15,675

Caroline County, MD Homes

Section Image
  • 27329 Iron Gate Rd, Federalsburg, MD 21632
    27329 Iron Gate Rd, Federalsburg, MD 21632
    27329 Iron Gate Rd, Federalsburg, MD 21632
    /57

    $475,000

    • 3 Beds
    • 2 Baths
    • 2,038 Sq Ft

    27329 Iron Gate Rd, Federalsburg, MD 21632

    Charming Colonial-style farmhouse set on 9 scenic acres, offering a rare blend of historic character, pastoral beauty, and endless potential. Ideal for animal lovers or those seeking a peaceful weekend retreat, the home features hardwood floors, exposed ceiling beams, and three wood-burning stoves that add warmth and timeless appeal. Large Spacious bedrooms, a screened porch and rear patio

    Shannon Parker Keller Williams Select Realtors of Cambridge

    27329 Iron Gate Rd, Federalsburg, MD 21632
  • 143 Riverwalk Terrace, Federalsburg, MD 21632
    143 Riverwalk Terrace, Federalsburg, MD 21632
    143 Riverwalk Terrace, Federalsburg, MD 21632
    /27

    $219,990 Sold Aug 29, 2025

    143 Riverwalk Terrace, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 1,365 Sq Ft
    • Built 2025

    Last Sold Summary

    • $161/SF
    • 6 Days On Market

    Current Estimated Value $231,106

    Last Listing Agent Kathleen Cassidy D R Horton Realty of Virginia LLC

    143 Riverwalk Terrace, Federalsburg, MD 21632
    • 22354 Hillsboro Rd, Denton, MD 21629
      22354 Hillsboro Rd, Denton, MD 21629
      22354 Hillsboro Rd, Denton, MD 21629
      /21

      Est $350,508 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,536 Sq Ft

      22354 Hillsboro Rd, Denton, MD 21629

      22354 Hillsboro Rd, Denton, MD 21629
  • 12658 Oakland Rd, Ridgely, MD 21660
    12658 Oakland Rd, Ridgely, MD 21660
    12658 Oakland Rd, Ridgely, MD 21660
    /54

    $425,000

    • 4 Beds
    • 2 Baths
    • 1,692 Sq Ft

    12658 Oakland Rd, Ridgely, MD 21660

    Right on the outskirts of the Historic Town of Ridgely Maryland you will find this fully remodeled 4 bedroom rancher on a beautiful acre of land. A fenced backyard perfect for your pets and or your small farm animal dreams! Plenty of room for a kitchen garden too! Inside you will find a recently remodeled open concept kitchen with large island that makes for a great workspace & great gatherings!

    John Cary Rosendale Realty

    12658 Oakland Rd, Ridgely, MD 21660
  • 517 Gay St, Denton, MD 21629
    517 Gay St, Denton, MD 21629
    517 Gay St, Denton, MD 21629
    /46

    $330,000 Sold Apr 15, 2025

    517 Gay St, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 3,734 Sq Ft
    • Built 1957

    Last Sold Summary

    • $88/SF
    • 213 Days On Market

    Current Estimated Value $370,314

    Last Listing Agent Barbara Beaudet Brenton Realty Group

    517 Gay St, Denton, MD 21629
    • 24565 Holsinger Ln, Ridgely, MD 21660
      24565 Holsinger Ln, Ridgely, MD 21660
      24565 Holsinger Ln, Ridgely, MD 21660
      /33

      Est $422,266 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,500 Sq Ft

      24565 Holsinger Ln, Ridgely, MD 21660

      24565 Holsinger Ln, Ridgely, MD 21660
  • 305 Central Ave, Ridgely, MD 21660
    305 Central Ave, Ridgely, MD 21660
    305 Central Ave, Ridgely, MD 21660
    /19

    $299,000

    • 5 Beds
    • 2 Baths
    • 2,574 Sq Ft

    305 Central Ave, Ridgely, MD 21660

    Welcome home to this spacious 5-bedroom, 2-bath Colonial located in the heart of Ridgely. This in-town property offers a large kitchen with plenty of space for cooking and entertaining, a comfortable living room, and generously sized bedrooms throughout. The traditional floor plan provides a warm and inviting flow, perfect for both daily living and hosting guests. Enjoy the convenience of being

    Katie Moore Coldwell Banker Chesapeake Real Estate Company

    305 Central Ave, Ridgely, MD 21660
  • 11145 Branch Ct, Denton, MD 21629
    11145 Branch Ct, Denton, MD 21629
    11145 Branch Ct, Denton, MD 21629
    /36

    $375,000 Sold Jun 30, 2025

    11145 Branch Ct, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1999

    Last Sold Summary

    • $279/SF
    • 82 Days On Market

    Current Estimated Value $408,236

    Last Listing Agent Sean O'Connor Coldwell Banker Realty

    11145 Branch Ct, Denton, MD 21629
    • 22700 Thawley Rd, Denton, MD 21629
      22700 Thawley Rd, Denton, MD 21629
      22700 Thawley Rd, Denton, MD 21629
      /24

      Est $485,091 Not Listed For Sale

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

      22700 Thawley Rd, Denton, MD 21629

      22700 Thawley Rd, Denton, MD 21629
  • 115 Maple Ave, Goldsboro, MD 21636
    115 Maple Ave, Goldsboro, MD 21636
    115 Maple Ave, Goldsboro, MD 21636
    /16

    $250,000

    • 4 Beds
    • 2 Baths
    • 2,048 Sq Ft

    115 Maple Ave, Goldsboro, MD 21636

    Step into a rare opportunity to own a beautifully updated Victorian-style home located on a quiet, established street in the heart of Goldsboro. Perfectly situated on a generous 0.55-acre lot, this home offers over 2,000 square feet of flexible living space while preserving the character buyers love. Inside, the freshly painted interior and brand new laminate flooring create a bright and

    Sandra Bradley Keller Williams Select Realtors of Easton

    115 Maple Ave, Goldsboro, MD 21636
  • 505 Market St, Denton, MD 21629
    505 Market St, Denton, MD 21629
    505 Market St, Denton, MD 21629
    /13

    $225,000 Sold Aug 15, 2025

    505 Market St, Denton, MD 21629

    • 4 Beds
    • 2 Baths
    • 3,731 Sq Ft
    • Built 1890

    Last Sold Summary

    • $60/SF
    • 148 Days On Market

    Current Estimated Value $252,363

    Last Listing Agent Barbara Beaudet Brenton Realty Group

    505 Market St, Denton, MD 21629
    • 24911 Woods Dr, Denton, MD 21629
      24911 Woods Dr, Denton, MD 21629
      24911 Woods Dr, Denton, MD 21629
      /36

      Est $559,250 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 3,222 Sq Ft

      24911 Woods Dr, Denton, MD 21629

      24911 Woods Dr, Denton, MD 21629
  • 0 Nelpine Rd, Preston, MD 21655
    0 Nelpine Rd, Preston, MD 21655
    0 Nelpine Rd, Preston, MD 21655
    /4

    $20,000

    • Land
    • 0.5 Acre
    • $40,000 per Acre

    0 Nelpine Rd, Preston, MD 21655

    Discover a hidden gem on Nelpine Rd, a 0.50-acre property located in a small community just north of Preston off Harmony Road. This half-acre of vacant land is a blank canvas awaiting your vision. Whether you're a developer, an investor, or someone looking to build a personal sanctuary, this property offers limitless potential. Only 15 minutes to Choptank River, 20 minutes to Easton, under an

    ryan byrd Coldwell Banker Realty

    0 Nelpine Rd, Preston, MD 21655
  • 106 Morning Glory Dr, Denton, MD 21629
    106 Morning Glory Dr, Denton, MD 21629
    106 Morning Glory Dr, Denton, MD 21629
    /41

    $382,000 Sold Jun 06, 2025

    106 Morning Glory Dr, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,664 Sq Ft
    • Built 2022

    Last Sold Summary

    • $230/SF
    • 254 Days On Market

    Current Estimated Value $404,712

    Last Listing Agent Dan Foster Long & Foster Real Estate, Inc.

    106 Morning Glory Dr, Denton, MD 21629
    • 25400 Calvert Dr, Greensboro, MD 21639
      25400 Calvert Dr, Greensboro, MD 21639
      25400 Calvert Dr, Greensboro, MD 21639
      /31

      Est $396,894 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,742 Sq Ft

      25400 Calvert Dr, Greensboro, MD 21639

      25400 Calvert Dr, Greensboro, MD 21639
  • 306 S Main St, Federalsburg, MD 21632
    306 S Main St, Federalsburg, MD 21632
    306 S Main St, Federalsburg, MD 21632
    /41

    $269,900

    • 4 Beds
    • 1.5 Baths
    • 2,820 Sq Ft

    306 S Main St, Federalsburg, MD 21632

    Bring Your Fishing Pole! Nestled along the tranquil waters of Marshyhope Creek, this waterfront retreat offers peaceful views and the rare opportunity to fish or kayak directly from your own private shoreline. This charming 2,820 sq. ft. Victorian home features 4 spacious, freshly painted bedrooms and 1.5 baths and is ready for you to add your special touches. Begin your mornings with coffee on

    Mary Mabry Keller Williams Select Realtors of Cambridge

    306 S Main St, Federalsburg, MD 21632
  • 22879 Stevenson Rd, Ridgely, MD 21660
    22879 Stevenson Rd, Ridgely, MD 21660
    22879 Stevenson Rd, Ridgely, MD 21660
    /121

    $835,000 Sold Jun 06, 2025

    22879 Stevenson Rd, Ridgely, MD 21660

    • 5 Beds
    • 5 Baths
    • 5,328 Sq Ft
    • Built 2012

    Last Sold Summary

    • $157/SF
    • 47 Days On Market

    Current Estimated Value $880,324

    Last Listing Agent Chris Rosendale CR Realty

    22879 Stevenson Rd, Ridgely, MD 21660
    • 9605 Quail Run Rd, Denton, MD 21629
      9605 Quail Run Rd, Denton, MD 21629
      9605 Quail Run Rd, Denton, MD 21629
      /21

      Est $510,795 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,646 Sq Ft

      9605 Quail Run Rd, Denton, MD 21629

      9605 Quail Run Rd, Denton, MD 21629
  • 409 Main St, Goldsboro, MD 21636
    409 Main St, Goldsboro, MD 21636
    409 Main St, Goldsboro, MD 21636
    /19

    $200,000 Pending

    • 2 Beds
    • 1.5 Baths
    • 1,252 Sq Ft

    409 Main St, Goldsboro, MD 21636

    After no fault of the Sellers this property is back to Active and ready for its new Owners. Welcome to 409 Main Street, a delightful 2 bedroom, 1.5 bath home nestled in the heart of Goldsboro. This property features a cozy living room with pellet stove, dining room, a functional kitchen, bonus room (use as an office or 3rd bedroom), comfortable bedrooms and a basement offering endless potential

    Amy Betts Coldwell Banker Realty

    409 Main St, Goldsboro, MD 21636
  • Lot 3 Clark Canning House Rd, Federalsburg, MD 21632
    Lot 3 Clark Canning House Rd, Federalsburg, MD 21632
    Lot 3 Clark Canning House Rd, Federalsburg, MD 21632
    /3

    $85,000 Sold Sep 16, 2025

    Lot 3 Clark Canning House Rd, Federalsburg, MD 21632

    • Land
    • 2 Acres
    • $42,500 per Acre

    Last Sold Summary

    • 160 Days On Market

    Last Listing Agent Mickey Hayward Sunset Properties

    Lot 3 Clark Canning House Rd, Federalsburg, MD 21632
    • 8614 Andersontown Rd, Denton, MD 21629
      8614 Andersontown Rd, Denton, MD 21629
      8614 Andersontown Rd, Denton, MD 21629
      /37

      Est $435,217 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,300 Sq Ft

      8614 Andersontown Rd, Denton, MD 21629

      8614 Andersontown Rd, Denton, MD 21629
  • 511 Bernard Ave, Greensboro, MD 21639
    511 Bernard Ave, Greensboro, MD 21639
    511 Bernard Ave, Greensboro, MD 21639
    /43

    $245,000

    • 3 Beds
    • 1 Bath
    • 1,385 Sq Ft

    511 Bernard Ave, Greensboro, MD 21639

    Spacious rancher located on a double lot, over one-third of an acre, plenty of room for outdoor activities or potential future expansion. This home features solid construction and has had significant updates in the past 3-4 years, including a new roof, new windows, and a new HVAC system, adding considerable value and reduces the worry about major repairs in the near future. Inside the residence

    Karen Clark Clark & Co Realty, LLC

    511 Bernard Ave, Greensboro, MD 21639
  • 5059 Gina Ln, Federalsburg, MD 21632
    5059 Gina Ln, Federalsburg, MD 21632
    5059 Gina Ln, Federalsburg, MD 21632
    /31

    $280,000 Sold Jul 24, 2025

    5059 Gina Ln, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft
    • Built 1981

    Last Sold Summary

    • $192/SF
    • 120 Days On Market

    Current Estimated Value $291,530

    Last Listing Agent Andrew Beaven Wright Real Estate

    5059 Gina Ln, Federalsburg, MD 21632
    • 309 S University Ave, Federalsburg, MD 21632
      309 S University Ave, Federalsburg, MD 21632
      309 S University Ave, Federalsburg, MD 21632
      /9

      Est $165,500 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,296 Sq Ft

      309 S University Ave, Federalsburg, MD 21632

      309 S University Ave, Federalsburg, MD 21632
  • 300 S 1st St, Denton, MD 21629
    300 S 1st St, Denton, MD 21629
    300 S 1st St, Denton, MD 21629
    /47

    $625,000

    • 3 Beds
    • 2 Baths
    • 1,616 Sq Ft

    300 S 1st St, Denton, MD 21629

    Peaceful Living on the Choptank River!!! One level Living! Offering 3 Bed and 1.5 Bath. Home features an open Floor Plan with Large Living Room w/ Gas Burning Stove., Spacious Kitchen with Tons of Storage, Breakfast Bar, and plenty of space for your Table and Chairs! Primary Bedroom facing the Water with Great Waterfront Views. Home also features a paved driveway with 2 door garage and a full

    Kathleen Brenton Brenton Realty Group

    300 S 1st St, Denton, MD 21629
  • 3297 Gallagher Rd, Preston, MD 21655
    3297 Gallagher Rd, Preston, MD 21655
    3297 Gallagher Rd, Preston, MD 21655
    /72

    $320,000 Sold May 02, 2025

    3297 Gallagher Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,544 Sq Ft
    • Built 1994

    Last Sold Summary

    • $207/SF
    • 84 Days On Market

    Last Listing Agent Barbara Dayton Long & Foster Real Estate, Inc.

    3297 Gallagher Rd, Preston, MD 21655
    • 4925 Edmondson Creek Rd, Preston, MD 21655
      4925 Edmondson Creek Rd, Preston, MD 21655
      4925 Edmondson Creek Rd, Preston, MD 21655
      /58

      Est $507,891 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 1,988 Sq Ft

      4925 Edmondson Creek Rd, Preston, MD 21655

      4925 Edmondson Creek Rd, Preston, MD 21655
  • lot 6 Harmony Woods Dr, Preston, MD 21655
    lot 6 Harmony Woods Dr, Preston, MD 21655
    /2

    $79,000

    • Land
    • 2.11 Acres
    • $37,441 per Acre

    lot 6 Harmony Woods Dr, Preston, MD 21655

    Barbara Nichols Results Realty Inc.

    lot 6 Harmony Woods Dr, Preston, MD 21655
  • 0 Cool Spring Rd Unit MDCM2005520, Marydel, MD 21649
    0 Cool Spring Rd Unit MDCM2005520, Marydel, MD 21649
    0 Cool Spring Rd Unit MDCM2005520, Marydel, MD 21649
    /49

    $750,000 Sold Nov 12, 2025

    0 Cool Spring Rd Unit MDCM2005520, Marydel, MD 21649

    • Land
    • 187 Acres
    • $4,011 per Acre

    Last Sold Summary

    • 139 Days On Market

    Last Listing Agent Benjamin Alder The Land Group

    0 Cool Spring Rd Unit MDCM2005520, Marydel, MD 21649
    • 24754 Pealiquor Rd, Denton, MD 21629
      24754 Pealiquor Rd, Denton, MD 21629
      24754 Pealiquor Rd, Denton, MD 21629
      /124

      Est $755,927 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,921 Sq Ft

      24754 Pealiquor Rd, Denton, MD 21629

      24754 Pealiquor Rd, Denton, MD 21629
  • 162 Main St, Preston, MD 21655
    162 Main St, Preston, MD 21655
    162 Main St, Preston, MD 21655
    /4

    $92,000

    • Land
    • 0.33 Acre
    • $278,788 per Acre

    162 Main St, Preston, MD 21655

    Anne Schmidt Long & Foster Real Estate, Inc.

    162 Main St, Preston, MD 21655
  • 130 Walnut St, Ridgely, MD 21660
    130 Walnut St, Ridgely, MD 21660
    130 Walnut St, Ridgely, MD 21660
    /27

    $369,000 Sold Nov 17, 2025

    130 Walnut St, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,548 Sq Ft
    • Built 2011

    Last Sold Summary

    • $238/SF
    • 5 Days On Market

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

    130 Walnut St, Ridgely, MD 21660
    • 25698 Caroline St, Greensboro, MD 21639
      25698 Caroline St, Greensboro, MD 21639
      25698 Caroline St, Greensboro, MD 21639
      /26

      Est $401,409 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,512 Sq Ft

      25698 Caroline St, Greensboro, MD 21639

      25698 Caroline St, Greensboro, MD 21639
  • 1303 Fairfield Ct, Denton, MD 21629
    1303 Fairfield Ct, Denton, MD 21629
    1303 Fairfield Ct, Denton, MD 21629
    /20

    $290,000

    • 2 Beds
    • 1 Bath
    • 1,426 Sq Ft

    1303 Fairfield Ct, Denton, MD 21629

    This charming ranch-style home in the Fairfield subdivision offers a blend of comfort and convenience. Built in 2003, the property features durable vinyl siding and a well-maintained exterior with a gutter system, sidewalks, and street lights enhancing the neighborhood's appeal. The 0.14-acre lot includes a private rear yard, perfect for outdoor activities. Inside, the home boasts 1,426 sq. ft.

    Tricia Wilson Wilson Realty & Staging LLC

    1303 Fairfield Ct, Denton, MD 21629
  • 4516 Frazier Neck Rd, Preston, MD 21655
    4516 Frazier Neck Rd, Preston, MD 21655
    4516 Frazier Neck Rd, Preston, MD 21655
    /13

    $350,000 Sold Sep 05, 2025

    4516 Frazier Neck Rd, Preston, MD 21655

    • 2 Beds
    • 1 Bath
    • 1,050 Sq Ft
    • Built 1969

    Last Sold Summary

    • $333/SF
    • 5 Days On Market

    Current Estimated Value $370,581

    Last Listing Agent Benjamin Alder The Land Group

    4516 Frazier Neck Rd, Preston, MD 21655
    • 8157 Arch Dr, Denton, MD 21629
      8157 Arch Dr, Denton, MD 21629
      8157 Arch Dr, Denton, MD 21629
      /34

      Est $364,526 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,232 Sq Ft

      8157 Arch Dr, Denton, MD 21629

      8157 Arch Dr, Denton, MD 21629
  • 8578 Tuckahoe Rd, Denton, MD 21629
    8578 Tuckahoe Rd, Denton, MD 21629
    8578 Tuckahoe Rd, Denton, MD 21629
    /64

    $425,000

    • 4 Beds
    • 3 Baths
    • 1,680 Sq Ft

    8578 Tuckahoe Rd, Denton, MD 21629

    This property boasts with a 4 bedroom 3 full bathroom cape cod on a 1 acre lot in a beautiful wide open country setting! Fresh paint throughout the entire house, new refrigerator, new oven, new dryer AND new HVAC! All of the hard work has been done! Minutes to Denton or Easton. Move in ready! There is still plenty of time to be in a new home for the holidays!

    Megan Rosendale Rosendale Realty

    8578 Tuckahoe Rd, Denton, MD 21629
  • 312 Fountain Ave, Denton, MD 21629
    312 Fountain Ave, Denton, MD 21629
    312 Fountain Ave, Denton, MD 21629
    /38

    $245,000 Sold Nov 14, 2025

    312 Fountain Ave, Denton, MD 21629

    • 3 Beds
    • 1.5 Baths
    • 1,092 Sq Ft
    • Built 1982

    Last Sold Summary

    • $224/SF
    • 72 Days On Market

    Last Listing Agent Pamela Ackermann-Doll RE/MAX Executive

    312 Fountain Ave, Denton, MD 21629
    • 108 Roe St, Greensboro, MD 21639
      108 Roe St, Greensboro, MD 21639
      108 Roe St, Greensboro, MD 21639
      /8

      Est $185,526 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 845 Sq Ft

      108 Roe St, Greensboro, MD 21639

      108 Roe St, Greensboro, MD 21639
  • 24872 Meeting House Rd, Denton, MD 21629
    24872 Meeting House Rd, Denton, MD 21629
    24872 Meeting House Rd, Denton, MD 21629
    /73

    $175,000 Pending

    • 3 Beds
    • 1 Bath
    • 1,763 Sq Ft

    24872 Meeting House Rd, Denton, MD 21629

    Own your own vacation home only a short distnce to Ocean City Md. and Rehoboth Beach. The renovation process has been started and you are just in time to choose your own finishes. Have you ever wanted to have your very own AirBNB or vacation home for your family and friends? From here you can walk to the Choptank River where you can fish, enjoy a nice picnic area or you can bring your boat down

    Saad Jamil Samson Properties

    24872 Meeting House Rd, Denton, MD 21629

Showing Results 201 - 240, Page 6 of 18

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