15,698

Caroline County, MD Homes

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    • /60

      Est $840,164 Not Listed For Sale

      24461 Friendship Rd, Preston, MD 21655

      • 4 Beds
      • 5 Baths
      • 4,546 Sq Ft
      • Built 2002
      24461 Friendship Rd, Preston, MD 21655

      Last Sold Summary

      • 14% Above List Price
      • $162/SF
      • 16 Days On Market

      Last Sold Price $735,000

      Last Listing Agent Laura Anderson Coldwell Banker (NRT-Southeast-MidAtlantic)

  • /19

    $50,000

    • Land
    • 0.37 Acre
    • $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
  • /41

    $300,000 Sold Apr 11, 2025

    118 Edenton Ln, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,479 Sq Ft
    • Built 1975

    Last Sold Summary

    • $203/SF
    • 113 Days On Market

    Current Estimated Value $309,104

    Last Listing Agent Nishta Gupta Samson Properties

    118 Edenton Ln, Denton, MD 21629
    • /11

      Est $281,865 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

      • 2% Above List Price
      • $260/SF
      • 62 Days On Market

      Last Sold Price $275,000

      Last Listing Agent Bonnie Duley Long & Foster

  • /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

    $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
    • /20

      Est $243,099 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

      • 7% Below List Price
      • $191/SF
      • 115 Days On Market

      Last Sold Price $260,000

      Last Listing Agent Kat Thompson Benson & Mangold, LLC.

  • /16

    $245,000

    • 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
  • 113 Parkland Rd, Greensboro, MD 21639

    $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
    • /13

      Est $197,719 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

      • 4% Above List Price
      • $189/SF
      • 7 Days On Market

      Last Sold Price $190,000

      Last Listing Agent Kat Thompson Benson & Mangold, LLC.

  • /89

    $2,750,000

    • 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
  • /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 $256,706

    Last Listing Agent Ralph Harvey ListWithFreedom.com

    1904 Blue Heron Dr, Denton, MD 21629
    • /32

      Est $439,098 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

      • 10% Above List Price
      • $141/SF
      • 56 Days On Market

      Last Sold Price $400,000

      Last Listing Agent Richard Pullin Weichert Corporate

  • /51

    $325,000 Pending

    • 4 Beds
    • 2 Baths
    • 1,326 Sq Ft

    1203 Tuckahoe Ct, Denton, MD 21629

    Charming 4 bedroom, 2 bath cottage tucked away on a quiet cul-de-sac just minutes from downtown Denton. The first floor features a welcoming living room with LVP flooring, kitchen with updated appliances, two bedrooms, and a full bath. Upstairs, you’ll find two additional bedrooms and a second full bath, offering flexible living space. Outside enjoy a large, fenced-in backyard with a deck and

    Alicia Gannon Dulin Benson & Mangold, LLC

    1203 Tuckahoe Ct, 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 $270,888

    Last Listing Agent Wanda Hampton Clark & Co Realty, LLC

    306 Sunrise Ave, Ridgely, MD 21660
    • /61

      Est $425,201 Not Listed For Sale

      1107 Ruddy Duck Ct, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,914 Sq Ft
      • Built 2006
      1107 Ruddy Duck Ct, Denton, MD 21629

      Last Sold Summary

      • 1% Above List Price
      • $144/SF
      • 7 Days On Market

      Last Sold Price $420,000

      Last Listing Agent Andrea Geppi Coldwell Banker Realty

  • /53

    $225,000

    • 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
  • /20

    $344,000 Sold Apr 30, 2025

    5734 Bell Creek Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 2001

    Last Sold Summary

    • $279/SF
    • 4 Days On Market

    Current Estimated Value $361,834

    Last Listing Agent Katie Moore Coldwell Banker Chesapeake Real Estate Company

    5734 Bell Creek Rd, Preston, MD 21655
    • /19

      Est $329,749 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

      • 5% Above List Price
      • $213/SF
      • 2 Days On Market

      Last Sold Price $315,000

      Last Listing Agent Heather Brummell Keller Williams Realty

  • /128

    $1,295,000 Under Contract

    • 4 Beds
    • 3.5 Baths
    • 4,496 Sq Ft

    24800 Pealiquor Rd, Denton, MD 21629

    Experience timeless elegance and Eastern Shore charm at this beautifully restored 4-bedroom, 3.5-bath colonial retreat set on 7 acres along the Choptank River. Once known as “Hazelwood,” this historic Governor’s Mansion is one you don’t want to miss! Inside, you’ll find expansive formal and informal rooms flow seamlessly for entertaining and family living alike. This estate features refinished

    Christina Ginn Fathom Realty LLC

    24800 Pealiquor Rd, Denton, MD 21629
  • /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
    • /18

      Est $383,831 Not Listed For Sale

      312 Hughlett St, Preston, MD 21655

      • 4 Beds
      • 2.5 Baths
      • 2,130 Sq Ft
      • Built 2005
      312 Hughlett St, Preston, MD 21655

      Last Sold Summary

      • 22% Above List Price
      • $148/SF
      • 57 Days On Market

      Last Sold Price $315,000

      Last Listing Agent Chuck Mangold Benson & Mangold, LLC

  • /7

    $145,000 Under Contract

    • 2 Beds
    • 1 Bath
    • 504 Sq Ft

    305 Maple Ave, Ridgely, MD 21660

    This cozy cottage, situated on a quiet alley, would be perfect for an individual or a young couple. Enjoy your morning coffee on the screened porch. Fenced backyard with a garden shed.

    Andrew Beaven Wright Real Estate

    305 Maple Ave, Ridgely, MD 21660
  • /42

    $337,500 Sold Apr 16, 2025

    12041 Crouse Mill Rd, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,978 Sq Ft
    • Built 1994

    Last Sold Summary

    • $171/SF
    • 18 Days On Market

    Current Estimated Value $358,253

    Last Listing Agent Justin Brewer Baltimore Realty, LLC

    12041 Crouse Mill Rd, Ridgely, MD 21660
    • /54

      Est $462,917 Not Listed For Sale

      3 Robins Ct, Ridgely, MD 21660

      • 4 Beds
      • 2.5 Baths
      • 3,898 Sq Ft
      • Built 2006
      3 Robins Ct, Ridgely, MD 21660

      Last Sold Summary

      • 19% Above List Price
      • $100/SF
      • 71 Days On Market

      Last Sold Price $390,000

      Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

  • /51

    $619,000 Pending

    • 4 Beds
    • 4 Baths
    • 3,484 Sq Ft

    24324 Asbury Dr, Denton, MD 21629

    Lovely grand colonial with covered front porch located on almost 4 acres. The first floor offers a huge primary suite with walk in closet and bath with soaking tub, dual headed shower and double vanity.Dining room has gleaming hardwood floors with enough space to seat 20 people, lovely overhead chandelier and warming propane fireplace . Kitchen has all stainless appliances, plenty of

    Bonnie Johnson Keller Williams Realty

    24324 Asbury Dr, Denton, MD 21629
  • /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 $207,276

    Last Listing Agent Amanda Morgan Brenton Realty Group

    522 Lincoln St, Denton, MD 21629
    • /10

      Est $135,981 Not Listed For Sale

      112 Vernon Ave, Federalsburg, MD 21632

      • 2 Beds
      • 2 Baths
      • 884 Sq Ft
      • Built 1938
      112 Vernon Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 18% Above List Price
      • $130/SF
      • 7 Days On Market

      Last Sold Price $115,000

      Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

  • /39

    $419,900

    • 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
  • /38

    $355,000 Sold Jun 06, 2025

    508 Teal Cir, Greensboro, MD 21639

    • 3 Beds
    • 2.5 Baths
    • 1,952 Sq Ft
    • Built 2004

    Last Sold Summary

    • $182/SF
    • 10 Days On Market

    Current Estimated Value $369,198

    Last Listing Agent Karen Clark Clark & Co Realty, LLC

    508 Teal Cir, Greensboro, MD 21639
    • /24

      Est $217,724 Not Listed For Sale

      108 Liberty Rd, Federalsburg, MD 21632

      • 3 Beds
      • 1.5 Baths
      • 1,756 Sq Ft
      • Built 1890
      108 Liberty Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 6% Above List Price
      • $117/SF
      • 177 Days On Market

      Last Sold Price $204,900

      Last Listing Agent Carolina Mosquera Weichert Corporate

  • /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
  • /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 $193,617

    Last Listing Agent Phil Riordan Meredith Fine Properties

    245 Briarwood Cir, Denton, MD 21629
    • /11

      Est $296,777 Not Listed For Sale

      505 S 2nd St, Denton, MD 21629

      • 3 Beds
      • 1.5 Baths
      • 2,058 Sq Ft
      • Built 1941
      505 S 2nd St, Denton, MD 21629

      Last Sold Summary

      • 7% Above List Price
      • $135/SF
      • 12 Days On Market

      Last Sold Price $278,501

      Last Listing Agent Pamela Geib Long & Foster

  • /41

    $385,000

    • 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
  • /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
    • /20

      Est $207,424 Not Listed For Sale

      217 Greenridge Rd, Federalsburg, MD 21632

      • 2 Beds
      • 1.5 Baths
      • 1,276 Sq Ft
      • Built 1950
      217 Greenridge Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 7% Below List Price
      • $174/SF
      • 2 Days On Market

      Last Sold Price $222,000

      Last Listing Agent Shirley Coulbourne Coldwell Banker Realty

  • /33

    $365,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,503 Sq Ft

    22285 Tanyard Rd, Preston, MD 21655

    Tucked away just outside of town, this charming 3-bedroom, 2-bathroom home offers the perfect blend of privacy and space on a beautiful 4-acre property. The land features a mix of open, cleared yard and mature woods, providing both room to roam and a peaceful natural setting. Inside, the home offers a comfortable and functional layout, ideal for everyday living. One of the bedrooms includes a

    Wes Russum Coldwell Banker Chesapeake Real Estate Company

    22285 Tanyard Rd, 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
    • /25

      Est $267,686 Not Listed For Sale

      26280 Hobbs Rd, Denton, MD 21629

      • 2 Beds
      • 1.5 Baths
      • 960 Sq Ft
      • Built 1983
      26280 Hobbs Rd, Denton, MD 21629

      Last Sold Summary

      • 6% Above List Price
      • $263/SF
      • 6 Days On Market

      Last Sold Price $252,500

      Last Listing Agent Michelle Anderson Coldwell Banker Premier - Seaford

Showing Results 481 - 520, Page 13 of 18

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