Chester, NY Homes

• 

  $415,000 Sold Jul 03, 2025

  • 1,038 Sq Ft
  • $400/SF
  • 24 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1959

  12 Oak St, Chester, NY 10918

  Located in a peaceful area on a picturesque corner lot in the Village of Chester, this ranch style home in the Cherry Heights neighborhood has been meticulously well maintained with perennial flowers, mature trees, and privacy hedges. Inside, the home boasts a spacious living room with a large picture window that offers views of the front covered porch and a vibrant Japanese maple tree. The

  Jennifer Loprieno Howard Hanna Rand Realty

  12 Oak St, Chester, NY 10918
• 

  Est $753,086 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,838 Sq Ft

  53 Elvis Blvd, Chester, NY 10918

  53 Elvis Blvd, Chester, NY 10918
• 

  

  

  /48

  $1,099,000

  • 4 Beds
  • 2.5 Baths
  • 2,722 Sq Ft

  5 Gabriels Dr, Chester, NY 10918

  Exquisite Colonial Estate: Timeless Grandeur Meets Modern LuxuryNestled gracefully on a private cul-de-sac amidst meticulously manicured grounds, this sprawling Colonial estate offers an unparalleled blend of classic elegance and contemporary comfort. From the moment you approach the stately wrought-iron fenced property and enter through the grand foyer, you are greeted by a magnificent staircase

  Beth Palma Keller Williams Realty

  5 Gabriels Dr, Chester, NY 10918
• 

  $560,000 Sold Jul 01, 2025

  • 2,016 Sq Ft
  • $278/SF
  • 148 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1969

  92 Pickerel Rd, Monroe, NY 10950

  Year end gifts are always wonderful to receive. Welcome to 92 Pickerel road Monroe, New York. A meticulous home awaiting its new owners and features including 3 to 4 bedrooms, 2 full baths, hardwood flooring, recently installed windows, roof, and boiler. A large eat in custom kitchen with granite, stainless appliances and Sub-Zero refrigeration. Dining room is adjacent and well placed.

  Richard Wawrynek Howard Hanna Rand Realty

  92 Pickerel Rd, Monroe, NY 10950
• 

  Est $723,164 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,308 Sq Ft

  40 Valley View Dr, Chester, NY 10918

  40 Valley View Dr, Chester, NY 10918
• 

  

  /50

  $1,300,000

  • 4 Beds
  • 2.5 Baths
  • 3,955 Sq Ft

  90 Main St, Chester, NY 10918

  "The House on the Hill" Proudly offered for the first time in over 70 years. This expansive and character-rich home overlooks the heart of the village while offering nearly 10 acres of space, privacy, and endless potential. Set across three separate parcels totaling 9.68 acres, the property features a main house with approximately 4,000 sq ft, a charming 2-bedroom guest cottage, a large dairy

  STEVEN WROBEL JR. Serhant LLC

  90 Main St, Chester, NY 10918
• 

  $725,000 Sold Jun 30, 2025

  • 3,626 Sq Ft
  • $200/SF
  • 34 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1993

  56 Sunset Ridge Rd, Monroe, NY 10950

  Welcome to 56 Sunset Ridge Road which sits by the private cozy cul-de-sac, a Magnificent backdrop on five luscious acres that envelope this tremendous center hall colonial. A beautiful driveway brings you home to your rocking chair front porch. Two story foyer gives way to the main level formal spaces. Living room, Dining Room, & a separate office leads you to an easy flowing, beautiful, recently

  Moses Schreiber MS Realty Group USA, Inc

  56 Sunset Ridge Rd, Monroe, NY 10950
• 

  Est $675,617 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,226 Sq Ft

  140 Conklingtown Rd, Chester, NY 10918

  140 Conklingtown Rd, Chester, NY 10918
• 

  

  /35

  $1,650,000

  • 6 Beds
  • 4.5 Baths
  • 3,512 Sq Ft

  17 Bonnie Brook Rd, Monroe, NY 10950

  Over 20 sprawling acres with serene life, pond frontage, this is a true sanctuary. Located in Monroe-Woodbury this unique property offer two distinct residences and a spacious barn, providing endless possibilities. House 1: Contemporary Modern originally built in 1965. The first home boasts a generous 3,500+ sq ft of premium living space. Designed with a flexible layout, the home features two

  Pamela Henning Keller Williams Hudson Valley

  17 Bonnie Brook Rd, Monroe, NY 10950
• 

  $225,000 Sold Jun 30, 2025

  • 2,519 Sq Ft
  • $89/SF
  • 56 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1930

  242 Meadow Ave, Chester, NY 10918

  Newly listed Triplex. Showings must be okayed by the tenants. Additional Information: HeatingFuel:Oil Above Ground,

  Kathleen Strong Hudson Valley Griffith

  242 Meadow Ave, Chester, NY 10918
• 

  Est $386,152 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 835 Sq Ft

  70 Conklingtown Rd, Chester, NY 10918

  70 Conklingtown Rd, Chester, NY 10918
• 

  

  /31

  $915,000

  • 3 Beds
  • 2.5 Baths
  • 2,302 Sq Ft

  2 Pine Hill Rd, Chester, NY 10918

  Listed on the National Register of Historic Places in the Sugar Loaf Historic District, this stunning Victorian is a Circa 1910 Sears Roebuck Kit Home (#118 The Clyde). Not only is this your dream home located in beautiful Sugar Loaf, NY, it is also zoned for extensive commercial use. Just a 1-minute walk to the quaint Sugar Loaf Arts & Crafts Village, cafes and Sugar Loaf Performing Arts

  Debbie Walsh SHAHAR Management LLC

  2 Pine Hill Rd, Chester, NY 10918
• 

  $340,000 Sold Jun 25, 2025

  • 1,320 Sq Ft
  • $258/SF
  • 125 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1979

  904 Swan Hollow Rd, Monroe, NY 10950

  WOW!! WOW!! This home in a private community has been totally renovated from kitchen, bathrooms, flooring, painting and more. One of the great features is you can sit outside on your patio and have a total lake view. This complex includes pools, clubhouse, playground and more. You are also close to all nature activities, shopping and easy access to major highways. HOA is 656.98 and includes

  Stephen Ramundo Keller Williams Valley Realty

  904 Swan Hollow Rd, Monroe, NY 10950
• 

  Est $698,662 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,882 Sq Ft

  3966 Summerville Way, Chester, NY 10918

  3966 Summerville Way, Chester, NY 10918
• 

  

  /35

  $399,000

  • 2 Beds
  • 1 Bath
  • 1,484 Sq Ft

  576 Bull Mill Rd, Chester, NY 10918

  A fantastic opportunity for investors or future homeowners! This well-maintained home is set on a large, flat lot in a quiet, nature-filled neighborhood and offers strong rental potential with long-term flexibility. Inside, you’ll find a spacious living room, formal dining area, kitchen, and comfortable layout ideal for everyday living. Recent updates include fresh interior paint (2021), and a

  Lazar Schvimmer Blooming Realty

  576 Bull Mill Rd, Chester, NY 10918
• 

  $624,000 Sold Jun 23, 2025

  • 2,236 Sq Ft
  • $279/SF
  • 66 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1999

  20 Hubshop Rd, Chester, NY 10918

  CAPTIVATING CAPE COD! 1.5 Private Acres! 4 Bedrooms! 2 1/2 Bathrooms! 1 Car Garage! Gorgeous Updated Eat In Kitchen with Granite Counter Tops, Stainless Steel Appliances & Breakfast Nook! Master Bedroom Suite with Walk In Closet Located on the First Floor! Living Room with Double Sided Fireplace! Gleaming Hard Wood Floors! New Carpeting! Recessed Lighting! Laundry Room! Full Basement! Rocking

  Amanda Dnistrian ARC Realty 1 in Sales

  20 Hubshop Rd, Chester, NY 10918
• 

  Est $791,039 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,682 Sq Ft

  1689 Kings Hwy, Chester, NY 10918

  1689 Kings Hwy, Chester, NY 10918
• 

  

  /4

  $350,000

  • Land
  • 5.1 Acres
  • $68,627 per Acre

  0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918

  Very private lot in mature subdivision of large homes. Home site has been cleared and driveway base laid down. With a small amount of brush-clearing in the tree line there can be views of the valley and watershed lands.

  Theresa Powers Keller Williams Realty

  0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
• 

  $763,750 Sold Jun 20, 2025

  • 2,500 Sq Ft
  • $306/SF
  • 69 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1995

  3 Woodridge Dr, Chester, NY 10918

  Welcome to this stunning Center Hall Colonial, a true masterpiece of craftsmanship and modern luxury set on a beautifully landscaped 1.3-acre property in a prestigious executive neighborhood. From its grand facade adorned with masterful stonework to the thoughtfully designed interior, every detail of this home has been meticulously crafted for refined living. The outdoor space is a serene oasis,

  Gina Dudgeon Howard Hanna Rand Realty

  3 Woodridge Dr, Chester, NY 10918
• 

  Est $725,910 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,504 Sq Ft

  272 Bull Mill Rd, Chester, NY 10918

  272 Bull Mill Rd, Chester, NY 10918
• 

  

  /5

  $74,900

  • Land
  • 1.79 Acres
  • $41,844 per Acre

  L4-5 Marina Rd, Chester, NY 12817

  This is two lots combined for better access and development and has beach rights to two beaches shown on map. HOA Owner's association fee includes beach maintenance. HOA board is working toward the possibility of installing a boat docksystem for the future. Presently there is space for non motorized craft on the beaches. Broker (John R. Palermo) is handling this property for his family's LLC

  John Palermo John R. Palermo

  L4-5 Marina Rd, Chester, NY 12817
• 

  $334,900 Sold Jun 20, 2025

  • 1,331 Sq Ft
  • $252/SF
  • 185 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1984

  1610 Whispering Hills, Chester, NY 10918

  Discover your perfect commuter condo in the Whispering Hills Neighborhood of Chester! This beautiful end unit features three spacious bedrooms and two and a half baths. As you step inside, you'll find a bright and airy open living space that showcases the well maintained hardwood floors and charming fireplace, which provides a cozy atmosphere for gatherings during the cooler months. Off the side

  Patricia Sassi RE/MAX Benchmark Realty Group

  1610 Whispering Hills, Chester, NY 10918
• 

  Est $721,221 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,800 Sq Ft

  71 Winding Trail, Chester, NY 10918

  71 Winding Trail, Chester, NY 10918
• 

  

  /18

  $179,900

  • Land
  • 3.14 Acres
  • $57,293 per Acre

  2 Dixon Rd, Chester, NY 12817

  Fish, paddle, build! Your very own 509' of private frontage plus your own mini island on the Schroon River! Over 3 acre buildable lot with driveway in place and power at the road. Just south of the dam (no acess to Schroon Lake). Ideal location for fishing, paddling, rafting & swimming. Conveniently located to the Adirondack Northway and area amenities!

  Angie Mead Gallo Realty ADK Inc

  2 Dixon Rd, Chester, NY 12817
• 

  $460,000 Sold Jun 18, 2025

  • 1,576 Sq Ft
  • $292/SF
  • 20 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1956

  55 Hudson St, Chester, NY 10918

  Nestled on a dead end st in the heart of the Village of Chester, and lovingly cared for by the original family since 1956 is this meticulously maintained 3-bedroom ranch offering all the right elements you're looking for set in a village neighborhood location you simply can't beat. First floor consists of a galley kitchen, dining area, large livingroom with fireplace, full bath, office and two

  Lynelle Alessi Keller Williams Hudson Valley

  55 Hudson St, Chester, NY 10918
• 

  Est $818,105 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,923 Sq Ft

  11 Park Place, Chester, NY 10918

  11 Park Place, Chester, NY 10918
• 

  

  /5

  $46,900

  • Land
  • 7.07 Acres
  • $6,634 per Acre

  L30 Lane Rd, Chester, NY 12853

  You won't want to miss out on this opportunity! A little over 7 acres (2 parcels) in the heart of the Adirondacks. Close proximity to all the local lakes (Schroon Lake, Loon Lake, Brant Lake) & 10 minutes from Gore Mountain.

  Julia Pucciarelli Gallo Realty ADK Inc

  L30 Lane Rd, Chester, NY 12853
• 

  $899,999 Sold Jun 18, 2025

  • 3,167 Sq Ft
  • $284/SF
  • 163 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2023

  29 Meadow Ave, Chester, NY 10918

  The Fabulous Charlotte Model is up, sided and interior paint and trim/mill work work is completed. This 3167 sf ranch is located in a very favorable commuter locale, 5 minutes to all highways. A 500 sf finished bonus room above the garage. The 4 acres on which the home sits, is an exceptional piece of land to own, corner of Cul de sac for additional privacy. The exterior features front & side

  Nancy Sardo BHG Real Estate Green Team

  29 Meadow Ave, Chester, NY 10918
• 

  Est $662,923 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,021 Sq Ft

  243 Bull Mill Rd, Chester, NY 10918

  243 Bull Mill Rd, Chester, NY 10918
• 

  

  /49

  $1,500,000

  206 Greycourt Rd Unit 190, Chester, NY 10918

  **Endless Opportunities Await on This Rare 3.2-Acre Property!** ZONED COMMMERCIAL INDUSTRIAL USEFor the first time in over 50 years, this prime piece of real estate is hitting the market! Nestled right off Route 17 with unbeatable exposure, this unique 3.2-acre property offers **unlimited potential** for investors, developers, or those looking for a special place to call home. Featuring **four

  Susan McMullen eXp Realty

  206 Greycourt Rd Unit 190, Chester, NY 10918
• 

  $551,225 Sold Jun 17, 2025

  • 1,916 Sq Ft
  • $288/SF
  • 38 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1984

  152 Lake Region Blvd, Monroe, NY 10950

  Discover cozy lakeside living in this beautifully updated 4-bedroom, 2.5-bathroom home nestled in the desirable Lake Region Estates community. With 1,916 sq ft of comfortable living space, this move-in ready gem offers the perfect blend of modern updates and serene charm.Enjoy brand new flooring throughout the upstairs, a new roof, Anderson casement windows, and a spacious deck perfect for

  Raynilson Vasquez eXp Realty

  152 Lake Region Blvd, Monroe, NY 10950
• 

  Est $622,840 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,130 Sq Ft

  6 Reilly Rd, Chester, NY 10918

  6 Reilly Rd, Chester, NY 10918
• 

  

  /33

  $89,500

  • Land
  • 12.79 Acres
  • $6,998 per Acre

  3-4 Adirondack Heights Rd, Chester, NY 12817

  Seller financing now available. 12.79 acres of mixed forest and wetlands. Perc tests and engineered plot plans have been completed. APA approved building sites with well & septic locations identified. (2-lots can each be built upon or just have one large lot) Power at the road pedestal box. Tons of hemlock, spruce, and pine trees throughout. Close to Chestertown, 20-minutes to Gore Mountain or

  Walter Swartz Gallo Realty ADK Inc

  3-4 Adirondack Heights Rd, Chester, NY 12817
• 

  $875,000 Sold Jun 13, 2025

  • 4,021 Sq Ft
  • $218/SF
  • 17 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2001

  157 Creamery Pond Rd, Chester, NY 10918

  Welcome to Creamery Estates of Sugarloaf, where your dream home awaits just an hour’s drive from New York City. Nestled within walking distance of the charming downtown hamlet of Sugarloaf, this lovely residence is minutes away from schools, boutique shops, restaurants, grocery stores, the Sugar Loaf Performing Arts Center, wineries, breweries, apple orchards, the Appalachian trails, local

  Carla Terranova Keller Williams Realty

  157 Creamery Pond Rd, Chester, NY 10918
• 

  Est $742,165 Not Listed For Sale

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

  61 Nancy Ln, Chester, NY 10918

  61 Nancy Ln, Chester, NY 10918
• 

  

  /45

  $850,000

  • 4 Beds
  • 2.5 Baths
  • 3,656 Sq Ft

  49 Stone Mountain Trail, Chester, NY 10918

  Stunning curb appeal. Unrivaled privacy. This 3-story, 3,650+ sq. ft. contemporary colonial is a true standout, set on over 7 acres in a private cul-de-sac, blending bold design with year-round comfort. From summer pool days to winter fun on gentle backyard slopes, this estate-style property delivers space, elegance, and adventure in one powerful package.Enter through a grand two-story foyer

  Leon Klein Keller Williams Hudson Valley

  49 Stone Mountain Trail, Chester, NY 10918
• 

  

  /39

  $579,000 Sold Jun 12, 2025

  • 1,665 Sq Ft
  • $348/SF
  • 8 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1989

  2754 Schroon River Rd, Chester, NY 12817

  Cedar sided contemporary with 955' of direct frontage on the stocked Schroon River! Sprawling 6.5 acres with small beach and dock. This property was made for entertaining with ample outdoor space including screened gazebo and tea room that easily doubles as an additional sleeping area. Home office, ample closet space throughout, attached 2C garage, Defiant Encore woodstove. Come play like the

  Angie Mead Gallo Realty ADK Inc

  2754 Schroon River Rd, Chester, NY 12817
• 

  Est $633,988 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,768 Sq Ft

  88 Nancy Ln, Chester, NY 10918

  88 Nancy Ln, Chester, NY 10918
• 

  

  /7

  $874,900

  • 4 Beds
  • 2 Baths
  • 2,466 Sq Ft

  651 Lakes Rd, Monroe, NY 10950

  Rare opportunity to purchase this breath taking one of a kind estate in Monroe that consists of three homes nestled on 3.5 stately landscaped acres affording you peace and privacy! Surrounded by the original stone walls of this compound, this unique oasis offers a huge 50,000-gallon gunite in-ground pool with Italian glass tile, patios overlooking the gorgeous park-like grounds, and a new

  Frank Golio Howard Hanna Rand Realty

  651 Lakes Rd, Monroe, NY 10950
• 

  

  /16

  $60,000 Sold Jun 12, 2025

  • Land
  • 5.34 Acres
  • $11,236 per Acre

  • 30 Days On Market

  116 Carriage Knoll Rd, Chester, NY 12817

  Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

  Walter Swartz Gallo Realty ADK Inc

  116 Carriage Knoll Rd, Chester, NY 12817

Showing Results 121 - 160, Page 4 of 18