188

Recently Sold Chestertown, MD Homes

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  • 5 Rolling Rd, Chestertown, MD 21620
    5 Rolling Rd, Chestertown, MD 21620
    5 Rolling Rd, 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
  • 142 Church Meadow Ct, Chestertown, MD 21620
    142 Church Meadow Ct, Chestertown, MD 21620
    142 Church Meadow Ct, Chestertown, MD 21620
    /27

    $405,000 Sold Nov 22, 2024

    • 1,426 Sq Ft
    • $284/SF
    • 39 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2014

    142 Church Meadow Ct, Chestertown, MD 21620

    Conveniently located between Church Hill and Chestertown this home sits on a quiet cul de sac with 1.25 acre lot backing to farm fields. Fenced rear yard is great for 2 or 4 legged family members and provides ample room to play, garden, or just relax. Inside features over 1400 SQFT of finished space with 3 bedrooms, 2.5 bathrooms and great lower level family room with walk out to rear yard

    Thomas Boeshore Berkshire Hathaway Homeservice Homesale Realty

    142 Church Meadow Ct, Chestertown, MD 21620
  • 209 Birch Run Rd, Chestertown, MD 21620
    209 Birch Run Rd, Chestertown, MD 21620
    209 Birch Run 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
  • 503 N Kent St, Chestertown, MD 21620
    503 N Kent St, Chestertown, MD 21620
    503 N Kent St, 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
  • 201 Princess Anne Dr, Chestertown, MD 21620
    201 Princess Anne Dr, Chestertown, MD 21620
    201 Princess Anne Dr, 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
  • 217 Birch Run Rd, Chestertown, MD 21620
    217 Birch Run Rd, Chestertown, MD 21620
    217 Birch Run Rd, 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
  • 307 Washington Ave, Chestertown, MD 21620
    307 Washington Ave, Chestertown, MD 21620
    307 Washington Ave, 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
  • 22956 Fairgale Farm Ln, Chestertown, MD 21620
    22956 Fairgale Farm Ln, Chestertown, MD 21620
    22956 Fairgale Farm Ln, Chestertown, MD 21620
    /82

    $1,200,000 Sold Nov 13, 2024

    • 6,459 Sq Ft
    • $186/SF
    • 119 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 2000

    22956 Fairgale Farm Ln, Chestertown, MD 21620

    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, creating a sense of grandeur and privacy. Nestled on the shores of an oversized pond, this exquisite home offers not only stunning views but also

    Retha Arrabal Doug Ashley Realtors, LLC

    22956 Fairgale Farm Ln, Chestertown, MD 21620
  • 121 Fairview Dr, Chestertown, MD 21620
    121 Fairview Dr, Chestertown, MD 21620
    121 Fairview 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
  • 205 Creston Rd, Chestertown, MD 21620
    205 Creston Rd, Chestertown, MD 21620
    205 Creston Rd, 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
  • 126 Hilltop Dr, Chestertown, MD 21620
    126 Hilltop Dr, Chestertown, MD 21620
    126 Hilltop Dr, Chestertown, MD 21620
    /57

    $465,000 Sold Nov 08, 2024

    • 2,733 Sq Ft
    • $170/SF
    • 41 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2001

    126 Hilltop Dr, Chestertown, MD 21620

    Discover your dream home perched on a tranquil hill in Chestertown, Maryland. This beautiful 3-bedroom, 2.5-bathroom residence features lush landscaping and a welcoming front porch, ideal for enjoying scenic views. Inside, the open floor plan is filled with natural light, showcasing a spacious living room with a cozy fireplace and a gourmet kitchen that’s perfect for entertaining. The master

    Chardae Eduruke Taylor Properties

    126 Hilltop Dr, Chestertown, MD 21620
  • 204 Princess Anne Dr, Chestertown, MD 21620
    204 Princess Anne Dr, Chestertown, MD 21620
    204 Princess Anne Dr, 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
  • 129 Char Nor Manor Blvd, Chestertown, MD 21620
    129 Char Nor Manor Blvd, Chestertown, MD 21620
    129 Char Nor Manor Blvd, Chestertown, MD 21620
    /43

    $411,500 Sold Nov 07, 2024

    • 810 Sq Ft
    • $508/SF
    • 5 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1961

    129 Char Nor Manor Blvd, Chestertown, MD 21620

    Enjoy the serenity of waterfront living in this delightful 2-bedroom, 1-bath ranch home nestled along the scenic Chester River. This cozy retreat offers stunning, uninterrupted views of the water from nearly every room. Imagine spending your mornings sipping coffee on the private dock or screened porch, or relaxing by the warmth of the wood-burning fireplace on cool evenings.The open floor

    Melanie Musser Iron Valley Real Estate of Central PA

    129 Char Nor Manor Blvd, Chestertown, MD 21620
  • 813 S Meadowview Dr, Chestertown, MD 21620
    813 S Meadowview Dr, Chestertown, MD 21620
    813 S Meadowview Dr, 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
  • 112 Snyder Ln, Chestertown, MD 21620
    112 Snyder Ln, Chestertown, MD 21620
    112 Snyder Ln, Chestertown, MD 21620
    /16

    $215,000 Sold Nov 04, 2024

    • 966 Sq Ft
    • $223/SF
    • 22 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1988

    112 Snyder Ln, Chestertown, MD 21620

    ***Property back on market due to Buyer Default. ***This move-in ready home has been tastefully updated and is conveniently located close to downtown Chestertown while maintaining the benefits of Queen Anne's County. The primary suite has a spacious en suite bathroom and laundry area. An open floor plan provides plenty of living space and leads to another full bathroom and bedroom. An

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    112 Snyder Ln, Chestertown, MD 21620
  • 8489 Broad Neck Rd, Chestertown, MD 21620
    8489 Broad Neck Rd, Chestertown, MD 21620
    8489 Broad Neck Rd, Chestertown, MD 21620
    /25

    $299,900 Sold Nov 01, 2024

    • 1,464 Sq Ft
    • $205/SF
    • 10 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1960

    8489 Broad Neck Rd, Chestertown, MD 21620

    Welcome to this newly updated 3-bedroom, 2-bathroom rancher, conveniently located on Broad Neck Road, just minutes from historic Chestertown! This home offers some nice upgrades such as a brand-new roof, gutters, and HVAC system, ensuring year-round comfort and a full unfinished basement with heating and air conditioning—perfect for extra storage or future expansion. The interior has been

    Jody Baker Cross Street Realtors LLC

    8489 Broad Neck Rd, Chestertown, MD 21620
  • 208 N Queen St, Chestertown, MD 21620
    208 N Queen St, Chestertown, MD 21620
    208 N Queen St, Chestertown, MD 21620
    /37

    $600,000 Sold Nov 01, 2024

    • 3,240 Sq Ft
    • $185/SF
    • 6 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1900

    208 N Queen St, Chestertown, MD 21620

    Welcome to this charming Colonial four square home, nestled on the north end of Queen Street in Chestertown's historic district, just two blocks from the river. Step inside to find a beautifully remodeled kitchen, updated living room, dining room, den which doubles as a library or family room, and a sunlit porch, all on the main level. With high ceilings, intricate detailing, and polished

    Jody Baker Cross Street Realtors LLC

    208 N Queen St, Chestertown, MD 21620
  • 24105 Chestertown Rd, Chestertown, MD 21620
    24105 Chestertown Rd, Chestertown, MD 21620
    24105 Chestertown Rd, Chestertown, MD 21620
    /17

    $275,000 Sold Oct 29, 2024

    • 1,317 Sq Ft
    • $209/SF
    • 9 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1970

    24105 Chestertown Rd, Chestertown, MD 21620

    Custom quality-built 1970 brick rancher on 0.46 acre lot just outside Chestertown. House features original hardwood floors, stained woodwork, trim moldings and hand built wood kitchen cabinetry. The living room has large bay window and brick wood burning fireplace. Full unfinished basement offers lots of extra storage space with room to expand. Attached carport with storage closets and

    Yvonne Andres Keller Williams Select Realtors of Annapolis

    24105 Chestertown Rd, Chestertown, MD 21620
  • 305 Hickory Ln, Chestertown, MD 21620
    305 Hickory Ln, Chestertown, MD 21620
    305 Hickory Ln, Chestertown, MD 21620
    /6

    $615,000 Sold Oct 25, 2024

    • 2,627 Sq Ft
    • $234/SF
    • 2 Beds
    • 1.5 Baths
    • Built 1998

    305 Hickory Ln, Chestertown, MD 21620

    Perfect Rabbit Creek and Chester River Get-A-Way. Ideal for an avid sportsman, outdoorsman or nature lover, offering you extensive frontage on Rabbit Creek leading out into the Chester River situated on 20 private acres. Offering a serene setting with a good mix of marshland, woods, uplands and a private pond. Bring your canoe/kayak/ john boat/ fishing pole and deer stand. These properties

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    305 Hickory Ln, Chestertown, MD 21620
  • 10674 Kasota Rd, Chestertown, MD 21620
    10674 Kasota Rd, Chestertown, MD 21620
    10674 Kasota Rd, Chestertown, MD 21620
    /9

    $135,000 Sold Oct 25, 2024

    • 1,350 Sq Ft
    • $100/SF
    • 24 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1977

    10674 Kasota Rd, Chestertown, MD 21620

    Very affordable with a nice .59 acre lot. A great Re-Hab opportunity. Nicely located Rancher in Chesapeake Landing. Voluntary HOA membership allows access to Worton Creek. Property Backs up to Community Recreational Area with a pond. This is an opportunity to design your new home.

    Richard King Doug Ashley Realtors, LLC

    10674 Kasota Rd, Chestertown, MD 21620
  • 100 Foxview Ct, Chestertown, MD 21620
    100 Foxview Ct, Chestertown, MD 21620
    100 Foxview Ct, Chestertown, MD 21620
    /41

    $435,000 Sold Oct 24, 2024

    • 3,000 Sq Ft
    • $145/SF
    • 7 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 1999

    100 Foxview Ct, Chestertown, MD 21620

    Nestled at the end of a serene cul-de-sac in the desirable Crestview neighborhood, this expansive 3,000-square-foot home resides on a generous 0.63-acre lot, boasting a delightful fusion of comfort and sophistication. Adorned with meticulously landscaped grounds, the outdoor space features a charming fish pond complemented by water features, a convenient shed, an expansive patio, and a deck

    Sarah Ulrick Rock Hall Properties Real Estate

    100 Foxview Ct, Chestertown, MD 21620
  • 319 Fairview Dr, Chestertown, MD 21620
    319 Fairview Dr, Chestertown, MD 21620
    319 Fairview 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
  • 235 Island Lark Way, Chestertown, MD 21620
    235 Island Lark Way, Chestertown, MD 21620
    235 Island Lark Way, Chestertown, MD 21620
    /22

    $287,000 Sold Oct 18, 2024

    • 1,420 Sq Ft
    • $202/SF
    • 8 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2023

    235 Island Lark Way, Chestertown, MD 21620

    Village at Chestertown end-unit two-story townhome with 3 bedrooms and 2.5 bathrooms. The spacious first floor is open-concept consisting of a kitchen, living, and dining area. The thoughtfully designed kitchen comes with stylish gray cabinets, stainless steel appliances, a storage closet and a peninsula island that seats three. The first floor also offers a spacious living area and powder room.

    Derek Eisenberg Continental Real Estate Group

    235 Island Lark Way, Chestertown, MD 21620
  • 231 Blakefield Dr, Chestertown, MD 21620
    231 Blakefield Dr, Chestertown, MD 21620
    231 Blakefield Dr, Chestertown, MD 21620
    /4

    $422,000 Sold Oct 18, 2024

    • 1,600 Sq Ft
    • $264/SF
    • 0 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2024

    231 Blakefield Dr, Chestertown, MD 21620

    3 BEDROOM 2 BATH RANCHER. OPEN FLOOR PLAN. NEW CONSTRUCTION TO START 2024. 1600SF ON 1 ACRE LOT

    Chris Haddaway Chesapeake Real Estate Associates, LLC

    231 Blakefield Dr, Chestertown, MD 21620
  • 9020 Cumberland St, Chestertown, MD 21620
    9020 Cumberland St, Chestertown, MD 21620
    9020 Cumberland St, Chestertown, MD 21620
    /48

    $260,000 Sold Oct 18, 2024

    • 1,150 Sq Ft
    • $226/SF
    • 263 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1949

    9020 Cumberland St, Chestertown, MD 21620

    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 additional "sleeping loft". Tolchester Beach is located on the Chesapeake Bay and has a beautiful beach and boat ramp. Walking distance to The Shanty

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    9020 Cumberland St, Chestertown, MD 21620
  • 7755 Waterview Ln, Chestertown, MD 21620
    7755 Waterview Ln, Chestertown, MD 21620
    7755 Waterview Ln, Chestertown, MD 21620
    /65

    $950,000 Sold Oct 17, 2024

    • 4,730 Sq Ft
    • $201/SF
    • 110 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2011

    7755 Waterview Ln, Chestertown, MD 21620

    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 landscaping around the circular driveway is lovely; the garage is set on an angle as to be unobtrusive from the road and the house entrance. Inside, all

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    7755 Waterview Ln, Chestertown, MD 21620
  • 201 N Water St, Chestertown, MD 21620
    201 N Water St, Chestertown, MD 21620
    201 N Water St, Chestertown, MD 21620
    /76

    $1,362,500 Sold Oct 16, 2024

    • 5,195 Sq Ft
    • $262/SF
    • 457 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 1760

    201 N Water St, Chestertown, MD 21620

    SMITH-RINGGOLD HOUSE. ca. 1750 OWNER IS MEETING THE MARKET for this rare property WITH PRICE NOW AT $1,6500,000. 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 , the Smith-Ringgold house has been tastefully modified

    Nancy McGuire Maryland Heritage Properties

    201 N Water St, Chestertown, MD 21620
  • 125 High St, Chestertown, MD 21620
    125 High St, Chestertown, MD 21620
    125 High St, Chestertown, MD 21620
    /22

    $565,000 Sold Oct 07, 2024

    • 1,146 Sq Ft
    • $493/SF
    • 42 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1870

    125 High St, Chestertown, MD 21620

    This exquisitely renovated 1800s 2 Bedroom home showcases the timeless elegance of its original architecture. Every detail has been restored to its former glory with preserving its charm and character of its historic roots while incorporating modern updates for a truly exception living experience.Located in the heart of Chestertown with very easy walk to shops, restaurants, parks and just

    John Burke Gunther-McClary Real Estate

    125 High St, Chestertown, MD 21620
  • 21320 Persimmon Dr, Chestertown, MD 21620
    21320 Persimmon Dr, Chestertown, MD 21620
    21320 Persimmon Dr, Chestertown, MD 21620
    /27

    $165,000 Sold Oct 04, 2024

    • 1,232 Sq Ft
    • $134/SF
    • 24 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1955

    21320 Persimmon Dr, Chestertown, MD 21620

    Fresh new look to this townhome includes fresh paint, new carpet and new HVAC system. Looking for an affordable option to paying rent? This two bedroom townhouse is just the answer. Close to the Bay and all Tolchester offers from it's marina, Shanty beach bar and the best spot for an incredible sunset. Tolchester Village offers the perfect location for those looking for a summer retreat or full

    Amy Larrauri Chesapeake Real Estate Associates, LLC

    21320 Persimmon Dr, Chestertown, MD 21620
  • 23118 Raleigh Rd, Chestertown, MD 21620
    23118 Raleigh Rd, Chestertown, MD 21620
    23118 Raleigh Rd, Chestertown, MD 21620
    /36

    $380,000 Sold Oct 03, 2024

    • 1,625 Sq Ft
    • $234/SF
    • 9 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1970

    23118 Raleigh Rd, Chestertown, MD 21620

    Welcome to this beautifully updated rancher, offering a perfect blend of classic charm and modern amenities. This home boasts an oversized detached 2-car garage and an inviting in-ground saltwater pool. Inside, you'll find two fully remodeled bathrooms, stunning hardwood floors, and a back screened-in porch where you can relax and enjoy serene country views. Recent upgrades include a newer HVAC

    Kaitlyn Collins Benson & Mangold, LLC

    23118 Raleigh Rd, Chestertown, MD 21620
  • 7694 Waterview Ln, Chestertown, MD 21620
    7694 Waterview Ln, Chestertown, MD 21620
    7694 Waterview Ln, Chestertown, MD 21620
    /13

    $749,000 Sold Oct 01, 2024

    • 3,322 Sq Ft
    • $225/SF
    • 3 Beds
    • 2 Baths
    • Built 1966

    7694 Waterview Ln, Chestertown, MD 21620

    Prepare to be wowed! Stunning house in Country Club Estates. Less than 2 miles from Chestertown and close to the Chester River. One floor living. Large rear and side yards. Easy flow floor plan with spacious rooms. Plenty of storage space. Nothing needed, just bring your suitcase!

    Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    7694 Waterview Ln, Chestertown, MD 21620
  • 9769 Augustine Herman Hwy, Chestertown, MD 21620
    9769 Augustine Herman Hwy, Chestertown, MD 21620
    9769 Augustine Herman Hwy, Chestertown, MD 21620
    /46

    $279,000 Sold Sep 27, 2024

    • 1,456 Sq Ft
    • $192/SF
    • 5 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1961

    9769 Augustine Herman Hwy, Chestertown, MD 21620

    Panoramic farmland views and a peaceful rural setting invite you to enjoy all that this traditional brick home has to offer. Original oak hardwood floors add classic charm to the spacious traditional floor plan, perfect for both entertaining and everyday living. A large rear-facing garage compliments the home's livability and enhances it's curb appeal. Situated on 1.38 acres, the surrounding yard

    Rosella Hunter Remax Vision

    9769 Augustine Herman Hwy, Chestertown, MD 21620
  • 209 Princess Anne Dr, Chestertown, MD 21620
    209 Princess Anne Dr, Chestertown, MD 21620
    209 Princess Anne 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
  • 631 High St, Chestertown, MD 21620
    631 High St, Chestertown, MD 21620
    631 High St, Chestertown, MD 21620
    /9

    $250,000 Sold Sep 27, 2024

    • 1,234 Sq Ft
    • $203/SF
    • 36 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1917

    631 High St, Chestertown, MD 21620

    Investor Alert! A rare opportunity to own a piece of History in down town Chestertown! This home has been a very lucrative rental for the past 10 years which you can easily add to your portfolio or rennovate and bring it back to its glory! One of the few homes on High Street to come with off street parking (up to 4 spaces) accessed by alley way in back. Partially fenced in back yard with privacy

    Michele Palmer Doug Ashley Realtors, LLC

    631 High St, Chestertown, MD 21620
  • 213 Devon Dr, Chestertown, MD 21620
    213 Devon Dr, Chestertown, MD 21620
    213 Devon Dr, Chestertown, MD 21620
    /24

    $350,000 Sold Sep 27, 2024

    • 2,472 Sq Ft
    • $142/SF
    • 85 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2005

    213 Devon Dr, Chestertown, MD 21620

    Well maintained Cape Cod in the sought after Coventry Farms subdivision in Chestertown - 1st Floor Master Bedroom includes a spacious walk in closet and a large Full Bath with Walk in Shower – 4 bedrooms, 2.5 baths, a spacious living room, and a large kitchen makes this home irresistible – Be sure to step outside from the dining room through the sliding glass door into the large screened-in deck

    Christopher Buss Weichert Realtors - Blue Ribbon

    213 Devon Dr, Chestertown, MD 21620
  • 211 Byford Dr, Chestertown, MD 21620
    211 Byford Dr, Chestertown, MD 21620
    211 Byford Dr, Chestertown, MD 21620
    /31

    $394,000 Sold Sep 26, 2024

    • 1,616 Sq Ft
    • $244/SF
    • 8 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1965

    211 Byford Dr, Chestertown, MD 21620

    Welcome to a hidden oasis, just steps from Downtown Chestertown! This Byford Heights home has been meticulously maintained; featuring main level living, attached oversized garage, home office space, an ample screen porch, fully fenced back yard, and in-ground pool. And, untouched hardwood floors just begging to be uncovered! Open House on Saturday the 24th from 1-3p.

    Liddy Campbell TTR Sotheby's International Realty

    211 Byford Dr, Chestertown, MD 21620
  • 312 Princess Anne Dr, Chestertown, MD 21620
    312 Princess Anne Dr, Chestertown, MD 21620
    312 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
  • 10705 Tilden Ln, Chestertown, MD 21620
    10705 Tilden Ln, Chestertown, MD 21620
    10705 Tilden Ln, Chestertown, MD 21620
    /50

    $1,300,000 Sold Sep 24, 2024

    • 3,345 Sq Ft
    • $389/SF
    • 18 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1943

    10705 Tilden Ln, Chestertown, MD 21620

    Enjoy picturesque water views of Worton Creek from every room. Situated on over 2.5 acres of well maintained and landscaped property with irrigation and enjoy the water from the private pier with 5 ft. of depth and only minutes by boat to the Chesapeake Bay or relax by the water side pool. This five bedroom three bath home has an apartment above the detached 3 car garage with a full kitchen,

    Glenn Sutton TTR Sotheby's International Realty

    10705 Tilden Ln, Chestertown, MD 21620
  • 235 Burchard Sawmill Rd, Chestertown, MD 21620
    235 Burchard Sawmill Rd, Chestertown, MD 21620
    235 Burchard Sawmill Rd, Chestertown, MD 21620
    /24

    $250,000 Sold Sep 23, 2024

    • 864 Sq Ft
    • $289/SF
    • 115 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1930

    235 Burchard Sawmill Rd, Chestertown, MD 21620

    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 storage shed, and updated BAT system septic. Spacious yard for a garden and family events. Can't pass up this AFFORDABLE price point for like new

    John Carroll Village Real Estate Company LLC

    235 Burchard Sawmill Rd, Chestertown, MD 21620
  • 10572 Klamath Rd, Chestertown, MD 21620
    10572 Klamath Rd, Chestertown, MD 21620
    10572 Klamath Rd, Chestertown, MD 21620
    /27

    $269,900 Sold Sep 20, 2024

    • 1,232 Sq Ft
    • $219/SF
    • 70 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1996

    10572 Klamath Rd, Chestertown, MD 21620

    Sellers offering $10,000 credit toward cosmetic repairs or settlement!!!! Cute rancher in Chesapeake Landing. Nice front porch. Large living room with a woodstove with brick hearth and mantle. Laminate flooring throughout most of the house. 3 bedrooms and 2 full baths. Guest bathroom is a great size and also contains the washer dryer. Stainless appliances. Kitchen Island. Nice sized lot

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    10572 Klamath Rd, Chestertown, MD 21620

Showing Results 81 - 120, Page 3 of 5

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