features approximately over 4,700 square feet of elegant living space, offering 5

  Rachel Baruchov Platinum Realty Associates

  2 Garnett Hill Rd, 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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  /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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  /7

  $874,400

  • 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

  Frank Golio Howard Hanna Rand Realty

  651 Lakes Rd, Monroe, NY 10950
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  /2

  $639,000

  • 3 Beds
  • 1.5 Baths
  • 1,816 Sq Ft

  101 Oxford Rd, Chester, NY 10918

  This nice quiet house is a great place to call home. With almost 11 acres of land, there's a lot of space to enjoy activities and outdoor fun. The first floor of the house offers a nice layout with big living room, family room, kitchen, dining room, and a half bath. and a washer and dryer room . Bedrooms are nice and big making it very comfortable . The house will need some TLC and will need

  Nathan Landau Loop Realty Inc

  101 Oxford Rd, Chester, NY 10918
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  /34

  $999,000

  • 5 Beds
  • 4 Baths
  • 3,136 Sq Ft

  12 Damian Ct, Chester, NY 10918

  Welcome to 12 Damian Court, a spacious Colonial set on a quiet cul-de-sac. This well-maintained home offers 5 bedrooms and 4 bathrooms, with four bedrooms on the upper level and one additional bedroom in the finished basement. The main level features generous living and dining areas, perfect for everyday living and entertaining. The finished basement adds excellent flexibility with a second

  Elimelech Kremer MS Realty Group USA, Inc

  12 Damian Ct, Chester, NY 10918
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  /50

  $699,000

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

  360 Prospect Rd, Chester, NY 10918

  B"H Grab this opportunity!!! Cozy Home in great condition sitting on a 3.2 ACER Property!!! Enjoy the above ground pool !!!Wonderful neighborhood and calm area. Open living room with wood burning fireplace, The kitchen offers a breakfast bar, Center island, Stainless steel appliances, Multiple counter space and cabinets. Finished lower level with a Den/office, Family room and full bathroom.

  Joseph Mendlowitz eRealty Advisors, Inc

  360 Prospect Rd, 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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  /5

  $54,900

  • Land
  • 10.14 Acres
  • $5,414 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

  • 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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  /17

  $59,900

  • Land
  • 1.89 Acres
  • $31,693 per Acre

  71 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

  71 Carriage Knoll Rd, Chester, NY 12817
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  $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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  /5

  $259,000

  • Land
  • 20.18 Acres
  • $12,834 per Acre

  32 Mountainside Dr, Chester, NY 10918

  A RARE OPPORTUNITY to build your CUSTOM DREAM HOME on over 20 private acres in the sought-after Cooper's Ridge sub-division! This can truly be a mini-estate with near full privacy plus MOUNTAIN VIEWS!! FULLY ENGINEERED with NATURAL GAS, curb cuts! .... Site map in photos. This is one of only two remaining lots. Some wet-lands on the property. Drive way is not shared - it will be side-by-side with

  Karen Gauvin Our House Real Estate Group

  32 Mountainside Dr, Chester, NY 10918
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  /24

  $275,000

  • 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

  • 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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  $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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  /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
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  /13

  $239,900

  • 2 Beds
  • 1.5 Baths
  • 1,240 Sq Ft

  503 Mountain Laurel Dr, Monroe, NY 10950

  Peaceful country living in this two-story center lakefront unit with full basement located in Windridge community. Enjoy incredible mountain views from this large private Townhome. Primary bedroom on upper level with walk in closet and large sitting area which can be used as home office. Slider to rear patio with beautiful lake views!! Large living and dining area. Beautiful quiet complex close

  Margaret Galatro ARC Realty 1 in Sales

  503 Mountain Laurel Dr, Monroe, NY 10950
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  /23

  $400,000

  • 3 Beds
  • 1 Bath
  • 1,561 Sq Ft

  33 Meadow Ave, Chester, NY 10918

  One floor living at it best! Walk out your front door, sit on your rocking chair front porch with your morning coffee & enjoy the mountain views! This 3 bedroom 1 bath ranch offers hardwood flooring throughout main living area & newly update kitchen and bath. Kitchen with plenty of cabinet & counter space.Entertain or BBQ on your private private deck. Plenty of parking in your 1 car garage. Walk

  Ernie Acampora River Realty Services, Inc.

  33 Meadow Ave, Chester, NY 10918
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  $395,000

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

  223 Eagleton Dr, Monroe, NY 10950

  Welcome home to this tastefully updated and meticulously maintained 3 bedroom, 2.5 bath unit in a highly sought after community in the Monroe Woodbury school district. The Windridge community is clustered around ponds adding to the country feel. Located near the back of the cul-de-sac, this home features an open floorplan for easy living and entertaining. Step out of the sliding door in the

  Theresa Powers Keller Williams Realty

  223 Eagleton Dr, Monroe, NY 10950
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  /7

  $49,500

  • Land
  • 3.36 Acres
  • $14,732 per Acre

  20 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

  20 Carriage Knolls Rd, Chester, NY 12817
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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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  /78

  $699,900

  • Land
  • 337 Acres
  • $2,077 per Acre

  L 13.2 Friends Lake Rd, Chester, NY 12817

  2,200 feet of frontage along the Upper Hudson River, a wild, whitewater backcountry river, and immediate access to nearly 1,600 acres of State Forest Preserve, the Hudson River Woods & Wildwater property is the ''complete package'' of Adirondack property. With over 4,500 feet of road frontage (with electric) on Friends Lake Road, it's an ideal location for a camp, second home, or subdivision.

  John O'Donnell Timberland Realty

  L 13.2 Friends Lake Rd, Chester, NY 12817
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  $129,000

  • Land
  • 13.33 Acres
  • $9,677 per Acre

  L9 Bird Pond Rd, Chester, NY 12853

  Private 13+ acres of gently sloping land just minutes from Gore Mountain. Roughed-in driveway/Road leading from Bird Pond Rd. Several nice building locations around the property. One house-site staked-out for reference. Possible views from higher on the property with some select clearing. Listing agent will provide one set of existing preliminary building plans for the future homeowner from

  Walter Swartz Gallo Realty ADK Inc

  L9 Bird Pond Rd, Chester, NY 12853
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  /48

  $1,100,000

  • 4 Beds
  • 3.5 Baths
  • 4,467 Sq Ft

  53 Odyssey Dr, Chester, NY 10918

  Welcome to an extraordinary 4,400+ square foot residence in the coveted Warwick School district, where luxury and lifestyle converge to create the ultimate entertainer’s dream. This meticulously maintained and thoughtfully updated home offers breathtaking panoramic views, inviting you to unwind in the serene front atrium or the sun-drenched sunroom at the rear. Step inside to discover a

  Hilary Ryan Goldman Howard Hanna Rand Realty

  53 Odyssey Dr, Chester, NY 10918
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  /11

  $349,999

  • Land
  • 4.9 Acres
  • $71,428 per Acre

  8 Camelback Rd, Chester, NY 10918

  Nestled at the end of a private cul-de-sac, this 5 acre homesite offers breathtaking mountain and valley views in the sought-after Bull Mill Road area of Monroe/Chester, NY. The property’s gentle slopes create the perfect opportunity for a walkout lower level, allowing you to capture spectacular sunsets. This shovel-ready, fully approved, and engineered building lot features Belgian block

  James Feldhaus eXp Realty

  8 Camelback Rd, 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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  /20

  $68,900

  • Land
  • 3.26 Acres
  • $21,135 per Acre

  98 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

  98 Carriage Knoll Rd, Chester, NY 12817
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  /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 Exit Realty Venture

  220 Oxford Rd, Chester, NY 10918
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  /7

  $500,000

  • Land
  • 9.78 Acres
  • $51,125 per Acre

  30 Harding Way, Chester, NY 10950

  An exceptional opportunity for builders and investors in the highly desirable Town of Chester and Town of Monroe, within the Monroe–Woodbury School District. This offering includes four contiguous lots for the price of one, providing significant development potential. The assemblage consists of 30 Harding Way (0.18 acres; Section 27, Block 3, Lot 11), sold together with the adjoining parcels: Lot

  Ida Payne Keller Williams Realty

  30 Harding Way, Chester, NY 10950
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  /3

  $75,000

  • Land
  • 12 Acres
  • $6,250 per Acre

  L62.2 Moffitt Rd, Chester, NY 12817

  12-acre parcel offering beautiful terrain and privacy, yet on a town-maintained road. Plenty of options for a home setting. A very desirable property for your future home construction. Only 15 minutes to Gore Mountain Ski Area, 3 miles to Loon Lake and within a mile of the Hudson River. A wonderful opportunity to enjoy the Adirondack experience. $75,000

  Carol Monroe Najer Realty

  L62.2 Moffitt Rd, Chester, NY 12817
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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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  /8

  $39,500

  • Land
  • 1.82 Acres
  • $21,703 per Acre

  34 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

  34 Carriage Knolls Rd, Chester, NY 12817
• 

  

  /45

  $1,300,000

  • 4 Beds
  • 2.5 Baths
  • 3,866 Sq Ft

  2948 State Route 94, Chester, NY 10918

  Set atop a gentle hill with sweeping eastern views of Round Hill and Schunnemunk Ridge, this pristine 1860 farmhouse blends preserved historic character with thoughtful modern updates. Originally part of the Sears family dairy pasture, the 3,866 sq ft home has been meticulously maintained and features original wide-plank hardwood floors, a striking hand-carved banister, five fireplaces with

  Elizabeth Broderick Tuxedo Hudson Realty Corp

  2948 State Route 94, Chester, NY 10918
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  /33

  $289,500

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft

  1401 Whispering Hills, Chester, NY 10918

  Discover the perfect blend of comfort, convenience, and community in this 2-bedroom, 1-bath end-unit townhouse. Situated in a quiet corner of the neighborhood, this home offers extra privacy and natural light, along with the added benefit of an attached 1-car garage for secure parking and storage. Inside, you'll find a thoughtfully designed layout that maximizes space and livability - ideal for

  Debbie Goldstein Howard Hanna Rand Realty

  1401 Whispering Hills, Chester, NY 10918

Showing Results 1 - 40, Page 1 of 3

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 $585,799.

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

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

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

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

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

The median home price in Chester is $525,000. If you put a 20% down payment of $105,000 and had a 30-year fixed mortgage with an interest rate of 6.38%, your estimated principal and interest payment would be $2,620 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $112K a year to afford the median home price in Chester. Learn how much home you can afford with our Home Affordability Calculator.

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 Greenwood Lake Middle School. Browse all the schools in Chester, NY to learn more.

Home Trends in Chester, NY

On average, homes in Chester, NY sell after 58 days on the market compared to the national average of 55 days. The median sale price for homes in Chester, NY over the last 12 months is $515,000, up 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$515,000

Median Single Family Sale Price

$620,000

Median Townhouse Sale Price

$330,000

Median 2 Bedroom Sale Price

$305,000

Average Price Per Sq Ft

$268

Number of Homes for Sale

33

Last 12 months Home Sales

101

Months of Supply

3.90

Median List Price

$525,000

Median Change From 1st List Price

0%

Median Home Sale Price YoY Change

1%