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Explore Similar Homes Within 10 Miles of 21628, MD

  • 105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    /48

    $1,395,500 Open Sat 11AM - 1PM

    • 5 Beds
    • 4.5 Baths
    • 3,243 Sq Ft

    105 High St, Chestertown, MD 21620

    Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • 112 Elm St, Chestertown, MD 21620
    112 Elm St, Chestertown, MD 21620
    112 Elm St, Chestertown, MD 21620
    /19

    $269,900 Open Sat 11AM - 1PM

    • 3 Beds
    • 1 Bath
    • 1,356 Sq Ft

    112 Elm St, Chestertown, MD 21620

    Sought after location in College Heights. Short walk to downtown Chestertown and Parks. This cozy rancher is a diamond in the rough and is ready for new owners! located on a safe and quiet street, with public water and sewer with municipal pickups. Don't miss your opportunity to live in a great location! Being sold as is and priced accordingly.

    Brian Whitaker Coldwell Banker Waterman Realty

    112 Elm St, Chestertown, MD 21620
  • 118 Little Harbor Way Unit 202, Chestertown, MD 21620
    118 Little Harbor Way Unit 202, Chestertown, MD 21620
    118 Little Harbor Way Unit 202, Chestertown, MD 21620
    /56

    $675,000 Open House 4/04

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    118 Little Harbor Way Unit 202, Chestertown, MD 21620

    Welcome to 118 Little Harbor Way #202, a beautifully reimagined waterfront condo offering effortless living and sweeping panoramic views of the Chester River. Located in the highly desirable Chester River Landing community, this second-floor, 3-bedroom, 2-bath residence delivers the perfect blend of modern luxury, low maintenance, and classic Eastern Shore charm. Completely taken down to the

    Kaitlyn Collins Benson & Mangold, LLC

    118 Little Harbor Way Unit 202, Chestertown, MD 21620
  • 101 Coleman Dr, Chestertown, MD 21620
    101 Coleman Dr, Chestertown, MD 21620
    101 Coleman Dr, Chestertown, MD 21620
    /56

    $524,900 Open Sat 12PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 2,268 Sq Ft

    101 Coleman Dr, Chestertown, MD 21620

    Tucked away just south of the scenic Chester River and moments from the timeless charm of Chestertown, this inviting home offers a warm and welcoming retreat in the heart of Queen Anne’s County. Surrounded by the natural beauty of Maryland’s Eastern Shore, the setting feels peaceful and relaxed—where quiet mornings and golden sunsets become part of everyday life.Inside, the home is designed

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    101 Coleman Dr, Chestertown, MD 21620
  • 118 Dabbling Ct, Church Hill, MD 21623
    118 Dabbling Ct, Church Hill, MD 21623
    118 Dabbling Ct, Church Hill, MD 21623
    /76

    $760,000 Open Sat 12PM - 2PM

    • 6 Beds
    • 4 Baths
    • 5,277 Sq Ft

    118 Dabbling Ct, Church Hill, MD 21623

    Stunning, custom built beauty boasting over 5,200 SF of customized three-level living on 1.27 private acres at the end of a cul-de-sac, offering space, flexibility, and thoughtful design throughout.This newly listed 6-bedroom, 5-bath home features an airy, open floor-plan with a dramatic two-story foyer, formal dining room, private office, and main-level bedroom with full bath. The spacious

    Jennifer Chaney Chaney Homes, LLC

    118 Dabbling Ct, Church Hill, MD 21623
  • 106 S Queen St, Chestertown, MD 21620
    106 S Queen St, Chestertown, MD 21620
    106 S Queen St, Chestertown, MD 21620
    /70

    $865,000 Open House 4/03

    • 3 Beds
    • 3.5 Baths
    • 2,472 Sq Ft

    106 S Queen St, Chestertown, MD 21620

    *Open House Friday April 3rd 5-7pm and Saturday April 4th 10am-12pm *The Bedingfield Hands House, circa 1750, traces its routes back to pre-revolutionary times and has a story to tell. One of the few downtown homes to offer a large front courtyard, the property features beautifully landscaped gardens and a mature magnolia tree creating a private and welcoming outdoor retreat. Offering

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    106 S Queen St, Chestertown, MD 21620
  • 481 Eagle Manor Dr, Church Hill, MD 21623
    481 Eagle Manor Dr, Church Hill, MD 21623
    481 Eagle Manor Dr, Church Hill, MD 21623
    /50

    $775,000 Open Sun 11AM - 1PM

    • 3 Beds
    • 2.5 Baths
    • 2,658 Sq Ft

    481 Eagle Manor Dr, Church Hill, MD 21623

    No need to wait for new construction when this beauty is ready to WOW you! From the moment you step inside your attention will be drawn to all the little details that make this property a show stopper... Wood beams on the soaring ceilings, huge center kitchen island with storage on both sides, gorgeous engineered flooring, screened porch built on a cement foundation not decking, shadow box detail

    Tricia Wilson Wilson Realty & Staging LLC

    481 Eagle Manor Dr, Church Hill, MD 21623
  • 196 Birchwood Ln, Galena, MD 21635
    196 Birchwood Ln, Galena, MD 21635
    196 Birchwood Ln, Galena, MD 21635
    /26

    $365,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,691 Sq Ft

    196 Birchwood Ln, Galena, MD 21635

    Welcome to this beautifully updated ranch-style home in the quiet Dogwood Village community, offering the ease of one-level living with modern upgrades throughout. Step inside to a bright, open layout with tall ceilings, spacious rooms, and durable luxury vinyl plank flooring. The newly remodeled kitchen is the heart of the home, perfect for everyday living and entertaining, while the newly

    Grace Casella Crown Homes Real Estate

    196 Birchwood Ln, Galena, MD 21635
  • 11944 Augustine Herman Hwy, Kennedyville, MD 21645
    11944 Augustine Herman Hwy, Kennedyville, MD 21645
    11944 Augustine Herman Hwy, Kennedyville, MD 21645
    /21

    $480,000 Open House 4/04

    • 4 Beds
    • 2 Baths
    • 2,156 Sq Ft

    11944 Augustine Herman Hwy, Kennedyville, MD 21645

    Step into timeless charm with modern updates in this beautifully renovated early 1900s home located in the heart of Kennedyville. Offering 4 bedrooms, 2 full baths, and a versatile third-floor loft, this home seamlessly blends classic character with today’s conveniences. From the moment you arrive, you’ll be drawn to the inviting wraparound front porch—perfect for relaxing and enjoying small-town

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    11944 Augustine Herman Hwy, Kennedyville, MD 21645
  • 120 Reeand Ln, Church Hill, MD 21623
    120 Reeand Ln, Church Hill, MD 21623
    120 Reeand Ln, Church Hill, MD 21623
    /59

    $443,900 Open Sun 1PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 1,608 Sq Ft

    120 Reeand Ln, Church Hill, MD 21623

    Discover Your Private Pool Oasis in Church Hill’s Charming No-HOA Community!Welcome to 120 Reeand Lane — a turn-key 2018 Craftsman gem in the quiet, friendly neighborhood of The Meadows. This 3-bedroom, 2.5-bath home delivers 1,608 sq ft of bright, modern living on a spacious 0.24-acre lot. Priced at $443,900 and move-in ready with fresh neutral paint and brand-new carpet upstairs, it’s the

    Heather Dolan Chesapeake Real Estate Associates, LLC

    120 Reeand Ln, Church Hill, MD 21623
Maryland Queen Annes County Crumpton 21628

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