15,709

Caroline County, MD Homes

Section Image Section Image
    • /32

      Est $260,281 Not Listed For Sale

      201 S 2nd St, Denton, MD 21629

      • 4 Beds
      • 2 Baths
      • 1,536 Sq Ft
      • Built 1885
      201 S 2nd St, Denton, MD 21629

      Last Sold Summary

      • 4% Above List Price
      • $163/SF
      • 135 Days On Market
      • Last Sold Price $250,000
      • Feb 26, 2025

      Last Listing Agent Darlene Winegardner RE/MAX

  • /20

    $325,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,092 Sq Ft

    15421 Oakland Rd, Goldsboro, MD 21636

    Opportunity is knocking and it’s sitting on 2 acres!This 3-bedroom, 2-bath home offers the perfect mix of space, functionality, and potential. Nestled on a generous lot, the property features a large pole building and an additional detached shed—ideal for storage, hobbies, equipment, or even your next big project.The home is equipped with solar panels that will be paid off at settlement,

    Heather Brummell Keller Williams Realty

    15421 Oakland Rd, Goldsboro, MD 21636
  • /56

    $125,000 Sold May 13, 2025

    101 Liberty Rd, Federalsburg, MD 21632

    • 4 Beds
    • 2 Baths
    • 3,386 Sq Ft
    • Built 1905

    Last Sold Summary

    • $37/SF
    • 43 Days On Market

    Current Estimated Value $206,486

    Last Listing Agent Ben Garner Cummings & Co. Realtors

    101 Liberty Rd, Federalsburg, MD 21632
    • /61

      Est $829,965 Not Listed For Sale

      24610 White Dogwood Dr, Denton, MD 21629

      • 6 Beds
      • 4 Baths
      • 4,950 Sq Ft
      • Built 1990
      24610 White Dogwood Dr, Denton, MD 21629

      Last Sold Summary

      • $167/SF
      • 107 Days On Market
      • Last Sold Price $826,900
      • Nov 15, 2024

      Last Listing Agent Kathleen Brenton Brenton Realty Group

  • /27

    $250,000

    • 3 Beds
    • 2 Baths
    • 1,311 Sq Ft

    25910 Fox Grape Rd, Greensboro, MD 21639

    Quiet living in Fox Grape Farms. Whether you are downsizing or just starting out, this home offers one-level living with 3 bedrooms, 2 full baths and an open living room that flows into the dining area. Situated on a 0.60 +/- parcel, the property also features two (2) storage sheds. Located approximately 7 miles from Denton, MD, 11 miles from Tuckahoe State Park and 16 miles from the Harrington

    John Fifer Brokers Realty Group, LLC

    25910 Fox Grape Rd, Greensboro, MD 21639
  • /60

    $400,000 Sold Jan 06, 2026

    106 Briarwood Cir, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 2,551 Sq Ft
    • Built 2021

    Last Sold Summary

    • $157/SF
    • 4 Days On Market

    Current Estimated Value $402,548

    Last Listing Agent Stephanie Smith Douglas Realty, LLC

    106 Briarwood Cir, Denton, MD 21629
    • /31

      Est $263,823 Not Listed For Sale

      3531 Linchester Rd, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,056 Sq Ft
      • Built 1972
      3531 Linchester Rd, Preston, MD 21655

      Last Sold Summary

      • 10% Above List Price
      • $227/SF
      • 37 Days On Market
      • Last Sold Price $240,000
      • Oct 02, 2023

      Last Listing Agent Linda Austin Long & Foster

  • /19

    $415,000 New Construction

    • 4 Beds
    • 2 Baths
    • 1,628 Sq Ft

    5 Sunrise Ave, Ridgely, MD 21660

    Pictured is Model- Colors, materials, and finishes are subject to change New Construction Home built by the reputable Lomaxx Custom Homes! The final home in Sunrise Village, this is your opportunity to get in early and make your personal selections. This one story home will offer 4 bedrooms, 2 full bathrooms and an open concept layout with stylish and on trend finishes throughout. Home to be

    Amy Betts Coldwell Banker Realty

    5 Sunrise Ave, Ridgely, MD 21660
  • /20

    $189,000 Sold Dec 02, 2025

    301 Central Ave, Ridgely, MD 21660

    • 4 Beds
    • 1 Bath
    • 1,706 Sq Ft
    • Built 1860

    Last Sold Summary

    • $111/SF
    • 7 Days On Market

    Current Estimated Value $197,939

    Last Listing Agent Jim Corson Benson & Mangold, LLC

    301 Central Ave, Ridgely, MD 21660
    • /34

      Est $326,503 Not Listed For Sale

      305 S 2nd St, Denton, MD 21629

      • 4 Beds
      • 2 Baths
      • 2,024 Sq Ft
      • Built 1890
      305 S 2nd St, Denton, MD 21629

      Last Sold Summary

      • 9% Above List Price
      • $148/SF
      • 225 Days On Market
      • Last Sold Price $299,000
      • May 15, 2024

      Last Listing Agent Kat Thompson Benson & Mangold, LLC.

  • /52

    $475,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,858 Sq Ft

    12484 Greensboro Rd, Greensboro, MD 21639

    Experience the best of Eastern Shore living on just over 2 acres of private land. This home features a spacious family room complete with a pellet stove and a kitchen that boasts custom-built Amish oak cabinets, granite countertops, and a tile backsplash. The entire home is equipped with LVP flooring for a modern touch. A large primary addition has been added, while the other bedrooms are

    Roger Boyce Chesapeake Real Estate Associates, LLC

    12484 Greensboro Rd, Greensboro, MD 21639
  • /21

    $249,500 Sold Nov 10, 2025

    529 N 6th St, Denton, MD 21629

    • 3 Beds
    • 1 Bath
    • 1,019 Sq Ft
    • Built 1930

    Last Sold Summary

    • $245/SF
    • 62 Days On Market

    Current Estimated Value $243,052

    Last Listing Agent Cody Weese Weese Properties, LLC

    529 N 6th St, Denton, MD 21629
    • /36

      Est $317,726 Not Listed For Sale

      303 Central Ave, Ridgely, MD 21660

      • 4 Beds
      • 2 Baths
      • 1,440 Sq Ft
      • Built 1850
      303 Central Ave, Ridgely, MD 21660

      Last Sold Summary

      • 6% Above List Price
      • $208/SF
      • 53 Days On Market
      • Last Sold Price $300,000
      • Jul 07, 2023

      Last Listing Agent Michele Hamilton Taylor Properties

  • /28

    $239,900

    • 3 Beds
    • 1 Bath
    • 1,080 Sq Ft

    6413 Reliance Rd, Federalsburg, MD 21632

    Nice 3 bedroom 1 bath Rancher with garage in quiet country setting. This one will not last long!!

    Blaine Williamson McClain-Williamson Realty, LLC

    6413 Reliance Rd, Federalsburg, MD 21632
  • /70

    $325,000 Sold Mar 12, 2026

    25361 Calvert Dr, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,450 Sq Ft
    • Built 1989

    Last Sold Summary

    • $224/SF
    • 50 Days On Market

    Current Estimated Value $328,273

    Last Listing Agent Chris Rosendale CR Realty

    25361 Calvert Dr, Greensboro, MD 21639
    • /31

      Est $286,363 Not Listed For Sale

      108 Park Ave, Ridgely, MD 21660

      • 3 Beds
      • 2 Baths
      • 1,392 Sq Ft
      • Built 1890
      108 Park Ave, Ridgely, MD 21660

      Last Sold Summary

      • 6% Above List Price
      • $193/SF
      • 20 Days On Market
      • Last Sold Price $269,000
      • Jul 14, 2023

      Last Listing Agent Jimmy Rupert Douglas Realty, LLC

  • /35

    $249,900 Pending

    • 2 Beds
    • 1 Bath
    • 1,140 Sq Ft

    3540 Houston Branch Rd, Federalsburg, MD 21632

    Welcome to 3540 Houston Branch Rd. It was purchased in 2021 and has undergone extensive renovations. The interior was taken down to the studs. There is new drywall, flooring and sub flooring, a complete bath room, windows, kitchen cabinets, appliances and quartz counter tops. Even the electric was updated along with plumbing. Did I mention a new roof, well and septic system!! This is a perfect

    Eddie Matthews Benson & Mangold, LLC

    3540 Houston Branch Rd, Federalsburg, MD 21632
  • /71

    $450,000 Sold Sep 19, 2025

    122 Lister Ln, Ridgely, MD 21660

    • 4 Beds
    • 3 Baths
    • 4,304 Sq Ft
    • Built 2006

    Last Sold Summary

    • $105/SF
    • 30 Days On Market

    Current Estimated Value $452,800

    Last Listing Agent Chris Rosendale CR Realty

    122 Lister Ln, Ridgely, MD 21660
    • /80

      Est $464,719 Not Listed For Sale

      14645 Fox Chase Cir, Ridgely, MD 21660

      • 3 Beds
      • 2 Baths
      • 2,624 Sq Ft
      • Built 1994
      14645 Fox Chase Cir, Ridgely, MD 21660

      Last Sold Summary

      • 1% Above List Price
      • $175/SF
      • 66 Days On Market
      • Last Sold Price $460,000
      • Dec 20, 2024

      Last Listing Agent Barbara McCaffrey Redfin Corp

  • /38

    $280,000 Under Contract

    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft

    618 Academy Ave, Federalsburg, MD 21632

    One or more photo(s) has been virtually staged. Welcome home! This beautifully cared-for property offers small-town charm with big advantages — no town taxes and only a five-minute walk to the local elementary school. Sitting on a spacious 0.78-acre lot, you'll love the huge backyard, perfect for kids, pets, or backyard cookouts. The large circular driveway provides plenty of parking, and there’s

    Kaitlyn Collins Benson & Mangold, LLC

    618 Academy Ave, Federalsburg, MD 21632
  • /23

    $365,000 Sold Dec 22, 2025

    8 Sunrise Ave, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,292 Sq Ft
    • Built 2025

    Last Sold Summary

    • $283/SF
    • 6 Days On Market

    Last Listing Agent Amy Betts Coldwell Banker Realty

    8 Sunrise Ave, Ridgely, MD 21660
    • /30

      Est $389,408 Not Listed For Sale

      7675 Tall Tree Ln, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 1998
      7675 Tall Tree Ln, Preston, MD 21655

      Last Sold Summary

      • 2% Above List Price
      • $284/SF
      • 4 Days On Market
      • Last Sold Price $381,900
      • Mar 27, 2024

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

  • /48

    $330,000

    • 2 Beds
    • 1.5 Baths
    • 708 Sq Ft

    13306 Greensboro Rd, Greensboro, MD 21639

    Stunning waterfront renovation on the Choptank River—completely redone inside and out in 2025! This beautifully updated 2-bedroom, 1.5-bath home offers approximately 800± square feet of thoughtfully designed living space. Completely remodeled from top to bottom, the residence showcases modern design and high-end finishes throughout. Updates include all-new walls, bathrooms, appliances, kitchen

    Lisa Magnus Clark & Co Realty, LLC

    13306 Greensboro Rd, Greensboro, MD 21639
  • /15

    $200,000 Sold Sep 15, 2025

    307 W Central Ave, Federalsburg, MD 21632

    • 3 Beds
    • 1 Bath
    • 1,340 Sq Ft
    • Built 1935

    Last Sold Summary

    • $149/SF
    • 105 Days On Market

    Current Estimated Value $203,110

    Last Listing Agent Mary Mabry Keller Williams Select Realtors of Cambridge

    307 W Central Ave, Federalsburg, MD 21632
    • /43

      Est $256,031 Not Listed For Sale

      9165 Andersontown Rd, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,680 Sq Ft
      • Built 1900
      9165 Andersontown Rd, Denton, MD 21629

      Last Sold Summary

      • 11% Above List Price
      • $137/SF
      • 141 Days On Market
      • Last Sold Price $230,000
      • Sep 29, 2023

      Last Listing Agent Kathleen Brenton Brenton Realty Group

  • /2

    $55,000

    • Land
    • 4.17 Acres
    • $13,189 per Acre

    E/S MD RT480 Unknown, Hillsboro, MD 21641

    Seller is waiting for perk results from Caroline county health department

    Diane Wenk Wright Real Estate

    E/S MD RT480 Unknown, Hillsboro, MD 21641
  • /6

    $309,900 Sold Jun 05, 2025

    3449 Jefferson Pond Rd, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2025

    Last Sold Summary

    • $231/SF
    • 39 Days On Market

    Last Listing Agent Amy Herr Keller Williams Realty

    3449 Jefferson Pond Rd, Federalsburg, MD 21632
    • /24

      Est $255,982 Not Listed For Sale

      211 W Central Ave, Federalsburg, MD 21632

      • 3 Beds
      • 2 Baths
      • 2,416 Sq Ft
      • Built 1934
      211 W Central Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 60% Above List Price
      • $66/SF
      • 43 Days On Market
      • Last Sold Price $160,000
      • Dec 08, 2023

      Last Listing Agent Mike McCarthy Metro DMV Realty

  • /25

    $240,000 Sold Nov 12, 2025

    317 W Central Ave, Federalsburg, MD 21632

    • 4 Beds
    • 1.5 Baths
    • 1,670 Sq Ft
    • Built 1931

    Last Sold Summary

    • $144/SF
    • 56 Days On Market

    Current Estimated Value $236,295

    Last Listing Agent Kelly Sharpless Kelstar Properties

    317 W Central Ave, Federalsburg, MD 21632
    • /32

      Est $289,662 Not Listed For Sale

      318 S 4th St, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,176 Sq Ft
      • Built 2001
      318 S 4th St, Denton, MD 21629

      Last Sold Summary

      • 2% Below List Price
      • $251/SF
      • 66 Days On Market
      • Last Sold Price $295,000
      • Jan 09, 2024

      Last Listing Agent Darrel Reel Corner House Realty

  • /2

    $399,000 Sold Jul 03, 2025

    5549 Harmony Woods Dr, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft
    • Built 2025

    Last Sold Summary

    • $228/SF
    • 42 Days On Market

    Last Listing Agent Shirley Coulbourne Coldwell Banker Realty

    5549 Harmony Woods Dr, Preston, MD 21655
    • /25

      Est $243,989 Not Listed For Sale

      715 Market St, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 2,436 Sq Ft
      • Built 1900
      715 Market St, Denton, MD 21629

      Last Sold Summary

      • 103% Above List Price
      • $49/SF
      • 166 Days On Market
      • Last Sold Price $120,000
      • Aug 25, 2023

      Last Listing Agent Sherry Price RealHome Services and Solutions, Inc.

  • 131 Hobbs St, Greensboro, MD 21639

    $292,990 Sold Jan 15, 2026

    131 Hobbs St, Greensboro, MD 21639

    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $201/SF
    • 76 Days On Market

    D.R. Horton Kinnamon Meadows

    131 Hobbs St, Greensboro, MD 21639
    • /17

      Est $155,607 Not Listed For Sale

      207 Caroline Ave, Ridgely, MD 21660

      • 3 Beds
      • 1.5 Baths
      • 1,008 Sq Ft
      • Built 1890
      207 Caroline Ave, Ridgely, MD 21660

      Last Sold Summary

      • 4% Above List Price
      • $149/SF
      • 6 Days On Market
      • Last Sold Price $150,000
      • Apr 30, 2025

      Last Listing Agent Timothy Caropreso Keller Williams Flagship

  • /20

    $350,000 Sold Jun 13, 2025

    23807 Westbridge Dr, Henderson, MD 21640

    • 3 Beds
    • 2 Baths
    • 1,736 Sq Ft
    • Built 1996

    Last Sold Summary

    • $202/SF
    • 2 Days On Market

    Current Estimated Value $391,506

    Last Listing Agent Amanda Morgan Brenton Realty Group

    23807 Westbridge Dr, Henderson, MD 21640
    • /14

      Est $284,290 Not Listed For Sale

      560 Vaughn Ave, Greensboro, MD 21639

      • 4 Beds
      • 2.5 Baths
      • 1,828 Sq Ft
      • Built 2004
      560 Vaughn Ave, Greensboro, MD 21639

      Last Sold Summary

      • 11% Above List Price
      • $139/SF
      • 4 Days On Market
      • Last Sold Price $255,000
      • Aug 08, 2023

      Last Listing Agent Linda Moore Long & Foster

  • /44

    $438,500 Sold Sep 05, 2025

    14267 Cherry Ln, Queen Anne, MD 21657

    • 3 Beds
    • 3 Baths
    • 1,884 Sq Ft
    • Built 1994

    Last Sold Summary

    • $233/SF
    • 18 Days On Market

    Current Estimated Value $443,612

    Last Listing Agent Rick Parreco RE/MAX Executive

    14267 Cherry Ln, Queen Anne, MD 21657
    • /30

      Est $281,801 Not Listed For Sale

      104 S Academy St, Greensboro, MD 21639

      • 3 Beds
      • 2 Baths
      • 1,326 Sq Ft
      • Built 2012
      104 S Academy St, Greensboro, MD 21639

      Last Sold Summary

      • 4% Above List Price
      • $204/SF
      • 27 Days On Market
      • Last Sold Price $270,000
      • Dec 08, 2023

      Last Listing Agent Kelly McDevitt Cummings & Co Realtors

  • /63

    $529,900 Sold May 28, 2025

    20735 Tammuxzena Dr, Preston, MD 21655

    • 3 Beds
    • 2.5 Baths
    • 2,250 Sq Ft
    • Built 2025

    Last Sold Summary

    • $236/SF
    • 6 Days On Market

    Current Estimated Value $558,564

    Last Listing Agent Leo Kuneman Meredith Fine Properties

    20735 Tammuxzena Dr, Preston, MD 21655
    • /41

      Est $304,467 Not Listed For Sale

      21965 Marsh Creek Rd, Preston, MD 21655

      • 3 Beds
      • 1.5 Baths
      • 1,008 Sq Ft
      • Built 1943
      21965 Marsh Creek Rd, Preston, MD 21655

      Last Sold Summary

      • 9% Above List Price
      • $277/SF
      • 4 Days On Market
      • Last Sold Price $279,500
      • Jul 14, 2023

      Last Listing Agent Chris Rosendale CR Realty

Showing Results 641 - 680, Page 17 of 18

How to Buy a Home How to Finance a Home How to Sell a Home