15,671

Caroline County, MD Homes

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    • 24251 Willow Pond Rd, Denton, MD 21629
      24251 Willow Pond Rd, Denton, MD 21629
      24251 Willow Pond Rd, Denton, MD 21629
      /71

      Est $586,685 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,813 Sq Ft

      24251 Willow Pond Rd, Denton, MD 21629

      24251 Willow Pond Rd, Denton, MD 21629
  • 207 Bloomingdale Ave, Federalsburg, MD 21632
    207 Bloomingdale Ave, Federalsburg, MD 21632
    207 Bloomingdale Ave, Federalsburg, MD 21632
    /43

    $247,500

    • 3 Beds
    • 2 Baths
    • 1,684 Sq Ft

    207 Bloomingdale Ave, Federalsburg, MD 21632

    Discover this inviting 3-bedroom, 2-bath home on a 0.27-acre lot in the heart of Federalsburg. Enter to a spacious living room filled with natural light and a cozy fireplace, perfect for relaxing or entertaining. Adjacent, the family room features stunning wood-paneled walls, built-in shelving, a second fireplace, and access to both the outdoors and the kitchen and dining areas, creating a

    Dustin Parker The Parker Group

    207 Bloomingdale Ave, Federalsburg, MD 21632
  • 148 Main St, Preston, MD 21655
    148 Main St, Preston, MD 21655
    148 Main St, 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

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

    148 Main St, Preston, MD 21655
    • 1702 Cattail Commons Way, Denton, MD 21629
      1702 Cattail Commons Way, Denton, MD 21629
      1702 Cattail Commons Way, Denton, MD 21629
      /22

      Est $451,632 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,096 Sq Ft

      1702 Cattail Commons Way, Denton, MD 21629

      1702 Cattail Commons Way, Denton, MD 21629
  • 132 Hobbs St, Greensboro, MD 21639
    132 Hobbs St, Greensboro, MD 21639
    132 Hobbs St, Greensboro, MD 21639
    /20

    $268,490 New Construction

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

    132 Hobbs St, Greensboro, MD 21639

    Discover the Perry in Kinnamon Meadows, a 1,059 square foot open concept cottage-style ranch home, offering two bedrooms and two bathrooms at 132 Hobbs Street in Greensboro, MD. A welcoming front porch leads you into the spacious living room that seamlessly flows into the kitchen, creating a perfect space for entertaining guests or enjoying family time. The well-equipped kitchen is complete with

    D.R. Horton Builder
    132 Hobbs St, Greensboro, MD 21639
  • 510 Pintail St, Greensboro, MD 21639
    510 Pintail St, Greensboro, MD 21639
    510 Pintail St, Greensboro, MD 21639
    /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 $362,613

    Last Listing Agent Jon Fleming Weichert Realtors - Blue Ribbon

    510 Pintail St, Greensboro, MD 21639
    • 120 Denton Rd, Federalsburg, MD 21632
      120 Denton Rd, Federalsburg, MD 21632
      120 Denton Rd, Federalsburg, MD 21632
      /5

      Est $43,000 Not Listed For Sale

      120 Denton Rd, Federalsburg, MD 21632

      120 Denton Rd, Federalsburg, MD 21632
  • 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
  • 512 Lincoln St, Denton, MD 21629
    512 Lincoln St, Denton, MD 21629
    512 Lincoln St, Denton, MD 21629
    /20

    $294,000 Sold Oct 24, 2025

    512 Lincoln St, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,420 Sq Ft
    • Built 2024

    Last Sold Summary

    • $207/SF
    • 28 Days On Market

    Last Listing Agent Amy Betts Coldwell Banker Realty

    512 Lincoln St, Denton, MD 21629
    • 4191 Harmony Rd, Preston, MD 21655
      4191 Harmony Rd, Preston, MD 21655
      4191 Harmony Rd, Preston, MD 21655
      /18

      Est $529,679 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,196 Sq Ft

      4191 Harmony Rd, Preston, MD 21655

      4191 Harmony Rd, Preston, MD 21655
  • 123 Parkland Rd, Greensboro, MD 21639
    123 Parkland Rd, Greensboro, MD 21639
    /2

    $274,990 Pending

    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft

    123 Parkland Rd, Greensboro, MD 21639

    Explore 123 Parkland Road, a new home under-construction in the quaint Kinnamon Meadows community of Greensboro, MD. The Curtis is a 1,182 square foot, cottage-style ranch home with three bedrooms and two bathrooms. As you enter the home through the front porch, this thoughtfully designed home has a grand open concept living area that leads into the spacious kitchen. To the right, a long, main

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

    123 Parkland Rd, Greensboro, MD 21639
  • 22716 Havercamp Rd, Preston, MD 21655
    22716 Havercamp Rd, Preston, MD 21655
    22716 Havercamp Rd, Preston, MD 21655
    /33

    $435,000 Sold Aug 29, 2025

    22716 Havercamp Rd, Preston, MD 21655

    • 3 Beds
    • 2.5 Baths
    • 2,192 Sq Ft
    • Built 2007

    Last Sold Summary

    • $198/SF
    • 72 Days On Market

    Current Estimated Value $459,426

    Last Listing Agent Chuck Mangold Benson & Mangold, LLC

    22716 Havercamp Rd, Preston, MD 21655
    • 1306 Chesapeake Dr, Denton, MD 21629
      1306 Chesapeake Dr, Denton, MD 21629
      1306 Chesapeake Dr, Denton, MD 21629
      /13

      Est $351,556 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,654 Sq Ft

      1306 Chesapeake Dr, Denton, MD 21629

      1306 Chesapeake Dr, Denton, MD 21629
  • 4218 Harmony Rd, Preston, MD 21655
    4218 Harmony Rd, Preston, MD 21655
    4218 Harmony Rd, Preston, MD 21655
    /127

    $2,999,000

    • 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
  • 305 Maple Ave, Federalsburg, MD 21632
    305 Maple Ave, Federalsburg, MD 21632
    305 Maple Ave, Federalsburg, MD 21632
    /18

    $169,900 Sold Mar 21, 2025

    305 Maple Ave, Federalsburg, MD 21632

    • 3 Beds
    • 1 Bath
    • 1,392 Sq Ft
    • Built 1940

    Last Sold Summary

    • $122/SF
    • 43 Days On Market

    Current Estimated Value $180,954

    Last Listing Agent Traci Jordan Meredith Fine Properties

    305 Maple Ave, Federalsburg, MD 21632
    • 5576 Harmony Woods Dr, Preston, MD 21655
      5576 Harmony Woods Dr, Preston, MD 21655
      5576 Harmony Woods Dr, Preston, MD 21655
      /27

      Est $436,403 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,700 Sq Ft

      5576 Harmony Woods Dr, Preston, MD 21655

      5576 Harmony Woods Dr, Preston, MD 21655
  • 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
  • 104 Sunset Blvd, Ridgely, MD 21660
    104 Sunset Blvd, Ridgely, MD 21660
    104 Sunset Blvd, Ridgely, MD 21660
    /28

    $275,000 Sold Jul 08, 2025

    104 Sunset Blvd, Ridgely, MD 21660

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft
    • Built 1992

    Last Sold Summary

    • $273/SF
    • 215 Days On Market

    Current Estimated Value $288,236

    Last Listing Agent Marcia Rostien Long & Foster Real Estate, Inc.

    104 Sunset Blvd, Ridgely, MD 21660
    • 27105 River Bridge Rd, Henderson, MD 21640
      27105 River Bridge Rd, Henderson, MD 21640
      27105 River Bridge Rd, Henderson, MD 21640
      /6

      Est $70,590 Not Listed For Sale

      27105 River Bridge Rd, Henderson, MD 21640

      27105 River Bridge Rd, Henderson, MD 21640
  • 8548 Dogwood Blossom Ln, Denton, MD 21629
    8548 Dogwood Blossom Ln, Denton, MD 21629
    8548 Dogwood Blossom Ln, Denton, MD 21629
    /46

    $394,000

    • 4 Beds
    • 2.5 Baths
    • 2,176 Sq Ft

    8548 Dogwood Blossom Ln, Denton, MD 21629

    Welcome to this well maintained Colonial on a very private road. Home only needs a little updating. Bones are Great! Home features 3 Large Bedrooms upsatirs with a Full bath in hallway. 1 Very Spacious Primary Bedroom with Two closets and a Full Bath. Downstairs you will enjoy ALL the space. Lovely Eat-in Kitchen, Separate Dining Room, Family Room w/ Wood Stove, Living Room, Laundry Room and HUGE

    Kathleen Brenton Brenton Realty Group

    8548 Dogwood Blossom Ln, Denton, MD 21629
  • 110 Parkland Rd, Greensboro, MD 21639
    110 Parkland Rd, Greensboro, MD 21639
    /2

    $286,990 Sold Aug 15, 2025

    110 Parkland Rd, Greensboro, MD 21639

    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft
    • Built 2025

    Last Sold Summary

    • $197/SF
    • 7 Days On Market

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

    110 Parkland Rd, Greensboro, MD 21639
    • 26062 Holly Ln, Greensboro, MD 21639
      26062 Holly Ln, Greensboro, MD 21639
      26062 Holly Ln, Greensboro, MD 21639
      /32

      Est $408,871 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,798 Sq Ft

      26062 Holly Ln, Greensboro, MD 21639

      26062 Holly Ln, Greensboro, MD 21639
  • 4 S 1st St, Denton, MD 21629
    4 S 1st St, Denton, MD 21629
    4 S 1st St, Denton, MD 21629
    /90

    $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
  • 5480 Bethlehem Rd, Preston, MD 21655
    5480 Bethlehem Rd, Preston, MD 21655
    5480 Bethlehem Rd, Preston, MD 21655
    /34

    $324,000 Sold Mar 03, 2025

    5480 Bethlehem Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1996

    Last Sold Summary

    • $263/SF
    • 9 Days On Market

    Current Estimated Value $351,263

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    5480 Bethlehem Rd, Preston, MD 21655
    • 202B Maple Ave, Federalsburg, MD 21632
      202B Maple Ave, Federalsburg, MD 21632
      202B Maple Ave, Federalsburg, MD 21632
      /23

      Est $171,002 Not Listed For Sale

      • Studio
      • 1,640 Sq Ft

      202B Maple Ave, Federalsburg, MD 21632

      202B Maple Ave, Federalsburg, MD 21632
  • 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

    Glory Bee Costa Keller Williams Select Realtors of Easton

    27279 Jenny Hye Ln, Marydel, MD 21649
  • 123 Park Ave, Greensboro, MD 21639

    $274,990 Sold Dec 16, 2025

    • 1,182 Sq Ft
    • $233/SF
    • 3 Beds
    • 2 Baths
    • Built 2025

    123 Park Ave, Greensboro, MD 21639

    Explore 123 Parkland Road, a new home under-construction in the quaint Kinnamon Meadows community of Greensboro, MD. The Curtis is a 1,182 square foot, cottage-style ranch home with three bedrooms and two bathrooms. As you enter the home through the front porch, this thoughtfully designed home has a grand open concept living area that leads into the spacious kitchen. To the right, a long, main

    D.R. Horton

    123 Park Ave, Greensboro, MD 21639
    • 201 Church St, Greensboro, MD 21639
      201 Church St, Greensboro, MD 21639
      201 Church St, Greensboro, MD 21639
      /52

      Est $382,033 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,559 Sq Ft

      201 Church St, Greensboro, MD 21639

      201 Church St, Greensboro, MD 21639
  • 21245 Tanyard Rd, Preston, MD 21655
    21245 Tanyard Rd, Preston, MD 21655
    21245 Tanyard Rd, Preston, MD 21655
    /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
  • 11921 Greensboro Rd, Greensboro, MD 21639
    11921 Greensboro Rd, Greensboro, MD 21639
    11921 Greensboro Rd, Greensboro, MD 21639
    /30

    $275,000 Sold Feb 18, 2025

    11921 Greensboro Rd, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1965

    Last Sold Summary

    • $205/SF
    • 39 Days On Market

    Current Estimated Value $299,177

    Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

    11921 Greensboro Rd, Greensboro, MD 21639
    • 1513 Cattail Commons Way, Denton, MD 21629
      1513 Cattail Commons Way, Denton, MD 21629
      1513 Cattail Commons Way, Denton, MD 21629
      /40

      Est $415,623 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,424 Sq Ft

      1513 Cattail Commons Way, Denton, MD 21629

      1513 Cattail Commons Way, Denton, MD 21629
  • 28035 Possum Hill Rd, Federalsburg, MD 21632
    28035 Possum Hill Rd, Federalsburg, MD 21632
    28035 Possum Hill Rd, Federalsburg, MD 21632
    /25

    $125,000

    • 2,168 Sq Ft

    28035 Possum Hill Rd, Federalsburg, MD 21632

    Prime Half-Acre Lot Near Smithville Lake – Cleared, with Well and Oversized Garage BayThis unique 0.48-acre property on Possum Hill Rd is ideally situated less than a mile west of the Maryland-Delaware state line, offering a rare combination of open space, infrastructure, and development potential.Property Highlights:Cleared Lot with Existing Well – The land has already been cleared

    Sam Benkirane Proplocate Realty, LLC

    28035 Possum Hill Rd, Federalsburg, MD 21632
  • 11255 Maplewood Dr, Ridgely, MD 21660
    11255 Maplewood Dr, Ridgely, MD 21660
    11255 Maplewood Dr, Ridgely, MD 21660
    /19

    $440,000 Sold Mar 11, 2025

    11255 Maplewood Dr, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,712 Sq Ft
    • Built 2020

    Last Sold Summary

    • $257/SF

    Current Estimated Value $467,904

    Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

    11255 Maplewood Dr, Ridgely, MD 21660
    • 10903 Collinswood Dr, Denton, MD 21629
      10903 Collinswood Dr, Denton, MD 21629
      10903 Collinswood Dr, Denton, MD 21629
      /37

      Est $874,665 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 4,404 Sq Ft

      10903 Collinswood Dr, Denton, MD 21629

      10903 Collinswood Dr, Denton, MD 21629
  • 106 Lednum Ave, Preston, MD 21655
    106 Lednum Ave, Preston, MD 21655
    106 Lednum Ave, Preston, MD 21655
    /17

    $380,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft

    106 Lednum Ave, Preston, MD 21655

    New construction in Preston, MD offering 3 bedrooms and 2 full baths across 1,400 square feet. This home features an open layout with vaulted ceilings, LVP flooring in the main living areas, and carpeted bedrooms. The kitchen is equipped with stainless steel appliances and granite countertops. The primary suite includes a stand-up shower, while the guest bath offers a tub/shower combo. An

    Eric Haro The Parker Group

    106 Lednum Ave, Preston, MD 21655
  • 306 Railroad Ave, Goldsboro, MD 21636
    306 Railroad Ave, Goldsboro, MD 21636
    306 Railroad Ave, Goldsboro, MD 21636
    /29

    $220,000 Sold Aug 07, 2025

    306 Railroad Ave, Goldsboro, MD 21636

    • 3 Beds
    • 1 Bath
    • 1,568 Sq Ft
    • Built 1900

    Last Sold Summary

    • $140/SF
    • 10 Days On Market

    Current Estimated Value $222,618

    Last Listing Agent Brett Schrader Taylor Properties

    306 Railroad Ave, Goldsboro, MD 21636
    • 508 N 6th St, Denton, MD 21629
      508 N 6th St, Denton, MD 21629
      508 N 6th St, Denton, MD 21629
      /15

      Est $260,721 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,192 Sq Ft

      508 N 6th St, Denton, MD 21629

      508 N 6th St, Denton, MD 21629
  • 0 Burnt Mill Rd Unit MDCM2006056, Ridgely, MD 21660
    0 Burnt Mill Rd Unit MDCM2006056, Ridgely, MD 21660
    0 Burnt Mill Rd Unit MDCM2006056, Ridgely, MD 21660
    /5

    $140,000

    • Land
    • 3.75 Acres
    • $37,333 per Acre

    0 Burnt Mill Rd Unit MDCM2006056, Ridgely, MD 21660

    Discover the ideal blend of tranquil nature and prime location! 3.75 acres with mature trees, offering unparalleled privacy and peaceful country living in one of the area's most scenic subdivisions -- all just minutes away from Ridgely and Denton, and less than 1 mile from North Caroline High School. Build your dream home on this beautiful level building lot, providing an even terrain throughout

    Stephan Strothe Washington Fine Properties, LLC

    0 Burnt Mill Rd Unit MDCM2006056, Ridgely, MD 21660
  • 202 Maryland Ave, Ridgely, MD 21660
    202 Maryland Ave, Ridgely, MD 21660
    202 Maryland Ave, Ridgely, MD 21660
    /18

    $300,000 Sold Nov 20, 2025

    202 Maryland Ave, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2000

    Last Sold Summary

    • $223/SF
    • 123 Days On Market

    Last Listing Agent Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    202 Maryland Ave, Ridgely, MD 21660
    • 1140 Canvasback Ln, Denton, MD 21629
      1140 Canvasback Ln, Denton, MD 21629
      1140 Canvasback Ln, Denton, MD 21629
      /39

      Est $418,524 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,602 Sq Ft

      1140 Canvasback Ln, Denton, MD 21629

      1140 Canvasback Ln, Denton, MD 21629

Showing Results 321 - 360, Page 9 of 18

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