15,625

Caroline County, MD Homes

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    • /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.

  • /34

    $349,000

    $20K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,575 Sq Ft

    215 Apple Ln, Preston, MD 21655

    *Back Up Offers Will Be Considered*Welcome to this beautiful 3-bedroom, 2-bathroom home filled with wonderful updates throughout. As you arrive, you’ll immediately notice the brand-new roof, offering peace of mind for years to come. Step inside to discover a stunning updated kitchen featuring quartz countertops and stainless steel appliances, perfect for both everyday living and entertaining.

    Amy Endzel Keller Williams Select Realtors of Annapolis

    215 Apple Ln, Preston, MD 21655
  • /2

    $269,950

    Sold Jan 23, 2026

    123 Parkland Rd, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft
    • Built 2025

    Last Sold Summary

    • $228/SF
    • 85 Days On Market

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

    123 Parkland Rd, Greensboro, MD 21639
    • /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

    $299,990

    New Construction $8K PRICE DROP Pending
    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft

    111 Hobbs St, Greensboro, MD 21639

    **Red Tag Sales Event through August 2, 2026! Was $307,490 Now: $299,990!** Explore 111 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

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

    111 Hobbs St, Greensboro, MD 21639
  • /7

    $55,000

    Sold Mar 20, 2026

    205 New St, Goldsboro, MD 21636

    • Land
    • 25,264 Sq Ft
    • $94,828 per Acre

    Last Sold Summary

    • 2 Days On Market

    Current Estimated Value $56,127

    Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

    205 New St, Goldsboro, MD 21636
    • /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 Jon Fleming Weichert Realtors - Blue Ribbon

  • /42

    $350,000

    Pending
    • 4 Beds
    • 1.5 Baths
    • 2,276 Sq Ft

    22040 Main St, Hillsboro, MD 21641

    OFFER DEADLINE- please submit all highest and best offers by 5:30 pm on 8/4. Welcome to this stunning Victorian gem built in 1900, gracefully resting on three combined lots totaling .76 acres of mature, beautifully planted grounds. From the moment you arrive, the home's presence is unmistakable; a sweeping wrap-around front porch invites you in, while a fully enclosed back porch offers a quiet

    Kathleen Moore Engel & Völkers Annapolis

    22040 Main St, Hillsboro, MD 21641
  • /30

    $354,900

    Sold Sep 12, 2025

    15 Ridgeway Dr, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • Built 2009

    Last Sold Summary

    • $228/SF
    • 53 Days On Market

    Current Estimated Value $355,173

    Last Listing Agent Jarnell Foster Samson Properties

    15 Ridgeway Dr, Ridgely, MD 21660
    • /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

  • /11

    $224,900

    $45K PRICE DROP
    • Land
    • 14.71 Acres
    • $15,289 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 designated

    Heather Branham The Parker Group

    0 Trunk Rd Unit MDCM2007270, Henderson, MD 21640
  • /12

    $160,000

    Sold Apr 07, 2026

    2578 Hilltop Rd, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,992 Sq Ft
    • Built 1977

    Last Sold Summary

    • $80/SF
    • 4 Days On Market

    Current Estimated Value $211,135

    Last Listing Agent Heather Brummell Keller Williams Realty

    2578 Hilltop Rd, Federalsburg, MD 21632
    • /62

      Est $743,374

      Not Listed For Sale

      23079 Tuckahoe Springs Dr, Denton, MD 21629

      • 3 Beds
      • 4 Baths
      • 3,737 Sq Ft
      • Built 1974
      23079 Tuckahoe Springs Dr, Denton, MD 21629

      Last Sold Summary

      • 112 Days On Market

      Last Listing Agent Melanie Hopkins Coldwell Banker Chesapeake Real Estate Company

  • /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 home.

    D.R. Horton Builder
    121 Hobbs St, Greensboro, MD 21639
  • /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 $2,923,357

    Last Listing Agent Donna Harrington Coldwell Banker Realty

    4218 Harmony Rd, Preston, MD 21655
    • /10

      Est $190,021

      Not Listed For Sale

      208 N Academy St, Greensboro, MD 21639

      • 2 Beds
      • 1 Bath
      • 1,236 Sq Ft
      • Built 1925
      208 N Academy St, Greensboro, MD 21639

      Last Sold Summary

      • 18 Days On Market

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

  • /16

    $235,000

    $15K 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
  • /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
    • /26

      Est $621,637

      Not Listed For Sale

      6105 Laurel Grove Rd, Denton, MD 21629

      • 4 Beds
      • 2 Baths
      • 1,512 Sq Ft
      • Built 1988
      6105 Laurel Grove Rd, Denton, MD 21629

      Last Sold Summary

      • 301 Days On Market

      Last Listing Agent Mickey Hayward Sunset Properties

  • /10

    $309,900

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

    245 Briarwood Cir, Denton, MD 21629

    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 gourmet kitchen with quartz countertops, a

    Michelle DiDonato Island Realty, LLC

    245 Briarwood Cir, Denton, MD 21629
  • /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
    • /24

      Est $240,502

      Not Listed For Sale

      1706 Blue Heron Dr, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 1,560 Sq Ft
      • Built 2005
      1706 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Mark McGuire Benson & Mangold, LLC

  • /39

    $399,900

    $20K 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
  • /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
    • /59

      Est $313,809

      Not Listed For Sale

      403 Mallard Dr, Greensboro, MD 21639

      • 3 Beds
      • 2.5 Baths
      • 1,456 Sq Ft
      • Built 2005
      403 Mallard Dr, Greensboro, MD 21639

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Angela Demattia Berkshire Hathaway HomeServices PenFed Realty

  • /23

    $289,990

    New Construction $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,219 Sq Ft

    109 Hobbs St, Greensboro, MD 21639

    Welcome to 109 Hobbs Street where a new home can be yours in Kinnamon Meadows in Greensboro, MD. This home is not currently under construction. 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

    D.R. Horton Builder
    109 Hobbs St, Greensboro, MD 21639
  • /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
    • /11

      Est $292,446

      Not Listed For Sale

      112 Carolin Ct, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 1977
      112 Carolin Ct, Preston, MD 21655

      Last Sold Summary

      • 52 Days On Market

      Last Listing Agent Andrew Beaven Wright Real Estate

  • /41

    $385,000

    $4K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,138 Sq Ft

    1111 Trice Meadows Cir, Denton, MD 21629

    ****PRICE ADJUSTMENT****Discover your dream home in the highly sought-after Trice Meadows community! This delightful 4-bedroom, 2-bathroom detached single-family home perfectly combines comfort, style, and modern convenience. Its open and inviting floor plan is designed for both day-to-day living and entertaining, making it an ideal choice for families and social gatherings alike. Experience

    LaTanya Drayton United Real Estate Premier

    1111 Trice Meadows Cir, Denton, MD 21629
  • /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
    • /30

      Est $478,256

      Not Listed For Sale

      25778 Herring Ln, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,608 Sq Ft
      • Built 1989
      25778 Herring Ln, Denton, MD 21629

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Bonnie Johnson Keller Williams Realty

  • /29

    $409,500

    New Construction
    • 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 quality

    Crystal Smith RE/MAX Executive

    5 Sunrise Ave, Ridgely, MD 21660
  • /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
    • /30

      Est $283,057

      Not Listed For Sale

      429 N 6th St, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,336 Sq Ft
      • Built 1890
      429 N 6th St, Denton, MD 21629

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Robert Bringman Long & Foster Real Estate, Inc.

  • /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
  • /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
    • /14

      Est $316,164

      Not Listed For Sale

      24352 Robins Creek Rd, Preston, MD 21655

      • 3 Beds
      • 1.5 Baths
      • 1,232 Sq Ft
      • Built 1979
      24352 Robins Creek Rd, Preston, MD 21655

      Last Sold Summary

      • 5 Days On Market

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

  • /36

    $430,000

    $15K 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 living and

    Kaitlyn Collins Benson & Mangold, LLC

    1709 Cattail Commons Way, Denton, MD 21629
  • /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
    • /28

      Est $204,748

      Not Listed For Sale

      1020 Market St, Denton, MD 21629

      • 2 Beds
      • 1 Bath
      • 806 Sq Ft
      • Built 1940
      1020 Market St, Denton, MD 21629

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Crystal Smith RE/MAX Executive

Showing Results 561 - 600, Page 15 of 18

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