7,032

Homes in ZIP Code 21620

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  • /20

    $212,000

    • Land
    • 1.95 Acres
    • $108,718 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
  • /15

    $2,200 per month

    • 3 Beds
    • 1 Bath
    • 1,900 Sq Ft
    • Condo for Rent

    321 High St Unit 1, Chestertown, MD 21620

    Property Id: 1403856Huge 3br, 1 bath, with office and extra storage in the middle of downtown Chestertown. Full of charm, with wood floors and a claw foot tub, this apartment offers a front seat view to everything happening in Chestertown, with downtown shops and restaurants just steps away. Recently renovated with many energy improvements, such as new insulation and windows. Updated

    321 High St Unit 1, Chestertown, MD 21620
  • /38

    $289,500 Sold May 05, 2025

    • 1,867 Sq Ft
    • $155/SF
    • 13 Days On Market
    • 2 Beds
    • 4 Baths
    • Built 2004

    116 Oak Leaf Dr, Chestertown, MD 21620

    Charming & Move-In ReadyDiscover this beautifully maintained end-unit townhome just minutes from downtown Chestertown! This home has been loved and cared for by the original owners. Offering updated hardwood flooring, carpeting on stairs, fresh paint in the primary living space, a new roof, this ensuring peace of mind for years to come.The spacious master suite features vaulted ceilings, a stall

    Grace Crockett Doug Ashley Realtors, LLC

    116 Oak Leaf Dr, Chestertown, MD 21620
    • /27

      Est $359,577 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
  • /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
  • /19

    $1,900 per month

    • 2 Beds
    • 1 Bath
    • 1,455 Sq Ft
    • House for Rent

    128 N Queen St, Chestertown, MD 21620

    Welcome to 128 N Queen Street, Unit 2. A beautiful Victorian apartment located downtown Chestertown within walking distance to the Chester River and situated close to the Washington College. Downstairs features a large living area, formal living/dining room that could be used as a 3rd bedroom, open kitchen/dining area with laundry. Tenant would have private access to 2 of the three porches.

    Amanda Morgan Brenton Realty Group

    128 N Queen St, Chestertown, MD 21620
  • /34

    $265,000 Sold May 02, 2025

    • 1,114 Sq Ft
    • $238/SF
    • 120 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1965

    118 Char Nor Manor Blvd, Chestertown, MD 21620

    An adorable cottage with water views of the Chester River! Nicely maintained cottage featuring 3 bedrooms, 2 full baths with all the big ticket items completed. Newer Well and Septic, HVAC and newer Metal Roof just leaves you with finishing touches on the interior as you see fit. Currently used as a rental. Also features a detached workshop and detached garage. If you are a boater, bring your

    Rylie Patrick Chesapeake Real Estate Associates, LLC

    118 Char Nor Manor Blvd, Chestertown, MD 21620
    • /30

      Est $455,956 Not Listed For Sale

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

      148 Grant Ct, Chestertown, MD 21620

      148 Grant Ct, Chestertown, MD 21620
  • /24

    $299,900

    • 1 Bed
    • 1 Bath
    • 652 Sq Ft

    117 N Water St Unit 3B, Chestertown, MD 21620

    A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 453-1375

    117 N Water St Unit 3B, Chestertown, MD 21620
  • /14

    $1,000 per month

    • Studio
    • 1 Bath
    • 300 Sq Ft
    • Condo for Rent

    425 High St Unit 4, Chestertown, MD 21620

    Property Id: 1770574Studio apartment in walking distance to Washington College and downtown Chestertown. Second floor studio apartment in recently renovated building. Updated insulation, modern windows and HVAC with original features, such as wood floors. In-building laundry and shared yard for tenants' use. Available early June. Landlord requires a minimum 650 credit score and month

    425 High St Unit 4, Chestertown, MD 21620
  • /19

    $230,000 Sold May 01, 2025

    • 1,140 Sq Ft
    • $202/SF
    • 14 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2022

    107 Chester Arms Dr, Chestertown, MD 21620

    Why rent when you can own for less?!?! Three beds, 2 baths!! This inviting one-level home offers easy one-level living. Featuring luxury vinyl plank flooring , a stylish open kitchen and granite countertops, and a cozy eat-in area that opens to the living room, this home feels very welcoming. The comfortable primary suite features a full bath, while two additional bedrooms provide flexibility

    Casey Scattergood Cross Street Realtors LLC

    107 Chester Arms Dr, Chestertown, MD 21620
    • /17

      Est $255,673 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths

      104 Metcalf Rd, Chestertown, MD 21620

      104 Metcalf Rd, Chestertown, MD 21620
  • /32

    $789,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 2,204 Sq Ft

    308 Landing Ln, Chestertown, MD 21620

    Exceptional Chester River Landing townhome with elevated views of the Chester River. Enjoy sunrises over the Chester from the balcony and living space. Beautiful views any time of year. A deep water boat slip is included in the sale. The living room offers, cozy gas fireplace, has beautiful water views all year. This condo boast an open floor plan with tons of natural light, ample room for

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 779-9803

    308 Landing Ln, 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
  • /53

    $485,000 Sold May 01, 2025

    • 1,648 Sq Ft
    • $294/SF
    • 4 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1918

    123 Burchard Sawmill Rd, Chestertown, MD 21620

    This is it! This is the one you and your horse have been dreaming about! Absolutely darling 4+ acre farmette! Charm charm charm plus function function function. Turnkey and ready for your horses, your ponies or your 4-H projects, or all of the above! Built in 1918, this 3 Bedroom American Folk merges vernacular farmhouse (winder staircase, built-in corner cupboard, beautiful curved plaster wall)

    Crystal Pickett EXP Realty, LLC

    123 Burchard Sawmill Rd, Chestertown, MD 21620
    • /16

      Est $382,798 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
  • /5

    $292,900

    • 2 Beds
    • 1 Bath
    • 2,142 Sq Ft

    10141 Flatland Rd, Chestertown, MD 21620

    Farmhouse located on two acre cleared lot that overlooks farmland. Improvements have been made to the property, including a metal farm/garage/workshop building with electric and three garage doors. There is a shed that improvements have started on, but not complete. Property has two bedrooms and one bath, with a traditional floor plan typical for a farmhouse style home. The kitchen is in

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 618-9426

    10141 Flatland Rd, Chestertown, MD 21620
  • /23

    $352,500 Sold Apr 30, 2025

    • 1,402 Sq Ft
    • $251/SF
    • 9 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1985

    505 N Kent St, Chestertown, MD 21620

    Charming Rancher in Sought-After Byford Development!Nestled in the desirable Byford Development of Chestertown, this 1,402 sq. ft. rancher sits on a spacious 1/3-acre lot offering comfort, convenience, and opportunity! Featuring 3 bedrooms and 2 full baths, this one-level home boasts a primary suite with double sinks and an oversized shower, as well as a bright enclosed Florida room with vaulted

    Sarah Ulrick Rock Hall Properties Real Estate

    505 N Kent St, Chestertown, MD 21620
    • /34

      Est $261,260 Not Listed For Sale

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

      7499 Poplar Ave, Chestertown, MD 21620

      7499 Poplar Ave, Chestertown, MD 21620
  • /61

    $1,799,000 Open House 5/31

    • 3 Beds
    • 3.5 Baths
    • 4,547 Sq Ft

    21082 Wyoming Ave, Chestertown, MD 21620

    Charming Chesapeake Bay Home with Stunning Water Views and Incredible Sunsets! TAX INFO has SQUARE FOOTAGE INCORRECT. Living space is 2599 and the unfinished basement is 1948Discover the beauty of waterfront living in this exquisite home featuring panoramic views of the Chesapeake Bay. Having undergone a comprehensive renovation in 2022-2023, this property continues to impress with ongoing

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 883-5429

    21082 Wyoming Ave, Chestertown, MD 21620
  • /2

    $57,500 Sold Apr 30, 2025

    • Land
    • 0.45 Acre
    • $127,778 per Acre
    • 185 Days On Market

    113 Pine Cove Ln, Chestertown, MD 21620

    Wonderful opportunity to purchase two established adjoining residential lots within a short walking distance to the Chester River and deep water boat ramp. These two recorded lots were purchased many years ago by a family that vacationed in a home nearby. These lots have not been perc tested but the soil types are conducive to percing and there are homes on the neighboring parcels. Please

    William Norris Select Land & Homes, LLC

    113 Pine Cove Ln, Chestertown, MD 21620
    • /63

      Est $363,886 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
  • /45

    $320,000 Open Sat 9:30AM - 11AM

    • 3 Beds
    • 1 Bath
    • 1,104 Sq Ft

    24095 Chestertown Rd, Chestertown, MD 21620

    This gem just outside of Chestertown will be active mid-April. New HVAC, new roof, new flooring and other upgrades! Great living space with a front porch and back patio. Large backyard that overlooks beautiful farm fields. There is a one car detached insulated garage. This home offers close proximity to Rock Hall and all downtown Chestertown amenities, schools, and parks and is only 25 minutes

    Agent Photo

    Lona Todd

    Taylor Properties

    (410) 724-1462

    24095 Chestertown Rd, Chestertown, MD 21620
  • /18

    $636,383 Sold Apr 24, 2025

    • 3,599 Sq Ft
    • $177/SF
    • 1 Day On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2025

    3650 Gratitude Way, Chestertown, MD 21620

    TO BE BUILT......Welcome to Ryan Homes at Gilbert Meadows. Offering ranch style & 2-story single family homes with 1st floor primary suites in Harford County, MD. Minutes to Rte. 22 & I-95 - Starting from the low $500's. Our homes are designed to make your life easier with open and modern designs connecting all the spaces you use most! Plus, our homes all offer all the conveniences of main-level

    Tineshia Johnson NVR Services, Inc.

    3650 Gratitude Way, Chestertown, MD 21620
    • /56

      Est $357,061 Not Listed For Sale

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

      10570 Cogar Rd, Chestertown, MD 21620

      10570 Cogar Rd, Chestertown, MD 21620
  • /41

    $579,000

    • 2 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    103 Landing Ln, Chestertown, MD 21620

    Step into this nearly new, impeccably maintained two-bedroom townhouse located in the highly desirable Chester River Landing community. Recent upgrades make this home truly turn-key, perfect for those seeking comfort and style. Relax and entertain all summer long on the beautifully designed screened-in porch, ideal for enjoying warm evenings and gentle breezes.On the second floor, the spacious

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 981-2534

    103 Landing Ln, Chestertown, MD 21620
  • /25

    $431,000 Sold Apr 22, 2025

    • 1,766 Sq Ft
    • $244/SF
    • 1 Day On Market
    • 4 Beds
    • 2 Baths
    • Built 1999

    130 Sheaffer Rd, Chestertown, MD 21620

    Welcome to The Grove in Chestertown, a picturesque location in Queen Anne's county, located just a short drive from Chesapeake College and historic Chestertown.130 Sheaffer Road offers peaceful living on over an acre of land with highlights such as main level bedrooms, an expansive fenced in backyard, two car garage, large shed for additional storage, and more! As you enter through the front

    Biana Arentz Coldwell Banker Realty

    130 Sheaffer Rd, Chestertown, MD 21620
    • /9

      Est $445,280 Not Listed For Sale

      • 3 Beds
      • 2 Baths

      209 Blakefield Dr, Chestertown, MD 21620

      209 Blakefield Dr, 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
  • /44

    $560,000 Sold Apr 21, 2025

    • 2,408 Sq Ft
    • $233/SF
    • 115 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1976

    7938 Radcliffe Rd, Chestertown, MD 21620

    This impeccably maintained home is a true standout and has it ALL! With 5 spacious bedrooms - with both main level & upper level primary suites - and 3.5 baths, including a main level primary suite with a walk-in closet featuring a premium wood built-in system, dual vanity, and a double-headed walk-in tiled shower. This home offers both luxury and convenience. The updated kitchen is an ideal

    Liddy Campbell TTR Sotheby's International Realty

    7938 Radcliffe Rd, Chestertown, MD 21620
    • /11

      Est $339,570 Not Listed For Sale

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

      221 Central Dr, Chestertown, MD 21620

      221 Central Dr, Chestertown, MD 21620
  • /23

    $950,000 New Construction

    • 3 Beds
    • 3.5 Baths

    228 S Water St, Chestertown, MD 21620

    Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away.

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 230-5332

    228 S Water St, Chestertown, MD 21620
  • /36

    $424,900 Sold Apr 18, 2025

    • 1,680 Sq Ft
    • $253/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2025

    206 Springbrook Ln, Millington, MD 21651

    The new construction home you have been waiting for featuring all the builder upgrades! Don't miss out on this opportunity to buy brand new on a 1 plus acre lot for under 425k in QA County, situated on 1.035 private wooded acres this home features an amazing open floor plan with 3 bedrooms and 2 full baths. This home provides ample storage and closest space, including a walk-in pantry, custom

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    206 Springbrook Ln, Millington, MD 21651
    • /25

      Est $412,416 Not Listed For Sale

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

      1213 Ewingtown Rd, Chestertown, MD 21620

      1213 Ewingtown Rd, Chestertown, MD 21620
  • /35

    $424,990 Pending

    • 4 Beds
    • 3.5 Baths
    • 2,120 Sq Ft

    720 Aldora Dr Unit 109, Chestertown, MD 21620

    DECORATED MODELS NOW OPEN Luxury 3 Bedroom Villas The layout is welcoming and very functional. Featuring a huge family room, dining area and stunning kitchen. The second floor boasts 3 bedrooms with an owner's suite that includes 2 walk-in closets and private bath which boasts ceramic tile, a double bowl sink, private water closet and seated shower., and an additional bath for family

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (410) 826-6312

    720 Aldora Dr Unit 109, 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 in the

    Retha Arrabal Doug Ashley Realtors, LLC

    25740 Collins Ave, Chestertown, MD 21620
    • /37

      Est $434,700 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
  • /35

    $500,799 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 2,120 Sq Ft

    716 Aldora Dr, Chestertown, MD 21620

    DECORATED MODELS NOW OPEN Luxury 3 Bedroom Villas The layout is welcoming and very functional. Featuring a huge family room, dining area and stunning kitchen. The second floor boasts 3 bedrooms with an owner's suite that includes 2 walk-in closets and private bath which boasts ceramic tile, a double bowl sink, private water closet and seated shower., and an additional bath for family

    Agent Photo

    Terri Hill

    Builder Solutions Realty

    (443) 727-1909

    716 Aldora Dr, Chestertown, MD 21620
  • /16

    $195,000 Sold Apr 11, 2025

    • 1,350 Sq Ft
    • $144/SF
    • 0 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1955

    21313 Persimmon Dr Unit 24, Chestertown, MD 21620

    This property is in great condition, with a nice kitchen, a living/dining room combo on the main level, a utility room and plenty of storage space. The living room has a slider out to the patio, and there is a storage shed there for outdoor storage. This is an end unit in great condition. Upstairs there are three bedrooms and a full bath. Nice light from windows and indoor lighting.

    Retha Arrabal Doug Ashley Realtors, LLC

    21313 Persimmon Dr Unit 24, Chestertown, MD 21620
    • /44

      Est $513,318 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

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