Chester, NY Homes

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  $509,999

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  391 Bull Mill Rd, Chester, NY 10918

  Motivated Seller!! Welcome home to this storybook setting, where a majestic weeping cherry blossom greets you with it's graceful cascade of blossoms each spring. This beautifully preserved historical farmhouse set on 1.7 acres along a scenic country road just down the lane from a local farm where the soft "mooing" adds to the peaceful rural charm. Sitting pretty on a corner lot with a circular

  

  Alexandra Zinko

  Century 21 Realty Center

  (845) 412-9860

  391 Bull Mill Rd, Chester, NY 10918
• Explore Chester

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  /20

  $8,435 per month

  • 7 Beds
  • 5.5 Baths
  • Condo for Rent

  45 Conklingtown Rd Unit ID1056815P, Chester, NY 10918

  Escape to this luxurious 7-bedroom home in Chester, NY, designed for ultimate relaxation. This spacious home features stylish furnishings and elegant touches throughout, making you feel at home.This home boasts upscale outdoor spaces with a sparkling pool, porch lounge, and covered dining area. Inside, enjoy a game room with a pool table, a spacious dining room, a gas fireplace, a powder

  45 Conklingtown Rd Unit ID1056815P, Chester, NY 10918
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  $43,000 Sold Oct 31, 2025

  L17 Vanderwalker Rd, Chester, NY 12817

  • Land
  • 4 Acres
  • $10,750 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 5 Days On Market

  Last Listing Agent Zachary Layton Four Seasons Sotheby's International Realty

  L17 Vanderwalker Rd, Chester, NY 12817
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  Not Listed For Sale

  L26 Marina Rd Unit Subdivision Lot 3, Chester, NY 12817

  L26 Marina Rd Unit Subdivision Lot 3, Chester, NY 12817
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  $299,999

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

  4508 Whispering Hills, Chester, NY 10918

  Welcome to 4508 Whispering Hills, a well-maintained and thoughtfully updated 2-bedroom, 1.5-bath home offering comfort and convenience. Recent upgrades include an updated kitchen and bathrooms, hardwood floors, a newer sliding glass door, garage door with opener, and an upgraded furnace, providing peace of mind for the next owner. The home features a one-car garage and a practical layout that

  

  Ammar Iqbal

  eXp Realty

  (845) 668-4564

  4508 Whispering Hills, Chester, NY 10918
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  /36

  $3,800 per month

  • 4 Beds
  • 3 Baths
  • 2,457 Sq Ft
  • House for Rent

  118 Booth Rd, Chester, NY 10918

  A tastefully, restored 2-story, 4BR, 3BTH, bi-level style home set on over 3+ prestine acres at the end of a quaint cul-de-sac. Enjoy the large open fields, secluded from all the stresses of the day. Plenty of room for an athletic field, in-ground pool or just a peaceful sanctuary. The exquisite touches throughout add to its elegance, from high-end ceramics to restored oak floors. The

  Chris Scibelli Keller Williams Realty

  118 Booth Rd, Chester, NY 10918
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  $900,000 Sold Mar 20, 2025

  221 Oxford Rd, Chester, NY 10918

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

  Last Sold Summary

  • 18% Below List Price
  • $194/SF
  • 132 Days On Market

  Current Estimated Value $937,872

  Last Listing Agent Donna Brunell RE/MAX Benchmark Realty Group

  221 Oxford Rd, Chester, NY 10918
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  Est $199,824 Not Listed For Sale

  495 Laroe Rd, Chester, NY 10918

  495 Laroe Rd, Chester, NY 10918
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  $559,000 Pending

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

  12 Juniper Ln, Monroe, NY 10950

  Welcome to this 4-bedroom, 3 full bath raised ranch offering a flexible and spacious layout designed for comfortable everyday living. Hardwood floors run throughout the main level, adding warmth and character to the home's living spaces. The primary bedroom features a private en-suite bath, creating a quiet and comfortable retreat. Three additional bedrooms provide plenty of room for family,

  

  Shaylene Neumann

  Houlihan Lawrence Inc.

  (329) 208-1641

  12 Juniper Ln, Monroe, NY 10950
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  $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
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  $415,000 Sold Apr 08, 2025

  2 Fields Ln, Chester, NY 10918

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

  Last Sold Summary

  • 4% Above List Price
  • $159/SF
  • 24 Days On Market

  Current Estimated Value $468,937

  Last Listing Agent Margaret Galatro ARC Realty 1 in Sales

  2 Fields Ln, Chester, NY 10918
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  Not Listed For Sale

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

  303 Sugarloaf Mountain Rd, Chester, NY 10918

  303 Sugarloaf Mountain Rd, Chester, NY 10918
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  $650,000 Pending

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

  23 Pewter Cir, Chester, NY 10918

  Welcome to this beautifully maintained 2,318 sq ft Colonial located in the desirable Chester/Sugar Loaf area within the Warwick Valley School District. Set on a landscaped .32-acre lot, this home offers a warm and inviting layout with generous space, natural light, and an ideal setting for comfortable everyday living. The first floor features hardwood flooring and a thoughtful floor plan designed

  

  Rosemary DelliCarpini

  eXp Realty

  (845) 660-8249

  23 Pewter Cir, Chester, NY 10918
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  /7

  $1,700 per month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Apartment for Rent

  8 Main St, Chester, NY 10918

  Located in Historic Downtown Chester. This is a 1 bedroom apartment located on the 2nd floor. Open floor plan with exposed brick walls and lots of natural light. Walking distance to shops, restaurants, brewery, and the Heritage Trail. Close to public transportation and Route 17.

  Jeanmarie Valentin HomeSmart Homes & Estates

  8 Main St, Chester, NY 10918
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  $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 $745,531

  Last Listing Agent Patricia Brady Keller Williams Realty

  189 Creamery Pond Rd, Chester, NY 10918
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  Est $294,995 Not Listed For Sale

  5 Heidi Ln, Chester, NY 10918

  5 Heidi Ln, Chester, NY 10918
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  $515,000 Pending

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

  25 High St, Chester, NY 10918

  25 High Street is back on the market and newly refreshed, making this Victorian gem more inviting than ever. Brimming with character and ready for your personal touch, this special home welcomes you with original wide-plank wood floors throughout—preserved under carpeting to maintain their timeless authenticity and warmth. Entertain in style in the bright, modern kitchen or host memorable

  

  Alicia Goldman

  Christie's Int. Real Estate

  (845) 599-0487

  25 High St, Chester, NY 10918
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  $1,600 per month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Apartment for Rent

  13 Jackson St Unit C, Chester, NY 10918

  Experience the charm of downtown Chester in this warm and welcoming 1 bed, 1 bath apartment. Just a short stroll to the Heritage Trail, local eateries, and cozy cafés, this location puts you right at the heart of village living. This unit includes private off-street parking and a small patio area—perfect for enjoying your morning coffee or some fresh air. This unit is situated on quiet Jackson

  Brooke Lorimer Keller Williams Realty

  13 Jackson St Unit C, Chester, NY 10918
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  $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 $348,591

  Last Listing Agent Zachary Foley eXp Realty

  98 High St, Chester, NY 10918
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  Est $116,004 Not Listed For Sale

  30 Mount Ridge Ct, Monroe, NY 10950

  30 Mount Ridge Ct, Monroe, NY 10950
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  $600,000 Pending

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

  44 Cedar Pond Ln, Chester, NY 10918

  Set on 2.5 private acres within the Warwick Valley School District, this inviting contemporary log home captures the warmth, character, and tranquility that make log-home living so special. Surrounded by rolling hills, open meadows, and wooded scenery, the property offers peaceful country views from every angle, while being just minutes from the artisan village of Sugar Loaf. Inside, the main

  

  Ammar Iqbal

  eXp Realty

  (845) 415-4374

  44 Cedar Pond Ln, Chester, NY 10918
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  $2,300 per month

  • 3 Beds
  • 1 Bath
  • 866 Sq Ft
  • House for Rent

  2 Oxford Depot, Chester, NY 10918

  Well-maintained 3-bed Chester, NY....This home is meticulous and move-in ready! Rent this home and be close to everything! Just a few minutes to the highway, close to commuter bus train, and less than an hour to GWB! Popular heritage trails are 100 yards away for biking, walking, and running. Additional Information: Heating Fuel Oil Below Ground,

  Mordechai Ungar HFA Realty Group

  2 Oxford Depot, Chester, NY 10918
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  $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 $887,394

  Last Listing Agent Carla Terranova Keller Williams Realty

  157 Creamery Pond Rd, Chester, NY 10918
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  Est $349,989 Not Listed For Sale

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

  1110 Whispering Hills Dr, Chester, NY 10918

  1110 Whispering Hills Dr, Chester, NY 10918
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  /30

  $290,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft

  2812 Whispering Hills Unit 577, Chester, NY 10918

  Motivated sellers. Welcome to Whispering Hills, one of the most sought-after communities in the area with resort style amenities and unbeatable commuter convenience. Picture yourself coming home to this beautiful space. The large living room opens to sliding glass doors that lead out to your private deck, the perfect spot to unwind after a long day. Cathedral ceilings create an open, airy feel,

  

  Kathy White

  Exit Realty Connections

  (845) 390-2310

  2812 Whispering Hills Unit 577, Chester, NY 10918
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  /9

  $2,000 per month

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • House for Rent

  1396 Kings Hwy, Chester, NY 10918

  Newly renovated 3 bedroom unit located in the heart of Sugar Loaf and within the Warwick School District. This second-floor walkup features a bright white kitchen with stainless steel appliances, including an in-unit washer/drier, and offers a large private balcony with scenic views of Sugar Loaf Mountain. The unit is situated above a restaurant; music may be audible as late as 11 PM on Friday

  Roxanne Hartman Timothy W. Kramer

  1396 Kings Hwy, Chester, NY 10918
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  $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

  Last Listing Agent Erin Connolly Artisan Realty

  4703 Whispering Hills Dr, Chester, NY 10918
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  Est $828,800 Not Listed For Sale

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

  25 Eagle Crest Way, Chester, NY 10918

  25 Eagle Crest Way, Chester, NY 10918
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  $730,000

  • 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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  $1,900 per month

  • 1 Bed
  • 1 Bath
  • 1,200 Sq Ft
  • Apartment for Rent

  347 Bellvale Rd, Chester, NY 10918

  Move-in ready rental in beautiful Warwick, NY. This spacious apartment-style home is nestled in a peaceful countryside setting and is available for a full-time tenant. Enjoy comfortable one-level living with scenic nature views in every direction.Upon entry, you are welcomed by a large foyer that leads into a sun-soaked living room, perfect for relaxing or entertaining. Just off the living

  Alissa Taylor-Vetell Keller Williams Realty

  347 Bellvale Rd, Chester, NY 10918
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  $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 $319,383

  Last Listing Agent Kathleen Strong Hudson Valley Griffith

  242 Meadow Ave, Chester, NY 10918
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  Not Listed For Sale

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

  68 Conklingtown Rd, Chester, NY 10918

  68 Conklingtown Rd, Chester, NY 10918
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  $674,999 Pending

  • 5 Beds
  • 2.5 Baths
  • 3,115 Sq Ft

  507 Bull Mill Rd, Chester, NY 10918

  Welcome to this beautifully maintained colonial with a charming wrap-around front porch, set on 1.5 private acres within the sought-after Monroe-Woodbury School District. Offering over 3,100 square feet of living space, this 5-bedroom, 2.5-bath home blends timeless style with thoughtful design. Step inside the two-story foyer and you’ll find a bright, flowing layout designed for both everyday

  

  Alison Orlando

  Keller Williams Hudson Valley

  (845) 385-2902

  507 Bull Mill Rd, Chester, NY 10918
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  $2,450 per month

  • 2 Beds
  • 1.5 Baths
  • 1,086 Sq Ft
  • Condo for Rent

  1107 Whispering Hills, Chester, NY 10918

  Great 2bd 1.5ba Townhouse style unit in Whispering Hills. Living room w/ fireplace open to the dining room. Laminate floors throughout. We’ll appointed kitchen with newer cabinets and SS appliances. Vaulted Ceilings in the Master Bedroom with walk-in closet and organizer. Central air, TWO car garage, Washer/Dryer! This complex offers 2 community pools, clubhouse, tennis/basketball courts and gym.

  Joseph Trifono HomeSmart Homes & Estates

  1107 Whispering Hills, Chester, NY 10918
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  $567,000 Sold Feb 12, 2025

  6 Railroad Ave, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,922 Sq Ft
  • Built 1850

  Last Sold Summary

  • 5% Below List Price
  • $194/SF
  • 63 Days On Market

  Current Estimated Value $577,435

  Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

  6 Railroad Ave, Chester, NY 10918
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  Not Listed For Sale

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

  20 High St, Chester, NY 10918

  20 High St, Chester, NY 10918
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  $899,000

  • 4 Beds
  • 2.5 Baths
  • 2,722 Sq Ft

  5 Gabriels Dr, Chester, NY 10918

  Exquisite 4 bedroom 3 bath colonial , timeless grandeur meets modern luxury nestled gracefully on a private cul de sac. Amidst meticulously manicured grounds, this colonial style home offers an unparalleled blend of classic elegance and contemporary comfort, from the moment you approach the stately wrought iron fenced property and are greeted by a wrap around porch, you are welcomed by a grand

  Claudia Lepore Keller Williams Realty

  5 Gabriels Dr, Chester, NY 10918
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  $3,850 per month

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

  408 Bull Mill Rd Unit 2, Chester, NY 10918

  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, thoughtfully laid out to maximize comfort and natural light.

  Robert Addon Keller Williams Realty

  408 Bull Mill Rd Unit 2, Chester, NY 10918
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  $899,999 Sold Jun 18, 2025

  29 Meadow Ave, Chester, NY 10918

  • 4 Beds
  • 3 Baths
  • 3,167 Sq Ft
  • Built 2023

  Last Sold Summary

  • 8% Below List Price
  • $284/SF
  • 163 Days On Market

  Current Estimated Value $364,868

  Last Listing Agent Nancy Sardo BHG Real Estate Green Team

  29 Meadow Ave, Chester, NY 10918
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  Est $562,287 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,771 Sq Ft

  47 Maple Ave, Chester, NY 10918

  47 Maple Ave, Chester, NY 10918

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