Chester, NY Homes

• 

  Est $730,543

  Not Listed For Sale

  392 Bellvale Rd, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft
  • Built 1993

  392 Bellvale Rd, Chester, NY 10918

  Last Sold Summary

  • 68 Days On Market
• 

  

  /2

  $299,000

  $51K PRICE DROP

  • Land
  • 5.7 Acres
  • $52,456 per Acre

  552 Pine Hill Rd, Chester, NY 10918

  Beautiful 5.7-acre residential parcel located in the Town of chester, offering an exceptional opportunity to build your custom dream home in a peaceful, private setting. With ample space for a spacious residence and outdoor living areas (subject to town approvals), this property combines natural surroundings with convenient access to nearby amenities, schools, and major roadways. Adjacent to 558

  Charnie Guttmann eRealty Advisors, Inc

  552 Pine Hill Rd, Chester, NY 10918
• 

  Est $661,690

  Not Listed For Sale

  63 Hambletonian Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,310 Sq Ft
  • Built 1997

  63 Hambletonian Rd, Chester, NY 10918

  Last Sold Summary

  • 25 Days On Market
• 

  

  

  /23

  $68,900

  $19K PRICE INCREASE

  • Land
  • 3.05 Acres
  • $22,590 per Acre

  82 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

  82 Carriage Knoll Rd, Chester, NY 12817
• 

  Est $595,501

  Not Listed For Sale

  73 Hambletonian Rd, Chester, NY 10918

  • 5 Beds
  • 2 Baths
  • 2,680 Sq Ft
  • Built 1948

  73 Hambletonian Rd, Chester, NY 10918

  Last Sold Summary

  • 17 Days On Market
• 

  

  /29

  $720,000

  • 4 Beds
  • 2.5 Baths
  • 1,718 Sq Ft

  26 Bridle Ln, Chester, NY 10918

  From the moment you arrive, it's clear this is a home whose character and setting are best experienced firsthand. The bright, open-concept living area features vaulted ceilings and abundant natural light, creating an inviting space for everyday living and entertaining. A beautiful den with two walls of windows and a gas fireplace overlooks the pool and surrounding landscape. The thoughtfully

  David White Owner Entry.com

  26 Bridle Ln, Chester, NY 10918
• 

  Est $783,897

  Not Listed For Sale

  15 Banker Dr, Chester, NY 10918

  • 4 Beds
  • 3.5 Baths
  • 2,396 Sq Ft
  • Built 2000

  15 Banker Dr, Chester, NY 10918

  Last Sold Summary

  • 32 Days On Market
• 

  

  /50

  $623,900

  $125K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,524 Sq Ft

  17 Woodridge Dr, Chester, NY 10918

  Beautiful Colonial set on just under an acre of meticulously landscaped property, offering breathtaking sunset views from a very private backyard. Great spacious front porch! On a quiet cul-de-sac, this home features a stunning in-ground pool with a new heater, cover & pump. Pool filter, and liner are about 4 years young. The pools heating system runs on propane tank. Entire home was freshly

  Sharon Kushner eXp Realty

  17 Woodridge Dr, Chester, NY 10918
• 

  Est $643,845

  Not Listed For Sale

  1301 Kings Hwy, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,676 Sq Ft
  • Built 1835

  1301 Kings Hwy, Chester, NY 10918

  Last Sold Summary

  • 146 Days On Market
• 

  

  /24

  $74,000

  $10K PRICE DROP

  • Land
  • 2.84 Acres
  • $26,056 per Acre

  38 Granite Ridge Rd, Chester, NY 12817

  Private 2.84-acre partially cleared, buildable lot in a peaceful setting with proposed home and septic locations. Property features a gravel driveway with camper pad, Amish-built shed on gravel base, fire pit, and walking trail. Infrastructure in place includes 200-amp underground electric service plus 30-amp and 50-amp RV hookups. Conveniently located minutes from Cronin's Golf Resort, Friends

  Nicholas Khachadourian KW Platform

  38 Granite Ridge Rd, Chester, NY 12817
• 

  Est $1,244,160

  Not Listed For Sale

  6 Silvertail Rd, Chester, NY 10918

  • 6 Beds
  • 4.5 Baths
  • 5,127 Sq Ft
  • Built 1794

  6 Silvertail Rd, Chester, NY 10918

  Last Sold Summary

  • 304 Days On Market
• 

  

  /7

  $39,500

  • Land
  • 2.38 Acres
  • $16,597 per Acre

  22 Carriage Knolls Rd, Chester, NY 12817

  Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for a

  Walter Swartz Gallo Realty ADK Inc

  22 Carriage Knolls Rd, Chester, NY 12817
• 

  Est $1,388,361

  Not Listed For Sale

  10 Silvertail Rd, Chester, NY 10918

  • 4 Beds
  • 4.5 Baths
  • 5,007 Sq Ft
  • Built 2006

  10 Silvertail Rd, Chester, NY 10918

  Last Sold Summary

  • 31 Days On Market
• 

  

  /26

  $275,000

  • 2 Beds
  • 1 Bath
  • 1,062 Sq Ft

  804 Swan Hollow Rd, Monroe, NY 10950

  Welcome Home! Well maintained two bedroom unit with lake and mountain views. Spacious living room with access to a private balcony. Eat in kitchen has updated counter tops and new appliances. Both bedrooms have ample closet space. Windridge is a quiet community conveniently located minutes from town. Great commuter location. Amenities include pool, playground, tennis and basketball courts,

  Valerie Quinn Keller Williams Realty

  804 Swan Hollow Rd, Monroe, NY 10950
• 

  Est $1,079,447

  Not Listed For Sale

  40 Deer Trail Rd, Chester, NY 10918

  • 4 Beds
  • 4.5 Baths
  • 3,114 Sq Ft
  • Built 1991

  40 Deer Trail Rd, Chester, NY 10918

  Last Sold Summary

  • 387 Days On Market
• 

  

  /33

  $185,000

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft

  28 Olmstedville Rd, Chester, NY 12817

  Older home in a completely private location - in the center of a Hamlet. Trees and bushes make the home invisible from the road. The back border is Town land with Public beach area on Trout Brook Good for canoeing. Covered porch is on two sides of the house. The interior has beautiful real wood floors. Main level is kitchen, dining room, living room, full bath and laundry area. Upstairs are 3

  Heidemarie Lane Big Hat Realty

  28 Olmstedville Rd, Chester, NY 12817
• 

  Est $485,887

  Not Listed For Sale

  208 Glenmere Rd, Chester, NY 10918

  • 5 Beds
  • 2.5 Baths
  • 1,815 Sq Ft
  • Built 1900

  208 Glenmere Rd, Chester, NY 10918

  Last Sold Summary

  • 43 Days On Market
• 

  

  /16

  $37,500

  • Land
  • 2 Acres
  • $18,750 per Acre

  13 Carriage Knolls Rd, Chester, NY 12817

  Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for a

  Walter Swartz Gallo Realty ADK Inc

  13 Carriage Knolls Rd, Chester, NY 12817
• 

  Est $500,685

  Not Listed For Sale

  220 Glenmere Rd, Chester, NY 10918

  • 3 Beds
  • 1.5 Baths
  • 1,268 Sq Ft
  • Built 1972

  220 Glenmere Rd, Chester, NY 10918

  Last Sold Summary

  • 159 Days On Market
• 

  

  /45

  $499,000

  $30K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,060 Sq Ft

  63 Hubshop Rd, Chester, NY 10918

  Nestled on a quiet road off the beaten path, this serene 4-bedroom, 2.5-bathroom Colonial offers the perfect blend of secluded tranquility and commuter convenience. The main level features a traditional layout with a spacious living room, formal dining room, and a cozy recreation room perfect for relaxing. The functional eat-in kitchen serves as the heart of the home, while all four bedrooms are

  Charles Moore Keller Williams Realty

  63 Hubshop Rd, Chester, NY 10918
• 

  Est $533,749

  Not Listed For Sale

  226 Glenmere Rd, Chester, NY 10918

  • 4 Beds
  • 1.5 Baths
  • 1,530 Sq Ft
  • Built 1976

  226 Glenmere Rd, Chester, NY 10918

  Last Sold Summary

  • 203 Days On Market
• 

  

  /32

  $329,900

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,316 Sq Ft

  1311 Whispering Hills Unit 96, Chester, NY 10918

  Experience Elevated Living: Your Private Hudson Valley Retreat at 1311 Whispering Hills Welcome to a home that offers more than just square footage—it offers a lifestyle change. Nestled in the scenic rolling hills of Orange County, 1311 Whispering Hills is a masterclass in modern suburban living. This meticulously maintained residence captures the essence of "home" from the moment you step

  Michael Jenney Keller Williams Realty

  1311 Whispering Hills Unit 96, Chester, NY 10918
• 

  Est $369,416

  Not Listed For Sale

  464 Pine Hill Rd, Chester, NY 10918

  • 3 Beds
  • 1 Bath
  • 920 Sq Ft
  • Built 1930

  464 Pine Hill Rd, Chester, NY 10918

  Last Sold Summary

  • 19 Days On Market
• 

  

  /50

  $1,195,000

  • 4 Beds
  • 3.5 Baths
  • 4,281 Sq Ft

  22 Goshen Rd, Chester, NY 10918

  Welcome to an unparalleled expression of luxury living in the Town of Chester. Built in 2003, this custom-built Cape May/Colonial estate designed by award winning architect Larry Belk estate spans 4,281 square feet of meticulously designed living space, masterfully balancing grand entertaining spaces with intimate everyday comfort. From the moment you arrive, exceptional craftsmanship is on

  Martha Randazzo Howard Hanna Rand Realty

  22 Goshen Rd, Chester, NY 10918
• 

  Est $797,689

  Not Listed For Sale

  152 Gibson Hill Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 3,176 Sq Ft
  • Built 1997

  152 Gibson Hill Rd, Chester, NY 10918

  Last Sold Summary

  • 230 Days On Market
• 

  

  /49

  $735,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 3,356 Sq Ft

  55 Beverly Rd, Chester, NY 10918

  Welcome to 55 Beverly Road, Chester—A Stunning, Move-In Ready Home This beautifully updated 3,156 square-foot home blends timeless charm with modern upgrades, offering space, comfort, and style throughout. The expansive floor plan features bright, inviting living areas with soaring vaulted ceilings, gleaming hardwood floors throughout, and a cozy masonry fireplace that serves as a perfect focal

  Jay Himelson Howard Hanna Rand Realty

  55 Beverly Rd, Chester, NY 10918
• 

  Est $693,651

  Not Listed For Sale

  27 Beverly Rd, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 2,511 Sq Ft
  • Built 1995

  27 Beverly Rd, Chester, NY 10918

  Last Sold Summary

  • 57 Days On Market
• 

  

  /16

  $65,000

  • Land
  • 1 Acre
  • $65,000 per Acre

  888 Landon Hill Rd, Chester, NY 12817

  One acre building lot. Property is cleared for building, 200 amp electric service installed and a point well on the property. There is currently a 14x40 ''tiny home'' on the property that can be purchased separately or the seller will remove. Minutes from Pottersville, close to Chestertown and Schroon Lake. Appx 20 mins to Gore Mnt Ski Center, 15 mins to Schroon Lake and only 10 mins from Loon

  Kelli May Better Way Realty

  888 Landon Hill Rd, Chester, NY 12817
• 

  Est $828,139

  Not Listed For Sale

  3 Sunset Ridge Rd, Monroe, NY 10950

  • 4 Beds
  • 3.5 Baths
  • 3,524 Sq Ft
  • Built 1996

  3 Sunset Ridge Rd, Monroe, NY 10950

  Last Sold Summary

  • 94 Days On Market
• 

  

  /49

  $999,900

  $200K PRICE DROP

  • 4,032 Sq Ft

  206 Greycourt Rd, Chester, NY 10918

  INCREDIBLE PROPERTY!!! MUNICIPAL WATER!!! MONROE WOODBURY SCHOOL DISTRICT!!! Welcome to 206 Greycourt Road, Chester, NY A truly rare and remarkable offering in the heart of Orange County, Presenting an extraordinary opportunity to acquire a standout property with exceptional visibility, flexible “ OP” zoning, multiple structures, and limitless potential. Positioned on one of Chester's most highly

  Frank Muccari Cronin & Company Real Estate

  206 Greycourt Rd, Chester, NY 10918
• 

  Est $868,408

  Not Listed For Sale

  55 Brookview Dr, Monroe, NY 10950

  • 3 Beds
  • 4 Baths
  • 2,907 Sq Ft
  • Built 1993

  55 Brookview Dr, Monroe, NY 10950

  Last Sold Summary

  • 21 Days On Market
• 

  Est $991,659

  Not Listed For Sale

  46 Brookview Dr, Monroe, NY 10950

  • 5 Beds
  • 5 Baths
  • 4,200 Sq Ft
  • Built 1993

  46 Brookview Dr, Monroe, NY 10950

  Last Sold Summary

  • 146 Days On Market
• 

  Est $1,170,140

  Not Listed For Sale

  11 Sunfish Ln, Monroe, NY 10950

  • 5 Beds
  • 3 Baths
  • 4,198 Sq Ft
  • Built 1996

  11 Sunfish Ln, Monroe, NY 10950

  Last Sold Summary

  • 64 Days On Market
• 

  Est $769,044

  Not Listed For Sale

  8 Reputation Dr, Chester, NY 10918

  • 4 Beds
  • 4 Baths
  • 3,347 Sq Ft
  • Built 1986

  8 Reputation Dr, Chester, NY 10918

  Last Sold Summary

  • 96 Days On Market
• 

  Est $507,115

  Not Listed For Sale

  41 Sugarloaf Mountain Rd, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,296 Sq Ft
  • Built 1986

  41 Sugarloaf Mountain Rd, Chester, NY 10918

  Last Sold Summary

  • 41 Days On Market
• 

  Est $618,361

  Not Listed For Sale

  104 Trout Brook Rd, Monroe, NY 10950

  • 3 Beds
  • 2 Baths
  • 2,232 Sq Ft
  • Built 1999

  104 Trout Brook Rd, Monroe, NY 10950

  Last Sold Summary

  • 82 Days On Market
• 

  Est $719,454

  Not Listed For Sale

  52 Creamery Pond Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,661 Sq Ft
  • Built 1999

  52 Creamery Pond Rd, Chester, NY 10918

  Last Sold Summary

  • 35 Days On Market
• 

  Est $708,329

  Not Listed For Sale

  46 Creamery Pond Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,792 Sq Ft
  • Built 1999

  46 Creamery Pond Rd, Chester, NY 10918

  Last Sold Summary

  • 48 Days On Market
• 

  Est $721,088

  Not Listed For Sale

  125 Creamery Pond Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,658 Sq Ft
  • Built 1997

  125 Creamery Pond Rd, Chester, NY 10918

  Last Sold Summary

  • 22 Days On Market
• 

  Est $659,632

  Not Listed For Sale

  146 Pine Hill Rd, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 2,414 Sq Ft
  • Built 1987

  146 Pine Hill Rd, Chester, NY 10918

  Last Sold Summary

  • 82 Days On Market

Showing Results 401 - 440, Page 11 of 18