15,626

Caroline County, MD Homes

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  • /30

    $249,900

    $25K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    205 N Academy St, Greensboro, MD 21639

    Welcome to this fully remodeled ranch, perfectly situated on a level lot on a quiet street. The showstopper kitchen features white shaker cabinets with dovetailed soft-close drawers, white quartz countertops, tile backsplash, and stainless steel appliances. Every inch of this home has been thoughtfully updated with new LVP flooring, plush carpet, fresh paint, and new lighting throughout. The

    Lee Wolff FSBO Broker

    205 N Academy St, Greensboro, MD 21639
  • /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 $254,625

    Last Listing Agent Erene Katris Coldwell Banker Realty

    508 W Sunset Ave, Greensboro, MD 21639
    • /8

      Est $488,201

      Not Listed For Sale

      23209 Gilpin Point Rd, Preston, MD 21655

      • 2 Beds
      • 1 Bath
      • 1,560 Sq Ft
      • Built 1965
      23209 Gilpin Point Rd, Preston, MD 21655

      Last Sold Summary

      • 127 Days On Market

      Last Listing Agent rachael harrison Coldwell Banker Realty

  • /28

    $399,000

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

    1 Sunrise Ave, Ridgely, MD 21660

    1 Sunrise Avenue is complete and ready for your private tour today! Just imagine starting your mornings in this thoughtfully crafted Lomaxx Custom Homes new build. Golden light spills across the nearby fields and settles gently indoors, where days begin with coffee on the back deck, birds gliding by, and daylight drifting through the windows, filling each room with a calm glow. Lomaxx Custom

    Crystal Smith RE/MAX Executive

    1 Sunrise Ave, Ridgely, MD 21660
  • /21

    $309,000

    Sold Nov 03, 2025

    27381 Greenwood Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,922 Sq Ft
    • Built 1900

    Last Sold Summary

    • $161/SF
    • 66 Days On Market

    Current Estimated Value $310,719

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

    27381 Greenwood Rd, Denton, MD 21629
    • /17

      Est $227,767

      Not Listed For Sale

      1115 Market St, Denton, MD 21629

      • 2 Beds
      • 1 Bath
      • 788 Sq Ft
      • Built 1950
      1115 Market St, Denton, MD 21629

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Marti McGinty Chesapeake Real Estate Associates, LLC

  • /37

    $299,000

    Under Contract
    • 3 Beds
    • 1 Bath
    • 1,222 Sq Ft

    7192 American Corner Rd, Denton, MD 21629

    Come make this updated and move in ready rancher your new home. Considerable improvements have been made over the last two years to include the following. This home has a new deep well, new septic system, new tankless propane water heater, new washer/dryer. new range and refrigerator, new roof, new siding, new hvac, renovated bathroom, new flooring, fresh paint, new privacy and chain link fencing

    Andrew Beaven Wright Real Estate

    7192 American Corner Rd, Denton, MD 21629
  • /20

    $280,000

    Sold Apr 17, 2026

    1303 Fairfield Ct, Denton, MD 21629

    • 2 Beds
    • 1 Bath
    • 1,426 Sq Ft
    • Built 2003

    Last Sold Summary

    • 3% Below List Price
    • $196/SF
    • 30 Days On Market

    Current Estimated Value $276,263

    Last Listing Agent Tricia Wilson Wilson Realty & Staging LLC

    1303 Fairfield Ct, Denton, MD 21629
    • /33

      Est $323,309

      Not Listed For Sale

      7881 Dyer Rd, Denton, MD 21629

      • 4 Beds
      • 2 Baths
      • 1,961 Sq Ft
      • Built 1972
      7881 Dyer Rd, Denton, MD 21629

      Last Sold Summary

      • 40 Days On Market

      Last Listing Agent Douglas Reyes Smart Realty, LLC

  • /4

    $155,000

    • 1 Bed
    • 1 Bath
    • 512 Sq Ft

    26355 Marydel Rd, Marydel, MD 21649

    House is of little to no value, existing well and septic. This house includes an additional parcel of 7 acres, tax id, 0601012428 for a total of 7.27 acres. Property being SOLD AS IS.

    George Thompson Long & Foster Real Estate, Inc.

    26355 Marydel Rd, Marydel, MD 21649
  • /33

    $185,000

    Sold May 13, 2026

    221 Denton Rd, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,078 Sq Ft
    • Built 1880

    Last Sold Summary

    • 3% Above List Price
    • $172/SF
    • 56 Days On Market

    Current Estimated Value $180,607

    Last Listing Agent Matthew Altizer ANR Realty, LLC

    221 Denton Rd, Federalsburg, MD 21632
    • /30

      Est $279,235

      Not Listed For Sale

      1612 Blue Heron Dr, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,244 Sq Ft
      • Built 2006
      1612 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Mary Wagner Cummings & Co. Realtors

  • /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
  • /99

    $420,000

    Sold Aug 29, 2025

    208 Bloomingdale Ave, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 3,734 Sq Ft
    • Built 1930

    Last Sold Summary

    • $112/SF
    • 16 Days On Market

    Current Estimated Value $432,604

    Last Listing Agent Blaine Williamson McClain-Williamson Realty, LLC

    208 Bloomingdale Ave, Federalsburg, MD 21632
    • /38

      Est $277,326

      Not Listed For Sale

      1606 Blue Heron Dr, Denton, MD 21629

      • 4 Beds
      • 3.5 Baths
      • 2,268 Sq Ft
      • Built 2006
      1606 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Joelle Dolch Cross Street Realtors LLC

  • /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
  • /19

    $325,000

    Sold Aug 08, 2025

    1206 Trice Meadows Cir, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,470 Sq Ft
    • Built 2018

    Last Sold Summary

    • $221/SF
    • 86 Days On Market

    Current Estimated Value $336,350

    Last Listing Agent Bonnie Johnson Keller Williams Realty

    1206 Trice Meadows Cir, Denton, MD 21629
    • /38

      Est $244,002

      Not Listed For Sale

      26875 Barclay Rd, Marydel, MD 21649

      • 3 Beds
      • 1 Bath
      • 1,404 Sq Ft
      • Built 1951
      26875 Barclay Rd, Marydel, MD 21649

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Erin Anderson Chesapeake Real Estate Associates, LLC

  • /50

    $609,000

    • 5 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. Beautiful Expansive lot size gives you the privacy needed within a walkable neighborhood. The flat level lot opens up future pool and other amenity possibilities. Sit in your rocker with a cocktail while enjoying the dream turned into a reality of a wrap-around porch. A

    Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    24276 Asbury Dr, Denton, MD 21629
  • /26

    $280,000

    Sold Aug 25, 2025

    104 S 8th St, Denton, MD 21629

    • 2 Beds
    • 1.5 Baths
    • 1,055 Sq Ft
    • Built 1973

    Last Sold Summary

    • $265/SF
    • 7 Days On Market

    Current Estimated Value $276,491

    Last Listing Agent Tony Letizia VRA Realty

    104 S 8th St, Denton, MD 21629
    • /73

      Est $670,746

      Not Listed For Sale

      20810 Frazier Point Ln, Preston, MD 21655

      • 3 Beds
      • 2.5 Baths
      • 2,226 Sq Ft
      • Built 1970
      20810 Frazier Point Ln, Preston, MD 21655

      Last Sold Summary

      • 229 Days On Market

      Last Listing Agent Barbara McCaffrey Redfin Corp

  • /20

    $345,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,510 Sq Ft

    114 Wothers Rd, Greensboro, MD 21639

    Completely renovated in 2017, this beautiful home sits on a spacious one-acre lot offering room to spread out and endless possibilities both inside and out. Step inside to a welcoming foyer where gleaming hardwood floors flow throughout the generous living and dining areas. The main level features elegant crown molding and chair railing, along with a stunning open-concept kitchen complete with a

    Anthony MacDonald Iron Valley Real Estate Ocean City

    114 Wothers Rd, Greensboro, MD 21639
  • /106

    $540,000

    Sold Sep 04, 2025

    8534 Briar Patch Dr, Denton, MD 21629

    • 4 Beds
    • 3 Baths
    • 3,039 Sq Ft
    • Built 1995

    Last Sold Summary

    • $178/SF
    • 68 Days On Market

    Current Estimated Value $550,959

    Last Listing Agent Alana Taylor Worthington Realty Group, LLC

    8534 Briar Patch Dr, Denton, MD 21629
    • /28

      Est $284,395

      Not Listed For Sale

      1614 Blue Heron Dr, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,244 Sq Ft
      • Built 2006
      1614 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Marcy Gaines CENTURY 21 New Millennium

  • /94

    $380,000

    • 3 Beds
    • 2 Baths
    • 1,904 Sq Ft

    28440 Bloomery Rd, Federalsburg, MD 21632

    If you've been searching for a property that offers acreage, privacy, and plenty of room to grow, this is the one you've been waiting for! Nestled on 3.80 wooded acres, this ranch-style home offers approximately 1,904 square feet of comfortable living space, featuring 3 bedrooms, 2 full baths, and two versatile bonus rooms that can easily serve as a home office, hobby room, playroom, guest space,

    Sean Steward Century 21 Home Team Realty

    28440 Bloomery Rd, Federalsburg, MD 21632
  • /65

    $450,000

    Sold Sep 12, 2025

    135 Walnut St, Ridgely, MD 21660

    • 4 Beds
    • 4 Baths
    • 3,408 Sq Ft
    • Built 2005

    Last Sold Summary

    • $132/SF
    • 4 Days On Market

    Current Estimated Value $455,432

    Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

    135 Walnut St, Ridgely, MD 21660
    • /31

      Est $230,567

      Not Listed For Sale

      3427 Holland Dr, Federalsburg, MD 21632

      • 3 Beds
      • 1 Bath
      • 1,091 Sq Ft
      • Built 1994
      3427 Holland Dr, Federalsburg, MD 21632

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Matthew Olson EXP Realty, LLC

  • /40

    $285,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,677 Sq Ft

    103 Williamson St, Preston, MD 21655

    Welcome home to this beautifully remodeled 3-bedroom, 2-bath home situated on nearly a half-acre lot in the charming town of Preston. This move-in ready property features beautiful hardwood floors, a spacious kitchen with abundant cabinetry, granite countertops, new appliances, and new carpet throughout. The inviting living room showcases gleaming hardwood floors and a cozy gas fireplace,

    Dawn Hubbard Keller Williams Select Realtors of Cambridge

    103 Williamson St, Preston, MD 21655
  • /48

    $471,500

    Sold Apr 30, 2026

    111 Riverview Ln, Greensboro, MD 21639

    • 4 Beds
    • 1.5 Baths
    • 2,000 Sq Ft
    • Built 1977

    Last Sold Summary

    • 5% Above List Price
    • $236/SF

    Current Estimated Value $467,974

    Last Listing Agent John Howard Long & Foster Real Estate, Inc.

    111 Riverview Ln, Greensboro, MD 21639
    • /13

      Est $273,544

      Not Listed For Sale

      25 Greenridge Ave, Ridgely, MD 21660

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft
      • Built 1993
      25 Greenridge Ave, Ridgely, MD 21660

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Marti McGinty Chesapeake Real Estate Associates, LLC

  • /20

    $850,000

    $250K PRICE DROP Under Contract
    • 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
  • /29

    $380,000

    Sold Nov 14, 2025

    24887 Holsinger Ln, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Built 2015

    Last Sold Summary

    • $264/SF
    • 120 Days On Market

    Current Estimated Value $380,713

    Last Listing Agent Laura Anthony Benson & Mangold, LLC

    24887 Holsinger Ln, Ridgely, MD 21660
    • /56

      Est $403,156

      Not Listed For Sale

      12710 Greensboro Rd, Greensboro, MD 21639

      • 3 Beds
      • 2.5 Baths
      • 1,472 Sq Ft
      • Built 1950
      12710 Greensboro Rd, Greensboro, MD 21639

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Scott Judy Coldwell Banker Waterman Realty

  • /20

    $205,000

    $5K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 812 Sq Ft

    310 Park Ave, Federalsburg, MD 21632

    This charming farmhouse-style home, built in 1904 has undergone a major renovation in 2026. With 812 square feet of thoughtfully designed living space, this delightful residence features two cozy bedrooms and one and a half bathrooms, making it an ideal retreat for those seeking comfort and style. Step inside to discover a beautifully updated interior adorned with luxury vinyl plank flooring,

    Cheryl Knotts Chesapeake Real Estate Associates, LLC

    310 Park Ave, Federalsburg, MD 21632
  • /11

    $245,000

    Sold Sep 09, 2025

    210 Denton Rd, Federalsburg, MD 21632

    • 4 Beds
    • 3 Baths
    • 1,190 Sq Ft
    • Built 1935

    Last Sold Summary

    • $206/SF
    • 127 Days On Market

    Current Estimated Value $189,627

    Last Listing Agent Kat Thompson Benson & Mangold, LLC.

    210 Denton Rd, Federalsburg, MD 21632
    • /41

      Est $282,122

      Not Listed For Sale

      1915 Blue Heron Dr, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,640 Sq Ft
      • Built 2006
      1915 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Pamela Ackermann-Doll RE/MAX Executive

  • /6

    $360,000

    $40K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,128 Sq Ft

    26784 Bilbrough Rd, Goldsboro, MD 21636

    Welcome to your private slice of Eastern Shore living in Goldsboro. Set on 4.7 secluded acres, this 2022-built home offers the space, comfort, and modern features today's market demands. With over 2,100 square feet, 4 bedrooms, and 2 full baths, the layout is open, bright, and designed for seamless everyday living. Step inside to a spacious floor plan that flows effortlessly from room to

    Sandra Bradley Keller Williams Select Realtors of Easton

    26784 Bilbrough Rd, Goldsboro, MD 21636
  • /34

    $332,000

    Sold Sep 05, 2025

    22329 Tanyard Rd, Preston, MD 21655

    • 3 Beds
    • 1 Bath
    • 1,058 Sq Ft
    • Built 1972

    Last Sold Summary

    • $314/SF
    • 29 Days On Market

    Current Estimated Value $333,615

    Last Listing Agent Laura Anderson Coldwell Banker Realty

    22329 Tanyard Rd, Preston, MD 21655
    • /15

      Est $328,013

      Not Listed For Sale

      8888 Harmony Rd, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,680 Sq Ft
      • Built 1910
      8888 Harmony Rd, Denton, MD 21629

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Preda Mendez-Lopez Realty One Group Performance, LLC

  • /19

    $850,000

    Under Contract
    • 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

Showing Results 401 - 440, Page 11 of 18

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