Orange, NY Homes

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  /31

  $1,199,900

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

  16 Lori Ln, Chester, NY 10918

  Indulge in luxury living at this resort-style residence in Chester, NY, within the prestigious Monroe Woodbury School District. Set on a tranquil cul-de-sac, this home graces one of MW Schools' most beautiful streets. Crafted with precision by Paul Janus Building Arts, custom millwork, arched windows, and detailed moldings evoke the charm of Westchester and Bergen County homes. From the

  

  Randolph Rogers

  eXp Realty

  (845) 681-2264

  16 Lori Ln, Chester, NY 10918
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  Explore Chester

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  /30

  $3,000 per month

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

  3404 Whispering Hills Unit 44260, Chester, NY 10918

  This spacious 3-bedroom, 2.5-bathroom townhouse in the heart of Chester, NY, offers the perfect balance of comfort and convenience. Nestled in a commuter-friendly location, this home is ideal for those seeking easy access to major highways, while enjoying a peaceful village setting.Step inside to discover a bright, open floor plan featuring laminate floors throughout the main level and a

  

  Chativa Bowen

  Keller Williams Realty

  (845) 704-4882

  3404 Whispering Hills Unit 44260, Chester, NY 10918
• 

  $367,500 Sold Aug 29, 2025

  • 1,316 Sq Ft
  • $279/SF
  • 25 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1987

  3911 Whispering Hills, Chester, NY 10918

  Whispering Hills – End Unit Condo! Beautifully updated 3 Bedroom, 2 Full Bath unit with 1-Car Attached Garage. Features an updated kitchen with quartz countertops, stainless steel appliances, and hardwood floors in the kitchen, dining area, and primary bedroom. Spacious living room with cathedral ceilings, electric fireplace with blower, and a decorative tiled accent wall. Primary suite includes

  Hershel Lowy Master Realty Group Inc.

  3911 Whispering Hills, Chester, NY 10918
• 

  Est $810,395 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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  /29

  $564,000

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

  391 Bull Mill Rd, Chester, NY 10918

  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 driveway, this home

  

  Alexandra Zinko

  Century 21 Realty Center

  (845) 412-9860

  391 Bull Mill Rd, Chester, NY 10918
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  /20

  $6,900 per month

  • 7 Beds
  • 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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  $350,000 Sold Aug 28, 2025

  • 1,316 Sq Ft
  • $266/SF
  • 23 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1987

  2402 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-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

  Kewin Garabito eXp Realty

  2402 Whispering Hills Dr, Chester, NY 10918
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  Est $225,933 Not Listed For Sale

  495 Laroe Rd, Chester, NY 10918

  495 Laroe Rd, Chester, NY 10918
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  /9

  $49,000 Pending

  • Land
  • 4.00 Acres
  • $12,250 per Acre

  L17 Vanderwalker Rd, Chester, NY 12817

  Nestled in the heart of the Adirondacks, this peaceful 4-acre parcel offers a rare opportunity to own your own private slice of nature. The property features a quiet, wooded setting - ideal for a future homesite or a recreational getaway. A large existing shed structure on-site provides immediate utility for storage or workspace. Conveniently located just minutes from downtown Chestertown, Loon

  

  Zachary Layton

  Four Seasons Sotheby's International Realty

  (518) 608-2854

  L17 Vanderwalker Rd, Chester, NY 12817
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  /12

  $2,800 per month

  • 3 Beds
  • 2.5 Baths
  • 1,632 Sq Ft
  • Townhouse for Rent

  41 Evan Rd, Warwick, NY 10990

  Spacious and sparkling three floor townhouse located in Kings Estates ! This unit has a finished full sized basement, great closet space and sparkling hardwood floors. The back deck off of the dining room and kitchen area offers a great view. Call for your showing today.

  Christina Biagini Weichert Realtors

  41 Evan Rd, Warwick, NY 10990
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  $540,000 Sold Aug 28, 2025

  • 2,040 Sq Ft
  • $265/SF
  • 35 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1991

  1 Winding Trail, Chester, NY 10918

  Welcome to 1 Winding Trail in the Town of Chester. This well-maintained home sits on a picturesque 1.2 acre lot located in the desirable Bull Mill Road area with Monroe-Woodbury Schools. With an easy flow, the home’s first floor boasts a spacious family room with fireplace, an office/den and a half bath. Walk-up a few steps into the large living room and a formal dining room both of which

  Donald Serotta Howard Hanna Rand Realty

  1 Winding Trail, 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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  /13

  $711,000 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 2,092 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 and hot tub. Home offers many recent upgrades which include updated kitchen,

  

  Dulce M Ferrera

  Keller Williams Hudson Valley

  (845) 203-6068

  2 Dawn Ct, Chester, NY 10918
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  /15

  $2,100 per month

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

  25 Ruscitti Dr Unit 2, Chester, NY 10918

  Discover this delightful 1-bedroom, 1-bathroom ranch-style apartment in a quiet corner of Blooming Grove/Chester. As part of a 2-unit residence, this apartment provides a private and serene living experience. The single-level layout is perfect for easy access and comfortable living. A wonderful opportunity to enjoy a peaceful setting while still being conveniently located.

  Abraham Schwartz Priority Management

  25 Ruscitti Dr Unit 2, Chester, NY 10918
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  $600,000 Sold Aug 28, 2025

  • 1,868 Sq Ft
  • $321/SF
  • 23 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1971

  15 Birch Dr, Monroe, NY 10950

  Now Active! This beautifully updated Raised Ranch sits on over 1.6 acres in one of Monroe’s most charming neighborhoods—ready for you to explore today. With four bedrooms and two full baths, this move-in-ready home offers the ideal blend of style, comfort, and convenience. Unwind in your private backyard oasis, take a dip in the in-ground pool or enjoy a peaceful stroll to the lake—complete with

  Rebecca Bank Keller Williams Realty

  15 Birch Dr, Monroe, NY 10950
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  Est $274,575 Not Listed For Sale

  5 Heidi Ln, Chester, NY 10918

  5 Heidi Ln, Chester, NY 10918
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  /2

  $369,000 Coming Soon

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

  4703 Whispering Hills Unit 320, 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. Coming soon. Stay tuned....

  

  Erin Connolly

  Artisan Realty

  (845) 328-6250

  4703 Whispering Hills Unit 320, Chester, NY 10918
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  /32

  $2,600 per month

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

  1220 Whispering Hills, Chester, NY 10918

  Looking for the perfect rental that is pet (small pet) friendly? Well here you go! This 2 bedroom townhome with an attached one car garage is in the Whispering Hills community known for easy commutes to NYC with buses that come right into the complex. Beautifully renovated unit with a contemporary flair of vaulted ceilings, chocolate Pergo floors, light stone fireplace, new lighting, new

  Karen Taphorn Howard Hanna Rand Realty

  1220 Whispering Hills, Chester, NY 10918
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  $460,000 Sold Aug 28, 2025

  • 1,770 Sq Ft
  • $260/SF
  • 40 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1968

  22 Able Noble Dr, Chester, NY 10918

  Welcome to 22 Able Noble Drive, a charming and spacious Raised Ranch nestled in a neighborhood within the highly sought-after Monroe Woodbury School District. Offering 1,770 square feet of living space, this 4-bedroom, 2-bathroom home is the perfect blend of comfort, functionality, and location.Step inside to find a bright and inviting layout, ideal for both everyday living and entertaining

  Robin Kelly Picture It Sold, LLC

  22 Able Noble Dr, Chester, NY 10918
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  Est $94,895 Not Listed For Sale

  30 Mount Ridge Ct, Monroe, NY 10950

  30 Mount Ridge Ct, Monroe, NY 10950
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  /42

  $575,000

  • 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

  $3,400 per month

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • House for Rent

  21 Sackett Square, Chester, NY 10918

  Picture Perfect Beautiful is this charming ranch style house rental available for immediate occupancy. Enjoy one level living, so you can skip the stairs! Newly renovated, fully detached home situated in commuter friendly Chester and in the Monroe-Woodbury school district. Featuring three bedrooms, two full baths and a large level backyard. Master bedroom suite with full bath. The kitchen

  Courtney Tablante Keller Williams Realty

  21 Sackett Square, Chester, NY 10918
• 

  $585,000 Sold Aug 27, 2025

  • 2,516 Sq Ft
  • $233/SF
  • 57 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1992

  7 Cambridge Cir, Monroe, NY 10950

  Move in ready Colonial with ADA Accessable features! Welcome to 7 Cambridge Circle, a perfect blend of colonial home living with access for ALL! This home welcomes you into a large entry foyer with HW floors, flowing into your formal living room to your right and your formal dining to your left. Past the large staircase, is your updated kitchen with new SS appliances and corian countertops. Off

  Alissa Taylor-Vetell Keller Williams Realty

  7 Cambridge Cir, Monroe, NY 10950
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  Est $355,213 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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  /50

  $979,000

  • 4 Beds
  • 3 Baths
  • 2,700 Sq Ft

  893 Laroe Rd, Monroe, NY 10950

  When you walk in the front door, the artful design and carefully curated surroundings immediately banish the outside world. The open floor plan and copious windows bring in the sunshine and natural light. Begin in the spacious living room with woodburning fireplace that opens into the family room. The living room flows naturally to the family room with its own fireplace, and it is surrounded by

  Lisa Fountain Corcoran Country Living

  893 Laroe Rd, Monroe, NY 10950
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  /48

  $2,550 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
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  $610,000 Sold Aug 25, 2025

  • 1,987 Sq Ft
  • $307/SF
  • 39 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1973

  411 Prospect Rd, Chester, NY 10918

  Welcome to this spacious and well-laid-out home offering over 1,900 square feet of comfortable living space. With 4 bedrooms and 2 full bathrooms, there's room for everyone to enjoy. The upper level features two bedrooms and a full bath. One of the bedrooms offers generous space, perfect for a primary bedroom or flexible use. The eat-in kitchen is both functional and inviting—great for cooking,

  Dana Posner Howard Hanna Rand Realty

  411 Prospect Rd, Chester, NY 10918
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  Est $813,383 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
• 

  

  /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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  /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
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  $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

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

  68 Conklingtown Rd, Chester, NY 10918

  68 Conklingtown Rd, Chester, NY 10918
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  /34

  $359,000

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

  2409 Whispering Hills, Chester, NY 10918

  Just Move in and Enjoy! Beautifully maintained, sun filled and open 3 BR, 2 1/2 bath end unit in Whispering Hills! Lovely wood floors on 1 st floor! LR with fireplace opens to Dining area. Updated Kitchen with stainless steel appliances has sliders to private patio! Updated baths! New garage door and opener! A/C replaced about 5 years ago. Water heater replaced about 2 years ago.

  Linda Clark Hudson Valley Griffith

  2409 Whispering Hills, 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
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  $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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  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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  /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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  /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
• 

  $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
• 

  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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