15,709

Caroline County, MD Homes

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  • /22

    $189,900

    • 2 Beds
    • 1 Bath
    • 704 Sq Ft

    610 Lincoln St, Denton, MD 21629

    Easy living, charming bungalow tucked off the main drag yet close to everything. This Bungalow is the perfect spot to enjoy small town living. Remodeled with all the modern necessities, yet keeping the charm .Large deck off the back with a fenced in yard offers safe place for children and pets. A alley provides access tot he back for parking or a garage can be built. The current owners had

    Kat Thompson Benson & Mangold, LLC.

    610 Lincoln St, Denton, MD 21629
  • /34

    $280,000 Sold Mar 30, 2026

    2451 Guard Rd, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft
    • Built 2006

    Last Sold Summary

    • 12% Above List Price
    • $199/SF
    • 7 Days On Market

    Current Estimated Value $247,731

    Last Listing Agent Alicia Gannon Dulin Benson & Mangold, LLC

    2451 Guard Rd, Federalsburg, MD 21632
    • /22

      Est $420,223 Not Listed For Sale

      1702 Cattail Commons Way, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 3,096 Sq Ft
      • Built 2007
      1702 Cattail Commons Way, Denton, MD 21629

      Last Sold Summary

      • 6% Above List Price
      • $129/SF
      • 2 Days On Market
      • Last Sold Price $398,000
      • Dec 28, 2023

      Last Listing Agent Shirley Coulbourne Coldwell Banker Realty

  • /2

    $309,900 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 2,280 Sq Ft

    1624 Blue Heron Dr, Denton, MD 21629

    Move-in ready and thoughtfully updated—this is one you won’t want to miss. Step inside this newly renovated 2,200 sq. ft. townhome located in the heart of Denton, MD. Featuring four spacious bedrooms and 3.5 bathrooms, this home offers a perfect blend of comfort, functionality, and modern design. The entry level includes a versatile first-floor bedroom with a walk-in closet—ideal for guests, a

    Michelle DiDonato Island Realty, LLC

    1624 Blue Heron Dr, Denton, MD 21629
  • /33

    $320,000 Sold Jul 07, 2025

    3880 Laurel Grove Rd, Federalsburg, MD 21632

    • 3 Beds
    • 1 Bath
    • 1,092 Sq Ft
    • Built 1940

    Last Sold Summary

    • $293/SF
    • 4 Days On Market

    Current Estimated Value $325,384

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

    3880 Laurel Grove Rd, Federalsburg, MD 21632
    • /5

      Est $58,000 Not Listed For Sale

      120 Denton Rd, Federalsburg, MD 21632

      120 Denton Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 5,799,900% Above List Price
      • 205 Days On Market
      • Last Sold Price $1
      • Jan 10, 2024

      Last Listing Agent Myisha Walker Long & Foster

  • /127

    $2,999,000 Under Contract

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

    4218 Harmony Rd, Preston, MD 21655

    A truly rare offering for the discerning auto enthusiast, this exceptional 58.48-acre Eastern Shore estate is a masterfully designed luxury compound where architectural elegance meets world-class automotive accommodations. Introduced by a private gated entrance and tree-lined circular drive, the stately brick home immediately conveys the scale, privacy, and prestige of this one-of-a-kind

    Donna Harrington Coldwell Banker Realty

    4218 Harmony Rd, Preston, MD 21655
  • /33

    $191,000 Sold May 20, 2025

    22038 Church St, Hillsboro, MD 21641

    • Studio
    • 1,792 Sq Ft
    • Built 1950

    Last Sold Summary

    • $107/SF
    • 5 Days On Market

    Current Estimated Value $204,947

    Last Listing Agent Mary Mabry Keller Williams Select Realtors of Cambridge

    22038 Church St, Hillsboro, MD 21641
    • /18

      Est $507,456 Not Listed For Sale

      4191 Harmony Rd, Preston, MD 21655

      • 3 Beds
      • 2.5 Baths
      • 2,196 Sq Ft
      • Built 2007
      4191 Harmony Rd, Preston, MD 21655

      Last Sold Summary

      • 13% Above List Price
      • $205/SF
      • 10 Days On Market
      • Last Sold Price $450,000
      • Oct 27, 2023

      Last Listing Agent Chuck Mangold Benson & Mangold, LLC

  • /2

    $165,000

    • 3 Beds
    • 1 Bath
    • 1,015 Sq Ft

    208 W 2nd St, Ridgely, MD 21660

    Fixer up in town!!! New plumbing throughout, bathroom upgrade. New hot water 2025. More pictures coming.(Agent Owner)

    Dawn Williams Berkshire Hathaway Homeservice Homesale Realty

    208 W 2nd St, Ridgely, MD 21660
  • /48

    $460,000 Sold Jul 22, 2025

    14462 Poplar St, Goldsboro, MD 21636

    • 3 Beds
    • 2.5 Baths
    • 2,131 Sq Ft
    • Built 2003

    Last Sold Summary

    • $216/SF
    • 5 Days On Market

    Current Estimated Value $484,013

    Last Listing Agent Peter Mellor Wright Real Estate

    14462 Poplar St, Goldsboro, MD 21636
    • /13

      Est $333,227 Not Listed For Sale

      1306 Chesapeake Dr, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 1,654 Sq Ft
      • Built 2004
      1306 Chesapeake Dr, Denton, MD 21629

      Last Sold Summary

      • 11% Above List Price
      • $181/SF
      • 14 Days On Market
      • Last Sold Price $299,900
      • Jul 03, 2023

      Last Listing Agent Whitney Elliott Coldwell Banker Realty

  • /30

    $725,000

    • 4 Beds
    • 2.5 Baths
    • 1,880 Sq Ft

    1108 Camp Rd, Denton, MD 21629

    Welcome to 1108 Camp Street, sits on over 14 acres of land where modern comfort meets elegant design through an extensive list of upgrades that enhance both functionality and style. This home features stunning stone work on both the front and back, framing the house in natural beauty and providing a warm welcome. The meticulously crafted stone walls create an inviting outdoor ambiance. Venture

    Michelle Anderson Coldwell Banker Premier - Rehoboth

    1108 Camp Rd, Denton, MD 21629
  • /42

    $250,000 Sold Jun 06, 2025

    11204 Academy St, Hillsboro, MD 21641

    • 4 Beds
    • 1 Bath
    • 1,328 Sq Ft
    • Built 1800

    Last Sold Summary

    • $188/SF
    • 16 Days On Market

    Current Estimated Value $259,191

    Last Listing Agent Jennifer Chaney Chaney Homes, LLC

    11204 Academy St, Hillsboro, MD 21641
    • /30

      Est $405,597 Not Listed For Sale

      1106 Daylily Ln, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 3,096 Sq Ft
      • Built 2007
      1106 Daylily Ln, Denton, MD 21629

      Last Sold Summary

      • 2% Above List Price
      • $129/SF
      • 61 Days On Market
      • Last Sold Price $399,000
      • Feb 20, 2025

      Last Listing Agent Shirley Coulbourne Coldwell Banker Realty

  • /103

    $699,000

    • 3 Beds
    • 4 Baths
    • 2,756 Sq Ft

    4 S 1st St, Denton, MD 21629

    Outstanding Business Opportunity! Rare Find with-in Downtown Denton! Property would make an excellent Restaurant, Bar, great Venue , or a Large Victorian Home! Features include but not limited to Residential, Commerical or Mixed Use. Large Wrap around Porch for entertaining, Patio with plenty of room for seating with Firepit. Park like setting with Open Space and Large Pond! Town ERU's are

    Kathleen Brenton Brenton Realty Group

    4 S 1st St, Denton, MD 21629
  • /57

    $280,000 Sold Nov 26, 2025

    122 Mill St, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,104 Sq Ft
    • Built 2002

    Last Sold Summary

    • $254/SF
    • 48 Days On Market

    Current Estimated Value $281,365

    Last Listing Agent Carolyn Buchleitner Berkshire Hathaway HomeServices PenFed Realty

    122 Mill St, Greensboro, MD 21639
    • /27

      Est $392,261 Not Listed For Sale

      5576 Harmony Woods Dr, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,700 Sq Ft
      • Built 2020
      5576 Harmony Woods Dr, Preston, MD 21655

      Last Sold Summary

      • 2% Below List Price
      • $235/SF
      • 10 Days On Market
      • Last Sold Price $399,000
      • Jul 26, 2024

      Last Listing Agent Amy Betts Coldwell Banker Realty

  • /23

    $294,990 Pending

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

    119 Hobbs St, Greensboro, MD 21639

    Welcome to 119 Hobbs Street where a to-be-built new home can be yours in Kinnamon Meadows in Greensboro, MD. This home is not currently under construction but is one of the floorplans you can choose to build within this community. Prices vary based on selected upgrades, and prices shown generally refer to the base house without optional features. You’ll work with the builder to select from the

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

    119 Hobbs St, Greensboro, MD 21639
  • /24

    $212,000 Sold Jul 09, 2025

    524 Denton Rd, Federalsburg, MD 21632

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft
    • Built 1920

    Last Sold Summary

    • $245/SF
    • 9 Days On Market

    Current Estimated Value $206,407

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

    524 Denton Rd, Federalsburg, MD 21632
    • /6

      Est $116,472 Not Listed For Sale

      27105 River Bridge Rd, Henderson, MD 21640

      • Built 1955
      27105 River Bridge Rd, Henderson, MD 21640

      Last Sold Summary

      • 94% Above List Price
      • $56/SF
      • 4 Days On Market
      • Last Sold Price $60,000
      • Nov 27, 2024

      Last Listing Agent David Moore Real Broker, LLC

  • /5

    $130,000

    • Land
    • 8.85 Acres
    • $14,689 per Acre

    15589 Union Rd, Goldsboro, MD 21636

    25309 Golt farm Ln has an old vacant double-wide on it . PLEASE DO NOT GO INSIDE THE FLOORS ARE NOT SAFE TO GO IN.

    Diane Wenk Wright Real Estate

    15589 Union Rd, Goldsboro, MD 21636
  • /71

    $940,000 Sold Nov 17, 2025

    8816 Dorothy Ln, Denton, MD 21629

    • 4 Beds
    • 3.5 Baths
    • 4,092 Sq Ft
    • Built 1989

    Last Sold Summary

    • $230/SF
    • 166 Days On Market

    Current Estimated Value $966,700

    Last Listing Agent Dustin Parker The Parker Group

    8816 Dorothy Ln, Denton, MD 21629
    • /32

      Est $389,156 Not Listed For Sale

      26062 Holly Ln, Greensboro, MD 21639

      • 3 Beds
      • 2 Baths
      • 1,798 Sq Ft
      • Built 2007
      26062 Holly Ln, Greensboro, MD 21639

      Last Sold Summary

      • $217/SF
      • 89 Days On Market
      • Last Sold Price $390,000
      • Sep 30, 2024

      Last Listing Agent Norma Coursey Benson & Mangold, LLC

  • /45

    $469,900

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

    22408 Hog Creek Rd, Preston, MD 21655

    NEW PRICE! Enjoy peace and space on two tranquil country acres with no deed restrictions adjacent to open farmland. The deep backyard features a large vinyl-fenced area ideal for kids and pets, an above-ground pool with deck perfect for summer fun. This lovely home offers 2,667 Square feet (estimated) of living space, new LVP flooring on the main floor, and a versitile loft upstairs. The spacious

    James Bent Benson & Mangold, LLC

    22408 Hog Creek Rd, Preston, MD 21655
  • /25

    $235,000 Sold Oct 30, 2025

    113 Boyce Mill Rd, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 2007

    Last Sold Summary

    • $196/SF
    • 18 Days On Market

    Current Estimated Value $244,231

    Last Listing Agent Kat Thompson Benson & Mangold, LLC.

    113 Boyce Mill Rd, Greensboro, MD 21639
    • /23

      Est $168,079 Not Listed For Sale

      202B Maple Ave, Federalsburg, MD 21632

      • Studio
      • 1,640 Sq Ft
      • Built 1903
      202B Maple Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 68% Above List Price
      • $61/SF
      • 9 Days On Market
      • Last Sold Price $100,000
      • Jul 10, 2023

      Last Listing Agent Kathleen Brenton Brenton Realty Group

  • /2

    $210,000

    • 3 Beds
    • 2 Baths
    • 1,484 Sq Ft

    112 Noble Ave, Preston, MD 21655

    Investor Alert! 100% occupied duplex with a 2 bedroom, 1 bath downstairs and a 1 bedroom 1 bath upstairs. Situated in the heart of Preston and close proximity to the school.

    Chuck Mangold Benson & Mangold, LLC

    112 Noble Ave, Preston, MD 21655
  • /22

    $225,000 Sold Jun 18, 2025

    203 Bernard Ave, Federalsburg, MD 21632

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1972

    Last Sold Summary

    • $213/SF
    • 31 Days On Market

    Current Estimated Value $235,463

    Last Listing Agent Valerie Brown Charles C. Powell, Inc. Realtors

    203 Bernard Ave, Federalsburg, MD 21632
    • /52

      Est $353,512 Not Listed For Sale

      201 Church St, Greensboro, MD 21639

      • 4 Beds
      • 2 Baths
      • 2,559 Sq Ft
      • Built 1910
      201 Church St, Greensboro, MD 21639

      Last Sold Summary

      • 31% Above List Price
      • $106/SF
      • 59 Days On Market
      • Last Sold Price $270,000
      • Feb 01, 2024

      Last Listing Agent Julie Stevenson Shore Living Real Estate

  • /10

    $275,000

    • 3 Beds
    • 3 Baths
    • 2,128 Sq Ft

    21245 Tanyard Rd, Preston, MD 21655

    Charming Country Living with Room to Make It Your Own! Welcome to 21245 Tanyard Road, a spacious rancher with 3 bedrooms and 2 full baths nestled on a peaceful 0.62-acre lot in Preston. Built in 1987, this single-level home offers a solid foundation and a functional layout, ready for your personal touch and updates.Whether you're looking for a primary residence or an investment opportunity,

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    21245 Tanyard Rd, Preston, MD 21655
  • /44

    $220,000 Sold Oct 30, 2025

    148 Main St, Preston, MD 21655

    • 4 Beds
    • 2 Baths
    • 2,884 Sq Ft
    • Built 1880

    Last Sold Summary

    • $76/SF
    • 69 Days On Market

    Current Estimated Value $246,057

    Last Listing Agent Cheri Bruce-Phipps TTR Sotheby's International Realty

    148 Main St, Preston, MD 21655
    • /37

      Est $775,621 Not Listed For Sale

      10903 Collinswood Dr, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 4,404 Sq Ft
      • Built 2007
      10903 Collinswood Dr, Denton, MD 21629

      Last Sold Summary

      • 4% Below List Price
      • $183/SF
      • 4 Days On Market
      • Last Sold Price $805,000
      • Jul 18, 2024

      Last Listing Agent Bruce Hechmer Long & Foster

  • /25

    $85,000

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

    28035 Possum Hill Rd, Federalsburg, MD 21632

    Back on the market after demolition of the old house, full lot cleanup, and a garage facelift!This 0.48-acre property on Possum Hill Rd offers a strong opportunity in a desirable location less than one mile from the Maryland–Delaware state line. The lot is now cleared, providing open space and flexibility for a variety of potential uses.The property features an oversized pass-through

    Sam Benkirane Proplocate Realty, LLC

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

    $345,000 Sold Jul 30, 2025

    510 Pintail St, Greensboro, MD 21639

    • 5 Beds
    • 2.5 Baths
    • 1,984 Sq Ft
    • Built 2005

    Last Sold Summary

    • $174/SF
    • 91 Days On Market

    Current Estimated Value $358,513

    Last Listing Agent Jon Fleming Weichert Realtors - Blue Ribbon

    510 Pintail St, Greensboro, MD 21639
    • /39

      Est $391,732 Not Listed For Sale

      1140 Canvasback Ln, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,602 Sq Ft
      • Built 2007
      1140 Canvasback Ln, Denton, MD 21629

      Last Sold Summary

      • 5% Above List Price
      • $143/SF
      • 74 Days On Market
      • Last Sold Price $373,000
      • May 31, 2024

      Last Listing Agent Mark Milligan RE/MAX

  • /15

    $299,000

    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft

    506 Pintail St, Greensboro, MD 21639

    Nearly new ranch style home with large front porch. Three bedrooms and two full baths plus spacious laundry room enhance this home. Large kitchen with center island with stainless appliances and granite countertops are a focal point of this open floor plan. Move in ready and waiting for a new family!

    Bonnie Johnson Keller Williams Realty

    506 Pintail St, Greensboro, MD 21639
  • /16

    $230,000 Sold Apr 30, 2026

    115 Maple Ave, Goldsboro, MD 21636

    • 3 Beds
    • 2 Baths
    • 2,048 Sq Ft
    • Built 1900

    Last Sold Summary

    • 8% Below List Price
    • $112/SF
    • 65 Days On Market

    Current Estimated Value $221,403

    Last Listing Agent Sandra Bradley Keller Williams Select Realtors of Easton

    115 Maple Ave, Goldsboro, MD 21636
    • /45

      Est $233,113 Not Listed For Sale

      1306 Blue Heron Dr, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 1,620 Sq Ft
      • Built 2004
      1306 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 6% Below List Price
      • $152/SF
      • 3 Days On Market
      • Last Sold Price $247,000
      • Aug 13, 2024

      Last Listing Agent Lawrence Lessin Save 6, Incorporated

  • /30

    $289,000

    • 4 Beds
    • 1 Bath
    • 1,352 Sq Ft

    14185 Drapers Mill Rd, Greensboro, MD 21639

    Charming 2-Story Farmhouse set on 3 acres along a quiet country road, located directly next to a scenic bird sanctuary! This home offers 4 bedrooms and 1 full bath, including a convenient first-floor bedroom. The layout features a kitchen and dining combination, spacious family room, welcoming foyer, and a separate mudroom/laundry area. Enjoy the peaceful surroundings from the front and side

    John Lyons Crown Homes Real Estate

    14185 Drapers Mill Rd, Greensboro, MD 21639

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