7,060

Homes in ZIP Code 21620

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    • /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
  • /18

    $665,610 Pending

    • 4 Beds
    • 3.5 Baths
    • 3,599 Sq Ft

    3666 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.

    3666 Gratitude Way, Chestertown, MD 21620
  • /60

    $625,000 Sold Dec 10, 2024

    • 2,476 Sq Ft
    • $252/SF
    • 33 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 2002

    1316 Ewingtown Rd, Chestertown, MD 21620

    Welcome to 1316 Ewingtown Rd, where the charm of historic Chestertown meets the tranquility of rural living. Nestled on nearly 3 ½ acres of pristine land (main lot is 2.33 acres and adjacent lot is 1 acre), this Art Deco Farmhouse is a private retreat surrounded by thousands of acres of preserved farmland and woodlands. Just 45 minutes from Annapolis and Easton, and a quick 10-minute drive to

    Travis Gray Engel & Völkers Annapolis

    1316 Ewingtown Rd, Chestertown, MD 21620
    • /44

      Est $1,008,291 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
  • /2

    $10,000 Pending

    • Land
    • 0.73 Acre
    • $13,699 per Acre

    0 Iowa Ave, 6, Fairlee, MD 21620

    Court ordered sale - all offers subject to third party approval. Lot does not have a water/sewer allocation. All parties must do their due diligence with county to determine use of lot. Currently wooded 0.73 acre lot on right corner of Iowa, Elm/Cumberland & Montgomery Avenues.

    John Carroll Village Real Estate Company LLC

    0 Iowa Ave, 6, Fairlee, MD 21620
  • /22

    $342,000 Sold Dec 09, 2024

    • 1,200 Sq Ft
    • $285/SF
    • 3 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1997

    218 Concord Rd, Chestertown, MD 21620

    Charming 3-bedroom, 2-bath rancher located in the desirable Chester Harbor neighborhood! This move-in-ready home features a recently updated kitchen with quartz counters and new flooring in the bedrooms. New heat pump. Enjoy the spacious, fenced-in backyard complete with a screened-in porch and fire pit. A large shed offers extra storage. Conveniently situated just minutes from downtown

    Courtney Chipouras TTR Sotheby's International Realty

    218 Concord Rd, Chestertown, MD 21620
    • /28

      Est $254,892 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 929 Sq Ft

      545 High St, Chestertown, MD 21620

      545 High St, Chestertown, MD 21620
  • /2

    $12,500 Pending

    • Land
    • 0.50 Acre
    • $25,000 per Acre

    0 Millbrook Dr, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Millbrook Dr, Chestertown, MD 21620
  • /33

    $329,000 Sold Dec 06, 2024

    • 1,473 Sq Ft
    • $223/SF
    • 35 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1965

    23055 Parsons Rd, Chestertown, MD 21620

    Well Maintained rancher with major renovations. Updating Kitchen including recently new stainless steel appliances and cabinets, Bathrooms, HW flooring refinished, fresh Paint throughout, move-in condition. New boiler, new water heater & new central A/c in 2011. Full basement -Office/den in basement w/ built-in book shelves and tile floor that has a separate entrance. Laundry area in basement.

    Sharon Clark Clark & Co Realty, LLC

    23055 Parsons Rd, Chestertown, MD 21620
    • /47

      Est $328,856 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,360 Sq Ft

      9041 S Bayview Dr, Chestertown, MD 21620

      9041 S Bayview Dr, Chestertown, MD 21620
  • /4

    $325,000 Coming Soon

    • 1 Bed
    • 1.5 Baths
    • 936 Sq Ft

    108 S Kent St, Chestertown, MD 21620

    Cute as a button in the historic district on South Kent St. This 1 bedroom, 1.5 bath home is in the center of town within walking distance to the farmers market and all the shops and restaurants. There is potential for a second bedroom upstairs if you add a wall between the bedroom and the sitting area. Adorable backyard. Perfect for one or two people as a full-time residence or weekend getaway.

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    108 S Kent St, Chestertown, MD 21620
  • /33

    $250,000 Sold Dec 06, 2024

    • 1,632 Sq Ft
    • $153/SF
    • 88 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1965

    305 Lincoln Dr, Chestertown, MD 21620

    Looking for extra space? This home has a large extra room that could be a primary bedroom & bath with walk-in closet, a den/playroom, office with a separate private entrance, gym, or whatever your lifestyle needs! The original primary bedroom includes an attached half bath and the original hardwood floors gleam throughout most of the home! Easy access to multiple public ramps & just a short drive

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    305 Lincoln Dr, Chestertown, MD 21620
    • /69

      Est $1,301,975 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,869 Sq Ft

      10069 John Carvill Rd, Chestertown, MD 21620

      10069 John Carvill Rd, Chestertown, MD 21620
  • /7

    $1,100,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 2,600 Sq Ft

    492 Pear Tree Point Rd, Chestertown, MD 21620

    Great opportunity to own a waterfront property on the scenic Chester River! This beautifully landscaped 3 bedroom, 2 bath home with a wraparound porch offers stunning views. There is an additional 700+/- sq ft space over the garage, filled with natural light and river views, ideal for extra bedrooms with bath, master bedroom or an in-law suite. Tucked away in a peaceful, private setting on a

    Leo Kuneman Meredith Fine Properties

    492 Pear Tree Point Rd, Chestertown, MD 21620
  • /22

    $374,900 Sold Dec 06, 2024

    • 1,512 Sq Ft
    • $248/SF
    • 223 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2024

    481 Pear Tree Point Rd, Chestertown, MD 21620

    Major Price Reduction - Brand New Home ready ready for ALL your Holiday Celebrations! Lawn has been freshly seeded and new shrubs planted for the fall. Three generous bedrooms and 2.5 baths! Enjoy beautiful water views of the Chester River... just across the street! Open floor plan, stainless steel appliances, main-level master suite with a walk-in closet and ensuite. Upstairs, you'll find two

    Clint Evans Cross Street Realtors LLC

    481 Pear Tree Point Rd, Chestertown, MD 21620
    • /45

      Est $431,535 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,464 Sq Ft

      502 Cannon St, Chestertown, MD 21620

      502 Cannon St, Chestertown, MD 21620
  • /3

    $199,900 Coming Soon

    • 2 Beds
    • 1 Bath
    • 1,296 Sq Ft

    234 N College Ave, Chestertown, MD 21620

    Investor Special – Charming Colonial in Prime Chestertown Location!Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their vision to life. With classic colonial charm, this property offers the perfect canvas for renovation

    Anastasia Zivkovic Cummings & Co. Realtors

    234 N College Ave, Chestertown, MD 21620
  • /24

    $355,000 Sold Dec 02, 2024

    • 1,536 Sq Ft
    • $231/SF
    • 64 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1962

    24291 Chestertown Rd, Chestertown, MD 21620

    Price Improvement - Welcome to this delightful brick rancher, offering over 1,500 square feet of comfortable, inviting living space. This home boasts 3 spacious bedrooms and 2 full baths, perfectly designed to accommodate a variety of lifestyles. Step inside and be greeted by the open floor plan, where the brick fireplace in the living room adds both charm and warmth—an ideal gathering spot for

    Joelle Dolch Cross Street Realtors LLC

    24291 Chestertown Rd, Chestertown, MD 21620
    • /44

      Est $437,522 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,700 Sq Ft

      111 Manor Ave, Chestertown, MD 21620

      111 Manor Ave, Chestertown, MD 21620
  • /62

    $815,000 Under Contract

    • 2 Beds
    • 1.5 Baths
    • 1,401 Sq Ft

    209 Rivershore Rd, Chestertown, MD 21620

    WELCOME TO 209 RIVERSHORE RD., CHESTERTOWN MD.,, Your natural waterfront retreat on the Chester River. Enjoy your time outside or inside of this tranquil property. As you step inside of this open flowy home with natural wood floors you will see the kitchen which has been partially remodeled with SS appliances, new counters and plenty of cabinet space. Overlooking the large spacious dining area

    Barbara McPhail Douglas Realty LLC

    209 Rivershore Rd, Chestertown, MD 21620
  • /73

    $675,000 Sold Nov 26, 2024

    • 2,400 Sq Ft
    • $281/SF
    • 27 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2011

    6270 Quaker Neck Landing Rd, Chestertown, MD 21620

    From the moment you drive up to this beautiful home, you are struck by the beautiful landscaping that complements the home, includes a rain garden, cutting garden, wildflower garden and a walkway that leads to an outdoor patio that provides such a great space for outdoor living. The orchard has peaches, plum, apple trees as well as berries and grapes. The enclosed screen porch overlooks the

    Retha Arrabal Doug Ashley Realtors, LLC

    6270 Quaker Neck Landing Rd, Chestertown, MD 21620
    • /40

      Est $442,186 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,080 Sq Ft

      8610 Camp Rd, Chestertown, MD 21620

      8610 Camp Rd, Chestertown, MD 21620
  • /49

    $975,000 Under Contract

    • 4 Beds
    • 3 Baths
    • 3,401 Sq Ft

    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
  • /6

    $152,881 Sold Nov 25, 2024

    • 1,232 Sq Ft
    • $124/SF
    • 14 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1955

    21345 Persimmon Dr, Chestertown, MD 21620

    Join the small Tolchester Village community in a nice two bedroom and one bath town house. Remodeled in 2021 this modern home features low maintenance living. It could use a little tlc to make it your own. Outdoor storage areas are located in the front and back. There is a small back patio where you can sit and enjoy your morning coffee. Never worry about mowing the grass as the small HOA

    Vince Raimond Doug Ashley Realtors, LLC

    21345 Persimmon Dr, Chestertown, MD 21620
    • /44

      Est $640,874 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,244 Sq Ft

      207 N Queen St, Chestertown, MD 21620

      207 N Queen St, Chestertown, MD 21620
  • /47

    $665,000 Under Contract

    • 4 Beds
    • 4 Baths
    • 2,544 Sq Ft

    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
  • /32

    $239,000 Sold Nov 25, 2024

    • 1,202 Sq Ft
    • $199/SF
    • 7 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1961

    5 Rolling Rd, Chestertown, MD 21620

    Brick rancher located in College Heights! There are 3 bedrooms and living room, all with wood floors. There is a large family room with built-ins. There is a full unfinished basement with connecting interior stairs and exterior stairs. The rear porch is ready to be screened in. Property backs up to woods. Close to hospital, parks and schools. This home will require a little TLC however the

    Doug Ashley Doug Ashley Realtors, LLC

    5 Rolling Rd, Chestertown, MD 21620
    • /50

      Est $758,854 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,736 Sq Ft

      201 Radcliffe Dr, Chestertown, MD 21620

      201 Radcliffe Dr, Chestertown, MD 21620
  • /20

    $245,000 Under Contract

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    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
  • /27

    $405,000 Sold Nov 22, 2024

    • 1,426 Sq Ft
    • $284/SF
    • 39 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2014

    142 Church Meadow Ct, Chestertown, MD 21620

    Conveniently located between Church Hill and Chestertown this home sits on a quiet cul de sac with 1.25 acre lot backing to farm fields. Fenced rear yard is great for 2 or 4 legged family members and provides ample room to play, garden, or just relax. Inside features over 1400 SQFT of finished space with 3 bedrooms, 2.5 bathrooms and great lower level family room with walk out to rear yard

    Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

    142 Church Meadow Ct, Chestertown, MD 21620
    • /29

      Est $176,467 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 936 Sq Ft

      21715 Tolchester Beach Rd, Chestertown, MD 21620

      21715 Tolchester Beach Rd, Chestertown, MD 21620
  • /10

    $175,000 Under Contract

    • 2 Beds
    • 1.5 Baths
    • 1,160 Sq Ft

    23069 Raleigh Rd, Chestertown, MD 21620

    Rancher with a 1/3 of an acre with 2 bedrooms and 1 full bath and a wheelchair accessible shower. Plenty of parking, with a driveway in front and back of the house. Inside of the house in need of work, with painting and flooring throughout. Roof was replaced in 2022.

    George Mcdowell Keller Williams Select Realtors of Annapolis

    23069 Raleigh Rd, Chestertown, MD 21620
  • /25

    $565,000 Sold Nov 18, 2024

    • 2,488 Sq Ft
    • $227/SF
    • 3 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1980

    209 Birch Run Rd, Chestertown, MD 21620

    Upgrades GALORE... wait til you see how this house has been transformed into a home! A spacious four bedroom, three full bath layout on over half acre in one of Chestertown's most desirable neighborhoods: professional kitchen appliances, renovated bathrooms, high end flooring finishes, bonus sun room, fenced back yard, asphalt driveway heading to the two car garage... plus so much more. Live for

    Liddy Campbell TTR Sotheby's International Realty

    209 Birch Run Rd, Chestertown, MD 21620
    • /30

      Est $363,106 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,680 Sq Ft

      215 Devon Dr, Chestertown, MD 21620

      215 Devon Dr, Chestertown, MD 21620
  • /19

    $335,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    10578 Tonopah Rd, Chestertown, MD 21620

    Why settle for outdated or overpriced when you can own brand-new construction in a waterfront community just minutes from historic Chestertown? This 3-bed, 2.5-bath Cape Cod in Chesapeake Landing is designed for easy, elegant living—featuring an open floor plan, main-level primary suite with walk-in closet and attached bath, and luxe finishes throughout. Enjoy luxury vinyl plank flooring, granite

    David Moore RE/MAX Executive

    10578 Tonopah Rd, Chestertown, MD 21620
  • /26

    $340,000 Sold Nov 18, 2024

    • 1,566 Sq Ft
    • $217/SF
    • 79 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1974

    503 N Kent St, Chestertown, MD 21620

    Within walking distance of Washington College, medical services, parks and schools and convenient to historic downtown arts and entertainment district, this low-maintenance- exterior brick rancher is ready for your personal decorating touches. Living Room and formal dining room. One primary bedroom with en suite bath. Two additional bedrooms and a family bathroom. Country kitchen with

    Hugh Wyble Wyble Enterprises

    503 N Kent St, Chestertown, MD 21620
    • /69

      Est $510,551 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,200 Sq Ft

      110 Camelot Dr, Chestertown, MD 21620

      110 Camelot Dr, Chestertown, MD 21620
  • /10

    $75,000 Under Contract

    • Land
    • 2.36 Acres
    • $31,780 per Acre

    9020 Georgetown Rd, Chestertown, MD 21620

    Price improvement!!! Pretty wooded parcel recently surveyed with stakes clearly showing property boundaries. SEE DOCUMENTS for plat and aerial view. Property already has a sewer allocation. Tax record shows 3 acres but recent survey confirms 2.356 acres. There is an old collapsed trailer on site that did have electric at one time. Seller is in the process of removing the trailer and any

    Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

    9020 Georgetown Rd, Chestertown, MD 21620
  • /36

    $370,247 Sold Nov 15, 2024

    • 2,092 Sq Ft
    • $177/SF
    • 120 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1998

    201 Princess Anne Dr, Chestertown, MD 21620

    Where Shore living begins! Welcome to 201 Princess Anne, located on the Queen Anne's County side of the Chester River Bridge. This well maintained home is established on just over 3/4 of an acre within the quiet subdivision of Kingstowne Manor. Offering 3 bedrooms, 2 baths, attached garage and comes equipped with a fully floored attic for all of your storage needs! A new roof system was

    Andrew Meikle Doug Ashley Realtors, LLC

    201 Princess Anne Dr, Chestertown, MD 21620
    • /31

      Est $345,660 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,944 Sq Ft

      103 Trafford Dr, Chestertown, MD 21620

      103 Trafford Dr, Chestertown, MD 21620

Showing Results 321 - 360, Page 9 of 18

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