15,675

Caroline County, MD Homes

Section Image Section Image
  • 406 Morning Glory Dr, Denton, MD 21629
    406 Morning Glory Dr, Denton, MD 21629
    406 Morning Glory Dr, Denton, MD 21629
    /50

    $399,000

    • 4 Beds
    • 2.5 Baths
    • 2,731 Sq Ft

    406 Morning Glory Dr, Denton, MD 21629

    SUPER PRICE IMPROVEMENT!! 2020-BUILT EASTERN SHORE COLONIAL. On the outskirts of historic Denton, you will find this 4-bedroom, 2.5 bathroom home in the pleasant neighborhood of “The Gardens!" This one-owner home offers high-end detailing including a fresh decorator neutral paint palette, free-flowing open concept floor plan, beautiful NEW carpeting, as well as luxury vinyl tile flooring, a

    Mary Stevens Long & Foster Real Estate, Inc.

    406 Morning Glory Dr, Denton, MD 21629
  • 1111 Daylily Ln, Denton, MD 21629
    1111 Daylily Ln, Denton, MD 21629
    1111 Daylily Ln, Denton, MD 21629
    /26

    $402,000 Sold Dec 09, 2025

    1111 Daylily Ln, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 3,838 Sq Ft
    • Built 2007

    Last Sold Summary

    • $105/SF
    • 7 Days On Market

    Last Listing Agent Terri Murray RE/MAX Executive

    1111 Daylily Ln, Denton, MD 21629
    • 4845 Houston Branch Rd, Federalsburg, MD 21632
      4845 Houston Branch Rd, Federalsburg, MD 21632
      4845 Houston Branch Rd, Federalsburg, MD 21632
      /16

      Est $168,100 Not Listed For Sale

      4845 Houston Branch Rd, Federalsburg, MD 21632

      4845 Houston Branch Rd, Federalsburg, MD 21632
  • 406 Wood Duck Dr, Greensboro, MD 21639
    406 Wood Duck Dr, Greensboro, MD 21639
    406 Wood Duck Dr, Greensboro, MD 21639
    /41

    $319,900 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,364 Sq Ft

    406 Wood Duck Dr, Greensboro, MD 21639

    MOTIVATED SELLER! Schedule and tour, fall in love, and write an offer! Featuring a traditional two story floor plan, this home welcomes you from the start. This 3 bedroom, and 2.5 bathroom home offers a move in ready space to make your own! As you enter you’ll love the newer vinyl plank flooring throughout the main level, with fresh paint. The family room, and near by dining room gives ample

    Brittany Gough RE/MAX One

    406 Wood Duck Dr, Greensboro, MD 21639
  • 12400 & 12316 Ridgely Rd, Greensboro, MD 21639
    12400 & 12316 Ridgely Rd, Greensboro, MD 21639
    12400 & 12316 Ridgely Rd, Greensboro, MD 21639
    /14

    $2,000,000 Sold Mar 21, 2025

    12400 & 12316 Ridgely Rd, Greensboro, MD 21639

    • 3 Beds
    • 1 Bath
    • 1,896 Sq Ft
    • Built 1975

    Last Sold Summary

    • $1,055/SF
    • 7 Days On Market

    Last Listing Agent BRIAN MORRIS The Land Group

    12400 & 12316 Ridgely Rd, Greensboro, MD 21639
    • 712 Gay St, Denton, MD 21629
      712 Gay St, Denton, MD 21629
      712 Gay St, Denton, MD 21629
      /13

      Not Listed For Sale

      • Studio
      • 2,184 Sq Ft

      712 Gay St, Denton, MD 21629

      712 Gay St, Denton, MD 21629
  • 1302 Trice Meadows Cir, Denton, MD 21629
    1302 Trice Meadows Cir, Denton, MD 21629
    1302 Trice Meadows Cir, Denton, MD 21629
    /22

    $399,000

    • 3 Beds
    • 2 Baths
    • 2,412 Sq Ft

    1302 Trice Meadows Cir, Denton, MD 21629

    Lovely Raised Rancher consisting of 2,412 square feet of living with the main level having 3 bedrooms, 2 bathrooms, office/den, living room, kitchen and laundry area with a split floor plan of the bedrooms and the owner's suite on the opposite end of house. No worries about parking your vehicles with this nice 2 car attached garage and on street parking. Additionally, the second floor 52x15 bonus

    George Thompson Long & Foster Real Estate, Inc.

    1302 Trice Meadows Cir, Denton, MD 21629
  • 123 Briarwood Cir, Denton, MD 21629
    123 Briarwood Cir, Denton, MD 21629
    123 Briarwood Cir, Denton, MD 21629
    /30

    $340,000 Sold Aug 20, 2025

    123 Briarwood Cir, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft
    • Built 2015

    Last Sold Summary

    • $170/SF
    • 64 Days On Market

    Current Estimated Value $355,308

    Last Listing Agent Lou Chirgott Core Maryland Real Estate LLC

    123 Briarwood Cir, Denton, MD 21629
    • 21994 Main St, Hillsboro, MD 21641
      21994 Main St, Hillsboro, MD 21641
      21994 Main St, Hillsboro, MD 21641
      /29

      Est $319,827 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 4,000 Sq Ft

      21994 Main St, Hillsboro, MD 21641

      21994 Main St, Hillsboro, MD 21641
  • 208 Oriole Ave, Ridgely, MD 21660
    208 Oriole Ave, Ridgely, MD 21660
    208 Oriole Ave, Ridgely, MD 21660
    /28

    $339,000

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

    208 Oriole Ave, Ridgely, MD 21660

    Come see this Beautiful well maintained Ranch home in the heart of Ridgely. The house is a block away from the local park. The house has had many upgrades including an addition in 2020. New siding in 2020. New deck after 2020. New windows in 2017. There are solar panels on the roof. Spacious back yard with a patio. Many other upgrades to come and see.

    Rachel Penska Long & Foster Real Estate, Inc.

    208 Oriole Ave, Ridgely, MD 21660
  • 504 Pintail St, Greensboro, MD 21639
    504 Pintail St, Greensboro, MD 21639
    504 Pintail St, Greensboro, MD 21639
    /26

    $295,000 Sold Dec 30, 2025

    504 Pintail St, Greensboro, MD 21639

    • 3 Beds
    • 2.5 Baths
    • 1,664 Sq Ft
    • Built 2024

    Last Sold Summary

    • $177/SF
    • 133 Days On Market

    Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

    504 Pintail St, Greensboro, MD 21639
    • 5 Seward Rd, Ridgely, MD 21660
      5 Seward Rd, Ridgely, MD 21660
      5 Seward Rd, Ridgely, MD 21660
      /24

      Est $355,621 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,538 Sq Ft

      5 Seward Rd, Ridgely, MD 21660

      5 Seward Rd, Ridgely, MD 21660
  • 1111 Ruddy Duck Ct, Denton, MD 21629
    1111 Ruddy Duck Ct, Denton, MD 21629
    1111 Ruddy Duck Ct, Denton, MD 21629
    /49

    $389,900 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,670 Sq Ft

    1111 Ruddy Duck Ct, Denton, MD 21629

    I’m thrilled to introduce you to this absolutely stunning home, perfectly situated on a private lot and surrounded by mature trees and vibrant landscaping! The updated kitchen is a true gem, featuring solid surface countertops and a charming tile backsplash—it's an inviting space that's perfect for both cooking and entertaining! You’re going to fall in love with the spacious master suite, which

    Lee Wolff FSBO Broker

    1111 Ruddy Duck Ct, Denton, MD 21629
  • 0 Temple Rd Unit MDCM2006034, Marydel, MD 21649
    0 Temple Rd Unit MDCM2006034, Marydel, MD 21649
    0 Temple Rd Unit MDCM2006034, Marydel, MD 21649
    /18

    $475,000 Sold Dec 22, 2025

    0 Temple Rd Unit MDCM2006034, Marydel, MD 21649

    • Land
    • 53.01 Acres
    • $8,961 per Acre

    Last Sold Summary

    • 140 Days On Market

    Last Listing Agent Benjamin Alder The Land Group

    0 Temple Rd Unit MDCM2006034, Marydel, MD 21649
    • 328 E Central Ave, Federalsburg, MD 21632
      328 E Central Ave, Federalsburg, MD 21632
      328 E Central Ave, Federalsburg, MD 21632
      /5

      Est $86,667 Not Listed For Sale

      328 E Central Ave, Federalsburg, MD 21632

      328 E Central Ave, Federalsburg, MD 21632
  • 1107 Osprey Ln, Denton, MD 21629
    1107 Osprey Ln, Denton, MD 21629
    1107 Osprey Ln, Denton, MD 21629
    /31

    $379,900

    • 4 Beds
    • 2.5 Baths
    • 2,132 Sq Ft

    1107 Osprey Ln, Denton, MD 21629

    This well maintained 4 bedroom 2.5 bath home in the excellent community setting of Mallard Landing is ready for its new owners! This 2000 sq ft property features a partially fenced yard with a lovely patio/firepit area and plenty of room for gardening, fresh cabinets & counter tops, built in electric fireplaces throughout, new washer & dryer, oversized attached 2 car garage currently set up as a

    Megan Rosendale Rosendale Realty

    1107 Osprey Ln, Denton, MD 21629
  • 3069 Choptank Rd, Preston, MD 21655
    3069 Choptank Rd, Preston, MD 21655
    3069 Choptank Rd, Preston, MD 21655
    /88

    $930,000 Sold Sep 30, 2025

    3069 Choptank Rd, Preston, MD 21655

    • 3 Beds
    • 2.5 Baths
    • 2,512 Sq Ft
    • Built 2003

    Last Sold Summary

    • $370/SF
    • 11 Days On Market

    Current Estimated Value $947,146

    Last Listing Agent Eddie Matthews Benson & Mangold, LLC

    3069 Choptank Rd, Preston, MD 21655
    • 26302 Sennett Rd, Denton, MD 21629
      26302 Sennett Rd, Denton, MD 21629
      26302 Sennett Rd, Denton, MD 21629
      /5

      Est $63,045 Not Listed For Sale

      26302 Sennett Rd, Denton, MD 21629

      26302 Sennett Rd, Denton, MD 21629
  • 22403 Marsh Creek Rd, Preston, MD 21655
    22403 Marsh Creek Rd, Preston, MD 21655
    22403 Marsh Creek Rd, Preston, MD 21655
    /35

    $384,900

    • 3 Beds
    • 2 Baths
    • 1,448 Sq Ft

    22403 Marsh Creek Rd, Preston, MD 21655

    Custom Brick rancher, close to town on large lot. Open floor plan, spacious kitchen, stainless steel appliances, large island. 3 bedrooms, 2 baths, sunroom overlooking yard. Upgrades include new windows, CAC, new roof new electric service and plumbing New Septic and Well, Closing help will be considered

    Barbara Nichols Results Realty Inc.

    22403 Marsh Creek Rd, Preston, MD 21655
  • 3622 Choptank Rd, Preston, MD 21655
    3622 Choptank Rd, Preston, MD 21655
    3622 Choptank Rd, Preston, MD 21655
    /44

    $295,900 Sold Dec 31, 2025

    3622 Choptank Rd, Preston, MD 21655

    • 2 Beds
    • 1.5 Baths
    • 1,700 Sq Ft
    • Built 1961

    Last Sold Summary

    • $174/SF
    • 2 Days On Market

    Last Listing Agent Brooke Tephabock VYBE Realty

    3622 Choptank Rd, Preston, MD 21655
    • 13056 Hog Lot Rd, Ridgely, MD 21660
      13056 Hog Lot Rd, Ridgely, MD 21660
      13056 Hog Lot Rd, Ridgely, MD 21660
      /79

      Est $565,748 Not Listed For Sale

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

      13056 Hog Lot Rd, Ridgely, MD 21660

      13056 Hog Lot Rd, Ridgely, MD 21660
  • 27279 Jenny Hye Ln, Marydel, MD 21649
    27279 Jenny Hye Ln, Marydel, MD 21649
    27279 Jenny Hye Ln, Marydel, MD 21649
    /8

    $355,000

    • 3 Beds
    • 2.5 Baths
    • 2,286 Sq Ft

    27279 Jenny Hye Ln, Marydel, MD 21649

    Welcome to Your Peaceful Retreat!This 3-bedroom, 2.5-bath split-foyer home offers 1,488 sq. ft. of comfortable living space, plus a full basement and an attached one-car garage. With its classic brick-and-siding exterior, inviting front patio, and serene surroundings, this property blends warmth, character, and endless potential.Step inside and imagine the possibilities—a bright, open

    Hudson Post Keller Williams Select Realtors of Easton

    27279 Jenny Hye Ln, Marydel, MD 21649
  • 17 Greenridge Ave, Ridgely, MD 21660
    17 Greenridge Ave, Ridgely, MD 21660
    17 Greenridge Ave, Ridgely, MD 21660
    /16

    $265,000 Sold Jul 31, 2025

    17 Greenridge Ave, Ridgely, MD 21660

    • 3 Beds
    • 1 Bath
    • 1,136 Sq Ft
    • Built 1991

    Last Sold Summary

    • $233/SF
    • 7 Days On Market

    Current Estimated Value $281,396

    Last Listing Agent Mary Mabry Keller Williams Select Realtors of Cambridge

    17 Greenridge Ave, Ridgely, MD 21660
    • 21373 Dover Bridge Rd, Preston, MD 21655
      21373 Dover Bridge Rd, Preston, MD 21655
      21373 Dover Bridge Rd, Preston, MD 21655
      /5

      Est $108,075 Not Listed For Sale

      21373 Dover Bridge Rd, Preston, MD 21655

      21373 Dover Bridge Rd, Preston, MD 21655
  • 3 Sunrise Ave, Ridgely, MD 21660
    3 Sunrise Ave, Ridgely, MD 21660
    3 Sunrise Ave, Ridgely, MD 21660
    /22

    $369,000 New Construction

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

    3 Sunrise Ave, Ridgely, MD 21660

    ***New Construction - Under Construction now with estimated completion of April 2026. Photos are of model previously built.*** This modern "Farmhouse" Rancher is thoughtfully designed and constructed by the reputable Lomaxx Custom Homes, offering the perfect combination of style, functionality, and comfort. This beautiful home features 3 bedrooms, 2 full bathrooms, and an inviting open-concept

    Amy Betts Coldwell Banker Realty

    3 Sunrise Ave, Ridgely, MD 21660
  • 614 Market St, Denton, MD 21629
    614 Market St, Denton, MD 21629
    614 Market St, Denton, MD 21629
    /29

    $325,000 Sold Oct 06, 2025

    614 Market St, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 2,508 Sq Ft
    • Built 1890

    Last Sold Summary

    • $130/SF
    • 53 Days On Market

    Current Estimated Value $326,499

    Last Listing Agent Michael Bozek Michael J. Bozek

    614 Market St, Denton, MD 21629
    • 21303 Dover Bridge Rd, Preston, MD 21655
      21303 Dover Bridge Rd, Preston, MD 21655
      21303 Dover Bridge Rd, Preston, MD 21655
      /39

      Est $392,624 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,607 Sq Ft

      21303 Dover Bridge Rd, Preston, MD 21655

      21303 Dover Bridge Rd, Preston, MD 21655
  • 25361 Calvert Dr, Greensboro, MD 21639
    25361 Calvert Dr, Greensboro, MD 21639
    25361 Calvert Dr, Greensboro, MD 21639
    /70

    $324,500 Under Contract

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

    25361 Calvert Dr, Greensboro, MD 21639

    Water privileged, privacy and lots of space, over 1,800 sqft with 3 bedrooms and 2 full baths. You won t want to miss this one. Lots of space for entertaining inside and out. Inside you will find new floors in kitchen and laundry room, recently purchased stainless appliances, fresh painted walls, updated bathroom, large open floor plan, and a sun room overlooking the large, fenced-in yard.

    Chris Rosendale CR Realty

    25361 Calvert Dr, Greensboro, MD 21639
  • 120 Parkland Rd, Greensboro, MD 21639
    120 Parkland Rd, Greensboro, MD 21639
    120 Parkland Rd, Greensboro, MD 21639
    /20

    $266,990 Sold Oct 10, 2025

    120 Parkland Rd, Greensboro, MD 21639

    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $252/SF
    • 24 Days On Market

    D.R. Horton Kinnamon Meadows

    120 Parkland Rd, Greensboro, MD 21639
    • 106 Noble Ave, Preston, MD 21655
      106 Noble Ave, Preston, MD 21655
      106 Noble Ave, Preston, MD 21655
      /23

      Est $324,698 Not Listed For Sale

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

      106 Noble Ave, Preston, MD 21655

      106 Noble Ave, Preston, MD 21655
  • 1 Oakview Ct, Ridgely, MD 21660
    1 Oakview Ct, Ridgely, MD 21660
    1 Oakview Ct, Ridgely, MD 21660
    /26

    $315,000

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

    1 Oakview Ct, Ridgely, MD 21660

    Well-maintained 3BR, 2BA home offering a functional layout with a cozy living room and an updated kitchen featuring stainless steel appliances. The primary bedroom includes a full bath, and the laundry/mudroom provides added practicality. Fresh paint throughout, plus a fenced yard, gazebo, and patio create inviting outdoor space. Recent improvements include solar panels (2018) and a new roof

    Peter Stark Benson & Mangold, LLC

    1 Oakview Ct, Ridgely, MD 21660
  • 517 Franklin St, Denton, MD 21629
    517 Franklin St, Denton, MD 21629
    517 Franklin St, Denton, MD 21629
    /22

    $275,000 Sold Mar 11, 2025

    517 Franklin St, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,080 Sq Ft
    • Built 1900

    Last Sold Summary

    • $255/SF
    • 108 Days On Market

    Current Estimated Value $290,856

    Last Listing Agent Amanda Morgan Brenton Realty Group

    517 Franklin St, Denton, MD 21629
    • 230 Main St, Preston, MD 21655
      230 Main St, Preston, MD 21655
      230 Main St, Preston, MD 21655
      /53

      Est $446,201 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 3,208 Sq Ft

      230 Main St, Preston, MD 21655

      230 Main St, Preston, MD 21655
  • 1 Sunrise Ave, Ridgely, MD 21660
    1 Sunrise Ave, Ridgely, MD 21660
    1 Sunrise Ave, Ridgely, MD 21660
    /28

    $399,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 1,768 Sq Ft

    1 Sunrise Ave, Ridgely, MD 21660

    As morning light rises over Sunrise Village, this home, The Sunshine, thoughtfully crafted by local builder Lomaxx Custom Homes comes to life. Golden light spills across the nearby fields and settles gently indoors, where days begin with coffee on the porch, birds gliding by, and daylight drifting through the windows, filling each room with a calm, welcoming glow. Designed for easy, everyday

    Crystal Smith RE/MAX Executive

    1 Sunrise Ave, Ridgely, MD 21660
  • 22490 Ash Blvd, Preston, MD 21655
    22490 Ash Blvd, Preston, MD 21655
    22490 Ash Blvd, Preston, MD 21655
    /46

    $348,000 Sold Oct 14, 2025

    22490 Ash Blvd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 2001

    Last Sold Summary

    • $188/SF
    • 22 Days On Market

    Last Listing Agent Kathryn Tennant Douglas Realty, LLC

    22490 Ash Blvd, Preston, MD 21655
    • 104 Noble Ave, Preston, MD 21655
      104 Noble Ave, Preston, MD 21655
      104 Noble Ave, Preston, MD 21655
      /17

      Est $303,771 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,236 Sq Ft

      104 Noble Ave, Preston, MD 21655

      104 Noble Ave, Preston, MD 21655
  • 0 Quail Ct Unit MDCM2006742, Greensboro, MD 21639
    0 Quail Ct Unit MDCM2006742, Greensboro, MD 21639
    0 Quail Ct Unit MDCM2006742, Greensboro, MD 21639
    /15

    $409,000 New Construction

    • 3 Beds
    • 2 Baths

    0 Quail Ct Unit MDCM2006742, Greensboro, MD 21639

    TBB....This beautifully designed rancher offers 3 bedrooms and 2 full baths with an open-concept floor plan and cathedral ceilings in the main living area. The builder includes a generous package of upgrades at no additional cost. Enjoy an oversized attached two-car garage and a rear deck perfect for outdoor living. Situated on a cleared 1-acre lot in a private rural setting, this home offers the

    Barbara Blosser Long & Foster Real Estate, Inc.

    0 Quail Ct Unit MDCM2006742, Greensboro, MD 21639
  • 3457 Jefferson Pond Rd, Federalsburg, MD 21632
    3457 Jefferson Pond Rd, Federalsburg, MD 21632
    3457 Jefferson Pond Rd, Federalsburg, MD 21632
    /21

    $297,500 Sold Apr 07, 2025

    3457 Jefferson Pond Rd, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2024

    Last Sold Summary

    • $221/SF
    • 145 Days On Market

    Last Listing Agent Amy Herr Keller Williams Realty

    3457 Jefferson Pond Rd, Federalsburg, MD 21632
    • 240 Main St, Preston, MD 21655
      240 Main St, Preston, MD 21655
      240 Main St, Preston, MD 21655
      /60

      Est $361,852 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,088 Sq Ft

      240 Main St, Preston, MD 21655

      240 Main St, Preston, MD 21655
  • 501 Lincoln St, Denton, MD 21629
    501 Lincoln St, Denton, MD 21629
    501 Lincoln St, Denton, MD 21629
    /15

    $135,000

    • 3 Beds
    • 1.5 Baths
    • 1,664 Sq Ft

    501 Lincoln St, Denton, MD 21629

    Property is being sold As/ Is. Located on a corner lot. Owner has completed some work to the property, but additional work will be required. Please contact Denton Planning and Codes to verify remaining requirements to obtain an occupancy permit.

    Diane Wenk Wright Real Estate

    501 Lincoln St, Denton, MD 21629

Showing Results 81 - 120, Page 3 of 18

Maryland Caroline County

Real Estate & Homes

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

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group