7,034

Homes in ZIP Code 21620

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  • /37

    $600,000 Sold Nov 01, 2024

    • 3,240 Sq Ft
    • $185/SF
    • 6 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1900

    208 N Queen St, Chestertown, MD 21620

    Welcome to this charming Colonial four square home, nestled on the north end of Queen Street in Chestertown's historic district, just two blocks from the river. Step inside to find a beautifully remodeled kitchen, updated living room, dining room, den which doubles as a library or family room, and a sunlit porch, all on the main level. With high ceilings, intricate detailing, and polished

    Jody Baker Cross Street Realtors LLC

    208 N Queen St, Chestertown, MD 21620
    • /39

      Est $285,696 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,036 Sq Ft

      101 S College Ave, Chestertown, MD 21620

      101 S College Ave, Chestertown, MD 21620
  • /9

    $220,000 Under Contract

    • 1 Bed
    • 1 Bath
    • 882 Sq Ft

    619 Cannon St, Chestertown, MD 21620

    Ideally situated in Chestertown’s sought-after Historic District, this charming 1-bedroom, 1-bathroom cottage offers comfort, convenience, and plenty of potential. Enjoy a low-maintenance lifestyle just steps from downtown shops, restaurants, waterfront parks, and Washington College. The home features a bright and efficient layout, perfect for a weekend retreat, investment property, or full-time

    Sarah King Cross Street Realtors LLC

    619 Cannon St, Chestertown, MD 21620
  • /17

    $275,000 Sold Oct 29, 2024

    • 1,317 Sq Ft
    • $209/SF
    • 9 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1970

    24105 Chestertown Rd, Chestertown, MD 21620

    Custom quality-built 1970 brick rancher on 0.46 acre lot just outside Chestertown. House features original hardwood floors, stained woodwork, trim moldings and hand built wood kitchen cabinetry. The living room has large bay window and brick wood burning fireplace. Full unfinished basement offers lots of extra storage space with room to expand. Attached carport with storage closets and

    Yvonne Andres Keller Williams Select Realtors of Annapolis

    24105 Chestertown Rd, Chestertown, MD 21620
    • /12

      Est $290,553 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,756 Sq Ft

      203 Radcliffe Dr, Chestertown, MD 21620

      203 Radcliffe Dr, Chestertown, MD 21620
  • /72

    $625,000 Under Contract

    • 5 Beds
    • 3.5 Baths
    • 3,155 Sq Ft

    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 location of

    Hayley Norris Select Land & Homes, LLC

    10175 John Carvill Rd, Chestertown, MD 21620
  • /6

    $615,000 Sold Oct 25, 2024

    • 2,627 Sq Ft
    • $234/SF
    • 2 Beds
    • 1.5 Baths
    • Built 1998

    305 Hickory Ln, Chestertown, MD 21620

    Perfect Rabbit Creek and Chester River Get-A-Way. Ideal for an avid sportsman, outdoorsman or nature lover, offering you extensive frontage on Rabbit Creek leading out into the Chester River situated on 20 private acres. Offering a serene setting with a good mix of marshland, woods, uplands and a private pond. Bring your canoe/kayak/ john boat/ fishing pole and deer stand. These properties

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    305 Hickory Ln, Chestertown, MD 21620
    • /14

      Est $214,144 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,000 Sq Ft

      21385 Pennsylvania Ave, Chestertown, MD 21620

      21385 Pennsylvania Ave, Chestertown, MD 21620
  • /39

    $575,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 2,010 Sq Ft

    25285 Foxchase Dr, Chestertown, MD 21620

    Welcome to your private oasis! This charming home boasts mature landscaping that provides both beauty and privacy on a large corner lot. Custom built Cape Cod offers a first floor primary suite, living room with fireplace and built ins, formal dining room and a kitchen with granite counters and updated appliances. There’s an open area on the 2nd level ideal for reading or watching TV. Plus 2

    Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    25285 Foxchase Dr, Chestertown, MD 21620
  • /9

    $135,000 Sold Oct 25, 2024

    • 1,350 Sq Ft
    • $100/SF
    • 24 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1977

    10674 Kasota Rd, Chestertown, MD 21620

    Very affordable with a nice .59 acre lot. A great Re-Hab opportunity. Nicely located Rancher in Chesapeake Landing. Voluntary HOA membership allows access to Worton Creek. Property Backs up to Community Recreational Area with a pond. This is an opportunity to design your new home.

    Richard King Doug Ashley Realtors, LLC

    10674 Kasota Rd, Chestertown, MD 21620
    • /24

      Est $283,770 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,234 Sq Ft

      211 Philosophers Terrace, Chestertown, MD 21620

      211 Philosophers Terrace, Chestertown, MD 21620
  • /22

    $549,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,961 Sq Ft

    101 Birch Run Rd, Chestertown, MD 21620

    A sleek, thoughtfully executed renovation with clean lines and a minimalist aesthetic—sure to impress even the most discerning buyer... Located in Chestertown's coveted Mile Tree Village community, this newly updated 3-bedroom, 2-bath rancher with oversized 2-car garage features a new roof with 50-year shingles and a transferable warranty, new water and sewer lines to the street (2022), EV

    Stacy Kendall Cross Street Realtors LLC

    101 Birch Run Rd, Chestertown, MD 21620
  • /41

    $435,000 Sold Oct 24, 2024

    • 3,000 Sq Ft
    • $145/SF
    • 7 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1999

    100 Foxview Ct, Chestertown, MD 21620

    Nestled at the end of a serene cul-de-sac in the desirable Crestview neighborhood, this expansive 3,000-square-foot home resides on a generous 0.63-acre lot, boasting a delightful fusion of comfort and sophistication. Adorned with meticulously landscaped grounds, the outdoor space features a charming fish pond complemented by water features, a convenient shed, an expansive patio, and a deck

    Sarah Ulrick Rock Hall Properties Real Estate

    100 Foxview Ct, Chestertown, MD 21620
    • /36

      Est $918,472 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,352 Sq Ft

      9831 Breezecroft Ln, Chestertown, MD 21620

      9831 Breezecroft Ln, Chestertown, MD 21620
  • /40

    $599,900 Under Contract

    • 5 Beds
    • 2.5 Baths
    • 2,536 Sq Ft

    108 N Queen St, Chestertown, MD 21620

    Queen Street Gem! Located in the historic section of Chestertown, walk to the restaurants, shops, theater, farmer's market, and waterfront. Beautiful woodwork and pocket doors. Spacious rooms, hardwood flooring, solid wood doors, thick moldings, and ample closet space. Featuring 5 bedrooms and 2.5 baths, with 3 bedrooms on the second floor and 2 additional bedrooms on the 3rd floor. Bathrooms

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    108 N Queen St, Chestertown, MD 21620
  • /37

    $675,000 Sold Oct 21, 2024

    • 2,128 Sq Ft
    • $317/SF
    • 1 Day On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1961

    319 Fairview Dr, Chestertown, MD 21620

    Live authentically. Welcome to your dream waterfront oasis! This charming home, nestled in a serene spot near historic Chestertown, offers the perfect blend of community amenities and private retreat. Boasting three bedrooms and two beautifully designed bathrooms, this property is the epitome of move-in ready.Step inside to discover a host of updates that ensure modern convenience without

    Michelle Schwab Krauss Real Property Brokerage

    319 Fairview Dr, Chestertown, MD 21620
    • /27

      Est $252,458 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft

      316 Roosevelt Dr, Chestertown, MD 21620

      316 Roosevelt Dr, Chestertown, MD 21620
  • /56

    $749,900 Under Contract

    • 5 Beds
    • 3 Baths
    • 3,394 Sq Ft

    7988 Aldan Dr, Chestertown, MD 21620

    This is a stunning property! It combines elegance and functionality with its spacious layout, beautiful finishes, and thoughtful details. The open floor plan, combined with the cozy living room, pocket doors, and built-ins, creates a welcoming atmosphere. The kitchen, with its quartz countertops and wood floors, is a great space for cooking and entertaining. The main-level split bedroom floor

    Doug Ashley Doug Ashley Realtors, LLC

    7988 Aldan Dr, Chestertown, MD 21620
  • /22

    $287,000 Sold Oct 18, 2024

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

    235 Island Lark Way, Chestertown, MD 21620

    Village at Chestertown end-unit two-story townhome with 3 bedrooms and 2.5 bathrooms. The spacious first floor is open-concept consisting of a kitchen, living, and dining area. The thoughtfully designed kitchen comes with stylish gray cabinets, stainless steel appliances, a storage closet and a peninsula island that seats three. The first floor also offers a spacious living area and powder room.

    Derek Eisenberg Continental Real Estate Group

    235 Island Lark Way, Chestertown, MD 21620
    • /30

      Est $449,202 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,304 Sq Ft

      105 S Kent St, Chestertown, MD 21620

      105 S Kent St, Chestertown, MD 21620
  • /38

    $598,500 Under Contract

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

    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
  • /4

    $422,000 Sold Oct 18, 2024

    • 1,600 Sq Ft
    • $264/SF
    • 0 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2024

    231 Blakefield Dr, Chestertown, MD 21620

    3 BEDROOM 2 BATH RANCHER. OPEN FLOOR PLAN. NEW CONSTRUCTION TO START 2024. 1600SF ON 1 ACRE LOT

    Chris Haddaway Chesapeake Real Estate Associates, LLC

    231 Blakefield Dr, Chestertown, MD 21620
    • /44

      Est $645,239 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,536 Sq Ft

      225 Washington Ave, Chestertown, MD 21620

      225 Washington Ave, Chestertown, MD 21620
  • /52

    $795,000 Under Contract

    • 4 Beds
    • 4 Baths
    • 4,401 Sq Ft

    211 David Dr, Chestertown, MD 21620

    Big, bold, and beautiful! This wonderfully updated 2 story brick colonial in Chestertown is just minutes walking to the shops, restaurants, college, and waterfront. The first floor is enhanced with a finished sunroom with mini split, well appointed full bathroom adjacent to the office, and the kitchen of your dreams. Traditional aspects remain with a spacious dining room with built ins and living

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    211 David Dr, Chestertown, MD 21620
  • /48

    $260,000 Sold Oct 18, 2024

    • 1,150 Sq Ft
    • $226/SF
    • 263 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1949

    9020 Cumberland St, Chestertown, MD 21620

    Price improvement! Two perfectly adorable cottages in Tolchester. Both were completely remodeled. The cottages sit on 3 lots totaling about .46 acres. Each has one bedroom, a full bath, kitchen and living areas. The front cottage also has an additional "sleeping loft". Tolchester Beach is located on the Chesapeake Bay and has a beautiful beach and boat ramp. Walking distance to The Shanty

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    9020 Cumberland St, Chestertown, MD 21620
    • /32

      Est $489,853 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,700 Sq Ft

      311 Mayfair Dr, Chestertown, MD 21620

      311 Mayfair Dr, Chestertown, MD 21620
  • /48

    $579,900 Under Contract

    • 1 Bath
    • 1,148 Sq Ft

    5179 Quaker Neck Rd, Chestertown, MD 21620

    A One-of-a-Kind Historic Treasure Reimagined for Modern LivingStep into history with this extraordinary Greek Revival chapel, originally built in 1865 as Walton Chapel and later renamed Mowbray Chapel. Nestled on 3.22 picturesque acres in Chestertown’s serene Quaker Neck community, this stunning brick structure has been thoughtfully restored and modernized, seamlessly blending old-world charm

    Jonathan Taylor Hyatt & Company Real Estate, LLC

    5179 Quaker Neck Rd, Chestertown, MD 21620
  • /65

    $950,000 Sold Oct 17, 2024

    • 4,730 Sq Ft
    • $201/SF
    • 110 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2011

    7755 Waterview Ln, Chestertown, MD 21620

    This circa 2011, white brick house was built to celebrate the expansive views over the Chester River Yacht &Country Club golf course to the Chester River. There is an attractive patio at one end and a screened porch off the owner's suite. The landscaping around the circular driveway is lovely; the garage is set on an angle as to be unobtrusive from the road and the house entrance. Inside, all

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    7755 Waterview Ln, Chestertown, MD 21620
    • /13

      Est $229,865 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,000 Sq Ft

      21286 Maine Ave, Chestertown, MD 21620

      21286 Maine Ave, Chestertown, MD 21620
  • /32

    $364,900 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,724 Sq Ft

    216 Silver Heel Rd, Chestertown, MD 21620

    Welcome to this move-in ready home, situated on a premium corner lot in The Village at Chestertown! This charming 1,742 square foot, two-story home offers the perfect blend of comfort and style. The inviting front porch is an ideal spot to unwind with your morning coffee, enjoy the view of the open fields, and watch the clouds drift by.Inside, the well-designed layout begins with a foyer and

    Cynthia Gardner CENTURY 21 New Millennium

    216 Silver Heel Rd, Chestertown, MD 21620
  • /76

    $1,362,500 Sold Oct 16, 2024

    • 5,195 Sq Ft
    • $262/SF
    • 457 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1760

    201 N Water St, Chestertown, MD 21620

    SMITH-RINGGOLD HOUSE. ca. 1750 OWNER IS MEETING THE MARKET for this rare property WITH PRICE NOW AT $1,6500,000. This exceptional property is a rare find: an authentic waterfront 18th century home with 21st century comfort in heart of Historic Districtnof Chestertown on Maryland's Eastern Shore. Originally a merchant’s home , the Smith-Ringgold house has been tastefully modified

    Nancy McGuire Maryland Heritage Properties

    201 N Water St, Chestertown, MD 21620
    • /30

      Est $393,801 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,390 Sq Ft

      208 W Campus Ave, Chestertown, MD 21620

      208 W Campus Ave, Chestertown, MD 21620
  • /27

    $289,000 Under Contract

    • 3 Beds
    • 1.5 Baths
    • 1,248 Sq Ft

    1106 Round Top Rd, Chestertown, MD 21620

    Opportunity knocks! This 3-bedroom, 1.5-bath rancher sits on a spacious 2-acre lot in Queen Anne’s County. Enjoy the convenience of high-speed internet while taking in the peaceful surroundings. The home features an unfinished basement, offering potential for extra storage or future living space. With some vision and TLC, this property could shine—whether you're looking to renovate or start

    Clint Evans Cross Street Realtors LLC

    1106 Round Top Rd, Chestertown, MD 21620
  • /22

    $565,000 Sold Oct 07, 2024

    • 1,146 Sq Ft
    • $493/SF
    • 42 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1870

    125 High St, Chestertown, MD 21620

    This exquisitely renovated 1800s 2 Bedroom home showcases the timeless elegance of its original architecture. Every detail has been restored to its former glory with preserving its charm and character of its historic roots while incorporating modern updates for a truly exception living experience.Located in the heart of Chestertown with very easy walk to shops, restaurants, parks and just

    John Burke Gunther-McClary Real Estate

    125 High St, Chestertown, MD 21620
    • /23

      Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,530 Sq Ft

      114 High St, Chestertown, MD 21620

      114 High St, Chestertown, MD 21620
  • /53

    $324,900 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft

    109 Tamarack Rd, Chestertown, MD 21620

    Welcome to this beautiful 3-level Colonial in the sought-after Chester Harbor community on the Queen Anne’s County side! Nestled on a private lot, this home offers timeless charm, modern updates, and access to the water. Inside, you'll find three spacious bedrooms with newer carpeten upstairs with a full bathroom, while the main level features a large kitchen, dining room, and a cozy sitting area

    Crystal Smith RE/MAX Executive

    109 Tamarack Rd, Chestertown, MD 21620
  • /27

    $165,000 Sold Oct 04, 2024

    • 1,232 Sq Ft
    • $134/SF
    • 24 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1955

    21320 Persimmon Dr, Chestertown, MD 21620

    Fresh new look to this townhome includes fresh paint, new carpet and new HVAC system. Looking for an affordable option to paying rent? This two bedroom townhouse is just the answer. Close to the Bay and all Tolchester offers from it's marina, Shanty beach bar and the best spot for an incredible sunset. Tolchester Village offers the perfect location for those looking for a summer retreat or full

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    21320 Persimmon Dr, Chestertown, MD 21620
    • /44

      Est $930,238 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 2,276 Sq Ft

      9556 Chantilly Farm Ln, Chestertown, MD 21620

      9556 Chantilly Farm Ln, Chestertown, MD 21620
  • /19

    $329,900 Under Contract

    • 3 Beds
    • 2.5 Baths

    10578 Tonopah Rd, Chestertown, MD 21620

    Imagine waking up to gentle breezes and the promise of waterfront living. That's what awaits you in this brand-new home nestled within the peaceful Worton Creek community of Chesapeake Landing. Forget the cramped feeling of renting – here, you'll find space to breathe and room to grow.Picture yourself hosting friends and family in the bright, open living areas. The kitchen, with its crisp white

    David Moore RE/MAX Executive

    10578 Tonopah Rd, Chestertown, MD 21620
  • /36

    $380,000 Sold Oct 03, 2024

    • 1,625 Sq Ft
    • $234/SF
    • 9 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1970

    23118 Raleigh Rd, Chestertown, MD 21620

    Welcome to this beautifully updated rancher, offering a perfect blend of classic charm and modern amenities. This home boasts an oversized detached 2-car garage and an inviting in-ground saltwater pool. Inside, you'll find two fully remodeled bathrooms, stunning hardwood floors, and a back screened-in porch where you can relax and enjoy serene country views. Recent upgrades include a newer HVAC

    Kaitlyn Collins Benson & Mangold, LLC

    23118 Raleigh Rd, Chestertown, MD 21620

Showing Results 281 - 320, Page 8 of 18

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