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Caroline County MD Homes for Sale

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  • /102

    $1,250,000

    $145K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,356 Sq Ft

    23296 Wilder Way, Denton, MD 21629

    Right out of HGTV! Custom Built in 2020, this 3,350+/- sq ft one-level home offers an abundance of amenities including high ceilings, 4 bedrooms, 3.5 Baths, large open floorplan with huge gourmet kitchen with quartz/ss appliances, separate pantry, family room with stacked stone gas fireplace. The Primary Bedroom is located at one end of the house and includes a large bath with double vanity,

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (410) 376-8486

    23296 Wilder Way, Denton, MD 21629
  • /38

    $479,000

    • 4 Beds
    • 2.5 Baths
    • 2,747 Sq Ft

    8605 Hickory Place, Denton, MD 21629

    Beautiful Colonial Farmhouse nestled on a wooded lot at the end of a cul-de-sac private lane. This 4 bedroom, 2.5 bath home has been meticulously maintained and features a traditional floor plan with a large kitchen/breakfast area, large family room with vaulted ceilings and a gas fireplace, separate dining room, living room/office. Second floor includes a primary suite with large bathroom with a

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (443) 998-8840

    8605 Hickory Place, Denton, MD 21629
  • /28

    $595,000

    • 3 Beds
    • 3.5 Baths
    • 3,276 Sq Ft

    23730 Henry Rd, Ridgely, MD 21660

    Beautiful Craftsman Cape Cod on quiet country road in Caroline County. This 3,200 sq ft home was built in 2023 and offers an open floor plan with all the amenities...large family room with vaulted ceilings, private office, large kitchen with white cabinets, farm sink, SS appliances, separate butler's pantry, and separate laundry room, first floor primary with walk-in closet, high-end primary

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (410) 406-6991

    23730 Henry Rd, Ridgely, MD 21660
  • /9

    $125,000

    • Land
    • 2.54 Acres
    • $49,213 per Acre

    0 Burnt Mill Rd Unit MDCM2005298, Ridgely, MD 21660

    Welcome to the Oasis neighborhood, a serene and picturesque enclave nestled in the charming town of Ridgely, MD. This prestigious 2.5-acre wooded lot on Burnt Mill Road presents a unique opportunity to craft your dream home amidst nature's splendor. With its perc approval, this lot is primed and ready for you to bring your architectural vision to life. As you enter the Oasis, you're greeted by a

    Agent Photo

    Gretchen Wichlinski

    Compass

    (667) 297-6243

    0 Burnt Mill Rd Unit MDCM2005298, Ridgely, MD 21660
  • /14

    $124,900

    $55K PRICE DROP
    • Land
    • 10.39 Acres
    • $12,021 per Acre

    PARCEL 91 Cool Spring Rd, Marydel, MD 21649

    Ready for you to build your new home! This beautiful lot is already perc approved for a 3-bedroom home. A barnominium is permitted to be built on this property and would be wonderful on this location. The woods are a great habitat for deer and turkey and other wildlife. This lovely lot is all ready for the new owner to apply for home construction as the buyer has had the survey completed with the

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    (410) 650-6268

    PARCEL 91 Cool Spring Rd, Marydel, MD 21649
  • /21

    $199,000

    $16K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,371 Sq Ft

    209 Reliance Ave, Federalsburg, MD 21632

    Charming home situated on approximately half an acre, offering a solid foundation and plenty of potential. This property features 2 bedrooms and 1 full bathrooms, along with a spacious bonus room that can serve as a home office, guest space, or additional living area. The home includes a dedicated laundry area and an eat-in kitchen, perfect for casual dining. With “great bones,” this property is

    Agent Photo

    Charlene Spence

    The Spence Realty Group

    (443) 241-6882

    209 Reliance Ave, Federalsburg, MD 21632
  • /8

    $125,000

    • Land
    • 2.4 Acres
    • $52,083 per Acre

    0 Burnt Mill Rd Unit MDCM2005300, Ridgely, MD 21660

    Welcome to the Oasis neighborhood, a serene and picturesque enclave nestled in the charming town of Ridgely, MD. This prestigious 2.4-acre wooded lot on Burnt Mill Road presents a unique opportunity to craft your dream home amidst nature's splendor. With its perc approval, this lot is primed and ready for you to bring your architectural vision to life. As you enter the Oasis, you're greeted by a

    Agent Photo

    Gretchen Wichlinski

    Compass

    (667) 868-0827

    0 Burnt Mill Rd Unit MDCM2005300, Ridgely, MD 21660
  • /87

    $1,550,000

    • 5 Beds
    • 4.5 Baths
    • 4,853 Sq Ft

    322 S 2nd St, Denton, MD 21629

    Wake up to sunrise on the Choptank River and wind down with some of the most stunning sunsets on the Eastern Shore — with Ospreys, Eagles, Herons, and an abundance of wildlife as your daily backdrop. This stunning 4,853 sq ft waterfront estate sits on 2.44 acres with 268 feet of private river frontage, putting you right on the water and just steps from the best of historic downtown Denton. Built

    Agent Photo

    Elizabeth Osborn

    Coldwell Banker Realty

    (410) 970-3374

    322 S 2nd St, Denton, MD 21629
  • /63

    $399,000

    $9K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft

    7392 Todds Wharf Rd, Preston, MD 21655

    This very comfortable rancher with a large high-quality above-ground pool with direct access to sunroom and into the home without getting feet dirty (yeah)! Roomy kitchen and open floor plan allows large gatherings to enjoy the roominess. Working wood-burning fireplace is great for use to heat home all winter or just on-call use when you want the ambiance. Convenient mudroom off garage with

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    (667) 843-7490

    7392 Todds Wharf Rd, Preston, MD 21655
  • /78

    $419,000

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,424 Sq Ft

    114 Lister Ln, Ridgely, MD 21660

    PRICE DROP! Sellers are very motivated. Beautiful colonial nestled in Lister Estates Community! Built in 2006, this detached home features 2,424 square feet above grade, with a new roof installed two years ago, plus a full unfinished basement ideal for storage or future expansion. The main level includes comfortable living spaces, a sunroom, large family room highlighted by a gas/propane

    Agent Photo

    Dustin Oldfather

    Compass

    (410) 705-7496

    114 Lister Ln, Ridgely, MD 21660
  • /8

    $125,000

    • Land
    • 2.31 Acres
    • $54,113 per Acre

    0 Burnt Mill Rd Unit MDCM2005294, Ridgely, MD 21660

    Welcome to the Oasis neighborhood, a serene and picturesque enclave nestled in the charming town of Ridgely, MD. This prestigious 2.3-acre wooded lot on Burnt Mill Road presents a unique opportunity to craft your dream home amidst nature's splendor. With its perc approval, this lot is primed and ready for you to bring your architectural vision to life. As you enter the Oasis, you're greeted by a

    Agent Photo

    Gretchen Wichlinski

    Compass

    (667) 282-1883

    0 Burnt Mill Rd Unit MDCM2005294, Ridgely, MD 21660
  • /41

    $585,000

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,643 Sq Ft

    24766 Tribbett Cir, Ridgely, MD 21660

    Welcome to this meticulously crafted 2023 contemporary farmhouse, perfectly positioned on a spacious .85-acre lot in the established community of Ashworth. Offering 3,168 square feet, 4 bedrooms, and 2.5 baths, this beautifully designed home blends timeless farmhouse charm with modern finishes and thoughtful upgrades throughout. The striking exterior showcases classic white siding, bold black

    Barbara McCaffrey Redfin Corp

    24766 Tribbett Cir, Ridgely, MD 21660
  • /27

    $369,900

    $5K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 2,268 Sq Ft

    803 Market St, Denton, MD 21629

    This inviting Victorian offers 4 bedrooms and 1.5 baths, that’s perfect for unwinding at the end of the day. Inside, natural light fills the main level, highlighting warm hardwood floors and comfortable living spaces. The living and dining areas connect seamlessly, creating an easy flow for everyday living. The kitchen features ample cabinet and counter space, stainless steel appliances, and a

    Steven Parsons Coldwell Banker Realty

    803 Market St, Denton, MD 21629
  • /66

    $374,990

    • 4 Beds
    • 2 Baths
    • 1,880 Sq Ft

    23116 Gilpin Point Rd, Preston, MD 21655

    Welcome to 23116 Gilpin Point Road in Preston, an updated Eastern Shore rancher offering the perfect blend of one floor living, privacy, history, and water oriented lifestyle. Beautifully situated on a spacious setting in the historic Gilpin Point area, this inviting home provides a peaceful country backdrop while still offering convenient access to nearby towns, commuter routes, and the gorgeous

    Angela Demattia Berkshire Hathaway HomeServices PenFed Realty

    23116 Gilpin Point Rd, Preston, MD 21655
  • /34

    $730,000

    New Construction $95K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    16960 Lentz Rd, Henderson, MD 21640

    Discover the charm of this newly constructed Cape Cod home, completed in 2026, where modern elegance meets timeless design. Nestled on a generous 19.16-acre lot, this detached residence offers a serene retreat while providing ample space for outdoor activities and future possibilities. Step inside to find a thoughtfully designed layout featuring three spacious bedrooms and two and a half

    Taylor Leaverton Benson & Mangold, LLC

    16960 Lentz Rd, Henderson, MD 21640
  • /50

    $419,000

    $10K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,382 Sq Ft

    225 S 2nd St, Denton, MD 21629

    Welcome to one of Denton's most charming historic homes, where timeless Victorian architecture, thoughtful updates, and small-town living come together beautifully. Situated on a picturesque corner lot in Denton's historic district, this lovingly maintained five-bedroom home offers more than 2,300 square feet of character-filled living space, abundant natural light, original architectural

    Barbara McCaffrey Redfin Corp

    225 S 2nd St, Denton, MD 21629
  • /2

    $79,900

    • Land
    • 9,147 Sq Ft
    • $380,476 per Acre

    6 N Central Ave, Ridgely, MD 21660

    Zoned commercial is this prime lot in the heart of Ridgely and next to the Town Office. Convenient street parking fronting the lot.

    Chuck Jr. Benson and Mangold

    6 N Central Ave, Ridgely, MD 21660
  • /2

    $260,000

    • 3 Beds
    • 2 Baths
    • 1,192 Sq Ft

    508 N 6th St, Denton, MD 21629

    Enjoy convenient one-level living on the north side of Denton, just a stone's throw from Bullock's and with easy access to Route 404 for commuting. Built in 2002, this charming 3-bedroom, 2-bath cottage offers a comfortable and functional layout. Enter from the side porch into a welcoming foyer that opens to the spacious living room, featuring a vaulted ceiling and cozy gas fireplace. Upgraded

    Traci Jordan Meredith Fine Properties

    508 N 6th St, Denton, MD 21629
  • /15

    $118,000

    • 3 Beds
    • 1.5 Baths
    • 1,664 Sq Ft

    501 Lincoln St, Denton, MD 21629

    Property is being sold As/ Is. Located on a corner lot. Owner has completed some work to the property, but additional work will be required. Please contact Denton Planning and Codes to verify remaining requirements to obtain an occupancy permit.

    Diane Wenk Wright Real Estate

    501 Lincoln St, Denton, MD 21629
  • /38

    $99,000

    • Land
    • 9,147 Sq Ft
    • $471,429 per Acre

    504 Central Ave, Ridgely, MD 21660

    UPDATE: The New Ridgely Comprehensive Plan draft will designate this lot for future commercial growth alongside the adjoining property—making this a strong investment opportunity. Call to request the documentation. This .21-acre vacant lot is ideally located in the heart of Ridgely. Currently zoned residential, yet future commercial allowance almost finalized - it offers access to public water

    Allie Harris Taylor Properties

    504 Central Ave, Ridgely, MD 21660
  • /2

    $260,000

    • 2 Beds
    • 1 Bath
    • 1,280 Sq Ft

    27944 Possum Hill Rd, Federalsburg, MD 21632

    Lovely two bedroom one bath rancher with spacious living room and dining room plus kitchen **1 car garage plus 30 x 30 storage area ** Heating is oil furnace 3 years old** Hot water tank is 3 years old **1.42 acres ** very flat usable lot

    Bev Langley Coldwell Banker Realty

    27944 Possum Hill Rd, Federalsburg, MD 21632
  • /85

    $799,000

    $76K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,149 Sq Ft

    3547 Prchal Rd, Preston, MD 21655

    **Don't Miss This Rare Opportunity**Pride of ownership shines throughout this beautifully appointed property set on over 4 serene acres, including approximately 2.5 wooded acres with private walking trails and an abundance of wildlife. Major 2025 home improvements including a brand new roof, siding and 10 Velux skylights, along with a new Bosch heat pump installed in 2024. This one-of-a-kind

    Amy Endzel Keller Williams Select Realtors of Annapolis

    3547 Prchal Rd, Preston, MD 21655
  • /18

    $325,000

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,302 Sq Ft

    25865 Brookwood Rd, Greensboro, MD 21639

    Sold as-is. Spacious 3 bedroom 2 full bathroom rancher located in sought-after Fox Grape neighborhood. Home is situated on private, wooded 1.23+/- acre lot. Included in the sale is an additional, adjacent .60+/- acre wooded lot for a total of 1.83+/- acres of land. Newer kitchen cabinets. Nice concrete patio, paved driveway and detached two car garage with additional workshop with power and

    Brian Petzold Benson & Mangold, LLC

    25865 Brookwood Rd, Greensboro, MD 21639
  • /12

    $82,500

    $53K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    103 Chambers St, Preston, MD 21655

    This Colonial home features timeless architecture and thoughtful design. The property offers solid construction and classic appeal, making it an excellent opportunity for discerning buyers. This distinctive property presents an outstanding opportunity for transformation and value creation. The established neighborhood setting combines small-town charm with practical accessibility to essential

    Pamela Geib Long & Foster Real Estate, Inc.

    103 Chambers St, Preston, MD 21655
  • /23

    $295,000

    • 3 Beds
    • 2 Baths
    • 1,646 Sq Ft

    130 Charlotte Ave, Federalsburg, MD 21632

    Welcome to 130 Charlotte Avenue in Federalsburg, Maryland—a well-appointed home offering three bedrooms, two full baths, and an attached two-car garage with a versatile bonus room above, ideal for a home office, gym, or guest space. Tucked away at the end of a quiet cul-de-sac, this property provides private outdoor enjoyment while remaining conveniently located for an easy commute to Seaford and

    FRANK LITTLE Berkshire Hathaway HomeServices PenFed Realty

    130 Charlotte Ave, Federalsburg, MD 21632
  • /2

    $390,000

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    25519 Linhard Ln, Greensboro, MD 21639

    Coming Soon! Enjoy the peace and privacy of country living on this lovely 4.68-acre property. This well-maintained one-level rancher features durable luxury vinyl plank (LVP) flooring and an upgraded kitchen with elegant quartz countertops, ample cabinetry.This home offers 3 bedrooms and 2 full baths, providing comfortable living space for family and guests. Exterior features include

    Jimmy White Long & Foster Real Estate, Inc.

    25519 Linhard Ln, Greensboro, MD 21639
  • /47

    $664,999

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

    4757 Long Swamp Rd, Federalsburg, MD 21632

    Welcome to 4757 Long Swamp Rd, a truly unique property in Federalsburg, MD, offering the perfect blend of equestrian facilities and comfortable country living on 7.04 acres. This well-maintained estate is ready for you and your horses, with no restrictions on property use and the added flexibility for the land to be subdivided. The grounds feature expansive pastures secured by electric fencing, a

    Billy Mister Keller Williams Realty

    4757 Long Swamp Rd, Federalsburg, MD 21632
  • /21

    $319,000

    $31K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,460 Sq Ft

    1308 Chesapeake Dr, Denton, MD 21629

    Well maintained ranch style home located in Cul -de -sac backing to trees. Three bedrooms ,two full baths , Eat in Kitchen, bright Living room plus den overlooking wooded back yard. Deck is ideal for that outdoor space to entertain. Two car garage offers space for storage in addition to parking. Sellers are offering allowance for new flooring. Make this your new home!

    Bonnie Johnson Keller Williams Realty

    1308 Chesapeake Dr, Denton, MD 21629
  • /14

    $120,000

    $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 640 Sq Ft

    26471 Three Bridges Rd, Federalsburg, MD 21632

    **Back Active at no fault of the seller**Opportunity awaits at 26471 Three Bridges Rd in Federalsburg, MD! This partially remodeled 2-bedroom, 2-bath home is ready for your finishing touch. Inside, the property has been taken down to the framing and subflooring, giving you a true blank canvas to bring your vision to life—whether you’re an investor looking for your next project or a buyer ready to

    LEE MARLAND Keller Williams Realty

    26471 Three Bridges Rd, Federalsburg, MD 21632
  • /7

    $527,000

    Coming Soon
    • 4 Beds
    • 3.5 Baths
    • 2,942 Sq Ft

    8590 Briar Patch Dr, Denton, MD 21629

    Enjoy the space and privacy of this beautiful home situated on over 2 acres just outside of Denton. The main level features a formal dining room, a spacious primary suite with separate his-and-her closets, and a private bath with a walk-in shower. The kitchen opens to the family room, creating an inviting space for everyday living and entertaining.Custom window treatments enhance both the

    Barbara Blosser Long & Foster Real Estate, Inc.

    8590 Briar Patch Dr, Denton, MD 21629
  • /21

    $229,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    103 Riverwalk Terrace, Federalsburg, MD 21632

    Hurry before it’s gone! This is an opportunity to buy in the sold out community of Riverwalk Terrace. The owner stayed at the home a few times some of the appliances never used. Open floor plan 1365 square feet , 3 bedrooms and 2.5 baths easy living. Only 2 years young this unit feels like new, was never a rental barley lived in. also backs up to the woods the private side of the community.

    Kat Thompson Benson & Mangold, LLC.

    103 Riverwalk Terrace, Federalsburg, MD 21632
  • /28

    $400,000

    New Construction
    • 4 Beds
    • 2 Baths
    • 1,800 Sq Ft

    210 W 2nd St, Ridgely, MD 21660

    OPEN HOUSE SATURDAY 6/6 12-2 All that’s left to do? Move in and make it yours. Reach out directly about 2-1 buy down with the sellers preferred lender! Brand new. Zero honey-do list. Full peace of mind. Welcome to this newly constructed 4-bedroom, 2-bath home in Ridgely, where modern design meets small-town charm. If you’ve been waiting for that fresh-start feeling — this is it. Step inside to a

    Kenneth Jester Coldwell Banker Realty

    210 W 2nd St, Ridgely, MD 21660
  • /22

    $189,000

    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft

    107 Smith St, Federalsburg, MD 21632

    Move-In Ready & Beautifully Remodeled!This charming 3-bedroom, 1.5-bath home offers the perfect blend of comfort and convenience. Enjoy a spacious living room, separate dining area, and a dedicated laundry room for added functionality.The kitchen is designed for both everyday living and entertaining, featuring dual bar seating areas with open views to the living and dining spaces. One

    Dawn Hubbard Keller Williams Select Realtors of Cambridge

    107 Smith St, Federalsburg, MD 21632
  • /3

    $265,000

    • 2 Beds
    • 1 Bath
    • 1,092 Sq Ft

    10819 Greensboro Rd, Denton, MD 21629

    This home will be a Total Renovation in 2026. Consisting of 2 BR and 1 Bath. Situated on almost a half ac. Lovely back yard, and new Well.

    Barbara Beaudet Brenton Realty Group

    10819 Greensboro Rd, Denton, MD 21629
  • /29

    $319,000

    $20K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 2,017 Sq Ft

    211 Bloomingdale Ave, Federalsburg, MD 21632

    Welcome to 211 Bloomingdale Ave. This custom‐built Brick Williamsburg‐style colonial showcases true craftsmanship, featuring beautiful hardwood floors throughout, custom built‐ins, and detailed moldings. The spacious living room offers an inviting wood‐burning fireplace, while the large great room with its vaulted ceiling provides flexible living space and could easily be converted into a third

    Jana Meredith Meredith Fine Properties

    211 Bloomingdale Ave, Federalsburg, MD 21632
  • /8

    $239,900

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft

    205 Park Ave, Federalsburg, MD 21632

    **Construction has not yet began, please feel free to drive by the lot. Completion will be for this August 2026!!*** The photos provided in the MLS are for reference purposes only and are intended to reflect the style and quality of similar fixtures, finishes, and features. Actual materials, fixtures, finishes, and selections may vary based on builder availability and final specifications.

    Erene Katris Coldwell Banker Realty

    205 Park Ave, Federalsburg, MD 21632
  • /2

    $27,500

    • Land
    • 12,196 Sq Ft
    • $98,214 per Acre

    0 Charlotte Ave, Federalsburg, MD 21632

    Build your dream home in the heart of Federalsburg! This approximately 0.28-acre residential lot is located within town limits and is zoned R-1 Single Family Residential. Public water and public sewer are available, offering a great opportunity for new construction in an established community. Conveniently located near local parks, schools, shopping, dining, and major commuter routes. Whether

    Heather Brummell Keller Williams Realty

    0 Charlotte Ave, Federalsburg, MD 21632
  • /8

    $79,900

    • Land
    • 4.31 Acres
    • $18,538 per Acre

    Lot 1 E Sunset Ave, Greensboro, MD 21639

    Large wooded lot on the outside of town. Perc approved for a 2' mound system. Located at the corner of Sunset Ave and River Rds. 4.3 acres Some forest conservation area. Only four lots in this subdivision and only three lots available.

    Marcia Rostien Long & Foster Real Estate, Inc.

    Lot 1 E Sunset Ave, Greensboro, MD 21639
  • /12

    $575,000

    • Land
    • 61.88 Acres
    • $9,292 per Acre

    17619 Melville Rd, Henderson, MD 21640

    The Melville Rd Farm is located on the east side of Melville Road and is bordered to the north by Trunk Line Road. The property includes approximately 51± acres of tillable ground along with 11± acres of wooded areas primarily situated around drainage ditches, providing natural transitions and wildlife cover. Two transmission lines run through the center of the farm, offering access corridors and

    Benjamin Alder The Land Group

    17619 Melville Rd, Henderson, MD 21640
  • /6

    $375,000

    • Land
    • 5.3 Acres
    • $70,755 per Acre

    0 Bloomingdale Ave Unit MDCM2006762, Federalsburg, MD 21632

    5.3 acre site on Bloomingdale Avenue, Federalsburg. Situated next to Dollar General, across from ProvidentState Bank and very near Royal Farm Store and McDonalds. Contains 3 parcels sold as a package. Publicutilities to the property. Shared access with Dollar General. C1 Commercial zoning allows a wide variety ofuses including: office, general business and professional uses, banks,

    Florence Adams SVN |Miller Commercial Real Estate

    0 Bloomingdale Ave Unit MDCM2006762, Federalsburg, MD 21632

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