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    Chester Real Estate Search

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    Chester Homes for Sale

    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. 

    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 the Chester real estate market? Sign up for a Chester Real Estate Market Report to see what’s active, under contract, and sold!

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

    Newest Chester Homes and Condos for Sale

    2654 Palm   Drive, Chester image
    2654 Palm Drive, Chester $369,900 ▼

    Open House Saturday, 2/27 from 11am-1pm. Harbor View Rancher on Kent Island - Welcoming Front Porch. Living Room with Cozy Wood Fireplace. Hardwood Floors throughout! ...

    • 3 Beds
    • 2 Baths
    Courtesy of Rosendale Realty

    Listing courtesy of Rosendale Realty.

    1830 Sherman   Drive, Chester image
    1830 Sherman Drive, Chester — Harborview Kent Island $349,900

    Wonderfully maintained Rambler with an in law suite! Boasting 2,176 Sq. Ft. of living space on .27 Acre on Kent Island! Featuring a new kitchen with luxury vinyl floors...

    • 4 Beds
    • 3 Baths
    Courtesy of Rosendale Realty

    Listing courtesy of Rosendale Realty.

    226 Bentons Pleasure   Road, Chester image
    226 Bentons Pleasure Road, Chester $895,000

    FORGET DAYS ON MARKET THIS HOME IS READY TO GO-- NOW VACANT -- FRESHLY PAINTED THE PLEASING GRAY TONE -- NEW CARPET-- BEAUTIFUL! PLEASE CHECK OUT NEW PHOTOS AND VIRTUAL ...

    • 4 Beds
    • 3 Baths
    Courtesy of Cummings & Co. Realtors

    Listing courtesy of Cummings & Co. Realtors.

    1908 Harbor   Drive, Chester image
    1908 Harbor Drive, Chester $315,000

    Exceptionally cozy and well-maintained one-level living home, with lots of upgrades, awaits its lucky new owners! Crown molding, tilt-in easy-clean windows, the newest lo...

    • 2 Beds
    • 2 Baths
    Courtesy of Long & Foster Real Estate, Inc.

    Listing courtesy of Long & Foster Real Estate, Inc..

    3000 Heron's Nest   Way Unit #24, Chester image
    3000 Heron's Nest Way Unit #24, Chester $539,900 ▼

    * Home is availble to move in March 2021. Call today to find out the details and start living the life you want. Welcome to a new active adult 55+ community on Maryland'...

    • 3 Beds
    • 3 Baths
    Courtesy of Long & Foster Real Estate, Inc.

    Listing courtesy of Long & Foster Real Estate, Inc..

    101 Swan Cove   Lane Unit #101, Chester image
    101 Swan Cove Lane Unit #101, Chester $749,000 ▼

    BIG PRICE DROP 25k . GREAT TIME TO OWN THIS WATER FRONT CONDO ! WATERFRONT LIVING IN LUXURY ! Absolutely the best location !!!! This 4 bedroom 3.5 bath 3300 + square fee...

    • 4 Beds
    • 4 Baths
    Courtesy of Redfin Corp

    Listing courtesy of Redfin Corp.

    3000 Heron's Nest   Way Unit #11, Chester image
    3000 Heron's Nest Way Unit #11, Chester $443,900 ▲

    Call today to find out the details and start living the life you want. Welcome to a new active adult 55+ community on Maryland's Chesapeake Bay, offering island-living w...

    • 2 Beds
    • 3 Baths
    Courtesy of Long & Foster Real Estate, Inc.

    Listing courtesy of Long & Foster Real Estate, Inc..

    3000 Heron's Nest   Way Unit #42, Chester image
    3000 Heron's Nest Way Unit #42, Chester $499,900 ▼

    Welcome to a new active adult 55+ community on Maryland's Chesapeake Bay, offering island-living with new single-family homes and condominiums. Discover an amenity-filled...

    • 2 Beds
    • 3 Baths
    Courtesy of Long & Foster Real Estate, Inc.

    Listing courtesy of Long & Foster Real Estate, Inc..

    3000 Heron's Nest   Way Unit #23, Chester image
    3000 Heron's Nest Way Unit #23, Chester $457,900

    Welcome to a new active adult 55+ community on Maryland's Chesapeake Bay, offering island-living with new single-family homes and condominiums. Discover an amenity-filled...

    • 2 Beds
    • 3 Baths
    Courtesy of Long & Foster Real Estate, Inc.

    Listing courtesy of Long & Foster Real Estate, Inc..

    312 Bayberry   Drive, Chester image
    312 Bayberry Drive, Chester $468,990 ▲

    Welcome a new active adult 55+ community on Maryland's Chesapeake Bay, offering island-living with new single-family homes and condominiums. Discover an amenity-filled, ...

    • 2 Beds
    • 2 Baths
    Courtesy of Long & Foster Real Estate, Inc.

    Listing courtesy of Long & Foster Real Estate, Inc..

    147 Bluebell   Court, Chester image
    147 Bluebell Court, Chester $439,990 ▲

    Welcome a new active adult 55+ community on Maryland's Chesapeake Bay, offering island-living with new single-family homes and condominiums. Discover an amenity-filled, ...

    • 2 Beds
    • 2 Baths
    Courtesy of Long & Foster Real Estate, Inc.

    Listing courtesy of Long & Foster Real Estate, Inc..

    316 Bayberry   Drive, Chester image
    316 Bayberry Drive, Chester $558,990 ▲

    Welcome a new active adult 55+ community on Maryland's Chesapeake Bay, offering island-living with new single-family homes and condominiums. Discover an amenity-filled, r...

    • 2 Beds
    • 2 Baths
    Courtesy of Long & Foster Real Estate, Inc.

    Listing courtesy of Long & Foster Real Estate, Inc..

    302 Bayberry   Drive, Chester image
    302 Bayberry Drive, Chester $476,990 ▲

    Welcome a new active adult 55+ community on Maryland's Chesapeake Bay, offering island-living with new single-family homes and condominiums. Discover an amenity-filled, r...

    • 2 Beds
    • 3 Baths
    Courtesy of Long & Foster Real Estate, Inc.

    Listing courtesy of Long & Foster Real Estate, Inc..

    0000 Mchenny Court, Chester image
    0000 Mchenny Court, Chester $856,990 ▼

    Do not miss out on building a Kingston 3 story in Gibson's Grant . 4 bedrooms, 3. full 1 half baths, 10 foot first floor ceilings, 2 car garage. 2nd floor loft/tv area....

    • 4 Beds
    • 4 Baths
    Courtesy of Koch Realty, Inc.

    Listing courtesy of Koch Realty, Inc..

    0000 Mchenny Court, Chester image
    0000 Mchenny Court, Chester $803,990 ▼

    Do not miss out on building a Kingston 2 story in Gibson's Grant . 4 bedrooms, 3. full baths, 10 foot first floor ceilings, 2 car garage. 2nd floor loft/tv area. Do not...

    • 4 Beds
    • 3 Baths
    Courtesy of Koch Realty, Inc.

    Listing courtesy of Koch Realty, Inc..

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