Homes in ZIP Code 10918

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  /32

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,882 Sq Ft

  5 Roggia Rd, Chester, NY 10918

  Welcome to this spacious and versatile home nestled at a dead end st. in the desirable town of Chester. Offering an abundance of living space, this property is ideal for those seeking privacy, comfort, flexibility, and room to grow. The home features a functional layout with generously sized bedrooms, a bright and inviting living area, and a well-appointed kitchen designed for everyday living and

  

  Nazma Sooknanan

  Nazma Real Estate LLC

  (845) 606-3972

  5 Roggia Rd, Chester, NY 10918
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  /37

  $5,300 Per Month

  • 4 Beds
  • 2 Baths
  • 3,412 Sq Ft
  • House for Rent

  66 Murray Dr, Chester, NY 10918

  Welcome to Refined Living — A Contemporary Ranch renovated for Elevated Year-Round Living with ease, entertainment and privacy! Perfectly set on 1.2 acres with Mountain views just one hour from New York City, this FULLY FURNISHED and fully equipped 3,412 square-foot home provides the convenience of one level living blended with the luxury of upscale design features. The bright and open Foyer

  Tehillah Deslandes Howard Hanna Rand Realty

  66 Murray Dr, 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 $1,359,100

  Last Listing Agent Elimelech Kremer MS Realty Group USA, Inc

  10 Damian Ct, Chester, NY 10918
• 

  Est $232,549 Not Listed For Sale

  495 Laroe Rd, Chester, NY 10918

  • 3 Beds
  • Built 2025

  495 Laroe Rd, Chester, NY 10918

  Last Sold Summary

  • 38% Above List Price
  • $83/SF
  • 170 Days On Market

  • Last Sold Price $168,000
  • Dec 29, 2023

  Last Listing Agent Dylan Piazza Howard Hanna Rand 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

  (845) 328-2396

  53 Gibson Hill Rd, Chester, NY 10918
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  /20

  $15,805

  Total Monthly Price

  • 7 Beds
  • 6 Baths
  • Condo for Rent

  45 Conklingtown Rd Unit SI ID1466647P, Chester, NY 10918

  The advertised rate of $15,806/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 13, 2026.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

  (845) 599-0724

  45 Conklingtown Rd Unit SI ID1466647P, 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 $304,383

  Last Listing Agent Rebecca Matta-Candela Keller Williams Realty

  2912 Whispering Hills, Chester, NY 10918
• 

  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

  • $306/SF
  • 35 Days On Market

  • Last Sold Price $700,000
  • Jul 23, 2024

  Last Listing Agent Courtney Tablante Keller Williams Realty
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  /48

  $730,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,780 Sq Ft

  7 Park Place, Chester, NY 10918

  Welcome to your private, wooded oasis! This charming home perfectly blends convenience with comfort, featuring an ideal layout for multi-generational living or guests with two bedrooms and a full bathroom on the main floor. A cozy wood insert is the heart of the main living space, creating both warmth and a wonderful ambiance on chilly evenings. Beyond the existing bedrooms, there is additional

  

  Luanne McGann

  Century 21 Full Service Realty

  (845) 447-0221

  7 Park Place, Chester, NY 10918
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  /35

  $4,300 Per Month

  • 6 Beds
  • 4.5 Baths
  • 3,968 Sq Ft
  • House for Rent

  4 Ayr Rd, Chester, NY 10918

  Welcome to 4 Ayr Court in Chester, NY — a spacious and beautifully maintained 6-bedroom, 4-bathroom home available for rent! Nestled on a quiet street, this impressive property offers the perfect blend of space, comfort, and convenience. Step inside to find a bright and inviting interior featuring generous living areas, ideal for both everyday living and entertaining. The expansive layout

  Danielle Riggs Keller Williams Hudson Valley

  4 Ayr 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 $274,041

  Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

  2104 Whispering Hills, Chester, NY 10918
• 

  Est $371,665 Not Listed For Sale

  3815 Whispering Hills Dr, Chester, NY 10918

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

  3815 Whispering Hills Dr, Chester, NY 10918

  Last Sold Summary

  • 6% Above List Price
  • $263/SF
  • 23 Days On Market

  • Last Sold Price $350,000
  • Apr 07, 2025

  Last Listing Agent Frank Golio Howard Hanna Rand Realty
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  /38

  $327,000 Pending

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

  2323 Whispering Hills Unit 213, Chester, NY 10918

  Rare Opportunity in Whispering Hills! Discover this uniquely reimagined end-unit condo, expertly converted from a three-bedroom layout into a sprawling, sun-drenched two-bedroom retreat. This home is a masterclass in modern comfort, featuring eight brand-new Andersen windows and a matching Andersen door (2025) that perfectly frames spectacular, far-reaching horizon views. Much of the interior has

  

  Luanne McGann

  Century 21 Full Service Realty

  (845) 516-8714

  2323 Whispering Hills Unit 213, Chester, NY 10918
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  /45

  $2,490 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,053 Sq Ft
  • Townhouse for Rent

  1208 Whispering Hills, Chester, NY 10918

  Super Clean & Bright Rental in Whispering Hills. 2 Bedrooms, 1.5 Baths, 1 Car Garage with Central Air, Young Kitchen and Appliances, Laminate Flooring on 1st Floor with Laundry and updated Half Bath. Freshly Painted in 2022. Upstairs you will find Primary Bedroom with Vaulted Ceilings, Walk in Closet w/Organizers, Updated Full Bath, Skylight and Spacious Guest Room. Upstairs offers Carpeting.

  Rosalie Cook Weichert Realtors

  1208 Whispering Hills, Chester, NY 10918
• 

  $735,000 Sold Jul 21, 2025

  189 Creamery Pond Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,980 Sq Ft
  • Built 2004

  Last Sold Summary

  • 5% Above List Price
  • $247/SF
  • 19 Days On Market

  Current Estimated Value $740,086

  Last Listing Agent Patricia Brady Keller Williams Realty

  189 Creamery Pond Rd, 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

  • $258/SF
  • 50 Days On Market

  • Last Sold Price $339,000
  • Apr 01, 2025

  Last Listing Agent Annmarie Kovacs Howard Hanna Rand Realty
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  /41

  $1,159,900

  • 4 Beds
  • 5 Baths
  • 4,624 Sq Ft

  16 Lori Ln, Chester, NY 10918

  Welcome to Chester, NY, a resort-style luxury colonial set on a private 1.1-acre cul-de-sac lot in the Monroe-Woodbury area of Orange County. This custom residence delivers the space, craftsmanship, and lifestyle today's relocation and move-up buyers are searching for, with approximately 4,624 square feet, refined architectural detail, mountain views, and seamless indoor-outdoor living. From the

  

  Randolph Rogers

  eXp Realty

  (845) 493-2930

  16 Lori Ln, Chester, NY 10918
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  /26

  $2,500 Per Month

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft
  • Townhouse for Rent

  2312 Whispering Hills, Chester, NY 10918

  Welcome to the RENOVATED ASPEN MODEL END UNIT in the desirable Whispering Hills community! This stunning rental offers a blend of luxury finishes and resort-style living with an unbeatable location for NYC commuters. The unit features a Brand New Kitchen with a beautiful granite countertop and stainless-steel appliances, and a New Bathroom. Enjoy the spacious living room with a cozy fireplace and

  Elena James Keller Williams Realty

  2312 Whispering Hills, 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 $289,036

  Last Listing Agent Joseph Paoli Howard Hanna Rand Realty

  3308 Whispering Hills Dr, Chester, NY 10918
• 

  Est $512,649 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

  • 8% Above List Price
  • $327/SF
  • 45 Days On Market

  • Last Sold Price $475,000
  • Apr 22, 2025

  Last Listing Agent Juan Bautista Serhant LLC
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  /9

  $369,900

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

  3910 Whispering Hills, Chester, NY 10918

  Welcome to 3910 Whispering Hills — a refined, turnkey townhome in one of Chester’s most desirable residential enclaves. This thoughtfully appointed 3-bed, 2.5-bath home blends classic suburban elegance with low-maintenance living. Set within a mature, amenity-rich community, you’ll enjoy direct access to commuter transit, shops, and parks while savoring the quiet privacy prized by Hudson Valley

  

  Randolph Rogers

  eXp Realty

  (845) 957-9249

  3910 Whispering Hills, Chester, NY 10918
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  /10

  $2,200 Per Month

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

  82 High St Unit 5, Chester, NY 10918

  Very bright and spacious top-floor Penthouse apartment! Come see this open layout floorplan. The updated kitchen has a new stainless steel refrigerator and dishwasher. The Primary bedroom has large double closets and can accommodate a king-size bed. The living room/dining room combination is bright and sun-filled, with plenty of windows and an outside deck. You’ll appreciate the convenience of

  Lynda Hoss Weichert Realtors

  82 High St Unit 5, Chester, NY 10918
• 

  $323,500 Sold Aug 11, 2025

  98 High St, Chester, NY 10918

  • 4 Beds
  • 1.5 Baths
  • 1,360 Sq Ft
  • Built 1950

  Last Sold Summary

  • 5% Below List Price
  • $238/SF
  • 35 Days On Market

  Current Estimated Value $351,879

  Last Listing Agent Zachary Foley eXp Realty

  98 High St, Chester, NY 10918
• 

  Est $347,170 Not Listed For Sale

  1110 Whispering Hills Dr, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft
  • Built 1985

  1110 Whispering Hills Dr, Chester, NY 10918

  Last Sold Summary

  • 4% Above List Price
  • $252/SF
  • 16 Days On Market

  • Last Sold Price $335,000
  • Jun 28, 2024

  Last Listing Agent Yalitza Sepulveda Keller Williams Realty
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  /4

  $350,000

  • Land
  • 5.1 Acres
  • $68,627 per Acre

  0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918

  Very private lot in mature subdivision of large homes. Home site has been cleared and driveway base laid down. With a small amount of brush-clearing in the tree line there can be views of the valley and watershed lands.

  

  Theresa Powers

  Keller Williams Realty

  (845) 713-9754

  0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
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  /32

  $2,800 Per Month

  • 4 Beds
  • 1.5 Baths
  • 1,605 Sq Ft
  • House for Rent

  98 Main St, Chester, NY 10918

  Welcome to 98 Main St: a gracious Colonial in the center of the village of Chester!A huge "wrap-around" front porch greets you when you arrive. Once inside, you will be impressed with the "old world" charm of the stained-glass windows, dark wood trim, Hardwood floors and the pocket doors in the Living Room. Many large windows downstairs let in plenty of sunlight! Upstairs there are 4 nice

  Eveline White Hudson Valley Griffith

  98 Main St, Chester, NY 10918
• 

  $875,000 Sold Jun 13, 2025

  157 Creamery Pond Rd, Chester, NY 10918

  • 4 Beds
  • 3.5 Baths
  • 4,021 Sq Ft
  • Built 2001

  Last Sold Summary

  • 2% Above List Price
  • $218/SF
  • 17 Days On Market

  Current Estimated Value $872,070

  Last Listing Agent Carla Terranova Keller Williams Realty

  157 Creamery Pond Rd, Chester, NY 10918
• 

  Est $797,263 Not Listed For Sale

  25 Eagle Crest Way, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 2,166 Sq Ft
  • Built 2014

  25 Eagle Crest Way, Chester, NY 10918

  Last Sold Summary

  • 8% Above List Price
  • $339/SF
  • 14 Days On Market

  • Last Sold Price $735,000
  • Jun 16, 2023

  Last Listing Agent Alyssa Scancarello Howard Hanna Rand Realty
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  /16

  $900,000

  • 5 Beds
  • 3.5 Baths
  • 3,500 Sq Ft

  32 Fox Hollow Dr, Blooming Grove, NY 10918

  SINGLE LEVEL LIFESTYLE! Discover this Modern Farmhouse Style RANCH on almost 6 acres. Boasting over 3,500 finished sq. ft., this thoughtfully designed home offers 5 spacious bedrooms, one of them set up as a completely private guest quarters located above the oversized 2-car garage, perfect for hosting overnight guests. From the moment you arrive, the eye-catching details and inviting 32 ft long

  

  Julissa Amaro

  Keller Williams Hudson Valley

  (845) 581-2763

  32 Fox Hollow Dr, Blooming Grove, NY 10918
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  /37

  $3,650 Per Month

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Apartment for Rent

  408 Bull Mill Rd Unit 2, Chester, NY 10918

  ***Rare opportunity***Available April 1st for occupancy! Experience peaceful country living at 408 Bull Mill Rd, Unit 2, a Victorian-style retreat set on sprawling acreage and surrounded by nature. This 1,800 sq. ft. home offers exceptional privacy, quiet, and seclusion while providing the space and charm of a classic design. Inside, you’ll find three spacious bedrooms and two full bathrooms,

  Robert Addon Keller Williams Realty

  408 Bull Mill Rd Unit 2, 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 $637,142

  Last Listing Agent Ammar Iqbal eXp Realty

  44 Cedar Pond Ln, Chester, NY 10918
• 

  Not Listed For Sale

  68 Conklingtown Rd, Chester, NY 10918

  • 6 Beds
  • 2 Baths
  • 2,138 Sq Ft
  • Built 1950

  68 Conklingtown Rd, Chester, NY 10918

  Last Sold Summary

  • $241/SF
  • 47 Days On Market

  • Last Sold Price $515,000
  • Mar 28, 2024

  Last Listing Agent Chaim Klein MS Realty Group USA, Inc
• 

  /2

  $425,000 Open Sun 12PM - 2PM

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

  2722 Whispering Hills Unit 542, Chester, NY 10918

  New beginnings offered in this light and bright completely updated end unit featuring two car garage, brand new floors, freshly painted, update kitchen with new stainless steel appliances and so much more. Located close to major highway, NYC bus and shopping. Club house with gym, basketball and tennis courts, playgrounds and 2 inground pools. Low taxes! Town and County, $1,110.66, Village

  

  Erin Connolly-Frontino

  Artisan Realty

  (845) 932-1237

  2722 Whispering Hills Unit 542, 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 $310,344

  Last Listing Agent Kathy White Exit Realty Connections

  2812 Whispering Hills Unit 577, Chester, NY 10918
• 

  Est $463,034 Not Listed For Sale

  20 High St, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 2,488 Sq Ft
  • Built 1825

  20 High St, Chester, NY 10918

  Last Sold Summary

  • 16% Above List Price
  • $160/SF
  • 35 Days On Market

  • Last Sold Price $399,000
  • Aug 22, 2023

  Last Listing Agent George Koudounas RE/MAX Benchmark Realty Group
• 

  

  /8

  $699,990

  • 4 Beds
  • 3 Baths
  • 1,867 Sq Ft

  34 Mountainside Dr, Chester, NY 10918

  ONE LEVEL LIVING/ EASY COMMUTE- with additional space upstairs and down! ... Don't miss this beautiful TURN-KEY Arts & Crafts-style FARMHOUSE TO BE BUILT! ..... COME AND FULLY CUSTOMIZE this 4-bdrm, 3 bath, 2,106+/- sq. ft home (including bonus room)! LARGE MAIN FLOOR PRIMARY BEDROOM with ENSUITE BATH & WALK-IN CLOSET plus A SECOND MAIN FLOOR BEDROOM (NURSERY, OFFICE, CRAFT ROOM ETC.). FANTASTIC

  Karen Gauvin Our House Real Estate Group

  34 Mountainside Dr, 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 $366,973

  Last Listing Agent Erin Connolly-Frontino Artisan Realty

  4703 Whispering Hills Dr, Chester, NY 10918
• 

  Est $959,167 Not Listed For Sale

  221 Oxford Rd, Chester, NY 10918

  • 4 Beds
  • 3.5 Baths
  • 4,644 Sq Ft
  • Built 2000

  221 Oxford Rd, Chester, NY 10918

  Last Sold Summary

  • 7% Above List Price
  • $194/SF
  • 132 Days On Market

  • Last Sold Price $900,000
  • Mar 20, 2025

  Last Listing Agent Donna Brunell RE/MAX Benchmark Realty Group
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  /27

  $999,999

  • 5 Beds
  • 2.5 Baths
  • 4,772 Sq Ft

  2 Garnett Hill Rd, Chester, NY 10918

  A Private Suburban Retreat on Prestigious Garnet Hill. This Center Hall Colonial offers an exceptional residence- refined suburban living with the space, privacy, and sophistication sought by discerning buyers—just about an hour from Manhattan. Positioned on a beautifully landscaped 3+ acre property, the home features approximately over 4,700 square feet of elegant living space, offering 5

  Rachel Baruchov Platinum Realty Associates

  2 Garnett Hill Rd, Chester, NY 10918
• 

  $225,000 Sold Jun 30, 2025

  242 Meadow Ave, Chester, NY 10918

  • 4 Beds
  • 3 Baths
  • 2,519 Sq Ft
  • Built 1930

  Last Sold Summary

  • $89/SF
  • 56 Days On Market

  Current Estimated Value $330,000

  Last Listing Agent Kathleen Strong Hudson Valley Griffith

  242 Meadow Ave, Chester, NY 10918

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