6,807

Chester, NY Homes

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  • 52 Surrey Rd, Chester, NY 10918

    $360,000 Sold Oct 09, 2024

    • 1,780 Sq Ft
    • $202/SF
    • 104 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1969

    52 Surrey Rd, Chester, NY 10918

    Dreaming of a project that lets your creativity soar? Envision the endless possibilities with our exclusive raised ranch, nestled in peaceful neighborhood. It may require a loving touch to see past the wear, but imagine transforming this space into a home that’s uniquely yours! This delightful property features a versatile layout, stainless steel appliances, fireplace and a unique 3-car detached

    Brian Caplicki Keller Williams Hudson Valley

    52 Surrey Rd, Chester, NY 10918
  • 104 Trout Brook Rd, Monroe, NY 10950

    $547,500 Sold Oct 08, 2024

    • 2,232 Sq Ft
    • $245/SF
    • 82 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1999

    104 Trout Brook Rd, Monroe, NY 10950

    This GORGEOUS home with Monroe Woodbury Schools sits in a quiet neighborhood of Chester & is now available for you to call Home! Enter into a spacious Living room with cathedral, vaulted ceilings with plenty of natural window light and a wood burning fireplace. Open floor layout to a formal dining room with modern light fixtures & hardwood floors throughout. Updated eat-in kitchen with tiled

    Sandra Arnez Keller Williams Hudson Valley

    104 Trout Brook Rd, Monroe, NY 10950
  • 4 Hickory Ln, Monroe, NY 10950

    $370,000 Sold Oct 08, 2024

    • 1,008 Sq Ft
    • $367/SF
    • 54 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1971

    4 Hickory Ln, Monroe, NY 10950

    Wonderful home loved and cared for by the same family for almost 50 years. Solid ranch living with an open, bright and spacious feel. Enjoy a serene setting in a friendly and quiet neighborhood. Recently updated kitchen and bathrooms. Central Air Conditioning and a new front porch and ramp, wheelchair accessible. Close to major shopping and restaurants, Woodbury Commons Shopping Outlets a

    Layla Rose Boyles Century 21 Realty Center

    4 Hickory Ln, Monroe, NY 10950
  • 1169 Craigville Rd, Chester, NY 10918

    $550,000 Sold Oct 07, 2024

    • 1,699 Sq Ft
    • $324/SF
    • 47 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1900

    1169 Craigville Rd, Chester, NY 10918

    Beautiful, bright and spacious home, lovingly maintained by the same owners for almost 20 years. Enjoy sunny and open living areas, architectural details and hardwood floors throughout the main living areas. Appliances recently updated and the electric updated in 2023. Bathrooms are modern and kitchen cabinets and backsplash were recently freshened-up as well. Roof approximately 15 years new.

    Layla Rose Boyles Century 21 Realty Center

    1169 Craigville Rd, Chester, NY 10918
  • 16 Bianca Blvd, Chester, NY 10918

    $600,000 Sold Oct 04, 2024

    • 3,192 Sq Ft
    • $188/SF
    • 21 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1987

    16 Bianca Blvd, Chester, NY 10918

    Welcome to your ideal sanctuary! This stunning four-bedroom center hall colonial showcases a beautiful Tudor-style exterior, thoughtfully crafted by its original owners. Situated in a tranquil cul-de-sac, this home blends elegance with peaceful living. As you enter, you'll be greeted by a spacious two-story foyer that sets a welcoming atmosphere for the entire residence. The main level features

    Patricia Sassi RE/MAX Benchmark Realty Group

    16 Bianca Blvd, Chester, NY 10918
  • 18 Oakland Ave, Chester, NY 10918

    $370,000 Sold Oct 03, 2024

    • 1,084 Sq Ft
    • $341/SF
    • 27 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1955

    18 Oakland Ave, Chester, NY 10918

    This is a "Neat as a pin" ranch in the Village of Chester. The kitchen has many updated appliances and a custom pantry with large pull-out drawers. The Living room wood floors were refinished and are immaculate. The bathroom has been updated and built to be ADA-compliant with a space-saving "pocket door." There is a large shed in the backyard, all near all the activities the Village has to

    Claude Brischoux Keller Williams Realty

    18 Oakland Ave, Chester, NY 10918
  • 2408 Whispering Hills Unit 639, Chester, NY 10918

    $315,000 Sold Oct 02, 2024

    • 1,072 Sq Ft
    • $294/SF
    • 8 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1987

    2408 Whispering Hills Unit 639, Chester, NY 10918

    WHISPERING HILLS TOWNHOME!!! Check out this 2 Bedrooms, 1.5 Bathroom Townhome nestled in the Whispering Hills Townhome community and in the Chester School District. This Townhome is located just outside of the Village of Chester, surrounded by a variety of community amenities including local shopping centers, restaurants, close to major attractions such as LEGOland, The Castle Fun Center, & a

    Richard Baxter Keller Williams Realty

    2408 Whispering Hills Unit 639, Chester, NY 10918
  • 37 Hubshop Rd, Chester, NY 10918

    $85,000 Sold Sep 27, 2024

    • 1,008 Sq Ft
    • $84/SF
    • 16 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1940

    37 Hubshop Rd, Chester, NY 10918

    Enormous potential! Ready for a makeover. If you find a better deal for under 85K, then you should buy it twice.

    John Olivero Keller Williams Realty

    37 Hubshop Rd, Chester, NY 10918
  • 46 Creamery Pond Rd, Chester, NY 10918

    $650,000 Sold Sep 25, 2024

    • 2,792 Sq Ft
    • $233/SF
    • 48 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1999

    46 Creamery Pond Rd, Chester, NY 10918

    Creamery Pond welcomes you to tour this spacious 4 bedroom, 2.5 bath Colonial located in the historic village of Sugar Loaf with Warwick Valley Schools. This beautiful colonial is nestled in a quiet neighborhood with manicured lawns and great curb appeal! A front deck welcomes you into a front entrance with ceramic floors that lead into a spacious open floor layout from formal living room with

    Sandra Arnez Keller Williams Hudson Valley

    46 Creamery Pond Rd, Chester, NY 10918
  • 19 Fawn Hill Rd, Chester, NY 10918

    $675,000 Sold Sep 20, 2024

    • 2,388 Sq Ft
    • $283/SF
    • 87 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2002

    19 Fawn Hill Rd, Chester, NY 10918

    Welcome to your private sanctuary, nestled on 1.9 park-like acres adorned with flowering trees and dramatic rock outcroppings. This stunning Colonial is perfectly sited on the hilltop, offering an unparalleled sense of seclusion and tranquility, while keeping you close to all of the local amenities for work, play and culture. As you approach, the rocking chair front porch invites you to unwind

    Jamie Corts Compass Greater NY, LLC

    19 Fawn Hill Rd, Chester, NY 10918
  • 26 Danielle Dr, Goshen, NY 10924

    $645,000 Sold Sep 19, 2024

    • 2,458 Sq Ft
    • $262/SF
    • 24 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2017

    26 Danielle Dr, Goshen, NY 10924

    Highest and best due Sunday at 6pm 6.30.24 Welcome to one of Goshen's most highly sought out neighborhoods "The Hills of Goshen". This Colonial offers 4-Bed, 2.5 Bed 2,400 Sqft, with hardwood floors, sitting pretty on 1.1 acres on a cul-da-sac! Once you enter your front door, you are welcomed by a sun drenched cathedral foyer, oversized dining room, perfect for hosting holidays, formal

    Erin Connolly Artisan Realty

    26 Danielle Dr, Goshen, NY 10924
  • 4205 Whispering Hills, Chester, NY 10918

    $295,000 Sold Sep 19, 2024

    • 1,072 Sq Ft
    • $275/SF
    • 85 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1987

    4205 Whispering Hills, Chester, NY 10918

    BACK ON THE MARKET!!! WHISPERING HILLS! LOW TAXES! Private Unit that Faces the Woods! 2 Bedrooms! 1 1/2 Bathrooms! 1 Car Garage! Two Level Living! New Carpet! New Flooring! Freshly Painted! Dining Room with Slider to Patio! Living Room! Perfect Commuter Location! Close to Major Highways & Shopping! Walk to NYC Bus! Country Club Living! Pools! Clubhouses! Tennis! Basket Ball! Tot Lot! Dog Walk!

    Amanda Dnistrian ARC Realty 1 in Sales

    4205 Whispering Hills, Chester, NY 10918
  • 51 Pewter Cir, Chester, NY 10918

    $505,000 Sold Sep 19, 2024

    • 2,623 Sq Ft
    • $193/SF
    • 67 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2007

    51 Pewter Cir, Chester, NY 10918

    Welcome to this stunning three bedroom 3.5 bathroom townhouse located in Sugar Loaf within Warwick Valley School District. This home spans three levels, offering spacious living areas and stylish finished throughout. The main level features an open-concept layout with gourmet kitchen, equipped with stainless steel appliances, granite countertops, and ample cabinet space. Adjacent to the

    Michele Tobin Keller Williams Realty

    51 Pewter Cir, Chester, NY 10918
  • 52 Farmingdale Rd, Chester, NY 10918

    $400,000 Sold Sep 18, 2024

    • 2,144 Sq Ft
    • $187/SF
    • 48 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1986

    52 Farmingdale Rd, Chester, NY 10918

    Opportunity knocks! A Colonial House Selling for Discount Price! Welcome to a Beautiful House structure which is a perfect combination of comfort and privacy, this bright four-bedroom Colonial House situated On a Lush green two acres flagged property. As you enter the Lot on Long driveway you'll be greeted by a quiet cozy Yard facing the House, entering the main Door to a little foyer than you'll

    David Katina ESTMAX REALTY

    52 Farmingdale Rd, Chester, NY 10918
  • 2009 Whispering Hills Unit 17, Chester, NY 10918

    $354,900 Sold Sep 17, 2024

    • 1,331 Sq Ft
    • $267/SF
    • 30 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1984

    2009 Whispering Hills Unit 17, Chester, NY 10918

    It's a WOW! This move in ready beautiful condo/Townhouse features 3 bedrooms, 2.5 baths, formal dining and 2 car attached garage. Live the fun life in this Whispering Hills community offering clubhouse, community pool, basketball and tennis. Only minutes to all stores and services as well. Master bedroom with private full bath, full hall bath for additional bedrooms. Main level has deck of

    Sandra Cotthaus 1st Independent Realty Grp

    2009 Whispering Hills Unit 17, Chester, NY 10918
  • 2008 Whispering Hills, Chester, NY 10918

    $295,000 Sold Sep 17, 2024

    • 1,053 Sq Ft
    • $280/SF
    • 29 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1984

    2008 Whispering Hills, Chester, NY 10918

    MOVE IN READY CONDO! Welcome to 2008 Whispering Hills, Chester, NY! This beautiful, updated townhome is ready for a new owner! Walk into this light, bright unit, and you are greeted by HW floors and a beautiful cultured stone fireplace, leading to your lovely eat in kitchen with french doors leading outside to your private patio area. Rounding out the main level is a half bath, and private

    Alissa Taylor-Vetell Keller Williams Realty

    2008 Whispering Hills, Chester, NY 10918
  • 47 Valley View Dr, Chester, NY 10918

    $699,000 Sold Sep 13, 2024

    • 3,812 Sq Ft
    • $183/SF
    • 72 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1998

    47 Valley View Dr, Chester, NY 10918

    Welcome to your dream home nestled in the serene beauty of the Hudson Valley! This custom built 5 bedroom, 3 1/2 -bathroom colonial offers a perfect blend of privacy & convenience. Situated on a private road, you'll enjoy peaceful surroundings just a short drive to shopping, schools & transportation. Step inside to discover spacious rooms adorned with hardwood floors and abundant natural light

    Claudia Lepore Keller Williams Realty

    47 Valley View Dr, Chester, NY 10918
  • 1404 N Gore Rd, Chester, NY 12817
    1404 N Gore Rd, Chester, NY 12817
    1404 N Gore Rd, Chester, NY 12817
    /3

    $45,000 Sold Sep 13, 2024

    • Land
    • 4 Acres
    • $11,250 per Acre

    1404 N Gore Rd, Chester, NY 12817

    North Gore Lot - Come build your dream on home this 4 acre 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. Adjoining 3.6 acre lot (1414 North Gore Rd) is also available.

    Amanda Gadway Gadway Realty

    1404 N Gore Rd, Chester, NY 12817
  • 40 Deer Trail Rd, Chester, NY 10918

    $1,100,000 Sold Sep 12, 2024

    • 3,114 Sq Ft
    • $353/SF
    • 387 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1991

    40 Deer Trail Rd, Chester, NY 10918

    Welcome to 40 Deer Trail Road, an exquisite and unique country retreat. This custom Colonial-style home is nestled on 9.9 acres of meticulously maintained and sub-dividable property. As you enter through the two-story entranceway, you'll immediately appreciate the attention to detail and tasteful design, including crown molding throughout the home. The main level of the house exudes elegance and

    Theresa Negast Christie's Int. Real Estate

    40 Deer Trail Rd, Chester, NY 10918
  • 0 Kings Highway Bypass Unit ONEH6331362, Chester, NY 10918

    $210,000 Sold Aug 13, 2025

    • Land
    • 3.8 Acres
    • $55,263 per Acre
    • 268 Days On Market

    0 Kings Highway Bypass Unit ONEH6331362, Chester, NY 10918

    Lot #2 in on the site plan in documents. Fully approved and building permit ready right in the Warwick school district! Minutes to Sugarloaf village and Warwick village. Very private! Can be sold as approved lot or a home built to suit as well.

    Ciro Gagliardi Keller Williams Realty

    0 Kings Highway Bypass Unit ONEH6331362, Chester, NY 10918

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