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    Chester Real Estate Search

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    Search All Chester NY Real Estate

    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

    1390 Kings  Highway, Sugar Loaf image
    1390 Kings Highway, Sugar Loaf $319,000

    This property in the hamlet of Sugar Loaf is considered a multi family dwelling because of the additional living space offered in the trailer home on the property. The ma...

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    • 3 Beds
    • 2 Baths
    • H6109593 MLS
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    57 Ridgefield  Drive, Chester image
    57 Ridgefield Drive, Chester $615,000

    Chester, Ny. Hurry to see this Like New, 4 bedroom 2.5 Bath Colonial in Ashford Estates. This home features paver walk way, rocking chair front porch, stone front, 2 sto...

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    • 4 Beds
    • 3 Baths
    • H6106585 MLS
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    59 Southside  Drive, Monroe image
    59 Southside Drive, Monroe $274,500

    Cute as a button!! Updated Ranch in Monroe with desirable Monroe/Woodbury Schools! The newly updated kitchen offers granite countertops and stainless steel appliances! Th...

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    • 2 Beds
    • 1 Baths
    • H6105145 MLS
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    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 w...

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    • H6107467 MLS
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    209 Glenmore  Road, Chester image
    209 Glenmore Road, Chester $439,000

    Spacious rooms in a quiet setting with full privacy from neighbors. Two lots included with a horse barn. Perfect for large families with children, or vacation home. Prope...

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    • 5 Beds
    • 3 Baths
    • 3301843 MLS
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    3 Twin Brooks  Drive, Chester image
    3 Twin Brooks Drive, Chester $549,999

    This is not your Cookie Cutter Colonial.Offers a Surprise at every turn.custom cabinets in dining room.Fantastic kitchen with room all.Formal living room with a brick woo...

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    • 4 Beds
    • 3 Baths
    • H6097109 MLS
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    40 Lincoln  Road, Monroe image
    40 Lincoln Road, Monroe $420,000

    Welcome to Lakehill Farms! This spacious bilevel with a brand new roof features an eat in kitchen with stainless steel appliances, open concept living and dining area. Yo...

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    • 4 Beds
    • 2 Baths
    • H6104897 MLS
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    32 Surrey  Road, Chester image
    32 Surrey Road, Chester $350,000

    Newly renovated raised ranch on a quiet road in the town of Chester, close to schools, shopping, parks, medical facilities and restaurants. Easy highway access as well as...

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    • 4 Beds
    • 2 Baths
    • H6104430 MLS
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    25 Natures  Trail, Chester image
    25 Natures Trail, Chester $925,000

    This beautifully custom contemporary is ready for you! The home boasts 18 ft. vaulted ceilings, a custom gourmet kitchen, an open concept kitchen, dining room, and livin...

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    • 4 Beds
    • 3 Baths
    • H6105033 MLS
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    7 Murray  Drive, Chester image
    7 Murray Drive, Chester $435,000

    There is nothing typical about this bi-level in the sought after Monroe-Woodbury School District. Bring your creative eye to transform this large house into the home of y...

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    • 4 Beds
    • 3 Baths
    • H6101085 MLS
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    412 Laroe  Road, Chester image
    412 Laroe Road, Chester $375,000

    This beautiful ranch is waiting to become your next home sweet home! Spacious living room with vaulted ceiling brings tons of natural light through large beautiful window...

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    • 3 Beds
    • 2 Baths
    • H6104902 MLS
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    54 Southside  Drive, Monroe image
    54 Southside Drive, Monroe $409,000 ▼

    This upgraded renovated home contains spacious rooms, Brand new magnificent kitchen with quartz countertops, High-end appliances,master bedroom with Beth on first floo...

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    • 4 Beds
    • 3 Baths
    • H6103812 MLS
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    255 Heritage  Lane, Monroe image
    255 Heritage Lane, Monroe $285,000

    Welcome to Windridge. This 3 bedroom, 2.5 bath townhome is your answer to no hassle, carefree Hudson Valley living. Well maintained and move in ready. The first floor bo...

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    • 3 Beds
    • 3 Baths
    • H6103245 MLS
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    63 Surrey  Road, Chester image
    63 Surrey Road, Chester $349,900

    Come make this great home in one of Chester?s most sought after subdivisions yours today! This 3 bedroom ranch has everything you are looking for and much more. This home...

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    • 3 Beds
    • 2 Baths
    • H6100834 MLS
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    1108 Kings  Highway, Chester image
    1108 Kings Highway, Chester $1,300,000

    Located on Kings Highway between Chester and Warwick, this beautiful stone and stucco building is just minutes from Routes 17 and 17M. Newer 2 story elevator building bro...

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    • H6101209 MLS
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    74 Overlook  Trail, Sugar Loaf image
    74 Overlook Trail, Sugar Loaf $699,900

    SITUATED IN THE HAMLET OF SUGAR LOAF MINUTES TO THE CRAFT VILLAGE; PANORAMIC VIEWS FROM ANY OF THE FRONT WINDOWS. THIS 4265 SQUARE FT MAJESTIC HOME SITS ON 5.2 ACRES, KIT...

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    • 4 Beds
    • 3 Baths
    • H6100522 MLS
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    45 Conklingtown  Road, Chester image
    45 Conklingtown Road, Chester $1,200,000

    A magnificent?Move-in ready single-family home, located in one of the most desirable and exclusive areas of Chester N.Y. Elegant design with extra attention to quality, r...

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    • 5 Beds
    • 4 Baths
    • H6095387 MLS
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    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...

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    • 2 Beds
    • 1 Baths
    • H6087315 MLS
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    117 Murray  Drive, Chester image
    117 Murray Drive, Chester $699,000 ▼

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

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    • 4 Beds
    • 3 Baths
    • H6075261 MLS
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    1048 Lakes  Road, Monroe image
    1048 Lakes Road, Monroe $472,000

    FULLY AVAILABLE...........**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 GA...

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    • 5 Beds
    • 2 Baths
    • H6075231 MLS
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    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...

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    • 4 Beds
    • 2 Baths
    • H6068150 MLS
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    1253 Kings  Highway, Chester image
    1253 Kings 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...

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    • H6062557 MLS
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    12 Silvertail  Road, Chester image
    12 Silvertail Road, Chester $209,000 ▼

    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...

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    • H6062960 MLS
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    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...

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    • H6059118 MLS
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    County Hwy 13, Chester image
    County Hwy 13, Chester $486,000 ▲

    2.7 acres lot overlooking Chester Industrial Park, Perfect spot ideal for Warehousing. Tax records show the property as Co Hwy 13, but the property is located at the cul-...

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    • H6049335 MLS
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    282 Laroe  Road, Chester image
    282 Laroe Road, Chester $3,450,000 ▼

    329+ Glorious Acres, comprising a major portion of Sugarloaf Mountain, within an hour's drive of Manhattan! 282 Laroe Road (parcel 7-35-1) is one of 5 contiguous lots on...

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    • 6 Beds
    • 5 Baths
    • H6046522 MLS
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    Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals. Copyright 2021 OneKey All rights reserved.

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