188

Recently Sold Chestertown, MD Homes

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  • 10719 Mallard Point Rd, Chestertown, MD 21620
    10719 Mallard Point Rd, Chestertown, MD 21620
    10719 Mallard Point Rd, Chestertown, MD 21620
    /26

    $355,000 Sold Sep 06, 2024

    • 1,344 Sq Ft
    • $264/SF
    • 15 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2015

    10719 Mallard Point Rd, Chestertown, MD 21620

    Welcome to this charming raised rancher, built in 2015and located in the water-privileged community of Chesapeake Landing. This beautiful home features 3 spacious bedrooms and a desirable split bedroom floor plan, offering privacy and comfort for all. The open floor plan creates a seamless flow from room to room, enhancing both functionality and style, and offers a large kitchen with stainless

    Sarah King Cross Street Realtors LLC

    10719 Mallard Point Rd, Chestertown, MD 21620
  • 308 Landing Ln Unit 17, Chestertown, MD 21620
    308 Landing Ln Unit 17, Chestertown, MD 21620
    308 Landing Ln Unit 17, Chestertown, MD 21620
    /6

    $782,200 Sold Sep 03, 2024

    • 6 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2014

    308 Landing Ln Unit 17, Chestertown, MD 21620

    Carefree waterfront living within a short stroll or bike ride to Charming Historic Downtown Chestertown, Washington College and the Chester River Yacht and Country Club. This home offers some of the finest waterfront views in the entire Chester River Landing Community. Just imagine a front row seat to the annual Chestertown Fourth of July fireworks, broad views of the Schooner Sultana sailing to

    William Norris Select Land & Homes, LLC

    308 Landing Ln Unit 17, Chestertown, MD 21620
  • 123 High St, Chestertown, MD 21620
    123 High St, Chestertown, MD 21620
    123 High St, Chestertown, MD 21620
    /29

    $865,000 Sold Aug 30, 2024

    • 1,855 Sq Ft
    • $466/SF
    • 25 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1870

    123 High St, Chestertown, MD 21620

    This exquisitely renovated 1800s home showcases the timeless elegance of its original architecture. Every detail has been restored to its former glory. No expense has been spared in selecting the finest finishes and materials for this renovation and it extends beyond the interior, with the creation of an outdoor oasis. This meticulously landscaped gardens and charming patio provide a private

    John Burke Gunther-McClary Real Estate

    123 High St, Chestertown, MD 21620
  • 6595 Quaker Neck Rd, Chestertown, MD 21620
    6595 Quaker Neck Rd, Chestertown, MD 21620
    6595 Quaker Neck Rd, Chestertown, MD 21620
    /27

    $75,000 Sold Aug 29, 2024

    • 3,090 Sq Ft
    • $24/SF
    • 5 Days On Market
    • 2 Baths
    • Built 1851

    6595 Quaker Neck Rd, Chestertown, MD 21620

    Historic Bond Chapel Church built in 1851. Located in rural location. Would be a good candidate for residential conversion. Large addition of 1652 sq. ft. frame construction,, formerly housed the Sunday School rooms, kitchen and fellowship hall, has two half baths. The sanctuary, built in 1851 is of brick construction. The chapel is simple in design and contains 1656 sq. ft. These two

    Cynthia Stevens Wilson Realty

    6595 Quaker Neck Rd, Chestertown, MD 21620
  • 8757 Orchard Dr, Chestertown, MD 21620
    8757 Orchard Dr, Chestertown, MD 21620
    8757 Orchard Dr, Chestertown, MD 21620
    /49

    $460,000 Sold Aug 29, 2024

    • 2,210 Sq Ft
    • $208/SF
    • 128 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1992

    8757 Orchard Dr, Chestertown, MD 21620

    Welcome to your tranquil retreat at Orchard Hill, where modern sophistication meets peaceful living on 1.89 acres of beautifully landscaped grounds and located just minutes from Historic downtown Chestertown. Community living without any HOA restrictions. This stunning Cape Cod style home offers an abundance of amenities and thoughtful details throughout. Property provides ample space to expand

    Ken Roderick Chesapeake Real Estate Associates, LLC

    8757 Orchard Dr, Chestertown, MD 21620
  • 8049 Quaker Neck Rd, Chestertown, MD 21620
    8049 Quaker Neck Rd, Chestertown, MD 21620
    8049 Quaker Neck Rd, Chestertown, MD 21620
    /28

    $848,000 Sold Aug 28, 2024

    • 1,660 Sq Ft
    • $511/SF
    • 98 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1945

    8049 Quaker Neck Rd, Chestertown, MD 21620

    Beautifully renovated waterfront on the Chester River, located between historic downtown Chestertown and the Chester River Yacht and Country Club. Renovations include including new kitchen and bathrooms. This property boasts a deep water dock with lift for your boating, swimming and fishing pleasures. Come and enjoy all the Chestertown has to offer with just a short walk to down town shops,

    John Burke Gunther-McClary Real Estate

    8049 Quaker Neck Rd, Chestertown, MD 21620
  • 217 Radcliffe Dr, Chestertown, MD 21620
    217 Radcliffe Dr, Chestertown, MD 21620
    217 Radcliffe Dr, Chestertown, MD 21620
    /37

    $564,500 Sold Aug 19, 2024

    • 1,467 Sq Ft
    • $385/SF
    • 6 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2003

    217 Radcliffe Dr, Chestertown, MD 21620

    Beautifully maintained home tucked away on a quiet cul-de-sac but still within walking distance to downtown shops, restaurants, and riverfront. Open floor plan with 9ft ceilings in the living room. 3 bedrooms and 2 full bath with a 2 car attached garage. Covered front porch, secluded screened-in rear porch. Nicely landscaped. Schedule your personal tour!

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    217 Radcliffe Dr, Chestertown, MD 21620
  • 8842 Fairlee Rd, Chestertown, MD 21620
    8842 Fairlee Rd, Chestertown, MD 21620
    8842 Fairlee Rd, Chestertown, MD 21620
    /13

    $221,000 Sold Aug 15, 2024

    • Land
    • 5 Acres
    • $41,231 per Acre
    • 7 Days On Market

    8842 Fairlee Rd, Chestertown, MD 21620

    Here's a chance to build your dream home just minutes from historic Chestertown or Rock Hall. There was a house fire on this property and the remains have been taken away leaving only a pole barn on over 5 acres that was once used as an orchard and is now mainly cleared. Public Water and Sewer are huge benefits to the design and construction process. The oversized pole barn was recently put up

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    8842 Fairlee Rd, Chestertown, MD 21620
  • 201 Tamarack Rd, Chestertown, MD 21620
    201 Tamarack Rd, Chestertown, MD 21620
    201 Tamarack Rd, Chestertown, MD 21620
    /50

    $342,000 Sold Aug 14, 2024

    • 1,225 Sq Ft
    • $279/SF
    • 1 Day On Market
    • 2 Beds
    • 2 Baths
    • Built 1973

    201 Tamarack Rd, Chestertown, MD 21620

    Discover the charm and tranquility of this inviting ranch-style home, perfectly situated on the Queen Anne's County side of Chestertown, Maryland. Just steps from Rosin Creek, this property offers not only spacious living but also exciting opportunities for canoeing, boating, fishing, and crabbing on the beautiful Chester River.Step inside to find large, airy bedrooms, a generously sized

    Petra Quinn Realty Navigator

    201 Tamarack Rd, Chestertown, MD 21620
  • 23120 Club Terrace, Chestertown, MD 21620
    23120 Club Terrace, Chestertown, MD 21620
    23120 Club Terrace, Chestertown, MD 21620
    /41

    $365,000 Sold Aug 13, 2024

    • 1,789 Sq Ft
    • $204/SF
    • 12 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1969

    23120 Club Terrace, Chestertown, MD 21620

    Discover your dream home nestled in a serene water-privileged community with exclusive access to a boat ramp, a small marina, and picturesque walking trails. This inviting 3-bedroom, 2-bath residence offers an ideal blend of comfort, convenience, and outdoor living, all situated on a generous 1-acre property composed of two separate parcels.Enjoy the spacious primary suite with new carpet, a

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    23120 Club Terrace, Chestertown, MD 21620
  • 332 Truslow Rd, Chestertown, MD 21620
    332 Truslow Rd, Chestertown, MD 21620
    332 Truslow Rd, Chestertown, MD 21620
    /29

    $252,400 Sold Aug 12, 2024

    • 1,408 Sq Ft
    • $179/SF
    • 118 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1900

    332 Truslow Rd, Chestertown, MD 21620

    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 Accented Gas Fireplace * Updated Kitchen with Stainless Steel Appliances * Separate Laundry Room off Kitchen * 2 Generous Sized Upper Level Bedrooms + a

    James Blackwell Blackwell Real Estate, LLC

    332 Truslow Rd, Chestertown, MD 21620
  • 415 Fairview Dr, Chestertown, MD 21620
    415 Fairview Dr, Chestertown, MD 21620
    415 Fairview Dr, Chestertown, MD 21620
    /24

    $718,000 Sold Aug 09, 2024

    • 1,376 Sq Ft
    • $522/SF
    • 16 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1973

    415 Fairview Dr, Chestertown, MD 21620

    Eastern Shore of Maryland Waterfront Cottage is perched on the banks of Rosin Creek in Queen Anne’s County. Cozy, comfortable home welcomes you with wrap-around waterviews in a serene wooded setting. With convenient single level living, the three bedroom one-and-half bath home offers an open flowing floorplan bright with natural light and custom wood detail. Relax and enjoy views from the

    Richard Budden Coldwell Banker Chesapeake Real Estate Company

    415 Fairview Dr, Chestertown, MD 21620
  • 0 Georgetown Rd SE Unit MDKE2004164, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2004164, Chestertown, MD 21620
    /2

    $40,000 Sold Aug 05, 2024

    • Land
    • 4.03 Acres
    • $9,926 per Acre
    • 26 Days On Market

    0 Georgetown Rd SE Unit MDKE2004164, Chestertown, MD 21620

    Wow 4 acres of privacy and public utilities available! Located just outside of Chestertown in Fairlee. Accessible through a 50' right of way shown in survey. Buyer to verify right of way and utilities. Call today!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Georgetown Rd SE Unit MDKE2004164, Chestertown, MD 21620
  • 10550 Klamath Rd, Chestertown, MD 21620
    10550 Klamath Rd, Chestertown, MD 21620
    10550 Klamath Rd, Chestertown, MD 21620
    /33

    $305,000 Sold Aug 02, 2024

    • 1,404 Sq Ft
    • $217/SF
    • 2 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2006

    10550 Klamath Rd, Chestertown, MD 21620

    Immerse yourself in waterfront living at this captivating Cape Cod in the sought-after Chesapeake Landing community! Embrace serenity with 3 bedrooms and 2 full baths, including a luxurious main-floor primary suite. Brand new luxury vinyl plank flooring flows throughout, creating a cohesive and modern feel. Unwind in the light-filled living area or prepare culinary delights in the updated kitchen

    David Moore RE/MAX Executive

    10550 Klamath Rd, Chestertown, MD 21620
  • 209 N Water St, Chestertown, MD 21620
    209 N Water St, Chestertown, MD 21620
    /2

    $1,100,000 Sold Jun 30, 2025

    • 2,909 Sq Ft
    • $378/SF
    • 0 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1900

    209 N Water St, Chestertown, MD 21620

    One of the "stand-out" North Water Street waterfront homes in Historic Chestertown that has raised children, hosted town development meetings, entertained many, and most recently provided the perfect escape for a loving three-generation family. The house is "old bones with refreshed skin" in many parts of this three-story traditional Four Square and full, multi-room basement. What distinguishes

    Richard Keaveney Cross Street Realtors LLC

    209 N Water St, Chestertown, MD 21620
  • 107 N Queen St, Chestertown, MD 21620
    107 N Queen St, Chestertown, MD 21620
    /2

    $539,000 Sold Jun 16, 2025

    • 3,050 Sq Ft
    • $177/SF
    • 1 Day On Market
    • 4 Beds
    • 2 Baths
    • Built 1879

    107 N Queen St, Chestertown, MD 21620

    The Vannort House stands proudly on historic Queen Street with a colonial-era smokehouse in the yard! Light & breezy: The 31' long screened-in side-porch has doors from the eat-in Kitchen, formal Dining Room, and the grand high-ceilinged Living Room! Keep all the doors open into the screened porch for an amazing indoor-outdoor way of living! A truly versatile layout for entertaining and

    Beth Ostrander Doug Ashley Realtors, LLC

    107 N Queen St, Chestertown, MD 21620
  • 0 None Unit MDKE2005014, Chestertown, MD 21620
    0 None Unit MDKE2005014, Chestertown, MD 21620
    /2

    $90,000 Sold May 30, 2025

    • Land
    • 13 Acres
    • $6,686 per Acre
    • 0 Days On Market

    0 None Unit MDKE2005014, Chestertown, MD 21620

    13.5 wooded acres with very limited access on north side of Chestertown. Should be excellent deer hunting. 16' paper right of way to access.

    William Norris Select Land & Homes, LLC

    0 None Unit MDKE2005014, Chestertown, MD 21620
  • 226 Blakefield Dr, Chestertown, MD 21620
    226 Blakefield Dr, Chestertown, MD 21620
    /2

    $539,000 Sold Mar 31, 2025

    • 2,400 Sq Ft
    • $225/SF
    • 4 Beds
    • 3 Baths
    • Built 2025

    226 Blakefield Dr, Chestertown, MD 21620

    New Construction Sold in the Blakefield Community . 4 Bedrooms, 3 Full Baths

    datacorrect BrightMLS Non Subscribing Office

    226 Blakefield Dr, Chestertown, MD 21620
  • 833 Woods Rd, Chestertown, MD 21620
    833 Woods Rd, Chestertown, MD 21620
    /2

    $155,000 Sold Dec 17, 2024

    • Land
    • 3.00 Acres
    • $51,667 per Acre
    • 13 Days On Market

    833 Woods Rd, Chestertown, MD 21620

    Nice wooded 3-acre lot to build your dream home! Close to Chestertown and Rt 301 for commuters. The lot has perc and septic already exists. Some of the lot has been cleared where home can be built.

    Tina Brown Benson & Mangold, LLC

    833 Woods Rd, Chestertown, MD 21620
  • 0 Glenola Rd, Chestertown, MD 21620
    0 Glenola Rd, Chestertown, MD 21620
    /2

    $20,000 Sold Dec 13, 2024

    • Land
    • 0.35 Acre
    • $57,143 per Acre
    • 112 Days On Market

    0 Glenola Rd, Chestertown, MD 21620

    Perc approved lot for sale in Chesapeake Landing. A total of .34 combined with both lots. Community has a voluntary HOA giving you access to the boat ramp, marina and a slip for an extra fee.

    John Burke Gunther-McClary Real Estate

    0 Glenola Rd, Chestertown, MD 21620
  • 7517 Sunburst Ave, Chestertown, MD 21620
    7517 Sunburst Ave, Chestertown, MD 21620
    /2

    $254,900 Sold Nov 27, 2024

    • 1,320 Sq Ft
    • $193/SF
    • 13 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2020

    7517 Sunburst Ave, Chestertown, MD 21620

    Almost new home in Chestertown! Modern three bed, two bath rancher with split floor plan. Open kitchen living space features LVP flooring, kitchen island, stainless steel appliances, and large windows with lots of sunlight streaming in! Come check it out today!

    John Carroll Village Real Estate Company LLC

    7517 Sunburst Ave, Chestertown, MD 21620
  • 340 Cannon St, Chestertown, MD 21620
    340 Cannon St, Chestertown, MD 21620
    /2

    $255,000 Sold Nov 15, 2024

    • 1,582 Sq Ft
    • $161/SF
    • 4 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1920

    340 Cannon St, Chestertown, MD 21620

    Location! Location! Location! *** Great Investment Opportunity *** Just one block from the heart of Historic Chestertown, this spacious victorian home is waiting for your personal touch and TLC. Property has 3 bedrooms, 1 full bathroom (on the upper level) and 1 half bathroom (on the main level). This home also offers an amazing element of surprise in the attic space which can be converted

    Kysha Merritt Samson Properties

    340 Cannon St, Chestertown, MD 21620
  • 0 Fall St Unit MDKE2004200, Chestertown, MD 21620
    0 Fall St Unit MDKE2004200, Chestertown, MD 21620
    /2

    $6,000 Sold Nov 07, 2024

    • Land
    • 0.31 Acre
    • $19,355 per Acre
    • 62 Days On Market

    0 Fall St Unit MDKE2004200, Chestertown, MD 21620

    Six lots combined into one .3 acre property. Walking distance to the Chesapeake Bay, Tolchester beach, marina and Shanty. The county says sewer hook up is not available.

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Fall St Unit MDKE2004200, Chestertown, MD 21620
  • 211 N Lynchburg St, Chestertown, MD 21620
    211 N Lynchburg St, Chestertown, MD 21620
    /2

    $7,200 Sold Oct 31, 2024

    • Land
    • 0.03 Acre
    • $240,000 per Acre
    • 35 Days On Market

    211 N Lynchburg St, Chestertown, MD 21620

    This 20'x64' lot is located just outside of downtown Chestertown attractions. A Chesterown zoning administrator said "A prospective buyer would have to get a variance from the Board of Zoning Appeals, which would almost certainly be granted. " Public utilities are available. Priced to sell!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    211 N Lynchburg St, Chestertown, MD 21620
  • 241 Duke of Kent St, Chestertown, MD 21620
    241 Duke of Kent St, Chestertown, MD 21620
    /2

    $369,000 Sold Aug 05, 2024

    • 1,494 Sq Ft
    • $247/SF
    • 3 Beds
    • 2 Baths
    • Built 1999

    241 Duke of Kent St, Chestertown, MD 21620

    Well maintained home in Queen Anne's County featuring 3 bedrooms, 2 full baths, separate dining room as well as an eat-in kitchen. Full size laundry room with exterior exit to the partially fenced back yard and an oversized 2 car garage with room for vehicles and storage. The entire home has been freshly painted and has all new carpet, and new flooring in the kitchen, laundry, and bathrooms.

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    241 Duke of Kent St, Chestertown, MD 21620
  • 101 Rivershore Rd, Chestertown, MD 21620
    101 Rivershore Rd, Chestertown, MD 21620
    /2

    $1,125,000 Sold Jun 10, 2025

    • 1,968 Sq Ft
    • $572/SF
    • 3 Beds
    • 2 Baths
    • Built 1950

    101 Rivershore Rd, Chestertown, MD 21620

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    101 Rivershore Rd, Chestertown, MD 21620
  • 0 Georgetown Rd SE Unit MDKE2004670, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2004670, Chestertown, MD 21620
    /2

    $330,000 Sold Nov 20, 2024

    • Land
    • 41 Acres
    • $8,065 per Acre

    0 Georgetown Rd SE Unit MDKE2004670, Chestertown, MD 21620

    Jim Bim Winning Edge

    0 Georgetown Rd SE Unit MDKE2004670, Chestertown, MD 21620
  • 23693 L Rd, Chestertown, MD 21620
    23693 L Rd, Chestertown, MD 21620
    /2

    $18,000 Sold Sep 06, 2024

    • Land
    • 2.00 Acres
    • $9,000 per Acre
    • 409 Days On Market

    23693 L Rd, Chestertown, MD 21620

    Dee Dee Miller Long & Foster Real Estate, Inc.

    23693 L Rd, Chestertown, MD 21620

Showing Results 161 - 188, Page 5 of 5

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Recently Sold Real Estate & Homes in Chestertown, MD

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