15,718

Caroline County, MD Homes

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  • /49

    $259,900

    $65K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,448 Sq Ft

    522 Market St, Denton, MD 21629

    Investor special in the heart of Denton! This duplex at 522 Market St offers incredible potential for the right buyer looking to add value and build equity. Featuring two separate units, each level includes 2 bedrooms and 1 full bathroom, providing a functional layout ideal for rental income or multi-generational living. This also has potential to be converted back into a single family

    Mike Lee Elmore EXP Realty, LLC

    522 Market St, Denton, MD 21629
  • /37

    $295,000

    Sold Apr 10, 2026

    1106 Osprey Ln, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 1,752 Sq Ft
    • Built 2004

    Last Sold Summary

    • $168/SF
    • 15 Days On Market

    Current Estimated Value $296,997

    Last Listing Agent Barbara McCaffrey Redfin Corp

    1106 Osprey Ln, Denton, MD 21629
    • /17

      Est $290,686

      Not Listed For Sale

      104 Noble Ave, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,236 Sq Ft
      • Built 1995
      104 Noble Ave, Preston, MD 21655

      Last Sold Summary

      • 76 Days On Market

  • /23

    $295,990

    New Construction $8K PRICE INCREASE Pending
    • 3 Beds
    • 2 Baths
    • 1,219 Sq Ft

    101 Parkland Rd, Greensboro, MD 21639

    Welcome to 101 Parkland Road, where a new move-in ready home can be yours in Kinnamon Meadows in Greensboro, MD. The Sullivan is a charming 1,219-square-foot, cottage-style ranch home featuring three bedrooms, two bathrooms, and a one-car garage. Just off the foyer, two spacious guest bedrooms and a shared full bathroom offer comfort and privacy for family or visitors. The open-concept kitchen

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

    101 Parkland Rd, Greensboro, MD 21639
  • /23

    $286,990

    Sold Feb 06, 2026

    133 Hobbs St, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,219 Sq Ft
    • Built 2025

    Last Sold Summary

    • $235/SF
    • 36 Days On Market

    Last Listing Agent Justin Wood D.R. Horton Realty of Virginia, LLC

    133 Hobbs St, Greensboro, MD 21639
    • /14

      Est $374,602

      Not Listed For Sale

      111 Fooks Ave, Preston, MD 21655

      • 4 Beds
      • 2 Baths
      • 2,072 Sq Ft
      • Built 1974
      111 Fooks Ave, Preston, MD 21655

      Last Sold Summary

      • 323 Days On Market

  • /34

    $260,000

    • 3 Beds
    • 2 Baths
    • 1,840 Sq Ft

    158 Wright St, Preston, MD 21655

    Step back in time with this charming 3-bedroom, 2-bathroom home built in 1890, located in the heart of Preston. Full of character and original details, this home offers a unique opportunity to restore and customize a piece of local history. The inviting living room features a cozy fireplace, perfect for relaxing evenings. A large laundry room and a separate den/office provide flexibility and

    Wes Russum Coldwell Banker Chesapeake Real Estate Company

    158 Wright St, Preston, MD 21655
  • /33

    $350,000

    Sold Sep 26, 2025

    24316 Auction Rd, Preston, MD 21655

    • 3 Beds
    • 1 Bath
    • 1,438 Sq Ft
    • Built 1975

    Last Sold Summary

    • $243/SF
    • 19 Days On Market

    Current Estimated Value $341,856

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    24316 Auction Rd, Preston, MD 21655
    • /14

      Est $384,493

      Not Listed For Sale

      107 Fooks Ave, Preston, MD 21655

      • 4 Beds
      • 2.5 Baths
      • 1,950 Sq Ft
      • Built 2023
      107 Fooks Ave, Preston, MD 21655

      Last Sold Summary

      • 154 Days On Market

  • /48

    $324,999

    • 3 Beds
    • 2 Baths
    • 2,079 Sq Ft

    129 Bloomingdale Ave, Federalsburg, MD 21632

    Welcome home to this beautifully updated 3-bedroom, 2-bath ranch offering over 2,000 square feet of comfortable living space. Thoughtfully improved throughout, this home features stylish board-and-batten accents, quartz countertops, and a functional layout designed for everyday living and entertaining. Enjoy generous-sized bedrooms, a spacious second living area, and plenty of room to spread out.

    Beverly Brown Coldwell Banker Realty

    129 Bloomingdale Ave, Federalsburg, MD 21632
  • /26

    $475,000

    Sold Oct 15, 2025

    4631 Everlea Ct, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 2,228 Sq Ft
    • Built 1997

    Last Sold Summary

    • $213/SF
    • 4 Days On Market

    Current Estimated Value $467,686

    Last Listing Agent Elizabeth Tryon Coldwell Banker Realty

    4631 Everlea Ct, Preston, MD 21655
    • /37

      Est $394,146

      Not Listed For Sale

      1103 Trice Meadows Cir, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 2,816 Sq Ft
      • Built 2010
      1103 Trice Meadows Cir, Denton, MD 21629

      Last Sold Summary

      • 3 Days On Market

  • /19

    $195,000

    • 2 Beds
    • 2 Baths
    • 884 Sq Ft

    112 Vernon Ave, Federalsburg, MD 21632

    NEWLY RENOVATED HOME ON CORNER LOT!!! NEW ROOF!!! NEW WINDOWS!!! NEW HVAC!!!! NEW FLOORING THROUGHOUT!!! NEW KITCHEN CABINETS!!! NEW STAINLESS APPLIANCES!!! NEW GRANITE COUNTERTOPS!!! TWO COMPLETELY NEW RENOVATED BATHROOMS!!! WASHER/DRYER!!! LARGE DECK OFF THE KITCHEN!!! TWO SHEDS!!! GO SEE THIS HOME TODAY!!!

    Sharon Burkhardt Douglas Realty, LLC

    112 Vernon Ave, Federalsburg, MD 21632
  • /21

    $59,900

    Sold Nov 24, 2025

    125 Bloomingdale Ave, Federalsburg, MD 21632

    • 4 Beds
    • 1 Bath
    • 1,696 Sq Ft
    • Built 1875

    Last Sold Summary

    • $35/SF
    • 22 Days On Market

    Current Estimated Value $145,710

    Last Listing Agent Daniel Demers Sell Your Home Services

    125 Bloomingdale Ave, Federalsburg, MD 21632
    • /19

      Est $357,622

      Not Listed For Sale

      344 Meadow Vale Ln, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,580 Sq Ft
      • Built 2010
      344 Meadow Vale Ln, Denton, MD 21629

      Last Sold Summary

      • 52 Days On Market

  • /27

    $334,000

    $15K PRICE DROP Under Contract
    • 3 Beds
    • 1.5 Baths
    • 1,622 Sq Ft

    207 S 7th St, Denton, MD 21629

    3BR, 1.5BA home on LARGE in town lot featuring Corian countertops, hardwood floors and built-in bookshelves. Enjoy a welcoming front porch and screened breezeway connecting a 2 car attached garage with additional lean-to storage. Roof replaced 2021. Full Walkout Dry basement with French drain and sump pump. Convenient in town location close to local amenities, all that is missing is your car in

    Amy Betts Coldwell Banker Realty

    207 S 7th St, Denton, MD 21629
  • /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 $220,927

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

    143 Riverwalk Terrace, Federalsburg, MD 21632
    • /13

      Est $281,438

      Not Listed For Sale

      12185 River Rd, Ridgely, MD 21660

      • 2 Beds
      • 1 Bath
      • 1,026 Sq Ft
      • Built 1990
      12185 River Rd, Ridgely, MD 21660

      Last Sold Summary

      • 5 Days On Market

  • /23

    $295,000

    $14K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    505 Maryland Ave, Ridgely, MD 21660

    Welcome to 505 Maryland Ave in the heart of charming Ridgely! This beautifully remodeled 3-bedroom, 2-bath rancher is truly move-in ready and offers the perfect blend of modern updates and everyday comfort. Renovated just a few years ago, the home features luxury vinyl plank flooring throughout, stylish soft-close cabinetry, granite countertops, stainless steel appliances, and a bright,

    Heather Brummell Keller Williams Realty

    505 Maryland Ave, Ridgely, MD 21660
  • /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 $382,998

    Last Listing Agent Sean O'Connor Coldwell Banker Realty

    11145 Branch Ct, Denton, MD 21629
    • /12

      Est $1,149,822

      Not Listed For Sale

      12786 Holly Rd, Greensboro, MD 21639

      • 2 Beds
      • 1 Bath
      • 1,728 Sq Ft
      • Built 1870
      12786 Holly Rd, Greensboro, MD 21639

      Last Sold Summary

      • 60 Days On Market

  • /59

    $465,000

    $10K PRICE DROP
    • 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
  • /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 $245,326

    Last Listing Agent Barbara Beaudet Brenton Realty Group

    505 Market St, Denton, MD 21629
    • /12

      Est $378,199

      Not Listed For Sale

      1108 Trice Meadows Cir, Denton, MD 21629

      • 4 Beds
      • 2 Baths
      • 1,500 Sq Ft
      • Built 2023
      1108 Trice Meadows Cir, Denton, MD 21629

      Last Sold Summary

      • 147 Days On Market

  • /54

    $395,000

    $30K PRICE DROP Under Contract
    • 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
  • /22

    $457,500

    Sold Apr 09, 2026

    0 Dover Bridge Rd Unit MDCM2005586, Preston, MD 21655

    • Land
    • 63.16 Acres
    • $7,244 per Acre

    Last Sold Summary

    • 338 Days On Market

    Last Listing Agent Coard Benson Benson & Mangold, LLC

    0 Dover Bridge Rd Unit MDCM2005586, Preston, MD 21655
    • /17

      Est $172,777

      Not Listed For Sale

      21781 Wood Wharf Rd, Preston, MD 21655

      • 2 Beds
      • 1 Bath
      • 924 Sq Ft
      • Built 1920
      21781 Wood Wharf Rd, Preston, MD 21655

      Last Sold Summary

      • 102 Days On Market

  • /18

    $1,500,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,674 Sq Ft

    0 Cool Spring Rd Unit MDCM2006846, Marydel, MD 21649

    Cool Spring Poultry Farm is a well-maintained three-house poultry operation situated on approximately 25.8 acres in northern Caroline County, Maryland. The farm is currently under contract with Amick, and the owner has consistently ranked among the top growers. Each of the three 60' x 500' poultry houses was built in 2006 and has seen numerous recent upgrades, including Rotem controllers with

    Nick Campanaro The Land Group

    0 Cool Spring Rd Unit MDCM2006846, Marydel, MD 21649
  • /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
    • /74

      Not Listed For Sale

      4439 Bethlehem Rd, Preston, MD 21655

      • 5 Beds
      • 2.5 Baths
      • 2,560 Sq Ft
      • Built 1900
      4439 Bethlehem Rd, Preston, MD 21655

      Last Sold Summary

      • 106 Days On Market

  • /4

    $20,000

    • Land
    • 21,780 Sq Ft
    • $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
  • /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 $283,090

    Last Listing Agent Andrew Beaven Wright Real Estate

    5059 Gina Ln, Federalsburg, MD 21632
    • /48

      Est $336,795

      Not Listed For Sale

      6 Maple Ave, Ridgely, MD 21660

      • 4 Beds
      • 2 Baths
      • 2,492 Sq Ft
      • Built 1957
      6 Maple Ave, Ridgely, MD 21660

      Last Sold Summary

      • 11 Days On Market

  • /23

    $230,000

    • 2 Beds
    • 1 Bath
    • 1,108 Sq Ft

    3894 Old Denton Rd, Federalsburg, MD 21632

    Nestled in a quiet setting, 3894 Old Denton Rd is a charming rancher that offers the ease of true single-level living. The home features an inviting, open layout where a spacious living room leads into the kitchen and dining area, making it feel bright and connected. Two comfortable bedrooms are tucked away for privacy, while a bright sunroom, a covered front porch, and a rear screened porch

    Billy Mister Keller Williams Realty

    3894 Old Denton Rd, Federalsburg, MD 21632
  • /65

    $550,000

    Sold Jun 11, 2026

    322 Deep Shore Rd, Denton, MD 21629

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1982

    Last Sold Summary

    • 12% Below List Price
    • $409/SF
    • 21 Days On Market

    Current Estimated Value $605,350

    Last Listing Agent Connie Loveland Benson & Mangold, LLC

    322 Deep Shore Rd, Denton, MD 21629
    • /15

      Est $177,185

      Not Listed For Sale

      128 Bloomingdale Ave, Federalsburg, MD 21632

      • 5 Beds
      • 3.5 Baths
      • 4,316 Sq Ft
      • Built 1860
      128 Bloomingdale Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 245 Days On Market

  • /33

    $359,000

    $10K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,560 Sq Ft

    401 S 2nd St, Denton, MD 21629

    This charming 2-story colonial home in Denton offers a perfect blend of classic character and modern updates. Featuring 3 bedrooms and 11⁄2 bathrooms, this well-maintained home is conveniently located close to downtown, giving you easy access to local restaurants, shopping, and community events. Inside, you’ll find beautiful hardwood floors that add warmth and timeless appeal throughout much of

    Wes Russum Coldwell Banker Chesapeake Real Estate Company

    401 S 2nd St, Denton, MD 21629
  • /25

    $370,000

    Sold May 29, 2026

    23168 Deer Run Ct, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,380 Sq Ft
    • Built 2002

    Last Sold Summary

    • $268/SF
    • 3 Days On Market

    Current Estimated Value $377,675

    Last Listing Agent Brian Gearhart Benson & Mangold, LLC

    23168 Deer Run Ct, Denton, MD 21629
    • /31

      Est $392,389

      Not Listed For Sale

      5132 Clark Canning House Rd, Federalsburg, MD 21632

      • 4 Beds
      • 2.5 Baths
      • 2,200 Sq Ft
      • Built 1930
      5132 Clark Canning House Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 353 Days On Market

  • /5

    $900,000

    • Land
    • 26.15 Acres
    • $34,417 per Acre

    1017 Camp Rd, Denton, MD 21629

    Approximately 27.16 acres of development land located within the Town of Denton. The property is currently zoned UR (Urban Residential). Public water and sewer are available in the area; purchasers should independently verify utility capacity, connection requirements, and all development approvals with the Town of Denton and Caroline County. The property is being offered for sale as raw land. A

    Benjamin Alder The Land Group

    1017 Camp Rd, Denton, MD 21629

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