Recently Sold Chestertown Homes

• 

  

  

  /17

  $283,000 Sold Feb 19, 2025

  • 1,840 Sq Ft
  • $154/SF
  • 38 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2003

  104 Oak Leaf Dr, Chestertown, MD 21620

  Welcome to your new home in the vibrant community of Chestertown! This beautiful 3-bedroom, 3.5-bath townhome features an open layout perfect for modern living. The heart of the home is the stylish kitchen, equipped with contemporary finishes and ample storage.Enjoy relaxing in the spacious living area or step outside to your private deck—ideal for entertaining or soaking up the sun. The

  Krystal Zellner Crown Homes Real Estate

  104 Oak Leaf Dr, Chestertown, MD 21620
• Selling your home? Sell it faster and for more with a Homes.com Boost.

  Learn More
• 

  

  

  /29

  $600,000 Sold Feb 06, 2025

  • 2,672 Sq Ft
  • $225/SF
  • 155 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2007

  110 Birch Run Rd, Chestertown, MD 21620

  CUSTOM - BUILT 4 BEDROOM/3 BATH CUSTOM BUILT CONTEMPORARY on a corner .37acre lot in the desirable neighborhood of Mile Tree Village. This gorgeous, meticulously maintained home offers all on one floor living in light-filled open floor plan comfort. Features include cathedral and vaulted ceilings in the main living area and master bedroom; handsome maple flooring throughout the central living

  Paula Ruckelshaus Long & Foster Real Estate, Inc.

  110 Birch Run Rd, Chestertown, MD 21620
• 

  

  

  /57

  $427,000 Sold Jan 29, 2025

  • 1,995 Sq Ft
  • $214/SF
  • 1 Day On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1997

  313 S Queen St, Chestertown, MD 21620

  Amazing opportunity to own a lovely townhouse, located in a row of 6 charming townhomes across from Wilmer Park with water views of the Chester River. No HOA or dues. Walk to restaurants, quaint shops and art galleries downtown or walk over to the Chestertown Marina just a couple of minutes away. Inside you will find an updated kitchen with open access to the dining area and vaulted living

  Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

  313 S Queen St, Chestertown, MD 21620
• 

  

  

  /43

  $355,000 Sold Jan 10, 2025

  • 1,672 Sq Ft
  • $212/SF
  • 0 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2023

  106 Silver Heel Rd, Chestertown, MD 21620

  Looking for a Brand New home without the hassle of building? You have found it! Built in 2023 in the wonderful neighborhood known as The Villages of Chestertown. This gorgeous 3 bedroom, 2.5 bathroom home was designed with luxury and quality in mind. As soon as you step inside you will admire the open floor plan featuring a shiplap accent wall around the fireplace. The dining area connects

  Chuck Zepp EXP Realty, LLC

  106 Silver Heel Rd, Chestertown, MD 21620
• 

  

  

  /12

  $212,000 Sold Dec 30, 2024

  • 1,275 Sq Ft
  • $166/SF
  • 16 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1959

  111 Elm St, Chestertown, MD 21620

  Great opportunity to own in the College Heights subdivision across from Washington College. A few improvements would make this rancher a cozy home. One level living offers a living room, kitchen, 3 bedrooms and 1 bathroom. 2 enclosed porches present additional living space for an office, family room or game room. The exterior is brick with a newer roof. The home is situated on a large, level lot,

  Andy Batch Keller Williams Select Realtors of Annapolis

  111 Elm St, Chestertown, MD 21620
• 

  

  /27

  $247,500 Sold Dec 18, 2024

  • 1,260 Sq Ft
  • $196/SF
  • 30 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 2022

  117 Chester Arms Dr, Chestertown, MD 21620

  Discover this nearly new, beautifully maintained home in Chestertown. Featuring luxury vinyl flooring throughout, white cabinets, granite countertops, a spacious living room, an eat-in kitchen area, and a covered patio, this home offers a comfortable and stylish living space. The large primary bedroom suite and additional spacious bedrooms provide ample room for relaxation and

  David Moore Real Broker, LLC

  117 Chester Arms Dr, Chestertown, MD 21620
• 

  

  /36

  $660,000 Sold Dec 16, 2024

  • 3,444 Sq Ft
  • $192/SF
  • 56 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2003

  8774 Orchard Dr, Chestertown, MD 21620

  First time to ever be offered on the market. Nestled in a picturesque neighborhood, this contemporary home is a testament to luxury and functionality. Spanning over 3,400 square feet, this meticulously maintained home has so much to offer. Spacious Living Areas: Open-concept layout with hard wood floors, high ceilings and abundant natural light, complemented by 2 gas fireplaces for cozy

  Jennifer Thomas RE/MAX Executive

  8774 Orchard Dr, Chestertown, MD 21620
• 

  

  /27

  $495,000 Sold Dec 13, 2024

  • 1,416 Sq Ft
  • $350/SF
  • 7 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1880

  106 Church Alley, Chestertown, MD 21620

  Step into this beautifully renovated 1,416 sq. ft., 2 bedrooms, 1.5 bath home in the heart of Chestertown. The building operated as the Johnson General Store into the 1950s and this home now offers the perfect blend of historical charm and modern conveniences. Fully restored in 2017 down to the studs, this home retains its rich heritage while boasting high-end updates throughout. As you enter

  Cindy Genther Rock Hall Properties Real Estate

  106 Church Alley, 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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /50

  $501,000 Sold Nov 14, 2024

  • 2,208 Sq Ft
  • $227/SF
  • 35 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1984

  217 Birch Run Rd, Chestertown, MD 21620

  Price improvement! Beautiful cape in the coveted Mile Tree Village with a lovely in-ground pool surrounded by a spacious patio. Large flowing rooms with lots of built-ins. Half bath on the main floor. Second floor has 4 bedrooms, 2 baths, laundry, and an unfinished bonus or storage room. Home needs some finishing touches from its new owners but a little effort will yield big rewards with this

  Peter Heller Coldwell Banker Chesapeake Real Estate Company

  217 Birch Run Rd, Chestertown, MD 21620
• 

  

  /56

  $866,395 Sold Nov 14, 2024

  • 3,355 Sq Ft
  • $258/SF
  • 130 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1936

  307 Washington Ave, Chestertown, MD 21620

  This stunning renovation is the jewel of Chestertown's revitalized upper historic district! A beautiful view of Washington College (9th best college in the country by Princeton Review), invites a walk around campus, to the river, or to the shops & restaurants in between. Extensive interior & exterior renovations along with plumbing, mechanical, and electrical upgrades throughout make the beauty

  Beth Ostrander Doug Ashley Realtors, LLC

  307 Washington Ave, Chestertown, MD 21620
• 

  

  /35

  $406,000 Sold Nov 07, 2024

  • 1,509 Sq Ft
  • $269/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2002

  813 S Meadowview Dr, Chestertown, MD 21620

  Nestled on the edge of the desirable Crestview neighborhood, this main level living home boasts beautiful hardwood floors, an easy flow perfect for entertaining, an ample screened in porch with views of the wooded back yard, and a walk-out, unfinished basement perfect for a gardening room or enclosed storage. Roof is only a few years young! Open house on Sept. 29th, 1-3pm.

  Liddy Campbell TTR Sotheby's International Realty

  813 S Meadowview Dr, 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
• 

  /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
• 

  /2

  $90,000 Sold May 30, 2025

  • Land
  • 13.46 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
• 

  /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

Showing Results 41 - 59, Page 2 of 2