15,720

Caroline County, MD Homes

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  • /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
  • /10

    Starting at $1,165 Per Month

    • 1 - 3 Beds

    502 Sunset Blvd, Ridgely, MD 21660

    Welcome to Sunset Hargraves Ridgely, where newly renovated affordable apartment homes meet the charm of Maryland’s Eastern Shore. Located in the heart of Ridgely, our spacious 1, 2, and 3-bedroom apartments feature brand-new kitchens, energy-efficient appliances, luxury vinyl plank flooring, new windows, and more. Community-wide upgrades include new roofing, gutters, and refreshed breezeways,

    Sunset Hargraves Ridgely

    (410) 634-7485

    502 Sunset Blvd, Ridgely, MD 21660
  • /24

    $160,000

    Sold Apr 02, 2026

    315 Cool Spring Rd, Marydel, MD 21649

    • 3 Beds
    • 1.5 Baths
    • 1,524 Sq Ft
    • Built 1920

    Last Sold Summary

    • 5% Below List Price
    • $105/SF
    • 19 Days On Market

    Current Estimated Value $162,429

    Last Listing Agent John Fifer Brokers Realty Group, LLC

    315 Cool Spring Rd, Marydel, MD 21649
    • /6

      Not Listed For Sale

      3449 Jefferson Pond Rd, Federalsburg, MD 21632

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 2025
      3449 Jefferson Pond Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 39 Days On Market

  • /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
  • /2

    Starting at $670 Per Month

    • 1 - 4 Beds

    500 High St, Denton, MD 21629

    Riverview Gardens

    (443) 448-8909

    500 High St, Denton, MD 21629
  • /37

    $325,000

    Sold May 12, 2026

    11305 River Rd, Ridgely, MD 21660

    • 3 Beds
    • 1 Bath
    • 1,533 Sq Ft
    • Built 1972

    Last Sold Summary

    • 13% Below List Price
    • $212/SF
    • 87 Days On Market

    Current Estimated Value $326,800

    Last Listing Agent Pamela Geib Long & Foster Real Estate, Inc.

    11305 River Rd, Ridgely, MD 21660
    • /38

      Est $377,193

      Not Listed For Sale

      508 Teal Cir, Greensboro, MD 21639

      • 3 Beds
      • 2.5 Baths
      • 1,952 Sq Ft
      • Built 2004
      508 Teal Cir, Greensboro, MD 21639

      Last Sold Summary

      • 10 Days On Market

  • /102

    $1,250,000

    $145K PRICE DROP Under Contract
    • 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
  • /6

    $1,100 Per Month

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft
    • Condo for Rent

    107 W Central Ave, Federalsburg, MD 21632

    Property Id: 2106426This spacious one bedroom apartment has lots of updates and is ready to move in. The unit also comes with a washer and dryer for your convenience.

    (443) 298-2215

    107 W Central Ave, Federalsburg, MD 21632
  • /5

    $1,020,000

    Sold Sep 26, 2025

    0 River Rd Unit MDCM2006210, Ridgely, MD 21660

    • Land
    • 134.85 Acres
    • $7,564 per Acre

    Last Sold Summary

    • 9 Days On Market

    Last Listing Agent Nick Haiduk Thyme Real Estate Co LLC

    0 River Rd Unit MDCM2006210, Ridgely, MD 21660
    • /44

      Est $466,481

      Not Listed For Sale

      25276 Adams Landing Rd, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,616 Sq Ft
      • Built 2006
      25276 Adams Landing Rd, Denton, MD 21629

      Last Sold Summary

      • 9 Days On Market

  • /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
  • /17

    $1,595

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Condo for Rent

    12050 School St Unit 3, Ridgely, MD 21660

    UNDER NEW MANAGEMENT. Welcome to Azure Townhomes, conveniently located in the charming town of Ridgely. IN UNIT WASHER & DRYER INCLUDED. Newly renovated and freshly painted SUNNY townhomes located within the Caroline County Public School District! This beautifully maintained 3-bedroom, 1-bath townhome offers spacious living at an affordable price. Enjoy a bright and updated interior featuring

    12050 School St Unit 3, Ridgely, MD 21660
  • /80

    $710,000

    Sold Mar 20, 2026

    15184 Jarrell Rd, Goldsboro, MD 21636

    • 6 Beds
    • 4.5 Baths
    • 5,000 Sq Ft
    • Built 1995

    Last Sold Summary

    • $142/SF
    • 494 Days On Market

    Current Estimated Value $722,330

    Last Listing Agent Leslie Fulford Mann & Sons, Inc.

    15184 Jarrell Rd, Goldsboro, MD 21636
    • /13

      Est $315,457

      Not Listed For Sale

      9347 Double Hills Rd, Denton, MD 21629

      • 3 Beds
      • 1.5 Baths
      • 2,080 Sq Ft
      • Built 1900
      9347 Double Hills Rd, Denton, MD 21629

      Last Sold Summary

      • 16 Days On Market

  • /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
  • /2

    $1,450

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • Condo for Rent

    5 Maryland Ave Unit 5d, Ridgely, MD 21660

    5 Maryland Ave Unit 5d, Ridgely, MD 21660
  • /21

    $391,000

    Sold Oct 29, 2025

    11225 Shane Cir, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 2017

    Last Sold Summary

    • $261/SF
    • 4 Days On Market

    Current Estimated Value $382,563

    Last Listing Agent Kathleen Brenton Brenton Realty Group

    11225 Shane Cir, Ridgely, MD 21660
    • /15

      Est $315,342

      Not Listed For Sale

      8888 Harmony Rd, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,680 Sq Ft
      • Built 1910
      8888 Harmony Rd, Denton, MD 21629

      Last Sold Summary

      • 3 Days On Market

  • /63

    $1,500,000

    • 3 Beds
    • 3.5 Baths
    • 3,958 Sq Ft

    7347 Harmony Rd, Preston, MD 21655

    Income-producing poultry farm situated on approximately 38.17 acres in desirable Caroline County, featuring four state-of-the-art “Tier 3” tunnel poultry houses with a combined capacity of approximately 110,000 broiler chickens. Built in 1993, the four 40’ x 500’ houses are equipped with Rotem Platinum+ controllers, Shore Time computerized controls, alarm systems, recirculation cooling pads, 6”

    Agent Photo

    Damon Brockenberry

    Keller Williams Preferred Properties

    (667) 220-6254

    7347 Harmony Rd, Preston, MD 21655
  • /17

    $1,600

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,182 Sq Ft
    • House for Rent

    108 Parkland Rd, Greensboro, MD 21639

    This shared property at 108 Parkland Rd features 2 bedrooms and 1 bathroom within a total of 1,182 square feet. The owner occupies their separate bedroom and bathroom. He is a young male, first responder, and active military service member. The living room offers ample space for relaxation and is equipped with high-speed internet access. The bathroom includes a tub/shower combination for

    108 Parkland Rd, Greensboro, MD 21639
  • /32

    $227,500

    Sold Aug 20, 2025

    1303 Blue Heron Dr, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 1,816 Sq Ft
    • Built 2004

    Last Sold Summary

    • $125/SF
    • 27 Days On Market

    Current Estimated Value $228,684

    Last Listing Agent Justin Pokrywka Taylor Properties

    1303 Blue Heron Dr, Denton, MD 21629
    • /52

      Est $501,682

      Not Listed For Sale

      5569 Harmony Woods Dr, Preston, MD 21655

      • 4 Beds
      • 2.5 Baths
      • 2,909 Sq Ft
      • Built 2005
      5569 Harmony Woods Dr, Preston, MD 21655

      Last Sold Summary

      • 185 Days On Market

  • /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
  • /25

    $2,500

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft
    • House for Rent

    7 N 1st St, Denton, MD 21629

    Beautifully remodeled 3 bedroom, 2 full bath home with an additional 4th office/flex room available for rent. The bonus room does not have a closet or door, so it is ideal for a home office, nursery, hobby room, or extra storage.The main level features a covered front porch, a spacious living room with a closet, and an updated kitchen area with room for a dining table, folding station, or

    7 N 1st St, Denton, MD 21629
  • /8

    $78,000

    Sold Jun 16, 2026

    lot 4 River Rd, Greensboro, MD 21639

    • Land
    • 5.62 Acres
    • $13,879 per Acre

    Last Sold Summary

    • 13% Below List Price
    • 5 Days On Market

    Last Listing Agent Marcia Rostien Long & Foster Real Estate, Inc.

    lot 4 River Rd, Greensboro, MD 21639
    • /22

      Est $237,271

      Not Listed For Sale

      203 Bernard Ave, Federalsburg, MD 21632

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1972
      203 Bernard Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 31 Days On Market

  • /9

    $125,000

    Under Contract
    • 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
  • /2

    $1,100

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 100 Sq Ft
    • House for Rent

    200 Maple Ave, Greensboro, MD 21639

    Room for rent. Room is furnished at this time. If tenant wants to bring personal furniture I can clear out room.

    200 Maple Ave, Greensboro, MD 21639
  • /8

    $89,900

    Sold Jun 16, 2026

    lot 2 E Sunset Ave, Greensboro, MD 21639

    • Land
    • 5.64 Acres
    • $15,940 per Acre

    Last Sold Summary

    • 5 Days On Market

    Last Listing Agent Marcia Rostien Long & Foster Real Estate, Inc.

    lot 2 E Sunset Ave, Greensboro, MD 21639
    • /52

      Est $765,373

      Not Listed For Sale

      17435 Melville Rd, Henderson, MD 21640

      • 5 Beds
      • 4 Baths
      • 3,854 Sq Ft
      • Built 2000
      17435 Melville Rd, Henderson, MD 21640

      Last Sold Summary

      • 21 Days On Market

  • /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
  • /10

    $1,150 Per Month

    • 1 Bed
    • 1 Bath
    • 738 Sq Ft
    • House for Rent

    101 W Sunset Ave, Greensboro, MD 21639

    Cute one bedroom apt in the heart of downtown! Upstairs unit has all appliances including washer and dryer. Spacious kitchen with breakfast bar. Open living room to kitchen. Central air. Town water and sewer.

    Marcia Rostien Long & Foster Real Estate, Inc.

    101 W Sunset Ave, Greensboro, MD 21639
  • /7

    $240,000

    Sold Aug 29, 2025

    4539 Houston Branch Rd, Federalsburg, MD 21632

    • 2 Beds
    • 1 Bath
    • 736 Sq Ft
    • Built 1949

    Last Sold Summary

    • $326/SF
    • 0 Days On Market

    Current Estimated Value $247,667

    Last Listing Agent Barbara Nichols Results Realty Inc.

    4539 Houston Branch Rd, Federalsburg, MD 21632
    • /31

      Est $582,788

      Not Listed For Sale

      24131 Carrlyn Dr, Ridgely, MD 21660

      • 3 Beds
      • 2.5 Baths
      • 2,044 Sq Ft
      • Built 1973
      24131 Carrlyn Dr, Ridgely, MD 21660

      Last Sold Summary

      • 20 Days On Market

  • /68

    $349,500

    • 3 Beds
    • 2 Baths
    • 1,436 Sq Ft

    110 N School St, Greensboro, MD 21639

    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 of openness to go with the open floor plan of the living room/dining area/kitchen with an easy flow from one area to

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    (667) 281-0954

    110 N School St, Greensboro, MD 21639
  • /10

    $2,300 Per Month

    • 4 Beds
    • 3.5 Baths
    • Townhouse for Rent

    1901 Blue Heron Dr, Denton, MD 21629

    Spacious 4-bedroom, 3.5-bath home located in a desirable Denton community. This well-maintained property offers plenty of room for comfortable living in a quiet neighborhood while remaining close to schools, shopping, and major routes. Monthly Rent: $2,300, Security Deposit: $2,300, No pets, Minimum credit score: 650, Non-smoking property. Tenant responsible for all utilities. This is a great

    1901 Blue Heron Dr, Denton, MD 21629
  • /38

    $225,000

    Sold Sep 19, 2025

    12194 Knife Box Rd, Greensboro, MD 21639

    • 2 Beds
    • 2 Baths
    • 1,488 Sq Ft
    • Built 1900

    Last Sold Summary

    • $151/SF
    • 38 Days On Market

    Current Estimated Value $241,994

    Last Listing Agent Dustin Parker The Parker Group

    12194 Knife Box Rd, Greensboro, MD 21639
    • /15

      Est $343,341

      Not Listed For Sale

      11891 Central Ave, Ridgely, MD 21660

      • 3 Beds
      • 2 Baths
      • 1,638 Sq Ft
      • Built 1981
      11891 Central Ave, Ridgely, MD 21660

      Last Sold Summary

      • 26 Days On Market

Showing Results 1 - 40, Page 1 of 18

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