6,751

Chester, NY Homes

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  • 2604 Whispering Hills, Chester, NY 10918
    2604 Whispering Hills, Chester, NY 10918
    2604 Whispering Hills, Chester, NY 10918
    /35

    $350,000

    • 3 Beds
    • 2.5 Baths
    • 1,086 Sq Ft

    2604 Whispering Hills, Chester, NY 10918

    Welcome to 2604 Whispering Hills! This beautifully maintained, move-in-ready 3-bedroom, 2.5-bath townhome offers comfort, style, and numerous recent updates. Major improvements completed within the last five years include new windows, furnace, water heater, washer, and dryer, providing peace of mind for the new owner. The bright, spacious floor plan is perfect for everyday living and

    Sonia Gonzalez HomeSmart Homes & Estates

    2604 Whispering Hills, Chester, NY 10918
    • 6 Silvertail Rd, Chester, NY 10918

      Est $1,203,750

      Not Listed For Sale

      6 Silvertail Rd, Chester, NY 10918

      • 6 Beds
      • 4.5 Baths
      • 5,127 Sq Ft
      • Built 1794
      6 Silvertail Rd, Chester, NY 10918

      Last Sold Summary

      • 304 Days On Market

      Last Listing Agent MaryBeth O'Hara Ellis Sotheby's Intl Realty

  • 60 Carriage Knolls Rd, Chester, NY 12817
    60 Carriage Knolls Rd, Chester, NY 12817
    60 Carriage Knolls Rd, Chester, NY 12817
    /10

    $37,500

    • Land
    • 1.62 Acres
    • $23,148 per Acre

    60 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

    Walter Swartz Gallo Realty ADK Inc

    60 Carriage Knolls Rd, Chester, NY 12817
    • 10 Silvertail Rd, Chester, NY 10918

      Est $1,366,408

      Not Listed For Sale

      10 Silvertail Rd, Chester, NY 10918

      • 4 Beds
      • 4.5 Baths
      • 5,007 Sq Ft
      • Built 2006
      10 Silvertail Rd, Chester, NY 10918

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Ammar Iqbal eXp Realty

  • 2 Pine Hill Rd, Chester, NY 10918
    2 Pine Hill Rd, Chester, NY 10918
    2 Pine Hill Rd, Chester, NY 10918
    /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
    • 40 Deer Trail Rd, Chester, NY 10918

      Est $1,074,771

      Not Listed For Sale

      40 Deer Trail Rd, Chester, NY 10918

      • 4 Beds
      • 4.5 Baths
      • 3,114 Sq Ft
      • Built 1991
      40 Deer Trail Rd, Chester, NY 10918

      Last Sold Summary

      • 387 Days On Market

      Last Listing Agent Theresa Negast Christie's Int. Real Estate

  • 4 Debbie Ct, Chester, NY 10918
    4 Debbie Ct, Chester, NY 10918
    4 Debbie Ct, Chester, NY 10918
    /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
    • 208 Glenmere Rd, Chester, NY 10918

      Est $525,253

      Not Listed For Sale

      208 Glenmere Rd, Chester, NY 10918

      • 5 Beds
      • 2.5 Baths
      • 1,815 Sq Ft
      • Built 1900
      208 Glenmere Rd, Chester, NY 10918

      Last Sold Summary

      • 43 Days On Market

      Last Listing Agent Chris Scibelli Keller Williams Realty

  • 18 Southside Dr, Monroe, NY 10950
    18 Southside Dr, Monroe, NY 10950
    18 Southside Dr, Monroe, NY 10950
    /36

    $495,000

    Pending
    • 4 Beds
    • 3 Baths
    • 1,792 Sq Ft

    18 Southside Dr, Monroe, NY 10950

    Welcome to 18 Southside Drive, this charming ranch-style home nestled in the highly sought-after Walton Park neighborhood of Monroe. Offering the ultimate ease of effortless one level living, this spacious residence boasts 4 bedrooms, 3 full bathrooms, and a versatile layout situated within the premier Monroe-Woodbury School District. The expansive property features an attached garage, and a

    Nikki Grzegorzewski Keller Williams Realty

    18 Southside Dr, Monroe, NY 10950
    • 220 Glenmere Rd, Chester, NY 10918

      Est $496,948

      Not Listed For Sale

      220 Glenmere Rd, Chester, NY 10918

      • 3 Beds
      • 1.5 Baths
      • 1,268 Sq Ft
      • Built 1972
      220 Glenmere Rd, Chester, NY 10918

      Last Sold Summary

      • 159 Days On Market

      Last Listing Agent Kathy Dawson Howard Hanna Rand Realty

  • L9 Byrd Pond, Chester, NY 12853
    L9 Byrd Pond, Chester, NY 12853
    L9 Byrd Pond, Chester, NY 12853
    /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
    • 226 Glenmere Rd, Chester, NY 10918

      Est $522,598

      Not Listed For Sale

      226 Glenmere Rd, Chester, NY 10918

      • 4 Beds
      • 1.5 Baths
      • 1,530 Sq Ft
      • Built 1976
      226 Glenmere Rd, Chester, NY 10918

      Last Sold Summary

      • 203 Days On Market

      Last Listing Agent Kathy Dawson Howard Hanna Rand Realty

  • 106 Carriage Knoll Rd, Chester, NY 12817
    106 Carriage Knoll Rd, Chester, NY 12817
    106 Carriage Knoll Rd, Chester, NY 12817
    /25

    $78,900

    $14K PRICE INCREASE
    • Land
    • 5.76 Acres
    • $13,698 per Acre

    106 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

    106 Carriage Knoll Rd, Chester, NY 12817
    • 464 Pine Hill Rd, Chester, NY 10918

      Est $357,996

      Not Listed For Sale

      464 Pine Hill Rd, Chester, NY 10918

      • 3 Beds
      • 1 Bath
      • 920 Sq Ft
      • Built 1930
      464 Pine Hill Rd, Chester, NY 10918

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Ralph Harvey ListWithFreedom.Com

  • 102 Hillcrest Ave, Monroe, NY 10950
    102 Hillcrest Ave, Monroe, NY 10950
    102 Hillcrest Ave, Monroe, NY 10950
    /4

    $300,000

    • 2 Beds
    • 1 Bath
    • 1,396 Sq Ft

    102 Hillcrest Ave, Monroe, NY 10950

    Situated in a quiet neighborhood on level corner property. House is in need of complete renovation. A suitable project for experienced contractor/builder.

    Rosy Wansor Wansor Realty

    102 Hillcrest Ave, Monroe, NY 10950
    • 152 Gibson Hill Rd, Chester, NY 10918

      Est $803,711

      Not Listed For Sale

      152 Gibson Hill Rd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 3,176 Sq Ft
      • Built 1997
      152 Gibson Hill Rd, Chester, NY 10918

      Last Sold Summary

      • 230 Days On Market

      Last Listing Agent Kimberly Corkum Keller Williams Realty

  • 197 Oxford Rd, Chester, NY 10918
    197 Oxford Rd, Chester, NY 10918
    197 Oxford Rd, Chester, NY 10918
    /36

    $799,000

    • 4 Beds
    • 2.5 Baths
    • 3,070 Sq Ft

    197 Oxford Rd, Chester, NY 10918

    Welcome to this beautifully charming Center Hall Colonial, privately set back from the road on a picturesque property with a tranquil man-made pond, fountain, and inviting wrap-around front porch. This spacious home offers the perfect balance of classic elegance and comfortable everyday living. The thoughtfully designed floor plan features a formal living room that flows seamlessly into the warm

    Regina Carmel Howard Hanna Rand Realty

    197 Oxford Rd, Chester, NY 10918
    • 27 Beverly Rd, Chester, NY 10918

      Est $693,720

      Not Listed For Sale

      27 Beverly Rd, Chester, NY 10918

      • 3 Beds
      • 2.5 Baths
      • 2,511 Sq Ft
      • Built 1995
      27 Beverly Rd, Chester, NY 10918

      Last Sold Summary

      • 57 Days On Market

      Last Listing Agent Alison Orlando KW Hudson Valley United

  • 68 Conklingtown Rd Unit 1&2, Chester, NY 10918
    68 Conklingtown Rd Unit 1&2, Chester, NY 10918
    68 Conklingtown Rd Unit 1&2, Chester, NY 10918
    /38

    $575,000

    • 6 Beds
    • 2 Baths

    68 Conklingtown Rd Unit 1&2, Chester, NY 10918

    Rare opportunity. Come in and see this multi-family property in Chester, NY, and very close to main highways. This features 2 separate structures with their own utilities and natural gas. The main house presents 4 bedrooms, a kitchen, a dining room, and a living room with 1 full bath. main house is fully professional painted recently and now floors and roof on this house is 2 years old. The

    Moses Schreiber MS Realty Group USA, Inc

    68 Conklingtown Rd Unit 1&2, Chester, NY 10918
    • 3 Sunset Ridge Rd, Monroe, NY 10950

      Est $816,646

      Not Listed For Sale

      3 Sunset Ridge Rd, Monroe, NY 10950

      • 4 Beds
      • 3.5 Baths
      • 3,524 Sq Ft
      • Built 1996
      3 Sunset Ridge Rd, Monroe, NY 10950

      Last Sold Summary

      • 94 Days On Market

      Last Listing Agent Nicholas Cuomo Keller Williams Realty

  • 70 Main St, Chester, NY 10918
    70 Main St, Chester, NY 10918
    70 Main St, Chester, NY 10918
    /27

    $469,000

    • 3 Beds
    • 3 Baths
    • 1,357 Sq Ft

    70 Main St, Chester, NY 10918

    Welcome to 70 Main Street, a village gem situated right in the heart of historic Chester! This versatile 4-bedroom, 2.5-bathroom home combines classic architectural character with generous living spaces and modern convenience. The main residence features an inviting floor plan with bright, sunlit rooms and comfortable living areas throughout. A standout highlight of this property is the separate

    Pedro Garcia Curasi Realty, Inc.

    70 Main St, Chester, NY 10918
    • 55 Brookview Dr, Monroe, NY 10950

      Est $866,460

      Not Listed For Sale

      55 Brookview Dr, Monroe, NY 10950

      • 3 Beds
      • 4 Baths
      • 2,907 Sq Ft
      • Built 1993
      55 Brookview Dr, Monroe, NY 10950

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Laurel Lustgarten Howard Hanna Rand Realty

  • 335 Laroe Rd, Chester, NY 10918
    335 Laroe Rd, Chester, NY 10918
    335 Laroe Rd, Chester, NY 10918
    /35

    $675,000

    Open Sun 2PM - 4PM $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'Altilio Coldwell Banker Choice Prop.

    335 Laroe Rd, Chester, NY 10918
    • 46 Brookview Dr, Monroe, NY 10950

      Est $985,828

      Not Listed For Sale

      46 Brookview Dr, Monroe, NY 10950

      • 5 Beds
      • 5 Baths
      • 4,200 Sq Ft
      • Built 1993
      46 Brookview Dr, Monroe, NY 10950

      Last Sold Summary

      • 146 Days On Market

      Last Listing Agent David White Owner Entry.com

  • 6 Adams Ct, Monroe, NY 10950
    6 Adams Ct, Monroe, NY 10950
    6 Adams Ct, Monroe, NY 10950
    /44

    $585,000

    $14K PRICE DROP Pending
    • 4 Beds
    • 2 Baths
    • 2,056 Sq Ft

    6 Adams Ct, Monroe, NY 10950

    Stunning Split Ranch with Pool and Gorgeous Curb Appeal, Located in the Town of Chester within the Monroe-Woodbury School District Welcome to this beautifully maintained 4-bedroom, 2 full bath split ranch offering the perfect blend of comfort, style, and functionality. The upper level features a spacious and sun-filled eat-in kitchen, ideal for everyday living, with direct access to a big Trex

    Ida Payne Keller Williams Realty

    6 Adams Ct, Monroe, NY 10950
    • 56 Sunset Ridge Rd, Monroe, NY 10950

      Est $842,228

      Not Listed For Sale

      56 Sunset Ridge Rd, Monroe, NY 10950

      • 4 Beds
      • 4 Baths
      • 3,626 Sq Ft
      • Built 1993
      56 Sunset Ridge Rd, Monroe, NY 10950

      Last Sold Summary

      • 34 Days On Market

      Last Listing Agent Moses Schreiber MS Realty Group USA, Inc

  • 56 Poplar Dr, Monroe, NY 10950
    56 Poplar Dr, Monroe, NY 10950
    56 Poplar Dr, Monroe, NY 10950
    /29

    $550,000

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

    56 Poplar Dr, Monroe, NY 10950

    BiLevel/Raised Ranch on Quiet Street with Room to Grow! Come home and relax on the upper level deck overlooking state land that offers additional privacy. This well-maintained home clearly shows the pride of ownership. Open concept living room and dining room features many windows that fill the home with natural sunlight. Enjoy the convenience of the updated full bathroom and three comfortable

    Jeffrey Jacobsen Terrie OConnor

    56 Poplar Dr, Monroe, NY 10950
    • 11 Sunfish Ln, Monroe, NY 10950

      Est $1,190,145

      Not Listed For Sale

      11 Sunfish Ln, Monroe, NY 10950

      • 5 Beds
      • 3 Baths
      • 4,198 Sq Ft
      • Built 1996
      11 Sunfish Ln, Monroe, NY 10950

      Last Sold Summary

      • 64 Days On Market

      Last Listing Agent Layla Rose Boyles Century 21 Realty Center

  • 552 Pine Hill Rd, Chester, NY 10918
    552 Pine Hill Rd, Chester, NY 10918
    /2

    $299,000

    $51K PRICE DROP
    • Land
    • 5.7 Acres
    • $52,456 per Acre

    552 Pine Hill Rd, Chester, NY 10918

    Beautiful 5.7-acre residential parcel located in the Town of chester, offering an exceptional opportunity to build your custom dream home in a peaceful, private setting. With ample space for a spacious residence and outdoor living areas (subject to town approvals), this property combines natural surroundings with convenient access to nearby amenities, schools, and major roadways. Adjacent to 558

    Charnie Guttmann eRealty Advisors, Inc

    552 Pine Hill Rd, Chester, NY 10918
    • 104 Trout Brook Rd, Monroe, NY 10950

      Est $625,239

      Not Listed For Sale

      104 Trout Brook Rd, Monroe, NY 10950

      • 3 Beds
      • 2 Baths
      • 2,232 Sq Ft
      • Built 1999
      104 Trout Brook Rd, Monroe, NY 10950

      Last Sold Summary

      • 82 Days On Market

      Last Listing Agent Sandra Arnez KW Hudson Valley United

  • 82 Carriage Knoll Rd, Chester, NY 12817
    82 Carriage Knoll Rd, Chester, NY 12817
    82 Carriage Knoll Rd, Chester, NY 12817
    /23

    $68,900

    $19K PRICE INCREASE
    • Land
    • 3.05 Acres
    • $22,590 per Acre

    82 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

    82 Carriage Knoll Rd, Chester, NY 12817
    • 46 Creamery Pond Rd, Chester, NY 10918

      Est $715,128

      Not Listed For Sale

      46 Creamery Pond Rd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,792 Sq Ft
      • Built 1999
      46 Creamery Pond Rd, Chester, NY 10918

      Last Sold Summary

      • 48 Days On Market

      Last Listing Agent Sandra Arnez KW Hudson Valley United

  • L10 Stone Bridge Rd, Chester, NY 12860
    L10 Stone Bridge Rd, Chester, NY 12860
    L10 Stone Bridge Rd, Chester, NY 12860
    /38

    $145,000

    Pending
    • Land
    • 9.38 Acres
    • $15,458 per Acre

    L10 Stone Bridge Rd, Chester, NY 12860

    Schroon Lake Area ~ Super opportunity to enjoy almost 10 acres of wooded land with over 1100' on beautiful Trout Brook, located just 1 mile from the Schroon Lake Boat Launch. Make use of a 24' x 20' 2-story barn. It's been partially finished with a concrete floor and woodstove, with the second floor used for sleeping and play space for the kids. Use it for your camping getaway, as the current

    Linda Marcella Adirondack Real Estate LLC

    L10 Stone Bridge Rd, Chester, NY 12860
    • 125 Creamery Pond Rd, Chester, NY 10918

      Est $732,020

      Not Listed For Sale

      125 Creamery Pond Rd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,658 Sq Ft
      • Built 1997
      125 Creamery Pond Rd, Chester, NY 10918

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Jennifer DiCostanzo RE/MAX Town & Country

  • 26 Bridle Ln, Chester, NY 10918
    26 Bridle Ln, Chester, NY 10918
    26 Bridle Ln, Chester, NY 10918
    /29

    $685,000

    $35K PRICE DROP Pending
    • 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
    • 146 Pine Hill Rd, Chester, NY 10918

      Est $670,155

      Not Listed For Sale

      146 Pine Hill Rd, Chester, NY 10918

      • 3 Beds
      • 2.5 Baths
      • 2,414 Sq Ft
      • Built 1987
      146 Pine Hill Rd, Chester, NY 10918

      Last Sold Summary

      • 82 Days On Market

      Last Listing Agent Frank Golio Howard Hanna Rand Realty

  • 17 Woodridge Dr, Chester, NY 10918
    17 Woodridge Dr, Chester, NY 10918
    17 Woodridge Dr, Chester, NY 10918
    /50

    $623,900

    $125K PRICE DROP Pending
    • 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
    • 168 Pine Hill Rd, Chester, NY 10918

      Est $665,915

      Not Listed For Sale

      168 Pine Hill Rd, Chester, NY 10918

      • 5 Beds
      • 3.5 Baths
      • 2,952 Sq Ft
      • Built 1930
      168 Pine Hill Rd, Chester, NY 10918

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Dean Diltz Keller Williams Realty

  • 38 Granite Ridge Rd, Chester, NY 12817
    38 Granite Ridge Rd, Chester, NY 12817
    38 Granite Ridge Rd, Chester, NY 12817
    /24

    $74,000

    $10K PRICE DROP
    • Land
    • 2.84 Acres
    • $26,056 per Acre

    38 Granite Ridge Rd, Chester, NY 12817

    Private 2.84-acre partially cleared, buildable lot in a peaceful setting with proposed home and septic locations. Property features a gravel driveway with camper pad, Amish-built shed on gravel base, fire pit, and walking trail. Infrastructure in place includes 200-amp underground electric service plus 30-amp and 50-amp RV hookups. Conveniently located minutes from Cronin's Golf Resort, Friends

    Nicholas Khachadourian KW Platform

    38 Granite Ridge Rd, Chester, NY 12817
    • 49 Hambletonian Rd, Chester, NY 10918

      Est $650,175

      Not Listed For Sale

      49 Hambletonian Rd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,600 Sq Ft
      • Built 1992
      49 Hambletonian Rd, Chester, NY 10918

      Last Sold Summary

      • 45 Days On Market

      Last Listing Agent Dean Nugent Mary Jane Pastor Realty

Showing Results 401 - 440, Page 11 of 18

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