Chester, NY Homes

• 

  $900,000 Sold Mar 20, 2025

  • 4,644 Sq Ft
  • $194/SF
  • 132 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2000

  221 Oxford Rd, Chester, NY 10918

  Welcome to this immaculate, custom built colonial within the Monroe Woodbury School District. This stunning home boasts 4 bedrooms, 3.5 bathrooms, and an impressive 4,600+ square feet of living space. Step inside and be greeted by the welcoming 2 story entry with gleaming hardwood floors and custom mouldings throughout. Spacious open floor plan with oversized kitchen with breakfast area, living

  Donna Brunell RE/MAX Benchmark Realty Group

  221 Oxford Rd, Chester, NY 10918
• 

  Est $577,118 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,944 Sq Ft

  2 Tyler Place, Monroe, NY 10950

  2 Tyler Place, Monroe, NY 10950
• 

  

  

  /22

  $400,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft

  68 Southside Dr, Monroe, NY 10950

  Located in a prime Monroe, NY location with Monroe-Woodbury Schools, this wonderful home is surrounded by level, well groomed property and offers the perfect blend of classic charm and modern convenience with generous sized rooms throughout. A FIRST FLOOR BEDROOM & FULL BATH is ideal for flexible living arrangements. Step into the bright and airy living room, where natural light pours in and

  Carol Buchanan BHG Real Estate Green Team

  68 Southside Dr, Monroe, NY 10950
• 

  $420,000 Sold Mar 14, 2025

  • 1,371 Sq Ft
  • $306/SF
  • 52 Days On Market

  • Built 1900

  18 Academy Ave, Chester, NY 10918

  Welcome to 18 Academy Ave., a rare gem in the heart of the village, offered for sale for the first time in over 40 years. Built in 1900, this historic two-family home exudes character and charm, offering a unique opportunity for both homeowners and investors.The upstairs unit features a thoughtfully renovated open kitchen with stunning quartz countertops and a cozy fireplace that

  Jason Dillon eXp Realty

  18 Academy Ave, Chester, NY 10918
• 

  Est $492,260 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,780 Sq Ft

  25 Surrey Rd, Chester, NY 10918

  25 Surrey Rd, Chester, NY 10918
• 

  

  /42

  $374,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,698 Sq Ft

  226 Eagleton Dr, Monroe, NY 10950

  FIRST TIME ON MARKET. Original Owner Lovingly Maintained this 3 Bedroom, 2 1/2 Bath Townhouse. PRIME LOCATION - This End Unit is located on a Sought After Cul de Sac. There is adjacent lawn area on which Owner hosted many a good Gathering of Family and Friends. Eat in Kitchen with All Appliances. Spacious Living Room with Sliding Glass Door to Patio backing up to woods for some Privacy.

  Lorrainne Pisciotta Weichert Realtors

  226 Eagleton Dr, Monroe, NY 10950
• 

  

  /51

  $810,000 Sold Mar 11, 2025

  • 5,000 Sq Ft
  • $162/SF
  • 25 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 2006

  16 Heritage Ln, Chester, NY 12817

  Nestled in the heart of the Adirondack Mountains, 16 Heritage Lane is a hidden gem offering tranquility, comfort, and rustic elegance. This stunning property includes vaulted ceilings, 3 fireplaces, 5 bedrooms, 3 of which have en suite bathrooms, gourmet kitchen, and large living spaces. There is a finished basement with a walkout to a private patio one of the many outdoor relaxation spaces.

  Catherine Delf KW Platform

  16 Heritage Ln, Chester, NY 12817
• 

  Est $738,091 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,006 Sq Ft

  69 Dug Rd, Chester, NY 10918

  69 Dug Rd, Chester, NY 10918
• 

  

  /50

  $600,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,144 Sq Ft

  18 Grant Dr, Monroe, NY 10950

  This bi-level home offers both charm and abundant sunshine, meticulously maintained by its original owners, showcasing obvious pride of ownership. The living and dining combination exudes luxury with its gleaming hardwood floors, while the kitchen is efficiently designed with a granite countertop, stainless steel appliances, a pantry, and a tiled backsplash. The three bedrooms on the first floor

  Donna Gennaro Howard Hanna Rand Realty

  18 Grant Dr, Monroe, NY 10950
• 

  

  /33

  $255,000 Sold Mar 03, 2025

  • 876 Sq Ft
  • $291/SF
  • 68 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1961

  78 Panther Mtn Rd, Chester, NY 12817

  Welcome to Grandma's house! Hilltop 1961 ranch with sprawling front lawn that's been in the same family since it was built (and for good reason)! 2/3bd & 1 bath w/ full basement. Two parcels total with detached garage & carport. Horseshoe driveway. Hardwood floors, generac generator, great natural sunlight & convenient location within walking distance to town!

  Angie Mead Gallo Realty ADK Inc

  78 Panther Mtn Rd, Chester, NY 12817
• 

  Est $700,990 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,708 Sq Ft

  16 Twin Brooks Dr, Chester, NY 10918

  16 Twin Brooks Dr, Chester, NY 10918
• 

  

  /42

  $899,000 Pending

  • 5 Beds
  • 4 Baths
  • 4,496 Sq Ft

  10 Spectrum Dr, Chester, NY 10918

  Serene Country Retreat in an Upscale Chester Neighborhood!Set on over 5 peaceful acres with sweeping mountain views, this stunning contemporary home offers the perfect mix of style, comfort, and privacy. With 4 bedrooms and 4 bathrooms, the layout is ideal for both everyday living and effortless entertaining.The sun-drenched living room is a true showpiece—featuring dramatic cathedral

  David Hopstein eRealty Advisors, Inc

  10 Spectrum Dr, Chester, NY 10918
• 

  $565,000 Sold Feb 27, 2025

  • 1,810 Sq Ft
  • $312/SF
  • 11 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1973

  9 Laroc Rd, Chester, NY 10918

  FULLY RENOVATED ~ MODERN HOME WITH LOTS OF UPGRADES!!Prepare to be enchanted by this magnificent Laroc property! No luxury has been spared in this fully renovated, modern bi-level-style residence, boasting over 1800 sqft of pure opulence. As you step through the grand foyer, you are welcomed into a lavish dining room with vaulted ceilings, light tiled floors, and a charming fireplace,

  Nathen Singer MK Realty Inc

  9 Laroc Rd, Chester, NY 10918
• 

  /2

  Est $486,491 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,650 Sq Ft

  2 Stevens Place, Chester, NY 10918

  2 Stevens Place, Chester, NY 10918
• 

  

  /31

  $544,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,844 Sq Ft

  13 Tulip Ln Unit 4, Monroe, NY 10950

  Welcome to this beautifully maintained 3-bedroom, 2-bathroom home nestled in the heart of Monroe, NY. Monroe Woodbury Schools. Low taxes! This inviting property offers an ideal blend of comfort, functionality, and outdoor enjoyment. Step inside to discover a sun-filled living room, formal dining room, and an eat-in kitchen complete with granite countertops, stainless steel appliances, and sliding

  Courtney Tablante Keller Williams Realty

  13 Tulip Ln Unit 4, Monroe, NY 10950
• 

  $305,000 Sold Feb 24, 2025

  • 1,276 Sq Ft
  • $239/SF
  • 28 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1987

  27 Darin Rd, Warwick, NY 10990

  Welcome to 27 Darin Rd. Located in King Estates in Warwick, NY. Step inside and be greeted by cathedral ceilings that create an airy open spacious atmosphere while Sunkissed skylights bathe the interior with natural light. This 2 bedroom,3 Bath townhome has vaulted ceilings, wood-burning fireplace, skylights, a loft perfect for home office space and full partially finished walkout basement. The

  Lauren Donati Homes By Yara Realty Group LLC

  27 Darin Rd, Warwick, NY 10990
• 

  Est $514,402 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,882 Sq Ft

  4 Stevens Place, Chester, NY 10918

  4 Stevens Place, Chester, NY 10918
• 

  

  /36

  $1,199,900 Pending

  • 4 Beds
  • 5 Baths
  • 3,000 Sq Ft

  42 Greycourt Rd, Chester, NY 10918

  Welcome to this stunning brand new estate, nestled on a sprawling over 2.5 acre property! This magnificent residence boasts around 3,000 square feet + extra 2,600 unfinished SQ FT of luxurious living space, perfect for entertaining and relaxation. Features include: 4 spacious bedrooms, each a serene retreat with ample closet space. 5 elegant bathrooms, showcasing premium fixtures and finishes.

  Mendel Muller Master Realty Group Inc.

  42 Greycourt Rd, Chester, NY 10918
• 

  $581,000 Sold Feb 19, 2025

  • 2,067 Sq Ft
  • $281/SF
  • 154 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1947

  204 Farmingdale Rd, Chester, NY 10918

  Situated on the south end of Tomahawk Lake, this home is less than 1.5 hours to Manhattan and has private lake frontage and direct access to launch your kayak. This 2 bedroom, 2 full bathroom home and lake property is the quintessential weekend home. It is quiet and private. Enjoy the spectacular lake views from inside the home! The interior space has an open-concept and vaulted ceilings, a

  Andrew Centrone Keller Williams Hudson Valley

  204 Farmingdale Rd, Chester, NY 10918
• 

  Est $586,890 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,980 Sq Ft

  38 Ayr Rd, Chester, NY 10918

  38 Ayr Rd, Chester, NY 10918
• 

  

  /23

  $499,000 Pending

  • 5 Beds
  • 4 Baths

  70 Main St, Chester, NY 10918

  Discover the perfect blend of versatility and charm with this exceptional property featuring two beautifully maintained units. The main house offers three levels of comfortable living, including four bedrooms, three baths, and a spacious kitchen ideal for gathering and entertaining. The thoughtfully renovated barn boasts a cozy one-bedroom, one-bath layout with modern touches that make it an

  Kassandra Mott Keller Williams Hudson Valley

  70 Main St, Chester, NY 10918
• 

  $475,000 Sold Feb 18, 2025

  • 1,692 Sq Ft
  • $281/SF
  • 50 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1968

  14 Twin Brooks Dr, Chester, NY 10918

  Gorgeous setting! One owner since the beginning! Well cared-for in a wonderful location. This peaceful and serine home has been lived-in, loved and maintained by the same family since the year it was built. The house is solid and well-built with a traditional, modest colonial floor plan. Beautiful hardwood floors throughout, fireplace, large windows, spacious rooms and more. 4 bedrooms and one

  Layla Rose Boyles Century 21 Realty Center

  14 Twin Brooks Dr, Chester, NY 10918
• 

  Est $653,196 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,784 Sq Ft

  46 Ayr Rd, Chester, NY 10918

  46 Ayr Rd, Chester, NY 10918
• 

  

  /20

  $525,000 Pending

  • 4 Beds
  • 1.5 Baths
  • 1,792 Sq Ft

  32 Poplar Dr, Monroe, NY 10950

  GREAT house! If you are looking for move in ready this is IT!!! New kitchen and baths! Either new floors or redone hardwood. Freshly painted. Beautiful paver walkway! New Boiler 2023, Water Heater 2023, Ductless 2022, Roof 10 years old.

  Ann Marie Hahr Keller Williams Realty

  32 Poplar Dr, Monroe, NY 10950
• 

  $369,900 Sold Feb 18, 2025

  • 1,331 Sq Ft
  • $278/SF
  • 48 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1984

  1003 Whispering Hills, Chester, NY 10918

  Welcome to this beautiful corner unit townhome located in the highly sought-after Whispering Hills community in Chester, NY. Nestled in the serene neighborhood this beautifully maintained home offers the perfect blend of comfort convenience & community living. Enjoy the suburban charm of Chester with easy access to major highways making it perfect for commuters. Enjoy a host of amenities inc.

  Tristen Sierra Coldwell Banker Realty

  1003 Whispering Hills, Chester, NY 10918
• 

  Est $745,285 Not Listed For Sale

  • 6 Beds
  • 4.5 Baths
  • 2,646 Sq Ft

  4 Ayr Rd, Chester, NY 10918

  4 Ayr Rd, Chester, NY 10918
• 

  

  /20

  $599,000 Pending

  • 3 Beds
  • 1.5 Baths

  4 Greycourt Rd, Chester, NY 10918

  Magnificent sprawling ranch situated on a park like setting with 2.80 acres with mature landscaping. This home features a spacious 2014 renovated EIK for entertaining with soft close cabinets, granite countertops, stainless steel appliances and an island cook top. Kitchen leads to an open concept large living /dining room combo with a large bay window for natural light with newly refinished

  Scott Loyer Coldwell Banker American Homes

  4 Greycourt Rd, Chester, NY 10918
• 

  $1,247,500 Sold Feb 14, 2025

  • 5,127 Sq Ft
  • $243/SF
  • 304 Days On Market

  • 6 Beds
  • 4.5 Baths
  • Built 1794

  6 Silvertail Rd, Chester, NY 10918

  Turn-Key Home.... completely updated yet incomparable to any new construction. Current owners took this beauty and did everything that brings it up to the 21st century and better. This brick masterpiece is sited perfectly with sweeping views yet very private. The home is perfectly proportioned. The history of this treasured home along with the connection to one of the most famous breeding horses

  MaryBeth O'Hara Ellis Sotheby's Intl Realty

  6 Silvertail Rd, Chester, NY 10918
• 

  Est $722,092 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 5,084 Sq Ft

  66 Murray Dr, Chester, NY 10918

  66 Murray Dr, Chester, NY 10918
• 

  

  /22

  $738,850 Pending

  • Land
  • 561.54 Acres
  • $1,316 per Acre

  234 Old River Rd, Chester, NY 12853

  This property is 562 Ac of Adk field and forest with 2,000 ft. of frontage on the Hudson River, 2 beaver ponds, stream and trails. Structures on this dormant farm include an uninhabited house, barn and shed in need of rehab. An authentic log cabin is situated at a higher elevation above the field, beside an active beaver pond. Adjacent is a 'Morton' building, ideal for storage of equipment and

  John O'Donnell Timberland Realty

  234 Old River Rd, Chester, NY 12853
• 

  $490,900 Sold Feb 13, 2025

  • 1,268 Sq Ft
  • $387/SF
  • 159 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1972

  220 Glenmere Rd, Chester, NY 10918

  You’re going to love the quiet living in this lovely home! It will give you peace of mind, with all new features! New blue siding makes it the most striking home in the neighborhood+ new roof! Stamped concrete walkway & new entry lead you in. Gorgeous kitchen has quartz counters, stylish cabinets, modern lighting, new appliances, pantry and an island with a breakfast bar! The open floor design

  Kathy Dawson Howard Hanna Rand Realty

  220 Glenmere Rd, Chester, NY 10918
• 

  Est $580,998 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,342 Sq Ft

  5 Mari Rd, Chester, NY 10918

  5 Mari Rd, Chester, NY 10918
• 

  /2

  $799,900 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,500 Sq Ft

  40 Mountainside Dr, Chester, NY 10918

  FANTASTIC NEW CONSTRUCTION to be built!! FULLY CUSTOM BUILD opportunity for your DREAM HOME! Wonderful soon to be complete sub-division with mountain-views of Sugar Loaf Mountain in Chester! Additional Information: Amenities:Stall Shower,Storage,ParkingFeatures:2 Car Attached,

  Karen Gauvin Our House Real Estate Group

  40 Mountainside Dr, Chester, NY 10918
• 

  $602,000 Sold Feb 13, 2025

  • 2,698 Sq Ft
  • $223/SF
  • 15 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2000

  19 Mount Ridge Ct, Monroe, NY 10950

  Welcome to 19 Mount Ridge Ct., this 4-bedroom, 2.5-bath colonial with a 1.1 acre lot sits on a serene cul-de-sac in the Monroe-Woodbury School District. This spacious residence boasts high ceilings, gleaming hardwood floors, and a cozy, working fireplace. The well-designed kitchen features an island, perfect for gatherings, while the first-floor master bedroom offers convenient main-level living.

  Christian Baez Keller Williams Hudson Valley

  19 Mount Ridge Ct, Monroe, NY 10950
• 

  Est $458,681 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,358 Sq Ft

  13 Mari Rd, Chester, NY 10918

  13 Mari Rd, Chester, NY 10918
• 

  

  /23

  $455,000

  • 3 Beds
  • 1 Bath
  • 1,561 Sq Ft

  33 Meadow Ave, Chester, NY 10918

  One floor living at it best! Walk out your front door, sit on your rocking chair front porch with your morning coffee & enjoy the mountain views! This 3 bedroom 1 bath ranch offers hardwood flooring throughout main living area & newly update kitchen and bath. Kitchen with plenty of cabinet & counter space.Entertain or BBQ on your private private deck. Plenty of parking in your 1 car garage. Walk

  Ernie Acampora River Realty Services, Inc.

  33 Meadow Ave, Chester, NY 10918
• 

  $567,000 Sold Feb 12, 2025

  • 2,922 Sq Ft
  • $194/SF
  • 63 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1850

  6 Railroad Ave, Chester, NY 10918

  BEAUTIFUL DUPLEX!! Very Well Maintained! Two Units! First Floor Unit has 2 Bedrooms and ! 1/2 Bathrooms! Eat In Kitchen with Granite Counter Tops, Breakfast Nook and Stainless Appliances! Gleaming Hard Wood Floors! Fireplace! Formal Dining Room! Master Bedroom!Beautiful Sun Room! Second Floor Unit is 2 Bedrooms and One Full Bathroom! Master Bedroom Suite with Extra Space for Endless

  Amanda Dnistrian ARC Realty 1 in Sales

  6 Railroad Ave, Chester, NY 10918
• 

  Est $455,799 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,570 Sq Ft

  33 Trotting Dr, Chester, NY 10918

  33 Trotting Dr, Chester, NY 10918
• 

  $520,000 Sold Feb 06, 2025

  • 2,208 Sq Ft
  • $236/SF
  • 169 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1988

  3 Seely Rd, Chester, NY 10918

  PERFECT FOR MULTI-GENERATIONAL LIVING! Monroe-Woodbury School District. Retreat to your own private sanctuary in this Raised Ranch home. Greeted by a sweeping lawn, expansive driveway, and nestled on a large, level lot with a partially wooded backyard, privacy and serenity abound. The heart of this home is its beautifully remodeled, sun-filled kitchen, boasting granite countertops, recessed

  Christina Rowan Howard Hanna Rand Realty

  3 Seely Rd, Chester, NY 10918
• 

  Est $518,183 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,872 Sq Ft

  62 Surrey Rd, Chester, NY 10918

  62 Surrey Rd, Chester, NY 10918

Showing Results 281 - 320, Page 8 of 18