15,625

Caroline County, MD Homes

Section Image Section Image
    • /31

      Est $382,435

      Not Listed For Sale

      25797 Spring Branch Dr, Greensboro, MD 21639

      • 3 Beds
      • 2 Baths
      • 1,288 Sq Ft
      • Built 1998
      25797 Spring Branch Dr, Greensboro, MD 21639

      Last Sold Summary

      • 54 Days On Market

      Last Listing Agent Rick Parreco RE/MAX Executive

  • /2

    $32,500

    • Land
    • 30,056 Sq Ft
    • $47,101 per Acre

    0 Douglas & Lincoln St Unit MDCM2006716, Ridgely, MD 21660

    Just next to the quaint town of Ridgely, this .69 acre lot also comes with a bonus lot highlighted in photos. Buy and hold as an investment or see if you can perc.

    Michael Rosendale Rosendale Realty

    0 Douglas & Lincoln St Unit MDCM2006716, Ridgely, MD 21660
  • /65

    $485,000

    Sold Jun 24, 2026

    13099 Ridgely Rd, Greensboro, MD 21639

    • 4 Beds
    • 2.5 Baths
    • 1,856 Sq Ft
    • Built 1982

    Last Sold Summary

    • $261/SF
    • 0 Days On Market

    Current Estimated Value $481,085

    Last Listing Agent Brendan Spear Caprika Realty

    13099 Ridgely Rd, Greensboro, MD 21639
    • /26

      Est $230,483

      Not Listed For Sale

      1510 Blue Heron Dr, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,692 Sq Ft
      • Built 2004
      1510 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Dan Foster Long & Foster Real Estate, Inc.

  • /69

    $740,000

    Under Contract
    • 5 Beds
    • 4 Baths
    • 5,286 Sq Ft

    24764 Pealiquor Rd, Denton, MD 21629

    Back on the Market at No Fault of the Seller! Welcome to Timeless Elegance Meets Modern Comfort. Step inside this stunning Cape Cod residence and immediately feel at home. A gracious foyer framed by classic columns invites you into a luminous interior that effortlessly blends traditional charm with modern open‐concept living. To your right, a versatile flex room offers the perfect space for a

    Dustin Parker The Parker Group

    24764 Pealiquor Rd, Denton, MD 21629
  • /2

    $275,000

    Sold Aug 07, 2026

    21134 Dover Bridge Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,586 Sq Ft
    • Built 1966

    Last Sold Summary

    • 2% Above List Price
    • $173/SF
    • 0 Days On Market

    Current Estimated Value $289,774

    Last Listing Agent Iva Herr Benson & Mangold, LLC

    21134 Dover Bridge Rd, Preston, MD 21655
    • /80

      Est $400,633

      Not Listed For Sale

      24300 Robins Creek Rd, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,624 Sq Ft
      • Built 1979
      24300 Robins Creek Rd, Preston, MD 21655

      Last Sold Summary

      • 127 Days On Market

      Last Listing Agent Cheryl Jersey-Lecourt Long & Foster Real Estate, Inc.

  • /62

    $630,000

    Under Contract
    • 4 Beds
    • 3.5 Baths
    • 3,725 Sq Ft

    26927 Boyce Mill Rd, Greensboro, MD 21639

    Nestled on 5 beautiful acres, this spacious 4-bedroom, 3.5-bath home offers the perfect blend of privacy, comfort, and country living. Approximately 1.8 acres are wooded, providing a peaceful backdrop and frequent visits from local wildlife, while the remaining acreage is cleared and ideal for outdoor enjoyment. The inviting front porch overlooks the private rural setting, while the interior

    Barbara Blosser Long & Foster Real Estate, Inc.

    26927 Boyce Mill Rd, Greensboro, MD 21639
  • /17

    $67,000

    Sold Sep 19, 2025

    21182 Marsh Creek Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,116 Sq Ft
    • Built 2020

    Last Sold Summary

    • $60/SF
    • 25 Days On Market

    Last Listing Agent Toni McDowell Keller Williams Select Realtors of Annapolis

    21182 Marsh Creek Rd, Preston, MD 21655
    • /17

      Est $394,352

      Not Listed For Sale

      205 N Main St, Greensboro, MD 21639

      • 5 Beds
      • 3 Baths
      • 3,876 Sq Ft
      • Built 1890
      205 N Main St, Greensboro, MD 21639

      Last Sold Summary

      • 301 Days On Market

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

  • /4

    $21,000

    $14K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,024 Sq Ft

    204 Academy Ave, Federalsburg, MD 21632

    Investor special! This property is being sold AS-IS and is priced for land value or a full renovation. The existing structure requires extensive repairs or complete tear-down—ideal for experienced builders, contractors, or savvy investors looking for a project. Buyer to verify zoning, permits, potential use. Buyer Broker/Agent and/or Buyer must do their own due diligence to verify if the existing

    Mike Dunn Keller Williams Realty Delmarva

    204 Academy Ave, Federalsburg, MD 21632
  • /54

    $499,500

    Sold Sep 22, 2025

    11575 Maplewood Dr, Ridgely, MD 21660

    • 4 Beds
    • 3 Baths
    • 1,900 Sq Ft
    • Built 2020

    Last Sold Summary

    • $263/SF
    • 4 Days On Market

    Current Estimated Value $504,315

    Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

    11575 Maplewood Dr, Ridgely, MD 21660
    • /48

      Est $288,973

      Not Listed For Sale

      219 Briarwood Cir, Denton, MD 21629

      • 4 Beds
      • 4 Baths
      • 2,088 Sq Ft
      • Built 2006
      219 Briarwood Cir, Denton, MD 21629

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Kimberly Dixson Coldwell Banker Realty

  • /23

    $190,000

    $10K PRICE DROP Under Contract
    • 3 Beds
    • 2.5 Baths
    • 1,860 Sq Ft

    1507 Blue Heron Dr, Denton, MD 21629

    3-Story Townhome Ready for Its New Owners!Home offers 3 bedrooms and 2.5 baths with a functional layout and comfortable living spaces. The spacious first floor features an open living area and convenient half bath for guests.The second floor includes two bedrooms, a full bath, and laundry area, providing everyday convenience. The third-floor primary suite offers a private retreat with a

    KL Harris Keller Williams Select Realtors of Cambridge

    1507 Blue Heron Dr, Denton, MD 21629
  • /8

    $129,000

    Sold Apr 01, 2026

    0 Burnt Mill Rd Unit MDCM2005292, Ridgely, MD 21660

    • Land
    • 3.51 Acres
    • $36,752 per Acre

    Last Sold Summary

    • 381 Days On Market

    Last Listing Agent Gretchen Wichlinski Compass

    0 Burnt Mill Rd Unit MDCM2005292, Ridgely, MD 21660
    • /9

      Est $113,000

      Not Listed For Sale

      25782 Goldsboro Rd, Goldsboro, MD 21636

      • 2 Beds
      • 1 Bath
      • 1,386 Sq Ft
      • Built 1910
      25782 Goldsboro Rd, Goldsboro, MD 21636

      Last Sold Summary

      • 46 Days On Market

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

  • /2

    $60,000

    • Land
    • 1 Acre
    • $60,000 per Acre

    27286 Willin Ln, Federalsburg, MD 21632

    Private 1-acre wooded lot with deeded access via a dirt road. Enjoy a secluded setting surrounded by nature, perfect for those looking to get away from it all. Great opportunity for a future homesite or recreational use (subject to county approvals). Motivated seller—bring all reasonable offers!

    Janet Todd Harlan C. Williams Co.

    27286 Willin Ln, Federalsburg, MD 21632
  • /2

    $50,000

    Sold May 29, 2026

    17485 Henderson Rd, Marydel, MD 21649

    • Land
    • 3,049 Sq Ft
    • $714,286 per Acre

    Last Sold Summary

    • 7 Days On Market

    Current Estimated Value $52,149

    Last Listing Agent Andrew Beaven Wright Real Estate

    17485 Henderson Rd, Marydel, MD 21649
    • /11

      Est $290,274

      Not Listed For Sale

      408 Maple Ave, Ridgely, MD 21660

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1978
      408 Maple Ave, Ridgely, MD 21660

      Last Sold Summary

      • 62 Days On Market

      Last Listing Agent Bonnie Duley Long & Foster Real Estate, Inc.

  • /13

    $109,000

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

    4471 Harmony Rd, Preston, MD 21655

    Discover the potential in this ranch-style home situated on a spacious lot in Caroline County. This property is ready for renovation and offers a great opportunity to update and customize to your vision. Major improvements have already been completed, including a newer roof and updated windows, providing a solid starting point for your renovation plans. The home is served by a private well and

    Norman Domingo XRealty.NET LLC

    4471 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

    Current Estimated Value $337,847

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    6315 Harmony Rd, Preston, MD 21655
    • /20

      Est $253,247

      Not Listed For Sale

      411 N 6th St, Denton, MD 21629

      • 3 Beds
      • 1 Bath
      • 1,364 Sq Ft
      • Built 1900
      411 N 6th St, Denton, MD 21629

      Last Sold Summary

      • 115 Days On Market

      Last Listing Agent Kat Thompson Benson & Mangold, LLC.

  • /30

    $355,000

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft

    8140 Haven St, Denton, MD 21629

    This charming ranch-style home, built in 1986, offers a perfect blend of comfort and functionality. Minutes to Tuckahoe Creek boat ramp! With 1,300 sq. ft. of well-designed space, it features three inviting bedrooms and two full bathrooms, including a primary suite with a walk-in closet and a tub/shower. The traditional floor plan is enhanced by built-ins and ceiling fans, creating a cozy

    Mary Haddaway Benson & Mangold, LLC

    8140 Haven St, Denton, MD 21629
  • /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

    Current Estimated Value $226,318

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

    6561 Bell Creek Rd, Preston, MD 21655
    • /13

      Est $207,062

      Not Listed For Sale

      101 Vaughn Ave, Greensboro, MD 21639

      • 2 Beds
      • 1 Bath
      • 1,004 Sq Ft
      • Built 1950
      101 Vaughn Ave, Greensboro, MD 21639

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Kat Thompson Benson & Mangold, LLC.

  • /46

    $465,000

    Open Sat 11AM - 1PM
    • 3 Beds
    • 2 Baths
    • 2,240 Sq Ft

    23118 Tuckahoe Springs Dr, Denton, MD 21629

    Eastern Shore living at its finest! Nestled in the desirable Tuckahoe Springs subdivision, this beautifully maintained home offers the perfect blend of comfort, style, and serene outdoor living. Step inside to an inviting foyer that leads to a dedicated laundry area and an expansive, well‐appointed kitchen featuring cabinetry galore, upgraded stainless‐steel appliances, and quartz countertops.

    Amanda Morgan Brenton Realty Group

    23118 Tuckahoe Springs Dr, Denton, MD 21629
  • /2

    $273,990

    Sold Jan 15, 2026

    129 Hobbs St, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 1% Below List Price
    • $232/SF
    • 14 Days On Market

    D.R. Horton Kinnamon Meadows

    129 Hobbs St, Greensboro, MD 21639
    • /32

      Est $450,392

      Not Listed For Sale

      288 Tidewater Cir, Preston, MD 21655

      • 4 Beds
      • 2.5 Baths
      • 2,842 Sq Ft
      • Built 2006
      288 Tidewater Cir, Preston, MD 21655

      Last Sold Summary

      • 56 Days On Market

      Last Listing Agent Richard Pullin Weichert, REALTORS

  • /25

    $334,900

    $5K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,440 Sq Ft

    147 Mill St, Preston, MD 21655

    Well Maintained 4 Bed 2 Full Bath Cape Cod. Large Eat-in Kitchen w/ Stainless Steel Appliances, Granite Countertops and Center Island!Nice Size Family Room. Outdoors feature a Large Shed with Heat and Air (currently used as a very nice office) , Separate Shed for storage at the back of Spacious level Lot. Patio for entertaining and more... Home is less than 1 Mile to Choptank River Landing!

    Kathleen Brenton Brenton Realty Group

    147 Mill St, Preston, MD 21655
  • /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

    Current Estimated Value $379,766

    Last Listing Agent Chris Rosendale CR Realty

    502 N Academy St, Greensboro, MD 21639
    • /15

      Est $400,106

      Not Listed For Sale

      1104 Canvasback Ln, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,988 Sq Ft
      • Built 2006
      1104 Canvasback Ln, Denton, MD 21629

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Kevin Waterman Coldwell Banker Waterman Realty

  • /2

    $429,499

    • 6 Beds
    • 2.5 Baths
    • 2,934 Sq Ft

    304 Tidewater Cir, Preston, MD 21655

    LOVELY Tidewater Farms home with a light, open layout and plenty of space to enjoy. The main level features a spacious breakfast room, open kitchen and great room with a center island, eat-at bar, and gas fireplace. There is also a 19' x 15' bonus room and convenient upstairs laundry. The primary suite offers walk-in closets, a soaking tub, separate shower, and double sink vanity. Outside, enjoy

    Judah Fashe Samson Properties

    304 Tidewater Cir, Preston, MD 21655
  • /2

    $90,000

    Sold Apr 07, 2026

    103 S Main St, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 2,116 Sq Ft
    • Built 1890

    Last Sold Summary

    • 5% Below List Price
    • $43/SF
    • 18 Days On Market

    Last Listing Agent Valerie Brown Coldwell Banker Realty

    103 S Main St, Federalsburg, MD 21632
    • /19

      Est $329,718

      Not Listed For Sale

      6 Oak St, Ridgely, MD 21660

      • 3 Beds
      • 2 Baths
      • 1,480 Sq Ft
      • Built 1979
      6 Oak St, Ridgely, MD 21660

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Heather Brummell Keller Williams Realty

  • /35

    $265,000

    • 3 Beds
    • 2.5 Baths
    • 1,584 Sq Ft

    530 Vaughn Ave, Greensboro, MD 21639

    **Seller is offering $7,500 towards buyers closing costs with an acceptable offer** Welcome home to this beautifully updated 3-bedroom, 2.5-bath home built by Gemcraft Homes in 2002. Freshly painted throughout in 2026, this move-in-ready home also features brand-new luxury vinyl plank flooring on the main level and new carpet throughout the second floor, offering a fresh, modern feel from the

    Hunter Geary Hyatt & Company Real Estate, LLC

    530 Vaughn Ave, Greensboro, MD 21639
  • /18

    $75,000

    Sold Jun 01, 2026

    215 Academy Ave, Federalsburg, MD 21632

    • 2 Beds
    • 2 Baths
    • 1,520 Sq Ft
    • Built 1903

    Last Sold Summary

    • 21% Below List Price
    • $49/SF
    • 40 Days On Market

    Current Estimated Value $129,333

    Last Listing Agent Nora Turner Long & Foster Real Estate, Inc.

    215 Academy Ave, Federalsburg, MD 21632
    • /36

      Est $474,310

      Not Listed For Sale

      11412 Cecil Ct, Greensboro, MD 21639

      • 4 Beds
      • 2.5 Baths
      • 2,100 Sq Ft
      • Built 2005
      11412 Cecil Ct, Greensboro, MD 21639

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Deborah Shiley Long & Foster Real Estate, Inc.

  • /14

    $282,990

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft

    Curtis Plan at Kinnamon Meadows, Greensboro, MD 21639

    The Curtis is a 1,182 square foot, cottage-style ranch home with three bedrooms and two bathrooms. As you enter the home through the front porch, this thoughtfully designed home has a grand open concept living area that leads into the spacious kitchen. To the right, a long, main hallway allows for the two guest bedrooms and guest bathroom to be separate from the living areas of the home. Along

    D.R. Horton Builder
    103 Park Ave Unit 36203276, Greensboro, MD 21639
  • /5

    $295,000

    Sold Jan 30, 2026

    3376 Jefferson Pond Rd, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2025

    Last Sold Summary

    • $219/SF
    • 182 Days On Market

    Last Listing Agent Amy Herr Keller Williams Realty

    3376 Jefferson Pond Rd, Federalsburg, MD 21632
    • /32

      Est $251,361

      Not Listed For Sale

      203 Greenridge Rd, Federalsburg, MD 21632

      • 3 Beds
      • 2 Baths
      • 1,479 Sq Ft
      • Built 1938
      203 Greenridge Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Meme ELLIS Keller Williams Realty

Showing Results 441 - 480, Page 12 of 18

How to Buy a Home How to Finance a Home How to Sell a Home