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Dorchester County MD Homes for Sale with Acreage

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  • /117

    $765,000

    • 4 Beds
    • 3 Baths
    • 2,128 Sq Ft

    4825 Madison Canning House Rd, Madison, MD 21648

    A must-see if you're looking for Eastern Shore Waterfront charm! Beautiful waterfront with expansive sunrise views of Madison Bay! Recently renovated primary residence or weekend getaway 15 minutes off of Route 50 outside Cambridge. Four bedroom, three bathroom two-story on 2.2 Acres. 800 ft of wrap around rip rap, pier with deep water docking for 2 to 3 boats. Detached shed/ one car garage for

    Agent Photo

    Wayne Phillips

    Coastal Life Realty Group LLC

    (410) 618-4673

    4825 Madison Canning House Rd, Madison, MD 21648
  • /6

    $500,000

    • Land
    • 1.41 Acres
    • $354,610 per Acre

    0 High St, Cambridge, MD 21613

    Prime Ground-Floor Development Opportunity at One of the City’s Highest-Traffic IntersectionsRare opportunity to own and develop what many consider the best and most visible intersection in the city—located at the corner of Washington Street and High Street, the first major intersection entering town from the country. The property is bordered on three sides, including a city-owned paper

    Agent Photo

    Anthony Golden

    Berkshire Hathaway HomeServices PenFed Realty

    (410) 807-3843

    0 High St, Cambridge, MD 21613
  • /55

    $899,900

    • 4 Beds
    • 3 Baths
    • 4,752 Sq Ft

    2613 Hoopers Island Rd, Fishing Creek, MD 21634

    Enjoy the beauty and serenity of Hoopers Island from this spacious water-view retreat in Fishing Creek, Maryland. This stunning home offers over 4,500 square feet of beautifully finished living space, featuring 4 bedrooms and 3 full bathrooms, including a convenient first-floor bedroom and full bath—perfect for guests or multigenerational living.Set on 4.9 acres, the home showcases

    Agent Photo

    Charlene Spence

    The Spence Realty Group

    (410) 512-6396

    2613 Hoopers Island Rd, Fishing Creek, MD 21634
  • /18

    $55,000

    • Land
    • 3.53 Acres
    • $15,581 per Acre

    5229 Heron Rd, Cambridge, MD 21613

    Build your dream home on this scenic 3.53-acre wooded lot in the exclusive Heron Harbor community, nestled along Webbs Creek, which feeds into the Choptank River. Surrounded by water and nature, this peaceful setting offers access to a community pier on navigable water—perfect for kayaking, boating, and enjoying fresh Eastern Shore crabs. HOA fees include dock maintenance and BIP septic hook-up

    Agent Photo

    Nicole Schreibstein Abbott

    Northrop Realty

    (410) 346-3515

    5229 Heron Rd, Cambridge, MD 21613
  • /43

    $390,000

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

    5926 Mount Holly Rd, East New Market, MD 21631

    Back on market at no fault of seller and they are motivated! Big tickets items are done and all that's left is to move in and enjoy the warm days ahead! 4BR/3BA Rancher with plenty of room for everyone! Wow, two primary suites! This meticulously cared-for rancher set on a private, peaceful 1-acre lot in East New Market is a one-of-a-kind gem! Offering the perfect blend of rural serenity and

    Agent Photo

    Whitney Westover

    Century 21 Emerald

    (410) 936-5364

    5926 Mount Holly Rd, East New Market, MD 21631
  • /67

    $345,000

    • 4 Beds
    • 3 Baths
    • 3,210 Sq Ft

    31 Main St, East New Market, MD 21631

    31 Main Street – East New Market, MarylandStep back in time and experience the charm of this 1920 Victorian-style home located in the HistoricDistrict of the Town of East New Market. This home showcases many of its original architectural detailsand period character while offering several important modern updates. Over the years, the property hasseen numerous improvements,

    Gary Lucks

    Keller Williams Realty

    (410) 623-7595

    31 Main St, East New Market, MD 21631
  • /39

    $1,250,000

    • 5 Beds
    • 4.5 Baths
    • 3,849 Sq Ft

    2208 Horns Point Rd, Cambridge, MD 21613

    Stunning Classic Greek Revival Architecture Home on Jenkins Creek, just minutes from Downtown Cambridge. Enter the extended blacktop lane off Horns Point Rd until you arrive at the circular drive of this beautifully appointed 5 Bedroom, 4 1/2 Bath, waterfront home with water views from almost every room. The home sits on an elevated 3.3+/- acres with approximately three miles of unobstructed

    Craig Linthicum Benson & Mangold, LLC

    2208 Horns Point Rd, Cambridge, MD 21613
  • /58

    $595,000

    • 3 Beds
    • 3 Baths
    • 1,996 Sq Ft

    3113 Bay View Dr, Church Creek, MD 21622

    ATTENTION: Stunning Coastal Retreat with Breathtaking Chesapeake Bay Views And Access Welcome to your dream escape on Maryland’s Eastern Shore—where tranquility, nature, and waterfront living come together in perfect harmony. This beautifully appointed 3-bedroom, 3-bath coastal home is ideally situated on a canal with direct access to the Chesapeake Bay, offering endless opportunities for

    Craig Linthicum Benson & Mangold, LLC

    3113 Bay View Dr, Church Creek, MD 21622
  • /27

    $229,900

    • Land
    • 1.82 Acres
    • $126,319 per Acre

    000 River View, East New Market, MD 21631

    Discover a rare opportunity to own a 1.82 acre homesite in the East Bay Shores at Wrights Creek community in Dorchester County, Maryland. Situated near the corner of an open field, this property offers beautiful open water views, while a natural tree buffer along the northern boundary provides added privacy and a peaceful backdrop. The lot provides an excellent opportunity to build a custom home

    Casey Kennedy Whitetail Properties Real Estate

    000 River View, East New Market, MD 21631
  • /107

    $9,900,000

    • 4 Beds
    • 3.5 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
  • /34

    $249,900

    • Land
    • 16.38 Acres
    • $15,256 per Acre

    0 Silver Goose Rd Unit Lot WP001, 7, Cambridge, MD 21613

    A very private setting with preparations in place for building a country home with a long driveway and views of neighboring farmland. Sellers have performed much of the heavy lifting with county septic and pond building permits. Stormwater management is in place with culverts and a gated driveway. Only a mile drive to a public boat launch to Chesapeake Bay tributary waters on Fishing Creek. A 50

    Mike Arajakis Whitetail Properties Real Estate

    0 Silver Goose Rd Unit Lot WP001, 7, Cambridge, MD 21613
  • /2

    $199,000

    • Land
    • 13.02 Acres
    • $15,284 per Acre

    0 Maple Dam Rd Unit 15924452, Cambridge, MD 21613

    13+/- acre parcel of land with multiple, potential development opportunities including commercial and residential mix. Currently in ag use. Call town to verify potential uses.

    Chuck Jr. Benson and Mangold

    0 Maple Dam Rd Unit 15924452, Cambridge, MD 21613
  • /22

    $259,000

    • 4 Beds
    • 2 Baths
    • 1,711 Sq Ft

    6540-1 Eldorado Rd, Federalsburg, MD 21632

    4 bed 2 bath 1 story. Rural area lot with large detached outbuilding-shop-garage. Some cosmetic updates needed.

    Jeff Powell Coldwell Banker Realty

    6540-1 Eldorado Rd, Federalsburg, MD 21632
  • /29

    $179,900

    • 1 Bed
    • 1 Bath
    • 658 Sq Ft

    2839 Lakesville Crapo Rd, Church Creek, MD 21622

    Hunters Haven! The perfect blend of recreation and opportunity with this 16-acre hunting property. Featuring a versatile large agricultural field, a blank canvas to make it your own, strategically plant food plots or the back right corner is an ideal location for a future impoundment to attract and sustain wildlife. This property has a little bit of everything for outdoor enthusiasts, offering

    Brett Schrader Taylor Properties

    2839 Lakesville Crapo Rd, Church Creek, MD 21622
  • /84

    $1,250,000

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

    5253 Ragged Point Rd, Cambridge, MD 21613

    !!Check this one out!! COMING SOON | 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

    Craig Linthicum Benson & Mangold, LLC

    5253 Ragged Point Rd, Cambridge, MD 21613
  • /61

    $875,000

    • 4 Beds
    • 4 Baths
    • 2,900 Sq Ft

    1308 Town Point Rd, Cambridge, MD 21613

    Classic Historic Tidewater Colonial with 525+/- feet on the banks of Fishing Creek overlooking the Little Choptank River with a short ride to the Chesapeake Bay. Close to some of the best fishing spots on the Bay. This Historic Tidewater Colonial w/two bedrooms, living room, den, family room, dining room, kitchen, scenic three season porch, utility room, and two car garage make the Bay and its

    Craig Linthicum Benson & Mangold, LLC

    1308 Town Point Rd, Cambridge, MD 21613
  • /61

    $1,480,000 Open Sat 12PM - 4PM

    • 4 Beds
    • 5 Baths
    • 4,512 Sq Ft

    5419 Ragged Point Rd, Cambridge, MD 21613

    Welcome to 5419 Ragged Point Road — Closer than you think to D.C., Baltimore, and Ocean City, a striking contemporary waterfront estate set on 11.88 private acres with an incredible 1,500 feet of frontage along serene Brooks Creek. Designed for those who appreciate the best of Eastern Shore living, this 4-bedroom, 2 full/3 half bath custom home, built in 2007, offers exceptional craftsmanship and

    Gwen Eskridge Coldwell Banker Chesapeake Real Estate Company

    5419 Ragged Point Rd, Cambridge, MD 21613
  • /88

    $499,000

    • 4 Beds
    • 2.5 Baths
    • 2,426 Sq Ft

    1911 Dailsville Rd, Cambridge, MD 21613

    Beautiful custom built rancher on a 2 acre lot. Just outside of the up and coming town of Cambridge MD. This home includes 4 bedrooms, 2.5 bathrooms and an open concept floorplan throughout. Two large living spaces inside, each with its own fireplace. 2-car attached garage leading to a large back patio, outdoor fireplace, and swimming pool. Fresh paint throughout. Close to Black Water Refuge,

    Jimmy Higgins Benson & Mangold, LLC

    1911 Dailsville Rd, Cambridge, MD 21613
  • /20

    $649,000

    • 5 Beds
    • 3 Baths
    • 3,230 Sq Ft

    5511 Casson Neck Rd, Cambridge, MD 21613

    Ready for your waterfront home just in time to start the season? Sellers did major renovations on this home during their short time that improved quality and function. This was not a flip. It was a planned forever home, but things changed course for the sellers . Previously, this home had a large fenced in area in the front of a home with an inground pool not in use. They had dug everything up

    HEATHER MORRIS Springer Realty Group

    5511 Casson Neck Rd, Cambridge, MD 21613
  • /38

    $337,500

    • 3 Beds
    • 2 Baths
    • 1,378 Sq Ft

    4163 Whiteleyville Rd, Hurlock, MD 21643

    Welcome to Back Landing Estates! This development is located between Preston and Hurlock within the Warwick School District. This spacious 3-bedroom, 2-bathroom home features a large family room and a kitchen with a hardwood floor that overlooks open farmland, along with a generous yard and deck. The sellers have made several updates to the home, including new LVP flooring, a roof (2025),

    Roger Boyce Chesapeake Real Estate Associates, LLC

    4163 Whiteleyville Rd, Hurlock, MD 21643
  • /15

    $119,000

    • Land
    • 2.4 Acres
    • $49,583 per Acre

    Waterfront Honga Riv Steamboat Wharf Rd, Fishing Creek, MD 21634

    Looking for an affordable, versatile waterfront parcel on the Honga River, here it is! Ample high ground for a camper, this property is ideal for the outdoor enthusiast and hunter as your own private getaway on Hoopers Island, Hoopersville. The Honga river is known for great diver duck hunting - redheads, canvasbacks, blue bills. Fish, hunt, crab right off your own property while taking in

    Leo Kuneman Meredith Fine Properties

    Waterfront Honga Riv Steamboat Wharf Rd, Fishing Creek, MD 21634
  • /90

    $1,600,000

    • 4 Beds
    • 4.5 Baths
    • 5,037 Sq Ft

    1252 Old Madison Rd, Madison, MD 21648

    **THIS OPPORTUNITY IS FOR THE COMBINED PURCHASE OF 1252 OLD MADISON RD, MADISON, MD 21648 - TAX ID 1016008176 AND 1250 OLD MADISION RD, MADISON, MD 21648 - 1016001406** End each day with sweeping sunsets over Madison Bay from this exceptional waterfront compound featuring 268 feet of protected shoreline and approximately 2.83 acres of combined privacy, perfectly positioned with an ideal east-west

    Barbara McCaffrey Redfin Corp

    1252 Old Madison Rd, Madison, MD 21648
  • /90

    $1,600,000

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft

    1250 Old Madison Rd, Madison, MD 21648

    ***THIS OPPORTUNITY INCLUDES THE COMBINE PURCHSE OF 1252 OLD MADISON RD, MADISON, MD AND 1250 OLD MADISION RD, MADISON, MD*** End each day with sweeping sunsets over Madison Bay from this exceptional waterfront compound featuring 268 feet of protected shoreline and approximately 2.83 acres of combined privacy, perfectly positioned with an ideal east-west orientation. Built in 2013, the

    Barbara McCaffrey Redfin Corp

    1250 Old Madison Rd, Madison, MD 21648
  • /19

    $345,000

    • 3 Beds
    • 2 Baths
    • 1,366 Sq Ft

    4133 Whiteleyville Rd, Hurlock, MD 21643

    Welcome to this charming 3-bedroom, 2-bathroom home in Hurlock, MD, offering the perfect blend of comfort and space on a generous 1.3-acre lot. A covered front porch provides a warm and inviting entry into the home, where you’ll find a functional layout designed for everyday living. The kitchen features a convenient breakfast bar and flows seamlessly into the dining area and living room, creating

    Pamela Price Berkshire Hathaway HomeServices PenFed Realty

    4133 Whiteleyville Rd, Hurlock, MD 21643
  • /93

    $1,199,000

    • Land
    • 233.1 Acres
    • $5,144 per Acre

    2373 Asquith Island Rd, Crapo, MD 21626

    Asquith Sika Slam is 233 acres of pure sika hunting joy. The property consists of approximately 1/4 upland woods with the remainder in marsh, along the river on the south end. There is a great driveway back into the property where you’ll find an already installed BAT septic system to a sand mound drain field. Great opportunity to have some of the best deer and waterfowl hunting around, with the

    Rob Freyer Charis Realty Group

    2373 Asquith Island Rd, Crapo, MD 21626
  • /27

    $500,000

    • 3 Beds
    • 2 Baths
    • 1,538 Sq Ft

    5256 Williamsburg Rd, Federalsburg, MD 21632

    Welcome to your dream cabin! This stunning log cabin and two car garage are situated on over 17 wooded acres. Large welcoming front porch with an equally large enclosed rear porch. Inside you will find several areas for seating and entertaining. Interior walls are also logs. Three bedrooms and 2 bathrooms.

    Elizabeth Tryon Coldwell Banker Realty

    5256 Williamsburg Rd, Federalsburg, MD 21632
  • /24

    $99,900

    • 3 Beds
    • 1 Bath
    • 808 Sq Ft

    2703 Toddville Rd, Toddville, MD 21672

    Affordable 3 Bedroom, 1 Bathroom home conveniently located in Toddville and includes the vacant land parcel across the street (Parcel 164). Previously rented as a hunting lodge, good for overnights, a casual retreat or full time living. Located across from Elijah’s General Store and near public boat ramps, Blackwater national wildlife refuge and marinas. Enjoy fishing, crabbing, hunting, biking,

    Leo Kuneman Meredith Fine Properties

    2703 Toddville Rd, Toddville, MD 21672
  • /58

    $384,900

    • 4 Beds
    • 2 Baths
    • 1,576 Sq Ft

    1511 Crocheron Rd, Toddville, MD 21672

    Nestled in the heart of Maryland’s Lower Eastern Shore, 1151 Crocheron Road in Toddvilleoffers a rare opportunity to own a property surrounded by nature, privacy, and authenticEastern Shore charm.This home is perfectly positioned for those seeking peace, space, and outdoor living. Withabundant wildlife, open surroundings, and a quiet rural setting, the property is

    Stephanie Faulkner Coldwell Banker Chesapeake Real Estate Company

    1511 Crocheron Rd, Toddville, MD 21672
  • /42

    $350,000

    • 3 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    6446 Suicide Bridge Rd, Hurlock, MD 21643

    Don't let the name fool you... you'll love living in this spacious cape cod filled with coastal charm! Nestled between fields and mature trees, you'll enjoy the peaceful and private setting. Enter into a large, eat-in kitchen with plenty of cabinets and a breakfast bar. Though the archway you'll find the living room featuring a stone fireplace with a pellet stove insert. Next up is the

    Donna Cohen Northrop Realty

    6446 Suicide Bridge Rd, Hurlock, MD 21643
  • /3

    $59,900

    • Land
    • 2.6 Acres
    • $23,038 per Acre

    5513 Galestown Newhart Mill Rd, Galestown, MD

    Galestown - nice lot in the country! Picture your new home here! Close to all mid shore locations -

    Valerie Brown Coldwell Banker Realty

    5513 Galestown Newhart Mill Rd, Galestown, MD
  • /24

    $229,900

    • Land
    • 1.82 Acres
    • $126,319 per Acre

    0 River View Rd Unit MDDO2011690, East New Market, MD 21631

    Discover a rare opportunity to own a 1.82± acre homesite in the East Bay Shores at Wright’s Creek community in Dorchester County, Maryland. Situated near the corner of an open field, this property offers beautiful open water views, while a natural tree buffer along the northern boundary provides added privacy and a peaceful backdrop.The lot provides an excellent opportunity to build a custom

    Casey Kennedy Whitetail Properties Real Estate, LLC

    0 River View Rd Unit MDDO2011690, East New Market, MD 21631
  • /19

    $950,000

    • Land
    • 106.23 Acres
    • $8,943 per Acre

    0 Indiantown Rd, Rhodesdale, MD 21659

    Located in Eastern Dorchester County, this 106± acre farm offers a mix of productive farmland and recreational opportunity. The property includes approximately 94 tillable acres with predominantly sandy loam soils, ideal for both grain production and vegetable or fruit cultivation. An additional 12± acres of timber surround a private field on the west side of Indiantown Road, adding recreational

    Benjamin Alder The Land Group

    0 Indiantown Rd, Rhodesdale, MD 21659
  • /30

    $359,900

    • 3 Beds
    • 2 Baths
    • 1,564 Sq Ft

    3755 Sunnyside Rd, East New Market, MD 21631

    It’s what’s on the inside that counts — and this charming home in the Warwick School District does not disappoint! Major updates have already been completed, giving you peace of mind while preserving the home’s original character. The entire second floor was taken down to the studs and thoughtfully rebuilt with new drywall, HVAC, electric, lighting, windows, and a beautifully updated full bath.

    Valerie Brown Coldwell Banker Realty

    3755 Sunnyside Rd, East New Market, MD 21631
  • /39

    $189,000

    • 3 Beds
    • 2 Baths
    • 1,575 Sq Ft

    1123 Ball Park Rd, Fishing Creek, MD 21634

    Move-in ready 3BR/2BA expanded Farm home located tucked into the sprawling landscape, on a large lot, in Fishing Creek. Pull into the extra long driveway which leads to the rear yard, make your way to the covered front entry and step inside a home filled with natural light, recessed lighting, natural wood accents throughout which includes ceiling beams, barn doors, accent walls, and easy care

    Brooke Tephabock LPT Realty, LLC

    1123 Ball Park Rd, Fishing Creek, MD 21634
  • /80

    $799,000

    • 5 Beds
    • 3 Baths
    • 2,636 Sq Ft

    5210 Wilson Rd, Cambridge, MD 21613

    Private, Waterfront house on 8.31 acres off of Town Point Rd. This property has a huge dock with 5+ MLW, comes fully furnished and currently sleeps 15 people! There is a proven track record of Vacation Rental income that generated more the $50,000 per year. Also comes with an offshore blind and boat ramp on the property if you are looking for waterfowl hunting, fishing and crabbing! More pictures

    Henry Gibbons-Neff Meredith Fine Properties

    5210 Wilson Rd, Cambridge, MD 21613
  • /14

    $79,999

    • Land
    • 75 Acres
    • $1,067 per Acre

    Duck, Sika & Waterfo Muskrat Harbor, Crapo, MD 21626

    Price Reduced! Boat access only for duck, waterfowl and Sika deer hunting, great location. If you are looking for acreage to hunt Sika deer, ducks and waterfowl, here it is! Navigable water. Very private. Two parcels are included in this sale approximately 75+/- acres combined, priced to sell. Local public boat ramps nearby. Buyer due diligence regarding sdat acreage.

    Leo Kuneman Meredith Fine Properties

    Duck, Sika & Waterfo Muskrat Harbor, Crapo, MD 21626
  • /55

    $1,100,000

    • 3 Beds
    • 2 Baths
    • 2,484 Sq Ft

    5211 Heron Rd, Cambridge, MD 21613

    Enjoy peaceful waterfront living in this beautiful Cape Cod set on 5.5+/- acres along protected Webbs Creek/Fishing Creek, just minutes from the Choptank River. Designed for comfortable one-level living, the home offers 3 bedrooms, 2 baths, a private home office, dining room, and a spacious great room with vaulted ceilings and a corner stone gas fireplace. Expansive windows and doors open to an

    Alma Fitzgerald Long & Foster Real Estate, Inc.

    5211 Heron Rd, Cambridge, MD 21613
  • /27

    $1,800,000

    • Land
    • 3.5 Acres
    • $514,286 per Acre

    5200 Travelers Rest Rd, Cambridge, MD 21613

    Eastern Shore Waterfront Building Lot. Discover a rare opportunity to own one of the Eastern Shore’s beautiful waterfront lots. Located in the small subdivision of Camelot, this 3.5-acre building lot offers breathtaking sunset views and an exceptional setting to create your dream home. Tucked along Fishing Creek just off the Little Choptank River, the property provides peaceful water views,

    Lona Todd Taylor Properties

    5200 Travelers Rest Rd, Cambridge, MD 21613
  • /23

    $199,000

    • 3 Beds
    • 1 Bath
    • 1,652 Sq Ft

    1213 Horse Point Rd, Fishing Creek, MD 21634

    Looking for a fixer-upper with sweeping views of the Chesapeake Bay? This is your chance to own a special piece of Hoopers Island paradise. The property features a 3-bedroom home ready for renovation, along with two outbuildings offering excellent storage or workshop potential. Enjoy breathtaking sunsets over the Chesapeake Bay from the front of the property, while the rear backs to a peaceful

    Dan Shoemaker Eastern Shore Real Estate, LLC

    1213 Horse Point Rd, Fishing Creek, MD 21634
  • /103

    $1,995,000

    • 7 Beds
    • 7 Baths
    • 5,920 Sq Ft

    5202 Heron Rd, Cambridge, MD 21613

    Nestled on the private four-acre waterfront enclave of Three Creeks Point, this extraordinary estate offers breathtaking sunrises and sunsets over Fishing Creek with sweeping southerly views of Church Creek spanning more than 180 degrees. The primary residence features 5 bedrooms, 4.5 baths, and over 5,400 square feet of thoughtfully designed living space, complemented by an expansive

    Sharon Spedden Sharon Real Estate P.C.

    5202 Heron Rd, Cambridge, MD 21613

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