6,868

Chestertown, MD Homes

Section Image
  • 25740 Collins Ave, Chestertown, MD 21620
    25740 Collins Ave, Chestertown, MD 21620
    25740 Collins Ave, Chestertown, MD 21620
    /53

    $375,000 Sold Apr 16, 2025

    25740 Collins Ave, Chestertown, MD 21620

    • 5 Beds
    • 3 Baths
    • 3,389 Sq Ft
    • Built 1956

    Last Sold Summary

    • $111/SF
    • 29 Days On Market

    Current Estimated Value $424,444

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    25740 Collins Ave, Chestertown, MD 21620
    • 201 Princess Anne Dr, Chestertown, MD 21620
      201 Princess Anne Dr, Chestertown, MD 21620
      201 Princess Anne Dr, Chestertown, MD 21620
      /36

      Est $391,362 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,092 Sq Ft

      201 Princess Anne Dr, Chestertown, MD 21620

      201 Princess Anne Dr, Chestertown, MD 21620
  • 105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    /51

    $1,395,500

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

    105 High St, Chestertown, MD 21620

    This masterpiece is finally complete. Rebuilt in 1863, the Tilley Residence showcases classic Second Empire style on one of Chestertown’s most prominent corners, neighboring Widehall and the Custom House. Expertly restored in 2024–2025 by one of Kent County’s premier builders, the home offers new HVAC, electrical, plumbing, roofing, flooring, and a refreshed open layout. Custom kitchen and baths

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • 8951 Orchard Dr, Chestertown, MD 21620
    8951 Orchard Dr, Chestertown, MD 21620
    8951 Orchard Dr, Chestertown, MD 21620
    /47

    $700,000 Sold Dec 04, 2025

    8951 Orchard Dr, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 3,735 Sq Ft
    • Built 2014

    Last Sold Summary

    • $187/SF
    • 2 Days On Market

    Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

    8951 Orchard Dr, Chestertown, MD 21620
    • 124 Wilton Rd, Chestertown, MD 21620
      124 Wilton Rd, Chestertown, MD 21620
      124 Wilton Rd, Chestertown, MD 21620
      /18

      Est $301,668 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft

      124 Wilton Rd, Chestertown, MD 21620

      124 Wilton Rd, Chestertown, MD 21620
  • 404 Spring Rd, Chestertown, MD 21620
    404 Spring Rd, Chestertown, MD 21620
    404 Spring Rd, Chestertown, MD 21620
    /11

    $19,500

    • Land
    • 0.99 Acre
    • $19,697 per Acre

    404 Spring Rd, Chestertown, MD 21620

    This property, situated on a 0.99-acre lot, offers a blank canvas for your vision. Located in Queen Anne's County, you can take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details, zoning, and permitted uses. Don’t miss this opportunity to secure a piece of land in Kent

    Dustin Parker The Parker Group

    404 Spring Rd, Chestertown, MD 21620
  • 10262 John Carvill Rd, Chestertown, MD 21620
    10262 John Carvill Rd, Chestertown, MD 21620
    10262 John Carvill Rd, Chestertown, MD 21620
    /59

    $1,450,000 Sold Dec 20, 2024

    10262 John Carvill Rd, Chestertown, MD 21620

    • 5 Beds
    • 2 Baths
    • 3,788 Sq Ft
    • Built 1953

    Last Sold Summary

    • $383/SF
    • 4 Days On Market

    Current Estimated Value $1,644,473

    Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

    10262 John Carvill Rd, Chestertown, MD 21620
    • 121 Bass Track Ct, Chestertown, MD 21620
      121 Bass Track Ct, Chestertown, MD 21620
      121 Bass Track Ct, Chestertown, MD 21620
      /49

      Est $643,539 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,904 Sq Ft

      121 Bass Track Ct, Chestertown, MD 21620

      121 Bass Track Ct, Chestertown, MD 21620
  • 0 Melitota Ln, Chestertown, MD 21620
    0 Melitota Ln, Chestertown, MD 21620
    /2

    $29,000 Under Contract

    • Land
    • 2 Acres
    • $14,500 per Acre

    0 Melitota Ln, Chestertown, MD 21620

    2-acre wooded parcel on L Road. Short distance to Chestertown and amenities. See Documents for additional information. Out of Town Seller will pay for perk testing with Buyer making local arrangements. Seller has paperwork from the County to proceed when needed.

    Jo Ann Edwards The Hogans Agency

    0 Melitota Ln, Chestertown, MD 21620
  • 600 Rosin Dr, Chestertown, MD 21620
    600 Rosin Dr, Chestertown, MD 21620
    600 Rosin Dr, Chestertown, MD 21620
    /35

    $413,300 Sold Dec 05, 2025

    600 Rosin Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Built 1976

    Last Sold Summary

    • $318/SF
    • 34 Days On Market

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    600 Rosin Dr, Chestertown, MD 21620
    • 121 Lyons Ln, Chestertown, MD 21620
      121 Lyons Ln, Chestertown, MD 21620
      121 Lyons Ln, Chestertown, MD 21620
      /33

      Est $723,354 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,327 Sq Ft

      121 Lyons Ln, Chestertown, MD 21620

      121 Lyons Ln, Chestertown, MD 21620
  • 0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620
    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620
    /2

    $28,000 Pending

    • Land
    • 2 Acres
    • $14,000 per Acre

    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620
  • 249 Duke of Kent St, Chestertown, MD 21620
    249 Duke of Kent St, Chestertown, MD 21620
    249 Duke of Kent St, Chestertown, MD 21620
    /28

    $343,600 Sold Mar 26, 2025

    249 Duke of Kent St, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,556 Sq Ft
    • Built 2000

    Last Sold Summary

    • $221/SF
    • 14 Days On Market

    Current Estimated Value $349,106

    Last Listing Agent Lee Wolff FSBO Broker

    249 Duke of Kent St, Chestertown, MD 21620
    • 204 Truslow Farm Ln, Chestertown, MD 21620
      204 Truslow Farm Ln, Chestertown, MD 21620
      204 Truslow Farm Ln, Chestertown, MD 21620
      /12

      Est $907,023 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,945 Sq Ft

      204 Truslow Farm Ln, Chestertown, MD 21620

      204 Truslow Farm Ln, Chestertown, MD 21620
  • 8833 Georgetown Rd, Chestertown, MD 21620
    8833 Georgetown Rd, Chestertown, MD 21620
    8833 Georgetown Rd, Chestertown, MD 21620
    /47

    $364,000

    • 4 Beds
    • 2 Baths
    • 1,625 Sq Ft

    8833 Georgetown Rd, Chestertown, MD 21620

    Move-in ready and freshly updated in 2025! This 3-bedroom, 2-bath home offers approx. 1,600 sq. ft. of stylish living on an 2.66 acre corner lot with public water and sewer. Every detail has been thoughtfully upgraded—appliances and systems are brand new, complemented by luxury vinyl plank flooring throughout. The spacious layout includes a large mudroom and plenty of modern finishes. Located

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    8833 Georgetown Rd, Chestertown, MD 21620
  • 109 2nd St, Chestertown, MD 21620
    109 2nd St, Chestertown, MD 21620
    109 2nd St, Chestertown, MD 21620
    /9

    $75,000 Sold Dec 08, 2025

    109 2nd St, Chestertown, MD 21620

    • Land
    • 1.8 Acres
    • $41,667 per Acre

    Last Sold Summary

    • 49 Days On Market

    Last Listing Agent Adam Shpritz Ashland Auction Group LLC

    109 2nd St, Chestertown, MD 21620
    • 150 Longfellow Dr, Chestertown, MD 21620
      150 Longfellow Dr, Chestertown, MD 21620
      150 Longfellow Dr, Chestertown, MD 21620
      /31

      Est $307,056 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft

      150 Longfellow Dr, Chestertown, MD 21620

      150 Longfellow Dr, Chestertown, MD 21620
  • 0 Buck Neck Landing Rd, Chestertown, MD 21620
    0 Buck Neck Landing Rd, Chestertown, MD 21620
    /2

    $9,500

    • Land
    • 0.34 Acre
    • $27,941 per Acre

    0 Buck Neck Landing Rd, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Buck Neck Landing Rd, Chestertown, MD 21620
  • 143 Char Nor Manor Blvd, Chestertown, MD 21620
    143 Char Nor Manor Blvd, Chestertown, MD 21620
    143 Char Nor Manor Blvd, Chestertown, MD 21620
    /66

    $868,000 Sold Oct 15, 2025

    143 Char Nor Manor Blvd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,073 Sq Ft
    • Built 2001

    Last Sold Summary

    • $419/SF
    • 12 Days On Market

    Last Listing Agent Barbara McCaffrey Redfin Corp

    143 Char Nor Manor Blvd, Chestertown, MD 21620
    • 109 Pear Tree Point Rd, Chestertown, MD 21620
      109 Pear Tree Point Rd, Chestertown, MD 21620
      109 Pear Tree Point Rd, Chestertown, MD 21620
      /54

      Est $410,225 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,150 Sq Ft

      109 Pear Tree Point Rd, Chestertown, MD 21620

      109 Pear Tree Point Rd, Chestertown, MD 21620
  • 5700 Johnsontown Rd, Chestertown, MD 21620
    5700 Johnsontown Rd, Chestertown, MD 21620
    5700 Johnsontown Rd, Chestertown, MD 21620
    /7

    $110,000 Pending

    • 3 Beds
    • 1 Bath
    • 1,144 Sq Ft

    5700 Johnsontown Rd, Chestertown, MD 21620

    Serene 2-acre partially cleared wooded lot with existing 1900-built home, in need of major repair or possible tear-down. Value is in the land. No interior access – partial roof and floor collapse. Sellers accept no liability and are held harmless.Property includes well and septic (buyer to verify), detached building and shed. Close to water and surrounded by peace and privacy. Sold as-is;

    Nicole Stephens Tesla Realty Group, LLC

    5700 Johnsontown Rd, Chestertown, MD 21620
  • 0 Georgetown Rd SE Unit MDKE2005448, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005448, Chestertown, MD 21620
    /2

    $30,000 Sold Aug 29, 2025

    0 Georgetown Rd SE Unit MDKE2005448, Chestertown, MD 21620

    • Land
    • 0.83 Acre
    • $36,145 per Acre

    Last Sold Summary

    • 11 Days On Market

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Georgetown Rd SE Unit MDKE2005448, Chestertown, MD 21620
    • 200 Duke of Kent St, Chestertown, MD 21620
      200 Duke of Kent St, Chestertown, MD 21620
      200 Duke of Kent St, Chestertown, MD 21620
      /26

      Est $391,841 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,477 Sq Ft

      200 Duke of Kent St, Chestertown, MD 21620

      200 Duke of Kent St, Chestertown, MD 21620
  • 311 Devon Dr, Chestertown, MD 21620
    311 Devon Dr, Chestertown, MD 21620
    311 Devon Dr, Chestertown, MD 21620
    /40

    $598,000

    • 5 Beds
    • 3.5 Baths
    • 3,504 Sq Ft

    311 Devon Dr, Chestertown, MD 21620

    311 Devon Drive is located in Coventry Farms; and being located within the Chestertown town limits offers town utilities. The front entrance welcomes you with an open two-story foyer to the second-floor balcony. To the left of the front foyer is a den and to the right is a formal dining room. The foyer hall leads into a large open area that includes a large eat-in kitchen, sunroom and family room

    Debbie Meikle Doug Ashley Realtors, LLC

    311 Devon Dr, Chestertown, MD 21620
  • 129 N Queen St, Chestertown, MD 21620
    129 N Queen St, Chestertown, MD 21620
    129 N Queen St, Chestertown, MD 21620
    /38

    $575,000 Sold Jun 06, 2025

    129 N Queen St, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,296 Sq Ft
    • Built 1920

    Last Sold Summary

    • $250/SF
    • 19 Days On Market

    Current Estimated Value $572,223

    Last Listing Agent William Norris Select Land & Homes, LLC

    129 N Queen St, Chestertown, MD 21620
    • 103 Creston Rd, Chestertown, MD 21620
      103 Creston Rd, Chestertown, MD 21620
      103 Creston Rd, Chestertown, MD 21620
      /42

      Est $316,400 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,092 Sq Ft

      103 Creston Rd, Chestertown, MD 21620

      103 Creston Rd, Chestertown, MD 21620
  • 0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
    /8

    $150,000

    • Land
    • 2 Acres
    • $75,000 per Acre

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620

    Sebrin Adem RE/MAX Allegiance

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
  • 128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    /59

    $392,500 Sold Oct 30, 2025

    128 Edmore Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 2,568 Sq Ft
    • Built 1976

    Last Sold Summary

    • $153/SF
    • 180 Days On Market

    Last Listing Agent Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    128 Edmore Rd, Chestertown, MD 21620
    • 240 Princess Anne Dr, Chestertown, MD 21620
      240 Princess Anne Dr, Chestertown, MD 21620
      240 Princess Anne Dr, Chestertown, MD 21620
      /34

      Est $443,161 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,067 Sq Ft

      240 Princess Anne Dr, Chestertown, MD 21620

      240 Princess Anne Dr, Chestertown, MD 21620
  • 0 Elm Rd, Chestertown, MD 21620
    0 Elm Rd, Chestertown, MD 21620
    /2

    $40,000

    • Land
    • 0.33 Acre
    • $121,212 per Acre

    0 Elm Rd, Chestertown, MD 21620

    Water oriented community of Tolchester Estates. Public record says Montgomery but the correct address is Elm Road. Approved for sewer allocation. Please see recent survey in documents.

    Vaughn Hogans The Hogans Agency

    0 Elm Rd, Chestertown, MD 21620
  • 9048 Georgetown Rd, Chestertown, MD 21620
    9048 Georgetown Rd, Chestertown, MD 21620
    /2

    $45,000 Sold Mar 26, 2025

    9048 Georgetown Rd, Chestertown, MD 21620

    • Land
    • 1.21 Acres
    • $37,190 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 713 Days On Market

    Current Estimated Value $51,956

    Last Listing Agent Beverly Sloane Benson & Mangold, LLC

    9048 Georgetown Rd, Chestertown, MD 21620
    • 209 Princess Anne Dr, Chestertown, MD 21620
      209 Princess Anne Dr, Chestertown, MD 21620
      209 Princess Anne Dr, Chestertown, MD 21620
      /26

      Est $442,928 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,776 Sq Ft

      209 Princess Anne Dr, Chestertown, MD 21620

      209 Princess Anne Dr, Chestertown, MD 21620
  • Parcel Buck Neck Ldg Rd, Chestertown, MD 21620
    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620
    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620
    /6

    $10,000

    • Land
    • 0.34 Acre
    • $29,412 per Acre

    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620

    POST AUCTION: MAKE AN OFFER! Lot of Land located outside of Chestertown, Maryland within Kent County. Nearby attractions include Warton Creek Marina, Warton Creek, Attractions along Chesapeake Bay, & +/- 7 Miles to downtown Chestertown, Maryland. Easy Access to Major Traffic Artery Fairlee Road. Deposit: $5,000.

    Adam Shpritz Ashland Auction Group LLC

    Parcel Buck Neck Ldg Rd, Chestertown, MD 21620
  • 306 Cedar St, Chestertown, MD 21620
    306 Cedar St, Chestertown, MD 21620
    306 Cedar St, Chestertown, MD 21620
    /42

    $312,000 Sold Jun 13, 2025

    306 Cedar St, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,404 Sq Ft
    • Built 1959

    Last Sold Summary

    • $222/SF
    • 55 Days On Market

    Current Estimated Value $320,361

    Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

    306 Cedar St, Chestertown, MD 21620
    • 112 Pine Chip Rd, Chestertown, MD 21620
      112 Pine Chip Rd, Chestertown, MD 21620
      112 Pine Chip Rd, Chestertown, MD 21620
      /21

      Est $347,428 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,248 Sq Ft

      112 Pine Chip Rd, Chestertown, MD 21620

      112 Pine Chip Rd, Chestertown, MD 21620
  • 7653 Broad Neck Rd, Chestertown, MD 21620
    7653 Broad Neck Rd, Chestertown, MD 21620
    7653 Broad Neck Rd, Chestertown, MD 21620
    /39

    $375,000 Under Contract

    • 4 Beds
    • 3 Baths
    • 1,790 Sq Ft

    7653 Broad Neck Rd, Chestertown, MD 21620

    Recently and thoroughly renovated, charming and spacious 4 bedroom 3 bathroom home located only about 6 miles from Chestertown in an idyllic country setting. Some improvements include new HVAC, electric, 3 season room , water filter and high-end, smart appliances. Terrific in-ground pool enclosed with privacy brick wall, a large patio and deck are perfect for entertaining or relaxing in the

    Brian Petzold Benson & Mangold, LLC

    7653 Broad Neck Rd, Chestertown, MD 21620
  • 7500 Shortall St, Chestertown, MD 21620
    7500 Shortall St, Chestertown, MD 21620
    7500 Shortall St, Chestertown, MD 21620
    /24

    $299,900 Sold Jan 31, 2025

    7500 Shortall St, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft
    • Built 2018

    Last Sold Summary

    • $233/SF
    • 30 Days On Market

    Current Estimated Value $320,680

    Last Listing Agent Lona Todd Taylor Properties

    7500 Shortall St, Chestertown, MD 21620
    • 201 Duke of Kent St, Chestertown, MD 21620
      201 Duke of Kent St, Chestertown, MD 21620
      201 Duke of Kent St, Chestertown, MD 21620
      /5

      Est $391,991 Not Listed For Sale

      201 Duke of Kent St, Chestertown, MD 21620

      201 Duke of Kent St, Chestertown, MD 21620
  • 100 Adela Way, Chestertown, MD 21620
    100 Adela Way, Chestertown, MD 21620
    100 Adela Way, Chestertown, MD 21620
    /71

    $515,000

    • 4 Beds
    • 3.5 Baths
    • 3,799 Sq Ft

    100 Adela Way, Chestertown, MD 21620

    *Days on Market Reporting Incorrectly- Property listed Oct 30, 2025* Nestled just outside of historic Chestertown, minutes from farmers market, waterfront park and local shops and eateries. This home offers the best of small-town living with modern updates at every turn.Step inside to discover wood floors, a private home office, and an inviting open-concept kitchen featuring luxury

    Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    100 Adela Way, Chestertown, MD 21620
  • 10724 Foreston Rd, Chestertown, MD 21620
    10724 Foreston Rd, Chestertown, MD 21620
    10724 Foreston Rd, Chestertown, MD 21620
    /35

    $355,675 Sold Feb 28, 2025

    10724 Foreston Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft
    • Built 1995

    Last Sold Summary

    • $190/SF
    • 3 Days On Market

    Current Estimated Value $374,241

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    10724 Foreston Rd, Chestertown, MD 21620

Showing Results 121 - 160, Page 4 of 18

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