6,841

Chester, NY Homes

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  • L12 Adirondack Heights Rd Unit Lot 6, Chester, NY 12817
    L12 Adirondack Heights Rd Unit Lot 6, Chester, NY 12817
    L12 Adirondack Heights Rd Unit Lot 6, Chester, NY 12817
    /13

    $79,500

    Sold Dec 09, 2025

    L12 Adirondack Heights Rd Unit Lot 6, Chester, NY 12817

    • Land
    • 14.7 Acres
    • $5,408 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 110 Days On Market

    Last Listing Agent Julia Pucciarelli Gallo Realty ADK Inc

    L12 Adirondack Heights Rd Unit Lot 6, Chester, NY 12817
  • 2 Heidi Ln, Chester, NY 10918
    2 Heidi Ln, Chester, NY 10918
    2 Heidi Ln, Chester, NY 10918
    /44

    $869,000

    $31K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 3,846 Sq Ft

    2 Heidi Ln, Chester, NY 10918

    Set at the end of a quiet executive cul-de-sac, this refined modern colonial offers a rare blend of quality, scale, and effortless livability on over two acres of level, park-like grounds framed by mature trees. Designed for both everyday comfort and elevated entertaining, the home unfolds with a sense of openness and intention, where natural light and thoughtful craftsmanship define every

    Frank Muccari Cronin & Company Real Estate

    2 Heidi Ln, Chester, NY 10918
  • 12 Juniper Ln, Monroe, NY 10950

    $550,000

    Sold Mar 09, 2026

    12 Juniper Ln, Monroe, NY 10950

    • 4 Beds
    • 3 Baths
    • 2,288 Sq Ft
    • Built 1972

    Last Sold Summary

    • 4% Below List Price
    • $240/SF
    • 120 Days On Market

    Current Estimated Value $548,321

    Last Listing Agent Shaylene Neumann Houlihan Lawrence Inc.

    12 Juniper Ln, Monroe, NY 10950
  • 19 Greentree Ln, Chester, NY 10918
    19 Greentree Ln, Chester, NY 10918
    19 Greentree Ln, Chester, NY 10918
    /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
  • 31 Leone Ln, Chester, NY 10918

    $75,000

    Sold Jul 09, 2025

    31 Leone Ln, Chester, NY 10918

    • Land
    • 7.5 Acres
    • $10,000 per Acre

    Last Sold Summary

    • 50% Below List Price
    • 73 Days On Market

    Last Listing Agent Carole McCann Hudson Heritage Realty

    31 Leone Ln, Chester, NY 10918
  • 24 Walnut St, Chester, NY 10918
    24 Walnut St, Chester, NY 10918
    24 Walnut St, Chester, NY 10918
    /28

    $579,999

    • 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
  • 174 Creamery Pond Rd, Chester, NY 10918

    $665,000

    Sold Jul 15, 2025

    174 Creamery Pond Rd, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,608 Sq Ft
    • Built 2004

    Last Sold Summary

    • 1% Below List Price
    • $255/SF
    • 27 Days On Market

    Current Estimated Value $700,768

    Last Listing Agent Michele Tobin Keller Williams Realty

    174 Creamery Pond Rd, Chester, NY 10918
    • 14 Jeffrey Dr, Chester, NY 10918

      Est $606,633

      Not Listed For Sale

      14 Jeffrey Dr, Chester, NY 10918

      • 3 Beds
      • 2.5 Baths
      • 2,117 Sq Ft
      • Built 1987
      14 Jeffrey Dr, Chester, NY 10918

      Last Sold Summary

      • 37 Days On Market

  • 4 Greycourt Rd, Chester, NY 10918
    4 Greycourt Rd, Chester, NY 10918
    4 Greycourt Rd, Chester, NY 10918
    /12

    $640,000

    • 3 Beds
    • 1.5 Baths
    • 2,136 Sq Ft

    4 Greycourt Rd, Chester, NY 10918

    Welcome to 4 Greycourt Road, your dream home awaits! This delightful residence boasts a spacious 6-room layout, featuring 3 generous bedrooms and 1.5 baths, all nestled on over 2.5 acres of stunning greenery. Imagine whipping up culinary masterpieces in the well-appointed kitchen, complete with ample cabinetry and modern appliances—perfect for any cooking enthusiast! Each bedroom is a serene

    Nathen Singer MK Realty Inc

    4 Greycourt Rd, Chester, NY 10918
  • 559 Laroe Rd, Chester, NY 10918

    $465,000

    Sold Aug 04, 2025

    559 Laroe Rd, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 1970

    Last Sold Summary

    • 11% Below List Price
    • $245/SF
    • 239 Days On Market

    Current Estimated Value $481,280

    Last Listing Agent Eliezer Safdie Sage Realty Center LLC

    559 Laroe Rd, Chester, NY 10918
  • 58 Oxford Springs Rd, Chester, NY 10918
    58 Oxford Springs Rd, Chester, NY 10918
    58 Oxford Springs Rd, Chester, NY 10918
    /38

    $349,900

    Pending
    • 1 Bed
    • 1 Bath
    • 783 Sq Ft

    58 Oxford Springs Rd, Chester, NY 10918

    Highest and Best Due 4/17 by 2pm. Tucked away in a serene, wooded setting, this extraordinary private retreat offers a rare blend of craftsmanship and natural beauty. Surrounded by mature trees and complete privacy, this meticulously curated home is a true sanctuary—where every detail has been thoughtfully designed to elevate everyday living. From the moment you arrive, the property makes a

    Christine Koenig Keller Williams Realty

    58 Oxford Springs Rd, Chester, NY 10918
  • 16 Mari Rd, Chester, NY 10918

    $501,500

    Sold Mar 03, 2026

    16 Mari Rd, Chester, NY 10918

    • 4 Beds
    • 3 Baths
    • 2,098 Sq Ft
    • Built 1970

    Last Sold Summary

    • $239/SF
    • 75 Days On Market

    Current Estimated Value $510,137

    Last Listing Agent Kimberly Corkum Keller Williams Realty

    16 Mari Rd, Chester, NY 10918
  • 30 Harding Way, Chester, NY 10950
    30 Harding Way, Chester, NY 10950
    30 Harding Way, Chester, NY 10950
    /7

    $500,000

    • Land
    • 9.78 Acres
    • $51,125 per Acre

    30 Harding Way, Chester, NY 10950

    An exceptional opportunity for builders and investors in the highly desirable Town of Chester and Town of Monroe, within the Monroe–Woodbury School District. This offering includes four contiguous lots for the price of one, providing significant development potential. The assemblage consists of 30 Harding Way (0.18 acres; Section 27, Block 3, Lot 11), sold together with the adjoining parcels: Lot

    Ida Payne Keller Williams Realty

    30 Harding Way, Chester, NY 10950
  • 12 Mari Rd, Chester, NY 10918

    $457,500

    Sold Jul 25, 2025

    12 Mari Rd, Chester, NY 10918

    • 4 Beds
    • 1.5 Baths
    • 1,842 Sq Ft
    • Built 1970

    Last Sold Summary

    • 4% Below List Price
    • $248/SF
    • 32 Days On Market

    Current Estimated Value $475,587

    Last Listing Agent Ryan Degnan Howard Hanna Rand Realty

    12 Mari Rd, Chester, NY 10918
  • L46 Pinewood Rd N, Chester, NY 12817
    L46 Pinewood Rd N, Chester, NY 12817
    L46 Pinewood Rd N, Chester, NY 12817
    /4

    $19,000

    Pending
    • Land
    • 1.38 Acres
    • $13,768 per Acre

    L46 Pinewood Rd N, Chester, NY 12817

    Prime 1.38-acre building lot located in the heart of Chestertown! This level parcel offers an excellent opportunity to build your Adirondack dream home or vacation getaway. Conveniently situated just minutes from shopping, restaurants, local lakes/hiking trails, Gore Mountain & the Northway!

    Julia Pucciarelli Gallo Realty ADK Inc

    L46 Pinewood Rd N, Chester, NY 12817
  • 2915 Whispering Hills Unit 596, Chester, NY 10918

    $382,000

    Sold Mar 25, 2026

    2915 Whispering Hills Unit 596, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft
    • Built 1987

    Last Sold Summary

    • 4% Above List Price
    • $287/SF
    • 43 Days On Market

    Current Estimated Value $376,041

    Last Listing Agent Johanna Monzon Ruballos Century 21 Full Service Realty

    2915 Whispering Hills Unit 596, Chester, NY 10918
  • 2703 Whispering Hills, Chester, NY 10918
    2703 Whispering Hills, Chester, NY 10918
    2703 Whispering Hills, Chester, NY 10918
    /39

    $365,000

    Open Sat 11AM - 1PM
    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft

    2703 Whispering Hills, Chester, NY 10918

    Welcome to 2703 Whispering Hills in Chester, NY — a beautifully updated home that stands out from the rest. This well-maintained unit features numerous recent improvements, including new windows, a new garage door, and a new hot water heater, providing peace of mind for years to come. The central air conditioning system is approximately five years old and keeps the home comfortable throughout the

    Rebecca Matta-Candela Keller Williams Realty

    2703 Whispering Hills, Chester, NY 10918
  • 3917 Whispering Hills, Chester, NY 10918

    $305,000

    Sold Jun 05, 2026

    3917 Whispering Hills, Chester, NY 10918

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

    Last Sold Summary

    • 4% Below List Price
    • $285/SF
    • 138 Days On Market

    Current Estimated Value $306,459

    Last Listing Agent Jie Liu KW Hudson Valley Untied

    3917 Whispering Hills, Chester, NY 10918
  • L62.2 Moffitt Rd, Chester, NY 12817
    L62.2 Moffitt Rd, Chester, NY 12817
    L62.2 Moffitt Rd, Chester, NY 12817
    /3

    $75,000

    Pending
    • Land
    • 12 Acres
    • $6,250 per Acre

    L62.2 Moffitt Rd, Chester, NY 12817

    12-acre parcel offering beautiful terrain and privacy, yet on a town-maintained road. Plenty of options for a home setting. A very desirable property for your future home construction. Only 15 minutes to Gore Mountain Ski Area, 3 miles to Loon Lake and within a mile of the Hudson River. A wonderful opportunity to enjoy the Adirondack experience. $75,000

    Carol Monroe Najer Realty

    L62.2 Moffitt Rd, Chester, NY 12817
  • 23 Pewter Cir, Chester, NY 10918

    $675,000

    Sold Feb 20, 2026

    23 Pewter Cir, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,318 Sq Ft
    • Built 1998

    Last Sold Summary

    • 4% Above List Price
    • $291/SF
    • 21 Days On Market

    Current Estimated Value $665,732

    Last Listing Agent Rosemary DelliCarpini eXp Realty

    23 Pewter Cir, Chester, NY 10918
  • 60 Whitetail Run, Chester, NY 10918
    60 Whitetail Run, Chester, NY 10918
    60 Whitetail Run, Chester, NY 10918
    /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
  • 326 Heritage Ln, Monroe, NY 10950

    $345,000

    Sold Aug 05, 2025

    326 Heritage Ln, Monroe, NY 10950

    • 3 Beds
    • 2.5 Baths
    • 1,698 Sq Ft
    • Built 1998

    Last Sold Summary

    • 4% Below List Price
    • $203/SF
    • 37 Days On Market

    Current Estimated Value $364,789

    Last Listing Agent Ernie Acampora River Realty Services, Inc.

    326 Heritage Ln, Monroe, NY 10950
  • 34 Carriage Knolls Rd, Chester, NY 12817
    34 Carriage Knolls Rd, Chester, NY 12817
    34 Carriage Knolls Rd, Chester, NY 12817
    /8

    $39,500

    • Land
    • 1.82 Acres
    • $21,703 per Acre

    34 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 a

    Walter Swartz Gallo Realty ADK Inc

    34 Carriage Knolls Rd, Chester, NY 12817
  • 114 Old Mansion Rd, Chester, NY 10918

    $555,000

    Sold Oct 21, 2025

    114 Old Mansion Rd, Chester, NY 10918

    • 4 Beds
    • 2 Baths
    • 3,330 Sq Ft
    • Built 1930

    Last Sold Summary

    • 21% Below List Price
    • $167/SF
    • 76 Days On Market

    Current Estimated Value $647,849

    Last Listing Agent Hershel Lowy Master Realty Group Inc.

    114 Old Mansion Rd, Chester, NY 10918
  • 2948 State Route 94, Chester, NY 10918
    2948 State Route 94, Chester, NY 10918
    2948 State Route 94, Chester, NY 10918
    /45

    $1,300,000

    $95K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,866 Sq Ft

    2948 State Route 94, Chester, NY 10918

    Set atop a gentle hill with sweeping eastern views of Round Hill and Schunnemunk Ridge, this pristine 1860 farmhouse blends preserved historic character with thoughtful modern updates. Originally part of the Sears family dairy pasture, the 3,866 sq ft home has been meticulously maintained and features original wide-plank hardwood floors, a striking hand-carved banister, five fireplaces with

    Elizabeth Broderick Tuxedo Hudson Realty Corp

    2948 State Route 94, Chester, NY 10918
  • 56 Sunset Ridge Rd, Monroe, NY 10950

    $725,000

    Sold Jun 30, 2025

    56 Sunset Ridge Rd, Monroe, NY 10950

    • 4 Beds
    • 4 Baths
    • 3,626 Sq Ft
    • Built 1993

    Last Sold Summary

    • 1% Above List Price
    • $200/SF
    • 34 Days On Market

    Current Estimated Value $764,849

    Last Listing Agent Moses Schreiber MS Realty Group USA, Inc

    56 Sunset Ridge Rd, Monroe, NY 10950
  • 1401 Whispering Hills, Chester, NY 10918
    1401 Whispering Hills, Chester, NY 10918
    1401 Whispering Hills, Chester, NY 10918
    /33

    $260,000

    $35K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft

    1401 Whispering Hills, Chester, NY 10918

    Discover the perfect blend of comfort, convenience, and community in this 2-bedroom, 1-bath end-unit townhouse. Situated in a quiet corner of the neighborhood, this home offers extra privacy and natural light, along with the added benefit of an attached 1-car garage for secure parking and storage. Inside, you'll find a thoughtfully designed layout that maximizes space and livability - ideal for

    Debbie Goldstein Howard Hanna Rand Realty

    1401 Whispering Hills, Chester, NY 10918
  • 2 Dawn Ct, Chester, NY 10918

    $669,000

    Sold Jan 12, 2026

    2 Dawn Ct, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 3,092 Sq Ft
    • Built 1986

    Last Sold Summary

    • 6% Below List Price
    • $216/SF
    • 76 Days On Market

    Current Estimated Value $663,387

    Last Listing Agent Dulce M Ferrera KW Hudson Valley Untied

    2 Dawn Ct, Chester, NY 10918

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