180

Kent County MD Homes for Sale

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  • 32135 River Rd, Millington, MD 21651
    32135 River Rd, Millington, MD 21651
    32135 River Rd, Millington, MD 21651
    /33

    $490,000

    • 2 Beds
    • 2 Baths
    • 1,176 Sq Ft

    32135 River Rd, Millington, MD 21651

    Experience waterfront living on the beautiful Chester River in Millington, just 15 minutes from Middletown, DE. Situated on 0.53 acres, this charming riverfront carriage house captures breathtaking panoramic water views and offers the perfect blend of relaxation, recreation, and convenience. An expansive lighted deck creates the ideal setting for morning coffee, outdoor dining, entertaining

    Christine Catalano Coldwell Banker Realty

    32135 River Rd, Millington, MD 21651
  • 423 Cypress St, Millington, MD 21651
    423 Cypress St, Millington, MD 21651
    423 Cypress St, Millington, MD 21651
    /15

    $295,000

    • 3 Beds
    • 1 Bath
    • 952 Sq Ft

    423 Cypress St, Millington, MD 21651

    Turn-key, one-level living in the heart of charming downtown Millington! Welcome to 423 Cypress Street, a beautifully maintained and thoughtfully updated home that is truly move-in ready!! Take advantage of the seller’s option to convey the home fully furnished as they relocate out of state. This stress-free property has been lovingly cared for, and it shows in every detail. Major updates include

    Jenyne Ward Patterson-Schwartz Real Estate

    423 Cypress St, Millington, MD 21651
  • 21610 Hidden Creek Dr, Rock Hall, MD 21661
    21610 Hidden Creek Dr, Rock Hall, MD 21661
    21610 Hidden Creek Dr, Rock Hall, MD 21661
    /22

    $749,900

    • Land
    • 7.9 Acres
    • $94,924 per Acre

    21610 Hidden Creek Dr, Rock Hall, MD 21661

    Enjoy a long, secluded driveway to 2,185 sq ft home sitting on 7.9 acres of mature, heavily-forested woods with waterfront views of Greys Inn Creek. The home features vaulted ceilings and has access to a private pier and dock; its perfect for boating, fishing, crabbing, or just enjoying the outdoors. Located in Rock Hall, Maryland, known for hunting, fishing, and Chesapeake Bay boating, this

    Mike Arajakis Whitetail Properties Real Estate

    21610 Hidden Creek Dr, Rock Hall, MD 21661
  • 10971 Bottom Rd, Worton, MD 21678
    10971 Bottom Rd, Worton, MD 21678
    10971 Bottom Rd, Worton, MD 21678
    /25

    $270,000

    • 2 Beds
    • 2 Baths
    • 720 Sq Ft

    10971 Bottom Rd, Worton, MD 21678

    Nestled among the farmland and waterways in Kent County is a cul de sac of new homes on Bottom Road just outside of Chestertown. The new 2 bedroom/2 bath single family home in a quiet, serene enclave is a perfect spot for your new home! This fresh and modern home offers glossy granite counters, SS appliances, and a trendy color palette. The quality of this new construction shows in the engineered

    Andy Batch Keller Williams Select Realtors of Annapolis

    10971 Bottom Rd, Worton, MD 21678
  • 22681 Wood Yard Ln, Chestertown, MD 21620
    22681 Wood Yard Ln, Chestertown, MD 21620
    /2

    $15,000

    • Land
    • 22,651 Sq Ft
    • $28,846 per Acre

    22681 Wood Yard Ln, Chestertown, MD 21620

    Half acre+ secluded wooded lot. There used to be a house on the property but county does not have well or septic records so buyer would need to perform perc test to build. There appears to be electric run to lot and there is a 16' right of way to access. Buyer to do any due diligence. Could be a great hunting property surrounded by woods and farmland!

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    22681 Wood Yard Ln, Chestertown, MD 21620
  • 6520 Swan Creek Rd, Rock Hall, MD 21661
    6520 Swan Creek Rd, Rock Hall, MD 21661
    6520 Swan Creek Rd, Rock Hall, MD 21661
    /62

    $3,150,000

    • 7 Beds
    • 6.5 Baths
    • 12,520 Sq Ft

    6520 Swan Creek Rd, Rock Hall, MD 21661

    All showings require pre screening and financial capability prior to scheduling any showing. Rarely does a property of this sort come available in Kent County Maryland! This incredible 139+/- acre Chesapeake Bay property is available in it's entirety, however the seller may consider selling the primary residence with a reduced amount of acreage under the right conditions, providing the purchaser

    William Norris Select Land & Homes, LLC

    6520 Swan Creek Rd, Rock Hall, MD 21661
  • 11981 Dewees Ln, Kennedyville, MD 21645
    11981 Dewees Ln, Kennedyville, MD 21645
    11981 Dewees Ln, Kennedyville, MD 21645
    /38

    $385,000

    • 3 Beds
    • 2.5 Baths
    • 1,270 Sq Ft

    11981 Dewees Ln, Kennedyville, MD 21645

    Come see this home in the sought after community of Village at Kennedyville. This beautiful, updated 3 bedroom 2 and 1/2 bath home is awaiting it's next owner. As you enter this home you immediately feel the pride in ownership and notice the updates. From the bright open feel of the home and gourmet kitchen featuring stainless appliances with the refrigerator replaced in 2023, the dishwasher

    Edward Beres RE/MAX Executive

    11981 Dewees Ln, Kennedyville, MD 21645
  • 6746 Quaker Neck Rd, Chestertown, MD 21620
    6746 Quaker Neck Rd, Chestertown, MD 21620
    6746 Quaker Neck Rd, Chestertown, MD 21620
    /50

    $384,000

    • 5 Beds
    • 2.5 Baths
    • 3,371 Sq Ft

    6746 Quaker Neck Rd, Chestertown, MD 21620

    Michele Palmer Doug Ashley Realtors, LLC

    6746 Quaker Neck Rd, Chestertown, MD 21620
  • 110 Trafford Dr, Chestertown, MD 21620
    110 Trafford Dr, Chestertown, MD 21620
    110 Trafford Dr, Chestertown, MD 21620
    /22

    $450,000

    • 4 Beds
    • 2.5 Baths
    • 2,880 Sq Ft

    110 Trafford Dr, Chestertown, MD 21620

    Coventry Farms—Reduced to Sell, Offers EncouragedLocated in the highly desirable Coventry Farms community, this home presents a wonderful opportunity for its next owner to bring fresh vision and personal touches. With the seller preparing for a move out of the area, the property has been reduced to reflect its current condition and to encourage a timely sale. Inside, you’ll find generous

    Agent Photo

    Debbi Rivero

    RE/MAX Advantage Realty

    (410) 406-7422

    110 Trafford Dr, Chestertown, MD 21620
  • 5916 N Main St, Rock Hall, MD 21661
    5916 N Main St, Rock Hall, MD 21661
    5916 N Main St, Rock Hall, MD 21661
    /28

    $324,999

    • 3 Beds
    • 1.5 Baths
    • 1,233 Sq Ft

    5916 N Main St, Rock Hall, MD 21661

    Welcome to this charming 3-bedroom rancher in the quaint town of Rock Hall. Featuring beautiful wood floors throughout, this cozy home is being sold as-is—perfect for buyers looking to add their own personal touch. A standout feature is the detached garage with a bathroom rough-in, currently used as an entertainment space or “man cave.” With a few updates, it could easily be transformed into a

    Christine Johnson RE/MAX Executive

    5916 N Main St, Rock Hall, MD 21661
  • 23698 L Rd, Chestertown, MD 21620
    23698 L Rd, Chestertown, MD 21620
    23698 L Rd, Chestertown, MD 21620
    /5

    $20,750

    • Land
    • 2.6 Acres
    • $7,981 per Acre

    23698 L Rd, Chestertown, MD 21620

    Property record consists of two lots for a total of 2.6 Acres zoned Village. Please notify listing agent if you intend to walk the property.

    Joe Howerton Taylor Properties

    23698 L Rd, Chestertown, MD 21620
  • 218 Camelot Dr, Chestertown, MD 21620
    218 Camelot Dr, Chestertown, MD 21620
    218 Camelot Dr, Chestertown, MD 21620
    /45

    $510,000 Open Sun 12PM - 2PM

    • 5 Beds
    • 3.5 Baths
    • 3,932 Sq Ft

    218 Camelot Dr, Chestertown, MD 21620

    Seller is motivated and can move quickly in 30 days! Welcome to 218 Camelot Drive, stunning colonial 3,932 total square feet of maintained living Situated on a beautifully landscaped corner lot in the established Coventry Farms community, this home features a fenced backyard with vinyl fencing—ideal for privacy, pets, and play. A brick paver patio with pergola and a creates multiple outdoor

    Dee Dee McCracken Coldwell Banker Realty

    218 Camelot Dr, Chestertown, MD 21620
  • 0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620
    0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620
    0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620
    /32

    $39,000

    • Land
    • 1.51 Acres
    • $25,828 per Acre

    0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620

    Largest privately held parcel in Chesapeake Landing. 8 Lots each more than 10,000 sq ft. for a total 1.51 acres. Tax map 27, lots 254-257 & 297-300 (2 contiguous lots). The site is level & wooded. Raw land near Worton's Marina. Community has a boat ramp and offers easy access to the Chesapeake Bay. Chesapeake Landing has a voluntary HOA giving you access to the boat ramp, marina and a slip for an

    Becky Schor Berkshire Hathaway HomeServices Homesale Realty

    0 Cloquet Rd Unit MDKE2005966, Chestertown, MD 21620
  • 22537 Shipyard Ln, Rock Hall, MD 21661
    22537 Shipyard Ln, Rock Hall, MD 21661
    22537 Shipyard Ln, Rock Hall, MD 21661
    /6

    $3,665,000

    • Land
    • 113 Acres
    • $32,434 per Acre

    22537 Shipyard Ln, Rock Hall, MD 21661

    Located along Shipyard Creek just outside Rock Hall, this 113-acre farm offers a strong combination of productive soils, waterfront access, and long-term investment value. The property includes approximately 100 tillable acres with primarily Mattapex soils moderately well-drained and highly rated for grain and forage production. The balance consists of woodland providing natural buffers between

    Sue Hudson National Land Realty

    22537 Shipyard Ln, Rock Hall, MD 21661
  • 0 Lot 30 Hagy Rd, Rock Hall, MD 21661
    0 Lot 30 Hagy Rd, Rock Hall, MD 21661
    0 Lot 30 Hagy Rd, Rock Hall, MD 21661
    /46

    $147,000

    • Land
    • 1 Acre
    • $147,000 per Acre

    0 Lot 30 Hagy Rd, Rock Hall, MD 21661

    Welcome to Little Neck Farm - this waterfront community has 30 homesites within a 354 acre farm with 4 miles of protected shoreline and plenty of open space where getting back to nature is possible. Lot 30 is available for sale - it is a generous level one acre lot with plenty of room to build your dream or getaway home. The lot has evergreens and crape myrtle plantings outlining a portion of the

    Cindy DelZoppo Northrop Realty

    0 Lot 30 Hagy Rd, Rock Hall, MD 21661
  • 102 Little Harbor Way, Chestertown, MD 21620
    102 Little Harbor Way, Chestertown, MD 21620
    102 Little Harbor Way, Chestertown, MD 21620
    /23

    $839,500 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    102 Little Harbor Way, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 983-3178

    102 Little Harbor Way, Chestertown, MD 21620
  • 37 Landing Ln, Chestertown, MD 21620
    37 Landing Ln, Chestertown, MD 21620
    37 Landing Ln, Chestertown, MD 21620
    /24

    $765,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    37 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath

    Julia Hilfiker Gunther-McClary Real Estate

    37 Landing Ln, Chestertown, MD 21620
  • 36 Landing Ln, Chestertown, MD 21620
    36 Landing Ln, Chestertown, MD 21620
    36 Landing Ln, Chestertown, MD 21620
    /26

    $753,500 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    36 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 819-1523

    36 Landing Ln, Chestertown, MD 21620
  • 35 Landing Ln, Chestertown, MD 21620
    35 Landing Ln, Chestertown, MD 21620
    35 Landing Ln, Chestertown, MD 21620
    /26

    $786,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    35 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like

    Julia Hilfiker Gunther-McClary Real Estate

    35 Landing Ln, Chestertown, MD 21620
  • 104 Landing Ln, Chestertown, MD 21620
    104 Landing Ln, Chestertown, MD 21620
    104 Landing Ln, Chestertown, MD 21620
    /24

    $813,900 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,192 Sq Ft

    104 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 609-5588

    104 Landing Ln, Chestertown, MD 21620
  • 25 Landing Ln, Chestertown, MD 21620
    25 Landing Ln, Chestertown, MD 21620
    25 Landing Ln, Chestertown, MD 21620
    /22

    $1,099,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,784 Sq Ft

    25 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,784 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 4 bedrooms and 3.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. There is a first floor primary bedroom for one-floor living

    Julia Hilfiker Gunther-McClary Real Estate

    25 Landing Ln, Chestertown, MD 21620
  • 21745 Centennial Ln, Rock Hall, MD 21661
    21745 Centennial Ln, Rock Hall, MD 21661
    21745 Centennial Ln, Rock Hall, MD 21661
    /24

    $359,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,413 Sq Ft

    21745 Centennial Ln, Rock Hall, MD 21661

    “PRICE IMPROVEMENT! Move-in Ready New ConstructionRancher in Rock Hall - Perfect for Retirees or Weekend Getaways at 21745 Centennial Lane, Rock Hall, MD, a brand-new 1,415 sq ft home offering single-story living just minutes from marinas, waterfront dining, and all that Rock Hall has to offer. Built by JAC Homes, this 3-bedroom, 2-bath home features an open-concept layout with abundant

    Pamela Geib Long & Foster Real Estate, Inc.

    21745 Centennial Ln, Rock Hall, MD 21661
  • 21131 Striper Run, Rock Hall, MD 21661
    21131 Striper Run, Rock Hall, MD 21661
    21131 Striper Run, Rock Hall, MD 21661
    /9

    $364,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,626 Sq Ft

    21131 Striper Run, Rock Hall, MD 21661

    New Construction Alert! Last two beautiful 3BR, 2.5 bath duplexes under construction on Striper Run in Watermans Estates. Nice open 1st floor layout with living, dining & kitchen areas, powder room and separate laundry room. Luxury vinyl plank flooring on 1st and 2nd floors, quartz counter tops and stainless appliances are included. Upstairs, there's a primary suite with walk-in closet, full

    Cindy Genther Rock Hall Properties Real Estate

    21131 Striper Run, Rock Hall, MD 21661
  • 311 Devon Dr, Chestertown, MD 21620
    311 Devon Dr, Chestertown, MD 21620
    311 Devon Dr, Chestertown, MD 21620
    /41

    $525,000

    • 4 Beds
    • 3 Baths
    • 3,504 Sq Ft

    311 Devon Dr, Chestertown, MD 21620

    REDUCED! 311 Devon Drive is located in Coventry Farms; and being located within the Chestertown town limits offers town utilities. The front entrance welcomes you with an open two-story foyer to the second-floor balcony. To the left of the front foyer is a den and to the right is a formal dining room. The foyer hall leads into a large open area that includes a large eat-in kitchen, sunroom and

    Debbie Meikle Doug Ashley Realtors, LLC

    311 Devon Dr, Chestertown, MD 21620
  • 24204 Drayton Landing Dr, Worton, MD 21678
    24204 Drayton Landing Dr, Worton, MD 21678
    24204 Drayton Landing Dr, Worton, MD 21678
    /47

    $725,000

    • 3 Beds
    • 2 Baths
    • 2,176 Sq Ft

    24204 Drayton Landing Dr, Worton, MD 21678

    Set on two peaceful acres in the highly regarded Kinnaird’s Point community, this beautifully renovated home offers modern comfort, privacy, and access to the best of Eastern Shore living. Thoughtfully updated inside and out, the property delivers a rare combination of quality upgrades, flexible space, and community water access just minutes from Chestertown. Step inside to a bright, open

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (443) 594-6295

    24204 Drayton Landing Dr, Worton, MD 21678
  • 0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
    /8

    $90,000

    • Land
    • 3.92 Acres
    • $22,959 per Acre

    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620

    Nearly 4 Acres of Wooded Privacy!Bring your vision to life on this beautiful, almost 4-acre parcel surrounded by nature. The water and sewer allocation has already been paid—a $16,200 value! The lot is mostly level with a few natural clearings throughout, offering several great options for a home site. The rear portion of the property is designated forested shrub wetlands, though it’s been

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Georgetown Rd SE Unit MDKE2005844, Chestertown, MD 21620
  • 0 Swan Creek Rd Unit MDKE2005910, Rock Hall, MD 21661
    0 Swan Creek Rd Unit MDKE2005910, Rock Hall, MD 21661
    0 Swan Creek Rd Unit MDKE2005910, Rock Hall, MD 21661
    /17

    $663,000

    • Land
    • 18.62 Acres
    • $35,607 per Acre

    0 Swan Creek Rd Unit MDKE2005910, Rock Hall, MD 21661

    Discover 18.62 acres of waterfront land on Tavern Creek, offering 1,086 feet of shoreline and stunning natural surroundings. Zoned Resource Conservation and currently tilled, this property provides a rare opportunity for those seeking space, privacy, and water access. A small portion of the shoreline lies within the flood zone; buyer to confirm buildability.

    Sarah Ulrick Rock Hall Properties Real Estate

    0 Swan Creek Rd Unit MDKE2005910, Rock Hall, MD 21661
  • 108 Little Harbor Way, Chestertown, MD 21620
    108 Little Harbor Way, Chestertown, MD 21620
    108 Little Harbor Way, Chestertown, MD 21620
    /5

    $635,000

    • Land
    • 3,920 Sq Ft
    • $7,055,556 per Acre

    108 Little Harbor Way, Chestertown, MD 21620

    Buildable waterfront lot in the Chester River Landing community. This prime location captures panoramic views of the Chester River! Just steps away from deep water boat slips, which are available for lease or purchase. Perfect location to build your dream home on the water. The Chester River Landing community amenities include docks, in-ground pool, grilling and outdoor dining area right on the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 335-6192

    108 Little Harbor Way, Chestertown, MD 21620
  • 611 Cannon St, Chestertown, MD 21620
    611 Cannon St, Chestertown, MD 21620
    611 Cannon St, Chestertown, MD 21620
    /18

    $275,000

    • 2 Beds
    • 1.5 Baths
    • 920 Sq Ft

    611 Cannon St, Chestertown, MD 21620

    This 2-bedroom, 1.5-bath bungalow offers a bright, open layout with updates throughout. The home features a sun-filled front room, an eat-in kitchen with new butcher block seating and updated appliances, and a fully renovated bathroom with new tile and a modern vanity. A rear utility room with laundry provides extra storage and access to a small backyard—perfect for gardening or relaxing

    Hayley Norris Select Land & Homes, LLC

    611 Cannon St, Chestertown, MD 21620
  • 106 Landing Ln, Chestertown, MD 21620
    106 Landing Ln, Chestertown, MD 21620
    106 Landing Ln, Chestertown, MD 21620
    /24

    $799,900 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,092 Sq Ft

    106 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space

    Julia Hilfiker Gunther-McClary Real Estate

    106 Landing Ln, Chestertown, MD 21620
  • 0 Little Harbor Way Unit 1, Chestertown, MD 21620
    0 Little Harbor Way Unit 1, Chestertown, MD 21620
    0 Little Harbor Way Unit 1, Chestertown, MD 21620
    /25

    $1,459,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,231 Sq Ft

    0 Little Harbor Way Unit 1, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,231 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room, with gas fireplace ,to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 835-9021

    0 Little Harbor Way Unit 1, Chestertown, MD 21620
  • 104 Little Harbor Way, Chestertown, MD 21620
    104 Little Harbor Way, Chestertown, MD 21620
    104 Little Harbor Way, Chestertown, MD 21620
    /23

    $849,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,980 Sq Ft

    104 Little Harbor Way, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large

    Julia Hilfiker Gunther-McClary Real Estate

    104 Little Harbor Way, Chestertown, MD 21620
  • 105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    105 High St, Chestertown, MD 21620
    /48

    $1,395,500

    • 5 Beds
    • 4.5 Baths
    • 3,243 Sq Ft

    105 High St, Chestertown, MD 21620

    Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    105 High St, Chestertown, MD 21620
  • 0 Still Pond Creek Rd Unit MDKE2005888, Worton, MD 21678
    0 Still Pond Creek Rd Unit MDKE2005888, Worton, MD 21678
    0 Still Pond Creek Rd Unit MDKE2005888, Worton, MD 21678
    /9

    $85,000

    • Land
    • 1.2 Acres
    • $70,833 per Acre

    0 Still Pond Creek Rd Unit MDKE2005888, Worton, MD 21678

    The last buildable lot in the Cheerful Echoes neighborhood is perc approved and ready for improvement. NO HOA! With a gentle slope and plenty of room for the backyard of your dreams, a walkout lower level can open to a patio, gardens, etc... you name it! Just a few miles from the Worton Community Center and the walking trails at Worton Park, and a convenient drive to Chestertown, Middletown, and

    Liddy Campbell TTR Sotheby's International Realty

    0 Still Pond Creek Rd Unit MDKE2005888, Worton, MD 21678
  • 222 Mount Vernon Ave, Chestertown, MD 21620
    222 Mount Vernon Ave, Chestertown, MD 21620
    222 Mount Vernon Ave, Chestertown, MD 21620
    /29

    $439,999

    • 4 Beds
    • 2 Baths
    • 1,656 Sq Ft

    222 Mount Vernon Ave, Chestertown, MD 21620

    HIGHLY MOTIVATED SELLERS — bring us an offer! This historic 1916 home is comfortable, convenient, and move-in ready. They don’t build houses like this anymore! Featuring 4 bedrooms and 2 full baths, this home is adjacent to Washington College and walking distance from downtown Chestertown. Three finished levels and high ceilings make the home feel roomier than the square footage suggests.

    Kellie Gough McLendon Long & Foster Real Estate, Inc.

    222 Mount Vernon Ave, Chestertown, MD 21620
  • 31695 Olivet Cir, Galena, MD 21635
    31695 Olivet Cir, Galena, MD 21635
    31695 Olivet Cir, Galena, MD 21635
    /18

    $200,000

    • 3 Beds
    • 2 Baths
    • 1,701 Sq Ft

    31695 Olivet Cir, Galena, MD 21635

    Welcome Home to 31695 Olivet Circle, this 3 bedroom 2 bath home is a great started home! Beautiful property with lots of possibilities! Off the beaten path & surrounded by nature with a detached garage.

    Donnie Horton RE/MAX Chesapeake

    31695 Olivet Cir, Galena, MD 21635
  • 8620 Park Dr, Chestertown, MD 21620
    8620 Park Dr, Chestertown, MD 21620
    8620 Park Dr, Chestertown, MD 21620
    /66

    $499,900

    • 4 Beds
    • 2,524 Sq Ft

    8620 Park Dr, Chestertown, MD 21620

    Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (estimate). 4 bedrooms, 2.5 Bathrooms. 1⁄2 basement with laundry room and fix-it shop/work bench with 2 crawl spaces. Attached two-car garage with abundant built-in shelving and free-standing cabinets for lots of storage space with garage door opener on each of 2 doors. Forced Hot

    Doug Ashley Doug Ashley Realtors, LLC

    8620 Park Dr, Chestertown, MD 21620
  • 7844 Chester Ct, Chestertown, MD 21620
    7844 Chester Ct, Chestertown, MD 21620
    7844 Chester Ct, Chestertown, MD 21620
    /51

    $695,000

    • 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 season

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 648-9684

    7844 Chester Ct, Chestertown, MD 21620
  • #2 Lawton Ave, Rock Hall, MD 21661
    #2 Lawton Ave, Rock Hall, MD 21661
    #2 Lawton Ave, Rock Hall, MD 21661
    /17

    $1,125,000

    • Land
    • 22,215 Sq Ft
    • $2,205,882 per Acre

    #2 Lawton Ave, Rock Hall, MD 21661

    Over half an acre of prime bayfront property! Build a beautiful home on popular Lawton Avenue, the Gratitude neighborhood in Rock Hall. Enjoy sunsets, spectacular views of the bay, and additional views of Swan Creek in back. Spend idyllic afternoons watching the boats sail by! Lawton Ave offers privacy, but is only a short stroll to multiple restaurants, the town beach, and many marinas; there is

    Lynn Hilfiker Gunther-McClary Real Estate

    #2 Lawton Ave, Rock Hall, MD 21661
  • 13983 Turners Point Rd, Kennedyville, MD 21645
    13983 Turners Point Rd, Kennedyville, MD 21645
    13983 Turners Point Rd, Kennedyville, MD 21645
    /51

    $599,000

    • 2 Beds
    • 2.5 Baths
    • 4,054 Sq Ft

    13983 Turners Point Rd, Kennedyville, MD 21645

    Impeccably kept Kentmore Park home with a white picket fence. Over two acres with private rear yard for relaxation. Adorable brick outbuilding for storage, home office, man cave or she shed. Gazebo for al fresco dining, afternoon card games or just enjoying nature. Two additional sheds for storing just about anything. Habitat for many bird species in season. Owl, Heron and Eagle territory year

    Patricia Kern Gunther-McClary Real Estate

    13983 Turners Point Rd, Kennedyville, MD 21645

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