Homes in ZIP Code 10918

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  /39

  $475,000

  $14K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 1,820 Sq Ft

  32 Surrey Rd, Chester, NY 10918

  Welcome to this well-maintained raised ranch in Chester, NY, offering 4 bedrooms and 1.5 bathrooms with plenty of space and flexibility. The home features hardwood floors, a bright and inviting layout, and comfortable living spaces throughout. Step outside onto the large deck overlooking a spacious backyard, perfect for outdoor entertaining, recreation, or simply enjoying the outdoors.

  

  Ammar Iqbal

  eXp Realty

  32 Surrey Rd, Chester, NY 10918
• 

  

  

  /4

  $4,200 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,894 Sq Ft
  • House for Rent

  3 Brookside Ave, Chester, NY 10918

  Come see this mixed use residential and commercial property for rent. Enjoy the benefits of working from home as you can have your business in the same home. 3 bed 3 bath home in Chester. Enjoy the ample amount of parking available, fitting well over 10 cars on your lot. Call today for a showing

  

  Joel Ayala

  HomeSmart Homes & Estates

  3 Brookside Ave, Chester, NY 10918
• 

  $685,000

  Sold Aug 14, 2026

  9 Derose Ln, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 3,100 Sq Ft
  • Built 1997

  Last Sold Summary

  • 1% Above List Price
  • $221/SF
  • 28 Days On Market

  Current Estimated Value $672,359

  Last Listing Agent Donna Gennaro Howard Hanna Rand Realty

  9 Derose Ln, Chester, NY 10918
• 

  Est $247,027

  Not Listed For Sale

  10 El Dorado Trail, Chester, NY 10918

  10 El Dorado Trail, Chester, NY 10918

  Last Sold Summary

  • 152 Days On Market

  Last Listing Agent Lisandra Rivera Keller Williams Realty
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  /48

  $1,100,000

  • 5 Beds
  • 4 Baths
  • 5,312 Sq Ft

  53 Gibson Hill Rd, Chester, NY 10918

  Tucked away on over 3 private acres, this recently renovated custom residence offers a rare blend of seclusion, craftsmanship, and elevated living. Surrounded by hundreds of acres of protected state land, the setting ensures unmatched privacy with direct access to nature, including trails that connect to the Appalachian Trail just beyond your backyard. A natural waterfall adds to the serene

  

  Ammar Iqbal

  eXp Realty

  53 Gibson Hill Rd, Chester, NY 10918
• 

  

  /20

  $15,905

  Total Monthly Price

  • 7 Beds
  • 5.5 Baths
  • Condo for Rent

  45 Conklingtown Rd Unit SI ID1466647P, Chester, NY 10918

  The advertised rate of $15,905/month is the lowest available price, based on a 30 day(s) stay with a move-in date of January 11, 2027. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

  45 Conklingtown Rd Unit SI ID1466647P, Chester, NY 10918
• 

  $1,225,000

  Sold Apr 17, 2026

  10 Damian Ct, Chester, NY 10918

  • 11 Beds
  • 6.5 Baths
  • 4,327 Sq Ft
  • Built 2004

  Last Sold Summary

  • 11% Below List Price
  • $283/SF
  • 47 Days On Market

  Current Estimated Value $1,216,706

  Last Listing Agent Elimelech Kremer MS Realty Group USA, Inc

  10 Damian Ct, Chester, NY 10918
• 

  Est $483,498

  Not Listed For Sale

  495 Laroe Rd, Chester, NY 10918

  • 3 Beds
  • Built 2025

  495 Laroe Rd, Chester, NY 10918

  Last Sold Summary

  • 170 Days On Market

  Last Listing Agent Dylan Piazza Howard Hanna Rand Realty
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  /37

  $789,900

  • 5 Beds
  • 4 Baths
  • 4,697 Sq Ft

  19 Grand View Terrace, Chester, NY 10918

  Welcome to 19 Grand View Terrace in Chester, NY, an impressive Colonial offering approximately 4,697 square feet, five bedrooms, and four full bathrooms. Set on approximately 0.42 acres, this expansive Orange County residence provides the space, comfort, and flexibility needed for everyday living, entertaining, working from home, and hosting guests.The generous interior features multiple

  

  Randolph Rogers

  eXp Realty

  19 Grand View Terrace, Chester, NY 10918
• 

  

  /20

  $2,300 Per Month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Condo for Rent

  82 High St Unit 5, Chester, NY 10918

  Fresh carpet has just been laid throughout this luminous top-floor penthouse, where an open layout and abundant sunshine create an inviting canvas for daily life. At 900 square feet, this 2-bedroom, 1-bath home balances spaciousness with a cozy, lived-in warmth. Cooks will appreciate the updated kitchen, outfitted with a new stainless steel refrigerator and dishwasher that bring both style and

  

  Ourania Pizzolato

  Weichert Realtors

  82 High St Unit 5, Chester, NY 10918
• 

  $635,000

  Sold Jun 22, 2026

  25 Sugarloaf Mountain Rd, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,954 Sq Ft
  • Built 1999

  Last Sold Summary

  • $325/SF
  • 29 Days On Market

  Current Estimated Value $630,676

  Last Listing Agent Frank Muccari Cronin & Company Real Estate

  25 Sugarloaf Mountain Rd, Chester, NY 10918
• 

  Est $750,246

  Not Listed For Sale

  303 Sugarloaf Mountain Rd, Chester, NY 10918

  • 4 Beds
  • 3 Baths
  • 2,287 Sq Ft
  • Built 2024

  303 Sugarloaf Mountain Rd, Chester, NY 10918

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Courtney Tablante Keller Williams Realty
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  /46

  $949,000

  • 3 Beds
  • 3 Baths
  • 3,591 Sq Ft

  38 Shore Dr, Blooming Grove, NY 10914

  Wake up to vacation every single day at this stunning waterfront home, set on 1.1 acres with 200 feet of Tomahawk Lake frontage.38 Shore Drive is a destination in itself. Launch your boat or kayak from your private dock, spend the afternoon by the inground pool, or simply take in the spectacular lake views that make every day feel like a getaway. From morning coffee overlooking the water

  

  Alison Orlando

  KW Hudson Valley United

  38 Shore Dr, Blooming Grove, NY 10914
• 

  

  /12

  $2,100 Per Month

  • 2 Beds
  • 1 Bath
  • 940 Sq Ft
  • Condo for Rent

  53 Main St Unit 4, Chester, NY 10918

  Property Id: 2791335 Welcome to your new home at 53 Main St in Chester, NY! This single unit offers modern amenities including oven, microwave, washer, dryer, and more. Enjoy the convenience. building. No pets allowed. Rent for $2100/month starting 09/01/2026. Don't miss out on this fantastic opportunity! No Smoking ,credit and reference checked .proof of income. Heat and

  53 Main St Unit 4, Chester, NY 10918
• 

  $320,000

  Sold Mar 11, 2026

  2912 Whispering Hills, Chester, NY 10918

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

  Last Sold Summary

  • 5% Above List Price
  • $295/SF
  • 19 Days On Market

  Current Estimated Value $313,526

  Last Listing Agent Rebecca Matta-Candela Keller Williams Realty

  2912 Whispering Hills, Chester, NY 10918
• 

  Est $1,294,943

  Not Listed For Sale

  154 Hambletonian Rd, Chester, NY 10918

  • 4 Beds
  • 3.5 Baths
  • 4,350 Sq Ft
  • Built 2013

  154 Hambletonian Rd, Chester, NY 10918

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Claudia Lepore Keller Williams Realty
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  /49

  $700,000

  • 4 Beds
  • 2.5 Baths
  • 3,296 Sq Ft

  13 Bianca Blvd, Chester, NY 10918

  Gracious Colonial home features the best of the traditional style with the appeal of a contemporary open floor plan in the kitchen - family room area. Meticulously maintenance and stylish updates create easy living spaces that are great for daily relaxation as well as entertainment. The full-length deck, large seating area around the fire pit and expansive yard provide outdoor areas to relax,

  Theresa Powers

  Keller Williams Realty

  13 Bianca Blvd, Chester, NY 10918
• 

  

  /6

  $1,800 Per Month

  • 1 Bed
  • 1 Bath
  • House for Rent

  33 Schnabel Rd, Chester, NY 10918

  Property Id: 2620401 One bedroom and one living room with private entrance private bathroom and Landry room and parking space

  33 Schnabel Rd, Chester, NY 10918
• 

  $710,000

  Sold Sep 05, 2026

  2 Gate Way, Chester, NY 10918

  • 5 Beds
  • 2.5 Baths
  • 3,200 Sq Ft
  • Built 2022

  Last Sold Summary

  • $222/SF
  • 2 Days On Market

  Current Estimated Value $572,366

  Last Listing Agent Moshe Kaufman MK Realty Inc

  2 Gate Way, Chester, NY 10918
• 

  Est $353,756

  Not Listed For Sale

  2402 Whispering Hills Dr, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • Built 1987

  2402 Whispering Hills Dr, Chester, NY 10918

  Last Sold Summary

  • 23 Days On Market

  Last Listing Agent Kewin Garabito eXp Realty
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  /36

  $749,900

  • 4 Beds
  • 4 Baths
  • 3,080 Sq Ft

  20 Mountainside Dr, Chester, NY 10918

  20 Mountainside Drive, Chester, NY offers a spacious Colonial-style single-family home on approximately 1.6 acres with 4 bedrooms, 2 full baths, 2 half baths, 10 total rooms, and approximately 3,080 sq. ft. of above-ground living space. Built in 2021, this Chester residence features central cooling, gas heat, a full basement, fireplace, covered porch, patio, and Attached garage. Located in Orange

  

  Randolph Rogers

  eXp Realty

  20 Mountainside Dr, Chester, NY 10918
• 

  

  /38

  $6,000 Per Month

  • 4 Beds
  • 2.5 Baths
  • 3,348 Sq Ft
  • House for Rent

  20 Goshen Rd, Chester, NY 10918

  Rare rental opportunity to occupy a premier estate in Chester. This property is perfectly suited for those seeking a self-sufficient lifestyle without sacrificing modern luxury. The 4-bedroom, 3-bath custom home is complemented by expansive grounds crisscrossed with miles of private horse trails and a thriving, mature fruit orchard. Practicality meets scale with an infrastructure designed for

  Ramanjit Dhanoa eXp Realty

  20 Goshen Rd, Chester, NY 10918
• 

  $260,000

  Sold Mar 11, 2026

  2104 Whispering Hills, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft
  • Built 1984

  Last Sold Summary

  • 13% Below List Price
  • $195/SF
  • 24 Days On Market

  Current Estimated Value $283,151

  Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

  2104 Whispering Hills, Chester, NY 10918
• 

  Not Listed For Sale

  4501 Whispering Hills Dr, Chester, NY 10918

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

  4501 Whispering Hills Dr, Chester, NY 10918

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Bernadette Giordano Howard Hanna Rand Realty
• 

  

  /35

  $349,999

  $50K PRICE DROP Pre-Foreclosure

  • 4 Beds
  • 1.5 Baths
  • 1,560 Sq Ft

  241 Meadow Ave, Chester, NY 10918

  Discover the timeless charm and endless potential of this classic Colonial farmhouse, ideally situated on just under one level acre in the heart of Chester, NY. Offering approximately 1,560 square feet of living space, this 4 bedroom, 2 bath home is filled with character and craftsmanship.Step inside to find original hardwood floors, a cozy wood-burning stove, and an artistic, welcoming

  

  Chativa Bowen

  Keller Williams Realty

  241 Meadow Ave, Chester, NY 10918
• 

  

  /7

  $1,750 Per Month

  • 2 Beds
  • 1 Bath
  • 696 Sq Ft
  • Property for Rent

  222 Lehigh Ave, Chester, NY 10918

  Charming. Updated. Affordable.Welcome to this beautifully updated 2-bedroom, 1-full bath trailer, offering comfortable living with modern finishes throughout. Step inside to a bright, open living area designed for both relaxing and entertaining.The stunning white kitchen features elegant quartz countertops with quartz backsplash, beautiful cabinetry, and plenty of workspace, creating

  Roxanne Hartman Timothy W. Kramer

  222 Lehigh Ave, Chester, NY 10918
• 

  $290,000

  Sold Apr 09, 2026

  3308 Whispering Hills Dr, Chester, NY 10918

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft
  • Built 1984

  Last Sold Summary

  • 3% Below List Price
  • $271/SF
  • 39 Days On Market

  Current Estimated Value $294,428

  Last Listing Agent Joseph Paoli Howard Hanna Rand Realty

  3308 Whispering Hills Dr, Chester, NY 10918
• 

  Est $309,698

  Not Listed For Sale

  4401 Whispering Hills Dr, Chester, NY 10918

  • 2 Beds
  • 1 Bath
  • 1,118 Sq Ft
  • Built 1989

  4401 Whispering Hills Dr, Chester, NY 10918

  Last Sold Summary

  • 30 Days On Market

  Last Listing Agent Annmarie Kovacs Howard Hanna Rand Realty
• 

  

  /50

  $990,000

  Open Sat 12PM - 2PM $10K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,955 Sq Ft

  1 Oakland Ave, Chester, NY 10918

  Welcome to Brook Farm - Village of Chester, New York - Circa 1851 - 6.8 Acres.There's a moment, just after you turn onto Main Street and the house comes into view above the lawn, when you understand that this is not an ordinary property. The covered porch stretches wide across the front, the slate roof catches the afternoon light, and the whole thing sits there with the quiet confidence of

  

  Christina Rowan

  Howard Hanna Rand Realty

  1 Oakland Ave, Chester, NY 10918
• 

  

  /27

  $3,250 Per Month

  • 4 Beds
  • 1 Bath
  • 2,277 Sq Ft
  • House for Rent

  7 Ruscitti Dr, Chester, NY 10918

  Welcome to your spacious new home at 7 Ruscitti Drive in charming Chester, NY! This bright and airy single-family home features 4 generous bedrooms, a full bath, and a large basement with plenty of extra storage space, giving everyone room to relax, work, or stay organized. Best of all, pets are warmly welcomed! Located in a quiet, friendly neighborhood in the heart of the Hudson Valley, you’ll

  Abraham Schwartz Priority Management

  7 Ruscitti Dr, Chester, NY 10918
• 

  $610,000

  Sold Mar 12, 2026

  44 Cedar Pond Ln, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,876 Sq Ft
  • Built 1991

  Last Sold Summary

  • 2% Above List Price
  • $325/SF
  • 48 Days On Market

  Current Estimated Value $656,220

  Last Listing Agent Ammar Iqbal eXp Realty

  44 Cedar Pond Ln, Chester, NY 10918
• 

  Not Listed For Sale

  4120 Whispering Hills Dr, Chester, NY 10918

  • 2 Beds
  • 1.5 Baths
  • 1,282 Sq Ft
  • Built 1989

  4120 Whispering Hills Dr, Chester, NY 10918

  Last Sold Summary

  • 69 Days On Market

  Last Listing Agent Joseph Paoli Howard Hanna Rand Realty
• 

  

  /50

  $549,000

  • 4 Beds
  • 2 Baths
  • 2,824 Sq Ft

  147 Main St, Chester, NY 10918

  Bring your vision to **147 Main Street in the Village of Chester**. Zoned **Duplex with Neighborhood Business use**, this spacious property offers an excellent opportunity for investors, business owners or buyers looking to renovate and create value.The property features multiple living areas, four bedrooms, a large kitchen with center island, one full bathroom, a half bathroom, laundry

  

  Samantha Ortiz

  Howard Hanna Rand Realty

  147 Main St, Chester, NY 10918
• 

  $320,000

  Sold Feb 13, 2026

  2812 Whispering Hills Unit 577, Chester, NY 10918

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft
  • Built 1984

  Last Sold Summary

  • 10% Above List Price
  • $295/SF
  • 22 Days On Market

  Current Estimated Value $316,294

  Last Listing Agent Kathy White Exit Realty Connections

  2812 Whispering Hills Unit 577, Chester, NY 10918
• 

  Not Listed For Sale

  3111 Whispering Hills Dr, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • Built 1987

  3111 Whispering Hills Dr, Chester, NY 10918

  Last Sold Summary

  • 50 Days On Market

  Last Listing Agent Annmarie Kovacs Howard Hanna Rand Realty
• 

  

  /42

  $565,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,724 Sq Ft

  1 Bell Way, Chester, NY 10918

  COLOR AT THE CURB. A POP OF PERSONALITY AT THE DOOR. FROM THE FIRST HELLO, THIS ONE FEELS LIKE HOME.Before you even step inside, this home makes a memorable first impression. The perennial garden, natural stone walkway, and inviting front door adds just the right pop of color and personality, setting the tone for a home that feels fresh, welcoming and anything but cookie-cutter. Tucked away

  

  Christina Rowan

  Howard Hanna Rand Realty

  1 Bell Way, Chester, NY 10918
• 

  $382,000

  Sold Jan 12, 2026

  4703 Whispering Hills Dr, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft
  • Built 1991

  Last Sold Summary

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

  Current Estimated Value $372,671

  Last Listing Agent Erin Connolly-Frontino Artisan Realty

  4703 Whispering Hills Dr, Chester, NY 10918
• 

  Est $503,557

  Not Listed For Sale

  397 Bellvale Rd, Chester, NY 10918

  • 2 Beds
  • 2 Baths
  • 1,452 Sq Ft
  • Built 1983

  397 Bellvale Rd, Chester, NY 10918

  Last Sold Summary

  • 45 Days On Market

  Last Listing Agent Juan Bautista Serhant LLC
• 

  

  /18

  $399,000

  • Land
  • 46 Acres
  • $8,674 per Acre

  492 Black Meadow Rd, Chester, NY 10918

  Rare opportunity to own approximately 46 acres in the desirable Black Meadow Road area of Chester, New York. Tucked privately behind a subdivision entrance at the end of a cul-de-sac, this parcel offers a peaceful natural setting surrounded by mature woods, wetlands, scenic surroundings, and abundant wildlife.Ideal for recreational use including hiking, hunting, nature walks, bird

  

  Ewa Kusmierek

  eXp Realty

  492 Black Meadow Rd, Chester, NY 10918
• 

  

  /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 $475,166

  Last Listing Agent Nicola Friedman Windsor Realty Services, Inc.

  39 Shore Dr, Blooming Grove, NY 10914

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