Chester, NY Homes for Sale

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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

  (845) 493-2930

  16 Lori Ln, Chester, NY 10918
• Explore Chester

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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

  (845) 328-2396

  53 Gibson Hill Rd, Chester, NY 10918
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  /4

  $350,000

  $50K PRICE INCREASE

  • Land
  • 5.1 Acres
  • $68,627 per Acre

  0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918

  Very private lot in mature subdivision of large homes. Home site has been cleared and driveway base laid down. With a small amount of brush-clearing in the tree line there can be views of the valley and watershed lands.

  

  Theresa Powers

  Keller Williams Realty

  (845) 713-9754

  0 Odyssey Dr Unit KEY858370, Chester Town, 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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  /50

  $1,000,000

  • 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

  (845) 237-3716

  1 Oakland Ave, Chester, NY 10918
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  /37

  $424,999

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

  2722 Whispering Hills Unit 542, Chester, NY 10918

  New beginnings offered in this light and bright fully refreshed end unit in the highly sought after Whispering Hills community. Featuring new designer paint throughout, brand new luxury vinyl plank (LVP) flooring, new stainless steel appliances, two car garage with recently installed garage doors and so much more. Located close to major highway, NYC bus and shopping. Club house with gym,

  

  Erin Connolly-Frontino

  Artisan Realty

  (845) 932-1237

  2722 Whispering Hills Unit 542, Chester, NY 10918
• 

  

  /18

  $399,000

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

  492 Black Meadow Rd, Chester, NY 10918

  Rare opportunity to own approximately 46 acres in the desirable Black Meadow Road area of Chester, New York. Tucked privately behind a subdivision entrance at the end of a cul-de-sac, this parcel offers a peaceful natural setting surrounded by mature woods, wetlands, scenic surroundings, and abundant wildlife. Ideal for recreational use including hiking, hunting, nature walks, bird watching,

  

  Ewa Kusmierek

  eXp Realty

  (845) 582-7035

  492 Black Meadow Rd, Chester, NY 10918
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  /47

  $985,000

  • 5 Beds
  • 3.5 Baths
  • 3,764 Sq Ft

  86 Long Vista Ln, Chester, NY 10918

  Some properties are simply worth talking about... this one has all the bells & whistles you're seeking! Privately set on 5.2 scenic acres within the Warwick School District and just one hour from NYC, this distinguished Colonial pairs timeless elegance with resort-style outdoor living, mountain views, and exceptional multi-generational flexibility. A gracious front porch sets the tone, welcoming

  

  Jennifer DiCostanzo

  RE/MAX Town & Country

  (845) 606-3942

  86 Long Vista Ln, Chester, NY 10918
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  /45

  $548,000

  $42K 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

  (329) 666-0425

  22 Cambridge Cir, Monroe, NY 10950
• 

  

  /22

  $79,995

  • Land
  • 20.26 Acres
  • $3,948 per Acre

  1.2 Cobble Creek Rd, Chester, NY 12853

  Escape to the mountains with this beautiful 20-acre property in Chester, NY, ideally situated along a year-round maintained town road. The terrain gently climbs from the road, leading to multiple APA-approved building sites for an off-grid cabin or hunting camp offering excellent privacy in a quiet woodland setting. The property features a healthy forest of Northern hardwoods including maple,

  Marc Christmas Christmas and Associates

  1.2 Cobble Creek Rd, Chester, NY 12853
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  /2

  $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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  /22

  $89,995

  • Land
  • 25.03 Acres
  • $3,595 per Acre

  Rd, Chester, NY 12853

  Adirondack Mountain Retreat with Stream and Trails Discover 25 acres of classic Adirondack wilderness in Chester, New York, tucked along a year-round, town-maintained road. This exceptional property rises gently from the roadside to several attractive, APA-approved building locations, offering excellent opportunities for an off-grid cabin, or vacation retreat. The land is heavily wooded with a

  Marc Christmas Christmas and Associates

  Rd, Chester, NY 12853
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  /50

  $675,000

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

  9 Derose Ln, Chester, NY 10918

  Welcome to this elegant colonial in the highly regarded Warwick School District, where timeless charm meets modern comfort. Relax on the inviting front porch while enjoying your morning coffee and breathtaking mountain views. Inside, spacious sun-filled rooms and hardwood flooring throughout the formal living and dining areas create a warm, welcoming atmosphere. A dramatic two-story foyer sets

  Donna Gennaro Howard Hanna Rand Realty

  9 Derose Ln, Chester, NY 10918
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  /41

  $569,000

  • 4 Beds
  • 2.5 Baths
  • 2,040 Sq Ft

  78 Pickerel Rd, Monroe, NY 10950

  Beautiful and spacious 4 Bedroom, 2.5 Bath Colonial set on park-like property in a lovely neighborhood with a serene backdrop of mature trees, offering both privacy and a peaceful setting. This home features a large eat-in kitchen with abundant cabinetry, tremendous counter space, and a sliding glass door leading to a newer rear deck—perfect for relaxing or entertaining outdoors.The oversized

  Mary Ann Mitchell eXp Realty

  78 Pickerel Rd, Monroe, NY 10950
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  /29

  $1,299,000

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

  16 Sunset Ridge, Monroe, NY 10950

  Secluded Trout Brook Estate: Expansive 5,700+ Sq Ft, 6-Car Garage, Ready for Multi-Gen Living and Entertaining. Nestled on nearly six private acres in the exclusive Trout Brook Estates, this expansive Colonial-style estate blends classic elegance with modern comfort. Built in 1993 and thoughtfully designed for multi-generational living and refined entertainment, the home offers generous space,

  Carmela Lopez Borrazas Serhant LLC

  16 Sunset Ridge, Monroe, NY 10950
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  /50

  $370,000

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

  3815 Whispering Hills Dr, Chester, NY 10918

  Discover your new haven at this charming 3-bedroom, 2.5-bathroom condo nestled in the vibrant community of Chester, NY. Perfect for those looking to infuse a home with their personal style, this residence offers fantastic potential to make it your own. Let your imagination take the reins and make this spacious house into your dream home! The condo is thoughtfully designed with ample room for rest

  David Kraus MK Realty Inc

  3815 Whispering Hills Dr, Chester, NY 10918
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  /5

  $54,900

  $10K PRICE DROP

  • 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

  $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
• 

  

  /49

  $400,000

  Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 1,699 Sq Ft

  174 Eagleton Dr Unit 17D, Monroe, NY 10950

  Welcome to this beautifully maintained end-unit townhouse offering serene lakefront living and an exceptional array of community amenities, including a pool, playground, basketball & tennis courts. Freshly painted throughout the first floor and enhanced with elegant crown molding, this home showcases quality finishes and pride of ownership. Attractive vinyl plank flooring extends through the

  Donna Gennaro Howard Hanna Rand Realty

  174 Eagleton Dr Unit 17D, Monroe, NY 10950
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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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  /23

  $390,000

  • 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
• 

  

  /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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  /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

  Frank Golio Howard Hanna Rand Realty

  651 Lakes Rd, Monroe, NY 10950
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  /48

  $1,299,900

  New Construction $150K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 4,508 Sq Ft

  145 Kings Highway Bypass, Chester, NY 10918

  Set gracefully on 3.8 private acres within the highly coveted Warwick School District, this exceptional custom home offers a rare blend of architectural elegance and refined living. Surrounded by a collection of equally distinguished residences, the property provides an expansive, park-like sanctuary while remaining nestled in the heart of one of the region’s most sought-after communities.

  Courtney Tablante Keller Williams Realty

  145 Kings Highway Bypass, Chester, NY 10918
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  /47

  $650,000

  $40K PRICE DROP

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

  10 Hidden Dr, Monroe, NY 10950

  Tucked away on over an acre with serene lake views and deeded lake rights, this spacious Monroe retreat offers the perfect blend of privacy, comfort, and lifestyle. Wake up to natural light pouring through oversized windows and start your day on the deck overlooking the water. Inside, you’ll find 4 generously sized bedrooms and 3 full baths, along with an updated kitchen and baths that bring a

  rosemary mcginn Century 21 Full Service Realty

  10 Hidden Dr, 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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  /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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  /9

  $79,995

  • Land
  • 20.26 Acres
  • $3,948 per Acre

  1.2 Cobble Creek Rd Unit 2, Chester, NY 12853

  Escape to the mountains with this beautiful 20-acre property in Chester, NY, ideally situated along a year-round maintained town road. The terrain gently climbs from the road, leading to multiple APA-approved building sites for an off-grid cabin or hunting camp offering excellent privacy in a quiet woodland setting. The property features a healthy forest of Northern hardwoods including maple,

  Marc Christmas CHRISTMAS AND ASSOCIATES INC

  1.2 Cobble Creek Rd Unit 2, Chester, NY 12853
• 

  

  /50

  $1,195,000

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

  19 High St, Chester, NY 10918

  Own a true piece of history with the iconic Hambletonian House, a one-of-a-kind Victorian estate built in the 19th century by William Rysdyk, original owner of Hambletonian 10—the legendary sire that shaped nearly all modern Standardbred racehorses. Perfectly positioned on nearly three private acres atop a knoll in the heart of Chester, New York, this meticulously maintained property offers a

  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
• 

  

  /43

  $430,000

  $20K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,177 Sq Ft

  151 Laroe Rd, Chester, NY 10918

  What a remarkable property in the town of Chester, NY-a highly sought after town in the southern Hudson Valley, only 45 minutes from the GW Bridge! This 3 bedroom, 2 bathroom house boasts tons of modern and energy efficient features. A massive renovation done only 5 years ago leaves you with nothing to maintain except to pick your paint colors and finishes. 1st floor main bedroom and additional

  Todd Sullivan Keller Williams Realty

  151 Laroe Rd, Chester, NY 10918
• 

  

  /25

  $159,000

  $6K PRICE DROP

  • Land
  • 31,798 Sq Ft
  • $217,808 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
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  /9

  $210,000

  • Land
  • 7.9 Acres
  • $26,582 per Acre

  41 Bull Mine Rd, Chester, NY 10918

  Explore 7.9 acres of vacant land with road frontage on Bull Mine Road. Situated within a filed subdivision approved in 2010, this wooded parcel offers a peaceful setting and convenient access to local amenities and commuter routes. For those seeking additional acreage, the adjoining 8.9-acre parcel on Catherine Court is also available for purchase-thus creating a combined offering of

  Michelle Getty HVG Realty, Inc.

  41 Bull Mine Rd, Chester, NY 10918
• 

  

  /13

  $206,000

  $69K PRICE DROP

  • 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
• 

  

  /47

  $825,000

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

  45 Whitetail Run, Chester, NY 10918

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

  Melissa Forsyth Hudson Valley Home Connection

  45 Whitetail Run, Chester, NY 10918
• 

  

  /49

  $769,000

  $31K PRICE DROP

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

  58 Nancy Ln, Chester, NY 10918

  Price improvement! Wait until you see all this home has to offer! Perched atop the desirable Fieldcrest subdivision with sweeping panoramic views and unforgettable sunsets, this spectacular Colonial offers exceptional space, comfort, and versatility both inside and out. Set on 1.3 picturesque acres, this beautifully maintained home is designed for everyday living and effortless entertaining.A

  Gina Dudgeon Howard Hanna Rand Realty

  58 Nancy Ln, Chester, NY 10918
• 

  

  /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
• 

  

  /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

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 $646,503.

Are home prices dropping in Chester?

Yes, home prices in Chester are down 6% in the last 12 months.

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

86 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, 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 $585,000. If you put a 20% down payment of $117,000 and had a 30-year fixed mortgage with an interest rate of 6.47%, your estimated principal and interest payment would be $2,950 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $126K 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 Greenwood Lake 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 $486,500, down 7% year-over-year. Homes in Chester sell in 60 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price $486,500	Median Single Family Sale Price $657,500
Median Townhouse Sale Price $320,000	Median 2 Bedroom Sale Price $310,000
Average Price Per Sq Ft $274	Number of Homes for Sale 52
Last 12 months Home Sales 86	Months of Supply 7.30
Median List Price $585,000	Median Change From 1st List Price 1%
Median Home Sale Price YoY Change -7%