146

Caroline County MD Homes for Sale

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  • /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

    23730 Henry Rd, Ridgely, MD 21660
  • /68

    $329,900

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,436 Sq Ft

    110 N School St, Greensboro, MD 21639

    Price to purchase has been lowered to help you afford top quality at a fantastic price. Come see this beautiful home. Pride of ownership is shown from top to bottom in this magnificent rancher! This custom-built home was completed in June 2025 and is like new. The owner took much pride in everything he installed/built and makes this home very desirable. The nine-foot (9') ceilings add the feeling

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    110 N School St, Greensboro, MD 21639
  • /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

    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

    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 has ramps at rear of home for accessibility for those not able to walk up steps very well. Roomy kitchen and open floor plan allows large gatherings to enjoy the roominess. Large counter seats 4 comfortably. Dining area for full-size table and chairs. Working stone wood-burning fireplace is great for use to heat home all winter or just on-call use when you want the

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    7392 Todds Wharf Rd, Preston, MD 21655
  • /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

    0 Burnt Mill Rd Unit MDCM2005294, 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.

    PARCEL 91 Cool Spring Rd, Marydel, MD 21649
  • /2

    $99,500

    • 2 Beds
    • 1 Bath
    • 904 Sq Ft

    4669 Gadow Rd, Preston, MD 21655

    This cottage is being sold in "As Is" condition and can be renovated into a beautiful home. Bring your ideas of how you can renovated it and make an offer.

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    4669 Gadow Rd, Preston, MD 21655
  • /41

    $579,900

    $15K 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
  • /49

    $315,000

    • 4 Beds
    • 2 Baths
    • 2,774 Sq Ft

    111 Maple Ave, Greensboro, MD 21639

    Step into the timeless charm of this beautifully maintained circa-1880 home, where historic elegance meets thoughtful modern updates. Offering over 2,774 square feet of living space, this exceptional residence features 4 spacious bedrooms, 2 full bathrooms, and an abundance of original architectural character that has been lovingly preserved while incorporating today's modern conveniences. From

    Barbara McCaffrey Redfin Corp

    111 Maple Ave, Greensboro, MD 21639
  • /28

    $169,000

    • Land
    • 13.8 Acres
    • $12,246 per Acre

    000 Burnt Mill Rd, Ridgely, MD 21660

    This private 13.80 acre hunting tract offers an outstanding opportunity to own a well-managed and affordable recreational property on Maryland's Eastern Shore. Accessed by a deeded right-of-way, the property provides the privacy and seclusion serious hunters appreciate while remaining conveniently located for quick trips to the woods. The tract is comprised of mature hardwood timber and is

    Mike Arajakis Whitetail Properties Real Estate

    000 Burnt Mill Rd, Ridgely, MD 21660
  • /73

    $790,000

    $49K PRICE DROP
    • Land
    • 87 Acres
    • $9,080 per Acre

    000 Knife Box Rd, Greensboro, MD 21639

    PRICE IMPROVEMENT!!Located just outside Greensboro in Caroline County, Maryland, this exceptional 87 acre property offers a rare combination of income-producing farmland, diverse wildlife habitat, scenic natural features, and a highly developed hunting setup. The property consists of approximately 50 acres of mature woodland and 37 acres of productive tillable acreage, creating an ideal blend of

    Mike Arajakis Whitetail Properties Real Estate

    000 Knife Box Rd, Greensboro, MD 21639
  • /30

    $52,000

    • Land
    • 5.2 Acres
    • $10,000 per Acre

    American Corner Rd, Denton, MD 21629

    5.20 Acres of Wooded Land for Hunting and Recreation on Paved Road in Caroline County, MdCash Price: $52,000Reservation Fee: $900 non-refundable reservation fee secures this property. Reservation fee will be counted toward purchase price or down payment.With your Purchase You Get:1. A Deed in Your Own Name2. 4. NO Closing Fees if you Close Directly In-House with

    Elegment Land Elegment.com

    American Corner Rd, Denton, MD 21629
  • /22

    $467,900

    • 3 Beds
    • 4 Baths
    • 2,713 Sq Ft

    202 N Central Ave, Ridgely, MD 21660

    Charming Victorian home in the heart of Ridgely, ideally situated on a picturesque, tree-shaded corner lot. This timeless property offers classic character, curb appeal, and a prime location close to local amenities. An expansive wraparound front porch sets the stage for this beautiful home, featuring a gracious entryway, stunning columned foyer, and gleaming hardwood floors that enhance its

    Marcia Rostien Long & Foster Real Estate, Inc.

    202 N Central Ave, Ridgely, MD 21660
  • /11

    $165,000

    • 2 Beds
    • 1 Bath
    • 737 Sq Ft

    23480 Brunkhorst Rd, Preston, MD 21655

    Perfect as a starter home or rental, this cozy bungalow is situated on half an acre in a rural setting just outside of Preston. With an updated bathroom, new appliances, new flooring, fresh paint and a recent roof this home is move in ready. Nice garden/storage shed and raised bed gardens. Approximately 15 minutes from Easton and 1 hour from MD/DE beaches. Call to schedule your showing today!

    Andrew Beaven Wright Real Estate

    23480 Brunkhorst Rd, Preston, MD 21655
  • /47

    $425,000

    • 3 Beds
    • 1.5 Baths
    • 1,356 Sq Ft

    21370 Skeleton Creek Rd, Preston, MD 21655

    Very rustic and private 3 bedroom, 1 and a 1/2 bath log cabin on 15 private wooded acres. There is a large building and a sun porch overlooking a stream running through the property. Excellent hunting property for whitetail deer and turkey!

    Henry Gibbons-Neff Meredith Fine Properties

    21370 Skeleton Creek Rd, Preston, MD 21655
  • /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
  • /32

    $599,000

    $26K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,834 Sq Ft

    28402 Liden School Rd, Denton, MD 21629

    This is the one! Approx. 16.77 acres with an owner built 3 bedroom home. One acre with home plus additional acreage. Some acreage is wooded with wild life including, but not limited to, rabbit, deer, and turkey. This home has magnificent kitchen with custom cabinetry and SS appliances, including a 5 burner stove and double wall oven. Pellet stove is included for those cool evenings and damp days.

    Michael Shipley Benson & Mangold, LLC.

    28402 Liden School Rd, Denton, MD 21629
  • /2

    $190,000

    $70K PRICE DROP
    • 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
  • /25

    $325,000

    Open Sun 11:30AM - 1PM
    • 4 Beds
    • 2 Baths
    • 1,539 Sq Ft

    306 Sunrise Ave, Ridgely, MD 21660

    Charming & Move-In Ready in Ridgely! This 4-bedroom, 2-full-bath home is priced to sell and ready for its next owner. New $25,000 roof with 50-year transferable warranty! Situated on a spacious corner lot in the friendly town of Ridgely, MD, the property includes 2 utility sheds for extra storage and plenty of parking with off-street spaces in both the front and rear, plus additional on-street

    Vincent De Lorenzo Samson Properties

    306 Sunrise Ave, Ridgely, MD 21660
  • /2

    $310,000

    Coming Soon
    • 4 Beds
    • 2 Baths
    • 2,759 Sq Ft

    105 S 5th Ave, Denton, MD 21629

    Welcome to 105 S 5th Avenue, where historic small-town charm meets the convenience of living right in the heart of Denton! Built circa 1900, this spacious 4-bedroom, 2-full-bath detached home offers the character of a classic Eastern Shore residence with plenty of room to make it your own. One of the most special features of this location is the true front-row seat to Denton's hometown

    Jerry Peele Keller Williams Realty

    105 S 5th Ave, Denton, MD 21629
  • /58

    $620,000

    Open Sun 2PM - 4PM
    • 4 Beds
    • 2.5 Baths
    • 2,704 Sq Ft

    16881 Heritage Hills Ln, Henderson, MD 21640

    Privacy, space, and endless possibilities — this 5.06-acre retreat offers the lifestyle you've been looking for. Tucked into a partially wooded setting at the end of a quiet drive, 16881 Heritage Hills Ln provides the perfect blend of seclusion, functionality, and room to grow. Best of all, there's no HOA, giving you the freedom to truly enjoy your property. Built in 2005, the home offers 2,704

    Kaitlyn Collins Benson & Mangold, LLC

    16881 Heritage Hills Ln, Henderson, MD 21640
  • /14

    $110,000

    $40K 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
  • /28

    $699,000

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    14540 Drapers Mill Rd, Goldsboro, MD 21636

    Searching for your own private oasis with endless possibilities? Welcome to a rare 16.29-acre offering made up of four separate parcels, thoughtfully improved and ready for whatever vision you bring. Whether you dream of a hobby farm, a multi-use homestead, or a private retreat, this property delivers space, versatility, and infrastructure you won’t find anywhere else. Across the acreage you’ll

    Amanda Morgan Brenton Realty Group

    14540 Drapers Mill Rd, Goldsboro, MD 21636
  • /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
  • /47

    $495,000

    Open Sun 2:30PM - 4:30PM $15K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,231 Sq Ft

    14631 Fox Chase Cir, Ridgely, MD 21660

    OPEN House this Sunday August 16, 2:30-4:30! Welcome home to your own private country paradise. Nestled on 2.43 peaceful acres, this beautifully renovated log cabin blends rustic charm with modern comfort. Designed to impress, the home features both a main-level primary suite and a spacious second-floor primary suite, offering exceptional flexibility for family or guests. Thoughtfully updated

    Rick Parreco RE/MAX Executive

    14631 Fox Chase Cir, Ridgely, MD 21660
  • /22

    $174,000

    $15K PRICE DROP
    • 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
  • /2

    $95,000

    • 3 Beds
    • 1.5 Baths
    • 1,408 Sq Ft

    310 E Central Ave, Federalsburg, MD 21632

    Excellent investment opportunity! Over 1/4 acre lot. Home needs TLC. Partial owner financing available. Call for more info. This deal will not last long. Grab it while you have the chance!

    Raphael Szendro R&R Executive Realty

    310 E Central Ave, Federalsburg, MD 21632
  • /29

    $299,000

    $40K 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
  • /30

    $270,000

    $10K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 864 Sq Ft

    504 Sunset Blvd, Ridgely, MD 21660

    ***Price Improvement *** This delightful 3-bedroom bungalow offers a perfect blend of comfort and community. Built in 1940, this home exudes character with its sturdy block construction and inviting layout. The cozy 864 sq. ft. interior is complemented by essential appliances, including a refrigerator, stove, washer, and dryer, making daily living a breeze. The generous half-acre lot provides

    Cheryl Knotts Chesapeake Real Estate Associates, LLC

    504 Sunset Blvd, Ridgely, MD 21660
  • /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
  • /7

    $127,000

    • Land
    • 4.14 Acres
    • $30,676 per Acre

    0 Burnt Mill Rd Unit MDCM2006400, Ridgely, MD 21660

    Discover the ideal blend of tranquil nature and prime location! 4.14 acres with mature trees, offering unparalleled privacy and peaceful country living in one of the area's most scenic subdivisions -- all just minutes away from Ridgely and Denton, and less than 1 mile from North Caroline High School.Build your dream home on this beautiful level building lot, providing an even terrain

    Stephan Strothe Washington Fine Properties, LLC

    0 Burnt Mill Rd Unit MDCM2006400, Ridgely, MD 21660
  • /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
  • /40

    $280,000

    $25K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 1,884 Sq Ft

    407 W Sunset Ave, Greensboro, MD 21639

    Charming 5BR detached home, located in a quiet neighborhood in Greensboro. Experience the great outdoors in your own backyard on a nearly 1/2 acre lot, adjacent to 140 acres of farmland. Enjoy the 'Sunset' from the 320 sf sunroom with sliding glass doors, or sit outside to watch the sunrise on the new 230 sf wooden front porch. Several updates include replacement windows, upgraded plumbing &

    Raphael Szendro R&R Executive Realty

    407 W Sunset Ave, Greensboro, MD 21639
  • /16

    $99,000

    • 3 Beds
    • 1.5 Baths
    • 1,100 Sq Ft

    101 S University Ave, Federalsburg, MD 21632

    OFFER DEADLINE IS SUNDAY 8/16/26 AT 5PM. AS IS! GREAT INVESTMENT PROPERTY! This charming 3-bedroom, 1-bathroom traditional home, built in 1944, offers a solid investment opportunity with its AS IS condition gives you a blank slate to modernize this home to fit your needs! The traditional floor plan maximizes space, creating a warm and inviting atmosphere perfect for comfortable living. With a

    Joni Barrow Coldwell Banker Realty

    101 S University Ave, Federalsburg, MD 21632
  • /2

    $499,999

    New Construction
    • 4 Beds
    • 2 Baths
    • 1,613 Sq Ft

    25660 Cherry Blossom Ln, Denton, MD 21629

    Beautiful to be built new construction on 1.8 acres just outside Denton. This home offers 4 bedrooms, 2 full baths, great open kitchen with island, pantry, separate laundry room, large family room plus dining area. The crawl space will be conditioned for total peace of mind. The garage is huge measuring 32x22 and will be fully insulated with R19 Batts insulation. There will be a slider leading to

    Bonnie Johnson Keller Williams Realty

    25660 Cherry Blossom Ln, Denton, MD 21629
  • /2

    $180,000

    $95K PRICE DROP
    • Land
    • 0 Sq Ft

    11920 Central Ave, Ridgely, MD 21660

    Huge Price Drop – Act Fast Before It’s Gone! (Serious Buyers Only)This exceptional property features over 16 acres of level land with frontage on three roads: Central Avenue, Henry Road, and Holly Plains Drive. Zoned R-1, it offers outstanding potential—perfect for holding, subdividing, or developing.Located just outside the Ridgely city limits and close to the town center, the property

    Sam Benkirane Proplocate Realty, LLC

    11920 Central Ave, Ridgely, MD 21660
  • /74

    $479,000

    • 3 Beds
    • 3 Baths
    • 2,506 Sq Ft

    104 Charlotte Ave, Federalsburg, MD 21632

    Custom Brick Rancher with 2500 sq ft of living space sitting on over half an acre just outside of downtown Federalsburg overlooking Chambers Park is waiting for you to come see to appreciate. Owners have done many improvements and upgrades to the property, but left some of it's timeless charm. New carpet has been installed on the porch, breakfast nook, and family room July 2026, new windows 2026,

    Shelby Roney Benson & Mangold, LLC

    104 Charlotte Ave, Federalsburg, MD 21632

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