Newest Homes for Sale in Chester, NY

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  /2

  $725,000

  • 3 Beds
  • 2.5 Baths
  • 2,677 Sq Ft

  1 Arborvitae 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 9 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

  1 Arborvitae Ct, Chester, NY 10918
• Explore Chester

• 

  

  /2

  $740,000

  • 5 Beds
  • 2.5 Baths
  • 2,700 Sq Ft

  7 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 9 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

  7 Hilltop Ln, Chester, NY 10918
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  /44

  $649,999

  Open Sat 12PM - 2PM

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

  424 Laroe Rd, Chester, NY 10918

  Welcome to 424 Laroe Road in Chester, a move-in–ready home that blends classic Hudson Valley charm with thoughtful updates. A bright main level offers a comfortable living area, dedicated dining space, and a well-appointed kitchen with ample storage and workspace. Upstairs, well-proportioned rooms provide flexible layouts for sleeping, a home office, or hobbies. Refreshed baths feature clean,

  Jeffrey Morrissey Epique Realty

  424 Laroe Rd, Chester, NY 10918
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  /2

  $1,700,000

  • Land
  • 46.5 Acres
  • $36,559 per Acre

  0 Route 94 Unit KEY1023037, Blooming Grove, NY 10914

  Incredible opportunity to own approximately 55 acres of land being offered as a package with two adjoining parcels. This expansive property offers endless potential for investors, builders, or those seeking a private estate or recreational retreat. Preliminary information suggests the property may have the potential for approximately 400,000 square feet of warehouse space. Both parcels are being

  Lazar Schvimmer Mount Realty

  0 Route 94 Unit KEY1023037, Blooming Grove, NY 10914
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  /46

  $635,000

  Open Sun 2PM - 4PM

  • 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 3/4 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
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  /34

  $349,999

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

  3414 Whispering Hills, Chester, NY 10918

  Welcome home to this beautifully updated 3-bedroom, 2-bathroom condominium with a 1-car garage, perfectly situated in the highly sought-after Whispering Hills community. Offering modern upgrades, spacious living, and resort-style amenities, this home is truly move-in ready. Step inside to discover a bright, open floor plan featuring gleaming hardwood floors, an updated chef-inspired kitchen with

  Kevin Grier KW Hudson Valley United

  3414 Whispering Hills, Chester, NY 10918
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  /44

  $489,900

  Open Sat 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,912 Sq Ft

  76 Surrey Rd, Chester, NY 10918

  Welcome to 76 Surrey Road, Chester, NY—a beautifully renovated ranch that is truly move-in ready. This turnkey home offers 3 bedrooms, 2 full bathrooms, and a thoughtfully designed layout filled with abundant natural light. The interior features a modern kitchen with granite countertops, updated finishes, and an open, inviting feel that's perfect for both everyday living and entertaining. The

  

  Ammar Iqbal

  eXp Realty

  76 Surrey Rd, 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

  Unlisted Address
• 

  

  /14

  $129,000

  $30K PRICE DROP

  • Land
  • 20,473 Sq Ft
  • $274,468 per Acre

  L31 Clarkson Rd, Chester, NY 12817

  Build Your Adirondack Getaway on Loon Lake!Enjoy beach rights on beautiful Loon Lake with this just-under-half-acre lot, the perfect spot to create your own year-round retreat or seasonal escape. Whether you dream of summer days by the water, paddling and swimming, or cozy winter weekends in the mountains, this property offers an ideal starting point for your Adirondack lifestyle.

  Brooke Clark Four Seasons Sotheby's International Realty

  L31 Clarkson Rd, Chester, NY 12817
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  /32

  $615,000

  Open Sun 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 1,908 Sq Ft

  11 Chandler Dr, Chester, NY 10918

  Welcome to this beautifully maintained raised ranch, perfectly situated on a desirable corner lot in Chester. This inviting 3-bedroom, 2 full and 1 half bath home blends comfort, style, and modern convenience in a location you'll love. Filled with natural light, the home features spacious living areas and a well-appointed kitchen with stainless steel appliances. The finished basement offers

  Daniella Restrepo Coldwell Banker Realty

  11 Chandler Dr, Chester, NY 10918
• 

  

  /22

  $329,000

  Open Sun 12PM - 2PM

  • 2 Beds
  • 1.5 Baths
  • 1,294 Sq Ft

  4118 Whispering Hills, Chester, NY 10918

  Beautifully maintained two bedroom condo with a two car garage in an excellent location within the highly desirable Whispering Hills community. Updated kitchen and newer flooring on the main level. Wood burning fireplace in the spacious living room. Sliding door from the dining area to the patio. The primary bedroom with tall vaulted ceilings has a large walk-in closet with custom

  

  Joseph Paoli

  Howard Hanna Rand Realty

  4118 Whispering Hills, Chester, NY 10918
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  /42

  $559,000

  Open Sat 1:30PM - 3:30PM

  • 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 move-in ready and waiting for its next chapter.Step inside to a bright and inviting floor

  Claudia Lepore Keller Williams Realty

  44 Wilson Rd, Monroe, NY 10950
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  /47

  $579,000

  Open Sun 11AM - 1PM

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

  152 Highland Ave, Monroe, NY 10950

  Impeccably maintained and lovingly cared for, this spacious 3-bedroom, 2-bath , 48 foot bi-level ranch offers comfort, functionality, and timeless appeal in one of Monroe’s desirable private cul-de-sac settings.Step inside to find bright, welcoming living spaces, generous room sizes, and beautiful hardwood floors that add warmth and character throughout much of the home. The inviting main

  Aja Marshall Krumpfer Realty Group, LLC

  152 Highland Ave, Monroe, NY 10950
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  /5

  $850,000

  • 5 Beds
  • 2.5 Baths
  • 3,200 Sq Ft

  5 Hilltop Ln, Chester, NY 10918

  Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new colonial-style residence invites you in with 12 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 kitchen. Every detail

  Moshe Kaufman MK Realty Inc

  5 Hilltop Ln, Chester, NY 10918
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  /36

  $800,000

  Open Sat 12PM - 2PM

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

  985 Craigville Rd, Chester, NY 10918

  Welcome to your own private retreat, where timeless design, exceptional outdoor living, and over three acres of peaceful surroundings come together to create an unforgettable place to call home.Inside, the heart of the home is anchored by a stunning double sided fireplace that effortlessly connects the main living areas, creating warmth, character, and an inviting atmosphere for both everyday

  DAVID DEBERARDINIS Serhant LLC

  985 Craigville Rd, Chester, NY 10918
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  /4

  $750,000

  • 5 Beds
  • 2.5 Baths
  • 2,700 Sq Ft

  3 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 9 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

  Dovid Hoffman MK Realty Inc

  3 Boville Ct, Chester, NY 10918
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  /32

  $295,000

  • 2 Beds
  • 1.5 Baths
  • 1,086 Sq Ft

  2119 Whispering Hills, Chester, NY 10918

  Step into this gorgeous Townhouse.Upon entering you’ll be welcomed by a perfect floor plan. The inviting living room features wooden floors, a cozy fireplace, and windows. The stylish kitchen has a functional layout and is outfitted with stainless steel appliances and granite countertops. The master-bedroom offers a modern feel and a walk in closet. Enjoy the amenity centers. Stop dreaming and

  Jasmine Wadhwa Howard Hanna Rand Realty

  2119 Whispering Hills, Chester, NY 10918
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  /39

  $799,900

  Open Sun 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 2,715 Sq Ft

  176 Beverly Rd, Chester, NY 10918

  Welcome to 176 Beverly Road, Colonial-style nestled on 2.5 beautifully landscaped acres in the highly sought-after Warwick Valley School District. From the moment you arrive, you'll appreciate the home's curb appeal featuring custom stone entrance pillars with illuminated house numbers, a beautifully inlaid driveway address, professionally landscaped grounds accented by natural stone and

  Jocelyn Rivera

  176 Beverly Rd, Chester, NY 10918
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  /48

  $400,000

  • 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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  /3

  $150,000

  • Land
  • 5.14 Acres
  • $29,183 per Acre

  36 Fawn Ridge Rd, Chester, NY 12817

  Must see building site which has panoramic views overlooking Gore Mountain Range to the North but possible 360 degree Mountain View's with some clearing necessary.

  John Palermo John R. Palermo

  36 Fawn Ridge Rd, Chester, NY 12817
• 

  

  /50

  $440,800

  • 3 Beds
  • 1 Bath
  • 2,016 Sq Ft

  815 Craigville Rd, Chester, NY 10918

  We are proud to introduce this cornerstone property, located within what was once a thriving enclave of artists. The same owner since 1946, this home and studio are part of a small collection of historic properties that helped define the character of the area. Now, an extraordinary opportunity awaits for the next steward to write the next chapter of this remarkable property.Originally built

  MaryBeth O'Hara Ellis Sotheby's Intl Realty

  815 Craigville Rd, Chester, NY 10918
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  /37

  $789,900

  Open Sun 12PM - 3PM

  • 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
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  /35

  $849,999

  $30K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,236 Sq Ft

  24 Boville Ct, Chester, NY 10918

  Welcome to 24 Boville Court that sits on 3.7 acres a beautifully maintained home perfectly positioned on a quiet cul-de-sac in the highly desirable Town of Chester. Nestled on a premium end corner lot that extends all the way to Route 94, this exceptional property offers the perfect blend of privacy, comfort, and convenience.Step inside to discover bright, inviting living spaces, generously

  Jennifer Acevedo KW Hudson Valley United

  24 Boville Ct, Chester, NY 10918
• 

  

  /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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  /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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  /50

  $1,195,000

  • 4 Beds
  • 3.5 Baths
  • 4,281 Sq Ft

  22 Goshen Rd, Chester, NY 10918

  Welcome to an unparalleled expression of luxury living in the Town of Chester. Built in 2003, this custom-built Cape May/Colonial estate designed by award winning architect Larry Belk estate spans 4,281 square feet of meticulously designed living space, masterfully balancing grand entertaining spaces with intimate everyday comfort. From the moment you arrive, exceptional craftsmanship is on

  Martha Randazzo Howard Hanna Rand Realty

  22 Goshen Rd, Chester, NY 10918
• 

  

  /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
• 

  

  /10

  $119,995

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

  1.3 Cobble Creek Rd Unit 3, 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 INC

  1.3 Cobble Creek Rd Unit 3, Chester, NY 12853
• 

  

  /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

  1 Oakland Ave, Chester, NY 10918
• 

  

  /35

  $875,000

  • 4 Beds
  • 2.5 Baths
  • 3,656 Sq Ft

  49 Stone Mountain Trail, Chester, NY 10918

  Escape to your own private retreat at 49 Stone Mountain Trail. Tucked away on more than 7 acres with mountain views, this contemporary home delivers the perfect balance of comfort, space, and outdoor enjoyment. Imagine mornings filled with sunlight streaming through oversized windows, evenings gathered around the stone fireplace, and summers spent relaxing by the in-ground pool surrounded by

  Arya Rabinovits eRealty Advisors, Inc

  49 Stone Mountain Trail, Chester, NY 10918
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  /33

  $185,000

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft

  28 Olmstedville Rd, Chester, NY 12817

  Older home in a completely private location - in the center of a Hamlet. Trees and bushes make the home invisible from the road. The back border is Town land with Public beach area on Trout Brook Good for canoeing. Covered porch is on two sides of the house. The interior has beautiful real wood floors. Main level is kitchen, dining room, living room, full bath and laundry area. Upstairs are 3

  Heidemarie Lane Big Hat Realty

  28 Olmstedville Rd, Chester, NY 12817
• 

  

  /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
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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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  /29

  $685,000

  $35K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,718 Sq Ft

  26 Bridle Ln, Chester, NY 10918

  From the moment you arrive, it's clear this is a home whose character and setting are best experienced firsthand. The bright, open-concept living area features vaulted ceilings and abundant natural light, creating an inviting space for everyday living and entertaining. A beautiful den with two walls of windows and a gas fireplace overlooks the pool and surrounding landscape. The thoughtfully

  David White Owner Entry.com

  26 Bridle Ln, Chester, NY 10918
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  /29

  $549,900

  • 3 Beds
  • 2 Baths
  • 2,138 Sq Ft

  3318 State Route 94, Chester, NY 10918

  This beautifully updated homes features wood floors throughout, three spacious bedrooms, two den/office spaces, formal dining room, and two full baths. The expansive primary suite has an additional 10 X 10-ft. sitting room, generous walk-in closet, an en-suite with linen closet, walk-in shower and Venetian soaking tub. The main floor bathroom is equally large with a jetted bathtub. Both the

  Asha Keegan Howard Hanna Rand Realty

  3318 State Route 94, Chester, NY 10918
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  /43

  $949,000

  • 4 Beds
  • 2.5 Baths
  • 3,332 Sq Ft

  19 Bull Mine Rd, Chester, NY 10918

  Set on 2.3 acres in Chester, this impressive property offers space, versatility, and scenic surroundings. The residence features approximately 3,332 square feet of living space with 4 bedrooms, 2 full baths and 1 half bath, thoughtfully designed for comfortable everyday living and entertaining. Interior highlights include generously sized living areas, a fireplace, abundant natural light, and

  James Cosenza BHG Real Estate Green Team

  19 Bull Mine Rd, Chester, NY 10918
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  /35

  $675,000

  $40K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,784 Sq Ft

  335 Laroe Rd, Chester, NY 10918

  Set on 3.2 acres within the Monroe-Woodbury School District, 335 Laroe Road offers a rare combination of space, functionality, and a convenient Chester location. Step inside to the welcoming two-story foyer featuring an open staircase and you'll immediately appreciate the size of the home. The main level offers a functional layout with multiple living spaces, including a living room, formal

  Christina D'Altiiio Coldwell Banker Choice Prop.

  335 Laroe Rd, Chester, NY 10918
• 

  

  /36

  $419,000

  Open Sun 12PM - 2PM

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

  332 Heritage Ln, Monroe, NY 10950

  Spacious and well-maintained 3BR/2.5BA townhouse in desirable Windridge community. Features include updated laminate hardwood flooring, fireplace, eat-in kitchen, stainless steel appliances, private balcony off primary bedroom, sliding glass doors to private patio, attached 1-car garage with storage loft, and pull-down attic access. Community amenities include pool, clubhouse, and park.

  Martin Remo RE/MAX Prime Properties

  332 Heritage Ln, Monroe, NY 10950
• 

  

  /23

  $99,995

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

  1.4 Cobble Creek Rd, 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

  1.4 Cobble Creek Rd, Chester, NY 12853
• 

  

  /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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