Chester, NY Homes

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  /40

  $769,000

  • 4 Beds
  • 2.5 Baths
  • 3,063 Sq Ft

  48 Brennan Ct, Chester, NY 10918

  Welcome to this stunning home nestled on 5 acres near the heart of Chester, NY. Tucked away for ultimate privacy, yet just minutes from shopping, dining, and major highways-it's the perfect blend of seclusion and convenience. Step inside this spacious 4-bedroom 3-bathroom retreat, designed for comfort and style. This open layout flows seamlessly with plenty of natural light pouring in through

  Claude Brischoux Keller Williams Realty

  48 Brennan Ct, Chester, NY 10918
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  /48

  $2,400 per month

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

  4706 Whispering Hills, Chester, NY 10918

  Welcome to this beautifully updated residence in the desirable Whispering Hills community, where comfort and convenience come together in a thoughtfully designed home. Featuring 2 bedrooms and 1.5 baths, this property offers a warm and inviting fireplace, an in-unit washer and dryer, generous storage space, and the rare advantage of a private two-car garage. The updates throughout the home

  Nael Dassan Century 21 Elite Realty

  4706 Whispering Hills, Chester, NY 10918
• 

  $305,000 Sold Aug 22, 2025

  • 1,084 Sq Ft
  • $281/SF
  • 27 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1987

  4501 Whispering Hills Dr, Chester, NY 10918

  Effortless Living with Exceptional AmenitiesWelcome to this beautifully refreshed 2-bedroom, 1-bathroom condo where comfort meets convenience in a vibrant, amenity-rich community. Thoughtfully updated and truly move-in ready, this home is the perfect choice for those who want style, function, and low-maintenance living.Step inside to find freshly painted interiors and brand new carpeting

  Bernadette Giordano Howard Hanna Rand Realty

  4501 Whispering Hills Dr, Chester, NY 10918
• 

  Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,600 Sq Ft

  21 Hardscrabble Rd, Chester, NY 10918

  21 Hardscrabble Rd, Chester, NY 10918
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  /35

  $690,000

  • 3 Beds
  • 3 Baths
  • 3,200 Sq Ft

  23 Renies Rd, Chester, NY 10918

  Escape to your own sanctuary in this stunning 3 bedroom 3 full bath contemporary cedar home, perfectly blending modern comfort with natural charm. Inside you'll find an open-concept layout with soaring ceilings, large windows, and natural wood finishes that create a warm, modern vibe. The spacious kitchen features stainless appliances, hickory cabinets and an island ideal for entertaining. Two

  Kristie Jacques Century 21 Full Service Realty

  23 Renies Rd, Chester, NY 10918
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  /22

  $2,550 per month

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

  4612 Whispering Hills, Chester, NY 10918

  Welcome to 4612 Whispering Hills — a spacious, move-in-ready 2-bedroom townhome nestled in the highly sought-after Whispering Hills complex. This home offers the perfect blend of comfort, privacy, and convenience, just minutes from major highways, commuter buses, shopping centers, and more.Step inside through your private entrance and enjoy serene nature views right from your doorstep. The main

  Alissa Taylor-Vetell Keller Williams Realty

  4612 Whispering Hills, Chester, NY 10918
• 

  $459,000 Sold Aug 19, 2025

  • 1,872 Sq Ft
  • $245/SF
  • 25 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1968

  15 Vivian Ln, Chester, NY 10918

  Desirable Family Neighborhood! This 4BR, 2BA Colonial Home is in sought-after Surrey Meadows. It's a great place to start or for a family looking for more space and bedrooms. The main floor has an open floor plan living/dining room. Updated kitchen with newer stainless steel appliances. First-floor laundry room. Both bathrooms are updated as well. The second floor has a master bedroom plus three

  Joseph Giglio Keller Williams Realty

  15 Vivian Ln, Chester, NY 10918
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  Est $334,955 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 913 Sq Ft

  58 Oxford Springs Rd, Chester, NY 10918

  58 Oxford Springs Rd, Chester, NY 10918
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  /43

  $689,000 Open Sun 11AM - 1PM

  • 4 Beds
  • 2.5 Baths
  • 2,548 Sq Ft

  165 Creamery Pond Rd, Chester, NY 10918

  The timeless, elegant Colonial in the Warwick School District is ready for a new hallmark. Situated just behind the Sugarloaf Arts Village—home to over 50 vibrant small shops, restaurants, and unique places to explore—this residence offers both charm and convenience. Spacious and filled with natural light, it’s perfect for peaceful enjoyment with your loved ones. A gas fireplace adds warmth and

  Kichka Pascaru Christie's Int. Real Estate

  165 Creamery Pond Rd, Chester, NY 10918
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  /6

  $1,500 per month

  • 1 Bed
  • 1 Bath
  • 1,316 Sq Ft
  • Condo for Rent

  3102 Whispering Hills Unit 678, Chester, NY 10918

  CURRENT TENANTE IS SEEKING A ROOMMATE. Looking to rent a fully furnished 1 bedroom with a private bathroom and share the living and kitchen space in a fully air conditioned unit. This would be a month-to-month tenancy and owner is very flexible. Assigned parking spot is available with access to the swimming pool, common area and gym. Located in Chester, NY which is accessible to major

  Stephanie Landeck BHG Real Estate Green Team

  3102 Whispering Hills Unit 678, Chester, NY 10918
• 

  $560,000 Sold Aug 19, 2025

  • 2,240 Sq Ft
  • $250/SF
  • 37 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1993

  21 Jeffrey Dr, Chester, NY 10918

  Cozy Four-Bedroom Home with Mountain ViewsThis lovely Colonial-style home sits at the end of a quiet street in Sugar Loaf Heights. Enjoy peaceful surroundings and beautiful mountain views every day.Inside, the home has a large and open layout that makes daily living easy and comfortable. The bright kitchen has sliding glass doors that lead to the back deck—perfect for sipping coffee and

  Kevin Tuhy Keller Williams Realty

  21 Jeffrey Dr, Chester, NY 10918
• 

  Est $582,227 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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  /8

  $899,900

  • 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
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  /37

  $5,500 per month

  • 6 Beds
  • 3 Baths
  • 3,066 Sq Ft
  • House for Rent

  3 Grand View Terrace, Chester, NY 10918

  Discover refined living at 3 Grand View Terrace, a beautiful 6-bedroom, 3-bath Colonial in Chester's sought-after Valley View Phase II subdivision. This impressive home boasts 3,066 sq ft of living space, with a full walkout basement and an attached 2-car garage. Built in 2003, it features central air and forced air heat. Relax by the fireplace or enjoy the outdoor space on the 0.55-acre lot.

  Shalom Landau eRealty Advisors, Inc

  3 Grand View Terrace, Chester, NY 10918
• 

  $780,000 Sold Aug 15, 2025

  • 4,490 Sq Ft
  • $174/SF
  • 43 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 2004

  27 Grand View Terrace, Chester, NY 10918

  Spectacular colonial located on the highly desired executive subdivision, Valley View Phase II. The grand double door entryway is just a hint of what awaits inside this almost 5,000 square foot Colonel home. This home sits up high with fantastic mountain views and sunsets, it has 5 bedrooms, 3 full baths all with double high ceilings and hardwood floors. Super large master with two walk in

  Randolph Rogers eXp Realty

  27 Grand View Terrace, Chester, NY 10918
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  Est $657,604 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,744 Sq Ft

  5 Marion St, Chester, NY 10918

  5 Marion St, Chester, NY 10918
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  /50

  $879,000

  • 4 Beds
  • 4 Baths
  • 4,489 Sq Ft

  11 Saddle Hill Rd, Chester, NY 10918

  **Welcome to 11 Saddle Hill Road – A Perfect Blend of Luxury, Space & Location**This stunning brick Colonial offers the perfect balance of private luxury and everyday convenience. With over **5,000 square feet** of impeccably finished living space, this home provides ample room for everyone to **live, work, and relax in comfort**.Step into the **grand two-story foyer**, flooded with

  Alissa Taylor-Vetell Keller Williams Realty

  11 Saddle Hill Rd, Chester, NY 10918
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  /28

  $2,300 per month

  • 2 Beds
  • 1.5 Baths
  • 1,150 Sq Ft
  • Condo for Rent

  2117 Whispering Hills, Chester, NY 10918

  JUST LISTED * 2 Bedroom Townhome Rental in Whispering Hills * 2 level unit with a 1 Car garage Beautiful Townhome * No Carpets at all - Pergo floos * Spacious & Bright Master Bedroom has Huge Walk in closet * Laundry on main level * Central Air * NYC bus comes in development, Sidewalks too, near Shoprite, CVS, McDonalds ,Mobil & all Highways to NYC * Great location for West Point or NYC Commuter

  Rosalie Cook Weichert Realtors

  2117 Whispering Hills, Chester, NY 10918
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  $330,000 Sold Aug 15, 2025

  • 1,331 Sq Ft
  • $248/SF
  • 142 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1987

  4503 Whispering Hills, Chester, NY 10918

  WELCOME TO WHISPERING HILLS CONDOMINIMUM COMMUNITY!!! Check out this 3 Bedroom, 2.5 Bathroom Condominium nestled in the Village of Chester and in the Chester School District. This Condo is located a mile from the Village of Chester featuring a variety of Village amenities including local restaurants, shopping centers, medical offices, banking services, home improvement stores, close to

  Richard Baxter Keller Williams Realty

  4503 Whispering Hills, Chester, NY 10918
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  Est $492,550 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,956 Sq Ft

  26 Maple Ln, Monroe, NY 10950

  26 Maple Ln, Monroe, NY 10950
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  /45

  $674,999

  • 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

  Alison Orlando Keller Williams Hudson Valley

  507 Bull Mill Rd, Chester, NY 10918
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  /20

  $1,900 per month

  • 2 Beds
  • 1 Bath
  • 1,258 Sq Ft
  • Apartment for Rent

  15 Railroad Ave Unit 2, Chester, NY 10918

  FANTASTIC and huge 2 bedroom apartment in the heart of the historic Village of Chester. A third floor unit in the historic American House (a former hotel) -- and with either first or second floor access -- with lots of windows for great natural light, and hardwood floors throughout. CENTRAL AIR! Approx. 1,258 square feet, along with a HUGE walk-up attic. There's a small third room which can be an

  Dean Diltz Keller Williams Realty

  15 Railroad Ave Unit 2, Chester, NY 10918
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  $323,500 Sold Aug 11, 2025

  • 1,360 Sq Ft
  • $238/SF
  • 35 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1950

  98 High St, Chester, NY 10918

  First time on the market! Welcome to 98 High Street, Chester – a well-loved, original-owner home full of potential. This 4-bedroom, 1.5-bath property offers a spacious layout and solid bones, ready for your personal touch. Step in through the mudroom into an open-concept kitchen and living area, perfect for gathering and entertaining. Down the hall, you’ll find the primary bedroom, a full bath,

  Zachary Foley eXp Realty

  98 High St, Chester, NY 10918
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  Est $446,507 Not Listed For Sale

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

  13 Maple Ln, Monroe, NY 10950

  13 Maple Ln, Monroe, NY 10950
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  /8

  $799,999

  • 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.).

  Karen Gauvin Our House Real Estate Group

  34 Mountainside Dr, Chester, NY 10918
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  /14

  $1,500 per month

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

  26 Main St Unit C, Chester, NY 10918

  Live in the heart of historic Chester! This beautiful third floor 1-bedroom, 1-bath apartment is located right on Main Street. Featuring tons of natural light and a private back deck it's the perfect retreat in a vibrant village setting. You'll be steps away from coffee shops, restaurants, and the Heritage Trail, making it easy to enjoy everything Chester has to offer. Commuters will love the

  Brooke Lorimer Keller Williams Realty

  26 Main St Unit C, Chester, NY 10918
• 

  $536,000 Sold Aug 06, 2025

  • 1,716 Sq Ft
  • $312/SF
  • 62 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1972

  16 Ayr Rd, Chester, NY 10918

  3/31/25 Multiple offers received. Please submit your highest and best by Wednesday, April 2, at 5:00. Include in your offer how any potential appraisal gap will be handled. Thank you for your interest in this home.This beautifully situated ranch style home offers amazing views, privacy, and convenience. The kitchen window displays a huge backyard with beautiful greenery in the spring and

  Luanne McGann Century 21 Full Service Realty

  16 Ayr Rd, Chester, NY 10918
• 

  Est $508,517 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,104 Sq Ft

  7 Maple Ln, Monroe, NY 10950

  7 Maple Ln, Monroe, NY 10950
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  /50

  $975,000 Open Sun 3:30PM - 6PM

  • 4 Beds
  • 3 Baths
  • 2,370 Sq Ft

  2 Primrose Ln, Chester, NY 10918

  Introducing an exceptional opportunity to own your dream property with over 18 acres wooded land! This stunning colonial is a perfect blend of luxury and functionality. Spanning 2370 square footage plus finished basement with 4 spacious bedrooms and 3 elegantly designed bathrooms, this home boasts an inviting atmosphere that caters to both relaxation and entertaining.As you step inside,

  Joel Friedman MS Realty Group USA, Inc

  2 Primrose Ln, Chester, NY 10918
• 

  $345,000 Sold Aug 05, 2025

  • 1,698 Sq Ft
  • $203/SF
  • 37 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1998

  326 Heritage Ln, Monroe, NY 10950

  Great starter or downsizer! 3 bedroom 2.5 bath End Unit Townhouse in sought after Windridge! Main living area offers spacious living room with wood burning fireplace & sliding doors to rear patio,1/2 bath, Large kitchen with plenty of counter, cabinet space & eat in area. Upper living are has a huge primary bedroom with balcony overlooking rear yard, primary bath & walk-in closet. 2 additional

  Ernie Acampora River Realty Services, Inc.

  326 Heritage Ln, Monroe, NY 10950
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  Est $424,046 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,686 Sq Ft

  31 Maple Ln, Monroe, NY 10950

  31 Maple Ln, Monroe, NY 10950
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  /37

  $724,000 Open Sun 12PM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 3,977 Sq Ft

  278 Gibson Hill Rd, Chester, NY 10918

  AMAZING PROPERTY -- offers something for everyone! Gorgeously restored 3,977 square foot colonial farmhouse on 5.1 private acres, and with a pool, 5 bay carport, a 38x40 garage (with it's own entrance from road -- can rent out for income), and so much more! . . . Located in the Warwick Valley School District (and just a half mile to the Warwick town line). Just minutes to all downtown Warwick has

  Dean Diltz Keller Williams Realty

  278 Gibson Hill Rd, Chester, NY 10918
• 

  $465,000 Sold Aug 04, 2025

  • 1,900 Sq Ft
  • $245/SF
  • 239 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1970

  559 Laroe Rd, Chester, NY 10918

  Welcome to this stunning home located in the heart of Chester NY. Completely renovated, Spacious bedrooms, full baths, plenty of closets, Living/Dining room, Office room, bright kitchen, granite countertops, dishwasher oven and refrigerator, Situated on a relaxing property, while enjoying the peaceful views throughout, in addition to benefiting from a healthy living environment, Close to major

  Eliezer Safdie Sage Realty Center LLC

  559 Laroe Rd, Chester, NY 10918
• 

  Est $397,577 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,365 Sq Ft

  43 Maple Ln, Monroe, NY 10950

  43 Maple Ln, Monroe, NY 10950
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  /49

  $649,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,402 Sq Ft

  9 June Rd, Chester, NY 10918

  Welcome to 9 June Road, a rare gem offering 3,122 square feet of well-designed living space in the heart of the Village of Chester.From the moment you arrive, the curb appeal draws you in with a classic rocking chair front porch and custom pavers lining the driveway and walkways. Step into a grand open foyer with a formal living room to the right and an elegant dining room to the left,

  Jason Madison eXp Realty

  9 June Rd, Chester, NY 10918
• 

  $380,000 Sold Jul 30, 2025

  • 1,331 Sq Ft
  • $285/SF
  • 28 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1987

  3816 Whispering Hills, Chester, NY 10918

  WHISPERING HILLS!! END UNIT! MINT! MINT! Mint Condition! Move right in with Nothing to Do! Two Level Living! 3 Bedrooms! 2 1/2 Bathrooms! 2 Car Garage! Updated Kitchen with Break Fast Nook, Stainless Steel Appliances, Custom Tile Back Splash with Sliders to Patio! Master Bedroom Suite With Walk in Closet! Updated Bathrooms! Living Room with New Fireplace! Dining Room! Newer Windows! New Garage

  Amanda Dnistrian ARC Realty 1 in Sales

  3816 Whispering Hills, Chester, NY 10918
• 

  Est $405,090 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,452 Sq Ft

  68 Evan Rd, Warwick, NY 10990

  68 Evan Rd, Warwick, NY 10990
• 

  

  /11

  $34,000

  • Land
  • 1.8 Acres
  • $18,889 per Acre

  L27 Carriage Knolls Rd, Chester, NY 12817

  Seller financing now available! This property has been cleared and excavated in preparation for a new home. Site-plans are complete, perc tests are complete, septic plans have been completed, and an electric pedestal has been installed. (The small shed on-site is included as part of this transaction. Larger building also available separately and would need to be removed once the house certificate

  Walter Swartz Gallo Realty ADK Inc

  L27 Carriage Knolls Rd, Chester, NY 12817
• 

  $350,000 Sold Jul 28, 2025

  • 1,331 Sq Ft
  • $263/SF
  • 23 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1984

  2816 Whispering Hills, Chester, NY 10918

  Welcome to this spacious and beautifully maintained end-unit townhouse offering 3 bedrooms, 2.5 bathrooms, and an oversized two-car garage. The main level features a generous living room with a cozy fireplace, a dining area, and a well-appointed kitchen with a sliding glass door that opens to a private patio—ideal for outdoor entertaining. A convenient half bathroom completes the first

  Bernadette Giordano Howard Hanna Rand Realty

  2816 Whispering Hills, Chester, NY 10918
• 

  Est $354,520 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,276 Sq Ft

  25 Darin Rd, Warwick, NY 10990

  25 Darin Rd, Warwick, NY 10990

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