6,817

Chestertown, MD Homes

Section Image Section Image
  • 226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    226 S Water St, Chestertown, MD 21620
    /31

    $898,000

    • 3 Beds
    • 3.5 Baths
    • 2,172 Sq Ft

    226 S Water St, Chestertown, MD 21620

    Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring a gourmet kitchen; 5-burner induction range, ample cabinet space, and a large island for entertaining. The home is filled with natural light and boasts multiple balconies and a front porch for relaxing. You'll love the warm hardwood floors throughout the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    226 S Water St, Chestertown, MD 21620
  • 101 Morgnec Rd, Chestertown, MD 21620
    101 Morgnec Rd, Chestertown, MD 21620
    101 Morgnec Rd, Chestertown, MD 21620
    /23

    Starting at $1,300 Per Month

    • 1 - 3 Beds

    101 Morgnec Rd, Chestertown, MD 21620

    Quiet community, beautifully landscaped. Close to Washington College, can walk to downtown historic Chestertown and shops. A must see.

    Kent Crossing Apartments

    101 Morgnec Rd, Chestertown, MD 21620
  • 521 N Kent St, Chestertown, MD 21620
    521 N Kent St, Chestertown, MD 21620
    /2

    $365,000

    Sold Jul 22, 2026

    521 N Kent St, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,934 Sq Ft
    • Built 1971

    Last Sold Summary

    • 5% Below List Price
    • $189/SF

    Current Estimated Value $444,216

    Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    521 N Kent St, Chestertown, MD 21620
    • 9190 N Bayview Ave, Chestertown, MD 21620
      9190 N Bayview Ave, Chestertown, MD 21620
      9190 N Bayview Ave, Chestertown, MD 21620
      /38

      Est $302,256

      Not Listed For Sale

      9190 N Bayview Ave, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 1,160 Sq Ft
      • Built 1969
      9190 N Bayview Ave, Chestertown, MD 21620

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Hayley Norris Select Land & Homes, LLC

  • 305 Roosevelt Dr, Chestertown, MD 21620
    305 Roosevelt Dr, Chestertown, MD 21620
    /2

    $60,000

    • Land
    • 26,571 Sq Ft
    • $98,361 per Acre

    305 Roosevelt Dr, Chestertown, MD 21620

    Nice cleared building lot in an established community. Public water and sewer available. Property recently acquired through tax sale foreclosure. Law Firm of Shaw and Crowson P.A. in Salisbury preferred for settlement.

    Agent Photo

    Joe Howerton

    Taylor Properties

    305 Roosevelt Dr, Chestertown, MD 21620
  • 200 Cannon St Unit 1A, Chestertown, MD 21620
    200 Cannon St Unit 1A, Chestertown, MD 21620
    200 Cannon St Unit 1A, Chestertown, MD 21620
    /20

    $1,300

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 580 Sq Ft
    • Condo for Rent

    200 Cannon St Unit 1A, Chestertown, MD 21620

    Ground floor apartment in nice, safe, quiet, upscale area 2 blocks from river and waterfront park, 1 block from downtown (in Historic District). Suitable for 1 person. No pets or smoking.

    200 Cannon St Unit 1A, Chestertown, MD 21620
  • 108 Flying Cloud Dr, Chestertown, MD 21620
    108 Flying Cloud Dr, Chestertown, MD 21620
    108 Flying Cloud Dr, Chestertown, MD 21620
    /21

    $364,900

    Sold Feb 26, 2026

    108 Flying Cloud Dr, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 1,936 Sq Ft
    • Built 2023

    Last Sold Summary

    • $188/SF
    • 67 Days On Market

    Current Estimated Value $361,480

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    108 Flying Cloud Dr, Chestertown, MD 21620
    • 106 Wilton Rd, Chestertown, MD 21620
      106 Wilton Rd, Chestertown, MD 21620
      106 Wilton Rd, Chestertown, MD 21620
      /36

      Est $313,165

      Not Listed For Sale

      106 Wilton Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1975
      106 Wilton Rd, Chestertown, MD 21620

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Crystal Smith RE/MAX Executive

  • 7415 Wilkins Ln, Chestertown, MD 21620
    7415 Wilkins Ln, Chestertown, MD 21620
    7415 Wilkins Ln, Chestertown, MD 21620
    /23

    $229,000

    • 3 Beds
    • 1 Bath
    • 936 Sq Ft

    7415 Wilkins Ln, Chestertown, MD 21620

    This 3-bedroom, 1-bathroom ranch-style home in Quaker Estates offers a solid investment opportunity with a total finished area of 936 sq ft. Built in 1963, the property features essential appliances including a refrigerator and stove, ensuring immediate functionality for tenants or future buyers. The average condition of the home allows for potential value-add renovations, which can significantly

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    7415 Wilkins Ln, Chestertown, MD 21620
  • 128 N Queen St Unit 3, Chestertown, MD 21620
    128 N Queen St Unit 3, Chestertown, MD 21620
    128 N Queen St Unit 3, Chestertown, MD 21620
    /10

    $1,450 Per Month

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft
    • House for Rent

    128 N Queen St Unit 3, Chestertown, MD 21620

    Welcome to 128 N Queen Street, Unit 2. Utilities included!!!A beautiful Victorian apartment located downtown Chestertown within walking distance to the Chester River and situated close to the Washington College. 2nd floor private unit with spacious living area, separate dining room, galley kitchen, full bathroom and bedroom. All with a fresh coat of paint! Unit is available immediately,

    Amanda Morgan Brenton Realty Group

    128 N Queen St Unit 3, Chestertown, MD 21620
  • 676 Deep Landing Rd, Chestertown, MD 21620
    676 Deep Landing Rd, Chestertown, MD 21620
    676 Deep Landing Rd, Chestertown, MD 21620
    /24

    $325,000

    Sold Jan 23, 2026

    676 Deep Landing Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,468 Sq Ft
    • Built 2014

    Last Sold Summary

    • $221/SF
    • 2 Days On Market

    Current Estimated Value $334,874

    Last Listing Agent Katie Stecklair Cross Street Realtors LLC

    676 Deep Landing Rd, Chestertown, MD 21620
    • 7425 Wilkins Ln, Chestertown, MD 21620
      7425 Wilkins Ln, Chestertown, MD 21620
      7425 Wilkins Ln, Chestertown, MD 21620
      /29

      Est $302,714

      Not Listed For Sale

      7425 Wilkins Ln, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,341 Sq Ft
      • Built 1962
      7425 Wilkins Ln, Chestertown, MD 21620

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent LAURIE KREIDER Realty ONE Group Unlimited

  • 0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
    /2

    $59,000

    $5K PRICE DROP
    • Land
    • 1.37 Acres
    • $43,066 per Acre

    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620

    (Lot 2 - .685 acres & Lot 3 - .689 acres) Conveniently located slightly off 291, in a private area on a dead-end road, this property is close to Chestertown and minutes away from route 301. Lots sit high off the road level and adorned with young saplings. Soil evaluation from 2011 approved for 3 beds and a 2,000 sq ft home, located just outside the critical area. Unsuccessful land evaluation

    Agent Photo

    Kristina Hyland

    Coldwell Banker Chesapeake Real Estate Company

    0 Old Morgnec Rd Unit MDKE2004974, Chestertown, MD 21620
  • 206 N Mill St, Chestertown, MD 21620
    206 N Mill St, Chestertown, MD 21620
    206 N Mill St, Chestertown, MD 21620
    /13

    $1,950 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,520 Sq Ft
    • House for Rent

    206 N Mill St, Chestertown, MD 21620

    Entire historic home in downtown Chestertown for a great price!! One block from shops, restaurants, galleries and much more. Large living room opens to eat-in kitchen with beautiful countertops and all stainless steel appliances. Half bath and laundry on main floor and 3 bedrooms and two full bathrooms upstairs. Hardwood floors throughout. Private backyard with fence and storage shed. Dead end

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    206 N Mill St, Chestertown, MD 21620
  • 25475 Turnberry Ct, Chestertown, MD 21620
    25475 Turnberry Ct, Chestertown, MD 21620
    25475 Turnberry Ct, Chestertown, MD 21620
    /79

    $825,000

    Sold May 26, 2026

    25475 Turnberry Ct, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 4,145 Sq Ft
    • Built 2018

    Last Sold Summary

    • 5% Below List Price
    • $199/SF
    • 9 Days On Market

    Current Estimated Value $830,284

    Last Listing Agent Lona Todd Taylor Properties

    25475 Turnberry Ct, Chestertown, MD 21620
    • 148 Grant Ct, Chestertown, MD 21620
      148 Grant Ct, Chestertown, MD 21620
      148 Grant Ct, Chestertown, MD 21620
      /30

      Est $467,518

      Not Listed For Sale

      148 Grant Ct, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,664 Sq Ft
      • Built 2021
      148 Grant Ct, Chestertown, MD 21620

      Last Sold Summary

      • 67 Days On Market

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • 108 Little Harbor Way, Chestertown, MD 21620
    108 Little Harbor Way, Chestertown, MD 21620
    108 Little Harbor Way, Chestertown, MD 21620
    /5

    $635,000

    • Land
    • 3,920 Sq Ft
    • $7,055,556 per Acre

    108 Little Harbor Way, Chestertown, MD 21620

    Buildable waterfront lot in the Chester River Landing community. This prime location captures panoramic views of the Chester River! Just steps away from deep water boat slips, which are available for lease or purchase. Perfect location to build your dream home on the water. The Chester River Landing community amenities include docks, in-ground pool, grilling and outdoor dining area right on the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    108 Little Harbor Way, Chestertown, MD 21620
  • 104 Maple Ave Unit 3, Chestertown, MD 21620
    104 Maple Ave Unit 3, Chestertown, MD 21620
    104 Maple Ave Unit 3, Chestertown, MD 21620
    /7

    $1,495 Per Month

    • 2 Beds
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    104 Maple Ave Unit 3, Chestertown, MD 21620

    Nick Dively Real Broker, LLC - Annapolis

    104 Maple Ave Unit 3, Chestertown, MD 21620
  • 907 N Meadowview Dr, Chestertown, MD 21620
    907 N Meadowview Dr, Chestertown, MD 21620
    907 N Meadowview Dr, Chestertown, MD 21620
    /33

    $375,000

    Sold Dec 01, 2025

    907 N Meadowview Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,842 Sq Ft
    • Built 2002

    Last Sold Summary

    • $204/SF
    • 83 Days On Market

    Current Estimated Value $382,771

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    907 N Meadowview Dr, Chestertown, MD 21620
    • 104 Metcalf Rd, Chestertown, MD 21620
      104 Metcalf Rd, Chestertown, MD 21620
      104 Metcalf Rd, Chestertown, MD 21620
      /17

      Est $247,059

      Not Listed For Sale

      104 Metcalf Rd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • Built 2023
      104 Metcalf Rd, Chestertown, MD 21620

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent David Moore Real Broker, LLC

  • 0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
    /5

    $55,000

    • Land
    • 3 Acres
    • $18,333 per Acre

    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620

    Back on the market due to buyer's failure to perform. Due diligence was done with the County as far as hooking up to the septic system but verify with Kent County Public Works. The corners have been marked and survey is in the documents tab. E Georgetown Rd - Parcel 70, Chestertown MD consists of 3 acres. Public water/sewer hookup is available through Kent County. Loads of opportunities for a

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
  • 104 Maple Ave Unit 4, Chestertown, MD 21620
    104 Maple Ave Unit 4, Chestertown, MD 21620
    104 Maple Ave Unit 4, Chestertown, MD 21620
    /12

    $1,795 Per Month

    • 2 Beds
    • 2 Baths
    • 900 Sq Ft
    • Condo for Rent

    104 Maple Ave Unit 4, Chestertown, MD 21620

    Welcome to your new home in the heart of Chestertown Maryland, a charming historic town nestled along the Chester River, known for its vibrant arts scene, waterfront dining, and small-town charm.This beautifully designed property blends modern finishes with timeless appeal. Step inside to find engineered hardwood floors flowing throughout the main living areas, creating both warmth and

    Nick Dively Real Broker, LLC - Annapolis

    104 Maple Ave Unit 4, Chestertown, MD 21620
  • 107 Conley Dr, Chestertown, MD 21620
    107 Conley Dr, Chestertown, MD 21620
    107 Conley Dr, Chestertown, MD 21620
    /16

    $150,000

    Sold May 15, 2026

    107 Conley Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,140 Sq Ft
    • Built 1986

    Last Sold Summary

    • 12% Below List Price
    • $132/SF
    • 32 Days On Market

    Current Estimated Value $159,425

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    107 Conley Dr, Chestertown, MD 21620
    • 21357 Belair Ave, Chestertown, MD 21620
      21357 Belair Ave, Chestertown, MD 21620
      21357 Belair Ave, Chestertown, MD 21620
      /27

      Est $396,109

      Not Listed For Sale

      21357 Belair Ave, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,008 Sq Ft
      • Built 2010
      21357 Belair Ave, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  • 222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    /25

    $320,000

    • 3 Beds
    • 1.5 Baths
    • 1,096 Sq Ft

    222 Dutchess Rd, Chestertown, MD 21620

    Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    222 Dutchess Rd, Chestertown, MD 21620
  • 7501 Church Hill Rd Unit 5, Chestertown, MD 21620
    7501 Church Hill Rd Unit 5, Chestertown, MD 21620
    7501 Church Hill Rd Unit 5, Chestertown, MD 21620
    /17

    $1,800 Per Month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    7501 Church Hill Rd Unit 5, Chestertown, MD 21620

    If you’ve been searching for an open‑concept apartment with a stunning view, your search ends here. This fully renovated third‑floor residence delivers modern style, thoughtful updates, and an airy layout that feels instantly welcoming.Step into a beautifully redesigned kitchen featuring ample cabinetry, upgraded appliances, and a spacious island perfect for cooking, gathering, or

    Amanda Morgan Brenton Realty Group

    7501 Church Hill Rd Unit 5, Chestertown, MD 21620
  • 0 Preston Ln Unit MDKE2006820, Chestertown, MD 21620
    0 Preston Ln Unit MDKE2006820, Chestertown, MD 21620
    0 Preston Ln Unit MDKE2006820, Chestertown, MD 21620
    /41

    $525,000

    Sold Aug 16, 2026

    0 Preston Ln Unit MDKE2006820, Chestertown, MD 21620

    • 3 Beds
    • 3 Baths
    • 2,824 Sq Ft
    • Built 2000

    Last Sold Summary

    • $186/SF
    • 1 Day On Market

    Last Listing Agent Robert G. Shannahan Shoreline Realty

    0 Preston Ln Unit MDKE2006820, 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

      Est $406,513

      Not Listed For Sale

      204 Pine Cove Ln, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,167 Sq Ft
      • Built 2021
      204 Pine Cove Ln, Chestertown, MD 21620

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Kelly Harris Coldwell Banker Realty

  • 7680 Country Club Ln, Chestertown, MD 21620
    7680 Country Club Ln, Chestertown, MD 21620
    7680 Country Club Ln, Chestertown, MD 21620
    /43

    $885,000

    • 5 Beds
    • 4 Baths
    • 2,639 Sq Ft

    7680 Country Club Ln, Chestertown, MD 21620

    Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natural light! Enjoy time on the large screened porch, finished with Ipe hardwood, overlooking the peaceful creek, woods and park like setting. Five bedrooms and 4 full bathrooms, nicely designed with privacy in mind. There's an

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    7680 Country Club Ln, Chestertown, MD 21620
  • 21111 Texas Ave, Chestertown, MD 21620
    21111 Texas Ave, Chestertown, MD 21620
    21111 Texas Ave, Chestertown, MD 21620
    /16

    $350,000

    Sold Mar 05, 2026

    21111 Texas Ave, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 2004

    Last Sold Summary

    • 5% Below List Price
    • $208/SF
    • 17 Days On Market

    Current Estimated Value $354,405

    Last Listing Agent Yvonne Andres Keller Williams Select Realtors of Easton

    21111 Texas Ave, Chestertown, MD 21620
    • 213 Pine Cove Ln, Chestertown, MD 21620
      213 Pine Cove Ln, Chestertown, MD 21620
      213 Pine Cove Ln, Chestertown, MD 21620
      /16

      Est $374,668

      Not Listed For Sale

      213 Pine Cove Ln, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,400 Sq Ft
      • Built 2023
      213 Pine Cove Ln, Chestertown, MD 21620

      Last Sold Summary

      Last Listing Agent Karen Clark Clark & Co Realty, LLC

  • 0 Little Harbor Way Unit 1, Chestertown, MD 21620
    0 Little Harbor Way Unit 1, Chestertown, MD 21620
    0 Little Harbor Way Unit 1, Chestertown, MD 21620
    /25

    $1,459,000

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,231 Sq Ft

    0 Little Harbor Way Unit 1, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,231 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room, with gas fireplace ,to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    0 Little Harbor Way Unit 1, Chestertown, MD 21620
  • 108 Pine St, Chestertown, MD 21620
    108 Pine St, Chestertown, MD 21620
    /2

    $85,000

    Sold Jun 30, 2026

    108 Pine St, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 910 Sq Ft
    • Built 1957

    Last Sold Summary

    • 40% Below List Price
    • $93/SF
    • 6 Days On Market

    Current Estimated Value $117,450

    Last Listing Agent David Moore Real Broker, LLC

    108 Pine St, Chestertown, MD 21620
    • 7499 Poplar Ave, Chestertown, MD 21620
      7499 Poplar Ave, Chestertown, MD 21620
      7499 Poplar Ave, Chestertown, MD 21620
      /34

      Est $279,006

      Not Listed For Sale

      7499 Poplar Ave, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 2018
      7499 Poplar Ave, Chestertown, MD 21620

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Petra Quinn Realty Navigator

  • 104 Landing Ln, Chestertown, MD 21620
    104 Landing Ln, Chestertown, MD 21620
    104 Landing Ln, Chestertown, MD 21620
    /24

    $813,900

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 2,192 Sq Ft

    104 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    104 Landing Ln, Chestertown, MD 21620
  • 704 Truslow Rd, Chestertown, MD 21620
    704 Truslow Rd, Chestertown, MD 21620
    704 Truslow Rd, Chestertown, MD 21620
    /43

    $453,000

    Sold Jul 14, 2026

    704 Truslow Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,060 Sq Ft
    • Built 1992

    Last Sold Summary

    • 3% Above List Price
    • $220/SF
    • 22 Days On Market

    Current Estimated Value $447,484

    Last Listing Agent Crystal Smith RE/MAX Executive

    704 Truslow Rd, Chestertown, MD 21620
    • 142 Church Meadow Ct, Chestertown, MD 21620
      142 Church Meadow Ct, Chestertown, MD 21620
      142 Church Meadow Ct, Chestertown, MD 21620
      /27

      Est $400,105

      Not Listed For Sale

      142 Church Meadow Ct, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,426 Sq Ft
      • Built 2014
      142 Church Meadow Ct, Chestertown, MD 21620

      Last Sold Summary

      • 39 Days On Market

      Last Listing Agent Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

  • 102 Little Harbor Way, Chestertown, MD 21620
    102 Little Harbor Way, Chestertown, MD 21620
    102 Little Harbor Way, Chestertown, MD 21620
    /23

    $839,500

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    102 Little Harbor Way, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    102 Little Harbor Way, Chestertown, MD 21620
  • 10800 Cliff Rd, Chestertown, MD 21620
    10800 Cliff Rd, Chestertown, MD 21620
    10800 Cliff Rd, Chestertown, MD 21620
    /94

    $1,524,900

    Sold Feb 17, 2026

    10800 Cliff Rd, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 5,241 Sq Ft
    • Built 1997

    Last Sold Summary

    • 2% Above List Price
    • $291/SF
    • 5 Days On Market

    Current Estimated Value $1,491,124

    Last Listing Agent Lona Todd Taylor Properties

    10800 Cliff Rd, Chestertown, MD 21620
    • 106 Church Aly, Chestertown, MD 21620
      106 Church Aly, Chestertown, MD 21620
      106 Church Aly, Chestertown, MD 21620
      /27

      Est $483,243

      Not Listed For Sale

      106 Church Aly, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 1,416 Sq Ft
      • Built 1880
      106 Church Aly, Chestertown, MD 21620

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Cindy Genther Rock Hall Properties Real Estate

Showing Results 1 - 40, Page 1 of 18

Maryland Kent County

Real Estate & Homes

Home Prices in Chestertown, MD

The median home sale price in Chestertown, MD is $367,500, up 2% year-over-year. Homes in Chestertown sell in 48 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$367,500
Median Single Family Sale Price
$386,200
Median Townhouse Sale Price
$264,900
Median 2 Bedroom Sale Price
$359,000
Median 1 Bedroom Sale Price
$295,000
Average Price Per Sq Ft
$217
Number of Homes for Sale
33
Last 12 months Home Sales
104
Months of Supply
3.80
Median List Price
$375,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
2%
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