15,671

Caroline County, MD Homes

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    • 8614 Andersontown Rd, Denton, MD 21629
      8614 Andersontown Rd, Denton, MD 21629
      8614 Andersontown Rd, Denton, MD 21629
      /37

      Est $432,007 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,300 Sq Ft

      8614 Andersontown Rd, Denton, MD 21629

      8614 Andersontown Rd, Denton, MD 21629
  • 7 W Belle St, Ridgely, MD 21660
    7 W Belle St, Ridgely, MD 21660
    7 W Belle St, Ridgely, MD 21660
    /23

    $495,000

    • 0.5 Baths
    • 3,321 Sq Ft

    7 W Belle St, Ridgely, MD 21660

    Over 3,300 sq. ft. two-story building, constructed in 2006, offers endless potential with a little imagination. Currently a pharmacy, gift shop, and ice cream parlor, it could easily be transformed into a fantastic four-bedroom, 2.5-bath residence or adapted for other mixed-use purposes. Both levels feature open, flexible layouts—ready to be reimagined to suit your vision.Located in the

    Traci Jordan Meredith Fine Properties

    7 W Belle St, Ridgely, MD 21660
  • 3297 Gallagher Rd, Preston, MD 21655
    3297 Gallagher Rd, Preston, MD 21655
    3297 Gallagher Rd, Preston, MD 21655
    /72

    $320,000 Sold May 02, 2025

    3297 Gallagher Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,544 Sq Ft
    • Built 1994

    Last Sold Summary

    • $207/SF
    • 84 Days On Market

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

    3297 Gallagher Rd, Preston, MD 21655
    • 309 S University Ave, Federalsburg, MD 21632
      309 S University Ave, Federalsburg, MD 21632
      309 S University Ave, Federalsburg, MD 21632
      /9

      Est $162,089 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,296 Sq Ft

      309 S University Ave, Federalsburg, MD 21632

      309 S University Ave, Federalsburg, MD 21632
  • 14 N Maple Ave, Ridgely, MD 21660
    14 N Maple Ave, Ridgely, MD 21660
    14 N Maple Ave, Ridgely, MD 21660
    /19

    $315,000 Pending

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

    14 N Maple Ave, Ridgely, MD 21660

    Fully Renovated Rancher with a bonus shed fitted out with electric and drywall!Welcome to this beautifully remodeled 3-bedroom, 1-bath ranch-style home in the heart of Ridgely, Maryland. Every inch of this home has been thoughtfully updated—featuring a brand new roof, siding, energy-efficient windows, and new front and back doors for enhanced curb appeal and peace of mind.Step inside

    Joshua Clark Chesapeake Real Estate Associates, LLC

    14 N Maple Ave, Ridgely, MD 21660
  • 0 Cool Spring Rd Unit MDCM2005520, Marydel, MD 21649
    0 Cool Spring Rd Unit MDCM2005520, Marydel, MD 21649
    0 Cool Spring Rd Unit MDCM2005520, Marydel, MD 21649
    /49

    $750,000 Sold Nov 12, 2025

    0 Cool Spring Rd Unit MDCM2005520, Marydel, MD 21649

    • Land
    • 187 Acres
    • $4,011 per Acre

    Last Sold Summary

    • 139 Days On Market

    Last Listing Agent Benjamin Alder The Land Group

    0 Cool Spring Rd Unit MDCM2005520, Marydel, MD 21649
    • 4925 Edmondson Creek Rd, Preston, MD 21655
      4925 Edmondson Creek Rd, Preston, MD 21655
      4925 Edmondson Creek Rd, Preston, MD 21655
      /58

      Est $610,875 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,988 Sq Ft

      4925 Edmondson Creek Rd, Preston, MD 21655

      4925 Edmondson Creek Rd, Preston, MD 21655
  • 505 Maryland Ave, Ridgely, MD 21660
    505 Maryland Ave, Ridgely, MD 21660
    505 Maryland Ave, Ridgely, MD 21660
    /23

    $299,000

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    505 Maryland Ave, Ridgely, MD 21660

    Welcome to this beautifully updated 3-bedroom, 2-bath rancher located in the charming town of Ridgely, Maryland. Renovated just about two years ago, this home has been lovingly maintained and offers stylish, move-in-ready living with modern finishes throughout. The open-concept kitchen features granite countertops, a spacious island perfect for entertaining, soft-close cabinetry, and

    Kaitlyn Collins Benson & Mangold, LLC

    505 Maryland Ave, Ridgely, MD 21660
  • 130 Walnut St, Ridgely, MD 21660
    130 Walnut St, Ridgely, MD 21660
    130 Walnut St, Ridgely, MD 21660
    /27

    $369,000 Sold Nov 17, 2025

    130 Walnut St, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,548 Sq Ft
    • Built 2011

    Last Sold Summary

    • $238/SF
    • 5 Days On Market

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

    130 Walnut St, Ridgely, MD 21660
    • 24754 Pealiquor Rd, Denton, MD 21629
      24754 Pealiquor Rd, Denton, MD 21629
      24754 Pealiquor Rd, Denton, MD 21629
      /124

      Est $741,671 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,921 Sq Ft

      24754 Pealiquor Rd, Denton, MD 21629

      24754 Pealiquor Rd, Denton, MD 21629
  • 27329 Iron Gate Rd, Federalsburg, MD 21632
    27329 Iron Gate Rd, Federalsburg, MD 21632
    27329 Iron Gate Rd, Federalsburg, MD 21632
    /43

    $475,000

    • 3 Beds
    • 2 Baths
    • 2,038 Sq Ft

    27329 Iron Gate Rd, Federalsburg, MD 21632

    Charming Colonial-style farmhouse set on 9 scenic acres, offering a rare blend of historic character, pastoral beauty, and endless potential. Ideal for animal lovers or those seeking a peaceful weekend retreat, the home features hardwood floors, exposed ceiling beams, and three wood-burning stoves that add warmth and timeless appeal. Large Spacious bedrooms, a screened porch and rear patio

    Shannon Parker Keller Williams Select Realtors of Cambridge

    27329 Iron Gate Rd, Federalsburg, MD 21632
  • 4516 Frazier Neck Rd, Preston, MD 21655
    4516 Frazier Neck Rd, Preston, MD 21655
    4516 Frazier Neck Rd, Preston, MD 21655
    /13

    $350,000 Sold Sep 05, 2025

    4516 Frazier Neck Rd, Preston, MD 21655

    • 2 Beds
    • 1 Bath
    • 1,050 Sq Ft
    • Built 1969

    Last Sold Summary

    • $333/SF
    • 5 Days On Market

    Current Estimated Value $361,189

    Last Listing Agent Benjamin Alder The Land Group

    4516 Frazier Neck Rd, Preston, MD 21655
    • 25698 Caroline St, Greensboro, MD 21639
      25698 Caroline St, Greensboro, MD 21639
      25698 Caroline St, Greensboro, MD 21639
      /26

      Est $406,681 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,512 Sq Ft

      25698 Caroline St, Greensboro, MD 21639

      25698 Caroline St, Greensboro, MD 21639
  • 305 Central Ave, Ridgely, MD 21660
    305 Central Ave, Ridgely, MD 21660
    305 Central Ave, Ridgely, MD 21660
    /19

    $299,000 Open Sat 9AM - 11AM

    • 5 Beds
    • 2 Baths
    • 2,574 Sq Ft

    305 Central Ave, Ridgely, MD 21660

    Welcome home to this spacious 5-bedroom, 2-bath Colonial located in the heart of Ridgely. This in-town property offers a large kitchen with plenty of space for cooking and entertaining, a comfortable living room, and generously sized bedrooms throughout. The traditional floor plan provides a warm and inviting flow, perfect for both daily living and hosting guests. Enjoy the convenience of being

    Katie Moore Coldwell Banker Chesapeake Real Estate Company

    305 Central Ave, Ridgely, MD 21660
  • 312 Fountain Ave, Denton, MD 21629
    312 Fountain Ave, Denton, MD 21629
    312 Fountain Ave, Denton, MD 21629
    /38

    $245,000 Sold Nov 14, 2025

    312 Fountain Ave, Denton, MD 21629

    • 3 Beds
    • 1.5 Baths
    • 1,092 Sq Ft
    • Built 1982

    Last Sold Summary

    • $224/SF
    • 72 Days On Market

    Last Listing Agent Pamela Ackermann-Doll RE/MAX Executive

    312 Fountain Ave, Denton, MD 21629
    • 8157 Arch Dr, Denton, MD 21629
      8157 Arch Dr, Denton, MD 21629
      8157 Arch Dr, Denton, MD 21629
      /34

      Est $378,099 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,232 Sq Ft

      8157 Arch Dr, Denton, MD 21629

      8157 Arch Dr, Denton, MD 21629
  • 0 Mill & Lincoln St, Greensboro, MD 21639
    0 Mill & Lincoln St, Greensboro, MD 21639
    0 Mill & Lincoln St, Greensboro, MD 21639
    /9

    $87,500

    • Land
    • 0.74 Acre
    • $118,243 per Acre

    0 Mill & Lincoln St, Greensboro, MD 21639

    NEW PRICE!!! Unique Opportunity to purchase 3 Parcels in the Town of Greensboro!! One of which has a hooked up Water/Sewer account, so instant savings on no tap fee!! Parcels are believed to total approximately 0.74 Acres, more or less. Dilapidated dwelling exists in the center of the parcels, in need of tear down or possible major renovation. Town of Greensboro building codes and ordinances

    Erin Anderson Chesapeake Real Estate Associates, LLC

    0 Mill & Lincoln St, Greensboro, MD 21639
  • 125 Park Ave, Greensboro, MD 21639

    $292,990 Sold Oct 28, 2025

    • 1,460 Sq Ft
    • $201/SF
    • 4 Beds
    • 2 Baths
    • Built 2025

    125 Park Ave, Greensboro, MD 21639

    Welcome to 125 Parkland Road, a new home under construction in our newest community Kinnamon Meadows in 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 the home.

    D.R. Horton

    125 Park Ave, Greensboro, MD 21639
    • 108 Roe St, Greensboro, MD 21639
      108 Roe St, Greensboro, MD 21639
      108 Roe St, Greensboro, MD 21639
      /8

      Est $179,924 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 845 Sq Ft

      108 Roe St, Greensboro, MD 21639

      108 Roe St, Greensboro, MD 21639
  • 208 S 3rd St, Denton, MD 21629
    208 S 3rd St, Denton, MD 21629
    /2

    $200,000 Pending

    • 3 Beds
    • 1 Bath
    • 1,136 Sq Ft

    208 S 3rd St, Denton, MD 21629

    Step into this charming Victorian home, a delightful blend of classic elegance and modern comfort. With three spacious bedrooms and a full bathroom, this residence offers a warm and inviting atmosphere perfect for relaxation and gatherings. The traditional floor plan enhances the flow of the living spaces, while the hardwood flooring adds a touch of timeless beauty. The heart of the home features

    SALLY KERCHNER Benson & Mangold, LLC

    208 S 3rd St, Denton, MD 21629
  • 301 Greenridge Rd, Federalsburg, MD 21632
    301 Greenridge Rd, Federalsburg, MD 21632
    /2

    $100,000 Sold Feb 26, 2025

    301 Greenridge Rd, Federalsburg, MD 21632

    • 2 Beds
    • 1 Bath
    • 816 Sq Ft
    • Built 1954

    Last Sold Summary

    • $123/SF
    • 1 Day On Market

    Current Estimated Value $108,277

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

    301 Greenridge Rd, Federalsburg, MD 21632
    • 1709 Cattail Commons Way, Denton, MD 21629
      1709 Cattail Commons Way, Denton, MD 21629
      1709 Cattail Commons Way, Denton, MD 21629
      /52

      Est $408,405 Not Listed For Sale

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

      1709 Cattail Commons Way, Denton, MD 21629

      1709 Cattail Commons Way, Denton, MD 21629
  • 14271 Cedar Ln, Greensboro, MD 21639
    14271 Cedar Ln, Greensboro, MD 21639
    14271 Cedar Ln, Greensboro, MD 21639
    /113

    $1,475,000

    • 6 Beds
    • 3 Baths
    • 3,756 Sq Ft

    14271 Cedar Ln, Greensboro, MD 21639

    Back on the Market due to Buyer's FSA financing falling through. SELLER NOW OFFERING A $20,000 CREDIT TOWARDS FRESH PAINT & NEW CARPET! Welcome to Thanksgiving Farm, an exceptional opportunity to own nearly 100 acres of prime Eastern Shore farmland just minutes from charming small towns and within easy reach of Ocean City, Annapolis, and major airports. This versatile estate includes two parcels

    Travis Gray Engel & Völkers Annapolis

    14271 Cedar Ln, Greensboro, MD 21639
  • 22040 Main St, Hillsboro, MD 21641
    22040 Main St, Hillsboro, MD 21641
    22040 Main St, Hillsboro, MD 21641
    /83

    $305,000 Sold Feb 13, 2025

    22040 Main St, Hillsboro, MD 21641

    • 4 Beds
    • 1.5 Baths
    • 2,276 Sq Ft
    • Built 1900

    Last Sold Summary

    • $134/SF
    • 68 Days On Market

    Current Estimated Value $324,072

    Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

    22040 Main St, Hillsboro, MD 21641
    • 505 Teal Cir, Greensboro, MD 21639
      505 Teal Cir, Greensboro, MD 21639
      505 Teal Cir, Greensboro, MD 21639
      /43

      Est $349,915 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,952 Sq Ft

      505 Teal Cir, Greensboro, MD 21639

      505 Teal Cir, Greensboro, MD 21639
  • 406 Wood Duck Dr, Greensboro, MD 21639
    406 Wood Duck Dr, Greensboro, MD 21639
    406 Wood Duck Dr, Greensboro, MD 21639
    /41

    $325,000

    • 3 Beds
    • 2.5 Baths
    • 1,364 Sq Ft

    406 Wood Duck Dr, Greensboro, MD 21639

    BACK ON THE MARKET! Buyers home sale contingency fell through days before settlement! This beautiful colonial, in the heart of Greensboro is one you don’t want to miss! Featuring a traditional two story floor plan, this home welcomes you from the start. This 3 bedroom, and 2.5 bathroom home offers a move in ready space to make your own! As you enter you’ll love the newer vinyl plank flooring

    Brittany Gough RE/MAX One

    406 Wood Duck Dr, Greensboro, MD 21639
  • 1208 Painted Fern Rd, Denton, MD 21629
    1208 Painted Fern Rd, Denton, MD 21629
    1208 Painted Fern Rd, Denton, MD 21629
    /39

    $400,000 Sold Dec 12, 2025

    1208 Painted Fern Rd, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,994 Sq Ft
    • Built 2006

    Last Sold Summary

    • $134/SF
    • 8 Days On Market

    Last Listing Agent Janet Powers Berkshire Hathaway Homeservice Homesale Realty

    1208 Painted Fern Rd, Denton, MD 21629
    • 316 N Main St, Greensboro, MD 21639
      316 N Main St, Greensboro, MD 21639
      316 N Main St, Greensboro, MD 21639
      /28

      Est $220,028 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,272 Sq Ft

      316 N Main St, Greensboro, MD 21639

      316 N Main St, Greensboro, MD 21639
  • 306 S Main St, Federalsburg, MD 21632
    306 S Main St, Federalsburg, MD 21632
    306 S Main St, Federalsburg, MD 21632
    /41

    $269,900

    • 4 Beds
    • 1.5 Baths
    • 2,820 Sq Ft

    306 S Main St, Federalsburg, MD 21632

    Bring Your Fishing Boat! Nestled along the tranquil waters of Marshyhope Creek, this waterfront retreat offers peaceful views and the rare opportunity to fish or kayak directly from your own private shoreline. This charming 2,820 sq. ft. Victorian home features 4 spacious, freshly painted bedrooms and 1.5 baths and is ready for you to add your special touches. Begin your mornings with coffee on

    Mary Mabry Keller Williams Select Realtors of Cambridge

    306 S Main St, Federalsburg, MD 21632
  • 318 S 5th Ave, Denton, MD 21629
    318 S 5th Ave, Denton, MD 21629
    /2

    $258,000 Sold Aug 18, 2025

    318 S 5th Ave, Denton, MD 21629

    • 2 Beds
    • 1.5 Baths
    • 1,326 Sq Ft
    • Built 1953

    Last Sold Summary

    • $195/SF
    • 1 Day On Market

    Current Estimated Value $258,370

    Last Listing Agent Barbara Beaudet Brenton Realty Group

    318 S 5th Ave, Denton, MD 21629
    • 25720 Burrsville Rd, Denton, MD 21629
      25720 Burrsville Rd, Denton, MD 21629
      25720 Burrsville Rd, Denton, MD 21629
      /51

      Est $339,232 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 936 Sq Ft

      25720 Burrsville Rd, Denton, MD 21629

      25720 Burrsville Rd, Denton, MD 21629
  • 22415 Hillsboro Rd, Denton, MD 21629
    22415 Hillsboro Rd, Denton, MD 21629
    /2

    $89,900 Under Contract

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

    22415 Hillsboro Rd, Denton, MD 21629

    Seller Requestes to use Cardinal Title. Sold AS-IS and Priced to Sell!Located on a quiet rural road, this 1-acre property is ideal for investors, homeowners or builders. Major rehab needed or tear down and build your dream home. Great opportunity!

    TAMMY GREEN Samson Properties

    22415 Hillsboro Rd, Denton, MD 21629
  • 25612 Auction Rd, Federalsburg, MD 21632
    25612 Auction Rd, Federalsburg, MD 21632
    25612 Auction Rd, Federalsburg, MD 21632
    /71

    $429,000 Sold Jul 07, 2025

    25612 Auction Rd, Federalsburg, MD 21632

    • 3 Beds
    • 1 Bath
    • 1,648 Sq Ft
    • Built 1984

    Last Sold Summary

    • $260/SF
    • 29 Days On Market

    Current Estimated Value $441,453

    Last Listing Agent Megan Rosendale Rosendale Realty

    25612 Auction Rd, Federalsburg, MD 21632
    • 1610 Cattail Commons Way, Denton, MD 21629
      1610 Cattail Commons Way, Denton, MD 21629
      1610 Cattail Commons Way, Denton, MD 21629
      /34

      Est $420,265 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,056 Sq Ft

      1610 Cattail Commons Way, Denton, MD 21629

      1610 Cattail Commons Way, Denton, MD 21629
  • 409 Main St, Goldsboro, MD 21636
    409 Main St, Goldsboro, MD 21636
    409 Main St, Goldsboro, MD 21636
    /19

    $205,000 Under Contract

    • 2 Beds
    • 1.5 Baths
    • 1,252 Sq Ft

    409 Main St, Goldsboro, MD 21636

    Welcome to 409 Main Street, a delightful 2 bedroom, 1.5 bath home nestled in the heart of Goldsboro. This property features a cozy living room with pellet stove, dining room, a functional kitchen, bonus room (use as an office or 3rd bedroom), comfortable bedrooms and a basement offering endless potential for storage, a workshop, or future finished space. Enjoy peaceful mornings or evenings on the

    Amy Betts Coldwell Banker Realty

    409 Main St, Goldsboro, MD 21636
  • 5026 Bethlehem Rd, Preston, MD 21655
    5026 Bethlehem Rd, Preston, MD 21655
    5026 Bethlehem Rd, Preston, MD 21655
    /15

    $55,000 Sold Apr 14, 2025

    5026 Bethlehem Rd, Preston, MD 21655

    • 3 Beds
    • 1.5 Baths
    • 1,845 Sq Ft
    • Built 1890

    Last Sold Summary

    • $30/SF
    • 201 Days On Market

    Current Estimated Value $229,506

    Last Listing Agent Wes Russum Coldwell Banker Chesapeake Real Estate Company

    5026 Bethlehem Rd, Preston, MD 21655
    • 25711 Mockingbird Ln, Greensboro, MD 21639
      25711 Mockingbird Ln, Greensboro, MD 21639
      25711 Mockingbird Ln, Greensboro, MD 21639
      /47

      Est $402,397 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,768 Sq Ft

      25711 Mockingbird Ln, Greensboro, MD 21639

      25711 Mockingbird Ln, Greensboro, MD 21639
  • 321 S Main St, Federalsburg, MD 21632
    321 S Main St, Federalsburg, MD 21632
    /2

    $129,000

    • 6 Beds
    • 2 Baths
    • 2,400 Sq Ft

    321 S Main St, Federalsburg, MD 21632

    tenant occupied duplex rented for 1600/ month. agent is owner

    Bo Claggett Coldwell Banker Realty

    321 S Main St, Federalsburg, MD 21632
  • 214 S 1st St, Denton, MD 21629
    214 S 1st St, Denton, MD 21629
    214 S 1st St, Denton, MD 21629
    /39

    $655,000 Sold Apr 04, 2025

    214 S 1st St, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 2,182 Sq Ft
    • Built 1953

    Last Sold Summary

    • $300/SF
    • 48 Days On Market

    Current Estimated Value $698,800

    Last Listing Agent Sharon DeGrouchy Long & Foster Real Estate, Inc.

    214 S 1st St, Denton, MD 21629
    • 1524 Cattail Commons Way, Denton, MD 21629
      1524 Cattail Commons Way, Denton, MD 21629
      1524 Cattail Commons Way, Denton, MD 21629
      /35

      Est $444,931 Not Listed For Sale

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

      1524 Cattail Commons Way, Denton, MD 21629

      1524 Cattail Commons Way, Denton, MD 21629

Showing Results 201 - 240, Page 6 of 18

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