Newest Homes for Sale in Chester, NY

• 

  

  

  /10

  $99,995

  • Land
  • 22.88 Acres
  • $4,370 per Acre

  1.4 Cobble Creek Rd Unit 4, Chester, NY 12853

  Experience the best of Adirondack living on this scenic 22-acre property in Chester, New York. Accessible year-round from a town-maintained road with power nearby, the land offers several elevated APA-approved building sites perfectly positioned for a private cabin, vacation home, or full-time residence. The property is richly forested with mature Northern hardwoods including maple, oak, birch,

  Marc Christmas CHRISTMAS AND ASSOCIATES INC

  1.4 Cobble Creek Rd Unit 4, Chester, NY 12853
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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
• 

  

  

  /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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  /49

  $999,900

  $200K PRICE DROP

  • 4,032 Sq Ft

  206 Greycourt Rd, Chester, NY 10918

  INCREDIBLE PROPERTY!!! MUNICIPAL WATER!!! MONROE WOODBURY SCHOOL DISTRICT!!! Welcome to 206 Greycourt Road, Chester, NY A truly rare and remarkable offering in the heart of Orange County, Presenting an extraordinary opportunity to acquire a standout property with exceptional visibility, flexible “ OP” zoning, multiple structures, and limitless potential. Positioned on one of Chester's most highly

  Frank Muccari Cronin & Company Real Estate

  206 Greycourt Rd, Chester, NY 10918
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  /26

  $275,000

  • 2 Beds
  • 1 Bath
  • 1,062 Sq Ft

  804 Swan Hollow Rd, Monroe, NY 10950

  Welcome Home! Well maintained two bedroom unit with lake and mountain views. Spacious living room with access to a private balcony. Eat in kitchen has updated counter tops and new appliances. Both bedrooms have ample closet space. Windridge is a quiet community conveniently located minutes from town. Great commuter location. Amenities include pool, playground, tennis and basketball courts,

  Valerie Quinn Keller Williams Realty

  804 Swan Hollow Rd, Monroe, NY 10950
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  /48

  $899,000

  $86K PRICE DROP

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

  86 Long Vista Ln, Chester, NY 10918

  Now offered at $899,000. Settle in before the new school year and start living your best life here. Privately set on over 5 scenic acres within the Warwick School District and just one hour from Manhattan, this beautifully maintained Colonial offers the lifestyle buyers are searching for. Privacy, acreage, breathtaking mountain views, resort-style outdoor living, flexible space, and a convenient

  

  Jennifer DiCostanzo

  RE/MAX Town & Country

  86 Long Vista Ln, Chester, NY 10918
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  /49

  $1,090,000

  • 4 Beds
  • 3.5 Baths
  • 4,130 Sq Ft

  102 Beverly Rd, Chester, NY 10918

  Located in the Warwick School district on a coveted street sits this larger than life home with impressive presence. The curved driveway welcomes you to the wide porch, perfect for rocking chairs and relaxing. The impressive entrance with custom stairway and window seat is just the first of impressive touches in this home. Large kitchen overlooks the yard and is well appointed with Thor

  Kimberly Corkum Keller Williams Realty

  102 Beverly Rd, Chester, NY 10918
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  /9

  $275,000

  • Land
  • 7.53 Acres
  • $36,521 per Acre

  L1.34 McPhillips Pine Ln, Chester, NY 12817

  If you are looking for an ultra private lot with access (dock and beach rights) to one of the pristine exclusive lakes in the Adirondacks, you found it. Friends Lake is the home to cool people and is private, jet-ski free, with a water ski course and simply no nonsense. Only 2O minutes to Lake George and Gore Mountain Ski Area. About 4 hours from NYC and 2.5 hours to Montreal. Saratoga Springs is

  Michael Lynch Coldwell Banker Prime Properties

  L1.34 McPhillips Pine Ln, Chester, NY 12817
• 

  

  /23

  $550,000

  $40K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,083 Sq Ft

  94 Booth Rd, Chester, NY 10918

  Some lots just have good bones. This one has it's own private nature trail, stocked pond rights, and a cul-de-sac that dead-ends into miles of nature trails anchored by a solid, spacious raised ranch on 1.8 acres. Inside, the home has been partially updated and offers solid bones with room to add your own touch over time. The house delivers where it counts. Three bedrooms, two and a half baths,

  Craig Watters Compass Greater NY, LLC

  94 Booth Rd, Chester, NY 10918
• 

  

  /16

  $65,000

  • Land
  • 1 Acre
  • $65,000 per Acre

  888 Landon Hill Rd, Chester, NY 12817

  One acre building lot. Property is cleared for building, 200 amp electric service installed and a point well on the property. There is currently a 14x40 ''tiny home'' on the property that can be purchased separately or the seller will remove. Minutes from Pottersville, close to Chestertown and Schroon Lake. Appx 20 mins to Gore Mnt Ski Center, 15 mins to Schroon Lake and only 10 mins from Loon

  Kelli May Better Way Realty

  888 Landon Hill Rd, Chester, NY 12817
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  /28

  $559,000

  $21K PRICE DROP

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

  24 Walnut St, Chester, NY 10918

  Welcome to 24 Walnut Street, Flexibility, Space & Endless Possibility in the Heart of Chester, NYTucked on a generous half-acre lot in the charming Village of Chester, this versatile 4-bedroom, 2.5-bath home offers a rare mother-daughter layout that delivers the best of both worlds, income potential, or simply more space to grow. Set on a quiet, tree-lined street just minutes from the Orange

  Tara Roufanis Keller Williams Village Sq Rlt

  24 Walnut St, Chester, NY 10918
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  /49

  $785,000

  $14K PRICE DROP

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

  4 Debbie Ct, Chester, NY 10918

  Welcome to this exceptional private retreat nestled on beautifully landscaped grounds in desirable Chester. Offering the perfect blend of space, comfort, privacy, and lifestyle, this impressive property is surrounded by natural beauty while remaining conveniently close to shopping, dining, major highways, and the scenic Stewart State Forest. From the moment you arrive, you’ll appreciate the

  Joseph Rosenfeld Flag Realty Group

  4 Debbie Ct, Chester, NY 10918
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  /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
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  /25

  $125,000

  • Land
  • 13.33 Acres
  • $9,377 per Acre

  L9 Byrd Pond, Chester, NY 12853

  Open walking trail around the property and very easy to navigate. Private 13+ acre building parcel just minutes from Gore Mountain and the conveniences of North Creek. The land is gently sloping with a roughed-in driveway/road already leading in from Bird Pond Road, offering a great head start for future access and site planning. Several attractive building locations can be found throughout the

  Walter Swartz Gallo Realty ADK Inc

  L9 Byrd Pond, Chester, NY 12853
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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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  /7

  $900,000

  • 4 Beds
  • 2.5 Baths
  • 2,588 Sq Ft

  60 Whitetail Run, Chester, NY 10918

  Beautifully maintained Colonial set on a picturesque and private property offering the perfect blend of comfort, space, This spacious home features an inviting layout with generously sized rooms, hardwood flooring, elegant moldings, and abundant natural light throughout. The heart of the home is the oversized eat-in kitchen with granite countertops, extensive cabinetry, pantry space, and

  Isaac Rottenberg Realty Blue Corp

  60 Whitetail Run, 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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  /20

  $894,000

  $105K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 3,535 Sq Ft

  220 Oxford Rd, Chester, NY 10918

  220 Oxford Road is a Truly Impressive Property! Offering over 3,500 sq ft of beautifully maintained living space, this home features 3 bedrooms plus an additional upper-level room, 3 full baths, and 1 half bath. Spacious living room, stunning family room, and a practical, well-designed kitchen. The home showcases elegant finishes throughout along with brand new flooring that adds a fresh modern

  Moche Halpern Blooming Realty

  220 Oxford Rd, Chester, NY 10918
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  /35

  $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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  /45

  $499,000

  $30K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,060 Sq Ft

  63 Hubshop Rd, Chester, NY 10918

  Nestled on a quiet road off the beaten path, this serene 4-bedroom, 2.5-bathroom Colonial offers the perfect blend of secluded tranquility and commuter convenience. The main level features a traditional layout with a spacious living room, formal dining room, and a cozy recreation room perfect for relaxing. The functional eat-in kitchen serves as the heart of the home, while all four bedrooms are

  Charles Moore Keller Williams Realty

  63 Hubshop Rd, Chester, NY 10918
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  /50

  $749,999

  $50K PRICE DROP

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

  58 Nancy Ln, Chester, NY 10918

  Imagine ending everyday watching the sun set from your front porch, experiencing views that change with every season. Sunset views, fenced yard, brand new Trex deck, pool, home office and room for four sleeping spaces make this the perfect property. Perched at the top of the highly sought-after Fieldcrest subdivision, this stunning Colonial captures breathtaking panoramic views and unforgettable

  Gina Dudgeon Howard Hanna Rand Realty

  58 Nancy Ln, 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 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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  /50

  $3,400,000

  • 4 Beds
  • 4 Baths
  • 7,750 Sq Ft

  19 Greentree Ln, Chester, NY 10918

  Set behind a gated entrance with a private guard house and unfolding across 8.4 private acres, The Retreat at Greentree is a true estate in every sense, engineered for privacy, designed for lifestyle, and positioned as one of the most unique offerings in the Hudson Valley. A cascading waterfall greets you on arrival, establishing a sense of calm and separation from the outside world. From that

  Jake Garay Serhant LLC

  19 Greentree Ln, Chester, NY 10918
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  /42

  $849,900

  • 4 Beds
  • 3 Baths
  • 2,370 Sq Ft

  2 Primrose Ln, Chester, NY 10918

  Welcome to this stunning Colonial, perfectly blending comfort, style, and functionality. Offering 2,370 sq ft plus full walkout basement, this beautifully designed home features 4 spacious bedrooms and 3 full bathrooms, creating an inviting layout ideal for everyday living and entertaining.Step inside to a grand, sun-filled foyer with soaring ceilings that set the tone for the home’s warm and

  Janet Rendle Weichert Realtors

  2 Primrose Ln, Chester, NY 10918
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  /29

  $489,900

  $60K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,032 Sq Ft

  35 Maple Ave, Chester, NY 10918

  Welcome to 35 Maple Avenue, a bright 3 bedroom, 3 full bath Raised Ranch in the desirable Village of Chester ideally located near the Village Park & School. This spacious 2,032 sq. ft. residence built in 2002 & Updated in 2020 including bathrooms & New Kitchen in 2024. The open main level features a White EIK with Quartz Counters & Island, stylish white tile backsplash, Pantry, Black Appliances,

  Joanne Timperio RE/MAX Benchmark Realty Group

  35 Maple Ave, Chester, NY 10918
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  /46

  $799,900

  $88K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,740 Sq Ft

  149 Creamery Pond Rd, Chester, NY 10918

  Welcome to the highly sought-after Creamery Estate, located in the award-winning Warwick school district!. This inviting waterfront Colonial-style home offers the perfect blend of comfort, charm, and scenic beauty, set on an acre of beautifully maintained grounds with peaceful views of Creamery Pond. This 3-bedroom, 3 full bath home features hardwood floors throughout and a spacious, easy-flow

  Carla Terranova Keller Williams Realty

  149 Creamery Pond Rd, Chester, NY 10918
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  /50

  $623,900

  $125K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,524 Sq Ft

  17 Woodridge Dr, Chester, NY 10918

  Beautiful Colonial set on just under an acre of meticulously landscaped property, offering breathtaking sunset views from a very private backyard. The taxes may be reduced by up to 20%; however, a tax appeal cannot be filed until 2027. Great spacious front porch! On a quiet cul-de-sac, this home features a stunning in-ground pool with a new heater, cover & pump. Pool filter, and liner are about 4

  Sharon Kushner eXp Realty

  17 Woodridge Dr, Chester, NY 10918
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  /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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  /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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  /48

  $1,299,900

  New Construction Open Sun 11AM - 1PM $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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  /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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  /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

  $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
• 

  

  /45

  $535,000

  $55K 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
• 

  

  /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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  /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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  /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
• 

  

  /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
• 

  

  /8

  $869,900

  New Construction

  • 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
• 

  

  /50

  $599,000

  Open Sun 1PM - 2PM $251K PRICE DROP

  • 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

Showing Results 41 - 80, Page 2 of 3