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Chester Real Estate Search

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Our website features the best Chester real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

Chester, NY. 

The town of Chester is located directly off of Rt. 17. Chester gives commuters the perfect opportunity for a short drive to the city, and a home in an area with a suburban feel. In the town of Chester shopping center you'll find a ShopRite, Elite Cinema 6 movie theater, Colonial Lanes bowling ally, and Tractor Supply, to name a few. There are several smaller stores such as Payless, and a few fast food restaurants including Taco Bell. A unique staple of Chester is The Castle Fun Center. This kid-friendly venue provides an array of activities for all ages. Roller skating, mini golf, laser tag, and go karts can all be enjoyed here.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

Chester Homes for Sale

92 Restdale  Road, Chester image
92 Restdale Road, Chester $499,000

This well maintained home has everything you have been looking for. As you approach your new home you will greeted by the rocking chair front porch and serene privacy. On...

  • 4 Beds
  • 3 Baths
  • H6092335 MLS
155 Eagleton  Drive, Monroe image
155 Eagleton Drive, Monroe $260,000

Welcome to 155 Eagleton Drive located in the desirable Windridge Estates. This well maintained Townhome style 3 bedroom unit boasts newer heating/AC systems and 2 year yo...

  • 3 Beds
  • 2 Baths
  • H6090713 MLS
486 Meri  Lane, Monroe image
486 Meri Lane, Monroe $325,000

Windridge Townhomes benefits from a clubhouse, with a pool, tennis and basketball courts and a children's play area, as well as, the opportunity for fishing and paddling...

  • 3 Beds
  • 3 Baths
  • H6091331 MLS
237 Meadow  Avenue, Chester image
237 Meadow Avenue, Chester $239,999

Accepted Offer. No more showings at this time. Cozy 2 bedroom home with plenty of front and backyard space. Features privacy and expansive views. Convenient access to all...

  • 2 Beds
  • 1 Baths
  • H6087315 MLS
117 Murray  Drive, Chester image
117 Murray Drive, Chester $749,000

Exquisite Contemporary Home sited with complete privacy on just under four acres. Wonderful drive up with 950 ft driveway. Expansive custom built home offers an extensive...

  • 3 Beds
  • 3 Baths
  • H6075261 MLS
901 Swan Hollow  Road, Monroe image
901 Swan Hollow Road, Monroe $224,900

WINDRIDGE!! IMMACULATE END UNIT! LOW TAXES! 3 Bedrooms! 2 1/2 Bathrooms! Brand New Kitchen with Stainless Steel Appliances! Renovated Bathrooms! Master Bedroom Suite! Liv...

  • 3 Beds
  • 3 Baths
  • H6086905 MLS
361 Heritage  Lane, Monroe image
361 Heritage Lane, Monroe $265,000

Remarkable end unit in Windridge offering an easy carefree life style with all the amenities one could hope for. 2 inground pools, 2 tennis courts a basketball court and ...

  • 3 Beds
  • 3 Baths
  • H6086575 MLS
15 Mountainside  Drive, Chester image
15 Mountainside Drive, Chester $479,900

Grand Opening of Ridgeview Estates in Town of Chester and Chester Schools. This new community comprises 8 to be built homes. Choose your homesite and your floorplan and...

  • 4 Beds
  • 3 Baths
  • H6085494 MLS
Straub  Lane, Chester image
Straub Lane, Chester $399,900

36.5 Amazing Acres In The Beautiful Town Of Chester! 2 Lots Included! The First Lot Is 35 Acres With Access Off 2 Roads. Directly Off Beautiful Cul De Sac Straub Lane Wit...

  • H6084996 MLS
276 Black Meadow  Road, Chester image
276 Black Meadow Road, Chester $495,000

Minutes from bus station & I-17 & 10 min. to the train, this home is a commuter s dream! Located in the award-winning Warwick school district, this 4-bedroom 3-bath c...

  • 4 Beds
  • 3 Baths
  • H6084388 MLS
7 Conklingtown  Road, Chester image
7 Conklingtown Road, Chester $249,000 ▼

Adorable Ranch with large flat 1/2 Acre yard, close to shopping, bus and highway. All new stainless appliances, Cathedral kitchen w granite tops. Large full basement with...

  • 2 Beds
  • 1 Baths
  • H6072522 MLS
28 Midway  Drive, Monroe image
28 Midway Drive, Monroe $390,000 ▼

MONROE SCHOOLS! Welcome Home! A wrapping rustic staircase is complemented by an accent window wall spanning two stories, creating a pathway for natural light to stream in...

  • 3 Beds
  • 2 Baths
  • H6077121 MLS
32 Mountainside  Drive, Chester image
32 Mountainside Drive, Chester $539,900

Grand Opening of Ridgeview Estates in Town of Chester and Chester Schools. This new community comprises 8 to be built homes. Choose your homesite and your floorplan and...

  • 4 Beds
  • 3 Baths
  • H6078256 MLS
36 Mountainside  Drive, Chester image
36 Mountainside Drive, Chester $514,900

Grand Opening of Ridgeview Estates in Town of Chester and Chester Schools. This new community comprises 8 to be built homes. Choose your homesite and your floorplan and...

  • 4 Beds
  • 3 Baths
  • H6078157 MLS
1048 Lakes  Road, Monroe image
1048 Lakes Road, Monroe $472,000

**CIRCA 1784 AND BEAUTIFULLY REDONE COLONIAL ON 1.50 GORGEOUS ACRES**5 BDRMS 2 BATHS*LIV.RM*FORMAL DIN.ROOM*FAMILY RM*REC.ROOM WITH WET BAR*2 GAS BRICK FPLS - 1 OUTDOOR ...

  • 5 Beds
  • 2 Baths
  • H6075231 MLS
8 Kennedy  Lane, Monroe image
8 Kennedy Lane, Monroe $349,000

Cape Cod located on a Private Road with Monroe Schools. Walk in to a handy mud room for all you outdoor clothing and shoes. Entertain in the dining room right off the kit...

  • 4 Beds
  • 2 Baths
  • H6068150 MLS
111 Lake Region  Boulevard, Monroe image
111 Lake Region Boulevard, Monroe $199,500 ▼

THIS PROPERTY IS A HANDYMAN'S SPECIAL WITH ENDLESS POSSIBILITIES AND ROOM FOR EXPANSION! This quaint 2 bedroom, 1 bath Ranch sits on a beautiful level double lot. Enjoy f...

  • 2 Beds
  • 1 Baths
  • H6067012 MLS
18 Natures  Trail, Chester image
18 Natures Trail, Chester $499,000 ▼

Look no further for privacy at its finest perfectly nestled in the beauty & splendor of the Hudson Valley. A private road leads you to a meticulously & lovingly cared fo...

  • 3 Beds
  • 3 Baths
  • H6066206 MLS
1253 Kings Hwy  Highway, Chester image
1253 Kings Hwy Highway, Chester $1,500,000

100 Beautiful Acres In Chester Awaits Your Imagination! Amazing Investment Opportunity! An Hour Into The Heart Of Manhattan! Close Enough To Enjoy All Of The Culture, T...

  • H6062557 MLS
35 Banker  Drive, Chester image
35 Banker Drive, Chester $399,000

An Equestrians dream, the site where the famous horse, Hambletonian, was foaled! Imagine owning this incredible 32 acres of land and the endless possibilities that come ...

  • H6063729 MLS
12 Silvertail  Road, Chester image
12 Silvertail Road, Chester $229,000 ▼

Views, views, views! Seize the opportunity to own one of the last remaining lots available in the prestigious Hambleton Hills subdivision. Build your dream home on this s...

  • H6062960 MLS
25 Natures  Trail, Chester image
25 Natures Trail, Chester $925,000

This Grand Contemporary Home Is Everything You Need For A Luxurious Life, Featuring 8Ft Mahogany Doors, Solid Cherry Cabinets Through Out Kitchen, Blue Stone Patios, 10Ft...

  • 4 Beds
  • 3 Baths
  • H6062250 MLS
101 Beverly  Road, Chester image
101 Beverly Road, Chester $319,900

Homepath property for sale! Large colonial tucked away in scenic Chester waiting for your personal touch! Don't wait, come take a look today!

  • 3 Beds
  • 3 Baths
  • H6060047 MLS
7 Black Meadow  Road, Chester image
7 Black Meadow Road, Chester $7,000,000

ATTENTION: ALL Sports Enthusiasts. Perfect situation for nationally recognized training facility operator to expand their base. Established business with consistent wa...

  • H6059118 MLS
158 Rick  Way, Chester image
158 Rick Way, Chester $500,000

Beautiful home! Privacy abounds on this 5.2 acre Paradise!! Imagine your own land where you ride your ATVs and dirt bikes or walk the hiking rails surrounded by mother's ...

  • 4 Beds
  • 3 Baths
  • H6057416 MLS
66 Murray  Drive, Chester image
66 Murray Drive, Chester $369,000

Amazing Home With Great Potential! Large Bedrooms With A Large Basement Which Is A Plus! Has A Beautiful Large Layout For The Living Room, Dining Room, And Kitchen! 5 Bed...

  • 4 Beds
  • 4 Baths
  • H6056137 MLS
840 Laroe  Road, Monroe image
840 Laroe Road, Monroe $240,000

9.1 Acres of flat and sloping land with water access. PLEASE DO NOT ENTER HOUSE-FLOOR UNSTABLE. Please click on thumbnail photos to see other photos. Owner will remove s...

  • H6048877 MLS
282 Laroe  Road, Chester image
282 Laroe Road, Chester $3,450,000 ▼

Unique & Rare Opportunity, within an hour's drive of Manhattan- Graceful 6 BR, 3.2 BTH Colonial Farmhouse Property, complete with 8000+- squ. ft. Antique Barn with 5-car ...

  • 6 Beds
  • 5 Baths
  • H6046522 MLS
1381 Kings  Highway, Chester image
1381 Kings Highway, Chester $350,000

PERFECT INVESTMENT OPPORTUNITY IN CHARMING SUGAR LOAF ! This home boasts bottom floor commercial/retail space, 2nd floor 2 bedroom apartment and studio apartment PLUS an ...

  • H4905115 MLS


The data relating to real estate for sale or lease on this web site comes in part from HGMLS. Real estate listings held by brokerage firms other than Real Estate Company are marked with the HGMLS logo or an abbreviated logo and detailed information about them includes the name of the listing broker. The information appearing herein has not been verified by the Hudson Gateway Multiple Listing Service, Inc. or the Hudson Gateway Association of Realtors, Inc. or by any individual(s) who may be affiliated with said entities, all of whom hereby collectively and severally disclaim any and all responsibility for the accuracy of the information appearing at this web site, at any time or from time to time. All such information should be independently verified by the recipient of such data. This data is not warranted for any purpose. Copyright 2021 Hudson Gateway Multiple Listing Service, Inc. All rights reserved.

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