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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  /20

  $6,920 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
• 

  $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 $810,797 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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  /9

  $49,000

  • 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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  /16

  $2,400 per month

  • 2 Beds
  • 1.5 Baths
  • 1,052 Sq Ft
  • Condo for Rent

  4608 Whispering Hills, Chester, NY 10918

  newly renovated 2 Bed. and 2 Baths unit in the desired Whispering Hills development has so much to offer from its beautiful lush grounds to several pools and basketball courts, friendly neighbors, book your showing today!!

  Abraham Kellner MS Realty Group USA, Inc

  4608 Whispering Hills, Chester, NY 10918
• 

  $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
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  Est $216,198 Not Listed For Sale

  495 Laroe Rd, Chester, NY 10918

  495 Laroe Rd, Chester, NY 10918
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  /29

  $564,000 Open Sun 1PM - 4PM

  • 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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  /23

  $3,200 per month

  • 3 Beds
  • 2.5 Baths
  • 1,698 Sq Ft
  • Townhouse for Rent

  196 Eagleton Dr, Monroe, NY 10950

  Welcome to 196 Eagleton Dr, this spacious 3-bedroom, 2.5 full-bathrooms, duplex level end unit Townhouse style. The first floor features Living-room, Kitchen, hardwood cabinets, half bathroom hardwood floors. Sliding glass doors lead you to a patio with privacy fence and overlooking the best view in all of Monroe. The second floor: Primary bedroom with walk-in closet, full bathroom and private

  Kirk German HomeSmart Homes & Estates

  196 Eagleton Dr, Monroe, NY 10950
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  $400,000 Sold Jul 28, 2025

  • 1,435 Sq Ft
  • $279/SF
  • 25 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1900

  7 Garden St, Chester, NY 10918

  A/O CTS! Don't let the size of this home fool you. This perfectly proportioned farmhouse has so much to offer. The three nice sized bedrooms offer enough room for those looking for a starter home or even someone looking to downsize but still have extra space. Nice sized extra room on main level is perfect for a home office, den or even a guest bedroom. Two full sized bathrooms, one on each level

  Harmoni VanEtten eXp Realty

  7 Garden St, Chester, NY 10918
• 

  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
• 

  

  /25

  $759,900 Pending

  • 5 Beds
  • 3.5 Baths
  • 4,490 Sq Ft

  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

  (845) 622-4796

  27 Grand View Terrace, Chester, NY 10918
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  /20

  $2,100 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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  $457,500 Sold Jul 25, 2025

  • 1,842 Sq Ft
  • $248/SF
  • 32 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1970

  12 Mari Rd, Chester, NY 10918

  Welcome to the market a charming 4-Bedroom raised ranch in a peaceful Sugar Loaf neighborhood. Situated in a serene and friendly neighborhood with Warwick schools. This home features four bedrooms and 1.5 baths. Wall-to-wall carpets have been removed to reveal untouched original hardwood floors. The lower level offers a versatile space, ideal for a family room or home office,

  Ryan Degnan Howard Hanna Rand Realty

  12 Mari Rd, Chester, NY 10918
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  Est $286,219 Not Listed For Sale

  5 Heidi Ln, Chester, NY 10918

  5 Heidi Ln, Chester, NY 10918
• 

  

  /28

  $569,900 Pending

  • 4 Beds
  • 2 Baths
  • 1,868 Sq Ft

  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

  (845) 412-9022

  15 Birch Dr, Monroe, NY 10950
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  /33

  $1,700 per month

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

  13 Railroad Ave, Chester, NY 10918

  FANTASTIC and huge 1 bedroom apartment in the heart of the historic Village of Chester. A second floor unit in the historic American House (a former hotel) with lots of windows for great natural light, and hardwood floors throughout. Private entrance which includes large closet for storage -- then up the stairs to the apartment. Tenant responsible for electric & heat(and Internet/cable/phone,

  Dean Diltz Keller Williams Realty

  13 Railroad Ave, Chester, NY 10918
• 

  $525,000 Sold Jul 24, 2025

  • 2,122 Sq Ft
  • $247/SF
  • 43 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1998

  11 Vista Dr, Chester, NY 10918

  Welcome to 11 Vista Drive, a spacious 4-bedroom, 3-bathroom home nestled in one of Chester’s most desirable neighborhoods. With 2,122 square feet of living space, this property offers plenty of room for a growing family to make lasting memories.Situated on a lovely lot with municipal water and sewer, this home provides both convenience and potential. While some updates are needed—such as

  James Feldhaus eXp Realty

  11 Vista Dr, Chester, NY 10918
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  Est $93,362 Not Listed For Sale

  30 Mount Ridge Ct, Monroe, NY 10950

  30 Mount Ridge Ct, Monroe, NY 10950
• 

  

  /29

  $369,000

  • 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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  /16

  $2,500 per month

  • 1 Bed
  • 1 Bath
  • 1,768 Sq Ft
  • House for Rent

  21 Murray Dr, Chester, NY 10918

  Introducing a wonderfully spacious one-bedroom apartment on the bottom floor, which offers an impressive 1768 square feet of living space. This apartment features a generously sized bedroom, plenty of closet space and storage, an updated eat-in kitchen with granite countertops, stainless steel appliances, and a full bath, ensuring comfort and convenience. Laundry facilities are available in the

  Carla Terranova Keller Williams Realty

  21 Murray Dr, Chester, NY 10918
• 

  $869,000 Sold Jul 24, 2025

  • 3,100 Sq Ft
  • $280/SF
  • 85 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2024

  26 W Meadow Way, Chester, NY 10918

  TO BE BUILT-photo depicted is of another Skylark model built by Quality Craftsmen, Valentine Home Builders. THIS IS AN ABSOLUTELY STUNNING 5 ACRE LOT...SPECTACULAR VIEW. The Skylark Model CAN BE CUSTOM BUILT WITH DELIVERY BY SPRING. This brand new fabulous Colonial includes many comfortable features finished by quality guaranteed, Valentine Home Builders. This model offers an efficient home plan

  Nancy Sardo BHG Real Estate Green Team

  26 W Meadow Way, Chester, NY 10918
• 

  Est $361,750 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
• 

  

  /50

  $995,000

  • 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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  /46

  $3,800 per month

  • 4 Beds
  • 2.5 Baths
  • 2,166 Sq Ft
  • House for Rent

  14 Lori Ln, Chester, NY 10918

  THE RENTAL YOU HAVE BEEN LOOKING FOR! Beautiful, well-kept fabulous home in beautiful neighborhood Monroe Woodbury School district. Gorges kitchen with appliances, spacious rooms, ample living space, and expansive backyard to enjoy all year round, Great location! Close to many major shopping areas and highways. This lovely home has all your needs. Call today, before it’s gone!

  Michael Pollak Master Realty Group Inc.

  14 Lori Ln, Chester, NY 10918
• 

  $735,000 Sold Jul 21, 2025

  • 2,980 Sq Ft
  • $247/SF
  • 19 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2004

  189 Creamery Pond Rd, Chester, NY 10918

  MOVE right into this Exquisite CUSTOM COLONIAL with many upgrades and extras in the perfect commuter friendly, prestigious development, " Creamery Pond Estates " which is located in the charming hamlet of Sugar Loaf with all the unique shops where handcrafted, one of a kind gifts can be purchased ,boutiques, incredible restaurants, breweries, wineries, skiing, hiking , apple orchards, farmers

  Patricia Brady Keller Williams Realty

  189 Creamery Pond Rd, Chester, NY 10918
• 

  Est $804,330 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
• 

  

  /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

  $1,600 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
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  $310,000 Sold Jul 21, 2025

  • 1,086 Sq Ft
  • $285/SF
  • 18 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1987

  4706 Whispering Hills, Chester, NY 10918

  ACCEPTED OFFER!- INSPECTION COMPLETED- CONTRACTS EXECUTED**Welcome to Whispering Hills – Where Comfort Meets Convenience!**Discover your dream home in this charming community, featuring 2 spacious bedrooms and 1.5 well-appointed bathrooms, complemented by a generous 2-car garage. The master suite is a true retreat, boasting a large walk-in closet and soaring cathedral ceilings that create

  Jessica Evans Keller Williams Hudson Valley

  4706 Whispering Hills, 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
• 

  

  /50

  $849,900

  • 5 Beds
  • 3 Baths
  • 3,485 Sq Ft

  284 Bull Mill Rd, Chester, NY 10918

  Monroe's Stunning Mini Mansion Awaits Its New Owner!This exquisite home offers everything you've been dreaming of in an ideal location. Step into this 5-bedroom, 3-bath residence featuring a beautiful double-height entrance and a striking palladium window, welcoming you with its elegant double-sided luxury staircase.Before heading upstairs, prepare to be impressed by the spacious chef's

  Jayne Mangieri Keller Williams Valley Realty

  284 Bull Mill Rd, Chester, NY 10918
• 

  

  /19

  $750 per month

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

  7915 State Route 9 Unit 2, Chester, NY 12860

  Basic 1BR/1BA apartment Pottersville! This unit has a large porch and semi-private yard. Exceptionally easy to access from I-87, close to skiing, 20 minutes to Gore, 25 minutes to Lake George. Heat, hot water, sewer and water included in rent. Landlord plows parking lot, tenant is responsible for their walkway. SF estimated. No smoking, no pets. 3x income and renter's insurance required. This

  Jonathan Van Dyk Equitas Realty

  7915 State Route 9 Unit 2, Chester, NY 12860
• 

  $665,000 Sold Jul 15, 2025

  • 2,608 Sq Ft
  • $255/SF
  • 27 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2004

  174 Creamery Pond Rd, Chester, NY 10918

  Welcome to this beautifully maintained 4 bedroom, 2.5 bath Colonial nestled in the historic craft village of Sugar Loaf and award winning Warwick Valley Schools. This classic home offers timeless curb appeal, a spacious layout perfect for entertaining. The great room features an elegant stone fireplace, perfect for cozy evenings. A flowing layout with separate living, dining and great rooms

  Michele Tobin Keller Williams Realty

  174 Creamery Pond Rd, Chester, NY 10918
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 3,182 Sq Ft

  63 Main St, Chester, NY 10918

  63 Main St, Chester, NY 10918
• 

  

  /37

  $675,000 Open Sat 11AM - 1PM

  • 5 Beds
  • 3 Baths
  • 2,983 Sq Ft

  9 Mount Ridge Ct, Monroe, NY 10950

  Tucked away on a peaceful cul-de-sac, this lovingly maintained 5-bedroom, 3-full-bath home offers 3,000 square feet of light-filled living space and a layout designed for comfort and flexibility. Owned by the original homeowner since day one, this property has been thoughtfully cared for and is ready for its next chapter.Inside, you’ll find big, bright rooms and an easy flow perfect for

  James Feldhaus eXp Realty

  9 Mount Ridge Ct, Monroe, NY 10950
• 

  

  /15

  $2,700 per month

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Apartment for Rent

  62 Main St, Chester, NY 10918

  Tons of square footage in a quiet area with amazing views. With coffe shops , entertainment and restaurants within walking distance , this rental will go quick! Ample parking, a backyard complete with play area, bamboo floors and 5 minutes from commuting highways make this place a unicorn in the real estate world. Come check it out!

  Ryan Case Keller Williams Realty

  62 Main St, Chester, NY 10918
• 

  $265,000 Sold Jul 11, 2025

  • Land
  • 6 Acres
  • $42,063 per Acre

  • 152 Days On Market

  10 El Dorado Trail, Chester, NY 10918

  Amazing opportunity to own this 6.3 Acre Lot in Monroe School District, Drilled Well and Electric on site, drilled well in place, Level lot with panoramic views surrounded by exclusive homes. Come build your dream home only 60 Miles to NYC/Minutes to RT17/17M/I87

  Lisandra Rivera Keller Williams Realty

  10 El Dorado Trail, 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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