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Kent County MD Homes for Sale with Acreage

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  • /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
  • /47

    $725,000 Open Sat 11:30AM - 1:30PM

    • 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
  • /51

    $1,975,000

    • 5 Beds
    • 3 Baths
    • 3,915 Sq Ft

    14183 Roberts Dr, Galena, MD 21635

    Experience riverfront living on the Sassafras River with this exceptional home on just over 13 acres. There’s room for everyone with 5/6 bedrooms, 3 full baths, and two kitchens. Enjoy sunrise over the river through the primary bedroom’s expansive window, then watch the eagles and osprey while sipping coffee on the dock. This home boasts a jet ski dock, and both fixed and floating docks with 3

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 609-5094

    14183 Roberts Dr, Galena, MD 21635
  • /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
  • /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
  • /9

    $1,150,000

    • 3 Beds
    • 2 Baths
    • 1,944 Sq Ft

    12400 Woods Rd, Worton, MD 21678

    Tucked away along the quiet shores of Still Pond Creek, this cedar cabin offers a rare blend of privacy, comfort, and natural beauty. Surrounded by mature woods and set on a peaceful stretch of waterfront, this 1,944 square foot home features 3 bedrooms, 2 bathrooms, a spacious screened-in porch perfect for crab feasts, a private beach and pier with 2'+ MLW improved with bilk head installed by

    Stacy Kendall Cross Street Realtors LLC

    12400 Woods Rd, Worton, MD 21678
  • /6

    $14,000

    • Land
    • 2.08 Acres
    • $6,731 per Acre

    23665 Smithville Rd, Worton, MD 21678

    This 2.08-acre corner lot at the intersection of Smithville Road and Newtown Road presents a strong opportunity for buyers seeking flexibility and long-term value. The property offers a usable layout with road frontage on two sides, providing convenient access and multiple points of entry.Ideal for hunting and camping, the land supports a range of recreational uses while also offering

    Jack Boniface Cross Street Realtors LLC

    23665 Smithville Rd, Worton, MD 21678
  • /6

    $12,000

    • Land
    • 1.75 Acres
    • $6,857 per Acre

    23737 Smithville Rd, Worton, MD 21678

    This 1.75-acre wooded lot offers a strong opportunity for buyers seeking flexibility and value. The property provides space for recreational use and the potential for a long-term investment.Ideal for hunting and camping, the land offers a range of outdoor activities. With a location just 5 miles from Worton Creek Marina, this brings you convenient access for boating the Chesapeake Bay and its

    Jack Boniface Cross Street Realtors LLC

    23737 Smithville Rd, Worton, MD 21678
  • /26

    $449,000

    • 3 Beds
    • 2.5 Baths

    1 Idlewhile Ave Unit 4, Betterton, MD 21610

    Crew's Landing 3 bedroom Townhouse, located in Betterton, The Jewel of the Chesapeake. This 12 unit complex has become a premier waterfront community on the upper Bay. Located on a 5 acre setting of beautiful landscape offering carefree living. It includes a community dock and a great private sandy beach. The unit has had upgrades with wood plank tile floors, kitchen with granite countertops, and

    Ashton Kelley Gunther-McClary Real Estate

    1 Idlewhile Ave Unit 4, Betterton, MD 21610
  • /15

    $550,000

    • Land
    • 50 Acres
    • $11,000 per Acre

    0 Bradford Johnson Rd, Golts, MD 21635

    Excellent Opportunity to own a great 50+/- acre hunting and recreational property in northern Kent County Maryland. Diverse wooded acres provide for good privacy with reasonable road frontage and an excellent habitat lending an upper hand for Deer, Turkey and other diverse wildlife species. The convenience of this wooded parcel is another reason to move it to the top of your list at around 20

    BRIAN MORRIS The Land Group

    0 Bradford Johnson Rd, Golts, MD 21635
  • /82

    $1,495,000

    • 4 Beds
    • 3.5 Baths
    • 3,383 Sq Ft

    8276 Broad Neck Rd, Chestertown, MD 21620

    Wait until you see this! Impecably maintained brick house on nearly 20 acres, overlooking a pond with tons of privacy. 2 large outbuildings. High-end upgrades and fixtures. The house has 4 bedrooms and 3.5 baths. A primary owner's suite on the main floor and an additional owner's suite on the second floor. Beautiful hardwood floors throughout. The main floor features a bar room and an office.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    8276 Broad Neck Rd, Chestertown, MD 21620
  • /7

    $675,000

    • Land
    • 14.11 Acres
    • $47,838 per Acre

    14200 Metasequoia Ct, Galena, MD 21635

    It is a rare opportunity for a private waterfront lot off the Sassafras River to come available. This 14 acre parcel of land is located above the bridge in a well established small community of Gentle Winds. Scenic and tranquil area for birding watching, kayaking or taking a short boat ride to restaurants located down the river. With this 14 acre lot, there are open areas and woods to play with.

    Ashton Kelley Gunther-McClary Real Estate

    14200 Metasequoia Ct, Galena, MD 21635
  • /45

    $489,900

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    201 Ericsson Ave, Betterton, MD 21610

    Phenomenal 3.75 acres+- in sought after Betterton. The hidden bay front town retreat from the past.Rolling pasture like setting with specimen trees. Farmhouse style home with pinewood floors perched up high overlooking the property. Detached garage and 2 other large sheds on the property. Craftsman's dream. Deer and all other creatures abound. Short walk to town beach, gazebo and boat ramp.

    Jonathan Olsavsky Coldwell Banker Waterman Realty

    201 Ericsson Ave, Betterton, MD 21610
  • /62

    $3,500,000

    • 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
  • /5

    $21,000

    • Land
    • 2.6 Acres
    • $8,077 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
  • /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
  • /46

    $155,000

    • Land
    • 1 Acre
    • $155,000 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
  • /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
  • /17

    $995,000

    • Land
    • 18.62 Acres
    • $53,437 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
  • /9

    $95,000

    • Land
    • 1.2 Acres
    • $79,167 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
  • /53

    $499,900

    • 4 Beds
    • 2.5 Baths
    • 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

    Doug Ashley Doug Ashley Realtors, LLC

    8620 Park Dr, Chestertown, MD 21620
  • /62

    $625,000

    • 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
  • /15

    $59,999

    • Land
    • 1.09 Acres
    • $55,045 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
  • /12

    $164,000

    • Land
    • 2.15 Acres
    • $76,279 per Acre

    7224 Rock Hall Rd, Rock Hall, MD 21661

    Discover the charm of Kent County’s rural lifestyle on this fenced, 2.15-acre cleared lot. Perfectly situated along Rock Hall Road, the property features an existing two-car garage, a 6’x8’ storage shed, and mature trees framing vast pastoral views. With electric service and an existing well already in place, it’s ready for your vision—whether that’s building your dream home, creating a weekend

    Cindy Genther Rock Hall Properties Real Estate

    7224 Rock Hall Rd, Rock Hall, MD 21661
  • /21

    $40,000

    • Land
    • 1 Acre
    • $40,000 per Acre

    0 Allens Ln Unit MDKE2005580, Rock Hall, MD 21661

    Welcome to your slice of country solitude! This wooded 1-acre lot comes with a sewer allocation already in place so no septic headaches here. You’ll just need to add a well... unless, of course, you discover one hiding on the property. (The county has no records, but there’s an old house/structure tucked in the trees, so who knows what secrets it holds.) The sewer is serviced by a grinder pump,

    Micheal Vakas EXP Realty, LLC

    0 Allens Ln Unit MDKE2005580, Rock Hall, MD 21661
  • /117

    $819,000

    • 4 Beds
    • 3 Baths
    • 3,388 Sq Ft

    14540 Stirrup Ln, Galena, MD 21635

    Tucked away in the exclusive waterfront enclave of Fox Hole Estates, this serene retreat offers an exceptional blend of luxury, privacy, and natural beauty. Overlooking the beautiful Sassafras River, this beautifully renovated residence is designed to impress the discerning buyer seeking peace without compromise. The home’s inviting interior features rich hardwood floors, vaulted ceilings, and

    Ben Esh Astoria Realty Advisors LLC

    14540 Stirrup Ln, Galena, MD 21635
  • /19

    $3,000,000

    • Land
    • 87.34 Acres
    • $34,349 per Acre

    0 Cromwell Clark Rd, Chestertown, MD 21620

    Potential for Residential Development!87 Acre land tract that is annexed into the town of Chestertown and is served with municipal services. The property is zoned residential (R-3 and R-4) and has been previously studied for residential development. The 44± acres of farmland are surrounded by a forested buffer that may nicely serve the future layout and privacy of a residential community.

    BRIAN MORRIS The Land Group

    0 Cromwell Clark Rd, Chestertown, MD 21620
  • /3

    $150,000

    • Land
    • 2 Acres
    • $75,000 per Acre

    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620

    Beautiful 2-Acre Lot – Build Your Dream Home! Come and experience the charm of this picturesque 2-acre lot, perfectly priced and ready for your dream home. Nestled among scenic farms and mature trees, this serene setting offers the perfect blend of privacy and natural beauty.Located just minutes from the water, you'll enjoy easy access to nearby Tolchester Beach—only about 2 miles west—and

    Sebrin Adem RE/MAX Allegiance

    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
  • /43

    $5,900,000

    • 6 Beds
    • 4.5 Baths
    • 4,214 Sq Ft

    5135 Crosby Rd, Rock Hall, MD 21661

    A true sportsman’s paradise and a family compound, this impressive 212 +/-acre farm offers breathtaking water views and unparalleled outdoor recreation. The solidly built, colonial style home is designed to capture the beauty of Davis Creek from nearly every room. The kitchen and dining area are perfectly positioned for waterfront entertaining, seamlessly flowing into the family room with gas

    Courtney Chipouras TTR Sotheby's International Realty

    5135 Crosby Rd, Rock Hall, MD 21661
  • /4

    $1,250,000

    • Land
    • 86 Acres
    • $14,535 per Acre

    Lot 1 Carroll Clark Rd, Galena, MD 21635

    Lot 1 is +/- 86 acres of prime development land in Kent County's Rt. 301 Growth Corridor. With +2,500 ft along Rt. 301 and 1,295 ft along Carroll Clark Rd, this property offers easy access to Middletown, DE and Rt. 1. The property is zoned Employment Center and qualifies for Kent County and Maryland State incentives. Approximately 46 acres are currently in ag use. There is a cell tower on the

    Cindy Genther Rock Hall Properties Real Estate

    Lot 1 Carroll Clark Rd, Galena, MD 21635
  • /3

    $1,250,000

    • Land
    • 49.83 Acres
    • $25,085 per Acre

    0 Rock Hall Rd, Rock Hall, MD 21661

    50 acres of mixed use development property within Rock Hall town limits. Great location with access via state highway/MD Rt. 20, and 3 town roads; almost 1000 ft of road frontage. The property is partially cleared and includes a small area of wetlands that would make a nice pocket park within the development. Public water and sewer service hook ups are available. Fiber optic cables are buried

    Robin Fithian Rock Hall Properties Real Estate

    0 Rock Hall Rd, Rock Hall, MD 21661
  • /2

    $250,000

    • Land
    • 5 Acres
    • $50,000 per Acre

    5898 Williams St, Rock Hall, MD 21661

    Welcome to 5898 Williams Street, Rock Hall, MD! This 5-acre cleared parcel offers an exciting development opportunity in the heart of Rock Hall. With public water and sewer available, the property provides excellent development potential. Formerly zoned MCI, it is now zoned residential under the newly adopted Rock Hall 2040 Comprehensive Plan, opening the door for possible subdivision. Situated

    Cindy Genther Rock Hall Properties Real Estate

    5898 Williams St, Rock Hall, MD 21661
  • /2

    $29,000

    • Land
    • 2 Acres
    • $14,500 per Acre

    0 Melitota Ln, Chestertown, MD 21620

    2-acre wooded parcel on L Road. Short distance to Chestertown and amenities. See Documents for additional information. Out of Town Seller will pay for perk testing with Buyer making local arrangements. Seller has paperwork from the County to proceed when needed.

    Jo Ann Edwards The Hogans Agency

    0 Melitota Ln, Chestertown, MD 21620
  • /8

    $150,000

    • Land
    • 2 Acres
    • $75,000 per Acre

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620

    Sebrin Adem RE/MAX Allegiance

    0 Caulks Field Rd Unit MDKE2005120, Chestertown, MD 21620
  • /2

    $58,000

    • Land
    • 1 Acre
    • $58,000 per Acre

    11729 Saint James Newtown Rd, Worton, MD 21678

    Dee Dee Miller Long & Foster Real Estate, Inc.

    11729 Saint James Newtown Rd, Worton, MD 21678
  • /63

    $695,000 Open Sat 11AM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,566 Sq Ft

    10087 John Carvill Rd, Chestertown, MD 21620

    Toad Hall, as the current owners affectionately call it, is located in a natural wooded setting on Fairlee Creek in Great Oak Estates just minutes from the Chesapeake Bay. Peaceful water views from almost every room in the home create the feeling of living in a tree house, and the dock is just steps away down the hillside - no flood insurance needed. Enter the house through a split foyer with a

    Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

    10087 John Carvill Rd, Chestertown, MD 21620
  • /30

    $380,000

    • 4 Beds
    • 2 Baths
    • 1,794 Sq Ft

    32287 Quinn Rd, Massey, MD 21650

    Just off Route 301 for commuters, but located in the country with privacy, space for animals, hobbies, and entertaining. Large detached garage with storage space above, full unfinished basement, fenced pasture area, and inground pool. So much potential here, come with vision and make it your own!

    John Carroll Village Real Estate Company LLC

    32287 Quinn Rd, Massey, MD 21650
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