15,718

Caroline County, MD Homes

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  • /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
    • /13

      Est $270,859

      Not Listed For Sale

      25 Greenridge Ave, Ridgely, MD 21660

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft
      • Built 1993
      25 Greenridge Ave, Ridgely, MD 21660

      Last Sold Summary

      • 7 Days On Market

  • /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
  • /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 $238,114

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

    151 Riverwalk Terrace, Federalsburg, MD 21632
    • /56

      Est $367,970

      Not Listed For Sale

      12710 Greensboro Rd, Greensboro, MD 21639

      • 3 Beds
      • 2.5 Baths
      • 1,472 Sq Ft
      • Built 1950
      12710 Greensboro Rd, Greensboro, MD 21639

      Last Sold Summary

      • 5 Days On Market

  • /3

    $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
  • /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 $155,472

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

    215 Academy Ave, Federalsburg, MD 21632
    • /41

      Est $272,804

      Not Listed For Sale

      1915 Blue Heron Dr, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,640 Sq Ft
      • Built 2006
      1915 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 13 Days On Market

  • /23

    $298,990

    New Construction Pending
    • 3 Beds
    • 2 Baths
    • 1,219 Sq Ft

    123 Hobbs St, Greensboro, MD 21639

    Welcome to 123 Hobbs Street where a soon to be built new home can be yours in Kinnamon Meadows in Greensboro, MD. The Sullivan is a charming 1,219-square-foot, cottage-style ranch home featuring three bedrooms, two bathrooms, and a one-car garage. Just off the foyer, two spacious guest bedrooms and a shared full bathroom offer comfort and privacy for family or visitors. The open-concept kitchen

    Justin Wood D.R. Horton Realty of Virginia, LLC

    123 Hobbs St, 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
    • /31

      Est $360,394

      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

  • /23

    $749,000

    Pending

    21682 Dover Bridge Rd, Preston, MD 21655

    Beautiful farm outside of Preston. 2 parcels included in the sale totaling 95+/- acres improved with a 4 bay run in shed with power and an additional storage shed. Incredible hunting and there was a perc on the property however would need to be re-evaluated.

    Jim Corson Benson & Mangold, LLC

    21682 Dover Bridge Rd, Preston, MD 21655
  • /2

    $269,990

    Sold Oct 13, 2025

    113 Parkland Rd, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,219 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $221/SF
    • 19 Days On Market

    D.R. Horton Kinnamon Meadows

    113 Parkland Rd, Greensboro, MD 21639
    • /26

      Est $228,749

      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

  • /67

    $679,000

    • 4 Beds
    • 2.5 Baths
    • 2,744 Sq Ft

    132 Deep Shore Rd, Denton, MD 21629

    Welcome to 132 Deep Shore Rd—an inviting homestead set on more than 3 acres of beautifully maintained gardens, thoughtfully designed outdoor spaces, and versatile outbuildings. From greenhouse and herb beds to a dedicated drying room and casual nooks for lounging, every corner invites you to savor the seasons. Inside, this spacious home offers over 2,700 sq ft with 4 bedrooms and 2.5 baths. An

    Roger Boyce Chesapeake Real Estate Associates, LLC

    132 Deep Shore Rd, Denton, MD 21629
  • /25

    $260,000

    Sold Oct 30, 2025

    1904 Blue Heron Dr, Denton, MD 21629

    • 4 Beds
    • 3.5 Baths
    • 2,640 Sq Ft
    • Built 2007

    Last Sold Summary

    • $98/SF
    • 61 Days On Market

    Current Estimated Value $254,018

    Last Listing Agent Ralph Harvey ListWithFreedom.com

    1904 Blue Heron Dr, Denton, MD 21629
    • /80

      Est $392,324

      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

  • /2

    $272,000

    $2K PRICE INCREASE
    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    325 Carter Ave, Denton, MD 21629

    Excellent cozy home just waiting for you in the town of Denton with the small town atmosphere and a lot of amenities. Affordably priced, close to shopping, easy commute to the Western Shore and close enough to Delaware and Maryland beaches. Come see today because this home will not last long.

    George Thompson Long & Foster Real Estate, Inc.

    325 Carter Ave, Denton, MD 21629
  • /13

    $260,000

    Sold Aug 13, 2025

    306 Sunrise Ave, Ridgely, MD 21660

    • 4 Beds
    • 2 Baths
    • 1,539 Sq Ft
    • Built 1955

    Last Sold Summary

    • $169/SF
    • 120 Days On Market

    Current Estimated Value $276,009

    Last Listing Agent Wanda Hampton Clark & Co Realty, LLC

    306 Sunrise Ave, Ridgely, MD 21660
    • /17

      Est $363,343

      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

  • /56

    $525,000

    Under Contract
    • 4 Beds
    • 3 Baths
    • 2,016 Sq Ft

    27518 Possum Hill Rd, Federalsburg, MD 21632

    Situated on 10.2+/- acres with wide-open farm views, this 4-bedroom, 3-bath Cape Cod offers a practical layout and plenty of space to enjoy country living. The main level features a primary suite, an additional bedroom, and a kitchen with stainless steel appliances that opens to the living room. Hardwood floors run throughout the main living areas. Upstairs, you'll find a lounge area, two

    Alicia Gannon Dulin Benson & Mangold, LLC

    27518 Possum Hill Rd, Federalsburg, MD 21632
  • /18

    $425,000

    Sold Jul 23, 2025

    8 N 2nd St, Denton, MD 21629

    • Studio
    • 3,482 Sq Ft
    • Built 1890

    Last Sold Summary

    • $122/SF
    • 78 Days On Market

    Last Listing Agent Andrew Beaven Wright Real Estate

    8 N 2nd St, Denton, MD 21629
    • /48

      Est $281,684

      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

  • /44

    $464,000

    Under Contract
    • 5 Beds
    • 3.5 Baths
    • 3,040 Sq Ft

    7 Lister Ln, Ridgely, MD 21660

    Welcome to this Grand Colonial! One of the Largest homes in the neighborhood with a fully finished basement! New Roof 2025 & New HVAC 2024!!!Main level Features an open concept -great room, massive kitchen with sunroon. 10ft ceilings in the main level give this home an amazing flow with bright sunshine from all the windows. Large Kitchen with Lots of storage, 2 pantries, and a Huge Island

    Kathleen Brenton Brenton Realty Group

    7 Lister Ln, Ridgely, MD 21660
  • /12

    $60,027

    Sold Mar 31, 2026

    21269 Dover Bridge Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1996

    Last Sold Summary

    • $45/SF
    • 64 Days On Market

    Last Listing Agent Donna Harrington Coldwell Banker Realty

    21269 Dover Bridge Rd, Preston, MD 21655
    • /9

      Est $105,305

      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

  • /60

    $533,900

    Pending
    • 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
  • /13

    $230,000

    Sold Feb 27, 2026

    1202 Blue Heron Dr, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 1,753 Sq Ft
    • Built 2004

    Last Sold Summary

    • 2% Below List Price
    • $131/SF
    • 46 Days On Market

    Current Estimated Value $230,388

    Last Listing Agent SHANTA PHILLIPS EXP Realty, LLC

    1202 Blue Heron Dr, Denton, MD 21629
    • /11

      Est $286,938

      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

  • /29

    $750,000

    • 3 Beds
    • 2 Baths
    • 4,580 Sq Ft

    14236 Drapers Mill Rd, Greensboro, MD 21639

    STOP, LOOK, and READ...this may be exactly the property you’ve been searching for!! RESIDENTIAL / COMMERCIAL OPPORTUNITY – Zoned C-2, this versatile multi-use property offers endless possibilities! Relocate your business, expand to a second location, or launch your next venture while enjoying the convenience of living and working side by side on this incredible 2+ acre property. This unique

    Karen Clark Clark & Co Realty, LLC

    14236 Drapers Mill Rd, Greensboro, MD 21639
  • /16

    $215,000

    Sold Oct 24, 2025

    522 Lincoln St, Denton, MD 21629

    • 2 Beds
    • 1 Bath
    • 640 Sq Ft
    • Built 1961

    Last Sold Summary

    • $336/SF
    • 10 Days On Market

    Current Estimated Value $206,172

    Last Listing Agent Amanda Morgan Brenton Realty Group

    522 Lincoln St, Denton, MD 21629
    • /20

      Est $245,170

      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

  • /59

    $1,500,000

    Coming Soon
    • 4 Beds
    • 3 Baths
    • 3,358 Sq Ft

    23071 Tuckahoe Springs Dr, Denton, MD 21629

    Beautifully positioned along the deep protected waters of the Tuckahoe, this exceptional residence has been transformed through an extensive renovation that blends timeless design with comfortable waterfront living. Every improvement was carefully planned, resulting in a home that feels as inviting as it is impressive. The heart of the home is the custom kitchen, where blue marble countertops,

    Sydney Johnson Cohee Sharon Real Estate P.C.

    23071 Tuckahoe Springs Dr, Denton, MD 21629
  • /10

    $180,000

    Sold Jan 14, 2026

    245 Briarwood Cir, Denton, MD 21629

    • Studio
    • Built 2010

    Last Sold Summary

    • 392 Days On Market

    Current Estimated Value $199,000

    Last Listing Agent Phil Riordan Meredith Fine Properties

    245 Briarwood Cir, Denton, MD 21629
    • /13

      Est $211,517

      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

  • /31

    $310,000

    • 3 Beds
    • 1.5 Baths
    • 1,234 Sq Ft

    106 Main St, Preston, MD 21655

    Welcome to this charming and spacious home in Preston offering 3 bedrooms, 1.5 bathrooms, and 2,050 square feet of comfortable living space. Freshly painted throughout, this home features beautiful hardwood flooring that adds warmth and timeless character. With generous living areas and a move-in-ready feel, this property blends comfort and style while providing plenty of space for everyday

    Shay Prattis Keller Williams Realty

    106 Main St, Preston, MD 21655
  • /4

    $110,000

    Sold Dec 15, 2025

    0 Whiteleysburg Rd Unit DEKT2042216, Harrington, DE 19952

    • Land
    • 2 Acres
    • $55,000 per Acre

    Last Sold Summary

    • 1 Day On Market

    Last Listing Agent Amy Torbert Diamond State Cooperative LLC

    0 Whiteleysburg Rd Unit DEKT2042216, Harrington, DE 19952
    • /32

      Est $425,820

      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

  • /45

    $459,900

    Open Sat 12PM - 2PM
    • 3 Beds
    • 2.5 Baths
    • 2,839 Sq Ft

    128 Main St, Preston, MD 21655

    Blending warmth, character, and thoughtful updates, this beautifully maintained post-and-beam home offers a truly inviting living experience both inside and out. The spacious main level features all tile flooring, a huge living room anchored by a cozy wood stove, a flexible study/sitting room, and a charming 3-season room. The kitchen and dining combination creates an ideal gathering space with

    Jessica Clark Wilson Realty & Staging LLC

    128 Main St, Preston, MD 21655
  • /19

    $315,000

    Sold Jan 09, 2026

    25607 Garey Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 920 Sq Ft
    • Built 1998

    Last Sold Summary

    • $342/SF
    • 39 Days On Market

    Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

    25607 Garey Rd, Denton, MD 21629

Showing Results 481 - 520, Page 13 of 18

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