15,709

Caroline County, MD Homes

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  • /33

    $362,500

    • 3 Beds
    • 2 Baths
    • 1,575 Sq Ft

    215 Apple Ln, Preston, MD 21655

    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. With spring just around the corner,

    Amy Endzel Keller Williams Select Realtors of Annapolis

    215 Apple Ln, Preston, MD 21655
  • /61

    $429,900 Sold Jan 05, 2026

    26091 Hokum Dr, Greensboro, MD 21639

    • 4 Beds
    • 2.5 Baths
    • 2,248 Sq Ft
    • Built 2004

    Last Sold Summary

    • $191/SF
    • 24 Days On Market

    Current Estimated Value $446,531

    Last Listing Agent Lori Marino Long & Foster Real Estate, Inc.

    26091 Hokum Dr, Greensboro, MD 21639
    • /10

      Est $176,870 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

      • 181% Above List Price
      • $51/SF
      • 18 Days On Market
      • Last Sold Price $63,000
      • Mar 14, 2024

      Last Listing Agent Pamela Geib Long & Foster

  • /37

    $279,000

    • 2 Beds
    • 2 Baths
    • 1,104 Sq Ft

    2697 Choptank Main St, Preston, MD 21655

    Charming Renovated Home in Choptank, Preston MD. This home currently has a fresh coat of interior paint, new kitchen appliances. Luxury vinyl flooring installed in the Living Room. Updated bath vanities and many more updates. It is turn key and ready and waiting for you. Situated on a large double lot with mature landscaping. Don’t miss this beautifully completely renovated 2-bedroom, 2-bath home

    Darlene Wheatley Benson & Mangold, LLC

    2697 Choptank Main St, Preston, MD 21655
  • /43

    $240,000 Sold May 06, 2026

    207 Bloomingdale Ave, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,684 Sq Ft
    • Built 1953

    Last Sold Summary

    • $143/SF
    • 202 Days On Market

    Current Estimated Value $241,814

    Last Listing Agent Dustin Parker The Parker Group

    207 Bloomingdale Ave, Federalsburg, MD 21632
    • /3

      Est $285,282 Not Listed For Sale

      26220 Shore Hwy, Denton, MD 21629

      • 3 Beds
      • 1 Bath
      • 1,104 Sq Ft
      • Built 1977
      26220 Shore Hwy, Denton, MD 21629

      Last Sold Summary

      • 16% Above List Price
      • $222/SF
      • 7 Days On Market
      • Last Sold Price $245,000
      • Jul 19, 2023

      Last Listing Agent Sheila Washburn Benson & Mangold, LLC

  • /10

    $42,999

    • Land
    • 10,454 Sq Ft
    • $179,162 per Acre

    0 Brooklyn Ave, Federalsburg, MD 21632

    Taylor McCartney VRA Realty

    0 Brooklyn Ave, Federalsburg, MD 21632
  • /3

    $27,500 Sold Dec 04, 2025

    222 Denton Rd, Federalsburg, MD 21632

    • Land
    • 10,018 Sq Ft
    • $119,565 per Acre

    Last Sold Summary

    • 589 Days On Market

    Current Estimated Value $33,524

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

    222 Denton Rd, Federalsburg, MD 21632
    • /26

      Est $631,625 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

      • 19% Above List Price
      • $351/SF
      • 301 Days On Market
      • Last Sold Price $530,000
      • Oct 11, 2023

      Last Listing Agent Mickey Hayward Sunset Properties

  • 121 Hobbs St, Greensboro, MD 21639

    $301,990 New Construction

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

    121 Hobbs St, Greensboro, MD 21639

    Come discover 121 Hobbs Street, a new home soon to be 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

    D.R. Horton Builder
    121 Hobbs St, Greensboro, MD 21639
  • /58

    $700,000 Sold Dec 17, 2025

    25211 Adams Landing Rd, Denton, MD 21629

    • 4 Beds
    • 2 Baths
    • 2,273 Sq Ft
    • Built 1960

    Last Sold Summary

    • $308/SF
    • 12 Days On Market

    Current Estimated Value $715,096

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

    25211 Adams Landing Rd, Denton, MD 21629
    • /24

      Est $222,776 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

      • 3% Below List Price
      • $147/SF
      • 13 Days On Market
      • Last Sold Price $230,000
      • Nov 15, 2024

      Last Listing Agent Mark McGuire Benson & Mangold, LLC

  • /19

    $50,000 Pending

    • Land
    • 16,117 Sq Ft
    • $135,135 per Acre

    2 N Main St, Greensboro, MD 21639

    Cleared and ready for your vision! This 1/3+ acre in-town parcel offers the perfect canvas for your new build. Buyer to perform all due diligence with the Town regarding development requirements, including costs for water and sewer allocation.

    Karen Clark Clark & Co Realty, LLC

    2 N Main St, Greensboro, MD 21639
  • /49

    $390,000 Sold Feb 13, 2026

    1111 Ruddy Duck Ct, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,670 Sq Ft
    • Built 2006

    Last Sold Summary

    • $146/SF
    • 13 Days On Market

    Current Estimated Value $387,111

    Last Listing Agent Lee Wolff FSBO Broker

    1111 Ruddy Duck Ct, Denton, MD 21629
    • /59

      Est $295,179 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

      • 7% Above List Price
      • $189/SF
      • 30 Days On Market
      • Last Sold Price $274,990
      • Oct 26, 2023

      Last Listing Agent Angela Demattia BHHS PenFed (actual)

  • /9

    $159,000 Pending

    • 3 Beds
    • 2 Baths
    • 2,776 Sq Ft

    106 S 6th St, Denton, MD 21629

    Charming colonial in the heart of Denton, thoughtfully converted into a two-unit multifamily property. Nestled on a quiet street, this home offers flexible living options with spacious layouts, classic character, and excellent potential for rental income or multigenerational living. A wonderful opportunity to invest or reside in a peaceful in-town setting. Great investment property.

    Amy Betts Coldwell Banker Realty

    106 S 6th St, Denton, MD 21629
  • /5

    $238,000 Sold Sep 24, 2025

    116 Maple Ave, Preston, MD 21655

    • 2 Beds
    • 1.5 Baths
    • 1,458 Sq Ft
    • Built 1915

    Last Sold Summary

    • $163/SF
    • 69 Days On Market

    Current Estimated Value $234,765

    Last Listing Agent Mary Haddaway Benson & Mangold, LLC

    116 Maple Ave, Preston, MD 21655
    • /11

      Est $272,766 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

      • 7% Above List Price
      • $207/SF
      • 52 Days On Market
      • Last Sold Price $255,000
      • Dec 29, 2023

      Last Listing Agent Andrew Beaven Wright Real Estate

  • /16

    $243,000

    • 3 Beds
    • 2.5 Baths
    • 1,693 Sq Ft

    1204 Blue Heron Dr, Denton, MD 21629

    Come on in to explore this beautifully maintained 3-level home offering the perfect blend of modern convenince 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 thoughtfully updated with fresh paint, new appliances and more to ensure it's move-in ready for you.

    Carolyn A. Page Shore Results Realty

    1204 Blue Heron Dr, Denton, MD 21629
  • /34

    $386,000 Sold Jun 27, 2025

    306 Kerr Ave, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,064 Sq Ft
    • Built 2005

    Last Sold Summary

    • $187/SF
    • 48 Days On Market

    Current Estimated Value $410,541

    Last Listing Agent Justin Pokrywka Taylor Properties

    306 Kerr Ave, Denton, MD 21629
    • /30

      Est $461,395 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

      • 5% Below List Price
      • $302/SF
      • 19 Days On Market
      • Last Sold Price $485,000
      • Oct 25, 2024

      Last Listing Agent Bonnie Johnson Keller Williams Realty

  • /89

    $2,750,000 Pending

    • 4 Beds
    • 4.5 Baths
    • 6,520 Sq Ft

    28219 Bridgeville Rd, Federalsburg, MD 21632

    Welcome to a rare opportunity to own a premier 105+/- acre agricultural estate combining modern comfort, income-producing farmland, and outstanding infrastructure. Ideally situated in a peaceful rural setting, this remarkable property features approximately 70± acres of fully irrigated, tillable land—perfect for high-yield row crops or specialty farming. At the heart of the farm sits a stunning

    Jim Corson Benson & Mangold, LLC

    28219 Bridgeville Rd, Federalsburg, MD 21632
  • /8

    $125,100 Sold Jun 12, 2025

    0 Laurel Grove Unit MDCM2004422, Federalsburg, MD 21632

    • Land
    • 9.42 Acres
    • $13,280 per Acre

    Last Sold Summary

    • 291 Days On Market

    Last Listing Agent Diane Wenk Wright Real Estate

    0 Laurel Grove Unit MDCM2004422, Federalsburg, MD 21632
    • /30

      Est $268,092 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

      • 6% Below List Price
      • $213/SF
      • 13 Days On Market
      • Last Sold Price $285,000
      • May 08, 2024

      Last Listing Agent Robert Bringman Long & Foster

  • /14

    $220,000

    • 3 Beds
    • 2.5 Baths
    • 1,560 Sq Ft

    1304 Blue Heron Dr, Denton, MD 21629

    Welcome to 1304 Blue Heron Drive in Denton, Maryland — a move-in ready three-story townhome offering space, style, and comfort. This well-maintained home features LVP flooring throughout the main living area, granite countertops, stainless steel appliances, and a layout designed for everyday living.The spacious bedrooms provide plenty of room to spread out, including a private third-floor

    Heather Brummell Keller Williams Realty

    1304 Blue Heron Dr, Denton, MD 21629
  • /70

    $398,000 Sold Jun 27, 2025

    1110 Osprey Ln, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,650 Sq Ft
    • Built 2005

    Last Sold Summary

    • $150/SF
    • 3 Days On Market

    Current Estimated Value $421,632

    Last Listing Agent Judith Germain Benson & Mangold, LLC

    1110 Osprey Ln, Denton, MD 21629
    • /14

      Est $316,128 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

      • 29% Above List Price
      • $199/SF
      • 5 Days On Market
      • Last Sold Price $245,000
      • Aug 16, 2023

      Last Listing Agent Linda Moore Long & Foster

  • /53

    $199,000 Pending

    • 3 Beds
    • 1.5 Baths
    • 2,817 Sq Ft

    22060 Main St, Hillsboro, MD 21641

    Needs Work. sold as is - large home in need of updating/TLC - 2-story 3 car garage

    Keith Brooks Thurston Wyatt Real Estate, LLC

    22060 Main St, Hillsboro, MD 21641
  • /15

    $265,000 Sold Aug 20, 2025

    3181 Gallagher Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 1990

    Last Sold Summary

    • $237/SF
    • 23 Days On Market

    Current Estimated Value $275,082

    Last Listing Agent Andrew Beaven Wright Real Estate

    3181 Gallagher Rd, Preston, MD 21655
    • /28

      Est $200,341 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

      • 7% Below List Price
      • $267/SF
      • 26 Days On Market
      • Last Sold Price $215,000
      • Dec 24, 2024

      Last Listing Agent Crystal Smith RE/MAX

  • /36

    $289,000

    • 3 Beds
    • 1 Bath
    • 1,392 Sq Ft

    6101 Bethlehem Rd, Preston, MD 21655

    *Please note Mother Nature has blessed this house with baby birds at the entrance, Showings are put off till the 8th of May, this should give the little feather family time to move on. Searching for quiet and private yet close to everything home - you just found it! Three bedroom rancher sits on 1.37 acres overlooking farmland makes this a very special find. Very well maintained and updated house

    Kat Thompson Benson & Mangold, LLC.

    6101 Bethlehem Rd, 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
    • /7

      Est $197,094 Not Listed For Sale

      3477 Holland Dr, Federalsburg, MD 21632

      • 3 Beds
      • 1 Bath
      • 1,164 Sq Ft
      • Built 1994
      3477 Holland Dr, Federalsburg, MD 21632

      Last Sold Summary

      • 13% Above List Price
      • $150/SF
      • 150 Days On Market
      • Last Sold Price $175,000
      • Jun 03, 2024

      Last Listing Agent KL Harris Keller Williams Select Realtors of Cambridge

  • /12

    $299,900

    • 3 Beds
    • 1 Bath
    • 1,024 Sq Ft

    5 7th St, Ridgely, MD 21660

    Don't wait to tour this wonderfully renovated home in the Greenridge community! Lots to love from top to bottom. Completely rehabbed with Hickory Vinyl Plank flooring throughout and all freshly painted. New stainless steel appliances in the spacious kitchen with center island and lots of cabinet and working space plus a full pantry. All new beautiful bathroom with rain shower head. A laundry room

    Marcia Rostien Long & Foster Real Estate, Inc.

    5 7th St, Ridgely, MD 21660
  • /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 $75,453

    Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

    205 New St, Goldsboro, MD 21636
    • /12

      Est $228,276 Not Listed For Sale

      627 Camp Rd, Denton, MD 21629

      • 2 Beds
      • 1 Bath
      • 816 Sq Ft
      • Built 1955
      627 Camp Rd, Denton, MD 21629

      Last Sold Summary

      • 4% Above List Price
      • $270/SF
      • 25 Days On Market
      • Last Sold Price $220,000
      • Jan 17, 2024

      Last Listing Agent Linda Moore Long & Foster

  • /39

    $399,900

    • 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
  • /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 $360,023

    Last Listing Agent Jarnell Foster Benson & Mangold, LLC

    15 Ridgeway Dr, Ridgely, MD 21660
    • /77

      Est $470,517 Not Listed For Sale

      22959 Lyn Oaks Dr, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,904 Sq Ft
      • Built 2005
      22959 Lyn Oaks Dr, Preston, MD 21655

      Last Sold Summary

      • 2% Above List Price
      • $242/SF
      • 11 Days On Market
      • Last Sold Price $460,000
      • Jul 26, 2024

      Last Listing Agent Debbie Lipscomb Benson & Mangold, LLC

  • /40

    $235,000

    • 5 Beds
    • 3 Baths
    • 2,122 Sq Ft

    212 Main St, Preston, MD 21655

    Welcome to this spacious and beautifully maintained property nestled in the peaceful town of Preston. The main residence features 5 generously sized bedrooms and 3 full bathrooms, offering plenty of space for comfortable family living, guests, or multi-generational arrangements. At the heart of the home, you’ll find a large eat-in kitchen, perfect for gathering with family, hosting friends, or

    Ross Muir EXP Realty, LLC

    212 Main St, Preston, MD 21655

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