21

Homes for Sale in Dorchester County MD with 5-Bedrooms

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  • 5640 Thompsontown Rd, East New Market, MD 21631
    5640 Thompsontown Rd, East New Market, MD 21631
    5640 Thompsontown Rd, East New Market, MD 21631
    /66

    $425,000

    • 6 Beds
    • 3 Baths
    • 2,568 Sq Ft

    5640 Thompsontown Rd, East New Market, MD 21631

    Welcome to your own private slice of Maryland's Eastern Shore! Nestled on over 8 acres in picturesque East New Market, this one-of-a-kind country estate offers the perfect blend of space, functionality, and rural charm.Originally built in 1974, the home was thoughtfully expanded in 1999 with a spacious Colonial addition, creating an impressive residence featuring 6 generously sized bedrooms

    Agent Photo

    O'Ranti J Robinson

    EXP Realty, LLC

    5640 Thompsontown Rd, East New Market, MD 21631
  • 964 Taylors Island Rd, Madison, MD 21648
    964 Taylors Island Rd, Madison, MD 21648
    964 Taylors Island Rd, Madison, MD 21648
    /107

    $8,950,000

    $950K PRICE DROP
    • 24 Beds
    • 13 Baths
    • 9,583 Sq Ft

    964 Taylors Island Rd, Madison, MD 21648

    Parsons Creek Farm - A 255+/- Acre, Multi-Residence, Deep-Water, Waterfowl & Wildlife Estate at the Confluence of Parsons Creek and the Little Choptank River This once-in-a-lifetime Chesapeake Bay legacy holding is set upon 255.47 extraordinary acres of waterfront, wetlands, upland forest, and meticulously curated wildlife habitat making Parsons Creek Farm one of the most sophisticated private

    Sue Hudson National Land Realty, LLC

    964 Taylors Island Rd, Madison, MD 21648
  • 815 Locust St, Cambridge, MD 21613
    815 Locust St, Cambridge, MD 21613
    /2

    $175,000

    • 5 Beds
    • 3 Baths
    • 2,752 Sq Ft

    815 Locust St, Cambridge, MD 21613

    INVESTMENT OPPORTUNITY IN HISTORIC DOWNTOWN CAMBRIDGE! This unique duplex, located in the heart of Historic Downtown Cambridge, offers plenty of potential for the savvy investor. The property has a special exception and is equipped with 3 gas meters and 3 electric meters. In the past when configured as a duplex, the property featured a 3-bedroom, 1-bath upper-level unit and a 2-bedroom, 1-bath

    Melissa Tippett TTR Sotheby's International Realty

    815 Locust St, Cambridge, MD 21613
  • 709 Church St, Cambridge, MD 21613
    709 Church St, Cambridge, MD 21613
    709 Church St, Cambridge, MD 21613
    /35

    $615,000

    $34K PRICE DROP
    • 8 Beds
    • 3 Baths
    • 5,000 Sq Ft

    709 Church St, Cambridge, MD 21613

    A rare opportunity in Cambridge Historic District, 709 Church Street is an extensively renovated American Four-Square set on a triple corner lot with approximately 5,000 square feet of space and remarkable flexibility. This beautifully finished first floor includes 3-4 bedrooms (including a primary ensuite) and 2 additional bathrooms. Large eat-in island kitchen is gorgeous, and you can stack the

    Edward Cartwright Benson & Mangold, LLC

    709 Church St, Cambridge, MD 21613
  • 4808 Saltmarsh Rd, Madison, MD 21648
    4808 Saltmarsh Rd, Madison, MD 21648
    4808 Saltmarsh Rd, Madison, MD 21648
    /119

    $1,399,999

    $100K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 5,087 Sq Ft

    4808 Saltmarsh Rd, Madison, MD 21648

    Endless westerly vistas stretch across Madison Bay, delivering breathtaking sunsets that feel like a private showing each and every evening. This is more than a home—it’s a waterfront sanctuary designed for those who expect their lifestyle to be as elevated as their surroundings. Welcome to Saltmarsh, an extraordinary 8.5-acre estate where luxury, privacy, and coastal beauty converge. With 5

    Kenneth Jester Coldwell Banker Realty

    4808 Saltmarsh Rd, Madison, MD 21648
  • 314 Mill St, Cambridge, MD 21613
    314 Mill St, Cambridge, MD 21613
    314 Mill St, Cambridge, MD 21613
    /88

    $769,000

    Open Sun 2:30PM - 4PM
    • 10 Beds
    • 5 Baths
    • 6,639 Sq Ft

    314 Mill St, Cambridge, MD 21613

    Step back in time to the Gilded Age! Built in 1912 by "Colonel" Albanus Phillips, this magnificent historic estate offers rare scale, classic elegance, and timeless charm in the heart of Cambridge. Spanning over 6,600 square feet, this impressive residence features 10 spacious bedrooms and 4.5 baths, offering extraordinary flexibility for large-scale living, multi-generational arrangements, or

    Valerie Brown Coldwell Banker Realty

    314 Mill St, Cambridge, MD 21613
  • 1510 Crocheron Rd, Toddville, MD 21672
    1510 Crocheron Rd, Toddville, MD 21672
    1510 Crocheron Rd, Toddville, MD 21672
    /63

    $1,690,000

    • 7 Beds
    • 3 Baths
    • 4,308 Sq Ft

    1510 Crocheron Rd, Toddville, MD 21672

    A rare opportunity on the Honga River! Jenny Island Hunt Club offers a recreational property spanning 156 acres with an established hunt club marketed through Gage Outdoors Expeditions and short-term airbnb rental business. This active, turnkey operation generates six figures in income, with multiple bookings already in place for the upcoming 2026-2027 hunting season. The 7-bedroom, 3-bath

    Leo Kuneman Meredith Fine Properties

    1510 Crocheron Rd, Toddville, MD 21672
  • 313 Washington St, Cambridge, MD 21613
    313 Washington St, Cambridge, MD 21613
    313 Washington St, Cambridge, MD 21613
    /18

    $185,500

    • 5 Beds
    • 2 Baths
    • 1,554 Sq Ft

    313 Washington St, Cambridge, MD 21613

    Unlock the potential of this duplex located in downtown Cambridge! Whether you're looking to expand your investment portfolio or generate rental income, this property offers plenty of opportunity. The first unit features 3 bedrooms and 1 full bathroom, while the second unit offers 2 bedrooms and 1 full bathroom, providing flexibility for long-term tenants, owner-occupants, or future rental

    Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    313 Washington St, Cambridge, MD 21613
  • 5207 Brooks Rd, Woolford, MD 21677
    5207 Brooks Rd, Woolford, MD 21677
    5207 Brooks Rd, Woolford, MD 21677
    /43

    $1,495,000

    • 7 Beds
    • 5 Baths
    • 4,072 Sq Ft

    5207 Brooks Rd, Woolford, MD 21677

    McNeil Pointe is a unique, coveted, 2-mile long peninsula of luxury homes. Nestled within the serene enclave of McKeil Pointe, this exquisite 7-bedroom, 5.5-bathroom farmhouse-style residence offers an unparalleled blend of luxury and comfort, set against a backdrop of lush landscapes and tranquil water features. Spanning approximately 5000+/- square feet, this home is a true sanctuary, designed

    Craig Linthicum Benson & Mangold, LLC

    5207 Brooks Rd, Woolford, MD 21677
  • 309 Glenburn Ave, Cambridge, MD 21613
    309 Glenburn Ave, Cambridge, MD 21613
    309 Glenburn Ave, Cambridge, MD 21613
    /51

    $580,000

    $45K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 3,954 Sq Ft

    309 Glenburn Ave, Cambridge, MD 21613

    This is a beautifully updated and well-maintained Four Square located in Cambridge's Historic District. It is a grand house for entertaining both inside and out. In addition to the 5 bedrooms and 3.5 baths in the Manor House, the property boasts 2 additional buildings on the .57 acre lot filled with specimen flowers, shrubs and trees. 1 building, originally built as a Montessori school, is well

    Mary Losty Compass

    309 Glenburn Ave, Cambridge, MD 21613
  • 5253 Ragged Point Rd, Cambridge, MD 21613
    5253 Ragged Point Rd, Cambridge, MD 21613
    5253 Ragged Point Rd, Cambridge, MD 21613
    /84

    $1,250,000

    • 5 Beds
    • 3.5 Baths
    • 4,933 Sq Ft

    5253 Ragged Point Rd, Cambridge, MD 21613

    Eastern Shore Waterfront Estate Welcome to a true sportsman’s paradise tucked along the shores of the Chesapeake Bay—where space, privacy, and waterfront living come together in a BIG way. Built in 1988 and spanning nearly 5,000+/- square feet, this one checks boxes most properties can’t even reach... 5 Bedrooms | 3.5 Baths | 4,933+/- Sq Ft Step inside and you’ll find: • A massive eat-in country

    Craig Linthicum Benson & Mangold, LLC

    5253 Ragged Point Rd, Cambridge, MD 21613
  • 1307 Broadview Dr, Cambridge, MD 21613
    1307 Broadview Dr, Cambridge, MD 21613
    1307 Broadview Dr, Cambridge, MD 21613
    /94

    $975,000

    $125K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 2,740 Sq Ft

    1307 Broadview Dr, Cambridge, MD 21613

    MAJOR PRICE IMPROVEMENT of nearly $225K since first listed- Perfectly positioned on 4.49 private acres at the end of a quiet dead-end road, this stunning property boasts over 2,700 square feet, five bedrooms, and an incredible 1,000 feet of water frontage—creating a rare combination of space, privacy, and panoramic views of coveted Little Choptank River.Designed and built by an architect for

    Jennifer Chaney Chaney Homes, LLC

    1307 Broadview Dr, Cambridge, MD 21613
  • 1713 Doeller Rd, Fishing Creek, MD 21634
    1713 Doeller Rd, Fishing Creek, MD 21634
    1713 Doeller Rd, Fishing Creek, MD 21634
    /112

    $3,200,000

    • 5 Beds
    • 5.5 Baths
    • 3,901 Sq Ft

    1713 Doeller Rd, Fishing Creek, MD 21634

    Introducing Riverside Lodge, a one-of-a-kind private waterfront sporting estate on Maryland's Eastern Shore. Spanning 386+/- acres overlooking the Honga River and the Chesapeake Bay, this extraordinary retreat is anchored by a beautifully appointed 5 bedroom, 5.5 bath waterfront lodge designed for both entertaining and comfortable extended stays or full time residence. Surrounded by exceptional

    Leo Kuneman Meredith Fine Properties

    1713 Doeller Rd, Fishing Creek, MD 21634
  • 16 Buena Vista Ave, Cambridge, MD 21613
    16 Buena Vista Ave, Cambridge, MD 21613
    16 Buena Vista Ave, Cambridge, MD 21613
    /38

    $384,000

    $50K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 2,781 Sq Ft

    16 Buena Vista Ave, Cambridge, MD 21613

    Welcome to 16 Buena Vista Avenue! This very spacious 5 bedroom, 3.5 bath brick rancher is situated on an attractive corner lot in the sought-after, quiet Algonquin neighborhood, within walking distance of Sandy Hill Elementary School. The home offers generous living spaces, a brick fireplace and lots of natural light. A large detached outbuilding features an oversized two-car garage with a

    Leo Kuneman Meredith Fine Properties

    16 Buena Vista Ave, Cambridge, MD 21613
  • 5332 Ragged Point Rd, Cambridge, MD 21613
    5332 Ragged Point Rd, Cambridge, MD 21613
    5332 Ragged Point Rd, Cambridge, MD 21613
    /65

    $1,399,000

    $101K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 4,488 Sq Ft

    5332 Ragged Point Rd, Cambridge, MD 21613

    Set on 10 remarkably private acres in Dorchester County’s scenic Neck District, this custom-built waterfront retreat commands sweeping views of the Middle Chesapeake Bay and offers the rare combination of space, comfort, and true Eastern Shore serenity. With over 4,500 sq. ft., 6 bedrooms, 4.5 baths, rip-rapped shoreline, and exceptional indoor and outdoor living spaces, this is a property

    Sharon Spedden Sharon Real Estate P.C.

    5332 Ragged Point Rd, Cambridge, MD 21613
  • 5951 Ross Neck Rd, Cambridge, MD 21613
    5951 Ross Neck Rd, Cambridge, MD 21613
    5951 Ross Neck Rd, Cambridge, MD 21613
    /55

    $599,900

    $100K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,184 Sq Ft

    5951 Ross Neck Rd, Cambridge, MD 21613

    Completely renovated from top to bottom, this exceptional property offers a rare opportunity to enjoy the Eastern Shore lifestyle with the privacy, acreage, and storage many waterfront buyers are seeking—without the waterfront maintenance. Situated on nearly 7 secluded acres in the highly sought-after Neck District of Dorchester County, this property is just minutes from both the public boat ramp

    Sharon Spedden Sharon Real Estate P.C.

    5951 Ross Neck Rd, Cambridge, MD 21613
  • 1632 Steamboat Wharf Rd, Fishing Creek, MD 21634
    1632 Steamboat Wharf Rd, Fishing Creek, MD 21634
    1632 Steamboat Wharf Rd, Fishing Creek, MD 21634
    /49

    $699,900

    • 7 Beds
    • 2.5 Baths
    • 2,204 Sq Ft

    1632 Steamboat Wharf Rd, Fishing Creek, MD 21634

    THE ORIGINAL HOME OF "CAPTAIN JOHNNIE" BUILT IN 1920 AND TOTALLY RESTORED. EXPANSIVE WATER-VIEWS WITH 300 FEET OF RIP RAP/BULK HEADING. PERFECT FOR YEAR ROUND LIVING, WEEKLY VACATION RENTAL OR VACATION HOME . BEAUTIFUL HARDWOOD FLOORS, FULLY EQUIPPED EAT IN KITCHEN, HUGE FAMILY/GREAT ROOM WITH WALL MOUNTED TV . HOME IS FULLY FURNISHED AND EXCEPTIONALLY EQUIPPED - EVERYTHING EXCEPT POOL/CARD TALBE

    Jeffrey Robinson Douglas Realty LLC

    1632 Steamboat Wharf Rd, Fishing Creek, MD 21634
  • 1621 Terrapin Cir, Cambridge, MD 21613
    1621 Terrapin Cir, Cambridge, MD 21613
    1621 Terrapin Cir, Cambridge, MD 21613
    /100

    $360,000

    • 5 Beds
    • 3 Baths
    • 2,610 Sq Ft

    1621 Terrapin Cir, Cambridge, MD 21613

    Welcome home to 1621 Terrapin Circle, a beautifully crafted Like New Colonial nestled in the sought-after Blackwater Landing community of Cambridge, MD. This spacious 5 bedroom, 3 bath home offers 2,610 square feet of thoughtfully designed living space, ready for you to move right in and start making memories.Step inside to find an open, light-filled layout perfect for everyday living and

    Dale Hunter Bayside Realty

    1621 Terrapin Cir, Cambridge, MD 21613
  • 2144 Hoopersville Rd, Fishing Creek, MD 21634
    2144 Hoopersville Rd, Fishing Creek, MD 21634
    2144 Hoopersville Rd, Fishing Creek, MD 21634
    /59

    $799,000

    • 6 Beds
    • 4.5 Baths
    • 3,648 Sq Ft

    2144 Hoopersville Rd, Fishing Creek, MD 21634

    Private Eastern Shore retreat with panoramic water views! This spacious newly renovated 6 bedroom, 4.5 bath home offers an abundance of room for family, guests and entertaining, with beautiful water views and a peaceful, private setting. Currently operating as an Airbnb and family retreat, the property is on track to generate approximately $40,000–$50,000 in rental income this year, with

    Leo Kuneman Meredith Fine Properties

    2144 Hoopersville Rd, Fishing Creek, MD 21634
  • 1311 Race St, Cambridge, MD 21613
    1311 Race St, Cambridge, MD 21613
    1311 Race St, Cambridge, MD 21613
    /102

    $420,000

    $75K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,929 Sq Ft

    1311 Race St, Cambridge, MD 21613

    ***Significant price reduction, and ready to entertain your offer!***Grand and beautifully updated, this circa‑1900 residence offers timeless architectural charm on 1.67 acres of land just moments from downtown and the waterfront. A welcoming wrap‑around porch with ceiling fans, sets the tone, perfect for relaxing and entertaining. The expansive grounds-fenced on three sides-include a spacious

    Linda Perry Long & Foster Real Estate, Inc.

    1311 Race St, Cambridge, MD 21613
  • 705 Church St, Cambridge, MD 21613
    705 Church St, Cambridge, MD 21613
    705 Church St, Cambridge, MD 21613
    /65

    $399,000

    $121K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 3,510 Sq Ft

    705 Church St, Cambridge, MD 21613

    Welcome to your dream home! This beautifully updated property offers 5 spacious bedrooms and 3 full bathrooms, perfect for comfortable living and entertaining.Hot Features You’ll Love:Brand new modern kitchen with all new appliances , Gorgeous new flooring throughout, Completely renovated bathrooms, Fresh new paint inside and out, Large backyard- perfect for family gatherings,

    George Nguyen Blufin Realty, LLC.

    705 Church St, Cambridge, MD 21613
Maryland

5-Bedroom Homes for Sale in Dorchester County, MD

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