Homes in ZIP Code 10918

• 

  

  

  /25

  $375,000 Pending

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

  4116 Whispering Hills, Chester, NY 10918

  Beautifully updated 3-bedroom, 2.5-bath Dogwood model townhouse located in Whispering Hills, a desirable corner unit setting. This home offers a perfect blend of comfort and modern upgrades.Step inside to find a thoughtfully refreshed interior with remodeled and freshly painted bathrooms, along with a bright, open layout. The kitchen is equipped with a brand-new refrigerator and dishwasher,

  Michael Casarella William Raveis-New York, LLC

  4116 Whispering Hills, 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
• 

  Est $447,552 Not Listed For Sale

  33 Trotting Dr, Chester, NY 10918

  • 3 Beds
  • 1.5 Baths
  • 1,570 Sq Ft
  • Built 1968

  33 Trotting Dr, Chester, NY 10918

  Last Sold Summary

  • 18% Above List Price
  • $242/SF
  • 84 Days On Market

  • Last Sold Price $380,000
  • May 04, 2023

  Last Listing Agent Jackie Siracuse Absolute Real Estate of NY Inc
• 

  

  

  /27

  $519,000

  • 3 Beds
  • 2 Baths
  • 1,748 Sq Ft

  11 Oxford Depot, Chester, NY 10918

  Welcome to 11 Oxford Depot Rd, Chester, NY — a unique 3-bedroom, 2-bath home that perfectly blends charm, space, and modern updates. Featuring beautiful hardwood floors throughout, multiple living and entertaining areas, spacious bedrooms, updated bathrooms, and flexible bonus space ideal for a home office, playroom, or guest setup. The finished lower level adds even more versatility with

  Aneudy Rosa Keller Williams Realty

  11 Oxford Depot, 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 $695,928

  Last Listing Agent Michele Tobin Keller Williams Realty

  174 Creamery Pond Rd, Chester, NY 10918
• 

  Est $498,451 Not Listed For Sale

  62 Surrey Rd, Chester, NY 10918

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

  62 Surrey Rd, Chester, NY 10918

  Last Sold Summary

  • 2% Above List Price
  • $262/SF
  • 37 Days On Market

  • Last Sold Price $490,000
  • Jul 23, 2024

  Last Listing Agent Valerie Quinn Keller Williams Realty
• 

  

  /50

  $1,725,000

  • 4 Beds
  • 2.5 Baths
  • 3,348 Sq Ft

  20 Goshen Rd, Chester, NY 10918

  THE ULTIMATE HUDSON VALLEY LEGACY ESTATE | 53 ACRES OF UNMATCHED POTENTIAL Rarely does a property emerge that perfectly balances refined luxury living with raw, untapped opportunity. Nestled in the heart of scenic Chester, New York, 20 Goshen Road offers an expansive 53-acre canvas designed for the visionary. Whether you envision a world-class equestrian facility, a high-potential residential

  Ramanjit Dhanoa eXp Realty

  20 Goshen 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 $484,150

  Last Listing Agent Eliezer Safdie Sage Realty Center LLC

  559 Laroe Rd, Chester, NY 10918
• 

  Est $472,933 Not Listed For Sale

  30 Trotting Dr, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft
  • Built 1968

  30 Trotting Dr, Chester, NY 10918

  Last Sold Summary

  • 4% Above List Price
  • $280/SF
  • 30 Days On Market

  • Last Sold Price $455,000
  • Jun 18, 2024

  Last Listing Agent Christine Koenig Keller Williams Realty
• 

  

  /23

  $410,000

  • 2 Beds
  • 1 Bath
  • 1,026 Sq Ft

  7 Hambletonian Ave, Chester, NY 10918

  This 2 bedroom charmer with additional room offers potential 3 bedrooms. Larger than it looks - need to see. Discover the timeless charm and surprising spaciousness of this delightful carriage house, set on a property rich with character and possibility. Step inside to a generous living room where a wood burning fireplace, hardwood floors, and a large bay window create a bright, welcoming

  William Scolza HomeSmart Homes & Estates

  7 Hambletonian Ave, 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 $502,865

  Last Listing Agent Kimberly Corkum Keller Williams Realty

  16 Mari Rd, Chester, NY 10918
• 

  Est $613,943 Not Listed For Sale

  38 Park Dr, Chester, NY 10918

  • 5 Beds
  • 3.5 Baths
  • 2,770 Sq Ft
  • Built 1968

  38 Park Dr, Chester, NY 10918

  Last Sold Summary

  • 1% Above List Price
  • $218/SF
  • 28 Days On Market

  • Last Sold Price $605,000
  • Jun 28, 2024

  Last Listing Agent Patricia Hyer Howard Hanna Rand Realty
• 

  

  /38

  $350,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,272 Sq Ft

  307 Gibson Hill Rd, Chester, NY 10918

  Looking for a solid built home with great bones and a lot of space in the Warwick School District? This spacious ranch home is waiting for your modern touches. Built strong, this home is in need of some cosmetic updates but you can live in the home and enjoy it as you go. This home offers 2 bedrooms (plus a den) and a full bath. The kitchen makes every square inch count with ample storage and

  Donna Gennaro Howard Hanna Rand Realty

  307 Gibson Hill 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 $475,055

  Last Listing Agent Ryan Degnan Howard Hanna Rand Realty

  12 Mari Rd, Chester, NY 10918
• 

  Est $544,284 Not Listed For Sale

  26 Bridle Ln, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,718 Sq Ft
  • Built 1970

  26 Bridle Ln, Chester, NY 10918

  Last Sold Summary

  • 5% Below List Price
  • $332/SF
  • 23 Days On Market

  • Last Sold Price $570,000
  • Jul 30, 2024

  Last Listing Agent Valerie Quinn Keller Williams Realty
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  /32

  $319,900

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

  2820 Whispering Hills, Chester, NY 10918

  Lovely, Light and Airy 2 Bedroom 1 and 1/2 Bath Unit in Desireable Whispering Hills! Updated Kitchen and Bath, New Carpet and Freshly Painted. Downstairs has a Comfy Living Room with a Wood Burning Fireplace , Sunny Dining Room with Slider to a Patio, Convenient Galley Kitchen, Laundry Area and 1/2 Bath. Upstairs are a Spacious Primary Bedroom , Walkthrough Closet to Full Bath and a Roomy Second

  Anne Marie Scouarnec R2M Realty Inc.

  2820 Whispering Hills, 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 $374,739

  Last Listing Agent Johanna Monzon Ruballos Century 21 Full Service Realty

  2915 Whispering Hills Unit 596, Chester, NY 10918
• 

  Est $558,391 Not Listed For Sale

  77 Surrey Rd, Chester, NY 10918

  • 5 Beds
  • 2.5 Baths
  • 2,136 Sq Ft
  • Built 1968

  77 Surrey Rd, Chester, NY 10918

  Last Sold Summary

  • 4% Below List Price
  • $272/SF
  • 43 Days On Market

  • Last Sold Price $580,000
  • Dec 03, 2024

  Last Listing Agent Pedro Garcia Curasi Realty, Inc.
• 

  

  /13

  $460,000

  • 3 Beds
  • 1.5 Baths
  • 1,728 Sq Ft

  1367 Kings Hwy, Chester, NY 10918

  Historic Colonial Era Home in the Heart of Sugar Loaf, NYLocated just 60 minutes from NYCZoned Residential/CommercialStep into history with this one-of-a-kind 1,750 sq. ft. Colonial era home, where 18th-century charm meets 21st-century opportunity — right in the heart of the artisan hamlet of Sugar Loaf, NY. Original building was built in 1770, this unique property features:• One

  Mark Karten Karten Real Estate Svcs LLC

  1367 Kings Hwy, 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 $659,136

  Last Listing Agent Rosemary DelliCarpini eXp Realty

  23 Pewter Cir, Chester, NY 10918
• 

  Est $618,277 Not Listed For Sale

  81 Hambletonian Ave, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,989 Sq Ft
  • Built 2001

  81 Hambletonian Ave, Chester, NY 10918

  Last Sold Summary

  • 26% Above List Price
  • $164/SF
  • 18 Days On Market

  • Last Sold Price $490,000
  • Aug 21, 2023

  Last Listing Agent Keith Sumner John J Lease REALTORS Inc
• 

  

  /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
• 

  $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 $605,125

  Last Listing Agent Hershel Lowy Master Realty Group Inc.

  114 Old Mansion Rd, Chester, NY 10918
• 

  Est $519,492 Not Listed For Sale

  50 Hambletonian Ave, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,583 Sq Ft
  • Built 2001

  50 Hambletonian Ave, Chester, NY 10918

  Last Sold Summary

  • $328/SF
  • 180 Days On Market

  • Last Sold Price $519,000
  • May 01, 2024

  Last Listing Agent Naomi Streicher Q Home Sales
• 

  

  /24

  $362,900 Pending

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

  2203 Whispering Hills, Chester, NY 10918

  Welcome to 2203 Whispering Hills, Chester, NY — Where Comfort Meets ConvenienceThis sun-drenched end-unit townhome offers the perfect blend of space, style, and location in the sought-after Whispering Hills community.Featuring 3 spacious bedrooms and 2.5 bathrooms, this home is designed for both everyday comfort and effortless entertaining. The inviting living room is anchored by a cozy

  Marie Altieri Howard Hanna Rand Realty

  2203 Whispering Hills, 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 $665,148

  Last Listing Agent Dulce M Ferrera Keller Williams Hudson Valley

  2 Dawn Ct, Chester, NY 10918
• 

  Est $498,959 Not Listed For Sale

  7 Park Dr, Chester, NY 10918

  • 4 Beds
  • 1.5 Baths
  • 1,760 Sq Ft
  • Built 1967

  7 Park Dr, Chester, NY 10918

  Last Sold Summary

  • 1% Below List Price
  • $287/SF
  • 33 Days On Market

  • Last Sold Price $505,000
  • Nov 13, 2024

  Last Listing Agent Elena James Keller Williams Realty
• 

  

  /42

  $305,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft

  3601 Whispering Hills, Chester, NY 10918

  Welcome to effortless living in the highly sought-after Whispering Hills community! This beautifully maintained 2-bedroom, 1-bath condo with a 1-car garage offers the perfect blend of comfort, style, and convenience.Step inside to discover a warm and inviting space enhanced by custom wall detailing, stylish flooring, and a cozy fireplace, creating the perfect setting for relaxing and

  Janet Rendle Weichert Realtors

  3601 Whispering Hills, Chester, NY 10918
• 

  $612,500 Sold Sep 05, 2025

  81 Hambletonian Rd, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,938 Sq Ft
  • Built 2002

  Last Sold Summary

  • 2% Below List Price
  • $316/SF
  • 23 Days On Market

  Current Estimated Value $639,437

  Last Listing Agent Dean Diltz Keller Williams Realty

  81 Hambletonian Rd, Chester, NY 10918
• 

  Est $462,849 Not Listed For Sale

  15 Park Dr, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,724 Sq Ft
  • Built 1968

  15 Park Dr, Chester, NY 10918

  Last Sold Summary

  • 10% Above List Price
  • $244/SF
  • 41 Days On Market

  • Last Sold Price $420,000
  • Apr 05, 2024

  Last Listing Agent Krista Fontenelle-Garcia Batiz Exit Realty DKC
• 

  

  /15

  $999,000

  • 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
• 

  $338,000 Sold May 15, 2025

  4120 Whispering Hills Dr, Chester, NY 10918

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

  Last Sold Summary

  • 3% Below List Price
  • $264/SF
  • 69 Days On Market

  Last Listing Agent Joseph Paoli Howard Hanna Rand Realty

  4120 Whispering Hills Dr, Chester, NY 10918
• 

  Est $452,384 Not Listed For Sale

  52 Surrey Rd, Chester, NY 10918

  • 4 Beds
  • 2 Baths
  • 1,780 Sq Ft
  • Built 1969

  52 Surrey Rd, Chester, NY 10918

  Last Sold Summary

  • 26% Above List Price
  • $202/SF
  • 104 Days On Market

  • Last Sold Price $360,000
  • Oct 09, 2024

  Last Listing Agent Jayne M. Prechtel Keller Williams Valley Realty
• 

  /2

  $299,000

  • 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
• 

  $499,000 Sold Oct 23, 2025

  358 Bull Mill Rd, Chester, NY 10918

  • 5 Beds
  • 2.5 Baths
  • 3,120 Sq Ft
  • Built 1840

  Last Sold Summary

  • $160/SF
  • 40 Days On Market

  Current Estimated Value $535,885

  Last Listing Agent Amy Wilhelm Corcoran Baer & McIntosh

  358 Bull Mill Rd, Chester, NY 10918
• 

  Est $388,253 Not Listed For Sale

  22 Trotting Dr, Chester, NY 10918

  • 3 Beds
  • 1 Bath
  • 1,024 Sq Ft
  • Built 1968

  22 Trotting Dr, Chester, NY 10918

  Last Sold Summary

  • 5% Above List Price
  • $361/SF
  • 29 Days On Market

  • Last Sold Price $370,000
  • Dec 31, 2024

  Last Listing Agent Diane Blanton Howard Hanna Rand Realty
• 

  

  /8

  $849,900

  • 4 Beds
  • 2.5 Baths
  • 2,603 Sq Ft

  32 Mountainside Dr, Chester, NY 10918

  A RARE OPPORTUNITY to build your CUSTOM DREAM HOME on over 20 private acres in the sought-after Cooper's Ridge sub-division! This will truly be a lovely property with land, privacy and wonderful mountain views! This modern farm house cape features over 2,600 sq ft. and is completely CUSTOM and DELIVERED TURN-KEY ... build this home, or bring your own dream plans/ideas! This ONE LEVEL living

  Karen Gauvin Our House Real Estate Group

  32 Mountainside Dr, Chester, NY 10918
• 

  $425,000 Sold Oct 16, 2025

  8 Hom St, Chester, NY 10918

  • 3 Beds
  • 1.5 Baths
  • 1,410 Sq Ft
  • Built 1962

  Last Sold Summary

  • 11% Below List Price
  • $301/SF
  • 74 Days On Market

  Current Estimated Value $433,393

  Last Listing Agent Joao Rodrigues Preferred Properties Real Esta

  8 Hom St, Chester, NY 10918
• 

  Est $486,373 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

  • 6% Above List Price
  • $256/SF
  • 32 Days On Market

  • Last Sold Price $460,000
  • Jul 11, 2024

  Last Listing Agent Colin Seitz RE/MAX Benchmark Realty Group
• 

  

  /8

  $225,000

  • Land
  • 1 Acre
  • $225,000 per Acre

  34 Mountainside Dr, Chester, NY 10918

  Lovely 1-Acre lot w/MOUNTAIN VIEWS & NATURAL GAS in a beautiful newly built SUB-DIVISION. Build out this nearly completely built lovely sub-division, curb-cuts, paved road sloping lot perfect for a WALK-OUT BASEMENT and DECKS FOR BEAUTIFUL VIEWS ... FULLY APPROVED LOT, ESTABLISHED NEIGHBORHOOD, VERY COMMUTABLE location! Close to the vibrant shopping, restaurants, nightlife, shows/events at Sugar

  Karen Gauvin Our House Real Estate Group

  34 Mountainside Dr, Chester, NY 10918

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