15,698

Caroline County, MD Homes

Section Image
    • /18

      Est $519,006 Not Listed For Sale

      4191 Harmony Rd, Preston, MD 21655

      • 3 Beds
      • 2.5 Baths
      • 2,196 Sq Ft
      • Built 2007
      4191 Harmony Rd, Preston, MD 21655

      Last Sold Summary

      • 15% Above List Price
      • $205/SF
      • 10 Days On Market

      Last Sold Price $450,000

      Last Listing Agent Chuck Mangold Benson & Mangold, LLC

  • /17

    $195,000 Pending

    • 6 Beds
    • 1 Bath
    • 2,148 Sq Ft

    207 W Sunset Ave, Greensboro, MD 21639

    Welcome to 207 W Sunset Avenue, a well-located property in the heart of Greensboro, Maryland. Situated on a quiet residential street, this home offers convenient access to local shops, dining, schools, and parks, while maintaining the charm of a small-town setting. The property presents a solid opportunity for a primary residence, investment, or renovation project. With its established

    Holly Anderson Long & Foster Real Estate, Inc.

    207 W Sunset Ave, Greensboro, MD 21639
  • /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
    • /13

      Est $320,891 Not Listed For Sale

      1306 Chesapeake Dr, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 1,654 Sq Ft
      • Built 2004
      1306 Chesapeake Dr, Denton, MD 21629

      Last Sold Summary

      • 7% Above List Price
      • $181/SF
      • 14 Days On Market

      Last Sold Price $299,900

      Last Listing Agent Whitney Elliott Coldwell Banker Realty

  • /11

    $3,700,000

    8019 Patten Rd, Denton, MD 21629

    Poultry farm features a total of 60.57 acres (40 acres tillable, 8.5 acres wooded, 1.5-acre retention pond) and a 40x72 shop that has garage parking and a separate space that could be finished for permanent living. Located approx. 5 miles from the DE line. Expired site evaluation-no septic on property.

    Tambra Reagan CALLAWAY FARNELL AND MOORE

    8019 Patten Rd, Denton, MD 21629
  • /41

    $325,000 Sold Feb 27, 2026

    406 Wood Duck Dr, Greensboro, MD 21639

    • 3 Beds
    • 2.5 Baths
    • 1,364 Sq Ft
    • Built 2003

    Last Sold Summary

    • $238/SF
    • 114 Days On Market

    Current Estimated Value $319,486

    Last Listing Agent Brittany Gough RE/MAX One

    406 Wood Duck Dr, Greensboro, MD 21639
    • /30

      Est $404,046 Not Listed For Sale

      1106 Daylily Ln, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 3,096 Sq Ft
      • Built 2007
      1106 Daylily Ln, Denton, MD 21629

      Last Sold Summary

      • 1% Above List Price
      • $129/SF
      • 61 Days On Market

      Last Sold Price $399,000

      Last Listing Agent Shirley Coulbourne Coldwell Banker Realty

  • /12

    $205,000 Pending

    • 1 Bed
    • 1 Bath
    • 720 Sq Ft

    302 W Railroad St, Ridgely, MD 21660

    Cute little one bedroom bungalow in Ridgely. Extensively remodeled over the past year. New windows, flooring, Mini splits, kitchen cabinets, water heater. Comes with refrigerator, stackable washer/dryer, gas stove (Propane).Near grocery store, convince stores, nice park with track and tennis courts, Rails to Trail, hair salons, and auto repairs. Short distance to Adkins Arboretum and Tuckahoe

    Michael Shipley Benson & Mangold, LLC.

    302 W Railroad St, Ridgely, MD 21660
  • /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 $444,265

    Last Listing Agent Chuck Mangold Benson & Mangold, LLC

    22716 Havercamp Rd, Preston, MD 21655
    • /27

      Est $417,187 Not Listed For Sale

      5576 Harmony Woods Dr, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,700 Sq Ft
      • Built 2020
      5576 Harmony Woods Dr, Preston, MD 21655

      Last Sold Summary

      • 5% Above List Price
      • $235/SF
      • 10 Days On Market

      Last Sold Price $399,000

      Last Listing Agent Amy Betts Coldwell Banker Realty

  • /50

    $642,900

    • 4 Beds
    • 2.5 Baths
    • 2,920 Sq Ft

    24276 Asbury Dr, Denton, MD 21629

    Nestled in the shadows of the Choptank River is a meticulously maintained home in the water-privileged neighborhood of Asbury. Expansive lot sizes give you the privacy needed within a walkable neighborhood. Sit in your rocker with a cocktail while enjoying the dream turned into a reality of a wrap-around porch. A large rear screened-in porch to watch the local wildlife opens onto extensive

    Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    24276 Asbury Dr, Denton, MD 21629
  • /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 $273,034

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

    104 Sunset Blvd, Ridgely, MD 21660
    • /6

      Est $80,368 Not Listed For Sale

      27105 River Bridge Rd, Henderson, MD 21640

      • Built 1955
      27105 River Bridge Rd, Henderson, MD 21640

      Last Sold Summary

      • 34% Above List Price
      • $56/SF
      • 4 Days On Market

      Last Sold Price $60,000

      Last Listing Agent David Moore Real Broker, LLC

  • /71

    $1,099,999 Pending

    • 4 Beds
    • 2.5 Baths
    • 3,242 Sq Ft

    7904 Clark Rd, Denton, MD 21629

    This ±45-acre previously certified organic farm is located just south of Denton and offers a well-rounded combination of productive farmland, agricultural infrastructure, and residential living. The property includes approximately ±41 acres of tillable ground equipped with a subsurface irrigation system fed by six on-site wells, providing efficient and reliable water delivery for a wide range of

    Jesse Highling The Land Group

    7904 Clark Rd, Denton, MD 21629
  • /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
    • /32

      Est $396,028 Not Listed For Sale

      26062 Holly Ln, Greensboro, MD 21639

      • 3 Beds
      • 2 Baths
      • 1,798 Sq Ft
      • Built 2007
      26062 Holly Ln, Greensboro, MD 21639

      Last Sold Summary

      • 2% Above List Price
      • $217/SF
      • 89 Days On Market

      Last Sold Price $390,000

      Last Listing Agent Norma Coursey Benson & Mangold, LLC

  • /23

    $1,100,000 Open Sat 12:30PM - 1:30PM

    • 3 Beds
    • 2 Baths
    • 2,320 Sq Ft

    6401 Laurel Grove Rd, Denton, MD 21629

    Nestled on an expansive 52.08-acre estate, this stunning ranch-style farm offers a harmonious blend of luxury and tranquility, perfect for those seeking an exclusive lifestyle in a serene rural setting. The property boasts a traditional architectural design, complemented by aluminum siding that enhances its timeless appeal. Step inside to discover a thoughtfully designed interior that exudes

    Michelle Anderson Coldwell Banker Premier - Rehoboth

    6401 Laurel Grove Rd, Denton, MD 21629
  • /2

    $70,000 Sold Jan 09, 2026

    22415 Hillsboro Rd, Denton, MD 21629

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft
    • Built 1910

    Last Sold Summary

    • $61/SF
    • 17 Days On Market

    Current Estimated Value $122,866

    Last Listing Agent TAMMY GREEN Samson Properties

    22415 Hillsboro Rd, Denton, MD 21629
    • /23

      Est $163,060 Not Listed For Sale

      202B Maple Ave, Federalsburg, MD 21632

      • Studio
      • 1,640 Sq Ft
      • Built 1903
      202B Maple Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 63% Above List Price
      • $61/SF
      • 9 Days On Market

      Last Sold Price $100,000

      Last Listing Agent Kathleen Brenton Brenton Realty Group

  • /23

    $1,100,000 Open Sat 12:30PM - 1:30PM

    • 3 Beds
    • 2 Baths
    • 2,320 Sq Ft

    6401 Laurel Grove Rd, Denton, MD 21629

    Nestled on an expansive 52.08-acre estate, this stunning ranch-style farm offers a harmonious blend of luxury and tranquility, perfect for those seeking an exclusive lifestyle in a serene rural setting. The property boasts a traditional architectural design, complemented by aluminum siding that enhances its timeless appeal. Step inside to discover a thoughtfully designed interior that exudes

    Michelle Anderson Coldwell Banker Premier - Rehoboth

    6401 Laurel Grove Rd, Denton, MD 21629
  • 123 Park Ave, Greensboro, MD 21639

    $274,990 Sold Dec 16, 2025

    123 Park Ave, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $233/SF
    • 27 Days On Market

    Current Estimated Value $284,209

    D.R. Horton Kinnamon Meadows

    123 Park Ave, Greensboro, MD 21639
    • /52

      Est $371,065 Not Listed For Sale

      201 Church St, Greensboro, MD 21639

      • 4 Beds
      • 2 Baths
      • 2,559 Sq Ft
      • Built 1910
      201 Church St, Greensboro, MD 21639

      Last Sold Summary

      • 37% Above List Price
      • $106/SF
      • 59 Days On Market

      Last Sold Price $270,000

      Last Listing Agent Julie Stevenson Shore Living Real Estate

  • /2

    $32,500

    • Land
    • 0.69 Acre
    • $47,101 per Acre

    0 Douglas & Lincoln St Unit MDCM2006716, Ridgely, MD 21660

    Just next to the quaint town of Ridgely, this .69 acre lot also comes with a bonus lot highlighted in photos. Buy and hold as an investment or see if you can perc.

    Michael Rosendale Rosendale Realty

    0 Douglas & Lincoln St Unit MDCM2006716, Ridgely, MD 21660
  • /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 $215,363

    Last Listing Agent Brett Schrader Taylor Properties

    306 Railroad Ave, Goldsboro, MD 21636
    • /40

      Est $409,323 Not Listed For Sale

      1513 Cattail Commons Way, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,424 Sq Ft
      • Built 2006
      1513 Cattail Commons Way, Denton, MD 21629

      Last Sold Summary

      • 11% Above List Price
      • $153/SF
      • 24 Days On Market

      Last Sold Price $369,900

      Last Listing Agent Sean Monahan Cummings & Co Realtors

  • /38

    $479,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    11473 Holly Rd, Ridgely, MD 21660

    Welcome to modern country living with room to breathe. This nearly new rancher, only 6 months old, sits on 2.34 private acres with NO HOA, giving you the freedom to truly enjoy your property.Inside, the home features LVP flooring throughout, creating a seamless and durable living space. The stunning kitchen is the heart of the home with sleek cabinetry, gorgeous quartz countertops, and a

    Crystal Smith RE/MAX Executive

    11473 Holly Rd, Ridgely, MD 21660
  • /43

    $245,000 Sold Mar 18, 2026

    511 Bernard Ave, Greensboro, MD 21639

    • 3 Beds
    • 1 Bath
    • 1,385 Sq Ft
    • Built 1950

    Last Sold Summary

    • $177/SF
    • 118 Days On Market

    Current Estimated Value $247,302

    Last Listing Agent Karen Clark Clark & Co Realty, LLC

    511 Bernard Ave, Greensboro, MD 21639
    • /37

      Est $817,106 Not Listed For Sale

      10903 Collinswood Dr, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 4,404 Sq Ft
      • Built 2007
      10903 Collinswood Dr, Denton, MD 21629

      Last Sold Summary

      • 2% Above List Price
      • $183/SF
      • 4 Days On Market

      Last Sold Price $805,000

      Last Listing Agent Bruce Hechmer Long & Foster

  • /69

    $740,000

    • 5 Beds
    • 4 Baths
    • 5,286 Sq Ft

    24764 Pealiquor Rd, Denton, MD 21629

    Welcome to Timeless Elegance Meets Modern Comfort. Step inside this stunning Cape Cod residence and immediately feel at home. A gracious foyer framed by classic columns invites you into a luminous interior that effortlessly blends traditional charm with modern open‐concept living. To your right, a versatile flex room offers the perfect space for a home office, formal dining, or private study.

    Dustin Parker The Parker Group

    24764 Pealiquor Rd, Denton, MD 21629
  • /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

    Current Estimated Value $296,858

    Last Listing Agent Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    202 Maryland Ave, Ridgely, MD 21660
    • /39

      Est $397,011 Not Listed For Sale

      1140 Canvasback Ln, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,602 Sq Ft
      • Built 2007
      1140 Canvasback Ln, Denton, MD 21629

      Last Sold Summary

      • 6% Above List Price
      • $143/SF
      • 74 Days On Market

      Last Sold Price $373,000

      Last Listing Agent Mark Milligan RE/MAX

  • /10

    $184,900

    • 3 Beds
    • 1 Bath
    • 716 Sq Ft

    406 Lincoln St, Denton, MD 21629

    This adorable home is ready and waiting for you to move in and make it your own. The home was renovated just 2 years ago. Updated items include windows, HVAC, cabinets, flooring, carpet, plumbing, electric, and roof. Enjoy being close to local restaurants, shops, parks, schools, boat ramps, and MD/DE beaches. This property was most recently used as an income-producing rental property. Property is

    Lisa Secrist Chesapeake Real Estate Associates, LLC

    406 Lincoln St, Denton, MD 21629
  • /55

    $390,000 Sold Jun 20, 2025

    305 Morning Glory Dr, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,646 Sq Ft
    • Built 2021

    Last Sold Summary

    • $147/SF
    • 37 Days On Market

    Current Estimated Value $406,430

    Last Listing Agent Cornelia Fallon Coldwell Banker Waterman Realty

    305 Morning Glory Dr, Denton, MD 21629
    • /19

      Est $384,000 Not Listed For Sale

      1238 Painted Fern Rd, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,492 Sq Ft
      • Built 2006
      1238 Painted Fern Rd, Denton, MD 21629

      Last Sold Summary

      • 24% Above List Price
      • $124/SF
      • 12 Days On Market

      Last Sold Price $309,990

      Last Listing Agent George Hughes Coldwell Banker (NRT-Southeast-MidAtlantic)

  • /49

    $797,500 Under Contract

    • 3 Beds
    • 2 Baths
    • 2,342 Sq Ft

    12618 Knife Box Rd, Greensboro, MD 21639

    Custom home built in 2007, this home features a large eat in kitchen, a lovely screened porch over looking the park like property. Living room featuring a fireplace, and tray ceiling. to add another cozy feature. Hard wood flooring through out the living space gives that warm welcoming vibe. The property has the potential to be off the grid, the geothermal system is the basis., and a wood stove

    Kat Thompson Benson & Mangold, LLC.

    12618 Knife Box Rd, Greensboro, MD 21639
  • /64

    $565,000 Sold Oct 08, 2025

    6074 Newton Rd, Preston, MD 21655

    • 3 Beds
    • 2.5 Baths
    • 2,060 Sq Ft
    • Built 1993

    Last Sold Summary

    • $274/SF
    • 64 Days On Market

    Current Estimated Value $550,945

    Last Listing Agent James Bent Benson & Mangold, LLC

    6074 Newton Rd, Preston, MD 21655
    • /45

      Est $237,055 Not Listed For Sale

      1306 Blue Heron Dr, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 1,620 Sq Ft
      • Built 2004
      1306 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 4% Below List Price
      • $152/SF
      • 3 Days On Market

      Last Sold Price $247,000

      Last Listing Agent Lawrence Lessin Save 6, Incorporated

  • /4

    $24,500

    • 2 Beds
    • 1 Bath
    • 1,024 Sq Ft

    204 Academy Ave, Federalsburg, MD 21632

    Investor special! This property is being sold AS-IS and is priced for land value or a full renovation. The existing structure requires extensive repairs or complete tear-down—ideal for experienced builders, contractors, or savvy investors looking for a project. Buyer to verify zoning, permits, potential use. Buyer Broker/Agent and/or Buyer must do their own due diligence to verify if the existing

    Mike Dunn Keller Williams Realty Delmarva

    204 Academy Ave, Federalsburg, MD 21632
  • /18

    $250,000 Sold Oct 14, 2025

    508 W Sunset Ave, Greensboro, MD 21639

    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft
    • Built 1975

    Last Sold Summary

    • $223/SF
    • 8 Days On Market

    Current Estimated Value $245,957

    Last Listing Agent Erene Katris Coldwell Banker Realty

    508 W Sunset Ave, Greensboro, MD 21639
    • /54

      Est $326,881 Not Listed For Sale

      203 Wood Duck Dr, Greensboro, MD 21639

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 2003
      203 Wood Duck Dr, Greensboro, MD 21639

      Last Sold Summary

      • 1% Above List Price
      • $242/SF
      • 7 Days On Market

      Last Sold Price $325,000

      Last Listing Agent Christina Smith Brenton Realty Group

Showing Results 361 - 400, Page 10 of 18

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