15,675

Caroline County, MD Homes

Section Image
    • 2 Greenridge Ave, Ridgely, MD 21660
      2 Greenridge Ave, Ridgely, MD 21660
      2 Greenridge Ave, Ridgely, MD 21660
      /12

      Est $347,233 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,560 Sq Ft

      2 Greenridge Ave, Ridgely, MD 21660

      2 Greenridge Ave, Ridgely, MD 21660
  • 10440 Burrsville Branch Rd, Denton, MD 21629
    10440 Burrsville Branch Rd, Denton, MD 21629
    10440 Burrsville Branch Rd, Denton, MD 21629
    /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
  • 306 Railroad Ave, Goldsboro, MD 21636
    306 Railroad Ave, Goldsboro, MD 21636
    306 Railroad Ave, Goldsboro, MD 21636
    /29

    $220,000 Sold Aug 07, 2025

    306 Railroad Ave, Goldsboro, MD 21636

    • 3 Beds
    • 1 Bath
    • 1,568 Sq Ft
    • Built 1900

    Last Sold Summary

    • $140/SF
    • 10 Days On Market

    Current Estimated Value $224,529

    Last Listing Agent Brett Schrader Taylor Properties

    306 Railroad Ave, Goldsboro, MD 21636
    • 1104 Osprey Ln, Denton, MD 21629
      1104 Osprey Ln, Denton, MD 21629
      1104 Osprey Ln, Denton, MD 21629
      /42

      Est $411,891 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,590 Sq Ft

      1104 Osprey Ln, Denton, MD 21629

      1104 Osprey Ln, Denton, MD 21629
  • 3871 Laurel Grove Rd, Federalsburg, MD 21632
    3871 Laurel Grove Rd, Federalsburg, MD 21632
    3871 Laurel Grove Rd, Federalsburg, MD 21632
    /70

    $380,000 Pending

    • 4 Beds
    • 2 Baths
    • 2,114 Sq Ft

    3871 Laurel Grove Rd, Federalsburg, MD 21632

    Great Opportunity to own a Farm! 20 Acres plus Pole building to store your farm equipment, 2-car garage with a recreation room on the second floor. Great for hunting and fishing or to admire the wildlife.In-ground swimming pool with private fencing. Four season room, separate dining room, breakfast nook,Pellet stove, Fireplace with gas insert.This 1890 home needs some TLC.Call to

    Dawn Shorter McClain-Williamson Realty, LLC

    3871 Laurel Grove Rd, Federalsburg, MD 21632
  • 202 Maryland Ave, Ridgely, MD 21660
    202 Maryland Ave, Ridgely, MD 21660
    202 Maryland Ave, Ridgely, MD 21660
    /18

    $300,000 Sold Nov 20, 2025

    202 Maryland Ave, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2000

    Last Sold Summary

    • $223/SF
    • 123 Days On Market

    Last Listing Agent Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    202 Maryland Ave, Ridgely, MD 21660
    • 9585 Legion Rd, Denton, MD 21629
      9585 Legion Rd, Denton, MD 21629
      9585 Legion Rd, Denton, MD 21629
      /25

      Est $339,848 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,291 Sq Ft

      9585 Legion Rd, Denton, MD 21629

      9585 Legion Rd, Denton, MD 21629
  • 12739 Greensboro Rd, Greensboro, MD 21639
    12739 Greensboro Rd, Greensboro, MD 21639
    12739 Greensboro Rd, Greensboro, MD 21639
    /28

    $305,000

    • 3 Beds
    • 2 Baths
    • 1,614 Sq Ft

    12739 Greensboro Rd, Greensboro, MD 21639

    Welcome home! You've got to come see this well maintained 3-bedroom, 2-bath home offering comfort, character, and charm. Sitting on just over one acre, this property blends peaceful living with everyday convenience, located only a short drive from grocery stores, restaurants, and is roughly 30 minutes from both Dover and Milford. Step inside to find hardwood floors that add warmth and charm to

    Amy Mullen Iron Valley Real Estate Ocean City

    12739 Greensboro Rd, Greensboro, MD 21639
  • 305 Morning Glory Dr, Denton, MD 21629
    305 Morning Glory Dr, Denton, MD 21629
    305 Morning Glory Dr, Denton, MD 21629
    /55

    $390,000 Sold Jun 20, 2025

    305 Morning Glory Dr, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,646 Sq Ft
    • Built 2021

    Last Sold Summary

    • $147/SF
    • 37 Days On Market

    Current Estimated Value $429,195

    Last Listing Agent Cornelia Fallon Coldwell Banker Waterman Realty

    305 Morning Glory Dr, Denton, MD 21629
    • 11401 Greensboro Rd, Denton, MD 21629
      11401 Greensboro Rd, Denton, MD 21629
      11401 Greensboro Rd, Denton, MD 21629
      /19

      Est $311,381 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,036 Sq Ft

      11401 Greensboro Rd, Denton, MD 21629

      11401 Greensboro Rd, Denton, MD 21629
  • 309 N Main St, Greensboro, MD 21639
    309 N Main St, Greensboro, MD 21639
    309 N Main St, Greensboro, MD 21639
    /36

    $319,900

    • 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
  • 6074 Newton Rd, Preston, MD 21655
    6074 Newton Rd, Preston, MD 21655
    6074 Newton Rd, Preston, MD 21655
    /64

    $565,000 Sold Oct 08, 2025

    6074 Newton Rd, Preston, MD 21655

    • 3 Beds
    • 2.5 Baths
    • 2,060 Sq Ft
    • Built 1993

    Last Sold Summary

    • $274/SF
    • 64 Days On Market

    Current Estimated Value $584,781

    Last Listing Agent James Bent Benson & Mangold, LLC

    6074 Newton Rd, Preston, MD 21655
    • 23209 Gilpin Point Rd, Preston, MD 21655
      23209 Gilpin Point Rd, Preston, MD 21655
      23209 Gilpin Point Rd, Preston, MD 21655
      /8

      Est $499,877 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,560 Sq Ft

      23209 Gilpin Point Rd, Preston, MD 21655

      23209 Gilpin Point Rd, Preston, MD 21655
  • 24712 Tribbett Cir, Ridgely, MD 21660
    24712 Tribbett Cir, Ridgely, MD 21660
    24712 Tribbett Cir, Ridgely, MD 21660
    /37

    $609,900

    • 4 Beds
    • 5 Baths
    • 3,491 Sq Ft

    24712 Tribbett Cir, Ridgely, MD 21660

    Welcome to 24712 Tribbett Circle — a beautifully appointed 2016-built home set on 2.43 pristine acres in one of Ridgely’s most desirable neighborhoods. This luxurious 4-bedroom, 4-bathroom property seamlessly blends timeless style with modern comfort, offering an exceptional living experience both inside and out. The main level is adorned with rich bamboo flooring, creating a warm and

    Chris Warren Long & Foster Real Estate, Inc.

    24712 Tribbett Cir, Ridgely, MD 21660
  • 201 S 2nd St, Denton, MD 21629
    201 S 2nd St, Denton, MD 21629
    201 S 2nd St, Denton, MD 21629
    /32

    $250,000 Sold Feb 26, 2025

    201 S 2nd St, Denton, MD 21629

    • 4 Beds
    • 2 Baths
    • 1,536 Sq Ft
    • Built 1885

    Last Sold Summary

    • $163/SF
    • 135 Days On Market

    Current Estimated Value $272,759

    Last Listing Agent Darlene Winegardner RE/MAX Executive

    201 S 2nd St, Denton, MD 21629
    • 1115 Market St, Denton, MD 21629
      1115 Market St, Denton, MD 21629
      1115 Market St, Denton, MD 21629
      /17

      Est $239,430 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 788 Sq Ft

      1115 Market St, Denton, MD 21629

      1115 Market St, Denton, MD 21629
  • 412 N Main St, Greensboro, MD 21639
    412 N Main St, Greensboro, MD 21639
    412 N Main St, Greensboro, MD 21639
    /43

    $375,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,860 Sq Ft

    412 N Main St, Greensboro, MD 21639

    Rare Find! This 3-bedroom, 2-bath renovated rancher offers the perfect blend of space and charm on a sprawling 0.73 acre in-town lot. Spanning over 1,860 sq. ft. of updated living space, you’ll love the openess of the crisp, white kitchen that flows into a living-dining area anchored by a cozy wood-burning fireplace, the versatile bonus room/office and the entertainment-ready basement with a

    Karen Clark Clark & Co Realty, LLC

    412 N Main St, Greensboro, MD 21639
  • 508 W Sunset Ave, Greensboro, MD 21639
    508 W Sunset Ave, Greensboro, MD 21639
    508 W Sunset Ave, Greensboro, MD 21639
    /18

    $250,000 Sold Oct 14, 2025

    508 W Sunset Ave, Greensboro, MD 21639

    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft
    • Built 1975

    Last Sold Summary

    • $223/SF
    • 8 Days On Market

    Current Estimated Value $253,478

    Last Listing Agent Erene Katris Coldwell Banker Realty

    508 W Sunset Ave, Greensboro, MD 21639
    • 7881 Dyer Rd, Denton, MD 21629
      7881 Dyer Rd, Denton, MD 21629
      7881 Dyer Rd, Denton, MD 21629
      /33

      Est $307,381 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,961 Sq Ft

      7881 Dyer Rd, Denton, MD 21629

      7881 Dyer Rd, Denton, MD 21629
  • 12115 Lincoln St, Ridgely, MD 21660
    12115 Lincoln St, Ridgely, MD 21660
    /2

    $23,000

    • Land
    • 0.14 Acre
    • $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
  • 128 Mill St, Greensboro, MD 21639
    128 Mill St, Greensboro, MD 21639
    128 Mill St, Greensboro, MD 21639
    /7

    $265,000 Sold Mar 05, 2025

    128 Mill St, Greensboro, MD 21639

    • 3 Beds
    • 1 Bath
    • 1,890 Sq Ft
    • Built 1981

    Last Sold Summary

    • $140/SF
    • 18 Days On Market

    Current Estimated Value $296,911

    Last Listing Agent Phill Whitby Long & Foster Real Estate, Inc.

    128 Mill St, Greensboro, MD 21639
    • 1146 Osprey Ln, Denton, MD 21629
      1146 Osprey Ln, Denton, MD 21629
      1146 Osprey Ln, Denton, MD 21629
      /61

      Est $431,828 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,082 Sq Ft

      1146 Osprey Ln, Denton, MD 21629

      1146 Osprey Ln, Denton, MD 21629
  • 24383 Robins Creek Rd, Preston, MD 21655
    24383 Robins Creek Rd, Preston, MD 21655
    24383 Robins Creek Rd, Preston, MD 21655
    /30

    $375,000

    • 4 Beds
    • 2 Baths
    • 1,568 Sq Ft

    24383 Robins Creek Rd, Preston, MD 21655

    VERY NICE 3-4 BEDROOM, 2 BATH HOME IN TWO JOHNS WATERFRONT COMMUNITY. BOAT LANDING APPROXIMATELY 1/4 MILE AWAY. LARGE LIVING ROOM, KITCHEN-DINING ROOM COMBO, PANELED WALLS ARE ALL PAINTED, MOSTLY WOOD FLOORS. LARGE DECK AT REAR OF HOUSE. PATIO AREA WITH A NICE FIRE PIT FOR EVENING ENJOYMENT. MORE PICTURES TO COME SOON. ONLY 40 MILES TO WESTERN SHORE, LESS THAN 60 MILES TO THE BEACH

    Ed Quidas Long & Foster Real Estate, Inc.

    24383 Robins Creek Rd, Preston, MD 21655
  • 27381 Greenwood Rd, Denton, MD 21629
    27381 Greenwood Rd, Denton, MD 21629
    27381 Greenwood Rd, Denton, MD 21629
    /21

    $309,000 Sold Nov 03, 2025

    27381 Greenwood Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,922 Sq Ft
    • Built 1900

    Last Sold Summary

    • $161/SF
    • 66 Days On Market

    Current Estimated Value $301,827

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

    27381 Greenwood Rd, Denton, MD 21629
    • 1612 Blue Heron Dr, Denton, MD 21629
      1612 Blue Heron Dr, Denton, MD 21629
      1612 Blue Heron Dr, Denton, MD 21629
      /30

      Est $274,717 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,244 Sq Ft

      1612 Blue Heron Dr, Denton, MD 21629

      1612 Blue Heron Dr, Denton, MD 21629
  • 311 Kerr Ave, Denton, MD 21629
    311 Kerr Ave, Denton, MD 21629
    311 Kerr Ave, Denton, MD 21629
    /22

    $359,900

    • 3 Beds
    • 2 Baths
    • 1,753 Sq Ft

    311 Kerr Ave, Denton, MD 21629

    Discover this beautifully updated 3-bedroom, 2-bath corner lot rancher in Denton, Maryland, offering style, comfort, and unbeatable convenience! This single-story gem features gorgeous bamboo flooring throughout, creating a warm and modern ambiance. The traditional floor plan gives the living room area with wood burning fireplace a perfect cozy space for relaxing. Step into the Eat in Kitchen

    Justin Damadio Iron Valley Real Estate Ocean City

    311 Kerr Ave, Denton, MD 21629
  • 115 Riverwalk Terrace, Federalsburg, MD 21632
    115 Riverwalk Terrace, Federalsburg, MD 21632
    115 Riverwalk Terrace, Federalsburg, MD 21632
    /28

    $219,990 Sold Mar 24, 2025

    115 Riverwalk Terrace, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 1,365 Sq Ft
    • Built 2024

    Last Sold Summary

    • $161/SF
    • 66 Days On Market

    Current Estimated Value $233,037

    Last Listing Agent Kathleen Cassidy D R Horton Realty of Virginia LLC

    115 Riverwalk Terrace, Federalsburg, MD 21632
    • 1606 Blue Heron Dr, Denton, MD 21629
      1606 Blue Heron Dr, Denton, MD 21629
      1606 Blue Heron Dr, Denton, MD 21629
      /38

      Est $282,715 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,268 Sq Ft

      1606 Blue Heron Dr, Denton, MD 21629

      1606 Blue Heron Dr, Denton, MD 21629
  • 0 Brooklyn Ave, Federalsburg, MD 21632
    0 Brooklyn Ave, Federalsburg, MD 21632
    0 Brooklyn Ave, Federalsburg, MD 21632
    /10

    $42,999

    • Land
    • 0.24 Acre
    • $179,162 per Acre

    0 Brooklyn Ave, Federalsburg, MD 21632

    Taylor McCartney VRA Realty

    0 Brooklyn Ave, Federalsburg, MD 21632
  • 208 Bloomingdale Ave, Federalsburg, MD 21632
    208 Bloomingdale Ave, Federalsburg, MD 21632
    208 Bloomingdale Ave, Federalsburg, MD 21632
    /99

    $420,000 Sold Aug 29, 2025

    208 Bloomingdale Ave, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 3,734 Sq Ft
    • Built 1930

    Last Sold Summary

    • $112/SF
    • 16 Days On Market

    Current Estimated Value $435,622

    Last Listing Agent Blaine Williamson McClain-Williamson Realty, LLC

    208 Bloomingdale Ave, Federalsburg, MD 21632
    • 26875 Barclay Rd, Marydel, MD 21649
      26875 Barclay Rd, Marydel, MD 21649
      26875 Barclay Rd, Marydel, MD 21649
      /38

      Est $241,671 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,404 Sq Ft

      26875 Barclay Rd, Marydel, MD 21649

      26875 Barclay Rd, Marydel, MD 21649
  • 2 N Main St, Greensboro, MD 21639
    2 N Main St, Greensboro, MD 21639
    2 N Main St, Greensboro, MD 21639
    /19

    $50,000

    • Land
    • 0.37 Acre
    • $135,135 per Acre

    2 N Main St, Greensboro, MD 21639

    Cleared and ready for your vision! This 1/3+ acre in-town parcel offers the perfect canvas for your new build. Buyer to perform all due diligence with the Town regarding development requirements, including costs for water and sewer allocation.

    Karen Clark Clark & Co Realty, LLC

    2 N Main St, Greensboro, MD 21639
  • 326 N Main St, Federalsburg, MD 21632
    326 N Main St, Federalsburg, MD 21632
    326 N Main St, Federalsburg, MD 21632
    /31

    $227,000 Sold Jun 09, 2025

    326 N Main St, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,592 Sq Ft
    • Built 1915

    Last Sold Summary

    • $143/SF
    • 188 Days On Market

    Current Estimated Value $240,957

    Last Listing Agent Billy Mister Keller Williams Realty

    326 N Main St, Federalsburg, MD 21632
    • 1614 Blue Heron Dr, Denton, MD 21629
      1614 Blue Heron Dr, Denton, MD 21629
      1614 Blue Heron Dr, Denton, MD 21629
      /28

      Est $296,267 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,244 Sq Ft

      1614 Blue Heron Dr, Denton, MD 21629

      1614 Blue Heron Dr, Denton, MD 21629
  • 106 S 6th St, Denton, MD 21629
    106 S 6th St, Denton, MD 21629
    106 S 6th St, Denton, MD 21629
    /9

    $159,000

    • 3 Beds
    • 2 Baths
    • 2,776 Sq Ft

    106 S 6th St, Denton, MD 21629

    Charming colonial in the heart of Denton, thoughtfully converted into a two-unit multifamily property. Nestled on a quiet street, this home offers flexible living options with spacious layouts, classic character, and excellent potential for rental income or multigenerational living. A wonderful opportunity to invest or reside in a peaceful in-town setting. Great investment property.

    Amy Betts Coldwell Banker Realty

    106 S 6th St, Denton, MD 21629
  • 6939 Reliance Rd, Federalsburg, MD 21632
    6939 Reliance Rd, Federalsburg, MD 21632
    6939 Reliance Rd, Federalsburg, MD 21632
    /53

    $320,000 Sold Apr 28, 2025

    6939 Reliance Rd, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • Built 1981

    Last Sold Summary

    • $205/SF
    • 132 Days On Market

    Current Estimated Value $326,872

    Last Listing Agent Sharon Fisher RE/MAX Advantage Realty

    6939 Reliance Rd, Federalsburg, MD 21632
    • 1212 Painted Fern Rd, Denton, MD 21629
      1212 Painted Fern Rd, Denton, MD 21629
      1212 Painted Fern Rd, Denton, MD 21629
      /35

      Est $413,829 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,492 Sq Ft

      1212 Painted Fern Rd, Denton, MD 21629

      1212 Painted Fern Rd, Denton, MD 21629
  • 707 W Sunset Ave, Greensboro, MD 21639
    707 W Sunset Ave, Greensboro, MD 21639
    707 W Sunset Ave, Greensboro, MD 21639
    /10

    $157,499

    • Land
    • 1.01 Acres
    • $155,940 per Acre

    707 W Sunset Ave, Greensboro, MD 21639

    Several individual parcels on Sunset, Cosden and Harold Streets. One parcel has a large 50' x 70' Morton style building, town water and sewer are available. The offering does seem to have some ownership of another parcel consisting of Cosden St. Any interested buyer should perform their own suitable level of due diligence.

    BRIAN MORRIS The Land Group

    707 W Sunset Ave, Greensboro, MD 21639
  • 21959 Main St, Hillsboro, MD 21641
    21959 Main St, Hillsboro, MD 21641
    21959 Main St, Hillsboro, MD 21641
    /28

    $285,000 Sold May 09, 2025

    21959 Main St, Hillsboro, MD 21641

    • 4 Beds
    • 2 Baths
    • 2,168 Sq Ft
    • Built 1885

    Last Sold Summary

    • $131/SF
    • 9 Days On Market

    Current Estimated Value $318,893

    Last Listing Agent Jimmy White Long & Foster Real Estate, Inc.

    21959 Main St, Hillsboro, MD 21641
    • 25 Greenridge Ave, Ridgely, MD 21660
      25 Greenridge Ave, Ridgely, MD 21660
      25 Greenridge Ave, Ridgely, MD 21660
      /13

      Est $283,256 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft

      25 Greenridge Ave, Ridgely, MD 21660

      25 Greenridge Ave, Ridgely, MD 21660

Showing Results 401 - 440, Page 11 of 18

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