6,852

Chestertown, MD Homes

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  • 116 Harlan Loop, Chestertown, MD 21620
    116 Harlan Loop, Chestertown, MD 21620
    116 Harlan Loop, Chestertown, MD 21620
    /21

    $529,000

    • 5 Beds
    • 3.5 Baths
    • 4,067 Sq Ft

    116 Harlan Loop, Chestertown, MD 21620

    Welcome to Coventry Farms in Chestertown — where comfort, elegance, and space come together in this stunning colonial-style home!Built in 2009 and meticulously maintained, this spacious property offers over 4,000 square feet of finished living space across three levels — including a fully finished basement with a full bath, perfect for entertaining, a guest suite, or a home office

    Agent Photo

    Floretta Davis

    Samson Properties

    (410) 406-6980

    116 Harlan Loop, Chestertown, MD 21620
  • 10743 Millbrook Dr, Chestertown, MD 21620
    10743 Millbrook Dr, Chestertown, MD 21620
    10743 Millbrook Dr, Chestertown, MD 21620
    /17

    $2,490 per month

    • 4 Beds
    • 2.5 Baths
    • 2,009 Sq Ft
    • House for Rent

    10743 Millbrook Dr, Chestertown, MD 21620

    Property Id: 2145452This beautiful 4-bedroom, 2.5-bath with 1st floor master suite rental home in charming Chesapeake Landing offers a peaceful retreat in a quiet neighborhood surrounded by mature trees and a wooded area in the back. Just 5 miles from Chestertown, this home was built in 1987 and thoughtfully updated with modern conveniences. Featuring stainless steel appliances, granite

    10743 Millbrook Dr, Chestertown, MD 21620
  • 0 Hoffecker Rd, Chestertown, MD 21620
    0 Hoffecker Rd, Chestertown, MD 21620
    0 Hoffecker Rd, Chestertown, MD 21620
    /5

    $160,000 Sold Sep 15, 2025

    • Land
    • 10.05 Acres
    • $15,920 per Acre
    • 26 Days On Market

    0 Hoffecker Rd, Chestertown, MD 21620

    Serene 10-acre wooded lot on Hoffecker Rd. A short distance to the Deep Landing boat launch and historic Chestertown. This parcel offers the perfect balance of seclusion and convenience, surrounded by farmland, beautiful trees, and a short distance to the Chester River. Tons of potential to become a family retreat or private future home.Perc test completed.

    John Burke Gunther-McClary Real Estate

    0 Hoffecker Rd, Chestertown, MD 21620
    • 10572 Klamath Rd, Chestertown, MD 21620
      10572 Klamath Rd, Chestertown, MD 21620
      10572 Klamath Rd, Chestertown, MD 21620
      /27

      Est $283,022 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft

      10572 Klamath Rd, Chestertown, MD 21620

      10572 Klamath Rd, Chestertown, MD 21620
  • 117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    /28

    $725,000

    • 3 Beds
    • 3 Baths

    117 N Water St Unit 1A, Chestertown, MD 21620

    Completely remodeled, this three-bedroom waterfront home boasts a charming front porch and enormous back porch - your private space overlooking the river - along with an enclosed sunroom featuring gorgeous river views through walls of windows. Enjoy abundant outdoor areas and stunning water views from nearly every room. The dock features 3+ feel MLW, with slips available for purchase. This

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 589-6299

    117 N Water St Unit 1A, Chestertown, MD 21620
  • 104 Maple Ave, Chestertown, MD 21620
    104 Maple Ave, Chestertown, MD 21620
    104 Maple Ave, Chestertown, MD 21620
    /38

    $2,175 per month

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    104 Maple Ave, Chestertown, MD 21620

    Welcome to your new home in the heart of Chestertown Maryland, a charming historic town nestled along the Chester River, known for its vibrant arts scene, waterfront dining, and small-town charm.This beautifully designed property blends modern finishes with timeless appeal. Step inside to find engineered hardwood floors flowing throughout the main living areas, creating both warmth and

    Nicolas Dively Real Broker, LLC - Annapolis

    104 Maple Ave, Chestertown, MD 21620
  • 9190 N Bayview Ave, Chestertown, MD 21620
    9190 N Bayview Ave, Chestertown, MD 21620
    9190 N Bayview Ave, Chestertown, MD 21620
    /38

    $285,000 Sold Sep 05, 2025

    • 1,160 Sq Ft
    • $246/SF
    • 12 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1969

    9190 N Bayview Ave, Chestertown, MD 21620

    This 2 bedroom, 1-bath home offers a peaceful escape with views of the Chesapeake Bay. Nestled in Tolchester Estates community, the property is just a short stroll from Tolchester Marina, a boat ramp, and a sandy public beach—making it a perfect retreat for boating, beach going, or simply enjoying being close to the water. The home’s layout makes it an ideal weekend getaway or low-maintenance

    Hayley Norris Select Land & Homes, LLC

    9190 N Bayview Ave, Chestertown, MD 21620
    • 148 Grant Ct, Chestertown, MD 21620
      148 Grant Ct, Chestertown, MD 21620
      148 Grant Ct, Chestertown, MD 21620
      /30

      Est $469,357 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,664 Sq Ft

      148 Grant Ct, Chestertown, MD 21620

      148 Grant Ct, Chestertown, MD 21620
  • Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    /20

    $185,000

    • Land
    • 1.95 Acres
    • $94,872 per Acre

    Lot 9 Prestwick Dr, Chestertown, MD 21620

    Lot 9 overlooks the 5th hole tee box and the picturesque par 3 water hole # 4. Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 806-9518

    Lot 9 Prestwick Dr, Chestertown, MD 21620
  • 128 N Queen St Unit 4, Chestertown, MD 21620
    128 N Queen St Unit 4, Chestertown, MD 21620
    128 N Queen St Unit 4, Chestertown, MD 21620
    /10

    $1,450 per month

    • 1 Bed
    • 1 Bath
    • 1,455 Sq Ft
    • Condo for Rent

    128 N Queen St Unit 4, Chestertown, MD 21620

    Move in ready 2nd floor apartment in Downtown Chestertown. One spacious bedroom, full bathroom, living area and a step-up cove/office space. Conveniently located within walking distance to the Chester River. Utilities included with the exception of Internet/Cable. All applicants apply through Rent Spree.

    Amanda Morgan Brenton Realty Group

    128 N Queen St Unit 4, Chestertown, MD 21620
  • 7425 Wilkins Ln, Chestertown, MD 21620
    7425 Wilkins Ln, Chestertown, MD 21620
    7425 Wilkins Ln, Chestertown, MD 21620
    /29

    $315,000 Sold Aug 29, 2025

    • 1,341 Sq Ft
    • $235/SF
    • 6 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1962

    7425 Wilkins Ln, Chestertown, MD 21620

    Welcome to 7425 Wilkins Lane, Chestertown, MDJust two miles from the charming town of Chestertown, this beautifully renovated 3-bedroom, 2-bath home offers the perfect blend of modern comfort and peaceful country living.Completely renovated down to the studs, this home features a new roof, new plywood, home addition including the kitchen, full bath and laundry room, siding,

    LAURIE KREIDER Realty ONE Group Unlimited

    7425 Wilkins Ln, Chestertown, MD 21620
    • 104 Metcalf Rd, Chestertown, MD 21620
      104 Metcalf Rd, Chestertown, MD 21620
      104 Metcalf Rd, Chestertown, MD 21620
      /17

      Est $280,158 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths

      104 Metcalf Rd, Chestertown, MD 21620

      104 Metcalf Rd, Chestertown, MD 21620
  • 117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    /28

    $399,000

    • 2 Beds
    • 1 Bath
    • 787 Sq Ft

    117 N Water St Unit 2A, Chestertown, MD 21620

    A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. This unit offers a 2 Bed 1 bath has a brand new kitchen, with island and upgraded bathroom along with up and down river views. Enjoy all the amenities of living waterfront--Community

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 824-5609

    117 N Water St Unit 2A, Chestertown, MD 21620
  • 101 Morgnec Rd, Chestertown, MD 21620
    101 Morgnec Rd, Chestertown, MD 21620
    101 Morgnec Rd, Chestertown, MD 21620
    /11

    $1,300 per month

    • 1 Bed
    • 1 Bath
    • 785 Sq Ft
    • Condo for Rent

    101 Morgnec Rd, Chestertown, MD 21620

    One, two and three bedroom apartments located near Washington College, wellness/ rehab center, Churches, shopping and a short walk to downtown Chestertown. Short distance to the Chester River and Chesapeake Bay. Immediate Availability.

    Herschell Claggett Davis Real Estate, Inc.

    101 Morgnec Rd, Chestertown, MD 21620
  • 106 Wilton Rd, Chestertown, MD 21620
    106 Wilton Rd, Chestertown, MD 21620
    106 Wilton Rd, Chestertown, MD 21620
    /36

    $315,000 Sold Aug 29, 2025

    • 1,056 Sq Ft
    • $298/SF
    • 18 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1975

    106 Wilton Rd, Chestertown, MD 21620

    Charming Updated and Well Maintained Rancher in the Chester Harbor Community of Queen Anne's County Chestertown! This house is the definition of "move-in ready" as the owner has taken tremendous pride in keeping the property updated. Over the years, they've installed new windows, new HVAC unit, new hot water heater, remodeled the kitchen, installed new appliances, painted the interior, added new

    Crystal Smith RE/MAX Executive

    106 Wilton Rd, Chestertown, MD 21620
    • 21357 Belair Ave, Chestertown, MD 21620
      21357 Belair Ave, Chestertown, MD 21620
      21357 Belair Ave, Chestertown, MD 21620
      /27

      Est $416,713 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,008 Sq Ft

      21357 Belair Ave, Chestertown, MD 21620

      21357 Belair Ave, Chestertown, MD 21620
  • 206 Cannon St, Chestertown, MD 21620
    206 Cannon St, Chestertown, MD 21620
    206 Cannon St, Chestertown, MD 21620
    /9

    $1,150,000

    • Land
    • 1.56 Acres
    • $737,179 per Acre

    206 Cannon St, Chestertown, MD 21620

    Extraordinary development opportunity in downtown historic Chestertown. Large parcel of land (1.56+/- acres) zoned C-2 (half R1 and half R5 zoning) many permitted uses such as Muliple-Family dwelling, Townhouses, professional and business offices, non-profit museums, and others. Includes 1 building (Warehouse) and property fronts on three streets. Excellent location-- just a few blocks to the

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (443) 419-7633

    206 Cannon St, Chestertown, MD 21620
  • 10715 Kasota Rd, Chestertown, MD 21620
    10715 Kasota Rd, Chestertown, MD 21620
    10715 Kasota Rd, Chestertown, MD 21620
    /49

    $960,000 Sold Aug 27, 2025

    • 3,401 Sq Ft
    • $282/SF
    • 5 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2005

    10715 Kasota Rd, Chestertown, MD 21620

    Private waterfront retreat on Mill Creek offering beautiful views, spacious living, and all the peace and quiet you have been looking for. This custom-built Cape-style home is nestled on a serene, protected stretch of water and offers the ideal blend of comfort and tranquility. With 4 bedrooms and 3 full baths, the home features a flexible floor plan designed for both everyday living and

    Sarah King Cross Street Realtors LLC

    10715 Kasota Rd, Chestertown, MD 21620
    • 213 Pine Cove Ln, Chestertown, MD 21620
      213 Pine Cove Ln, Chestertown, MD 21620
      213 Pine Cove Ln, Chestertown, MD 21620
      /16

      Est $388,573 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,400 Sq Ft

      213 Pine Cove Ln, Chestertown, MD 21620

      213 Pine Cove Ln, Chestertown, MD 21620
  • 110 S Mill St, Chestertown, MD 21620
    110 S Mill St, Chestertown, MD 21620
    110 S Mill St, Chestertown, MD 21620
    /39

    $745,000 Pending

    • 3 Beds
    • 3.5 Baths
    • 2,492 Sq Ft

    110 S Mill St, Chestertown, MD 21620

    Beautiful and spacious 3- bedroom home in historic Chestertown. Just a short distance from vibrant shops, restaurants, and the scenic Chester River waterfront.The gourmet kitchen has a beautiful wood-top island and stainless steel appliances. The kitchen leads to the large formal dining room, featuring the original stone fireplace, updated with a gas insert. The living space is

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 514-3490

    110 S Mill St, Chestertown, MD 21620
  • 10175 John Carvill Rd, Chestertown, MD 21620
    10175 John Carvill Rd, Chestertown, MD 21620
    10175 John Carvill Rd, Chestertown, MD 21620
    /72

    $609,000 Sold Aug 27, 2025

    • 3,155 Sq Ft
    • $193/SF
    • 11 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1994

    10175 John Carvill Rd, Chestertown, MD 21620

    Welcome to 10175 John Carvill Road, nestled in the desirable water-oriented community of Great Oak Estates. This spacious home offers an open floor plan with 5 bedrooms and 3.5 baths, hardwood floors throughout the first floor, a cathedral ceiling, gas fireplace in the family room, and two primary suites. Enjoy the private fenced backyard and the sense of space that comes with it. The

    Hayley Norris Select Land & Homes, LLC

    10175 John Carvill Rd, Chestertown, MD 21620
    • 7499 Poplar Ave, Chestertown, MD 21620
      7499 Poplar Ave, Chestertown, MD 21620
      7499 Poplar Ave, Chestertown, MD 21620
      /34

      Est $281,852 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft

      7499 Poplar Ave, Chestertown, MD 21620

      7499 Poplar Ave, Chestertown, MD 21620
  • 21082 Wyoming Ave, Chestertown, MD 21620
    21082 Wyoming Ave, Chestertown, MD 21620
    21082 Wyoming Ave, Chestertown, MD 21620
    /63

    $1,550,000 Pending

    • 3 Beds
    • 3.5 Baths
    • 2,699 Sq Ft

    21082 Wyoming Ave, Chestertown, MD 21620

    Charming Chesapeake Bay Home with Stunning Water Views and Incredible Sunsets! Living space is 2699 and the unfinished basement is 1948. Additional guest house adds additional square footage, a kitchen/bath/sleeping area and living room. Discover the beauty of waterfront living in this exquisite home featuring panoramic views of the Chesapeake Bay. Having undergone a comprehensive

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 883-5429

    21082 Wyoming Ave, Chestertown, MD 21620
  • 7071 Pomona Rd, Chestertown, MD 21620
    7071 Pomona Rd, Chestertown, MD 21620
    7071 Pomona Rd, Chestertown, MD 21620
    /47

    $690,000 Sold Aug 25, 2025

    • 2,544 Sq Ft
    • $271/SF
    • 3 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 1991

    7071 Pomona Rd, Chestertown, MD 21620

    Welcome to your Eastern Shore escape—where timeless charm meets modern convenience on over four beautifully private acres in the heart of Quaker Neck. Just a short drive from historic Chestertown, this double-lot property invites you to embrace a slower pace, with all the major updates already completed: new septic, HVAC, and roof in 2021, plus thoughtful improvements through 2025 including a

    Liddy Campbell TTR Sotheby's International Realty

    7071 Pomona Rd, Chestertown, MD 21620
    • 724 Deep Landing Rd, Chestertown, MD 21620
      724 Deep Landing Rd, Chestertown, MD 21620
      724 Deep Landing Rd, Chestertown, MD 21620
      /63

      Est $366,197 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,311 Sq Ft

      724 Deep Landing Rd, Chestertown, MD 21620

      724 Deep Landing Rd, Chestertown, MD 21620
  • 9194 N Bayview Ave, Chestertown, MD 21620
    9194 N Bayview Ave, Chestertown, MD 21620
    9194 N Bayview Ave, Chestertown, MD 21620
    /45

    $698,000 Under Contract

    • 2 Beds
    • 2 Baths
    • 1,460 Sq Ft

    9194 N Bayview Ave, Chestertown, MD 21620

    Stunning home and property with 180-degree views of the Chesapeake Bay.The home was completely remodeled in 2017 by Taylor Loughry Construction. Boasting a bright open floor plan with high-end finishing, vaulted ceilings with skylights, and beautifully landscaped outdoor space. Two bedrooms and two full bathrooms, open living space with a gourmet kitchen, and a large deck overlooking the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 650-6367

    9194 N Bayview Ave, Chestertown, MD 21620
  • 209 River Rd, Chestertown, MD 21620
    209 River Rd, Chestertown, MD 21620
    209 River Rd, Chestertown, MD 21620
    /3

    $124,000 Sold Aug 25, 2025

    • Land
    • 1.01 Acres
    • $122,772 per Acre
    • 8 Days On Market

    209 River Rd, Chestertown, MD 21620

    A perc approved one acre open lot in a an established neighborhood ready for your dream home. No trees to clear and no restrictions except Critical Area guidelines. Perfectly located within a couple of minutes to downtown Historic Chestertown.

    Hayley Norris Select Land & Homes, LLC

    209 River Rd, Chestertown, MD 21620
    • 10570 Cogar Rd, Chestertown, MD 21620
      10570 Cogar Rd, Chestertown, MD 21620
      10570 Cogar Rd, Chestertown, MD 21620
      /56

      Est $394,278 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,862 Sq Ft

      10570 Cogar Rd, Chestertown, MD 21620

      10570 Cogar Rd, Chestertown, MD 21620
  • 304 Hilltop Ln, Chestertown, MD 21620
    304 Hilltop Ln, Chestertown, MD 21620
    304 Hilltop Ln, Chestertown, MD 21620
    /31

    $209,900 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,199 Sq Ft

    304 Hilltop Ln, Chestertown, MD 21620

    The townhouse is the second from the end and has three bedrooms and 2.5 baths. The slider door provides easy access to the patio and there is a stack washer on the main level, kitchen has the needed appliances. Located in Chestertown you can enjoy all of the amenities of this historic town, the Farmer's Market, Washington College is only a couple of minutes away, the many parks, marinas, and

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 824-5679

    304 Hilltop Ln, Chestertown, MD 21620
  • 114 Darden Rd, Chestertown, MD 21620
    114 Darden Rd, Chestertown, MD 21620
    114 Darden Rd, Chestertown, MD 21620
    /33

    $270,000 Sold Aug 25, 2025

    • 1,056 Sq Ft
    • $256/SF
    • 72 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1978

    114 Darden Rd, Chestertown, MD 21620

    All one floor living on quiet street with large fenced yard and mature trees close to the bay! Lovely renovations and brand new kitchen with solid white shaker cabinetry including soft close dovetailed drawers and new stainless steel appliances PLUS BRAND NEW ROOF! Brand New septic system to be installed by settlement! ABSOLUTE MUST SEE HOME!

    Lee Wolff FSBO Broker

    114 Darden Rd, Chestertown, MD 21620
    • 209 Blakefield Dr, Chestertown, MD 21620
      209 Blakefield Dr, Chestertown, MD 21620
      209 Blakefield Dr, Chestertown, MD 21620
      /9

      Est $459,695 Not Listed For Sale

      • 3 Beds
      • 2 Baths

      209 Blakefield Dr, Chestertown, MD 21620

      209 Blakefield Dr, Chestertown, MD 21620
  • 23065 Old Fairlee Rd, Chestertown, MD 21620
    23065 Old Fairlee Rd, Chestertown, MD 21620
    23065 Old Fairlee Rd, Chestertown, MD 21620
    /10

    $149,000

    • 3 Beds
    • 1 Bath
    • 1,176 Sq Ft

    23065 Old Fairlee Rd, Chestertown, MD 21620

    This home is priced to SELL! Bring your vision and bring this sweet property back to life. Nice lot - with a storage shed, mature trees ring part of the property lines in the back yard. There are three bedrooms and one bath, kitchen, utility room, a fireplace in the living room. Located in tranquil Fairlee - with easy access to public landings, Chestertown, Rock Hall and the beautiful

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 888-0767

    23065 Old Fairlee Rd, Chestertown, MD 21620
  • 10624 Millbrook Dr, Chestertown, MD 21620
    10624 Millbrook Dr, Chestertown, MD 21620
    10624 Millbrook Dr, Chestertown, MD 21620
    /20

    $246,000 Sold Aug 15, 2025

    • 1,000 Sq Ft
    • $246/SF
    • 17 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1988

    10624 Millbrook Dr, Chestertown, MD 21620

    Charming One-Level Living Near the Chesapeake Bay!This 3-bedroom, 1-bath home offers comfortable one-level living on a spacious 0.45-acre lot just minutes from downtown Chestertown. With 1,000 sq ft of living space, the home features a bright interior, a walk-in shower, and recent updates including a plastic vapor barrier in the crawl space for peace of mind.Enjoy your mornings on

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    10624 Millbrook Dr, Chestertown, MD 21620
    • 1213 Ewingtown Rd, Chestertown, MD 21620
      1213 Ewingtown Rd, Chestertown, MD 21620
      1213 Ewingtown Rd, Chestertown, MD 21620
      /25

      Est $421,214 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,528 Sq Ft

      1213 Ewingtown Rd, Chestertown, MD 21620

      1213 Ewingtown Rd, Chestertown, MD 21620
  • 21316 Persimmon Dr, Chestertown, MD 21620
    21316 Persimmon Dr, Chestertown, MD 21620
    21316 Persimmon Dr, Chestertown, MD 21620
    /25

    $179,000

    • 2 Beds
    • 1 Bath
    • 1,232 Sq Ft

    21316 Persimmon Dr, Chestertown, MD 21620

    Two bedroom & one bath townhome with a nice view from the living room/patio area. Located very close to a public landing and Tolchester Marina, which offers full service. This townhouse has outdoor storage both on the front patio area and the back patio area. New carpet and fresh paint will update this property nicely. Covered storage for bikes/yard toys and more. The townhouse is all

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 708-2172

    21316 Persimmon Dr, Chestertown, MD 21620
  • 206 Silver Heel Dr, Chestertown, MD 21620
    206 Silver Heel Dr, Chestertown, MD 21620
    206 Silver Heel Dr, Chestertown, MD 21620
    /36

    $375,000 Sold Aug 13, 2025

    • 2,302 Sq Ft
    • $163/SF
    • 1 Day On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2022

    206 Silver Heel Dr, Chestertown, MD 21620

    Welcome to The Verona in The Village at Chestertown—a beautifully designed, move-in ready home offering 2,302 square feet of flexible living space across three levels. With 5 bedrooms and 3.5 bathrooms, this home perfectly balances comfort, function, and style. Step inside to a welcoming foyer that leads into a spacious family room, ideal for relaxing or entertaining. The open-concept layout

    TJ Bennett Samson Properties

    206 Silver Heel Dr, Chestertown, MD 21620
    • 200 Ashley Ln, Chestertown, MD 21620
      200 Ashley Ln, Chestertown, MD 21620
      200 Ashley Ln, Chestertown, MD 21620
      /37

      Est $446,520 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,656 Sq Ft

      200 Ashley Ln, Chestertown, MD 21620

      200 Ashley Ln, Chestertown, MD 21620
  • 134 Char Nor Manor Blvd, Chestertown, MD 21620
    134 Char Nor Manor Blvd, Chestertown, MD 21620
    134 Char Nor Manor Blvd, Chestertown, MD 21620
    /42

    $325,000

    • 3 Beds
    • 1 Bath
    • 1,128 Sq Ft

    134 Char Nor Manor Blvd, Chestertown, MD 21620

    Chester River Charm: Your Gateway toEastern Shore LivingCompletely Renovated Cottage with River Views & Endless PossibilitiesDiscover the perfect blend of modern comfort and Eastern Shore tranquility at this beautifullytransformed 3-bedroom, 1-bath cottage just minutes from historic Chestertown and the pristineChester River. Whether you're seeking a weekend escape, investment

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (667) 282-1137

    134 Char Nor Manor Blvd, Chestertown, MD 21620
  • 107 Dutchess Rd, Chestertown, MD 21620
    107 Dutchess Rd, Chestertown, MD 21620
    107 Dutchess Rd, Chestertown, MD 21620
    /23

    $290,000 Sold Aug 13, 2025

    • 1,380 Sq Ft
    • $210/SF
    • 234 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2005

    107 Dutchess Rd, Chestertown, MD 21620

    Welcome to Chester Harbor - a family oriented place to live! The Chester Harbor Community has a voluntary HOA of $30/year, which offers water access, a beach, community events, and a playground. Close by is Round Top Park offering tennis, pickleball, and basketball courts, a playground, and a pavilion. Minutes from Chestertown's historic waterfront, restaurants, shopping, and marinas. Queen

    Jo Ann Edwards The Hogans Agency

    107 Dutchess Rd, Chestertown, MD 21620
    • 218 Camelot Dr, Chestertown, MD 21620
      218 Camelot Dr, Chestertown, MD 21620
      218 Camelot Dr, Chestertown, MD 21620
      /44

      Est $504,754 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,932 Sq Ft

      218 Camelot Dr, Chestertown, MD 21620

      218 Camelot Dr, Chestertown, MD 21620

Showing Results 1 - 40, Page 1 of 18

Maryland Kent County Chestertown

Real Estate & Homes

Home Trends in Chestertown, MD

On average, homes in Chestertown, MD sell after 54 days on the market compared to the national average of 52 days. The median sale price for homes in Chestertown, MD over the last 12 months is $355,000, up 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$355,000
Median Single Family Sale Price
$380,000
Median Townhouse Sale Price
$283,000
Median 2 Bedroom Sale Price
$482,000
Median 1 Bedroom Sale Price
$285,000
Average Price Per Sq Ft
$218
Number of Homes for Sale
34
Last 12 months Home Sales
89
Months of Supply
4.60
Median List Price
$369,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%
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