$450,000
Pending
- 3 Beds
- 2 Baths
- 1,882 Sq Ft
5 Roggia Rd, Chester, NY 10918
Nazma Sooknanan
Nazma Real Estate LLC
(845) 606-3972
6,841
Chester, NY Homes
-
5 Roggia Rd, Chester, NY 10918
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$2,695 Per Month
- 3 Beds
- 1 Bath
- 2,386 Sq Ft
- Apartment for Rent
28 Academy Ave Unit 2, Chester, NY 10918
28 Academy Ave Unit 2, Chester, NY 10918 -
$1,225,000
Sold Apr 17, 202610 Damian Ct, Chester, NY 10918
- 11 Beds
- 6.5 Baths
- 4,327 Sq Ft
- Built 2004
Last Sold Summary
- 11% Below List Price
- $283/SF
- 47 Days On Market
Current Estimated Value $1,278,785
Last Listing Agent Elimelech Kremer MS Realty Group USA, Inc
10 Damian Ct, Chester, NY 10918 -
Not Listed For Sale116 Carriage Knoll Rd, Chester, NY 12817
Last Sold Summary
- 30 Days On Market
-
$1,100,000
- 5 Beds
- 4 Baths
- 5,312 Sq Ft
53 Gibson Hill Rd, Chester, NY 10918
53 Gibson Hill Rd, Chester, NY 10918
Ammar Iqbal
eXp Realty
(845) 328-2396
-
$4,000 Per Month
- 6 Beds
- 2 Baths
- House for Rent
5 Laroc Rd, Chester, NY 10918
5 Laroc Rd, Chester, NY 10918Property Id: 1802590Stunning Home with Expansive Yard and Abundant Storage!Welcome to this incredible property, boasting a massive backyard perfect for outdoor entertaining! Enjoy warm weather gatherings on the spacious deck, and make the most of the two sheds for storing tools, equipment, and more.This fantastic home also features:- 1 garage for secure vehicle
(845) 572-1279
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$635,000
Sold Jun 22, 202625 Sugarloaf Mountain Rd, Chester, NY 10918
- 3 Beds
- 2.5 Baths
- 1,954 Sq Ft
- Built 1999
Last Sold Summary
- $325/SF
- 29 Days On Market
Current Estimated Value $627,942
Last Listing Agent Frank Muccari Cronin & Company Real Estate
25 Sugarloaf Mountain Rd, Chester, NY 10918 -
Not Listed For Sale
2754 Schroon River Rd, Chester, NY 12817
- 3 Beds
- 2 Baths
- 1,665 Sq Ft
- Built 1989
Last Sold Summary
- 8 Days On Market
-
$730,000
$10K PRICE DROP Pending- 4 Beds
- 3.5 Baths
- 2,780 Sq Ft
7 Park Place, Chester, NY 10918
7 Park Place, Chester, NY 10918
Luanne McGann
Century 21 Full Service Realty
(845) 447-0221
-
$2,000 Per Month
- 1 Bed
- 1 Bath
- 800 Sq Ft
- Condo for Rent
7 Kennedy Ln Unit 3, Monroe, NY 10950
7 Kennedy Ln Unit 3, Monroe, NY 10950Property Id: 2505575Welcome to this well-kept 1 bedroom + extra bonus room apartment located at — perfect for anyone needing a little extra space for a home office, guest room, or creative setup.•1 large bedroom + versatile bonus room•Private front & back entrances•Covered patio + backyard access•Small private yard space•Metal shed for extra storage•Off-street
(845) 604-9599
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$43,000
Sold Oct 31, 2025L17 Vanderwalker Rd, Chester, NY 12817
- Land
- 4 Acres
- $10,750 per Acre
Last Sold Summary
- 12% Below List Price
- 5 Days On Market
Last Listing Agent Zachary Layton Four Seasons Sotheby's International Realty
L17 Vanderwalker Rd, Chester, NY 12817 -
Est $486,485
Not Listed For Sale495 Laroe Rd, Chester, NY 10918
- 3 Beds
- Built 2025
Last Sold Summary
- 170 Days On Market
-
$327,000
Pending- 2 Beds
- 2 Baths
- 1,316 Sq Ft
2323 Whispering Hills Unit 213, Chester, NY 10918
2323 Whispering Hills Unit 213, Chester, NY 10918
Luanne McGann
Century 21 Full Service Realty
(845) 516-8714
-
$2,100 Per Month
- 2 Beds
- 1 Bath
- 1,000 Sq Ft
- House for Rent
1358 Kings Hwy, Chester, NY 10918
1358 Kings Hwy, Chester, NY 10918Quintessential Sugar Loaf Cottage, newly renovated inside, featuring expansive windows in the front living space, new LVP Flooring throughout, new kitchen with plenty of cabinetry, open shelving and a bar style countertop for extra prep space or entertaining. The space also features an extra large pantry and a new spacious sunlit bathroom with stand up shower. First bedroom is on the main floor
Christine DeLuca Corcoran Baer & McIntosh
-
$320,000
Sold Mar 11, 20262912 Whispering Hills, Chester, NY 10918
- 2 Beds
- 1 Bath
- 1,084 Sq Ft
- Built 1987
Last Sold Summary
- 5% Above List Price
- $295/SF
- 19 Days On Market
Current Estimated Value $312,730
Last Listing Agent Rebecca Matta-Candela Keller Williams Realty
2912 Whispering Hills, Chester, NY 10918 -
Est $748,151
Not Listed For Sale303 Sugarloaf Mountain Rd, Chester, NY 10918
- 4 Beds
- 3 Baths
- 2,287 Sq Ft
- Built 2024
Last Sold Summary
- 35 Days On Market
-
$450,000
Pending- 4 Beds
- 2 Baths
- 1,642 Sq Ft
82 Southside Dr, Monroe, NY 10950
82 Southside Dr, Monroe, NY 10950
Ammar Iqbal
eXp Realty
(329) 214-0985
-
$3,795 Per Month
- 3 Beds
- 2.5 Baths
- 1,796 Sq Ft
- Spacious Mountain View Home in Sugar Loaf – Pet Friendly & Move-In Ready
4 Wright Rd, Chester, NY 10918
4 Wright Rd, Chester, NY 10918Welcome to this beautifully maintained home nestled in a quiet, family-friendly neighborhood with stunning mountain views. Located less than a 10-minute walk from Valkyrie Coffee, the Indigo Collective salon, and the heart of Sugar Loaf, you'll enjoy easy access to unique shops, restaurants, and local attractions. The village's annual May festival transforms the streets into a vibrant
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$260,000
Sold Mar 11, 20262104 Whispering Hills, Chester, NY 10918
- 3 Beds
- 2.5 Baths
- 1,331 Sq Ft
- Built 1984
Last Sold Summary
- 13% Below List Price
- $195/SF
- 24 Days On Market
Current Estimated Value $277,956
Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales
2104 Whispering Hills, Chester, NY 10918 -
Est $116,451
Not Listed For Sale30 Mount Ridge Ct, Monroe, NY 10950
Last Sold Summary
- 49 Days On Market
-
$1,139,900
$20K PRICE DROP- 4 Beds
- 5 Baths
- 4,624 Sq Ft
16 Lori Ln, Chester, NY 10918
16 Lori Ln, Chester, NY 10918
Randolph Rogers
eXp Realty
(845) 493-2930
-
$5,300 Per Month
- 4 Beds
- 2 Baths
- 3,412 Sq Ft
- House for Rent
66 Murray Dr, Chester, NY 10918
66 Murray Dr, Chester, NY 10918Welcome to Refined Living — A Contemporary Ranch renovated for Elevated Year-Round Living with ease, entertainment and privacy! Perfectly set on 1.2 acres with Mountain views just one hour from New York City, this FULLY FURNISHED and fully equipped 3,412 square-foot home provides the convenience of one level living blended with the luxury of upscale design features. The bright and open Foyer
Tehillah Deslandes Howard Hanna Rand Realty
-
$735,000
Sold Jul 21, 2025189 Creamery Pond Rd, Chester, NY 10918
- 4 Beds
- 2.5 Baths
- 2,980 Sq Ft
- Built 2004
Last Sold Summary
- 5% Above List Price
- $247/SF
- 19 Days On Market
Current Estimated Value $732,824
Last Listing Agent Patricia Brady Keller Williams Realty
189 Creamery Pond Rd, Chester, NY 10918 -
Est $1,355,811
Not Listed For Sale154 Hambletonian Rd, Chester, NY 10918
- 4 Beds
- 3.5 Baths
- 4,350 Sq Ft
- Built 2013
Last Sold Summary
- 24 Days On Market
-
$369,900
Pending- 3 Beds
- 2.5 Baths
- 1,331 Sq Ft
3910 Whispering Hills, Chester, NY 10918
3910 Whispering Hills, Chester, NY 10918
Randolph Rogers
eXp Realty
(845) 957-9249
-
$2,670 Per Month
- 2 Beds
- 1.5 Baths
- 1,086 Sq Ft
- Townhouse for Rent
1907 Whispering Hills, Chester, NY 10918
1907 Whispering Hills, Chester, NY 10918Welcome home to the highly desirable Whispering Hills Community in Chester School District. This rental features 2 bedrooms, 1.5 bathrooms, and a two car garage for extra storage. Enjoy a cozy fireplace in your spacious living room, kitchen with tile flooring for easy cleanup, and a patio right outside your front sliding doors for summer night enjoyment after taking a dip in the community pool.
Erin Hansford Stonewall Realty Group LLC
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$290,000
Sold Apr 09, 20263308 Whispering Hills Dr, Chester, NY 10918
- 2 Beds
- 1.5 Baths
- 1,072 Sq Ft
- Built 1984
Last Sold Summary
- 3% Below List Price
- $271/SF
- 39 Days On Market
Current Estimated Value $293,327
Last Listing Agent Joseph Paoli Howard Hanna Rand Realty
3308 Whispering Hills Dr, Chester, NY 10918 -
Not Listed For Sale
L47 Cobble Creek Rd, Chester, NY 12853
Last Sold Summary
- 11 Days On Market
-
$350,000
$50K PRICE INCREASE- Land
- 5.1 Acres
- $68,627 per Acre
0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918 -
$2,900 Per Month
- 3 Beds
- 1.5 Baths
- 1,600 Sq Ft
- Apartment for Rent
168 Pine Hill Rd Unit 1, Chester, NY 10918
168 Pine Hill Rd Unit 1, Chester, NY 10918INLCUDES UTILITIES, HEAT & HOT WATER!! Welcome to Unit #1 of 168 Pine Hill Rd. This lovely three bedroom, 1.5 bath apartment offers beautiful views with lots of natural light, an eat in kitchen with stainless steel refrigerator and stove (gas) as well as washer and dryer for added convenience, 3 nice sized bedroom. Easy access- no steps to enter the two level unit. There is a wrap around driveway
Claudia Lepore Keller Williams Realty
-
$323,500
Sold Aug 11, 202598 High St, Chester, NY 10918
- 4 Beds
- 1.5 Baths
- 1,360 Sq Ft
- Built 1950
Last Sold Summary
- 5% Below List Price
- $238/SF
- 35 Days On Market
Current Estimated Value $348,670
Last Listing Agent Zachary Foley eXp Realty
98 High St, Chester, NY 10918 -
Est $306,849
Not Listed For Sale4401 Whispering Hills Dr, Chester, NY 10918
- 2 Beds
- 1 Bath
- 1,118 Sq Ft
- Built 1989
Last Sold Summary
- 30 Days On Market
-
$48,000
- Land
- 3.6 Acres
- $13,333 per Acre
1414 N Gore Rd, Chester, NY 12817
1414 N Gore Rd, Chester, NY 12817 -
$3,399 Per Month
- 4 Beds
- 2 Baths
- 2,084 Sq Ft
- House for Rent
8 Hickory Ln, Monroe, NY 10950
8 Hickory Ln, Monroe, NY 10950Single-family spacious bi-level in a beautiful neighborhood in Monroe. Private In Law Suite Own Entrance No Stairs fully-equipped ,The main floor offers an open living and dining room three nice size bedrooms and a full bath and kitchen with appliances, The lower level has a private entrance and a beautiful size family room and a bedroom plus an office room and kitchen with
Eliezer Safdie Sage Realty Center LLC
-
$610,000
Sold Mar 12, 202644 Cedar Pond Ln, Chester, NY 10918
- 3 Beds
- 2 Baths
- 1,876 Sq Ft
- Built 1991
Last Sold Summary
- 2% Above List Price
- $325/SF
- 48 Days On Market
Current Estimated Value $638,624
Last Listing Agent Ammar Iqbal eXp Realty
44 Cedar Pond Ln, Chester, NY 10918 -
Not Listed For Sale
4120 Whispering Hills Dr, Chester, NY 10918
- 2 Beds
- 1.5 Baths
- 1,282 Sq Ft
- Built 1989
Last Sold Summary
- 69 Days On Market
-
$1,000,000
- 4 Beds
- 2.5 Baths
- 3,955 Sq Ft
1 Oakland Ave, Chester, NY 10918
1 Oakland Ave, Chester, NY 10918
Christina Rowan
Howard Hanna Rand Realty
(845) 237-3716
-
$2,200 Per Month
- 2 Beds
- 1 Bath
- 900 Sq Ft
- Townhouse for Rent
82 High St Unit 5, Chester, NY 10918
82 High St Unit 5, Chester, NY 10918Very bright and spacious top-floor Penthouse apartment! Come see this open layout floorplan. The updated kitchen has a new stainless steel refrigerator and dishwasher. The Primary bedroom has large double closets and can accommodate a king-size bed. The living room/dining room combination is bright and sun-filled, with plenty of windows and an outside deck. You’ll appreciate the convenience of
Lynda Hoss Weichert Realtors
-
$320,000
Sold Feb 13, 20262812 Whispering Hills Unit 577, Chester, NY 10918
- 2 Beds
- 1 Bath
- 1,084 Sq Ft
- Built 1984
Last Sold Summary
- 10% Above List Price
- $295/SF
- 22 Days On Market
Current Estimated Value $314,539
Last Listing Agent Kathy White Exit Realty Connections
2812 Whispering Hills Unit 577, Chester, NY 10918 -
Not Listed For Sale
3111 Whispering Hills Dr, Chester, NY 10918
- 3 Beds
- 2 Baths
- 1,316 Sq Ft
- Built 1987
Last Sold Summary
- 50 Days On Market
Showing Results 1 - 40, Page 1 of 18
Home Prices in Chester, NY
The median home sale price in Chester, NY is $486,500, down 7% year-over-year. Homes in Chester sell in 59 days on average, compared to the national average of 58 days.
Home Price Trends
|
Median Sale Price
$486,500
|
Median Single Family Sale Price
$657,500
|
|
Median Townhouse Sale Price
$324,950
|
Median 2 Bedroom Sale Price
$310,000
|
|
Average Price Per Sq Ft
$274
|
Number of Homes for Sale
53
|
|
Last 12 months Home Sales
86
|
Months of Supply
7.40
|
|
Median List Price
$582,499
|
Median Change From 1st List Price
0%
|
|
Median Home Sale Price YoY Change
-7%
|
|
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