7,014

Homes in ZIP Code 21620

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  • /2

    $37,000

    • Land
    • 0.34 Acre
    • $108,824 per Acre

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Fish Hatchery Rd Unit MDKE2002848, Chestertown, MD 21620
  • /4

    $15,000 Sold Jun 02, 2025

    • Land
    • 0.48 Acre
    • $31,250 per Acre
    • 4 Days On Market

    22671 Wood Yard Ln, Chestertown, MD 21620

    Almost half acre of recreational property available between Chestertown and Rock Hall! Best use would be hunting since it is surrounded by woods and farms. There is an existing structure that is a tear down of no value. There appears to be electric run to the property but condition is unknown. The county does not have records of the septic and would need to be perc tested to build on. The back of

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    22671 Wood Yard Ln, 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
  • /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
  • /53

    $375,000 Sold Apr 16, 2025

    • 3,389 Sq Ft
    • $111/SF
    • 29 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1956

    25740 Collins Ave, Chestertown, MD 21620

    Large Home with Private Pool & Separate Apartment!Nestled in a prime location, this solid, well-maintained home offers breathtaking views of the Chester River Yacht and Country Club Golf Course, creating an inviting and peaceful atmosphere. Originally built in 1956, the character and charm of this property shine through, with a cozy wood stove in the large den, and a welcoming fireplace

    Retha Arrabal Doug Ashley Realtors, LLC

    25740 Collins Ave, 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
  • /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
  • /47

    $700,000 Sold Dec 04, 2025

    • 3,735 Sq Ft
    • $187/SF
    • 2 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2014

    8951 Orchard Dr, Chestertown, MD 21620

    Nestled in the serene Orchard Hill community, this stunning Craftsman-Colonial offers 3,735 sq. ft. of luxury and comfort. The open, light-filled floor plan showcases rich hardwood floors and elegant finishes throughout. The gourmet kitchen features upgraded countertops, pecan wood-stained cherry cabinetry, stainless steel appliances, including double ovens, a gas cooktop, and a tankless water

    Sarah Ulrick Rock Hall Properties Real Estate

    8951 Orchard Dr, 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
  • /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
  • /59

    $1,450,000 Sold Dec 20, 2024

    • 3,788 Sq Ft
    • $383/SF
    • 4 Days On Market
    • 5 Beds
    • 2 Baths
    • Built 1953

    10262 John Carvill Rd, Chestertown, MD 21620

    This beloved waterfront property has been a treasured family gathering place for over twenty four years. There have been numerous updates throughout that time, including the spectacular shoreline area which offers a private dock with about 5 feet MLW, bulk-headed shoreline, several boat lifts, water slide and sandy beach. From the homesite, you can walk down the well constructed stairs or you

    Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

    10262 John Carvill Rd, 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
  • /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
  • /35

    $413,300 Sold Dec 05, 2025

    • 1,300 Sq Ft
    • $318/SF
    • 34 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1976

    600 Rosin Dr, Chestertown, MD 21620

    Charming 3-bedroom, 2-bathroom waterfront cottage nestled along the peaceful shores of Rosin Creek. Combining classic character with modern updates, the open floor plan creates a warm and inviting flow. Perfect for everyday living or entertaining. The renovated kitchen features stylish finishes and connects seamlessly to the dining and living areas. Updated flooring throughout the downstairs,

    Michele Palmer Doug Ashley Realtors, LLC

    600 Rosin 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
  • /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
  • /28

    $343,600 Sold Mar 26, 2025

    • 1,556 Sq Ft
    • $221/SF
    • 14 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2000

    249 Duke of Kent St, Chestertown, MD 21620

    Lovely all one floor living in quiet neighborhood with updated features throughout! Brand new gorgeous kitchen with white shaker cabinetry featuring dovetail construction soft close drawers, solid butcher block countertops, tile backsplash, large island, brand new stainless steel appliances and much more! eng hardwood flooring, recessed lighting, vertical custom ship lap, gas fireplace, screened

    Lee Wolff FSBO Broker

    249 Duke of Kent St, 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
  • /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
  • /9

    $75,000 Sold Dec 08, 2025

    • Land
    • 1.8 Acres
    • $41,667 per Acre
    • 49 Days On Market

    109 2nd St, Chestertown, MD 21620

    ONLINE AUCTION: Bidding begins 11/12/2025 @ 10:00 AM. Bidding ends 11/14/2025 @ 11:40 AM. List Price is Suggested Opening Bid. Deposit: $5,000. This +/- 1.80 acres lot of land located is in Chestertown, MD within Queen Anne’s County. A prior soil evaluation completed by the Queen Anne’s County Health Department (7/17/2009) certified suitability for a conventional mound septic system, confirming

    Adam Shpritz Ashland Auction Group LLC

    109 2nd 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
  • /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
  • /66

    $868,000 Sold Oct 15, 2025

    • 2,073 Sq Ft
    • $419/SF
    • 12 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2001

    143 Char Nor Manor Blvd, Chestertown, MD 21620

    Welcome to a rare opportunity for luxury waterfront living on the Chester River. This beautifully maintained 3-bedroom, 2.5-bath home offers over 2,000 square feet of living space, thoughtfully designed to embrace both comfort and elegance. Set on 1.08 acres of lush, well-landscaped grounds, this exceptional 2001-built two-story residence offers a park-like, deep, well-landscaped and level

    Barbara McCaffrey Redfin Corp

    143 Char Nor Manor Blvd, 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
  • /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
  • /2

    $30,000 Sold Aug 29, 2025

    • Land
    • 0.83 Acre
    • $36,145 per Acre
    • 11 Days On Market

    0 Georgetown Rd SE Unit MDKE2005448, Chestertown, MD 21620

    Wooded 0.8+ acre building lot on Georgetown Rd in Fairlee, just minutes from Chestertown, Tolchester, Rock Hall, and the Fairlee Boat Ramp. Water and sewer assessment already paid—no perc test needed! A convenient and ready-to-build spot for your Eastern Shore getaway!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Georgetown Rd SE Unit MDKE2005448, 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
  • /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
  • /38

    $575,000 Sold Jun 06, 2025

    • 2,296 Sq Ft
    • $250/SF
    • 19 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1920

    129 N Queen St, Chestertown, MD 21620

    Welcome to 129 N. Queen Street situated in one of Historic Chestertown's most desirable and sought after locations. Nestled among multiple other restored and renovated residences, this home itself has undergone a tasteful and remarkable transformation. The entire interior has been completely renovated over the past several years utilizing many new modern materials blended with some original

    William Norris Select Land & Homes, LLC

    129 N Queen St, 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
  • /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
  • /59

    $392,500 Sold Oct 30, 2025

    • 2,568 Sq Ft
    • $153/SF
    • 180 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1976

    128 Edmore Rd, Chestertown, MD 21620

    Your Dream Eastern Shore Retreat Awaits! Welcome to this meticulously maintained home, where charm and comfort blend seamlessly. Whether you're savoring peaceful nights or hosting lively gatherings, this home offers the perfect setting. Step into the breathtaking four-seasons room, where natural light pours in, highlighting an authentic reclaimed barn wood accent wall—crafted from the family’s

    Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    128 Edmore 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
  • /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
  • /2

    $45,000 Sold Mar 26, 2025

    • Land
    • 1.21 Acres
    • $37,190 per Acre
    • 713 Days On Market

    9048 Georgetown Rd, Chestertown, MD 21620

    Buildable parcel with the possibility of subdividing into 2 lots.

    Beverly Sloane Benson & Mangold, LLC

    9048 Georgetown Rd, 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
  • /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
  • /42

    $312,000 Sold Jun 13, 2025

    • 1,404 Sq Ft
    • $222/SF
    • 55 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1959

    306 Cedar St, Chestertown, MD 21620

    Lovely 4 bedroom, 2 bath Cape Cod located in College Heights. The house has been freshly painted inside and out and has a new roof. Mostly wood floors throughout the house. Living room has a fireplace but the fireplace is not in working order. The kitchen/dining combo has parquet wood floors. There is a full unimproved basement that was waterproofed sometime in the past and has both inside

    Doug Ashley Doug Ashley Realtors, LLC

    306 Cedar St, Chestertown, MD 21620
    • /24

      Est $309,736 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,216 Sq Ft

      2607 Mcginnes Rd, Chestertown, MD 21620

      2607 Mcginnes Rd, 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

Showing Results 121 - 160, Page 4 of 18

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