Chestertown, Maryland Homes For Sale & Real Estate

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Real Estate Homes For Sale In Chestertown, MD

Welcome to 23530 Clarissa Road! This well maintained home is established on a beautifully situated lot located within the water access community of Chesapeake Landing. You'll be greeted here by vibrant greens, found flourishing through mature....

CHESTERTOWN Homes |

MLS #MDKE2003944

 Single Family Residence

$345,000 | Active Home listing

3 Beds | 2 Baths | 1,812 Sqft | 0 Acres Lot

23530 CLARISSA ROAD, CHESTERTOWN, MD 21620 KENT County

Real Estate Details & Photos
Welcome to 7488 Poplar Ave in the heart of Chestertown. This charming 3-bedroom, 2-bath rancher nestled in a serene setting, backing onto scenic woods. Built in 2019, this modern home offers a perfect blend of comfort and style. As you step....

CHESTERTOWN Homes |

MLS #MDKE2003902

 Single Family Residence

$250,000 | Active Home listing

3 Beds | 2 Baths | 1,232 Sqft | 0 Acres Lot

7488 POPLAR AVENUE, CHESTERTOWN, MD 21620 KENT County

Real Estate Details & Photos
Extraordinary opportunity to purchase the estate of Clorea Truslow—the cherished namesake of Truslow Rd. For generations, this land has been held dear by the Truslow family, and now, for the first time, it is being offered for sale, presenting a....

CHESTERTOWN Homes |

MLS #MDQA2009684

 Single Family Residence

$729,000 | Active Home listing

4 Beds | 3 Baths | 2,945 Sqft | 1 Acres Lot

204 TRUSLOW FARM LANE, CHESTERTOWN, MD 21620 QUEEN ANNES County

Real Estate Details & Photos
Lovely Cape Cod in desirable Byford Heights. First-floor Primary Bedroom and Bathroom. 2 large bedrooms with full Bathroom on 2nd floor. Beautiful Hardwood floors. Easy flowing floor plan guides you from bright living room to the dining room and....

CHESTERTOWN Homes |

MLS #MDKE2003778

 Single Family Residence

$365,000 | Active Home listing

3 Beds | 3 Baths | 2,045 Sqft | 0 Acres Lot

208 BYFORD DRIVE, CHESTERTOWN, MD 21620 KENT County

Real Estate Details & Photos
Welcome home to Tolchester Village. This 2 bedroom 1 bathroom townhome is short distance to Rock Hall or Chestertown. This efficient townhome offers a tranquil setting with an abundance of wildlife in a park like setting just of the back patio....

CHESTERTOWN Townhome |

MLS #MDKE2003862

 Townhouse

$154,900 | Active Home listing

2 Beds | 1 Baths | 1,232 Sqft | 0 Acres Lot

21345 PERSIMMON DRIVE, CHESTERTOWN, MD 21620 KENT County

Townhouse Details & Photos
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....

CHESTERTOWN Homes |

MLS #MDKE2003814

 Single Family Residence

$975,000 | Active Home listing

4 Beds | 3 Baths | 4,730 Sqft | 1 Acres Lot

7755 WATERVIEW LANE, CHESTERTOWN, MD 21620 KENT County

Real Estate Details & Photos
Wonderful renovation, modern, efficient, and move in ready! Home features vaulted ceilings with open flexible floorplan and 2 brand new luxury bathrooms. Energy efficient instant hot water heater. Large side deck, plenty of parking, small....

CHESTERTOWN Homes |

MLS #MDQA2009482

 Single Family Residence

$289,000 | Active Home listing

2 Beds | 2 Baths | 864 Sqft | 1 Acres Lot

235 BURCHARD SAWMILL ROAD, CHESTERTOWN, MD 21620 QUEEN ANNES County

Real Estate Details & Photos
Step into a world of timeless elegance and tranquility with this meticulously maintained retreat. As you turn into the Fairgale Subdivision, it feels as though you are entering an estate, with majestic trees lining both sides of the paved road,....

CHESTERTOWN Homes |

MLS #MDKE2003704

 Single Family Residence

$1,360,000 | Active Home listing

5 Beds | 5 Baths | 6,459 Sqft | 4 Acres Lot

22956 FAIRGALE FARM LANE, CHESTERTOWN, MD 21620 KENT County

Real Estate Details & Photos
Well maintained 2 bedroom 1 bath Colonial on .69 acres with winter water views of Fishing Creek! Features Include: Screened Porch * 1-Car Attached Garage * Tilt-in Insulated Double Pane Windows * Large Living / Dining Room Combo with Brick....

CHESTERTOWN Homes |

MLS #MDQA2009122

 Single Family Residence

$279,000 | Active Home listing

2 Beds | 1 Baths | 1,408 Sqft | 1 Acres Lot

332 TRUSLOW ROAD, CHESTERTOWN, MD 21620 QUEEN ANNES County

Real Estate Details & Photos
NEW PICTURES and Price Improvement! Welcome to this cozy 3 bedroom, 1 bath remodeled Swiss cottage with views of the Chester River and a lovely yard full of mature gardens. Located in Queen Anne's County, Chestertown, MD, the sounds of geese and....

CHESTERTOWN Homes |

MLS #MDQA2008806

 Single Family Residence

$429,000 | Active Home listing

3 Beds | 1 Baths | 1,128 Sqft | 0 Acres Lot

134 CHAR NOR MANOR BOULEVARD, CHESTERTOWN, MD 21620 QUEEN ANNES County

Real Estate Details & Photos
Welcome to your tranquil retreat at Orchard Hill, where modern sophistication meets peaceful living on 1.89 acres of beautifully landscaped grounds. This stunning Cape Cod style home offers an abundance of amenities and thoughtful details....

CHESTERTOWN Homes |

MLS #MDKE2003556

 Single Family Residence

$498,000 | Active Home listing

2 Beds | 3 Baths | 2,210 Sqft | 2 Acres Lot

8757 ORCHARD DRIVE, CHESTERTOWN, MD 21620 KENT County

Real Estate Details & Photos
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....

CHESTERTOWN Homes |

MLS #MDKE2003374

 Single Family Residence

$297,000 | Active Home listing

2 Beds | 2 Baths | 1,150 Sqft | 0 Acres Lot

9020 CUMBERLAND STREET, CHESTERTOWN, MD 21620 KENT County

Real Estate Details & Photos
SMITH-RINGGOLD HOUSE. ca. 1750 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 ,....

CHESTERTOWN Homes |

MLS #MDKE2002790

 Single Family Residence

$1,725,000 | Active Home listing

4 Beds | 5 Baths | 5,195 Sqft | 0 Acres Lot

201 N WATER STREET, CHESTERTOWN, MD 21620 KENT County

Real Estate Details & Photos
Chestertown Rancher in Country Club Estates! This rancher overlooks the golf course with distant water views. Amenities include fireplace, 2 car detached garage, storage building, wood floors, dining room, circular driveway, and laundry room. This....

CHESTERTOWN Homes |

MLS #MDKE2003970

 Single Family Residence

$310,000 | Active Home listing

2 Beds | 2 Baths | 2,175 Sqft | 0 Acres Lot

7671 WATERVIEW LANE, CHESTERTOWN, MD 21620 KENT COUNTY County

Real Estate Details & Photos

Chestertown, MD Real Estate Home Trends

Kent County Buy Statistics

  • Total Housesolds
  • 8,375
  • Median Home Value
  • $291,900
  • Median Housing Costs
  • $1,781
  • Median Household Income
  • $71,635
  • Median Real Estate Taxes
  • $Not Available
  • Homes With Primary Mortgage Only
  • Not Available%
    		•
    • Homes With Second Mortgage
    • Not Available%
    • Homes With Home Equity Mortgage Only
    • Not Available%

    Chestertown Types of Homes for Sale

    Chestertown Real Estate Listings

    Chestertown Homes For Sale















    Chestertown, MD Homes Prices

    • Total Housesolds
    • 8,375
    • Median Home Value
    • $411,900
    • Median Housing Costs
    • $2,097
    • Median Household Income
    • $94,991
    • Average Household Income
    • $125,876
    • Median Real Estate Taxes
    • $3,857
    • Homes With Primary Mortgage Only
  • 86.9%
    		•
    • Homes With Second Mortgage
    • 10.6%
    • Homes With Home Equity Mortgage Only
    • 2.5%
    • Total Population
    • 6,164,660
    • Median Age
    • 39.7
    • Male To Female Ratio
    • 95.1
    • Average Household Size
    • 2.76
    • Median Rent For House
    • $1,550
    • Owner-Occupied House Units
    • 67.7%
    • Renters Occupied House Units
    • 32.3%

    Real Estate Home Mortgage Loan Rates Chestertown Maryland

    Home loan finance mortgage calculator to find Maryland real estate payment calculations

    Housing Calculator Affordability

    About Chestertown

    • Chestertown has total households of 8,375 with a real estate for sale median home value of $291,900 compared to the state median home price of $411,900. The median real estate taxes paid are $Not Available and the household income is $71,635. Not Available% of Chestertown homes with a mortgage have no second mortgage or home equity line of credit. Chestertown Maryland home types of MLS housing to buy including single family homes, condos, townhomes, residential studio, apartment, townhouse, and multi-family houses.

    Chestertown Neighborhoods

    What Zip Codes in Chestertown have homes for sale listing?

    City neighborhood housing zip codes have MLS listing homes for sale within Chestertown, MD for buyers: 21620, 21690.

    Chestertown Local Economy & Job Opportunities

    The median household income is 71,635 and the median state household income is 94,991. The average household income is 125,876 in Maryland.

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