HomeSmart Homes and Estates
  • Home
  • Search
  • Buy
    1. Affordability Calculator
    2. Featured Listings
  • Sell
    1. Home
    2. Sell My Home
    3. Market Snapshot
  • Home Valuation
  • About
    1. About Us
    2. Reviews
    3. Preferred Vendors
  • Contact Us
  • MORE
    1. My Homes
    2. My Tours
    3. My Favorites
    4. My Searches
  • Sign In
  • Register
Price
  • Any
  • $ 100,000
  • $ 150,000
  • $ 200,000
  • $ 400,000
  • $ 800,000
  • Any
  • $ 200,000
  • $ 300,000
  • $ 400,000
  • $ 600,000
  • $ 1,000,000
    Beds Tap two numbers to select a range
    Any
    1
    2
    3
    4
    5+
    Baths Tap two numbers to select a range
    Any
    1
    2
    3
    4
    5+
  • List
  • Mixed
  • Map
Chester, NY
Map
238 Properties Available

238 Properties Available

The average price in the selected areas has remained stable. Learn more
  • Default
  • Price-High To Low
  • Price-Low To High
  • Newest Listings
  • Beds (Most)
  • Baths (Most)
  • Year Built (Newest)
  • Square Feet (Biggest)
121 Conklingtown RD, Chester, NY 10918
1/50
Open Sun 3PM-5PM

$749,000

4 Beds3 Baths2,599 SqFt

121 Conklingtown RD, Chester, NY 10918

Listed by MS Realty Group USA, Inc

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
3561 Rte 94, Chester, NY 10918
1/50
Open Sun 2PM-4PM

$649,999

3 Beds3 Baths2,902 SqFt

3561 Rte 94, Chester, NY 10918

Listed by Howard Hanna Rand Realty

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
58 Nancy LN, Chester, NY 10918
1/49
Open Sun 11AM-1PM

$749,999

3 Beds3 Baths2,718 SqFt

58 Nancy LN, Chester, NY 10918

Listed by Howard Hanna Rand Realty

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
260 Gibson Hill RD, Chester, NY 10918
1/22
New

$374,900

3 Beds2 Baths1,644 SqFt

260 Gibson Hill RD, Chester, NY 10918

Listed by Keller Williams Realty

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
69 Cedar Pond LN, Chester, NY 10918
1/50
New

$1,685,000

6 Beds8 Baths7,034 SqFt

69 Cedar Pond LN, Chester, NY 10918

Listed by Prominent Properties Sotheby's

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
429 Franklin ST, Port Chester, NY 10573
1/17
New

$959,000

4 Beds2 Baths5,762 Sqft Lot

429 Franklin ST, Port Chester, NY 10573

Listed by Rye Port Real Estate, Inc.

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
2921 Whispering HLS, Chester, NY 10918
1/42
New

$374,900

3 Beds3 Baths1,331 SqFt

2921 Whispering HLS, Chester, NY 10918

Listed by ARC Realty 1 in Sales

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
12 Perry AVE, Port Chester, NY 10573
1/30
New

$675,000

3 Beds2 Baths1,352 SqFt

12 Perry AVE, Port Chester, NY 10573

Listed by Houlihan Lawrence Inc.

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
50 Hambletonian AVE, Chester, NY 10918
1/45
New

$550,000

3 Beds2 Baths1,583 SqFt

50 Hambletonian AVE, Chester, NY 10918

Listed by Howard Hanna Rand Realty

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
8 Bolton PL, Port Chester, NY 10573
1/18
Coming Soon

$1,100,000

5 Beds5 Baths4,228 SqFt

8 Bolton PL, Port Chester, NY 10573

Listed by Compass Greater NY, LLC

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
1005 Whispering HLS, Chester, NY 10918
1/28
New

$290,000

2 Beds2 Baths1,053 SqFt

1005 Whispering HLS, Chester, NY 10918

Listed by Century 21 Full Service Realty

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
511 Locust AVE, Port Chester, NY 10573
1/7
New

$4,250

3 Beds2 Baths1,000 SqFt

511 Locust AVE, Port Chester, NY 10573

Listed by At Home With Yara Realty

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
2124 Whispering HLS, Chester, NY 10918
1/18
New

$299,000

2 Beds1 Bath1,084 SqFt

2124 Whispering HLS, Chester, NY 10918

Listed by Howard Hanna Rand Realty

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
4704 Whispering HLS, Chester, NY 10918
1/19
Coming Soon

$380,000

3 Beds3 Baths1,331 SqFt

4704 Whispering HLS, Chester, NY 10918

Listed by Sahagian Realty LLC

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
65 Oxford Springs RD, Chester, NY 10918
1/38
Active

$699,000

5 Beds4 Baths3,463 SqFt

65 Oxford Springs RD, Chester, NY 10918

Listed by HomeSmart Homes & Estates

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
173 Creamery Pond RD, Chester, NY 10918
1/48
Active

$699,000

3 Beds3 Baths2,533 SqFt

173 Creamery Pond RD, Chester, NY 10918

Listed by Keller Williams Realty

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
1 Sanford AVE, Chester, NY 10918
1/30
Active
3D

$750,000

4 Beds3 Baths2,280 SqFt

1 Sanford AVE, Chester, NY 10918

Listed by Redfin Real Estate

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
3409 Whispering HLS, Chester, NY 10918
1/24
Coming Soon

$360,000

3 Beds3 Baths1,331 SqFt

3409 Whispering HLS, Chester, NY 10918

Listed by Howard Hanna Rand Realty

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
32 Surrey RD, Chester, NY 10918
1/39
Price Dropped by $14K

$475,000

4 Beds2 Baths1,820 SqFt

32 Surrey RD, Chester, NY 10918

Listed by eXp Realty

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
34 Boville CT, Chester, NY 10918
1/46
Active

$839,000

4 Beds4 Baths2,707 SqFt

34 Boville CT, Chester, NY 10918

Listed by Keller Williams Valley Realty

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
377 Westchester AVE #4F, Port Chester, NY 10573
1/18
Active

$182,500

1 Bed1 Bath800 SqFt

377 Westchester AVE #4F, Port Chester, NY 10573

Listed by Julia B Fee Sothebys Int. Rlty

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
13 Bianca BLVD, Chester, NY 10918
1/49
Active

$700,000

4 Beds3 Baths3,296 SqFt

13 Bianca BLVD, Chester, NY 10918

Listed by Keller Williams Realty

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
36 Pilgrim DR, Port Chester, NY 10573
1/33
Active

$749,999

4 Beds2 Baths1,668 SqFt

36 Pilgrim DR, Port Chester, NY 10573

Listed by Keller Williams NY Realty

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
1 Landmark SQ #115, Port Chester, NY 10573
1/16
Active

$2,700

1 Bed1 Bath881 SqFt

1 Landmark SQ #115, Port Chester, NY 10573

Listed by Christie's Int. Real Estate

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
  • 1
  • 2
  • 3
  • 4
  • 5
  • ...
  • 10
      Home
      Search
      Buy
      1. Affordability Calculator
      2. Featured Listings
      Sell
      1. Home
      2. Sell My Home
      3. Market Snapshot
      Home Valuation
      About
      1. About Us
      2. Reviews
      3. Preferred Vendors
      Contact Us
HomeSmart Homes and Estates

Michael & Tara Holmes License ID: 10401274851

+1(914) 774-5684 mikeholmesrealestate@gmail.com

777 Westchester Ave, White Plains, NY 10604, USA

Fair Housing Notice: Federal, State and Local Fair Housing Laws protect individuals from housing discrimination. It is unlawful to discriminate based on certain protected characteristics, which include, but are not limited to: race, creed, color, national origin, sexual orientation, gender identity or expression, military status, sex, age, disability, marital status, lawful source of income or familial status. Click here to read more. Click here to view the New York Standardized Operating Proced

Get My App

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.
      Home
      Search
      Buy
      1. Affordability Calculator
      2. Featured Listings
      Sell
      1. Home
      2. Sell My Home
      3. Market Snapshot
      Home Valuation
      About
      1. About Us
      2. Reviews
      3. Preferred Vendors
      Contact Us
HomeSmart Homes and Estates

Michael & Tara Holmes License ID: 10401274851

+1(914) 774-5684 mikeholmesrealestate@gmail.com

777 Westchester Ave, White Plains, NY 10604, USA

Fair Housing Notice: Federal, State and Local Fair Housing Laws protect individuals from housing discrimination. It is unlawful to discriminate based on certain protected characteristics, which include, but are not limited to: race, creed, color, national origin, sexual orientation, gender identity or expression, military status, sex, age, disability, marital status, lawful source of income or familial status. Click here to read more. Click here to view the New York Standardized Operating Proced

Get My App

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.