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Recently Sold Kingstown Homes

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  • /2

    $119,500 Sold Jun 26, 2025

    • Land
    • 1.01 Acres
    • $118,317 per Acre
    • 2 Days On Market

    205 River Rd, Chestertown, MD 21620

    A perc approved one acre open lot in a an established neighborhood ready for your dream home. No trees to clear and no restrictions except Critical Area guidelines. Perfectly located within a couple of minutes to downtown Historic Chestertown.

    Hayley Norris Select Land & Homes, LLC

    205 River Rd, Chestertown, MD 21620
  • /24

    $344,900 Sold Jun 25, 2025

    • 1,344 Sq Ft
    • $257/SF
    • 24 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1993

    109 Edmore Rd, Chestertown, MD 21620

    Welcome to 109 Edmore Rd, a beautifully renovated 3-bedroom, 2-bath ranch-style home offering 1,344 sq. ft. of comfortable living space on a 0.34-acre lot. This move in ready home blends modern upgrades with cozy charm. Renovated in 2021 upgrades include HVAC, Roof, Encapsulated crawl space, appliances, reverse osmosis and water conditioner. Features a 16 x 12 screen porch for relaxing outdoors.

    Norma Coursey Benson & Mangold, LLC

    109 Edmore Rd, Chestertown, MD 21620
  • /23

    $312,000 Sold Jun 20, 2025

    • 1,188 Sq Ft
    • $263/SF
    • 21 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1989

    104 Dutchess Rd, Chestertown, MD 21620

    This home is a must see! Join the Chester Harbor Community.A charming home in a lovely neighborhood on Maryland's Eastern Shore. Welcome to Chester Harbor, Queen Anne's County. Only minutes from historic Chestertown, this three bedroom, two bath home offers one-level living and an appealing owner's suite. The expansive, fully fenced backyard is easily accessed from the private deck off of the

    Helen J Butler Taylor Properties

    104 Dutchess Rd, Chestertown, MD 21620
  • /25

    $385,000 Sold Apr 11, 2025

    • 1,811 Sq Ft
    • $213/SF
    • 19 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1982

    149 Longfellow Dr, Chestertown, MD 21620

    Welcome to your dream home in the charming sought after community of Chester Harbor! This delightful property boasts 3 spacious bedrooms and 2 full updated bathrooms, perfectly designed for comfort and modern living.Step into the huge master bedroom, perfect for all buyers. The finished basement provides versatile additional living space—ideal for a family room, home office, or play area.The

    Isaac Bahary KW Empower

    149 Longfellow Dr, Chestertown, MD 21620
  • /41

    $385,000 Sold Apr 04, 2025

    • 1,560 Sq Ft
    • $247/SF
    • 69 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1977

    109 Secor Rd, Chestertown, MD 21620

    Charming Home in Chester Harbor with Water Access!Welcome to 109 Secor Rd, Chestertown, MD 21620, nestled on a peaceful cul-de-sac in the desirable water-access community of Chester Harbor on the Queen Anne’s side of the Chester River. This home offers a perfect blend of comfort, charm, and recent updates, making it an exceptional choice for your next chapter.Key

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    109 Secor Rd, Chestertown, MD 21620
  • /39

    $355,000 Sold Mar 31, 2025

    • 1,200 Sq Ft
    • $296/SF
    • 19 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1991

    105 Justin Buch Dr, Chestertown, MD 21620

    Welcome to 105 Justin Buch Drive, a delightful single-family home nestled in a quiet community on the Queen Anne's side of Chestertown, MD. This charming residence offers 3 spacious bedrooms and 2 full bathrooms, providing ample space for comfortable living. Buy with ease with this recently renovated home within the last 3 years, to include a new roof, HVAC, Kitchen backsplash, new garage

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    105 Justin Buch Dr, Chestertown, MD 21620
  • /22

    $319,000 Sold Mar 31, 2025

    • 1,188 Sq Ft
    • $269/SF
    • 49 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1985

    201 Fairview Dr, Chestertown, MD 21620

    Welcome to Chester Harbor. Great starter or downsizer, 3 bed 2 bath rancher awaits new owners. The floor plan includes generous Eat -in kitchen and large living room, separate laundry, and a huge screened in porch for picking crabs, parties, or just relaxing. New flooring , fresh paint, and new kitchen counters are a few of the recent updates. Tree lined rear yard and front holly hedge

    Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

    201 Fairview Dr, Chestertown, MD 21620
  • /28

    $343,600 Sold Mar 26, 2025

    • 1,556 Sq Ft
    • $221/SF
    • 14 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2000

    249 Duke of Kent St, Chestertown, MD 21620

    Lovely all one floor living in quiet neighborhood with updated features throughout! Brand new gorgeous kitchen with white shaker cabinetry featuring dovetail construction soft close drawers, solid butcher block countertops, tile backsplash, large island, brand new stainless steel appliances and much more! eng hardwood flooring, recessed lighting, vertical custom ship lap, gas fireplace, screened

    Lee Wolff FSBO Broker

    249 Duke of Kent St, Chestertown, MD 21620
  • /29

    $380,000 Sold Mar 14, 2025

    • 1,800 Sq Ft
    • $211/SF
    • 118 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1998

    409 Riverview Rd, Chestertown, MD 21620

    EXCEPTIONAL VALUE-This charming Cape Cod home offers exceptional value with a recent $10,000 price reduction and new carpet throughout. Located on a desirable corner lot in Kingstown, this property is just a short walk or bike ride from historic Chestertown. The home features a modernized kitchen, updated bathrooms, and custom tile floors. Enjoy the convenience of a first-floor bedroom, a

    Norma Coursey Benson & Mangold, LLC

    409 Riverview Rd, Chestertown, MD 21620
  • /87

    $440,000 Sold Mar 13, 2025

    • 1,848 Sq Ft
    • $238/SF
    • 31 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1987

    312 Princess Anne Dr, Chestertown, MD 21620

    ?? Just Renovated Creekside Beauty – Move-In Ready! ??Discover your dream home with this beautifully renovated 4-bedroom, 2.5-bath gem that overlooks a serene creek. Perfectly blending modern upgrades with cozy charm, this property has everything you need and more!? Key Features:Spacious 2-Car GarageBonus Room: Use as a 4th bedroom, home office, or entertainment

    Jim Davidson Coldwell Banker Waterman Realty

    312 Princess Anne Dr, Chestertown, MD 21620
  • /21

    $305,000 Sold Feb 27, 2025

    • 1,028 Sq Ft
    • $297/SF
    • 13 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1976

    116 Fairview Dr, Chestertown, MD 21620

    Move-in ready and waiting for you! Start the new year in this charming 3-bedroom, 1-bath rancher. The brand-new kitchen is a showstopper, featuring sleek granite countertops, stylish new cabinets, and stainless steel appliances. Durable and attractive LVP flooring flows seamlessly throughout the home, creating a low-maintenance living space. Freshly painted from top to bottom, this home feels

    Jody Baker Cross Street Realtors LLC

    116 Fairview Dr, Chestertown, MD 21620
  • /15

    $325,000 Sold Feb 27, 2025

    • 2,460 Sq Ft
    • $132/SF
    • 112 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1972

    117 Primrose Rd, Chestertown, MD 21620

    Ranch home located in Primrose Point neighborhood( Queen Anne's County with Chestertown address), only ten minutes from downtown Chestertown. This home offers large rooms that could be modified to create a formal dining room and seperate family room if desired. The swimming pool has not been used for two years. This property is being sold "AS-IS". Sign posted.

    Herschell Claggett Davis Real Estate, Inc.

    117 Primrose Rd, Chestertown, MD 21620
  • /10

    $390,000 Sold Feb 06, 2025

    • Land
    • 2.30 Acres
    • $169,565 per Acre
    • 322 Days On Market

    0 Truslow Farm Ln, Chestertown, MD 21620

    Opportunity to claim your own 2.3 acres of waterfront situated amidst the serene beauty of Truslow farm. This parcel represents one of the last untouched waterfront canvases on the Chester River, eagerly awaiting your imagination to bring it to life as your dream home or waterfront escape. Located just across the river from the vibrant events of the Sultana, Downrigging, Tea Party festivals, and

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Truslow Farm Ln, Chestertown, MD 21620
  • /48

    $350,000 Sold Dec 30, 2024

    • 2,102 Sq Ft
    • $167/SF
    • 50 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1976

    125 Primrose Rd, Chestertown, MD 21620

    **Seller has purchased a new dishwasher and it will be installed in the coming days. Tucked away in a wooded setting in a quiet neighborhood just a block off the Chester River you will find this well built welcoming home. The well designed main floor layout includes a living room, dining room, and eat in kitchen plus a year round spacious sunroom overlooking the back yard and the open space

    Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

    125 Primrose Rd, Chestertown, MD 21620
  • /30

    $649,000 Sold Dec 20, 2024

    • 1,680 Sq Ft
    • $386/SF
    • 27 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1977

    411 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 water views in a serene wooded setting. With convenient single level living, the three bedroom two bathroom home offers a flowing floor plan bright with natural light and custom upgrades. Relax and enjoy views from the private walkout

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    411 Fairview Dr, Chestertown, MD 21620
  • /80

    $385,000 Sold Dec 20, 2024

    • 2,240 Sq Ft
    • $172/SF
    • 35 Days On Market
    • 5 Beds
    • 2 Baths
    • Built 1969

    221 River Rd, Chestertown, MD 21620

    Hidden within the wandering gardens, you will find this meticulously maintained home with seasonal water views of the Chester River in a quiet family-friendly community just minutes from Chestertown. The spacious front and back yards are private oases with just about every tree or plant one can think of; a true gardner's dream. Enjoy the fall colors from the back screened-in porch. Inside you

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    221 River Rd, Chestertown, MD 21620
  • /26

    $325,000 Sold Dec 12, 2024

    • 1,500 Sq Ft
    • $217/SF
    • 25 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1974

    228 Concord Rd, Chestertown, MD 21620

    This 1500 sq. foot rancher sits on a nice open lot with plenty of parking and room to grow and make your own . Main level offers eat in kitchen, an oversized living room with fireplace , four bedrooms and two full baths. One of the bedrooms could make a perfect home office. This home has been freshly painted and new flooring. This will get the new owners a fresh start while they decide on

    Grace Crockett Doug Ashley Realtors, LLC

    228 Concord Rd, Chestertown, 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
  • /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
  • /25

    $349,000 Sold Nov 08, 2024

    • 1,232 Sq Ft
    • $283/SF
    • 6 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2024

    121 Fairview Dr, Chestertown, MD 21620

    Great opportunity to own a quality built home by Coldwell Builders. Larger than average lot for the community so room to grow on this one. New home features open design with large central kitchen, dining, living area and split bedroom design. Quartz counters and stainless steel appliances in the kitchen, carpet in bedrooms and LVP everywhere else. Large yard affords many uses. Community has

    Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

    121 Fairview Dr, Chestertown, MD 21620
  • /22

    $337,000 Sold Nov 08, 2024

    • 1,338 Sq Ft
    • $252/SF
    • 16 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1975

    205 Creston Rd, Chestertown, MD 21620

    Located in a desirable community, this charming 3-bedroom, 1-bath home offers the perfect blend of comfort, convenience, and style. Situated on a generous lot, the property provides ample outdoor space for relaxation or entertaining, making it ideal for families or anyone who enjoys the outdoors.As you step inside, you'll be welcomed by a spacious living room featuring vaulted ceilings that

    Jarnell Foster Benson & Mangold, LLC

    205 Creston Rd, Chestertown, MD 21620
  • /35

    $359,000 Sold Nov 08, 2024

    • 1,500 Sq Ft
    • $239/SF
    • 82 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1984

    204 Princess Anne Dr, Chestertown, MD 21620

    Welcome home to this 3 BR 2 bath home in Kingstown Manor, situated on 1/2 acre just seconds from the Chester River. Newly refinished flooring throughout! The gorgeous, custom tiled backsplash, updated kitchen includes stainless steel appliances and is open to the dining area with built in bench seating. From the dining area you can exit the rear door onto the patio overlooking the fenced backyard

    Jamil Wright EXP Realty, LLC

    204 Princess Anne Dr, Chestertown, MD 21620
  • /37

    $675,000 Sold Oct 21, 2024

    • 2,128 Sq Ft
    • $317/SF
    • 1 Day On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1961

    319 Fairview Dr, Chestertown, MD 21620

    Live authentically. Welcome to your dream waterfront oasis! This charming home, nestled in a serene spot near historic Chestertown, offers the perfect blend of community amenities and private retreat. Boasting three bedrooms and two beautifully designed bathrooms, this property is the epitome of move-in ready.Step inside to discover a host of updates that ensure modern convenience without

    Michelle Schwab Krauss Real Property Brokerage

    319 Fairview Dr, Chestertown, MD 21620
  • /26

    $398,000 Sold Sep 27, 2024

    • 1,776 Sq Ft
    • $224/SF
    • 45 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2001

    209 Princess Anne Dr, Chestertown, MD 21620

    Welcome to 209 Princess Anne Drive, a delightful 3-bedroom, 2-bathroom home nestled on a double lot in the heart of Chestertown, Maryland. As you step into the grand foyer, you'll immediately appreciate the spaciousness and elegance this home offers.This meticulously maintained residence boasts three comfortable bedrooms that provide ample space for relaxation and privacy. The property

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    209 Princess Anne Dr, Chestertown, MD 21620
  • /23

    $230,000 Sold Sep 25, 2024

    • 1,848 Sq Ft
    • $124/SF
    • 2 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1987

    312 Princess Anne Dr, Chestertown, MD 21620

    Unlock the full potential of this charming colonial. This 4-bedroom, 2.5-bath home spans over 1,800 square feet and offers an exciting opportunity for visionaries, investors, and those with a passion for restoration. Positioned on a half-acre lot, backed by protected wetlands, offers unparalleled privacy and a serene backdrop. The primary suite offers an ensuite with stand-up shower, walk-in

    Joelle Dolch Cross Street Realtors LLC

    312 Princess Anne Dr, Chestertown, MD 21620
  • /45

    $440,000 Sold Sep 16, 2024

    • 2,128 Sq Ft
    • $207/SF
    • 2 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1988

    105 Coleman Dr, Chestertown, MD 21620

    KINGS COURT! This Colonial, sited on an acre of land, is move-in ready and boasts so many wonderful features! Here are just some that are sure to pique your interest! Freshly painted; gleaming floors; stainless steel appliances; lots of counter and cabinet space; breakfast room; separate pantry space; family room with large picture window; fireplace with stainless steel liner; newer LG washer and

    Jenn Klarman Long & Foster Real Estate, Inc.

    105 Coleman Dr, 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
  • /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
  • /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
  • /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
  • /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

Frequently Asked Questions

What is the average time to sell a house in Kingstown, MD?
The houses for sale in Kingstown, MD spend an average of 60 days on the market.
What is the number of active homes for sale in Kingstown, MD?
There are 6 active homes for sale in Kingstown, MD.

Home Trends in Kingstown, MD

Housing Trends

Median Sale Price
$520,000
Median Single Family Sale Price
$460,000
Median 1 Bedroom Sale Price
$710,000
Average Price Per Sq Ft
$291
Number of Homes for Sale
6
Last 12 months Home Sales
38
Months of Supply
1.90
Median List Price
$497,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-17%
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