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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  /29

  $8,970 per month

  • 7 Beds
  • 5.5 Baths
  • Condo for Rent

  45 Conklingtown Rd Unit ID1056815P, Chester, NY 10918

  Escape to this luxurious 7-bedroom retreat in the heart of Chester, NY! Designed for ultimate relaxation, the home boasts upscale outdoor spaces with a sparkling pool, porch lounge, and covered dining area. Inside, enjoy stylish furnishings, a chic home office, and elegant touches throughout. A game room with a pool table adds a fun element, making this the perfect mix of comfort and

  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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  Est $820,095 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,328 Sq Ft

  15 Eagle Crest Way, Chester, NY 10918

  15 Eagle Crest Way, 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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  $2,150 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

  12 Railroad Ave Unit Floor 2, Chester, NY 10918

  Is there a 2-bed apartment in Chester Village with parking, outdoor space, and walkable access to downtown? This newly refreshed second floor rental offers approximately 1,000 square feet, a private covered deck, garage parking, and an updated kitchen, all set in Historic Downtown Chester near dining, shops, and the Heritage Trail. This spacious apartment at 12 Railroad Avenue, Unit Floor 2

  Geoffrey Green BHG Real Estate Green Team

  12 Railroad Ave Unit Floor 2, 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 $254,476 Not Listed For Sale

  495 Laroe Rd, Chester, NY 10918

  495 Laroe Rd, Chester, NY 10918
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  $369,000 Pending

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

  4703 Whispering Hills Dr, Chester, NY 10918

  Rare end unit in Whispering Hills. 3 bedrooms, 2 1/2 bathroom in spectacular location in the highly sought after Chester School district. Updated kitchen with stainless steel appliances and sliders to private patio. Located close to major highway, NYC bus and shopping. Club house with gym, basketball and tennis courts, playgrounds and 2 inground pools. Attached 2 car garage. Low taxes!

  

  Erin Connolly

  Artisan Realty

  (845) 206-4461

  4703 Whispering Hills Dr, Chester, NY 10918
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  $3,200 per month

  • 4 Beds
  • 2 Baths
  • House for Rent

  3 Tulip Ln, Monroe, NY 10950

  Property Id: 2288513Your Ideal Home Awaits;Section 8 Accepted! Enjoy the comfort of this stunning apartment, featuring 4 spacious bedrooms and 2 full baths. Bright, Airy Spaces;Key Features• 4 generous bedrooms• 2 full bathrooms• Large deck• Convenient location near amenitiesExperience the perfect balance of space and style in your new home.Call to

  3 Tulip Ln, Monroe, NY 10950
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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 $485,962

  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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  $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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  $3,300 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
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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 $748,116

  Last Listing Agent Patricia Brady Keller Williams Realty

  189 Creamery Pond Rd, Chester, NY 10918
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  Est $295,413 Not Listed For Sale

  5 Heidi Ln, Chester, NY 10918

  5 Heidi Ln, Chester, NY 10918
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  /42

  $559,000

  • 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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  /16

  $2,950 per month

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft
  • Townhouse for Rent

  4321 Whispering Hills, Chester, NY 10918

  This is a beautiful rental, If you are looking to rent, here it is!! plenty of room,3 bedrooms 2.5 baths, 2 car garage, close to amenities, new bathrooms, close to shopping, close to major highways and rail for commuters. Freshly painted, new carpets, hardwood floors redone. Must see if you are looking to rent!!! Additional Information: ParkingFeatures:1 Car Attached.

  Dan Neil Field Pointe Realty LLC

  4321 Whispering Hills, 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 $349,621

  Last Listing Agent Zachary Foley eXp Realty

  98 High St, Chester, NY 10918
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  Est $115,710 Not Listed For Sale

  30 Mount Ridge Ct, Monroe, NY 10950

  30 Mount Ridge Ct, Monroe, NY 10950
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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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  /12

  $2,450 per month

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

  3607 Whispering Hills Unit 295, Chester, NY 10918

  Don't miss the opportunity to lease this picture-perfect, beautifully renovated townhome featuring two bedrooms and 1.5 brand-new bathrooms. The residence boasts a brand-new kitchen outfitted with stainless steel appliances and includes a dedicated laundry room with a new washer and dryer. Upstairs, the space is brightened by a cathedral ceiling and skylight, adding an airy and luxurious feel.

  Nikki Grzegorzewski Keller Williams Realty

  3607 Whispering Hills Unit 295, 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 $893,242

  Last Listing Agent Carla Terranova Keller Williams Realty

  157 Creamery Pond Rd, Chester, NY 10918
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  Est $359,018 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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  /34

  $689,900 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,092 Sq Ft

  2 Dawn Ct, Chester, NY 10918

  Spectacular 4 bedrooms, 2.5 bathrooms colonial in the very desirable Sugarloaf Heights. This magnificent home offers heavenly views right from your rear deck. You never have to leave home when you can step outside and enjoy your own personal refuge with a fully fenced-in yard that brings privacy to your in-ground pool. Home offers many recent upgrades which include updated kitchen, recess

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (845) 203-6068

  2 Dawn Ct, Chester, NY 10918
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  $2,800 per month

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft
  • Townhouse for Rent

  2910 Whispering Hills Dr, Chester, NY 10918

  Welcome to Whispering Hills Chester's highly desirable condo community offering comfort, convenience, and lifestyle! This spacious 3-bedroom, 2.5-bathroom unit features soaring ceilings, generous room sizes, and excellent storage throughout. The stylish kitchen boasts brand-new appliances and modern two-tone cabinets, creating a sleek and inviting space that opens to a private deck ideal for

  Nathen Singer MK Realty Inc

  2910 Whispering Hills Dr, 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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  Est $827,335 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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  /28

  $515,000

  • 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) 244-4823

  25 High St, Chester, NY 10918
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  $3,950 per month

  • 4 Beds
  • 2.5 Baths
  • 2,840 Sq Ft
  • House for Rent

  948 Craigville Rd, Chester, NY 10918

  Amazingly beautiful 1850's renovated home and horse property. Over 11 acres of land with approx. 3.5 acres of 4-board fenced-in pasture including 2 run-in sheds with access to water. The house is in excellent condition with high-efficiency radiant heated floors, central a/c and natural gas! There is also a stand-by generator. Enjoy beautiful wide-plank wood floors, meticulously maintained and

  Layla Rose Boyles Century 21 Realty Center

  948 Craigville Rd, 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 $572,658

  Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

  6 Railroad 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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  /29

  $369,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,585 Sq Ft

  252 Heritage Ln, Monroe, NY 10950

  Welcome to this beautifully maintained 3 bedroom, 2.5-bath townhouse located in a highly sought after community within the Monroe-Woodbury School District. This move-in ready home features an open-concept main level with a spacious living room and kitchen area, perfect for entertaining. Enjoy the convenience of private in-unit laundry and assigned parking, with plenty of additional parking

  Brenda Wiley Howard Hanna Rand Realty

  252 Heritage Ln, Monroe, NY 10950
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  /11

  $2,650 per month

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

  1418 Whispering Hills, Chester, NY 10918

  Looking for a 2 car garage? Look no further! Welcome to the highly desirable Whispering Hills Community in Chester School District. This rental features 2 bedrooms, 1.5 bathrooms, and a two car garage for extra storage. The first level offers a cozy fireplace in your spacious living room, dining area with sliding glass doors to your private patio, kitchen, half bath, and washer/ dryer. You will

  Erin Hansford Stonewall Realty Group LLC

  1418 Whispering Hills, 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 $365,562

  Last Listing Agent Nancy Sardo BHG Real Estate Green Team

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

  • 2 Beds
  • 1 Bath
  • 3,182 Sq Ft

  63 Main St, Chester, NY 10918

  63 Main St, Chester, NY 10918
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  /33

  $1,375,000 Pending

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

  10 Damian Ct, Chester, NY 10918

  Welcome to 10 Damian Court — a stunning custom Colonial set on 2.6 acres of beautifully landscaped grounds in a peaceful Chester cul-de-sac. Built in 2004, this impressive home offers over 4,300 sq ft of elegant living space, featuring 11 bedrooms and 6.5 baths designed for comfort and flexibility. Enjoy a spacious eat-in kitchen with granite counters and pantry, a formal dining area, and a

  Elimelech Kremer MS Realty Group USA, Inc

  10 Damian Ct, Chester, NY 10918
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  $1,700 per month

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

  8 Main St, Chester, NY 10918

  Conveniently located in the Village of Chester, this spacious one-bedroom apartment is close to all amenities and Route 17. It is situated on the 3rd floor and features an open floor plan with exposed brick walls, providing plenty of natural light and windows.

  Jeanmarie Valentin HomeSmart Homes & Estates

  8 Main St, Chester, NY 10918
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  $453,000 Sold May 08, 2025

  16 Academy Ave, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 2,358 Sq Ft
  • Built 1850

  Last Sold Summary

  • 1% Above List Price
  • $192/SF
  • 21 Days On Market

  Current Estimated Value $477,406

  Last Listing Agent Celina Rofer Howard Hanna Rand Realty

  16 Academy 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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