Town of Chester, NY Real Estate & Homes For Sale

53 homes

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NEW
COMING SOON 5/29
1 ACRE
$779,000
4 Beds
3.5 Baths
2,948 sqft
270 Bull Mill Road,
Chester, NY 10918
Listing by: Keller Williams Realty
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NEW
COMING SOON 6/6
$419,000
3 Beds
2.5 Baths
1,694 sqft
332 Heritage Lane,
Monroe, NY 10950
Listing by: RE/MAX Prime Properties
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NEW - 2 DAYS AGO
0.29 ACRES
$475,000
3 Beds
2 Baths
1,460 sqft
35 Maple Lane,
Monroe, NY 10950
Listing by: eXp Realty
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OPEN SAT, 1-2PM
COMING SOON 5/27
1.8 ACRES
$590,000
3 Beds
2.5 Baths
2,083 sqft
94 Booth Road,
Chester, NY 10918
Listing by: Compass Greater NY, LLC
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46 ACRES
$399,000
492 Black Meadow Road,
Chester, NY 10918
Listing by: eXp Realty
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0.64 ACRES
$495,000
4 Beds
3 Baths
1,792 sqft
18 Southside Drive,
Monroe, NY 10950
Listing by: Keller Williams Realty
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0.36 ACRES
$499,900
3 Beds
2 Baths
1,778 sqft
1 N Hudson Street,
Chester, NY 10918
Listing by: Keller Williams Hudson Valley
NEW CONSTRUCTION
0.62 ACRES
$849,900
4 Beds
2.5 Baths
3,200 sqft
Lot 3 - 62 Camp Monroe Road,
Monroe, NY 10950
Listing by: Howard Hanna Rand Realty
$370,000
3 Beds
2.5 Baths
1,331 sqft
3815 Whispering Hills Drive,
Chester, NY 10918
Listing by: MK Realty Inc
5.4 ACRES
$799,000
5 Beds
5.5 Baths
5,403 sqft
4 Debbie Court,
Chester, NY 10918
Listing by: Flag Realty Group
AUCTION
Est. $298,400
2 Beds
2 Baths
1,086 sqft
1206 Whispering Hls #151,
Chester, NY 10918
1 ACRE
$550,000
5 Beds
2.5 Baths
1,815 sqft
208 Glenmere Road,
Chester, NY 10918
Listing by: MK Realty Inc
OPEN SUN, 12-2PM
1.3 ACRES
$799,999
3 Beds
2.5 Baths
2,718 sqft
58 Nancy Lane,
Chester, NY 10918
Listing by: Howard Hanna Rand Realty
0.45 ACRES
$450,000
3 Beds
1.5 Baths
1,177 sqft
151 Laroe Road,
Chester, NY 10918
Listing by: Keller Williams Realty
2.7 ACRES
$1,195,000
9 Beds
6.5 Baths
4,965 sqft
19 High Street,
Chester, NY 10918
Listing by: Keller Williams Realty
$425,000
3 Beds
2.5 Baths
1,331 sqft
2722 Whispering Hills,
Chester, NY 10918
Listing by: Artisan Realty
$319,900
2 Beds
1.5 Baths
1,072 sqft
2820 Whispering Hills,
Chester, NY 10918
Listing by: R2M Realty Inc.
0.26 ACRES
$529,900
3 Beds
3 Baths
2,032 sqft
35 Maple Avenue,
Chester, NY 10918
Listing by: RE/MAX Benchmark Realty Group
1 ACRE
$849,900
3 Beds
3 Baths
2,740 sqft
149 Creamery Pond Road,
Chester, NY 10918
Listing by: Keller Williams Realty
3.1 ACRES
$1,100,000
5 Beds
4 Baths
5,312 sqft
53 Gibson Hill Road,
Chester, NY 10918
Listing by: eXp Realty
5.9 ACRES
$1,299,000
4 Beds
3.5 Baths
5,712 sqft
16 Sunset Ridge,
Monroe, NY 10950
Listing by: Serhant LLC
3D VIEW
0.51 ACRES
$569,000
4 Beds
2.5 Baths
2,040 sqft
78 Pickerel Road,
Monroe, NY 10950
Listing by: eXp Realty
NEW CONSTRUCTION
3D VIEW
3.8 ACRES
$1,399,777
4 Beds
4 Baths
4,508 sqft
145 Kings Highway Bypass,
Chester, NY 10918
Listing by: Keller Williams Realty
0.5 ACRES
$875,000
3 Beds
2.5 Baths
2,302 sqft
2 Pine Hill Road,
Chester, NY 10918
Listing by: Ellis Sotheby's Intl Realty
$344,900
3 Beds
2 Baths
1,316 sqft
1311 Whispering Hills,
Chester, NY 10918
Listing by: Keller Williams Realty
1.1 ACRES
$1,159,900
4 Beds
4 Baths
4,624 sqft
16 Lori Lane,
Chester, NY 10918
Listing by: eXp Realty
$559,000
4 Beds
2.5 Baths
1,916 sqft
22 Cambridge Circle,
Monroe, NY 10950
Listing by: Howard Hanna Rand Realty
3D VIEW
1.3 ACRES
$670,000
4 Beds
3 Baths
3,636 sqft
10 Hidden Drive,
Monroe, NY 10950
Listing by: Century 21 Full Service Realty
NEW CONSTRUCTION
0.53 ACRES
$759,900
4 Beds
2.5 Baths
2,250 sqft
90 Pewter Circle,
Chester, NY 10918
Listing by: Keller Williams Realty
0.41 ACRES
$599,000
4 Beds
2 Baths
2,056 sqft
6 Adams Court,
Monroe, NY 10950
Listing by: Keller Williams Realty
0.38 ACRES
$500,000
3 Beds
2 Baths
2,688 sqft
5 N Hudson Street,
Chester, NY 10918
Listing by: Keller Williams Realty
0.43 ACRES
$600,000
5 Beds
3 Baths
2,983 sqft
9 Mount Ridge Court,
Monroe, NY 10950
Listing by: RE/MAX Benchmark Realty Group
FOR SALE BY OWNER
7.2 ACRES
$899,000
4 Beds
3 Baths
2,700 sqft
91 Glenmere Rd,
Chester, NY 10918
NEW CONSTRUCTION
20.18 ACRES
$849,900
4 Beds
2.5 Baths
2,603 sqft
32 Mountainside Drive,
Chester, NY 10918
Listing by: Our House Real Estate Group
NEW CONSTRUCTION
1.6 ACRES
$869,900
4 Beds
2.5 Baths
3,000 sqft
10 Wells Sweep Lane,
Chester, NY 10918
Listing by: Keller Williams Realty
NEW CONSTRUCTION
4.5 ACRES
$879,900
4 Beds
2.5 Baths
3,200 sqft
1414 Kings Highway,
Chester, NY 10918
Listing by: Keller Williams Realty
5.7 ACRES
$299,000
552 Pine Hill Road,
Chester, NY 10918
Listing by: eRealty Advisors, Inc
1.8 ACRES
$699,000
4 Beds
2.5 Baths
3,120 sqft
558 Pine Hill Road,
Chester, NY 10918
Listing by: eRealty Advisors, Inc
$377,000
3 Beds
2.5 Baths
1,331 sqft
1221 Whispering Hls,
Chester, NY 10918
Listing by: BUY NY REALTY LLC
$149,900
2 Imperial Park,
Chester, NY 10918
Listing by: HomeSmart Homes & Estates

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Walton Park
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Neighborhood stats provided by third party data sources.

What Locals Say about Town of Chester

Jenelle Rivera
Visitor
11mo ago
"Quiet and pretty family oriented very clean feels safe and there’s sufficient parking for the residents"
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Jenelle Rivera
Resident
1y ago
"Very close to major highways and traffic is always minimal. Shopping Centers and major supermarkets are within walking distance "
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Kyle McNerney
Resident
2y ago
Walton Park, Monroe
"I don’t have much to say on this matter. Our neighbors are great and we have enjoyed the quietness of the area. There are not an abundance of community events that we are aware of. "
3
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Trulia User
Resident
5y ago
"There's plenty of areas with sidewalks to walk your dog throughout most of town. My apartment complex has a dog park "
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Jennifer G.
Resident
6y ago
"I have two years living here. Great place to raise a family. Friendly and safe neighborhood. The kids love it as well."
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Kcouponsdeals
Resident
6y ago
"this is a great village, and neighborhood to live in lots of community involvement, family activities, close to transportation and shopping."
1
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Kcouponsdeals
Resident
6y ago
"this is a great family neighborhood. You can walk to store and NYC bus stop. it's great for kids sports, trick or treating ,etc. there are also arts and theater programs in the area."
2
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DEIRDRE B.
Resident
6y ago
"I take the Shortline bus to NYC. 1 hour and 15 minutes more or less plus train from Port. It’s about $450/month including Metrocard. Shortline has become less reliable recently. "
3
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Missmtrejo
Resident
7y ago
"It’s a safe community and our neighbors have become friends! We have lived here for 20 years. It’s a great place for children to make friends and feel safe in their environment when they are outside playing. "
1
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Melissa Kyles
Resident
7y ago
"I lived in Chester when I was a children to adulthood. Great place to live. Outstanding school district. Wish I never moved away."
4
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Dianerene
Resident
7y ago
"Street fairs, community parades, concerts and so much more. The location is awesome and neighbors aren’t overly nosy yet friendly."
2
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Dawnstephenson42
Resident
7y ago
"fireworks night football h.s small town feel community garage sales schools mom and pop shops nearby wineries holiday parades farmers market"
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Suzzzzzzz64
Resident
7y ago
"I live in this area for 11 years my neighborhood is great and the people around here are really nice "
5
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Dianerene
Resident
7y ago
"My commute is excellent. I have a 3 minute commute to the park and ride bus and local stores. Easy to get around by foot if needed."
1
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Zachary M.
Resident
7y ago
Walton Park, Monroe
"It’s a mediate drive, to shopping malls and and the grocery store about a half an hour drive to the mall in Middletown it’s not bad since I work there and go there everyday "
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Ebobec18
Resident
8y ago
"Safety its a neighborhood very secure the police its annoying but make sense because that its part of what make this place so safe. I can go out at 3pm or 3am and i will fill safe any time. "
1
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Tara R.
Resident
8y ago
"i love chester unfortunately there arent many houses for purchase in my range for a single mom. wanted my kids to stay in there school there on sports teams."
5
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inwalker
11y ago
"Easy commute to work in New York City via route 17M (2 miles) or bus via Short Line (2 miles) yet no congested roads to deal with. Great neighbors. Park within walking distance (football, soccer, baseball and children's recreation area). Large variety of Restaurants to satisfy your all your cravings. Orange Regional Medical center 5 miles via 17M."
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Based on information submitted to the MLS GRID as of 2026-02-06 15:18:24 PST. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. Click here for more information

Town of Chester, NY Real Estate & Homes For Sale

53 homes

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What Locals Say about Town of Chester

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