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Homes for Sale near Chestertown Christian Academy

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  • 116 Harlan Loop, Chestertown, MD 21620
    116 Harlan Loop, Chestertown, MD 21620
    116 Harlan Loop, Chestertown, MD 21620
    /21

    $529,000

    • 5 Beds
    • 3.5 Baths
    • 4,067 Sq Ft

    116 Harlan Loop, Chestertown, MD 21620

    Welcome to Coventry Farms in Chestertown — where comfort, elegance, and space come together in this stunning colonial-style home!Built in 2009 and meticulously maintained, this spacious property offers over 4,000 square feet of finished living space across three levels — including a fully finished basement with a full bath, perfect for entertaining, a guest suite, or a home office

    Agent Photo

    Floretta Davis

    Samson Properties

    (410) 406-6980

    116 Harlan Loop, Chestertown, MD 21620
  • 247 Blakefield Dr, Chestertown, MD 21620
    247 Blakefield Dr, Chestertown, MD 21620
    247 Blakefield Dr, Chestertown, MD 21620
    /17

    $425,000

    • 3 Beds
    • 3 Baths
    • 2,572 Sq Ft

    247 Blakefield Dr, Chestertown, MD 21620

    Unlock the door to your future with an exclusive offer: Qualify for an exceptional 5.05% financing rate and $2,300 per month payment for one year. $7,000 lender-specific grant available on this property OR $21,250 in down payment assistance meaning no down payment is required. ARM financing also available at 5.25% rate for 5 years. Purchase this home and receive a FREE, 1-year home warranty plus

    Agent Photo

    Vinny Steo

    Your Home Sold Guaranteed Realty

    (443) 706-8420

    247 Blakefield Dr, Chestertown, MD 21620
  • 117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    /28

    $399,000

    • 2 Beds
    • 1 Bath
    • 787 Sq Ft

    117 N Water St Unit 2A, Chestertown, MD 21620

    A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. This unit offers a 2 Bed 1 bath has a brand new kitchen, with island and upgraded bathroom along with up and down river views. Enjoy all the amenities of living waterfront--Community

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 824-5609

    117 N Water St Unit 2A, Chestertown, MD 21620
  • 206 Cannon St, Chestertown, MD 21620
    206 Cannon St, Chestertown, MD 21620
    206 Cannon St, Chestertown, MD 21620
    /9

    $1,150,000

    • Land
    • 1.56 Acres
    • $737,179 per Acre

    206 Cannon St, Chestertown, MD 21620

    Extraordinary development opportunity in downtown historic Chestertown. Large parcel of land (1.56+/- acres) zoned C-2 (half R1 and half R5 zoning) many permitted uses such as Muliple-Family dwelling, Townhouses, professional and business offices, non-profit museums, and others. Includes 1 building (Warehouse) and property fronts on three streets. Excellent location-- just a few blocks to the

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (443) 419-7633

    206 Cannon St, Chestertown, MD 21620
  • 7844 Chester Ct, Chestertown, MD 21620
    7844 Chester Ct, Chestertown, MD 21620
    7844 Chester Ct, Chestertown, MD 21620
    /51

    $770,000

    • 4 Beds
    • 2.5 Baths
    • 3,248 Sq Ft

    7844 Chester Ct, Chestertown, MD 21620

    Beautifully Updated Home in a Serene Setting!Welcome to this stunning home filled with thoughtful improvements and timeless charm. The spacious Florida room overlooks a private, beautifully landscaped backyard — your own personal oasis. This room offers unlimited views of the back yard, which was designed in collaboration with a professional landscaper, this garden is a delight in every

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 648-9684

    7844 Chester Ct, Chestertown, MD 21620
  • 222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    222 Dutchess Rd, Chestertown, MD 21620
    /24

    $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

    (410) 927-1169

    222 Dutchess Rd, Chestertown, MD 21620
  • 107 Malone Ave, Chestertown, MD 21620
    107 Malone Ave, Chestertown, MD 21620
    107 Malone Ave, Chestertown, MD 21620
    /27

    $290,000

    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft

    107 Malone Ave, Chestertown, MD 21620

    Welcome to 107 Malone Ave. in the friendly community of Foxley Manor....A Great place to call "HOME"! This lovely 3 Bedroom, 1 Bath home is ready for you to make new memories, grow your family or downsize while enjoying single level living. Hardwood Floors throughout the living room and bedrooms have recently all been refinished. Through the front door is the well-lit family room with a large

    Agent Photo

    Barbara McPhail

    Douglas Realty LLC

    (410) 705-2953

    107 Malone Ave, Chestertown, MD 21620
  • 134 Char Nor Manor Blvd, Chestertown, MD 21620
    134 Char Nor Manor Blvd, Chestertown, MD 21620
    134 Char Nor Manor Blvd, Chestertown, MD 21620
    /42

    $285,000

    • 3 Beds
    • 1 Bath
    • 1,128 Sq Ft

    134 Char Nor Manor Blvd, Chestertown, MD 21620

    Chester River Charm: Your Gateway toEastern Shore LivingCompletely Renovated Cottage with River Views & Endless PossibilitiesDiscover the perfect blend of modern comfort and Eastern Shore tranquility at this beautifullytransformed 3-bedroom, 1-bath cottage just minutes from historic Chestertown and the pristineChester River. Whether you're seeking a weekend escape, investment

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (667) 282-1137

    134 Char Nor Manor Blvd, Chestertown, MD 21620
  • 117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    /28

    $725,000

    • 3 Beds
    • 3 Baths

    117 N Water St Unit 1A, Chestertown, MD 21620

    Completely remodeled, this three-bedroom waterfront home boasts a charming front porch and enormous back porch - your private space overlooking the river - along with an enclosed sunroom featuring gorgeous river views through walls of windows. Enjoy abundant outdoor areas and stunning water views from nearly every room. The dock features 3+ feel MLW, with slips available for purchase. This

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 589-6299

    117 N Water St Unit 1A, Chestertown, MD 21620
  • Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    /20

    $185,000

    • Land
    • 1.95 Acres
    • $94,872 per Acre

    Lot 9 Prestwick Dr, Chestertown, MD 21620

    Lot 9 overlooks the 5th hole tee box and the picturesque par 3 water hole # 4. Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 806-9518

    Lot 9 Prestwick Dr, Chestertown, MD 21620
  • 0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
    /27

    $1,800,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,540 Sq Ft

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620

    **Price increase due to the home’s expanded footprint—over 1,200 additional square feet!**Welcome to this beautifully designed 3,540 sq. ft. home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The standard floor plan includes 4 bedrooms and 3.5 baths, with the option to expand to 5 bedrooms and 4.5 baths by adding a first-floor guest

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 249-2840

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
  • 228 S Water St, Chestertown, MD 21620
    228 S Water St, Chestertown, MD 21620
    228 S Water St, Chestertown, MD 21620
    /32

    $878,000 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,310 Sq Ft

    228 S Water St, Chestertown, MD 21620

    Newly constructed three-bedroom townhome with all the desired attributes. Fantastic water views from the living level and bedrooms! Spacious open living space with warm hardwood floors and 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. On the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 647-9404

    228 S Water St, Chestertown, MD 21620
  • 7989 Quaker Neck Rd, Chestertown, MD 21620
    7989 Quaker Neck Rd, Chestertown, MD 21620
    7989 Quaker Neck Rd, Chestertown, MD 21620
    /90

    $2,750,000

    • 5 Beds
    • 4.5 Baths
    • 4,305 Sq Ft

    7989 Quaker Neck Rd, Chestertown, MD 21620

    Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre wallpaper,

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    7989 Quaker Neck Rd, Chestertown, MD 21620
  • 423 Calvert St, Chestertown, MD 21620
    423 Calvert St, Chestertown, MD 21620
    423 Calvert St, Chestertown, MD 21620
    /20

    $165,000

    • 3 Beds
    • 1.5 Baths
    • 1,136 Sq Ft

    423 Calvert St, Chestertown, MD 21620

    READY TO FINISH!!! LVP Flooring installed on 10/04/2025 on the main and upper levels. Materials, fixtures, applicances cabinetry, washer/dryer and new toilet on site and ready to install. Discover the potential of 423 Calvert Street — a two-story, 1,136 sq. ft. townhouse built in 1992 and set on a 2,006 sq. ft. lot. This 3-bedroom, 1.5-bath home has already undergone major updates in 2025,

    Barbara McCaffrey Redfin Corp

    423 Calvert St, Chestertown, MD 21620
  • 109 S College Ave, Chestertown, MD 21620
    109 S College Ave, Chestertown, MD 21620
    109 S College Ave, Chestertown, MD 21620
    /22

    $449,900

    • 3 Beds
    • 2.5 Baths
    • 1,216 Sq Ft

    109 S College Ave, Chestertown, MD 21620

    Charming Move-In Ready Colonial in the Heart of TownThis beautifully updated Colonial blends timeless character with modern comfort. Ideally located within walking distance of local restaurants, shops, and the scenic waterfront, it offers the perfect combination of charm and convenience.The exterior showcases classic Colonial appeal with vibrant shutters, fresh paint, new roof,

    Jeff Guthrie Cross Street Realtors LLC

    109 S College Ave, Chestertown, MD 21620
  • 206 S Water St, Chestertown, MD 21620
    206 S Water St, Chestertown, MD 21620
    206 S Water St, Chestertown, MD 21620
    /46

    $619,000

    • 4 Beds
    • 3.5 Baths
    • 2,008 Sq Ft

    206 S Water St, Chestertown, MD 21620

    Live in the heart of Chestertown’s Historic District—see your boat from your front porch!Beautifully rebuilt and expanded, this versatile home offers 3 1/2 baths and over 2,000 sq. ft. of finished living space. The rear addition features a sunroom/mudroom with separate entrance leading to a guest suite with walk-in closet and full bath.Upstairs, enjoy a second-story waterview

    Tom Williams TTR Sotheby's International Realty

    206 S Water St, Chestertown, MD 21620
  • 101 Birch Run Rd, Chestertown, MD 21620
    101 Birch Run Rd, Chestertown, MD 21620
    101 Birch Run Rd, Chestertown, MD 21620
    /38

    $525,000

    • 3 Beds
    • 2 Baths
    • 1,961 Sq Ft

    101 Birch Run Rd, Chestertown, MD 21620

    Welcome to 101 Birch Run Rd., Chestertown, MD! 3 Bedrooms | 2 Full Baths | Oversized 2-Car Garage | .42 AcresDiscover this stunning full-brick rancher located in the heart of historic Chestertown! Every inch of this 3-bedroom, 2-bath home has been completely updated with a sophisticated modern flair while maintaining an inviting, boutique-style warmth throughout.Step inside to find a

    Julie Strickler Remax Vision

    101 Birch Run Rd, Chestertown, MD 21620
  • 206 Valley Rd, Chestertown, MD 21620
    206 Valley Rd, Chestertown, MD 21620
    206 Valley Rd, Chestertown, MD 21620
    /37

    $639,900

    • 4 Beds
    • 2 Baths
    • 2,869 Sq Ft

    206 Valley Rd, Chestertown, MD 21620

    Prepare to be wowed when you walk through the front door. Gleaming hardwood floors, huge floor-to-ceiling windows, high-end kitchen and primary bath. Floor plan that flows beautifully. 4 bedrooms and 2 baths. Wood burning fire place in the living room. House is filled with natural light. Two car garage under the house with unfinished basement. Windows, roof, appliances, and HVAC have all been

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    206 Valley Rd, Chestertown, MD 21620
  • 600 Rosin Dr, Chestertown, MD 21620
    600 Rosin Dr, Chestertown, MD 21620
    600 Rosin Dr, Chestertown, MD 21620
    /35

    $415,000

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft

    600 Rosin Dr, Chestertown, MD 21620

    Charming 3-bedroom, 2-bathroom waterfront cottage nestled along the peaceful shores of Rosin Creek. Combining classic character with modern updates, the open floor plan creates a warm and inviting flow. Perfect for everyday living or entertaining. The renovated kitchen features stylish finishes and connects seamlessly to the dining and living areas. Updated flooring throughout the downstairs,

    Michele Palmer Doug Ashley Realtors, LLC

    600 Rosin Dr, Chestertown, MD 21620
  • 515 N Kent St, Chestertown, MD 21620
    515 N Kent St, Chestertown, MD 21620
    515 N Kent St, Chestertown, MD 21620
    /37

    $499,900

    • 4 Beds
    • 2 Baths
    • 2,220 Sq Ft

    515 N Kent St, Chestertown, MD 21620

    Welcome to 515 N Kent Street in the heart of Chestertown! This charming two story home features a half-circle driveway, 1-car attached garage, and inviting brick patio leading to the front door. Step inside and you’ll love the gorgeous hardwood floors throughout the main level (2022). The formal living room showcases a wood-burning fireplace with a brick mantel, creating a warm and welcoming

    Jody Baker Cross Street Realtors LLC

    515 N Kent St, Chestertown, MD 21620
  • 200 Washington Ave, Chestertown, MD 21620
    200 Washington Ave, Chestertown, MD 21620
    200 Washington Ave, Chestertown, MD 21620
    /35

    $695,000

    • 4 Beds
    • 3.5 Baths
    • 2,917 Sq Ft

    200 Washington Ave, Chestertown, MD 21620

    Only 500 steps from the center of Chestertown (5-minute walk) to this early 20th C gem of a traditional "Four Square". This prominent STAND-OUT RESIDENCE, crafted by acclaimed master builder Walter Pippin, extends a warm welcome to anyone driving (only 25mph please!) or strolling from the college campus to town, along the historically scenic Washington Avenue. The gracious flow of its' first

    Richard Keaveney Cross Street Realtors LLC

    200 Washington Ave, 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

    $410,000

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

    907 N Meadowview Dr, Chestertown, MD 21620

    JUST INSTALLED BRAND NEW CARPET! Welcome to 907 N Meadowview Drive, a beautifully maintained home in the sought-after Crestview community of Chestertown. Situated on a spacious .707-acre lot, this 3-bedroom, 2.5-bath home offers 1,842 square feet of comfortable living space.Step inside to find a bright and inviting living room anchored by a cozy pellet stove, ideal for chilly

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    907 N Meadowview Dr, Chestertown, MD 21620
  • 165 Char Nor Manor Blvd, Chestertown, MD 21620
    165 Char Nor Manor Blvd, Chestertown, MD 21620
    165 Char Nor Manor Blvd, Chestertown, MD 21620
    /67

    $429,999

    • 4 Beds
    • 2.5 Baths
    • 2,258 Sq Ft

    165 Char Nor Manor Blvd, Chestertown, MD 21620

    Chester River Views from Every Angle!Welcome to this stunning Colonial located on the Queen Anne’s County side of Chestertown, offering unmatched views of the Chester River and serene waterfront living.This spacious home features 4 large bedrooms, 2.5 bathrooms, and gorgeous hardwood floors throughout. Enjoy cozy nights by the wood-burning fireplace in the living room and enjoy

    Crystal Smith RE/MAX Executive

    165 Char Nor Manor Blvd, Chestertown, MD 21620
  • 201 Birch Run Rd, Chestertown, MD 21620
    201 Birch Run Rd, Chestertown, MD 21620
    201 Birch Run Rd, Chestertown, MD 21620
    /23

    $470,000

    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft

    201 Birch Run Rd, Chestertown, MD 21620

    This Mid Century Modern is located in Mile Tree Village, one of Chestertown's most coveted neighborhoods. One floor living makes things a breeze with this open and easy floor plan. Serious structural updates have been performed on the home, the crawl space has been encapsulated, and the kitchen and bathrooms have been remodeled. The home was also recently had the entire exterior painted and much

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    201 Birch Run Rd, Chestertown, MD 21620
  • 116 Pine Chip Rd, Chestertown, MD 21620
    116 Pine Chip Rd, Chestertown, MD 21620
    116 Pine Chip Rd, Chestertown, MD 21620
    /35

    $475,000

    • 3 Beds
    • 1.5 Baths
    • 2,767 Sq Ft

    116 Pine Chip Rd, Chestertown, MD 21620

    Don’t let the outside fool you—this beautifully renovated 3-bedroom, 1.5-bathroom home offers three levels of living space, with over 2,200 sq. ft. above ground and an additional 550 sq. ft. below ground! Every inch of this home has been thoughtfully updated to blend modern comfort with timeless charm.Step inside to discover a stunning custom kitchen, a true chef’s dream featuring a gas

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    116 Pine Chip Rd, Chestertown, MD 21620
  • 25070 Lambs Meadow Rd, Worton, MD 21678
    25070 Lambs Meadow Rd, Worton, MD 21678
    25070 Lambs Meadow Rd, Worton, MD 21678
    /55

    $405,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,264 Sq Ft

    25070 Lambs Meadow Rd, Worton, MD 21678

    Looking for NEW construction and the convenience of one-story living? Look No Further! At the end of aprivate driveway is this elegantly designed 3 BR 2 bath Country Craftsman nestled on a 0.25 acre lot. Amulti pitched roofline tops this beautiful home which displays craftsmanship and attention to detail. Thisoasis which has a keyless entry two-car attached garage is adorned with

    Antoinette Brooks EXP Realty, LLC

    25070 Lambs Meadow Rd, Worton, MD 21678
  • 411 Greenwood Ave, Chestertown, MD 21620
    411 Greenwood Ave, Chestertown, MD 21620
    411 Greenwood Ave, Chestertown, MD 21620
    /6

    $419,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 2.5 Baths
    • 1,676 Sq Ft

    411 Greenwood Ave, Chestertown, MD 21620

    Interior photos coming but for now refer to the photos on the previous listing

    Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    411 Greenwood Ave, Chestertown, MD 21620
  • 492 Pear Tree Point Rd, Chestertown, MD 21620
    492 Pear Tree Point Rd, Chestertown, MD 21620
    492 Pear Tree Point Rd, Chestertown, MD 21620
    /73

    $920,000

    • 3 Beds
    • 2 Baths
    • 2,632 Sq Ft

    492 Pear Tree Point Rd, Chestertown, MD 21620

    Welcome to 492 Pear Tree Point Road: an exceptional Chester River waterfront home with unique upriver views. Spacious rooms, gorgeous cherry hardwoods, a back deck to die for, private setting, and with space to add; this home has it all! Good water depth for a dock and center console. Nearly an acre of elevated land - out of the flood zone - that backs to picturesque horse pasture. The main

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    492 Pear Tree Point Rd, Chestertown, MD 21620
  • 11047 Bottom Rd, Worton, MD 21678
    11047 Bottom Rd, Worton, MD 21678
    11047 Bottom Rd, Worton, MD 21678
    /26

    $325,000

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    11047 Bottom Rd, Worton, MD 21678

    Check out this Like New , MOVE IN READY Rancher with an Amazing view ! This beautiful 3-bedroom, 2-bathroom residence offers quality craftsmanship and tasteful upgrades throughout. From the granite countertops to the designer bathroom vanities and recessed lighting, every detail has been carefully selected for both style and function.The kitchen is a standout feature—complete

    Jeff Guthrie Cross Street Realtors LLC

    11047 Bottom Rd, Worton, MD 21678
  • 221 Old Bridge Rd, Chestertown, MD 21620
    221 Old Bridge Rd, Chestertown, MD 21620
    221 Old Bridge Rd, Chestertown, MD 21620
    /29

    $369,900

    • 3 Beds
    • 2 Baths
    • 1,851 Sq Ft

    221 Old Bridge Rd, Chestertown, MD 21620

    Charming American Foursquare on a half-acre corner lot, just one block from the Chester River on the Queen Anne's County side of Historic Chestertown. The home features a welcoming front porch, 3 bedrooms, 2 full baths, an office on the main level, hardwood floors, and many original details. Recent updates include a new upstairs bathroom, new electric panel, and a 2-year-old roof. The walk-up

    Courtney Chipouras TTR Sotheby's International Realty

    221 Old Bridge Rd, Chestertown, MD 21620
  • 11150 Old Worton Rd, Worton, MD 21678
    11150 Old Worton Rd, Worton, MD 21678
    11150 Old Worton Rd, Worton, MD 21678
    /3

    $189,000

    • Land
    • 1 Acre
    • $189,000 per Acre

    11150 Old Worton Rd, Worton, MD 21678

    Former site of the popular Clark's Store - come with vision, roll up your sleeves and get to work on this 1 acre lot zoned Village which allows for mixed uses including residential and commercial. The property includes 3 phased electric service to the existing building as well as THREE WATER & SEWER ALLOCATIONS. Rebuild the existing block walls or start over from scratch there are endless

    John Carroll Village Real Estate Company LLC

    11150 Old Worton Rd, Worton, MD 21678
  • 7653 Broad Neck Rd, Chestertown, MD 21620
    7653 Broad Neck Rd, Chestertown, MD 21620
    7653 Broad Neck Rd, Chestertown, MD 21620
    /39

    $375,000

    • 4 Beds
    • 3 Baths
    • 1,790 Sq Ft

    7653 Broad Neck Rd, Chestertown, MD 21620

    Recently and thoroughly renovated, charming and spacious 4 bedroom 3 bathroom home located only about 6 miles from Chestertown in an idyllic country setting. Some improvements include new HVAC, electric, 3 season room , water filter and high-end, smart appliances. Terrific in-ground pool enclosed with privacy brick wall, a large patio and deck are perfect for entertaining or relaxing in the

    Brian Petzold Benson & Mangold, LLC

    7653 Broad Neck Rd, Chestertown, MD 21620
  • 517 High St, Chestertown, MD 21620
    517 High St, Chestertown, MD 21620
    517 High St, Chestertown, MD 21620
    /51

    $389,900

    • Studio
    • 1,728 Sq Ft

    517 High St, Chestertown, MD 21620

    Fantastic investment opportunity. Highly sought after downtown Historic Chestertown. This 3 unit property is ready to rent. Recently updated and renovated throughout the years, pride of ownership is apparent. The main level has a Studio with new kitchen, full bath and large living area. There is a door to the new deck and quiet back yard. Heating is a gas unit and cooling would be a window unit-

    Kristie Midash L. C. Parker Real Estate

    517 High St, Chestertown, MD 21620
  • 25135 Smithville Rd, Worton, MD 21678
    25135 Smithville Rd, Worton, MD 21678
    25135 Smithville Rd, Worton, MD 21678
    /25

    $299,000

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    25135 Smithville Rd, Worton, MD 21678

    Welcome to this beautifully updated 3 bedroom, 1 bathroom home with an oversized two car detached garage that combines modern upgrades with country charm. Step inside to find brand new LVP flooring throughout, fresh paint and abundant natural light.The new kitchen is the heart of the home, featuring quartz countertops, new stainless steel appliances and crisp white shaker cabinetry. The

    Jane Duvall RE/MAX Advantage Realty

    25135 Smithville Rd, Worton, MD 21678
  • 0 Lambs Meadow Rd Unit MDKE2005704, Worton, MD 21678
    0 Lambs Meadow Rd Unit MDKE2005704, Worton, MD 21678
    0 Lambs Meadow Rd Unit MDKE2005704, Worton, MD 21678
    /15

    $75,000

    • Land
    • 1.09 Acres
    • $68,807 per Acre

    0 Lambs Meadow Rd Unit MDKE2005704, Worton, MD 21678

    Set on just over 1 acre in the Village zoning district, this partially wooded property offers a rare mix of flexibility and possibility. This zoning permits a wide range of uses from single-family, multi-family, and/or townhouses, to short-term vacation rentals, and even certain commercial spaces like restaurants (without drive-thru capabilities), you have room to bring your vision to life. The

    Micheal Vakas EXP Realty, LLC

    0 Lambs Meadow Rd Unit MDKE2005704, Worton, MD 21678
  • 112 Silver Heel Rd, Chestertown, MD 21620
    112 Silver Heel Rd, Chestertown, MD 21620
    112 Silver Heel Rd, Chestertown, MD 21620
    /43

    $374,900

    • 5 Beds
    • 3.5 Baths
    • 2,615 Sq Ft

    112 Silver Heel Rd, Chestertown, MD 21620

    Welcome to this stunning 2023 built home — a move-in ready, three-story residence offering 5 bedrooms and 3.5 baths across 2,615 sq ft of thoughtfully designed space.The first floor features an open layout with a spacious family room, dining area, and bright, well-appointed kitchen. This level also includes a convenient first-floor laundry and a powder room. The kitchen is equipped

    Federico Busacca EXP Realty, LLC

    112 Silver Heel Rd, Chestertown, MD 21620
  • 118 Little Harbor Way Unit 201, Chestertown, MD 21620
    118 Little Harbor Way Unit 201, Chestertown, MD 21620
    118 Little Harbor Way Unit 201, Chestertown, MD 21620
    /35

    $675,000

    • 2 Beds
    • 2.5 Baths
    • 1,550 Sq Ft

    118 Little Harbor Way Unit 201, Chestertown, MD 21620

    An impeccably maintained, perfectly positioned two bedroom, two and one-half bath condo featuring one of the best vistas of Chestertown and Chester River. It is nearly impossible for the body, mind and spirit of its residents and guests not to be "in a good place" on the cloudiest or most challenging of days. River House, with only five private residences, occupies the best real estate within

    Richard Keaveney Cross Street Realtors LLC

    118 Little Harbor Way Unit 201, Chestertown, MD 21620
  • 119 Darden Rd, Chestertown, MD 21620
    119 Darden Rd, Chestertown, MD 21620
    /2

    $315,000

    • 3 Beds
    • 2 Baths
    • 1,424 Sq Ft

    119 Darden Rd, Chestertown, MD 21620

    Welcome to 119 Darden Road, a lovely ranch-style home nestled in Chestertown, MD. This charming residence offers 3 cozy bedrooms and 2 bathrooms across 1,424 square feet of living space, perfect for comfortable living. The eat-in kitchen, complete with a handy stove, sets the stage for delightful meals and gatherings. Enjoy the warm ambiance of a fireplace in the spacious living room, enhanced by

    Solomon Zaldivar Compass

    119 Darden Rd, Chestertown, MD 21620
  • 103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    /69

    $559,000 Open Sun 11AM - 2PM

    • 2 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    103 Landing Ln, Chestertown, MD 21620

    Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the rear den or office which could be

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    103 Landing Ln, Chestertown, MD 21620
  • 10740 Worton Rd, Worton, MD 21678
    10740 Worton Rd, Worton, MD 21678
    10740 Worton Rd, Worton, MD 21678
    /52

    $375,000

    • 3 Beds
    • 3 Baths
    • 2,988 Sq Ft

    10740 Worton Rd, Worton, MD 21678

    This home was formerly the old Worton Elementary schoolhouse and still retains some of the original features, such as tin ceilings in the living room. The main level has a spacious living room with wood floors, huge kitchen with wood stove, a main level bedroom with a sitting room and full bath with a walk-in shower, and additional hall bath with laundry, several additional rooms and 2 screened

    Doug Ashley Doug Ashley Realtors, LLC

    10740 Worton Rd, Worton, MD 21678

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