Homes in ZIP Code 10918

• 

  $505,000

  Sold Feb 26, 2026

  25 High St, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,898 Sq Ft
  • Built 1850

  Last Sold Summary

  • 4% Below List Price
  • $174/SF
  • 192 Days On Market

  Current Estimated Value $527,580

  Last Listing Agent Alicia Goldman Christie's Int. Real Estate

  25 High St, Chester, NY 10918
• 

  Est $503,294

  Not Listed For Sale

  21 Park Dr, Chester, NY 10918

  • 4 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1967

  21 Park Dr, Chester, NY 10918

  Last Sold Summary

  • 32 Days On Market
• 

  

  

  /15

  $999,000

  $251K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,148 Sq Ft

  168 Prospect Rd, Monroe, NY 10950

  Welcome to your dream home! Lovingly maintained and nestled in a peaceful community, this charming ranch sits on a picturesque one-acre lot. Step inside to a warm and inviting living space, highlighted by a cozy wood-burning stove—perfect for chilly evenings. The home features three comfortable bedrooms and a well-appointed bathroom, offering both comfort and functionality. Enjoy seamless

  Salvatore Girgenti Ben Bay Realty of Staten Isl.

  168 Prospect Rd, Monroe, NY 10950
• 

  $459,000

  Sold Aug 19, 2025

  15 Vivian Ln, Chester, NY 10918

  • 4 Beds
  • 2 Baths
  • 1,872 Sq Ft
  • Built 1968

  Last Sold Summary

  • 2% Above List Price
  • $245/SF
  • 25 Days On Market

  Current Estimated Value $475,173

  Last Listing Agent Joseph Giglio Keller Williams Realty

  15 Vivian Ln, Chester, NY 10918
• 

  Est $485,326

  Not Listed For Sale

  18 Park Dr, Chester, NY 10918

  • 4 Beds
  • 1.5 Baths
  • 1,800 Sq Ft
  • Built 1967

  18 Park Dr, Chester, NY 10918

  Last Sold Summary

  • 24 Days On Market
• 

  

  /35

  $675,000

  Open Sun 11AM - 1PM $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
• 

  $288,000

  Sold Apr 17, 2026

  2913 Whispering Hills Unit 595, Chester, NY 10918

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft
  • Built 1987

  Last Sold Summary

  • 3% Above List Price
  • $266/SF
  • 18 Days On Market

  Current Estimated Value $285,826

  Last Listing Agent Devon King HomeSmart Homes & Estates

  2913 Whispering Hills Unit 595, Chester, NY 10918
• 

  Est $616,276

  Not Listed For Sale

  27 Natures Trail, Chester, NY 10918

  • 4 Beds
  • 2 Baths
  • 2,420 Sq Ft
  • Built 1966

  27 Natures Trail, Chester, NY 10918

  Last Sold Summary

  • 78 Days On Market
• 

  /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
• 

  $348,000

  Sold Jun 11, 2026

  2203 Whispering Hills, Chester, NY 10918

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

  Last Sold Summary

  • 6% Below List Price
  • $261/SF
  • 47 Days On Market

  Current Estimated Value $361,547

  Last Listing Agent Marie Altieri Howard Hanna Rand Realty

  2203 Whispering Hills, Chester, NY 10918
• 

  Est $573,257

  Not Listed For Sale

  2 Fields Ln, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 2,604 Sq Ft
  • Built 1972

  2 Fields Ln, Chester, NY 10918

  Last Sold Summary

  • 24 Days On Market
• 

  

  /29

  $720,000

  • 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
• 

  $700,000

  Sold Oct 30, 2025

  19 Lake Station Rd, Warwick, NY 10990

  • 4 Beds
  • 1.5 Baths
  • 3,288 Sq Ft
  • Built 1865

  Last Sold Summary

  • $213/SF
  • 58 Days On Market

  Current Estimated Value $660,826

  Last Listing Agent Tammy Scotto Keller Williams Realty

  19 Lake Station Rd, Warwick, NY 10990
• 

  Est $812,687

  Not Listed For Sale

  50 Ruth Ln, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,612 Sq Ft
  • Built 1995

  50 Ruth Ln, Chester, NY 10918

  Last Sold Summary

  • 24 Days On Market
• 

  

  /50

  $623,900

  $125K PRICE DROP

  • 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. 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 years young. The pools heating system runs on propane tank. Entire home was freshly

  Sharon Kushner eXp Realty

  17 Woodridge Dr, Chester, NY 10918
• 

  $296,000

  Sold Jun 05, 2026

  3601 Whispering Hills, Chester, NY 10918

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft
  • Built 1990

  Last Sold Summary

  • 3% Below List Price
  • $273/SF
  • 23 Days On Market

  Current Estimated Value $303,971

  Last Listing Agent Janet Rendle Weichert Realtors

  3601 Whispering Hills, Chester, NY 10918
• 

  Est $564,230

  Not Listed For Sale

  351 Sugarloaf Mountain Rd, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,562 Sq Ft
  • Built 1993

  351 Sugarloaf Mountain Rd, Chester, NY 10918

  Last Sold Summary

  • 28 Days On Market
• 

  

  /45

  $499,000

  $30K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,060 Sq Ft

  63 Hubshop Rd, Chester, NY 10918

  Nestled on a quiet road off the beaten path, this serene 4-bedroom, 2.5-bathroom Colonial offers the perfect blend of secluded tranquility and commuter convenience. The main level features a traditional layout with a spacious living room, formal dining room, and a cozy recreation room perfect for relaxing. The functional eat-in kitchen serves as the heart of the home, while all four bedrooms are

  Charles Moore Keller Williams Realty

  63 Hubshop Rd, Chester, NY 10918
• 

  $340,000

  Sold Oct 15, 2025

  2503 Whispering Hills, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,316 Sq Ft
  • Built 1986

  Last Sold Summary

  • 8% Below List Price
  • $258/SF
  • 59 Days On Market

  Current Estimated Value $347,916

  Last Listing Agent Sonia Gonzalez HomeSmart Homes & Estates

  2503 Whispering Hills, Chester, NY 10918
• 

  Est $990,251

  Not Listed For Sale

  110 Ridge Rd, Chester, NY 10918

  • 4 Beds
  • 3.5 Baths
  • 4,190 Sq Ft
  • Built 1995

  110 Ridge Rd, Chester, NY 10918

  Last Sold Summary

  • 24 Days On Market
• 

  

  /32

  $329,900

  $25K PRICE DROP

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

  1311 Whispering Hills Unit 96, Chester, NY 10918

  Experience Elevated Living: Your Private Hudson Valley Retreat at 1311 Whispering Hills Welcome to a home that offers more than just square footage—it offers a lifestyle change. Nestled in the scenic rolling hills of Orange County, 1311 Whispering Hills is a masterclass in modern suburban living. This meticulously maintained residence captures the essence of "home" from the moment you step

  Michael Jenney Keller Williams Realty

  1311 Whispering Hills Unit 96, Chester, NY 10918
• 

  $725,000

  Sold May 27, 2026

  16 Oxford Springs Rd, Chester, NY 10918

  • 3 Beds
  • 3 Baths
  • 2,870 Sq Ft
  • Built 1988

  Last Sold Summary

  • 7% Below List Price
  • $253/SF
  • 117 Days On Market

  Current Estimated Value $740,162

  Last Listing Agent Jennifer Gold RE/MAX Benchmark Realty Group

  16 Oxford Springs Rd, Chester, NY 10918
• 

  Est $730,543

  Not Listed For Sale

  392 Bellvale Rd, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft
  • Built 1993

  392 Bellvale Rd, Chester, NY 10918

  Last Sold Summary

  • 68 Days On Market
• 

  

  /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
• 

  $415,000

  Sold Jul 03, 2025

  12 Oak St, Chester, NY 10918

  • 3 Beds
  • 1 Bath
  • 1,038 Sq Ft
  • Built 1959

  Last Sold Summary

  • 5% Above List Price
  • $400/SF
  • 24 Days On Market

  Current Estimated Value $410,239

  Last Listing Agent Jennifer Loprieno Howard Hanna Rand Realty

  12 Oak St, Chester, NY 10918
• 

  Est $661,690

  Not Listed For Sale

  63 Hambletonian Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,310 Sq Ft
  • Built 1997

  63 Hambletonian Rd, Chester, NY 10918

  Last Sold Summary

  • 25 Days On Market
• 

  

  /49

  $735,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 3,356 Sq Ft

  55 Beverly Rd, Chester, NY 10918

  Welcome to 55 Beverly Road, Chester—A Stunning, Move-In Ready Home This beautifully updated 3,156 square-foot home blends timeless charm with modern upgrades, offering space, comfort, and style throughout. The expansive floor plan features bright, inviting living areas with soaring vaulted ceilings, gleaming hardwood floors throughout, and a cozy masonry fireplace that serves as a perfect focal

  Jay Himelson Howard Hanna Rand Realty

  55 Beverly Rd, Chester, NY 10918
• 

  $365,000

  Sold Nov 14, 2025

  2409 Whispering Hills, Chester, NY 10918

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

  Last Sold Summary

  • 2% Above List Price
  • $274/SF
  • 26 Days On Market

  Current Estimated Value $367,309

  Last Listing Agent Linda Clark Hudson Valley Griffith

  2409 Whispering Hills, Chester, NY 10918
• 

  Est $595,501

  Not Listed For Sale

  73 Hambletonian Rd, Chester, NY 10918

  • 5 Beds
  • 2 Baths
  • 2,680 Sq Ft
  • Built 1948

  73 Hambletonian Rd, Chester, NY 10918

  Last Sold Summary

  • 17 Days On Market
• 

  

  /39

  $588,000

  $1K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 2,332 Sq Ft

  44 Sayer Rd, Blooming Grove, NY 10914

  WELCOME HOME! Beautifully updated and meticulously maintained tri-level home nestled in the desirable Tomahawk Lake community of Blooming Grove. This move-in-ready residence offers a bright and inviting layout with spacious living and dining areas, abundant natural light, and modern finishes throughout. Well-appointed kitchen equipped with s/s appliances, quartz counters, provides ample cabinetry

  Eliezer Safdie Sage Realty Center LLC

  44 Sayer Rd, Blooming Grove, NY 10914
• 

  $460,000

  Sold Aug 28, 2025

  22 Able Noble Dr, Chester, NY 10918

  • 4 Beds
  • 2 Baths
  • 1,770 Sq Ft
  • Built 1968

  Last Sold Summary

  • 8% Below List Price
  • $260/SF
  • 40 Days On Market

  Current Estimated Value $474,587

  Last Listing Agent Robin Kelly Picture It Sold, LLC

  22 Able Noble Dr, Chester, NY 10918
• 

  Est $783,897

  Not Listed For Sale

  15 Banker Dr, Chester, NY 10918

  • 4 Beds
  • 3.5 Baths
  • 2,396 Sq Ft
  • Built 2000

  15 Banker Dr, Chester, NY 10918

  Last Sold Summary

  • 32 Days On Market
• 

  

  /49

  $999,900

  $200K PRICE DROP

  • 4,032 Sq Ft

  206 Greycourt Rd, Chester, NY 10918

  INCREDIBLE PROPERTY!!! MUNICIPAL WATER!!! MONROE WOODBURY SCHOOL DISTRICT!!! Welcome to 206 Greycourt Road, Chester, NY A truly rare and remarkable offering in the heart of Orange County, Presenting an extraordinary opportunity to acquire a standout property with exceptional visibility, flexible “ OP” zoning, multiple structures, and limitless potential. Positioned on one of Chester's most highly

  Frank Muccari Cronin & Company Real Estate

  206 Greycourt Rd, Chester, NY 10918
• 

  $740,000

  Sold Nov 21, 2025

  48 Brennan Ct, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 3,063 Sq Ft
  • Built 2006

  Last Sold Summary

  • 4% Below List Price
  • $242/SF
  • 29 Days On Market

  Current Estimated Value $754,182

  Last Listing Agent Claude Brischoux Keller Williams Realty

  48 Brennan Ct, Chester, NY 10918
• 

  Est $643,845

  Not Listed For Sale

  1301 Kings Hwy, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,676 Sq Ft
  • Built 1835

  1301 Kings Hwy, Chester, NY 10918

  Last Sold Summary

  • 146 Days On Market
• 

  $330,000

  Sold Aug 15, 2025

  4503 Whispering Hills, Chester, NY 10918

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

  Last Sold Summary

  • 12% Below List Price
  • $248/SF
  • 142 Days On Market

  Current Estimated Value $343,222

  Last Listing Agent Richard Baxter Keller Williams Realty

  4503 Whispering Hills, Chester, NY 10918
• 

  Est $1,244,160

  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
• 

  $375,000

  Sold Dec 11, 2025

  4309 Whispering Hills Dr, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,355 Sq Ft
  • Built 1989

  Last Sold Summary

  • $277/SF
  • 27 Days On Market

  Current Estimated Value $374,951

  Last Listing Agent Sean Israelski Howard Hanna Rand Realty

  4309 Whispering Hills Dr, Chester, NY 10918
• 

  Est $1,388,361

  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
• 

  $299,000

  Sold Apr 07, 2026

  3120 Whispering Hills, Chester, NY 10918

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

  Last Sold Summary

  • 4% Below List Price
  • $279/SF
  • 70 Days On Market

  Current Estimated Value $301,689

  Last Listing Agent Bente Brown Hudson Premium Realty

  3120 Whispering Hills, Chester, NY 10918

Showing Results 241 - 280, Page 7 of 18