157

Caroline County MD Homes for Sale

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  • /19

    $79,900

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    27980 Ruritan Rd, Denton, MD 21629

    CALLING ALL INVESTORS! This property in Denton is the one you have been waiting for! This one will not last! This Property is being sold As-Is condition. Buyer is responsible for all certifications. Seller never occupied. Neither the seller or listing agent make any representation as to the accuracy of any information contained herein. Buyer must conduct their own due diligence, verification,

    Simran Dheer Tesla Realty Group, LLC

    27980 Ruritan Rd, Denton, MD 21629
  • /2

    $272,000

    $2K PRICE INCREASE
    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    325 Carter Ave, Denton, MD 21629

    Excellent cozy home just waiting for you in the town of Denton with the small town atmosphere and a lot of amenities. Affordably priced, close to shopping, easy commute to the Western Shore and close enough to Delaware and Maryland beaches. Come see today because this home will not last long.

    George Thompson Long & Foster Real Estate, Inc.

    325 Carter Ave, Denton, MD 21629
  • /11

    $269,900

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    11 9th St, Ridgely, MD 21660

    Step into this well kept 2 bedroom, 1 bath rancher and feel instantly at home. Enjoy your morning coffee or an afternoon barbeque on the back patio with a privacy fenced back yard. Recent updates include vinyl plank flooring (2024), New roof, new refrigerator, new light fixtures and a fully encapsulated crawl space with sump pump - french drain and dehumidifier. All that's needed is your touch of

    Diane Wenk Wright Real Estate

    11 9th St, Ridgely, MD 21660
  • /29

    $750,000

    • 3 Beds
    • 2 Baths
    • 4,580 Sq Ft

    14236 Drapers Mill Rd, Greensboro, MD 21639

    STOP, LOOK, and READ...this may be exactly the property you’ve been searching for!! RESIDENTIAL / COMMERCIAL OPPORTUNITY – Zoned C-2, this versatile multi-use property offers endless possibilities! Relocate your business, expand to a second location, or launch your next venture while enjoying the convenience of living and working side by side on this incredible 2+ acre property. This unique

    Karen Clark Clark & Co Realty, LLC

    14236 Drapers Mill Rd, Greensboro, MD 21639
  • /74

    $525,000

    • 3 Beds
    • 3 Baths
    • 3,088 Sq Ft

    22005 Main St, Hillsboro, MD 21641

    PLEASE NOTE that the Owner has listened to the current market, Price has been reduced to $525,000. It is a property of beautifully preserved quality on 3⁄4 of an acre in an urban setting. Most unusual! When compared to equivalent historic properties it is now very competitively priced! This fine, brick dwelling originating from the18th c. is situated in Hillsboro on Maryland's peaceful Eastern

    Nancy McGuire Maryland Heritage Properties

    22005 Main St, Hillsboro, MD 21641
  • /9

    $89,000

    • Land
    • 3.05 Acres
    • $29,180 per Acre

    10440 Burrsville Branch Rd, Denton, MD 21629

    3+ ACRES PARTLY WOODED AND BACKS TO FARMLAND. NOT LOCATED IN A COMMUNITY AND NO HOA. (PLAT REFLECTS 3.235 +- ACRES, WHILE SDAT REFELCTS 3.05+- ACRES) PROPERTY IS IMPROVED WITH A 2 STORY HOME THAT WAS BUILT IN 1900 . THIS IS A TEAR DOWN OR PERHAPS POSSIBLY A FIXER UPPER. ***** DO NOT ENTER RESIDENCE***** THERE IS ALSO AN EXISTING WELL AND SEPTIC ON THE PROPERTY. HOUSE, WELL AND SEPTIC ARE AS-IS

    Deborah Callahan Benson & Mangold, LLC

    10440 Burrsville Branch Rd, Denton, MD 21629
  • /41

    $269,900

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    311 Maple Ave, Federalsburg, MD 21632

    Coming Soon! Prepare to be impressed by this stunning, top-to-bottom transformation. This home has been thoughtfully expanded with a brand-new second floor featuring a private primary suite, a dedicated laundry room, and a total of 3 spacious bedrooms and 2 modern baths. The main level shines with all-new LVP flooring, a modern kitchen boasting sleek new cabinetry, granite countertops, and

    Valerie Brown Coldwell Banker Realty

    311 Maple Ave, Federalsburg, MD 21632
  • /30

    $299,900

    $20K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,791 Sq Ft

    309 N Main St, Greensboro, MD 21639

    This exquisite Colonial-style home, thoughtfully renovated in 2019, seamlessly blends classic charm with modern luxury. Spanning 1,791 square feet, this residence offers a warm and inviting atmosphere, perfect for creating lasting memories. Step inside to discover a beautifully designed interior featuring engineered luxury vinyl plank flooring that exudes elegance and durability. The heart of the

    Eddie Matthews Benson & Mangold, LLC

    309 N Main St, Greensboro, MD 21639
  • /44

    $595,000

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,568 Sq Ft

    12104 Holly Rd, Ridgely, MD 21660

    Bring your horses and enjoy beautiful, country living just minutes away from town! Conveniently located with easy access to everything the eastern shore has to offer. New kitchen, new bathrooms, and new floors makes this place truly turn-key. Sitting on just over five acres, there's plenty of room to make this place yours. Two spacious paddocks, small barn including two stalls, tack room, water,

    Keith Hensley TTR Sotheby's International Realty

    12104 Holly Rd, Ridgely, MD 21660
  • /2

    $23,000

    • Land
    • 6,098 Sq Ft
    • $164,286 per Acre

    12115 Lincoln St, Ridgely, MD 21660

    Lot in the town of Ridgely, check with the town/county about putting a new house on this lot. There was previously a house on this lot.

    Pamela Geib Long & Foster Real Estate, Inc.

    12115 Lincoln St, Ridgely, MD 21660
  • /2

    $215,000

    • 3 Beds
    • 1 Bath
    • 756 Sq Ft

    105 Lincoln St, Greensboro, MD 21639

    Tenant-occupied property offering an excellent investment opportunity with immediate rental income. Current lease in place through July 31st. Tenants have expressed interest in renewing and would prefer to stay, providing potential for continued occupancy. Property is well-maintained and conveniently located near local amenities, schools, and major routes.Please allow adequate notice for all

    emily conley Taylor Properties

    105 Lincoln St, Greensboro, MD 21639
  • /18

    $4,250,000

    • 3 Beds
    • 2.5 Baths

    10870 River Rd, Denton, MD 21629

    Productive Caroline County grain farm approximately 340 acres in 4 parcels with 270+/- tillable acres with 200+/- under pivot. Soil has been grid sampled and is well drained. Farm is improved with three large machine sheds, the potentially usable footprint of a pervious milking parlor and a 3 bedroom, 2.5 bath Rancher overlooking the Choptank River. No easements.

    Jim Corson Benson & Mangold, LLC

    10870 River Rd, Denton, MD 21629
  • /30

    $309,000

    • 4 Beds
    • 3.5 Baths
    • 2,640 Sq Ft

    1907 Blue Heron Dr, Denton, MD 21629

    Largest townhome in the area and the best deal! Almost 2700 square feet for only $117 a square foot! The biggest bang for your buck in the county! Highly sought after large townhome in the desirable community of Mallard Landing in Denton, featuring almost double the square footage, and a rear deck off of the kitchen. Multi-generational living has a full bedroom and bath, as well as a large family

    Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    1907 Blue Heron Dr, Denton, MD 21629
  • /12

    $1,300,000

    • Land
    • 92.9 Acres
    • $13,994 per Acre

    0 Liberty Rd, Federalsburg, MD 21632

    90± deeded acres located east of Federalsburg off Liberty Road. The farm is primarily comprised of tillable land with approximately 36± acres under center pivot irrigation. Soils consist primarily of Woodstown, Klej-Galloway complex, and Fallsington sandy loam soils, which are commonly used for grain and row crop production in the area. The property offers approximately one half mile of road

    Benjamin Alder The Land Group

    0 Liberty Rd, Federalsburg, MD 21632
  • /37

    $279,000

    • 2 Beds
    • 2 Baths
    • 1,104 Sq Ft

    2697 Choptank Main St, Preston, MD 21655

    Charming Renovated Home in Choptank, Preston MD. This home currently has a fresh coat of interior paint, new kitchen appliances. Luxury vinyl flooring installed in the Living Room. Updated bath vanities and many more updates. It is turn key and ready and waiting for you. Situated on a large double lot with mature landscaping. Don’t miss this beautifully completely renovated 2-bedroom, 2-bath home

    Darlene Wheatley Benson & Mangold, LLC

    2697 Choptank Main St, Preston, MD 21655
  • /10

    $42,999

    • Land
    • 10,454 Sq Ft
    • $179,162 per Acre

    0 Brooklyn Ave, Federalsburg, MD 21632

    Taylor McCartney VRA Realty

    0 Brooklyn Ave, Federalsburg, MD 21632
  • /42

    $549,900

    Open Sat 10AM - 12PM
    • 4 Beds
    • 2.5 Baths
    • 2,304 Sq Ft

    3720 Payne Rd, Preston, MD 21655

    Welcome to your private countryside retreat on over 18 acres in the heart of Caroline County. This charming farmhouse-style home offers 4 bedrooms and 2.5 baths with over 2,300 sq ft of living space, combining comfort and functionality in a peaceful rural setting. The property features a mix of open land and wooded acreage, including over 6 acres in Forest Conservation, providing both privacy and

    Heather Brummell Keller Williams Realty

    3720 Payne Rd, Preston, MD 21655
  • /5

    $269,900

    • Land
    • 14.71 Acres
    • $18,348 per Acre

    0 Trunk Rd Unit MDCM2007270, Henderson, MD 21640

    14.71± acre perc-approved parcel on Trunk Line Rd in Henderson, MD! This beautiful wooded lot offers a conventional perc approved for 4+ bedrooms and provides an excellent opportunity to build your dream home, private retreat, or future homestead. Property features approximately 466 feet of road frontage along Trunk Line Road and includes a designated sewage reserve area shown on recorded plat.

    Heather Branham The Parker Group

    0 Trunk Rd Unit MDCM2007270, Henderson, MD 21640
  • /2

    $301,990

    New Construction
    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft

    121 Hobbs St, Greensboro, MD 21639

    Come discover 121 Hobbs Street, a new home soon to be under construction in the quaint Kinnamon Meadows community of Greensboro, MD. The Helena is an inviting 1,460 square foot cottage-style ranch home that offers four bedrooms, two bathrooms, and a one-car garage. The long, welcoming foyer of this home allows for the three guest bedrooms and guest bathroom to be separate from the living areas of

    D.R. Horton Builder
    121 Hobbs St, Greensboro, MD 21639
  • /16

    $243,000

    $7K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,693 Sq Ft

    1204 Blue Heron Dr, Denton, MD 21629

    Come on in to explore this beautifully maintained 3-level home offering the perfect blend of modern convenince and comfortable living. This beauty features 3 spacious bedrooms and 2.5 baths, with an open floor plan that creates an inviting flow throughout the main living areas. The home has been thoughtfully updated with fresh paint, new appliances and more to ensure it's move-in ready for you.

    Carolyn A. Page Shore Results Realty

    1204 Blue Heron Dr, Denton, MD 21629
  • /36

    $289,000

    • 3 Beds
    • 1 Bath
    • 1,392 Sq Ft

    6101 Bethlehem Rd, Preston, MD 21655

    *Please note Mother Nature has blessed this house with baby birds at the entrance, Showings are put off till the 8th of May, this should give the little feather family time to move on. Searching for quiet and private yet close to everything home - you just found it! Three bedroom rancher sits on 1.37 acres overlooking farmland makes this a very special find. Very well maintained and updated house

    Kat Thompson Benson & Mangold, LLC.

    6101 Bethlehem Rd, Preston, MD 21655
  • /12

    $299,900

    • 3 Beds
    • 1 Bath
    • 1,024 Sq Ft

    5 7th St, Ridgely, MD 21660

    Don't wait to tour this wonderfully renovated home in the Greenridge community! Lots to love from top to bottom. Completely rehabbed with Hickory Vinyl Plank flooring throughout and all freshly painted. New stainless steel appliances in the spacious kitchen with center island and lots of cabinet and working space plus a full pantry. All new beautiful bathroom with rain shower head. A laundry room

    Marcia Rostien Long & Foster Real Estate, Inc.

    5 7th St, Ridgely, MD 21660
  • /39

    $399,900

    $20K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,159 Sq Ft

    25331 Adams Landing Rd, Denton, MD 21629

    2 Acre cleared lot. Great opportunity for a fixer upper. Home needs a fair amount of work but it has a great layout. Main level primary, office/den separate dining room. Additional main level bedroom and full bath on main level. Spacious living room with access to the large screened porch. Corner eat-in kitchen & main level laundry. Cash or 203(K).***The property is being sold in its current

    Lisa Whited Keller Williams Realty

    25331 Adams Landing Rd, Denton, MD 21629
  • /40

    $235,000

    $85K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,122 Sq Ft

    212 Main St, Preston, MD 21655

    Welcome to this spacious and beautifully maintained property nestled in the peaceful town of Preston. The main residence features 5 generously sized bedrooms and 3 full bathrooms, offering plenty of space for comfortable family living, guests, or multi-generational arrangements. At the heart of the home, you’ll find a large eat-in kitchen, perfect for gathering with family, hosting friends, or

    Ross Muir EXP Realty, LLC

    212 Main St, Preston, MD 21655
  • /41

    $385,000

    $4K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,138 Sq Ft

    1111 Trice Meadows Cir, Denton, MD 21629

    ****PRICE ADJUSTMENT****Discover your dream home in the highly sought-after Trice Meadows community! This delightful 4-bedroom, 2-bathroom detached single-family home perfectly combines comfort, style, and modern convenience. Its open and inviting floor plan is designed for both day-to-day living and entertaining, making it an ideal choice for families and social gatherings alike. Experience

    LaTanya Drayton United Real Estate Premier

    1111 Trice Meadows Cir, Denton, MD 21629
  • /2

    $298,990

    New Construction
    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft

    Helena Plan at Kinnamon Meadows, Greensboro, MD 21639

    The Helena is an inviting 1,460 square foot cottage-style ranch home that offers four bedrooms, two bathrooms, and a one-car garage. The long, welcoming foyer of this home allows for the three guest bedrooms and guest bathroom to be separate from the living areas of the home. The oversized great room with an abundance of natural light is open to the kitchen making an ideal space to entertain or

    D.R. Horton Builder
    103 Park Ave Unit 36203274, Greensboro, MD 21639
  • /36

    $430,000

    Open Sat 12PM - 2PM $15K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,492 Sq Ft

    1709 Cattail Commons Way, Denton, MD 21629

    Welcome to 1709 Cattail Commons Way, located in the highly desirable Savannah Overlook community in Denton, MD. This beautifully maintained 4-bedroom, 2.5-bath home offers a spacious open floor plan, modern upgrades, and move-in ready convenience—perfect for today’s buyer seeking comfort, functionality, and style. The main level features a bright and open layout ideal for both everyday living and

    Kaitlyn Collins Benson & Mangold, LLC

    1709 Cattail Commons Way, Denton, MD 21629
  • /2

    $175,000

    • Land
    • 18.51 Acres
    • $9,454 per Acre

    0 Houston Branch Rd Unit MDCM2006924, Federalsburg, MD 21632

    These parcels are being sold as part of an estate. Three contiguous parcels with a total of 18.51 acres. Parcel 2 received Preliminary Perc Approval April 2015.

    Andrew Beaven Wright Real Estate

    0 Houston Branch Rd Unit MDCM2006924, Federalsburg, MD 21632
  • /20

    $175,000

    • Land
    • 6.3 Acres
    • $27,778 per Acre

    Parcel 15 Newton Rd, 4, Preston, MD 21655

    Discover the perfect blend of privacy and waterfront living with this 6.3-acre parcel on Newton Rd in Denton, MD. This beautiful wooded lot offers a serene setting with direct water views, making it ideal for building your dream home or a peaceful weekend retreat. The property is already perc-approved, saving you time and bringing you one step closer to construction. Enjoy nature, abundant

    Brent Starling Blackwell Real Estate, LLC

    Parcel 15 Newton Rd, 4, Preston, MD 21655
  • /23

    $310,000

    $49K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,922 Sq Ft

    5026 Bethlehem Rd, Preston, MD 21655

    MAJOR PRICE IMPROVEMENT!!! Totally renovated colonial offering nearly 2,000 sq ft of living space on a spacious 1/3-acre corner lot. Featuring 3, possibly 4 generous bedrooms and 2 full baths, this property showcases luxury vinyl plank flooring throughout. Enjoy privacy rear fencing and a large backyard—perfect for outdoor living. Ideal for a growing family and conveniently located close to

    Linda Moore Long & Foster Real Estate, Inc.

    5026 Bethlehem Rd, Preston, MD 21655
  • /44

    $419,000

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    11231 River Rd, Ridgely, MD 21660

    Looking for a nice House, Private & Lots of Land to Roam??? THIS Is IT!!!! Home features 3 Bedrooms, 2 Full Baths, Large Kitchen/Dining Combo With Lots of Storage- Updated Granite Countertops and Newer appliances. Spacious Family Room with FIreplace. Glassed in Sunroom for Entertaining! Garage with finished space for possible office with Running water & Electric. Garage also feauteres a second

    Kathleen Brenton Brenton Realty Group

    11231 River Rd, Ridgely, MD 21660
  • /27

    $250,000

    • 3 Beds
    • 2 Baths
    • 1,311 Sq Ft

    25910 Fox Grape Rd, Greensboro, MD 21639

    Quiet living in Fox Grape Farms. Whether you are downsizing or just starting out, this home offers one-level living with 3 bedrooms, 2 full baths and an open living room that flows into the dining area. Situated on a 0.60 +/- parcel, the property also features two (2) storage sheds. Located approximately 7 miles from Denton, MD, 11 miles from Tuckahoe State Park and 16 miles from the Harrington

    John Fifer Brokers Realty Group, LLC

    25910 Fox Grape Rd, Greensboro, MD 21639
  • /111

    $339,000

    • 3 Beds
    • 3 Baths
    • 2,030 Sq Ft

    13023 Mason Branch Rd, Ridgely, MD 21660

    Beautifully updated rancher offering approximately 2,000+ square feet on over an acre of land. This spacious home features 3 bedrooms, 3 full bathrooms, and 3 versatile bonus rooms ideal for a home office, gym, guest space, hobby room, or playroom. The interior has been thoughtfully renovated with modern updates throughout while maintaining a comfortable, functional layout. Outside, the property

    Jimmy Higgins Benson & Mangold, LLC

    13023 Mason Branch Rd, Ridgely, MD 21660
  • /19

    $415,000

    New Construction Coming Soon
    • 4 Beds
    • 2 Baths
    • 1,628 Sq Ft

    5 Sunrise Ave, Ridgely, MD 21660

    Pictured is Model- Colors, materials, and finishes are subject to change New Construction Home built by the reputable Lomaxx Custom Homes! The final home in Sunrise Village, this is your opportunity to get in early and make your personal selections. This one story home will offer 4 bedrooms, 2 full bathrooms and an open concept layout with stylish and on trend finishes throughout. Home to be

    Amy Betts Coldwell Banker Realty

    5 Sunrise Ave, Ridgely, MD 21660
  • /28

    $239,900

    $10K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,080 Sq Ft

    6413 Reliance Rd, Federalsburg, MD 21632

    Nice 3 bedroom 1 bath Rancher with garage in quiet country setting. This one will not last long!!

    Blaine Williamson McClain-Williamson Realty, LLC

    6413 Reliance Rd, Federalsburg, MD 21632
  • /48

    $319,500

    $36K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 708 Sq Ft

    13306 Greensboro Rd, Greensboro, MD 21639

    Stunning waterfront renovation on the Choptank River—completely redone inside and out in 2025! This beautifully updated 2-bedroom, 1.5-bath home offers approximately 800± square feet of thoughtfully designed living space. Completely remodeled from top to bottom, the residence showcases modern design and high-end finishes throughout. Updates include all-new walls, bathrooms, appliances, kitchen

    Lisa Magnus Clark & Co Realty, LLC

    13306 Greensboro Rd, Greensboro, MD 21639
  • /2

    $55,000

    • Land
    • 4.17 Acres
    • $13,189 per Acre

    E/S MD RT480 Unknown, Hillsboro, MD 21641

    Seller is waiting for perk results from Caroline county health department

    Diane Wenk Wright Real Estate

    E/S MD RT480 Unknown, Hillsboro, MD 21641

Showing Results 121 - 157, Page 4 of 4

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