15,671

Caroline County, MD Homes

Section Image
    • 205 N Main St, Greensboro, MD 21639
      205 N Main St, Greensboro, MD 21639
      205 N Main St, Greensboro, MD 21639
      /17

      Est $389,042 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 3,876 Sq Ft

      205 N Main St, Greensboro, MD 21639

      205 N Main St, Greensboro, MD 21639
  • 506 Park Ave, Ridgely, MD 21660
    506 Park Ave, Ridgely, MD 21660
    506 Park Ave, Ridgely, MD 21660
    /59

    $298,000

    • 2 Beds
    • 1 Bath
    • 1,528 Sq Ft

    506 Park Ave, Ridgely, MD 21660

    Welcome to this delightful 2-bedroom, 1-bath rancher nestled in the heart of Ridgely. Perfectly positioned on a spacious double lot, this home offers abundant outdoor space—ideal for gardening, entertaining, or future expansion. A brand-new roof adds peace of mind and long-term value. Step inside to discover a bright and functional layout featuring a sun-drenched sunroom, a cozy living room with

    Lisa Lynch Keller Williams Realty

    506 Park Ave, Ridgely, MD 21660
  • 21303 Dover Bridge Rd, Preston, MD 21655
    21303 Dover Bridge Rd, Preston, MD 21655
    21303 Dover Bridge Rd, Preston, MD 21655
    /39

    $350,000 Sold Dec 27, 2024

    21303 Dover Bridge Rd, Preston, MD 21655

    • 3 Beds
    • 3 Baths
    • 2,607 Sq Ft
    • Built 1998

    Last Sold Summary

    • $134/SF
    • 16 Days On Market

    Current Estimated Value $392,300

    Last Listing Agent Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    21303 Dover Bridge Rd, Preston, MD 21655
    • 8 Caroline Ave, Ridgely, MD 21660
      8 Caroline Ave, Ridgely, MD 21660
      8 Caroline Ave, Ridgely, MD 21660
      /32

      Est $379,563 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,264 Sq Ft

      8 Caroline Ave, Ridgely, MD 21660

      8 Caroline Ave, Ridgely, MD 21660
  • 536 Gay St, Denton, MD 21629
    536 Gay St, Denton, MD 21629
    536 Gay St, Denton, MD 21629
    /3

    $110,000 Pending

    • 3 Beds
    • 1 Bath
    • 1,032 Sq Ft

    536 Gay St, Denton, MD 21629

    Property will be sold in as/ is condition. General Commercial zoning.

    Diane Wenk Wright Real Estate

    536 Gay St, Denton, MD 21629
  • 6315 Harmony Rd, Preston, MD 21655
    6315 Harmony Rd, Preston, MD 21655
    6315 Harmony Rd, Preston, MD 21655
    /36

    $325,000 Sold Sep 26, 2025

    6315 Harmony Rd, Preston, MD 21655

    • 3 Beds
    • 3 Baths
    • 2,016 Sq Ft
    • Built 1994

    Last Sold Summary

    • $161/SF
    • 28 Days On Market

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    6315 Harmony Rd, Preston, MD 21655
    • 219 Briarwood Cir, Denton, MD 21629
      219 Briarwood Cir, Denton, MD 21629
      219 Briarwood Cir, Denton, MD 21629
      /48

      Est $315,612 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 2,088 Sq Ft

      219 Briarwood Cir, Denton, MD 21629

      219 Briarwood Cir, Denton, MD 21629
  • 28402 Liden School Rd, Denton, MD 21629
    28402 Liden School Rd, Denton, MD 21629
    28402 Liden School Rd, Denton, MD 21629
    /60

    $699,000

    • 3 Beds
    • 2 Baths

    28402 Liden School Rd, Denton, MD 21629

    Private serene living at its finest! This property has it all -- gorgeous rancher with 3 BR and 2 full baths; pantry in the kitchen, family room with pellet stove and brick fireplace that can burn wood; two large walk-in closets in primary bedroom; so much to mention here that you really must come see for yourself -- fresh air, peace and quiet, birds singing, wildlife, and more. Want horses; this

    Bonnie Duley Long & Foster Real Estate, Inc.

    28402 Liden School Rd, Denton, MD 21629
  • 25820 Dogwood Rd, Greensboro, MD 21639
    25820 Dogwood Rd, Greensboro, MD 21639
    25820 Dogwood Rd, Greensboro, MD 21639
    /59

    $385,000 Sold May 12, 2025

    25820 Dogwood Rd, Greensboro, MD 21639

    • 3 Beds
    • 2.5 Baths
    • 1,568 Sq Ft
    • Built 1979

    Last Sold Summary

    • $246/SF
    • 203 Days On Market

    Current Estimated Value $419,384

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

    25820 Dogwood Rd, Greensboro, MD 21639
    • 24461 Friendship Rd, Preston, MD 21655
      24461 Friendship Rd, Preston, MD 21655
      24461 Friendship Rd, Preston, MD 21655
      /60

      Est $805,155 Not Listed For Sale

      • 4 Beds
      • 5 Baths
      • 4,546 Sq Ft

      24461 Friendship Rd, Preston, MD 21655

      24461 Friendship Rd, Preston, MD 21655
  • 5585 Harmony Woods Dr, Preston, MD 21655
    5585 Harmony Woods Dr, Preston, MD 21655
    5585 Harmony Woods Dr, Preston, MD 21655
    /54

    $549,000

    • 4 Beds
    • 2.5 Baths
    • 3,442 Sq Ft

    5585 Harmony Woods Dr, Preston, MD 21655

    Set on a private, wooded 1.37± acre lot in Harmony Woods, this beautifully maintained home offers a warm, inviting layout with abundant natural light and thoughtful updates throughout. A welcoming front porch leads into the main level with hardwood floors, detailed trim work, and easy flow from the kitchen and breakfast area to the living room with a wood-burning fireplace. Full-view doors open

    Georgi Chauvin Benson & Mangold, LLC

    5585 Harmony Woods Dr, Preston, MD 21655
  • 28268 Bridgeville Rd, Federalsburg, MD 21632
    28268 Bridgeville Rd, Federalsburg, MD 21632
    28268 Bridgeville Rd, Federalsburg, MD 21632
    /42

    $1,550,000 Sold Jun 13, 2025

    28268 Bridgeville Rd, Federalsburg, MD 21632

    • 4 Beds
    • 2 Baths
    • 1,888 Sq Ft
    • Built 1900

    Last Sold Summary

    • $821/SF
    • 11 Days On Market

    Current Estimated Value $1,598,225

    Last Listing Agent Nick Campanaro The Land Group

    28268 Bridgeville Rd, Federalsburg, MD 21632
    • 408 Maple Ave, Ridgely, MD 21660
      408 Maple Ave, Ridgely, MD 21660
      408 Maple Ave, Ridgely, MD 21660
      /11

      Est $300,560 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft

      408 Maple Ave, Ridgely, MD 21660

      408 Maple Ave, Ridgely, MD 21660
  • 11279 Central Ave, Ridgely, MD 21660
    11279 Central Ave, Ridgely, MD 21660
    11279 Central Ave, Ridgely, MD 21660
    /50

    $260,000 Under Contract

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

    11279 Central Ave, Ridgely, MD 21660

    This well kept 3 bedroom 2 full bath home sits on a private 1.13 acre lot just outside of Ridgely. Spacious bedrooms, 2 good sized full bathrooms, tons of natural light & newer appliances! The detached garage is huge, offers additional covered parking & storage! Fully fenced in back yard that backs to woods & farmland! Full driveway is owned by the seller.

    Megan Rosendale Rosendale Realty

    11279 Central Ave, Ridgely, MD 21660
  • 25265 Smith Landing Rd, Denton, MD 21629
    25265 Smith Landing Rd, Denton, MD 21629
    25265 Smith Landing Rd, Denton, MD 21629
    /45

    $410,100 Sold Mar 18, 2025

    25265 Smith Landing Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1976

    Last Sold Summary

    • $342/SF
    • 335 Days On Market

    Current Estimated Value $439,515

    Last Listing Agent Brenda Fornos Taylor Properties

    25265 Smith Landing Rd, Denton, MD 21629
    • 411 N 6th St, Denton, MD 21629
      411 N 6th St, Denton, MD 21629
      411 N 6th St, Denton, MD 21629
      /20

      Est $243,200 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,364 Sq Ft

      411 N 6th St, Denton, MD 21629

      411 N 6th St, Denton, MD 21629
  • PARCEL 91 Cool Spring Rd, Marydel, MD 21649
    PARCEL 91 Cool Spring Rd, Marydel, MD 21649
    PARCEL 91 Cool Spring Rd, Marydel, MD 21649
    /14

    $149,900

    • Land
    • 10.39 Acres
    • $14,427 per Acre

    PARCEL 91 Cool Spring Rd, Marydel, MD 21649

    Ready for you to build your new home! This beautiful lot is already perc tested for a 3-bedroom home. 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 SRA noted on it so lots of the necessary paperwork is complete. So come see and come buy and

    Bonnie Duley Long & Foster Real Estate, Inc.

    PARCEL 91 Cool Spring Rd, Marydel, MD 21649
  • 6561 Bell Creek Rd, Preston, MD 21655
    6561 Bell Creek Rd, Preston, MD 21655
    6561 Bell Creek Rd, Preston, MD 21655
    /5

    $201,000 Sold Dec 19, 2025

    6561 Bell Creek Rd, Preston, MD 21655

    • 3 Beds
    • 1 Bath
    • 1,350 Sq Ft
    • Built 1915

    Last Sold Summary

    • $149/SF
    • 14 Days On Market

    Last Listing Agent Barbara Dayton Long & Foster Real Estate, Inc.

    6561 Bell Creek Rd, Preston, MD 21655
    • 208 W 2nd St, Ridgely, MD 21660
      208 W 2nd St, Ridgely, MD 21660
      208 W 2nd St, Ridgely, MD 21660
      /25

      Est $202,985 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 962 Sq Ft

      208 W 2nd St, Ridgely, MD 21660

      208 W 2nd St, Ridgely, MD 21660
  • 14957 Cherry Ln, Ridgely, MD 21660
    14957 Cherry Ln, Ridgely, MD 21660
    14957 Cherry Ln, Ridgely, MD 21660
    /67

    $385,000 Pending

    • 3 Beds
    • 3 Baths
    • 2,645 Sq Ft

    14957 Cherry Ln, Ridgely, MD 21660

    Nestled in the serene Meadow Wood subdivision, this charming brick Colonial home offers a perfect blend of comfort and tranquility. With 2.56+/- acres of partly wooded land, enjoy the peaceful ambiance of nature right in your backyard, complete with a picturesque pond view. This 3 Bedroom, 3 Bath home offers 2645 +/- sq ft living space and a true secluded and private country feel. The inviting

    Judith Germain Benson & Mangold, LLC

    14957 Cherry Ln, Ridgely, MD 21660
  • 513 Vaughn Ave, Greensboro, MD 21639
    513 Vaughn Ave, Greensboro, MD 21639
    513 Vaughn Ave, Greensboro, MD 21639
    /13

    $235,000 Sold Jul 31, 2025

    513 Vaughn Ave, Greensboro, MD 21639

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft
    • Built 1996

    Last Sold Summary

    • $204/SF
    • 8 Days On Market

    Current Estimated Value $246,399

    Last Listing Agent Chad Muse KD Realty Inc

    513 Vaughn Ave, Greensboro, MD 21639
    • 25922 Fox Grape Rd, Greensboro, MD 21639
      25922 Fox Grape Rd, Greensboro, MD 21639
      25922 Fox Grape Rd, Greensboro, MD 21639
      /50

      Est $370,928 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,820 Sq Ft

      25922 Fox Grape Rd, Greensboro, MD 21639

      25922 Fox Grape Rd, Greensboro, MD 21639
  • 22005 Main St, Hillsboro, MD 21641
    22005 Main St, Hillsboro, MD 21641
    22005 Main St, Hillsboro, MD 21641
    /74

    $545,000

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

    22005 Main St, Hillsboro, MD 21641

    This fine, brick dwelling originating from the18th c. is situated in Hillsboro on Maryland's peaceful Eastern Shore. Hillsboro, nestled along the Tuckahoe River, conveniently located to all that is important to the Eastern Shore's sought-after lifestyle. The WILLIAM SMITH HOUSE, built in 1794, exemplifies the world of a successful Grain Merchant living in an important hub for grain and tobacco.

    Nancy McGuire Maryland Heritage Properties

    22005 Main St, Hillsboro, MD 21641
  • 1305 Trice Meadows Cir, Denton, MD 21629
    1305 Trice Meadows Cir, Denton, MD 21629
    1305 Trice Meadows Cir, Denton, MD 21629
    /31

    $405,000 Sold Jan 10, 2025

    1305 Trice Meadows Cir, Denton, MD 21629

    • 4 Beds
    • 3 Baths
    • 3,182 Sq Ft
    • Built 2007

    Last Sold Summary

    • $127/SF
    • 38 Days On Market

    Current Estimated Value $450,454

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    1305 Trice Meadows Cir, Denton, MD 21629
    • 288 Tidewater Cir, Preston, MD 21655
      288 Tidewater Cir, Preston, MD 21655
      288 Tidewater Cir, Preston, MD 21655
      /32

      Est $443,279 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,842 Sq Ft

      288 Tidewater Cir, Preston, MD 21655

      288 Tidewater Cir, Preston, MD 21655
  • 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
  • 502 N Academy St, Greensboro, MD 21639
    502 N Academy St, Greensboro, MD 21639
    502 N Academy St, Greensboro, MD 21639
    /59

    $385,000 Sold Nov 07, 2025

    502 N Academy St, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 2,378 Sq Ft
    • Built 1960

    Last Sold Summary

    • $162/SF
    • 105 Days On Market

    Last Listing Agent Chris Rosendale CR Realty

    502 N Academy St, Greensboro, MD 21639
    • 1107 Ruddy Duck Ct, Denton, MD 21629
      1107 Ruddy Duck Ct, Denton, MD 21629
      1107 Ruddy Duck Ct, Denton, MD 21629
      /61

      Est $438,630 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,914 Sq Ft

      1107 Ruddy Duck Ct, Denton, MD 21629

      1107 Ruddy Duck Ct, 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
  • 0 Rte 313 Rd Unit 1001900376, Federalsburg, MD 21632
    0 Rte 313 Rd Unit 1001900376, Federalsburg, MD 21632
    0 Rte 313 Rd Unit 1001900376, Federalsburg, MD 21632
    /4

    $200,000 Sold Jun 09, 2025

    0 Rte 313 Rd Unit 1001900376, Federalsburg, MD 21632

    • Land
    • 40.49 Acres
    • $4,939 per Acre

    Last Sold Summary

    • 29% Below List Price
    • 1,412 Days On Market

    Last Listing Agent Barton Johnson/not int Marshy Hope Realty LLC

    0 Rte 313 Rd Unit 1001900376, Federalsburg, MD 21632
    • 6 Oak St, Ridgely, MD 21660
      6 Oak St, Ridgely, MD 21660
      6 Oak St, Ridgely, MD 21660
      /19

      Est $343,577 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,480 Sq Ft

      6 Oak St, Ridgely, MD 21660

      6 Oak St, Ridgely, MD 21660
  • 24712 Tribbett Cir, Ridgely, MD 21660
    24712 Tribbett Cir, Ridgely, MD 21660
    24712 Tribbett Cir, Ridgely, MD 21660
    /37

    $629,900

    • 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
  • 14581 Poplar St, Goldsboro, MD 21636
    14581 Poplar St, Goldsboro, MD 21636
    14581 Poplar St, Goldsboro, MD 21636
    /11

    $250,000 Sold Mar 24, 2025

    14581 Poplar St, Goldsboro, MD 21636

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 2001

    Last Sold Summary

    • $203/SF
    • 118 Days On Market

    Current Estimated Value $273,865

    Last Listing Agent Peter Mellor Wright Real Estate

    14581 Poplar St, Goldsboro, MD 21636
    • 312 Hughlett St, Preston, MD 21655
      312 Hughlett St, Preston, MD 21655
      312 Hughlett St, Preston, MD 21655
      /18

      Est $392,748 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,130 Sq Ft

      312 Hughlett St, Preston, MD 21655

      312 Hughlett St, Preston, MD 21655
  • 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. 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
  • 421 W Sunset Ave, Greensboro, MD 21639
    421 W Sunset Ave, Greensboro, MD 21639
    421 W Sunset Ave, Greensboro, MD 21639
    /59

    $408,000 Sold Dec 26, 2024

    421 W Sunset Ave, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,904 Sq Ft
    • Built 1966

    Last Sold Summary

    • $214/SF
    • 61 Days On Market

    Current Estimated Value $438,873

    Last Listing Agent Barbara McCaffrey Redfin Corp

    421 W Sunset Ave, Greensboro, MD 21639
    • 3 Robins Ct, Ridgely, MD 21660
      3 Robins Ct, Ridgely, MD 21660
      3 Robins Ct, Ridgely, MD 21660
      /54

      Est $471,286 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,898 Sq Ft

      3 Robins Ct, Ridgely, MD 21660

      3 Robins Ct, Ridgely, MD 21660
  • 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
  • 151 Riverwalk Terrace, Federalsburg, MD 21632
    151 Riverwalk Terrace, Federalsburg, MD 21632
    151 Riverwalk Terrace, Federalsburg, MD 21632
    /28

    $240,990 Sold Jun 30, 2025

    151 Riverwalk Terrace, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 1,365 Sq Ft
    • Built 2025

    Last Sold Summary

    • $177/SF
    • 26 Days On Market

    Current Estimated Value $252,917

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

    151 Riverwalk Terrace, Federalsburg, MD 21632
    • 112 Vernon Ave, Federalsburg, MD 21632
      112 Vernon Ave, Federalsburg, MD 21632
      112 Vernon Ave, Federalsburg, MD 21632
      /10

      Est $157,675 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 884 Sq Ft

      112 Vernon Ave, Federalsburg, MD 21632

      112 Vernon Ave, Federalsburg, MD 21632

Showing Results 441 - 480, Page 12 of 18

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