15,577

Caroline County, MD Homes

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  • /127

    $2,560,000

    Sold Jun 04, 2026

    4218 Harmony Rd, Preston, MD 21655

    • 8 Beds
    • 16 Baths
    • 9,364 Sq Ft
    • Built 2004

    Last Sold Summary

    • $273/SF
    • 136 Days On Market

    Current Estimated Value $2,695,817

    Last Listing Agent Donna Harrington Coldwell Banker Realty

    4218 Harmony Rd, Preston, MD 21655
    • /19

      Est $402,994

      Not Listed For Sale

      11458 Reed Cir, Ridgely, MD 21660

      • 3 Beds
      • 2 Baths
      • 1,440 Sq Ft
      • Built 1993
      11458 Reed Cir, Ridgely, MD 21660

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Chris Rosendale CR Realty

  • /55

    $309,000

    • 2 Beds
    • 1 Bath
    • 1,284 Sq Ft

    2766 Veterans Dr, Federalsburg, MD 21632

    Across from the boat ramp and water view of 3 ponds on the property! Outdoor enthusiasts, nature lovers, and adventure seekers — welcome to your dream retreat. This one‑of‑a‑kind property offers an extraordinary blend of privacy, recreation, and natural beauty that is nearly impossible to find elsewhere. Set on gently rolling terrain overlooking multiple deep‑water ponds, this property delivers

    Stacie Luhrman Benson & Mangold, LLC

    2766 Veterans Dr, Federalsburg, MD 21632
  • /80

    $804,000

    Sold Nov 26, 2025

    15551 Wharton Rd, Goldsboro, MD 21636

    • 3 Beds
    • 2 Baths
    • 2,160 Sq Ft
    • Built 1850

    Last Sold Summary

    • $372/SF
    • 40 Days On Market

    Current Estimated Value $797,258

    Last Listing Agent Heather Branham The Parker Group

    15551 Wharton Rd, Goldsboro, MD 21636
    • /42

      Est $457,126

      Not Listed For Sale

      23 Lister Ln, Ridgely, MD 21660

      • 5 Beds
      • 4.5 Baths
      • 3,441 Sq Ft
      • Built 2005
      23 Lister Ln, Ridgely, MD 21660

      Last Sold Summary

      • 59 Days On Market

      Last Listing Agent Diane Donnelly Keller Williams Flagship

  • /11

    $199,900

    $70K PRICE DROP
    • Land
    • 14.71 Acres
    • $13,589 per Acre

    0 Trunk Rd Unit MDCM2007270, Henderson, MD 21640

    Discover the possibilities on this 14.71± acre wooded parcel on Trunk Line Rd in Henderson, MD, now offered at $224,900. Perc approved for a conventional septic system serving a 4+ bedroom dwelling, this property offers the opportunity to build a custom home while enjoying the privacy and space of a rural setting.With approximately 466 feet of road frontage along Trunk Line Road and a

    Heather Branham The Parker Group

    0 Trunk Rd Unit MDCM2007270, Henderson, MD 21640
  • /2

    $750,000

    Sold Jul 31, 2026

    12136 Holly Rd, Ridgely, MD 21660

    • 4 Beds
    • 3 Baths
    • 2,432 Sq Ft
    • Built 2005

    Last Sold Summary

    • $308/SF
    • 3 Days On Market

    Current Estimated Value $731,919

    Last Listing Agent Donna Harrington Coldwell Banker Realty

    12136 Holly Rd, Ridgely, MD 21660
    • /15

      Est $62,179

      Not Listed For Sale

      27515 Anthony Mill Rd, Denton, MD 21629

      27515 Anthony Mill Rd, Denton, MD 21629

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Gretchen Wichlinski Compass

  • /2

    $299,990

    New Construction $2K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft

    121 Hobbs St, Greensboro, MD 21639

    Come discover 121 Hobbs Street, a new home under construction in the quaint Kinnamon Meadows community of 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

    D.R. Horton Builder
    121 Hobbs St, Greensboro, MD 21639
  • /19

    $340,000

    Sold Dec 05, 2025

    314 Kerr Ave, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,764 Sq Ft
    • Built 1984

    Last Sold Summary

    • $193/SF
    • 4 Days On Market

    Current Estimated Value $354,570

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

    314 Kerr Ave, Denton, MD 21629
    • /15

      Est $358,626

      Not Listed For Sale

      304 Kerr Ave, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,808 Sq Ft
      • Built 2005
      304 Kerr Ave, Denton, MD 21629

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Linda Moore Long & Foster Real Estate, Inc.

  • /16

    $230,000

    $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,693 Sq Ft

    1204 Blue Heron Dr, Denton, MD 21629

    ***NEWLY ADJUSTED PRICE***Come on in to explore this beautifully maintained 3-level home offering the perfect blend of modern convenience and comfortable living. This beauty features 3 spacious bedrooms and 2.5 baths, with an open floor plan that creates an inviting flow throughout the main living areas. The home has been updated with fresh paint, new appliances and more to ensure it's move-in

    Carolyn A. Page Shore Results Realty

    1204 Blue Heron Dr, Denton, MD 21629
  • /46

    $365,000

    Sold Jan 27, 2026

    8548 Dogwood Blossom Ln, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,176 Sq Ft
    • Built 1988

    Last Sold Summary

    • $168/SF
    • 63 Days On Market

    Current Estimated Value $377,510

    Last Listing Agent Kathleen Brenton Brenton Realty Group

    8548 Dogwood Blossom Ln, Denton, MD 21629
    • /65

      Est $455,432

      Not Listed For Sale

      135 Walnut St, Ridgely, MD 21660

      • 4 Beds
      • 4 Baths
      • 3,408 Sq Ft
      • Built 2005
      135 Walnut St, Ridgely, MD 21660

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

  • /39

    $309,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 1,936 Sq Ft

    245 Briarwood Cir, Denton, MD 21629

    Remarkable Move in Ready Townhome Beautifully designed new construction interior townhome located in an established community in the heart of Denton, Maryland! Offering 4 spacious bedrooms, 2.5 baths, and an oversized rear-load garage, this home combines modern style with everyday functionality.The open-concept floor plan is perfect for both entertaining and daily living, featuring a

    Michelle DiDonato Island Realty, LLC

    245 Briarwood Cir, Denton, MD 21629
  • /16

    $249,375

    Sold Aug 27, 2026

    11502 Greensboro Rd, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,892 Sq Ft
    • Built 1990

    Last Sold Summary

    • 27% Below List Price
    • $132/SF
    • 77 Days On Market

    Current Estimated Value $320,602

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

    11502 Greensboro Rd, Greensboro, MD 21639
    • /34

      Est $398,616

      Not Listed For Sale

      306 Kerr Ave, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,064 Sq Ft
      • Built 2005
      306 Kerr Ave, Denton, MD 21629

      Last Sold Summary

      • 48 Days On Market

      Last Listing Agent Justin Pokrywka Taylor Properties

  • /37

    $385,000

    • 4 Beds
    • 2 Baths
    • 1,728 Sq Ft

    5716 Bethlehem Rd, Preston, MD 21655

    Space, flexibility and over an acre to call your own — welcome to 5716 Bethlehem Road! Set on 1.14 acres in Preston, this spacious one-level home offers 4 bedrooms, 2 full bathrooms, a separate den/flex room and a floor plan with room to spread out.Step inside and you'll find bright, generously sized living spaces and plenty of possibilities. The owner's suite is tucked away with its own

    Catelin Schwarz NextHome Envision

    5716 Bethlehem Rd, Preston, MD 21655
  • /6

    $346,147

    Sold Aug 10, 2026

    27279 Jenny Hye Ln, Marydel, MD 21649

    • 3 Beds
    • 2.5 Baths
    • 2,286 Sq Ft
    • Built 1979

    Last Sold Summary

    • 8% Below List Price
    • $151/SF
    • 335 Days On Market

    Current Estimated Value $341,521

    Last Listing Agent Hudson Post Keller Williams Select Realtors of Easton

    27279 Jenny Hye Ln, Marydel, MD 21649
    • /31

      Est $266,444

      Not Listed For Sale

      123 Bloomingdale Ave, Federalsburg, MD 21632

      • 3 Beds
      • 1.5 Baths
      • 1,584 Sq Ft
      • Built 1900
      123 Bloomingdale Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 369 Days On Market

      Last Listing Agent Marla Baines Meredith Fine Properties

  • /39

    $384,900

    $35K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,159 Sq Ft

    25331 Adams Landing Rd, Denton, MD 21629

    2 Acre cleared lot. Great opportunity for a fixer upper. Home needs a fair amount of work but it has a great layout. Main level primary, office/den separate dining room. Additional main level bedroom and full bath on main level. Spacious living room with access to the large screened porch. Corner eat-in kitchen & main level laundry. Cash or 203(K).***The property is being sold in its current

    Lisa Whited Keller Williams Realty

    25331 Adams Landing Rd, Denton, MD 21629
  • /2

    $276,990

    Sold Oct 17, 2025

    115 Parkland Rd, Greensboro, MD 21639

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

    Last Sold Summary

    • $234/SF
    • 22 Days On Market

    Last Listing Agent Justin Wood D.R. Horton Realty of Virginia, LLC

    115 Parkland Rd, Greensboro, MD 21639
    • /15

      Est $223,329

      Not Listed For Sale

      22081 Dover Bridge Rd, Preston, MD 21655

      • 3 Beds
      • 1 Bath
      • 1,252 Sq Ft
      • Built 1954
      22081 Dover Bridge Rd, Preston, MD 21655

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Pamela Price Berkshire Hathaway HomeServices PenFed Realty

  • /66

    $995,000

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

    5315 Smithville Rd, Federalsburg, MD 21632

    Nestled in a farm like setting, this exquisite ranch-style home offers a luxurious lifestyle on a sprawling 40.64+/-acre lot, seamlessly blending elegance with nature. The property boasts modern comforts throughout its 1,568+/- sq. ft. of meticulously designed space. Step inside to discover an inviting interior adorned with rich hardwood and plush carpet flooring. The traditional floor plan

    Bill Wieland Benson & Mangold, LLC

    5315 Smithville Rd, Federalsburg, MD 21632
  • /35

    $335,000

    Sold Feb 06, 2026

    206 Charles St, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 1,734 Sq Ft
    • Built 1995

    Last Sold Summary

    • $193/SF
    • 64 Days On Market

    Current Estimated Value $339,670

    Last Listing Agent Rosezette Dennis Coldwell Banker Realty

    206 Charles St, Federalsburg, MD 21632
    • /52

      Est $504,711

      Not Listed For Sale

      5569 Harmony Woods Dr, Preston, MD 21655

      • 4 Beds
      • 2.5 Baths
      • 2,909 Sq Ft
      • Built 2005
      5569 Harmony Woods Dr, Preston, MD 21655

      Last Sold Summary

      • 185 Days On Market

      Last Listing Agent Erin Anderson Chesapeake Real Estate Associates, LLC

  • /24

    $249,900

    Under Contract
    • 3 Beds
    • 1 Bath
    • 1,359 Sq Ft

    315 S Main St, Greensboro, MD 21639

    Charming Greensboro bungalow ready to welcome you home! This 3-bedroom, 1-bathroom property offers a warm blend of character and modern updates throughout. The dining area features a beautiful wood‑burning fireplace, creating a cozy focal point for gatherings. The remodeled 2024 kitchen brings fresh style and functionality, while the new roof (2019) and all‑new flooring add peace of mind and

    Amanda Morgan Brenton Realty Group

    315 S Main St, Greensboro, MD 21639
  • /45

    $442,675

    Sold Jul 17, 2026

    22408 Hog Creek Rd, Preston, MD 21655

    • 3 Beds
    • 3.5 Baths
    • 2,667 Sq Ft
    • Built 2004

    Last Sold Summary

    • 11% Below List Price
    • $166/SF
    • 89 Days On Market

    Current Estimated Value $441,692

    Last Listing Agent James Bent Benson & Mangold, LLC

    22408 Hog Creek Rd, Preston, MD 21655
    • /47

      Est $494,610

      Not Listed For Sale

      5577 Harmony Woods Dr, Preston, MD 21655

      • 3 Beds
      • 2.5 Baths
      • 2,526 Sq Ft
      • Built 2006
      5577 Harmony Woods Dr, Preston, MD 21655

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Ed Quidas Long & Foster Real Estate, Inc.

  • /29

    $409,500

    New Construction Under Contract
    • 4 Beds
    • 2 Baths
    • 1,628 Sq Ft

    5 Sunrise Ave, Ridgely, MD 21660

    Welcome to 5 Sunrise Avenue, a beautifully crafted Lomaxx Custom Homes rancher that’s complete and move in ready! This thoughtfully designed home offers 4 bedrooms, 2 bathrooms, and a spacious 2-car garage, blending modern style with everyday comfort.Inside, you’ll find an open layout featuring luxury vinyl plank flooring, quartz countertops, stainless steel appliances, tile showers, and

    Crystal Smith RE/MAX Executive

    5 Sunrise Ave, Ridgely, MD 21660
  • /102

    $1,200,000

    Sold Jul 02, 2026

    23296 Wilder Way, Denton, MD 21629

    • 4 Beds
    • 3.5 Baths
    • 3,356 Sq Ft
    • Built 2019

    Last Sold Summary

    • 14% Below List Price
    • $358/SF
    • 131 Days On Market

    Current Estimated Value $1,240,069

    Last Listing Agent Brian Gearhart Benson & Mangold, LLC

    23296 Wilder Way, Denton, MD 21629
    • /70

      Est $504,352

      Not Listed For Sale

      23792 Bridgetown Rd, Henderson, MD 21640

      • 3 Beds
      • 3.5 Baths
      • 2,375 Sq Ft
      • Built 1987
      23792 Bridgetown Rd, Henderson, MD 21640

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Chris Rosendale CR Realty

  • /2

    $298,990

    New Construction
    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft

    Helena Plan at Kinnamon Meadows, Greensboro, MD 21639

    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. The oversized great room with an abundance of natural light is open to the kitchen making an ideal space to entertain or

    D.R. Horton Builder
    103 Park Ave Unit 36203274, Greensboro, MD 21639
  • /25

    $82,000

    Sold Jul 21, 2026

    28035 Possum Hill Rd, Federalsburg, MD 21632

    • 4 Beds
    • 30 Baths
    • 1,428 Sq Ft
    • Built 1990

    Last Sold Summary

    • $57/SF
    • 888 Days On Market

    Current Estimated Value $161,440

    Last Listing Agent Sam Benkirane Proplocate Realty, LLC

    28035 Possum Hill Rd, Federalsburg, MD 21632
    • /58

      Est $364,178

      Not Listed For Sale

      510 Pintail St, Greensboro, MD 21639

      • 5 Beds
      • 2.5 Baths
      • 1,984 Sq Ft
      • Built 2005
      510 Pintail St, Greensboro, MD 21639

      Last Sold Summary

      • 91 Days On Market

      Last Listing Agent Jonathan Fleming Weichert Realtors - Blue Ribbon

  • /36

    $425,000

    $20K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,492 Sq Ft

    1709 Cattail Commons Way, Denton, MD 21629

    Welcome to 1709 Cattail Commons Way, located in the highly desirable Savannah Overlook community in Denton, MD. This beautifully maintained 4-bedroom, 2.5-bath home offers a spacious open floor plan, modern upgrades, and move-in ready convenience—perfect for today’s buyer seeking comfort, functionality, and style.The main level features a bright and open layout ideal for both everyday

    Kaitlyn Collins Benson & Mangold, LLC

    1709 Cattail Commons Way, Denton, MD 21629
  • /2

    $53,000

    Sold Mar 16, 2026

    307 Buena Vista Ave, Federalsburg, MD 21632

    • Land
    • 1.75 Acres
    • $30,286 per Acre

    Last Sold Summary

    • 18% Below List Price
    • 18 Days On Market

    Current Estimated Value $53,444

    Last Listing Agent Heather Brummell Keller Williams Realty

    307 Buena Vista Ave, Federalsburg, MD 21632
    • /15

      Est $327,293

      Not Listed For Sale

      1311 Fairfield Ct, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 1,360 Sq Ft
      • Built 2003
      1311 Fairfield Ct, Denton, MD 21629

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Chad Robertson Compass

  • /2

    $375,000

    Coming Soon Oct 16
    • 3 Beds
    • 2.5 Baths
    • 1,736 Sq Ft

    107 Sunset Blvd, Preston, MD 21655

    Welcome to 107 Sunset Blvd in Preston, MD! This spacious 3-bedroom, 2.5-bath brick home offers comfortable living, thoughtful updates, and everyday convenience. The inviting interior features an open living and dining area with plenty of room to gather, entertain, and make yourself at home. Newer LVP flooring, fresh paint, and upgraded recessed lighting create a clean, modern feel throughout the

    Beverly Brown Coldwell Banker Realty

    107 Sunset Blvd, Preston, MD 21655
  • /42

    $465,000

    Sold Mar 30, 2026

    24749 Woods Dr, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,550 Sq Ft
    • Built 2000

    Last Sold Summary

    • 4% Below List Price
    • $182/SF
    • 80 Days On Market

    Current Estimated Value $463,990

    Last Listing Agent Peter Stark Benson & Mangold, LLC

    24749 Woods Dr, Denton, MD 21629

Showing Results 561 - 600, Page 15 of 18

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