New Luxury Home Communities in Chestertown

The Chestertown, MD area is a great place to buy a luxury home. With over 7 builders across 9 communities you’ll find a great selection of high-end homes in communities with upscale amenities.

In your new luxury home you will enjoy fine architectural details as well as thoughtful interior design and high quality products and appliances. From hardwood flooring to granite countertops and connectivity to the internet of things, your luxury home will be unique to you. Enjoy the latest in building technologies and eco-friendly appliances to help save you money and keep your home running efficiently for years to come.

Chestertown is a growing market for luxury homes. Whether your budget starts at $424,990 or extends beyond $719,900 there’s an option for you in the high-end market. Luxury homes run the gamut of sizes from 1,670 to 4,988 square feet. Whether your family is large or small, upgrading or downsizing, the luxury market is a great place to begin your search.

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    9 Communities

    Quick Move-In Hot Deals

    Chestertown, MD Communities

    Chester River Landing by Covell Communities

    Chester River Landing by Covell Communities in Eastern Shore Maryland
    homes in Chester River Landing by Covell Communities
    Covell Communities in Chestertown, MD

    From $479,900 - $614,900

    100 Landing Lane
    Chestertown, MD 21620

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    Builder Community
    3 homes match your search

    Nearby Communities

    Shaw's Discovery Townhomes by Ryan Homes

    Shaw's Discovery Townhomes by Ryan Homes in Baltimore Maryland

    Coming Soon

    homes in Shaw's Discovery Townhomes by Ryan Homes
    Ryan Homes in Sparrows Point, MD

    2821 Shaws Road
    Sparrows Point, MD 21219

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    Builder Community

    Beech Creek - Villas by Lennar

    Beech Creek - Villas by Lennar in Baltimore Maryland

    Coming Soon

    homes in Beech Creek - Villas by Lennar
    Lennar in Aberdeen, MD

    810 Classic Drive
    Aberdeen, MD 21001

    Map

    Builder Community

    Gibson's Grant by Koch Homes

    Gibson's Grant by Koch Homes in Eastern Shore Maryland
    homes in Gibson's Grant by Koch Homes
    Koch Homes in Chester, MD

    From $471,900 - $603,900

    110 John Gibson Dr
    Chester, MD 21619

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    Builder Community
    8 homes match your search

    19.4 Miles Away

    K. Hovnanian’s® Four Seasons at Kent Island by K. Hovnanian's® Four Seasons

    K. Hovnanian’s® Four Seasons at Kent Island by K. Hovnanian's® Four Seasons in Eastern Shore Maryland

    Grand Opening

    homes in K. Hovnanian’s® Four Seasons at Kent Island by K. Hovnanian's® Four Seasons
    K. Hovnanian's® Four Seasons in Chester, MD

    From $424,990 - $584,990

    203 Bayberry Drive
    Chester, MD 21619

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    Active Adult Community
    8 homes match your search

    19.7 Miles Away

    Greenleigh by Williamsburg Homes LLC

    Greenleigh by Williamsburg Homes LLC in Baltimore Maryland

    Grand Opening

    homes in Greenleigh by Williamsburg Homes LLC
    Williamsburg Homes LLC in Middle River, MD

    From $474,900 - $719,900

    505 Heritage Street
    Middle River, MD 21220

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    Builder Community
    5 homes match your search

    20.6 Miles Away

    Gibson's Grant by Covell Communities

    Gibson's Grant by Covell Communities in Eastern Shore Maryland
    homes in Gibson's Grant by Covell Communities
    Covell Communities in Chester, MD

    From $489,900 - $649,900


    Chester, MD 21619

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    Builder Community
    19 homes match your search

    21.2 Miles Away

    Laurel Ridge - The Glen by Toll Brothers

    Laurel Ridge - The Glen by Toll Brothers in Baltimore Maryland
    homes in Laurel Ridge - The Glen by Toll Brothers
    Toll Brothers in Abingdon, MD

    From $499,995 - $599,995

    703 Dowers Road
    Abingdon, MD 21009

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    Builder Community
    1 home matches your search

    • Deal
    • Green

    22.7 Miles Away

    The Estates At St. Anne's by Ryan Homes

    The Estates At St. Anne's by Ryan Homes in Wilmington-Newark Delaware

    Close Out

    homes in The Estates At St. Anne's by Ryan Homes
    Ryan Homes in Middletown, DE

    From $429,990 - $489,990

    307 Galloway Street
    Middletown, DE 19709

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    Builder Community
    3 homes match your search

    23.1 Miles Away

    Popular Searches Near Chestertown, MD

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