5,275

Homes in ZIP Code 10918

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  • 1 N Hudson St Unit N, Chester, NY 10918
    1 N Hudson St Unit N, Chester, NY 10918
    1 N Hudson St Unit N, Chester, NY 10918
    /38

    $499,900

    Pending
    • 3 Beds
    • 2 Baths
    • 1,778 Sq Ft

    1 N Hudson St Unit N, Chester, NY 10918

    Welcome home to 1 North Hudson Street — a meticulously maintained Cape Cod that is truly beautiful inside and out. From the moment you arrive, the curb appeal speaks for itself. Lush, manicured grounds frame this charming brick and white-sided Cape Cod, where mature trees, vibrant landscaping, and a stunning bluestone patio set the stage for a lifestyle of comfort and ease. Whether you're hosting

    Agent Photo

    Alison Orlando

    KW Hudson Valley Untied

    (845) 407-8986

    1 N Hudson St Unit N, Chester, NY 10918
  • 1403 Kings Hwy, Chester, NY 10918
    1403 Kings Hwy, Chester, NY 10918
    1403 Kings Hwy, Chester, NY 10918
    /43

    $3,750 Per Month

    • 3 Beds
    • 2.5 Baths
    • 3,200 Sq Ft
    • Apartment for Rent

    1403 Kings Hwy, Chester, NY 10918

    Luxury Farmhouse Rental in the Heart and Soul of Sugar Loaf – Warwick Schools! Experience country luxury at its finest in this stunning farmhouse rental located in the charming hamlet of Sugar Loaf. Designed for those who appreciate quality craftsmanship and timeless character, this exceptional home offers approximately 3,200 square feet of beautifully appointed living space. Step inside to

    Carla Terranova Keller Williams Realty

    1403 Kings Hwy, Chester, NY 10918
  • 242 Meadow Ave, Chester, NY 10918

    $225,000

    Sold Jun 30, 2025

    242 Meadow Ave, Chester, NY 10918

    • 4 Beds
    • 3 Baths
    • 2,519 Sq Ft
    • Built 1930

    Last Sold Summary

    • $89/SF
    • 56 Days On Market

    Current Estimated Value $348,000

    Last Listing Agent Kathleen Strong Hudson Valley Griffith

    242 Meadow Ave, Chester, NY 10918
    • 20 High St, Chester, NY 10918

      Est $487,249

      Not Listed For Sale

      20 High St, Chester, NY 10918

      • 3 Beds
      • 2 Baths
      • 2,488 Sq Ft
      • Built 1825
      20 High St, Chester, NY 10918

      Last Sold Summary

      • 35 Days On Market

  • 0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
    0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
    0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
    /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.

    Agent Photo

    Theresa Powers

    Keller Williams Realty

    (845) 713-9754

    0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
  • 39 Shore Dr, Blooming Grove, NY 10914
    39 Shore Dr, Blooming Grove, NY 10914
    39 Shore Dr, Blooming Grove, NY 10914
    /72

    $395,000

    Sold Mar 17, 2026

    39 Shore Dr, Blooming Grove, NY 10914

    • 2 Beds
    • 2.5 Baths
    • 2,282 Sq Ft
    • Built 1965

    Last Sold Summary

    • 29% Below List Price
    • $173/SF
    • 120 Days On Market

    Current Estimated Value $469,792

    Last Listing Agent Nicola Friedman Windsor Realty Services, Inc.

    39 Shore Dr, Blooming Grove, NY 10914
    • 221 Oxford Rd, Chester, NY 10918

      Est $984,623

      Not Listed For Sale

      221 Oxford Rd, Chester, NY 10918

      • 4 Beds
      • 3.5 Baths
      • 4,644 Sq Ft
      • Built 2000
      221 Oxford Rd, Chester, NY 10918

      Last Sold Summary

      • 132 Days On Market

  • 9 Derose Ln, Chester, NY 10918
    9 Derose Ln, Chester, NY 10918
    9 Derose Ln, Chester, NY 10918
    /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
  • 12 Bianca Blvd, Chester, NY 10918

    $575,000

    Sold Sep 23, 2025

    12 Bianca Blvd, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 3,200 Sq Ft
    • Built 1987

    Last Sold Summary

    • 2% Below List Price
    • $180/SF
    • 126 Days On Market

    Current Estimated Value $653,625

    Last Listing Agent Aoife Freeman eXp Realty

    12 Bianca Blvd, Chester, NY 10918
    • 215 Ridge Rd, Chester, NY 10918

      Est $815,166

      Not Listed For Sale

      215 Ridge Rd, Chester, NY 10918

      • 3 Beds
      • 3 Baths
      • 3,005 Sq Ft
      • Built 1848
      215 Ridge Rd, Chester, NY 10918

      Last Sold Summary

      • 119 Days On Market

  • 39 Peddler Hill Rd, Monroe, NY 10950
    39 Peddler Hill Rd, Monroe, NY 10950
    39 Peddler Hill Rd, Monroe, NY 10950
    /30

    $660,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,987 Sq Ft

    39 Peddler Hill Rd, Monroe, NY 10950

    Welcome to your dream home in the heart of Monroe, NY—where modern elegance meets everyday convenience. This beautifully appointed 1,987 sq ft raised ranch offers a perfect blend of contemporary design, generous living space, and a prime location just one hour from New York City. With 3 spacious bedrooms, 2 updated bathrooms, and a layout crafted for both comfort and style, this home is ready to

    Jessica Evans KW Hudson Valley United

    39 Peddler Hill Rd, Monroe, NY 10950
  • 4508 Whispering Hills, Chester, NY 10918

    $300,000

    Sold Apr 20, 2026

    4508 Whispering Hills, Chester, NY 10918

    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft
    • Built 1987

    Last Sold Summary

    • 8% Below List Price
    • $280/SF
    • 44 Days On Market

    Current Estimated Value $301,889

    Last Listing Agent Ammar Iqbal eXp Realty

    4508 Whispering Hills, Chester, NY 10918
  • 3815 Whispering Hills Dr, Chester, NY 10918
    3815 Whispering Hills Dr, Chester, NY 10918
    3815 Whispering Hills Dr, Chester, NY 10918
    /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
  • 9 June Rd, Chester, NY 10918

    $620,000

    Sold Oct 29, 2025

    9 June Rd, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,402 Sq Ft
    • Built 1999

    Last Sold Summary

    • 4% Below List Price
    • $258/SF
    • 52 Days On Market

    Current Estimated Value $627,056

    Last Listing Agent Jason Madison eXp Realty

    9 June Rd, Chester, NY 10918
  • 63 Whitetail Run, Chester, NY 10918
    63 Whitetail Run, Chester, NY 10918
    63 Whitetail Run, Chester, NY 10918
    /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
  • 3708 Whispering Hills, Chester, NY 10918

    $310,000

    Sold Nov 10, 2025

    3708 Whispering Hills, Chester, NY 10918

    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft
    • Built 1990

    Last Sold Summary

    • 5% Above List Price
    • $289/SF
    • 26 Days On Market

    Current Estimated Value $311,601

    Last Listing Agent Nikki Grzegorzewski Keller Williams Realty

    3708 Whispering Hills, Chester, NY 10918
  • 33 Meadow Ave, Chester, NY 10918
    33 Meadow Ave, Chester, NY 10918
    33 Meadow Ave, Chester, NY 10918
    /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
  • 23 Renies Rd, Chester, NY 10918

    $644,000

    Sold Feb 12, 2026

    23 Renies Rd, Chester, NY 10918

    • 3 Beds
    • 3 Baths
    • 3,200 Sq Ft
    • Built 1990

    Last Sold Summary

    • 7% Below List Price
    • $201/SF
    • 100 Days On Market

    Current Estimated Value $675,208

    Last Listing Agent Kristie Jacques Century 21 Full Service Realty

    23 Renies Rd, Chester, NY 10918
  • 16 Oakland Ave, Chester, NY 10918
    16 Oakland Ave, Chester, NY 10918
    16 Oakland Ave, Chester, NY 10918
    /49

    $425,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,090 Sq Ft

    16 Oakland Ave, Chester, NY 10918

    Charming 4-Bedroom Colonial in the Heart of Hudson Valley. Priced to Sell, tons of potential and great commuter location with close proximity tohighway! Welcome to this spacious 4-bedroom, 2.5-bath home nestled in the picturesque town of Chester, NY, in the heart of the beautifulHudson Valley. Offering 2,090 sq ft of living space, plus a finished rec room with an additional 1,026 sq ft,

    Vikki Garby BHG Real Estate Green Team

    16 Oakland Ave, Chester, NY 10918
  • 27 Grand View Terrace, Chester, NY 10918

    $780,000

    Sold Aug 15, 2025

    27 Grand View Terrace, Chester, NY 10918

    • 5 Beds
    • 3.5 Baths
    • 4,490 Sq Ft
    • Built 2004

    Last Sold Summary

    • 3% Above List Price
    • $174/SF
    • 43 Days On Market

    Current Estimated Value $797,760

    Last Listing Agent Randolph Rogers eXp Realty

    27 Grand View Terrace, Chester, NY 10918
  • 2113 Whispering Hills Unit 178, Chester, NY 10918
    2113 Whispering Hills Unit 178, Chester, NY 10918
    2113 Whispering Hills Unit 178, Chester, NY 10918
    /24

    $275,000

    $20K PRICE DROP Pending
    • 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
  • 284 Bull Mill Rd, Chester, NY 10918

    $850,000

    Sold Oct 22, 2025

    284 Bull Mill Rd, Chester, NY 10918

    • 5 Beds
    • 3 Baths
    • 3,485 Sq Ft
    • Built 1997

    Last Sold Summary

    • $244/SF
    • 20 Days On Market

    Current Estimated Value $843,057

    Last Listing Agent Jayne M. Prechtel Keller Williams Valley Realty

    284 Bull Mill Rd, Chester, NY 10918
    • 509 Laroe Rd, Chester, NY 10918

      Est $651,615

      Not Listed For Sale

      509 Laroe Rd, Chester, NY 10918

      • 4 Beds
      • 3 Baths
      • 2,350 Sq Ft
      • Built 1981
      509 Laroe Rd, Chester, NY 10918

      Last Sold Summary

      • 50 Days On Market

  • 4 Oak St, Chester, NY 10918
    4 Oak St, Chester, NY 10918
    4 Oak St, Chester, NY 10918
    /42

    $499,900

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,888 Sq Ft

    4 Oak St, Chester, NY 10918

    SPRAWLING BRICK RANCH!!! VILLAGE OF CHESTER! ALMOST 1900 SQ. FT. ON THE MAIN LEVEL!!! X- LARGE 1/2 ACRE LOT!!! Welcome to 4 Oak Street, nestled in the charming Village of Chester, NY. Offered for the very first time, this exceptional home was custom built for its original owners and has been lovingly maintained ever since—a true testament to quality craftsmanship and pride of ownership. Set on a

    Frank Muccari Cronin & Company Real Estate

    4 Oak St, Chester, NY 10918
  • 1 Winding Trail, Chester, NY 10918

    $540,000

    Sold Aug 28, 2025

    1 Winding Trail, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 2,040 Sq Ft
    • Built 1991

    Last Sold Summary

    • 10% Below List Price
    • $265/SF
    • 35 Days On Market

    Current Estimated Value $551,038

    Last Listing Agent Donald Serotta Howard Hanna Rand Realty

    1 Winding Trail, Chester, NY 10918
  • 90 Pewter Cir, Chester, NY 10918
    90 Pewter Cir, Chester, NY 10918
    90 Pewter Cir, Chester, NY 10918
    /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
  • 411 Prospect Rd, Chester, NY 10918

    $610,000

    Sold Aug 25, 2025

    411 Prospect Rd, Chester, NY 10918

    • 4 Beds
    • 2 Baths
    • 1,987 Sq Ft
    • Built 1973

    Last Sold Summary

    • 2% Above List Price
    • $307/SF
    • 39 Days On Market

    Current Estimated Value $615,951

    Last Listing Agent Dana Posner Howard Hanna Rand Realty

    411 Prospect Rd, Chester, NY 10918
    • 118 Murray Dr, Chester, NY 10918

      Est $816,870

      Not Listed For Sale

      118 Murray Dr, Chester, NY 10918

      • 5 Beds
      • 4 Baths
      • 3,418 Sq Ft
      • Built 1978
      118 Murray Dr, Chester, NY 10918

      Last Sold Summary

      • 110 Days On Market

  • 35 Peddler Hill Rd, Monroe, NY 10950
    35 Peddler Hill Rd, Monroe, NY 10950
    35 Peddler Hill Rd, Monroe, NY 10950
    /23

    $650,000

    $49K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,260 Sq Ft

    35 Peddler Hill Rd, Monroe, NY 10950

    "High-Value Property – Exceptional Location, Endless Potential" Discover an exceptional investment opportunity in a highly sought-after area! This charming home sits on over half an acre of prime real estate, making it perfect for investors, builders, or anyone looking to secure a valuable asset. With its spacious lot and desirable location, this property promises not only immediate returns but

    Joseph Rosenfeld Flag Realty Group

    35 Peddler Hill Rd, Monroe, NY 10950
  • 11 Vista Dr, Chester, NY 10918

    $525,000

    Sold Jul 24, 2025

    11 Vista Dr, Chester, NY 10918

    • 4 Beds
    • 3 Baths
    • 2,122 Sq Ft
    • Built 1998

    Last Sold Summary

    • 2% Above List Price
    • $247/SF
    • 43 Days On Market

    Current Estimated Value $554,168

    Last Listing Agent James Feldhaus eXp Realty

    11 Vista Dr, Chester, NY 10918
    • 142 Laroe Rd, Chester, NY 10918

      Est $674,071

      Not Listed For Sale

      142 Laroe Rd, Chester, NY 10918

      • 5 Beds
      • 3.5 Baths
      • 3,385 Sq Ft
      • Built 1981
      142 Laroe Rd, Chester, NY 10918

      Last Sold Summary

      • 107 Days On Market

  • 145 Kings Highway Bypass, Chester, NY 10918
    145 Kings Highway Bypass, Chester, NY 10918
    145 Kings Highway Bypass, Chester, NY 10918
    /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
  • 26 W Meadow Way, Chester, NY 10918

    $869,000

    Sold Jul 24, 2025

    26 W Meadow Way, Chester, NY 10918

    • 4 Beds
    • 3 Baths
    • 3,100 Sq Ft
    • Built 2024

    Last Sold Summary

    • 3% Below List Price
    • $280/SF
    • 85 Days On Market

    Current Estimated Value $119,000

    Last Listing Agent Nancy Sardo BHG Real Estate Green Team

    26 W Meadow Way, Chester, NY 10918

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