188

Recently Sold Chestertown, MD Homes

Section Image
  • 8605 Camp Rd, Chestertown, MD 21620
    8605 Camp Rd, Chestertown, MD 21620
    8605 Camp Rd, Chestertown, MD 21620
    /51

    $370,000 Sold May 08, 2025

    • 1,296 Sq Ft
    • $285/SF
    • 10 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1968

    8605 Camp Rd, Chestertown, MD 21620

    Your home sweet home retreat - a gorgeous 3 Bedroom 2 Full Bathroom Rancher with attached carport and unfinished basement is available to tour! Major renovations in 2020 and maintained to pristine condition. If you are looking for a place to come home and relax - this is the one! Sit on the front porch and enjoy the afternoon sun, calm surroundings or listen to the birds actively chirping. Head

    Crystal Smith RE/MAX Executive

    8605 Camp Rd, Chestertown, MD 21620
  • 202 Glen St, Chestertown, MD 21620
    202 Glen St, Chestertown, MD 21620
    202 Glen St, Chestertown, MD 21620
    /37

    $290,000 Sold May 08, 2025

    • 1,252 Sq Ft
    • $232/SF
    • 104 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1966

    202 Glen St, Chestertown, MD 21620

    Brick rancher located on the corner of Greenwood and Glen Street in College Heights offers a large screened porch, eat-in kitchen and dining room. Home is convenient to downtown historic Chestertown , Washington College and hospital. Property is served with public water/sewer. Underground oil tank has been removed and the crawlspace is encapsulated.

    Debbie Meikle Doug Ashley Realtors, LLC

    202 Glen St, Chestertown, MD 21620
  • 116 Oak Leaf Dr, Chestertown, MD 21620
    116 Oak Leaf Dr, Chestertown, MD 21620
    116 Oak Leaf Dr, 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
  • 118 Char Nor Manor Blvd, Chestertown, MD 21620
    118 Char Nor Manor Blvd, Chestertown, MD 21620
    118 Char Nor Manor Blvd, 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
  • 107 Chester Arms Dr, Chestertown, MD 21620
    107 Chester Arms Dr, Chestertown, MD 21620
    107 Chester Arms Dr, 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
  • 123 Burchard Sawmill Rd, Chestertown, MD 21620
    123 Burchard Sawmill Rd, Chestertown, MD 21620
    123 Burchard Sawmill 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
  • 123 Burchard Sawmill Rd, Chestertown, MD 21620
    123 Burchard Sawmill Rd, Chestertown, MD 21620
    123 Burchard Sawmill 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
  • 505 N Kent St, Chestertown, MD 21620
    505 N Kent St, Chestertown, MD 21620
    505 N Kent St, 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
  • 113 Pine Cove Ln, Chestertown, MD 21620
    113 Pine Cove Ln, 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
  • 720 Aldora Dr Unit 109, Chestertown, MD 21620
    720 Aldora Dr Unit 109, Chestertown, MD 21620
    720 Aldora Dr Unit 109, Chestertown, MD 21620
    /35

    $479,495 Sold Apr 25, 2025

    • 2,120 Sq Ft
    • $226/SF
    • 0 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2025

    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 and

    Terri Hill Builder Solutions Realty

    720 Aldora Dr Unit 109, Chestertown, MD 21620
  • 3650 Gratitude Way, Chestertown, MD 21620
    3650 Gratitude Way, Chestertown, MD 21620
    3650 Gratitude Way, 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, INC.

    3650 Gratitude Way, Chestertown, MD 21620
  • 130 Sheaffer Rd, Chestertown, MD 21620
    130 Sheaffer Rd, Chestertown, MD 21620
    130 Sheaffer Rd, 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
  • 7938 Radcliffe Rd, Chestertown, MD 21620
    7938 Radcliffe Rd, Chestertown, MD 21620
    7938 Radcliffe Rd, 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
  • 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

    • 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
  • 21313 Persimmon Dr Unit 24, Chestertown, MD 21620
    21313 Persimmon Dr Unit 24, Chestertown, MD 21620
    21313 Persimmon Dr Unit 24, 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
  • 149 Longfellow Dr, Chestertown, MD 21620
    149 Longfellow Dr, Chestertown, MD 21620
    149 Longfellow Dr, Chestertown, MD 21620
    /25

    $385,000 Sold Apr 11, 2025

    • 1,811 Sq Ft
    • $213/SF
    • 19 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1982

    149 Longfellow Dr, Chestertown, MD 21620

    Welcome to your dream home in the charming sought after community of Chester Harbor! This delightful property boasts 3 spacious bedrooms and 2 full updated bathrooms, perfectly designed for comfort and modern living.Step into the huge master bedroom, perfect for all buyers. The finished basement provides versatile additional living space—ideal for a family room, home office, or play area.The

    Isaac Bahary KW Empower

    149 Longfellow Dr, Chestertown, MD 21620
  • 473 Pear Tree Point Rd, Chestertown, MD 21620
    473 Pear Tree Point Rd, Chestertown, MD 21620
    473 Pear Tree Point Rd, Chestertown, MD 21620
    /24

    $359,900 Sold Apr 11, 2025

    • 1,512 Sq Ft
    • $238/SF
    • 67 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2024

    473 Pear Tree Point Rd, Chestertown, MD 21620

    Come By this brand new Cape Cod nestled in charming Pear Tree Point! This 3-bedroom, 3-bathroom haven offers the tranquility of coastal living with the ease of new construction. Step inside and discover the warmth of this open floor plan luxury vinyl plank flooring flowing throughout the main level. Unwind in the light-filled living area, perfect for entertaining, or retreat to the inviting

    David Moore RE/MAX Executive

    473 Pear Tree Point Rd, Chestertown, MD 21620
  • 234 Blakefield Dr, Chestertown, MD 21620
    234 Blakefield Dr, Chestertown, MD 21620
    234 Blakefield Dr, Chestertown, MD 21620
    /3

    $553,500 Sold Apr 07, 2025

    • 2,400 Sq Ft
    • $231/SF
    • 0 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2024

    234 Blakefield Dr, Chestertown, MD 21620

    3 BEDROOM, 2.5 BTHROOM NEW CONSTRUCTION TO START. FINISHED BONUS ROOM. FULL UNFINISHED BASEMENT. APROX 2400 SF.

    Chris Haddaway Chesapeake Real Estate Associates, LLC

    234 Blakefield Dr, Chestertown, MD 21620
  • 109 Secor Rd, Chestertown, MD 21620
    109 Secor Rd, Chestertown, MD 21620
    109 Secor Rd, Chestertown, MD 21620
    /41

    $385,000 Sold Apr 04, 2025

    • 1,560 Sq Ft
    • $247/SF
    • 69 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1977

    109 Secor Rd, Chestertown, MD 21620

    Charming Home in Chester Harbor with Water Access!Welcome to 109 Secor Rd, Chestertown, MD 21620, nestled on a peaceful cul-de-sac in the desirable water-access community of Chester Harbor on the Queen Anne’s side of the Chester River. This home offers a perfect blend of comfort, charm, and recent updates, making it an exceptional choice for your next chapter.Key

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    109 Secor Rd, Chestertown, MD 21620
  • 220 Blakefield Dr, Chestertown, MD 21620
    220 Blakefield Dr, Chestertown, MD 21620
    220 Blakefield Dr, Chestertown, MD 21620
    /46

    $474,000 Sold Apr 03, 2025

    • 1,900 Sq Ft
    • $249/SF
    • 84 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2024

    220 Blakefield Dr, Chestertown, MD 21620

    Brand New Gorgeous Custom Home completed & ready for a family to start their next adventure. Fall in love with the 1st floor bedroom/bath/WIC, 2 car garage, gourmet kitchen with large island & granite counters, cathedral ceilings, huge family room, 1st floor laundry, front porch, sky-basement on 2nd floor for storage, 2 large bedrooms and full bath on second floor. This great floor plan is hard

    Brenda Fornos Taylor Properties

    220 Blakefield Dr, Chestertown, MD 21620
  • 10640 Watonga Rd, Chestertown, MD 21620
    10640 Watonga Rd, Chestertown, MD 21620
    10640 Watonga Rd, Chestertown, MD 21620
    /31

    $305,000 Sold Apr 01, 2025

    • 1,196 Sq Ft
    • $255/SF
    • 2 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1995

    10640 Watonga Rd, Chestertown, MD 21620

    Located in Chesapeake Landing, this property offers access to a community area with a boat launch and docks, available through membership in the very reasonable community association. The deck overlooks a semi-private backyard. Inside, the house features new carpeting and fresh paint. It offers single-level living with three bedrooms, two full baths, and a kitchen/dining area with a sliding door

    Retha Arrabal Doug Ashley Realtors, LLC

    10640 Watonga Rd, Chestertown, MD 21620
  • 105 Justin Buch Dr, Chestertown, MD 21620
    105 Justin Buch Dr, Chestertown, MD 21620
    105 Justin Buch Dr, Chestertown, MD 21620
    /39

    $355,000 Sold Mar 31, 2025

    • 1,200 Sq Ft
    • $296/SF
    • 19 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1991

    105 Justin Buch Dr, Chestertown, MD 21620

    Welcome to 105 Justin Buch Drive, a delightful single-family home nestled in a quiet community on the Queen Anne's side of Chestertown, MD. This charming residence offers 3 spacious bedrooms and 2 full bathrooms, providing ample space for comfortable living. Buy with ease with this recently renovated home within the last 3 years, to include a new roof, HVAC, Kitchen backsplash, new garage

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    105 Justin Buch Dr, Chestertown, MD 21620
  • 201 Fairview Dr, Chestertown, MD 21620
    201 Fairview Dr, Chestertown, MD 21620
    201 Fairview Dr, Chestertown, MD 21620
    /22

    $319,000 Sold Mar 31, 2025

    • 1,188 Sq Ft
    • $269/SF
    • 49 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1985

    201 Fairview Dr, Chestertown, MD 21620

    Welcome to Chester Harbor. Great starter or downsizer, 3 bed 2 bath rancher awaits new owners. The floor plan includes generous Eat -in kitchen and large living room, separate laundry, and a huge screened in porch for picking crabs, parties, or just relaxing. New flooring , fresh paint, and new kitchen counters are a few of the recent updates. Tree lined rear yard and front holly hedge

    Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

    201 Fairview Dr, Chestertown, MD 21620
  • Lot 4 Muirfield Dr, Chestertown, MD 21620
    Lot 4 Muirfield Dr, Chestertown, MD 21620
    Lot 4 Muirfield Dr, Chestertown, MD 21620
    /22

    $155,200 Sold Mar 31, 2025

    • Land
    • 1.90 Acres
    • $81,684 per Acre
    • 300 Days On Market

    Lot 4 Muirfield Dr, Chestertown, MD 21620

    Location (3 fairway lots available), Location (minutes from historic Chestertown), Location (easy access to pristine waterways of Maryland s eastern shore). Two other interior lots available including two corner locations. Lot 4 overlooks two greens on on hole #10 the other on # 5 with fairway boarders on two sides. Prestwick offers the best in eastern shore living with the small town charm of

    John Burke Gunther-McClary Real Estate

    Lot 4 Muirfield Dr, Chestertown, MD 21620
  • 117 Court St, Chestertown, MD 21620
    117 Court St, Chestertown, MD 21620
    117 Court St, Chestertown, MD 21620
    /35

    $365,000 Sold Mar 28, 2025

    • 744 Sq Ft
    • $491/SF
    • 23 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1885

    117 Court St, Chestertown, MD 21620

    Truly fine example of Italianate architecture nestled among Lawyer's Row in Historic District of Chestertown, Maryland. Immerse oneself in the lifestyle of an Historic Eastern Shore Town on the "beautiful" - as so any describe - Chester River. Home of 18th & 19th c. residences, charming shops, strong Arts & Craft Community, live theater and 10th oldest college in America - Washington College.

    Nancy McGuire Maryland Heritage Properties

    117 Court St, 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

    • 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
  • 6744 Church Hill Rd, Chestertown, MD 21620
    6744 Church Hill Rd, Chestertown, MD 21620
    6744 Church Hill Rd, Chestertown, MD 21620
    /41

    $320,000 Sold Mar 26, 2025

    • 1,298 Sq Ft
    • $247/SF
    • 199 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1964

    6744 Church Hill Rd, Chestertown, MD 21620

    Nestled in a prime suburban commercial zone, this versatile property offers 1,300 sq ft of living space, perfect for both residential and/or commercial use. The freshly resealed driveway accommodates up to 6+ vehicles, with the potential for parking lot expansion, ensuring ample space for guests or clients. The property features two inviting front entries: one through an 8x16 sunporch, ideal for

    Sarah Ulrick Rock Hall Properties Real Estate

    6744 Church Hill Rd, Chestertown, MD 21620
  • 9048 Georgetown Rd, Chestertown, MD 21620
    9048 Georgetown 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
  • 225 S Water St Unit 6, Chestertown, MD 21620
    225 S Water St Unit 6, Chestertown, MD 21620
    225 S Water St Unit 6, Chestertown, MD 21620
    /56

    $965,500 Sold Mar 21, 2025

    • 2,800 Sq Ft
    • $345/SF
    • 14 Days On Market
    • 3 Beds
    • 3.5 Baths
    • Built 2006

    225 S Water St Unit 6, Chestertown, MD 21620

    This end unit waterfront condo in Scott's Point has beautiful water views up and down the Chester River! It is a light filled gem with water views from every window. It has been impeccably maintained and offers wood floors, fireplace, plantation shutters, gourmet kitchen, front and back porches, second and third floor balconies and much more. There are two deeded slips (4ft. MLW) at the community

    Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    225 S Water St Unit 6, Chestertown, MD 21620
  • 477 Pear Tree Point Rd, Chestertown, MD 21620
    477 Pear Tree Point Rd, Chestertown, MD 21620
    477 Pear Tree Point Rd, Chestertown, MD 21620
    /20

    $355,000 Sold Mar 21, 2025

    • 1,512 Sq Ft
    • $235/SF
    • 282 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2024

    477 Pear Tree Point Rd, Chestertown, MD 21620

    Price Reduced!! Brand NEW home located within the much desired Queen Anne's County School District!! Three (3) bedrooms and Two and a half (2.5) baths. Water views of the Chester River and an open-concept layout. Stainless steel appliances in the kitchen, a main-level master suite with a walk-in closet. Upstairs, you'll find two more generously sized bedrooms and an additional full bathroom. High

    Clint Evans Cross Street Realtors LLC

    477 Pear Tree Point Rd, Chestertown, MD 21620
  • 3652 Gratitude Way, Chestertown, MD 21620
    3652 Gratitude Way, Chestertown, MD 21620
    3652 Gratitude Way, Chestertown, MD 21620
    /10

    $579,238 Sold Mar 20, 2025

    • 2,642 Sq Ft
    • $219/SF
    • 1 Day On Market
    • 4 Beds
    • 3 Baths
    • Built 2025

    3652 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, INC.

    3652 Gratitude Way, Chestertown, MD 21620
  • 116 Island Lark Way, Chestertown, MD 21620
    116 Island Lark Way, Chestertown, MD 21620
    116 Island Lark Way, Chestertown, MD 21620
    /20

    $286,900 Sold Mar 17, 2025

    • 1,420 Sq Ft
    • $202/SF
    • 125 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2023

    116 Island Lark Way, Chestertown, MD 21620

    Welcome home to this beautiful end unit townhome in the newer community of The Village At Chestertown. This 3 bedroom, 2.5 bath townhome looks out over the beautiful pond with fountain, and a great walking path around the pond and community. Furry friends are welcome at the nearby dog park as well. This home is less than a year old and has had some upgrades added since the purchase, such as

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    116 Island Lark Way, Chestertown, MD 21620
  • 409 Riverview Rd, Chestertown, MD 21620
    409 Riverview Rd, Chestertown, MD 21620
    409 Riverview Rd, Chestertown, MD 21620
    /29

    $380,000 Sold Mar 14, 2025

    • 1,800 Sq Ft
    • $211/SF
    • 118 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1998

    409 Riverview Rd, Chestertown, MD 21620

    EXCEPTIONAL VALUE-This charming Cape Cod home offers exceptional value with a recent $10,000 price reduction and new carpet throughout. Located on a desirable corner lot in Kingstown, this property is just a short walk or bike ride from historic Chestertown. The home features a modernized kitchen, updated bathrooms, and custom tile floors. Enjoy the convenience of a first-floor bedroom, a

    Norma Coursey Benson & Mangold, LLC

    409 Riverview Rd, Chestertown, MD 21620
  • 209 N Queen St, Chestertown, MD 21620
    209 N Queen St, Chestertown, MD 21620
    209 N Queen St, Chestertown, MD 21620
    /63

    $535,000 Sold Mar 13, 2025

    • 2,328 Sq Ft
    • $230/SF
    • 10 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1885

    209 N Queen St, Chestertown, MD 21620

    Welcome to the historic Fannie Stuart home, c 1885 - a delightful Victorian home, with the perfect blend of classic elegance and modern comfort, blocks to downtown historic Chestertown and all it has to offer. This special residence boasts four spacious bedrooms, and two beautifully renovated bathrooms, offering ample space for relaxation and entertaining. Step inside to discover a warm and

    Andrea Alderdice Long & Foster Real Estate, Inc.

    209 N Queen St, Chestertown, MD 21620
  • 312 Princess Anne Dr, Chestertown, MD 21620
    312 Princess Anne Dr, Chestertown, MD 21620
    312 Princess Anne Dr, Chestertown, MD 21620
    /87

    $440,000 Sold Mar 13, 2025

    • 1,848 Sq Ft
    • $238/SF
    • 31 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1987

    312 Princess Anne Dr, Chestertown, MD 21620

    ?? Just Renovated Creekside Beauty – Move-In Ready! ??Discover your dream home with this beautifully renovated 4-bedroom, 2.5-bath gem that overlooks a serene creek. Perfectly blending modern upgrades with cozy charm, this property has everything you need and more!? Key Features:Spacious 2-Car GarageBonus Room: Use as a 4th bedroom, home office, or entertainment

    Jim Davidson Coldwell Banker Waterman Realty

    312 Princess Anne Dr, Chestertown, MD 21620
  • 204 Pine Cove Ln, Chestertown, MD 21620
    204 Pine Cove Ln, Chestertown, MD 21620
    204 Pine Cove Ln, Chestertown, MD 21620
    /30

    $400,000 Sold Mar 12, 2025

    • 2,167 Sq Ft
    • $185/SF
    • 19 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2021

    204 Pine Cove Ln, Chestertown, MD 21620

    Discover the perfect blend of modern design and rustic charm at 204 Pine Cove Lane, a stunning 3-bedroom, 2.5-bathroom home built in 2021. Tucked away on a secluded lot and surrounded by picturesque farmland, this property offers unparalleled privacy and tranquility—a true sanctuary for those seeking a peaceful retreat.Step inside to be greeted by a thoughtfully designed interior,

    Kelly Harris Coldwell Banker Realty

    204 Pine Cove Ln, Chestertown, MD 21620
  • 317 Union Church Rd, Chestertown, MD 21620
    317 Union Church Rd, Chestertown, MD 21620
    317 Union Church Rd, Chestertown, MD 21620
    /33

    $685,000 Sold Mar 07, 2025

    • 2,512 Sq Ft
    • $273/SF
    • 0 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2021

    317 Union Church Rd, Chestertown, MD 21620

    Welcome to 317 Union Church Rd, Stunning Custom Built Farmhouse with all the bells and whistles perfectly sited on over 1 acre. Open concept yet defined spaces allow this home to function wonderfully for entertaining and everyday living...The home exudes style and hospitality from its covered wraparound plantation porch through to the welcoming extra wide entry, seamlessly flowing to the

    Karen Clark Clark & Co Realty, LLC

    317 Union Church Rd, Chestertown, MD 21620
  • 10061 Flatland Rd, Chestertown, MD 21620
    10061 Flatland Rd, Chestertown, MD 21620
    10061 Flatland Rd, Chestertown, MD 21620
    /21

    $325,000 Sold Mar 06, 2025

    • 2,376 Sq Ft
    • $137/SF
    • 18 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1969

    10061 Flatland Rd, Chestertown, MD 21620

    Charming, very well-maintained home located just outside historic Chestertown. The side entrance has a spacious deck and ramp that leads to a full blacktop driveway. Unique split level back entrance. 1.3 grassy acres. Large unfinished basement for extra living space. Hardwood flooring beneath the carpet. Updates include recent paint in interior rooms, (except Kitchen), new paint basement,

    Jo Ann Edwards The Hogans Agency

    10061 Flatland Rd, Chestertown, MD 21620
  • 23110 Old Fairlee Rd, Chestertown, MD 21620
    23110 Old Fairlee Rd, Chestertown, MD 21620
    23110 Old Fairlee Rd, Chestertown, MD 21620
    /21

    $165,300 Sold Mar 05, 2025

    • 1,545 Sq Ft
    • $107/SF
    • 129 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1938

    23110 Old Fairlee Rd, Chestertown, MD 21620

    Welcome to this lovely home with a detached garage in the community of Woods Edge in Kent County! The home features three spacious bedrooms with built-in closets, a full bath with dual vanities and a soaking tub, a family room with a fireplace that opens to the kitchen with appliances and wooden cabinets, and a sunroom with tiled floors and a sliding door that leads to the backyard. The home is

    Gina Gargeu Century 21 Downtown

    23110 Old Fairlee Rd, 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

    • 1,872 Sq Ft
    • $190/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1995

    10724 Foreston Rd, Chestertown, MD 21620

    Your dream home is waiting! This remodeled home is waiting for you in the serene water-privileged community of Chesapeake Landing, just minutes from downtown Chestertown. The community offers exclusive access to a boat ramp, a small marina with boat slips, picnic area, and picturesque walking trails. This inviting 3-bedroom, 2-bath residence offers an ideal blend of comfort, convenience, and

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    10724 Foreston Rd, Chestertown, MD 21620

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