15,626

Caroline County, MD Homes

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  • /63

    $399,000

    $9K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft

    7392 Todds Wharf Rd, Preston, MD 21655

    This very comfortable rancher has ramps at rear of home for accessibility for those not able to walk up steps very well. Roomy kitchen and open floor plan allows large gatherings to enjoy the roominess. Large counter seats 4 comfortably. Dining area for full-size table and chairs. Working stone wood-burning fireplace is great for use to heat home all winter or just on-call use when you want the

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    7392 Todds Wharf Rd, Preston, MD 21655
  • /2

    $380,000

    Sold Jan 23, 2026

    0 River Rd Unit MDCM2005824, Ridgely, MD 21660

    • Land
    • 44.74 Acres
    • $8,494 per Acre

    Last Sold Summary

    • 17% Below List Price
    • 203 Days On Market

    Last Listing Agent Andrew Beaven Wright Real Estate

    0 River Rd Unit MDCM2005824, Ridgely, MD 21660
    • /27

      Est $363,317

      Not Listed For Sale

      1202 Trice Meadows Cir, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,540 Sq Ft
      • Built 2010
      1202 Trice Meadows Cir, Denton, MD 21629

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Karen Clark Clark & Co Realty, LLC

  • /49

    $315,000

    Open Sat 11AM - 1PM
    • 4 Beds
    • 2 Baths
    • 2,774 Sq Ft

    111 Maple Ave, Greensboro, MD 21639

    Step into the timeless charm of this beautifully maintained circa-1880 home, where historic elegance meets thoughtful modern updates. Offering over 2,774 square feet of living space, this exceptional residence features 4 spacious bedrooms, 2 full bathrooms, and an abundance of original architectural character that has been lovingly preserved while incorporating today's modern conveniences. From

    Barbara McCaffrey Redfin Corp

    111 Maple Ave, Greensboro, MD 21639
  • /22

    $500,000

    Sold May 28, 2026

    8664 Mitchell Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 2,100 Sq Ft
    • Built 2003

    Last Sold Summary

    • 5% Below List Price
    • $238/SF
    • 43 Days On Market

    Current Estimated Value $502,222

    Last Listing Agent Cheryl Knotts Chesapeake Real Estate Associates, LLC

    8664 Mitchell Rd, Denton, MD 21629
    • /39

      Est $341,663

      Not Listed For Sale

      531 Oldtown Rd, Goldsboro, MD 21636

      • 3 Beds
      • 2 Baths
      • Built 2025
      531 Oldtown Rd, Goldsboro, MD 21636

      Last Sold Summary

      • 156 Days On Market

      Last Listing Agent Dawn Williams Berkshire Hathaway Homeservice Homesale Realty

  • /43

    $424,900

    Under Contract
    • 3 Beds
    • 1.5 Baths
    • 1,800 Sq Ft

    509 S 2nd St, Denton, MD 21629

    Welcome to one of Denton’s most enchanting hidden retreats — a beautifully restored and thoughtfully updated 1941 Cape Cod tucked among towering trees, lush gardens, and comfortable living spaces in the heart of town.Lovingly renovated while preserving its original charm and architectural character, the main residence offers timeless warmth and understated elegance throughout. Rich hardwood

    Judith Germain Benson & Mangold, LLC

    509 S 2nd St, Denton, MD 21629
  • /24

    $290,000

    Sold Jan 15, 2026

    26056 Fox Grape Rd, Greensboro, MD 21639

    • 3 Beds
    • 1.5 Baths
    • 1,215 Sq Ft
    • Built 1981

    Last Sold Summary

    • $239/SF
    • 2 Days On Market

    Current Estimated Value $293,517

    Last Listing Agent Amanda Morgan Brenton Realty Group

    26056 Fox Grape Rd, Greensboro, MD 21639
    • /10

      Est $405,963

      Not Listed For Sale

      1101 Trice Meadows Cir, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,300 Sq Ft
      • Built 2023
      1101 Trice Meadows Cir, Denton, MD 21629

      Last Sold Summary

      • 95 Days On Market

      Last Listing Agent Michelle DiDonato Island Realty, LLC

  • /41

    $579,900

    Open Sat 11AM - 1PM $15K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,643 Sq Ft

    24766 Tribbett Cir, Ridgely, MD 21660

    Welcome to this meticulously crafted 2023 contemporary farmhouse, perfectly positioned on a spacious .85-acre lot in the established community of Ashworth. Offering 3,168 square feet, 4 bedrooms, and 2.5 baths, this beautifully designed home blends timeless farmhouse charm with modern finishes and thoughtful upgrades throughout. The striking exterior showcases classic white siding, bold black

    Barbara McCaffrey Redfin Corp

    24766 Tribbett Cir, Ridgely, MD 21660
  • /28

    $220,000

    Sold Mar 31, 2026

    229 Oldtown Rd, Goldsboro, MD 21636

    • 3 Beds
    • 2 Baths
    • 1,368 Sq Ft
    • Built 1900

    Last Sold Summary

    • $161/SF
    • 124 Days On Market

    Current Estimated Value $219,377

    Last Listing Agent Brett Schrader Taylor Properties

    229 Oldtown Rd, Goldsboro, MD 21636
    • /21

      Est $232,379

      Not Listed For Sale

      613 Denton Rd, Federalsburg, MD 21632

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft
      • Built 1930
      613 Denton Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Austin Whitehead Whitehead Real Estate Exec.

  • /27

    $369,900

    $5K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 2,268 Sq Ft

    803 Market St, Denton, MD 21629

    This inviting Victorian offers 4 bedrooms and 1.5 baths, that’s perfect for unwinding at the end of the day. Inside, natural light fills the main level, highlighting warm hardwood floors and comfortable living spaces. The living and dining areas connect seamlessly, creating an easy flow for everyday living. The kitchen features ample cabinet and counter space, stainless steel appliances, and a

    Steven Parsons Coldwell Banker Realty

    803 Market St, Denton, MD 21629
  • /34

    $195,000

    Sold Jun 05, 2026

    27320 Chipmans Ln, Federalsburg, MD 21632

    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft
    • Built 1965

    Last Sold Summary

    • 14% Below List Price
    • $174/SF
    • 37 Days On Market

    Current Estimated Value $198,196

    Last Listing Agent Justin Pokrywka Taylor Properties

    27320 Chipmans Ln, Federalsburg, MD 21632
    • /18

      Not Listed For Sale

      8 N 2nd St, Denton, MD 21629

      • 3 Beds
      • 5 Baths
      • 3,482 Sq Ft
      • Built 1890
      8 N 2nd St, Denton, MD 21629

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Linda Moore Long & Foster Real Estate, Inc.

  • /66

    $374,990

    Under Contract
    • 4 Beds
    • 2 Baths
    • 1,880 Sq Ft

    23116 Gilpin Point Rd, Preston, MD 21655

    Welcome to 23116 Gilpin Point Road in Preston, an updated Eastern Shore rancher offering the perfect blend of one floor living, privacy, history, and water oriented lifestyle. Beautifully situated on a spacious setting in the historic Gilpin Point area, this inviting home provides a peaceful country backdrop while still offering convenient access to nearby towns, commuter routes, and the gorgeous

    Angela Demattia Berkshire Hathaway HomeServices PenFed Realty

    23116 Gilpin Point Rd, Preston, MD 21655
  • /5

    $132,000

    Sold Sep 25, 2025

    28471 Kinder Rd, Federalsburg, MD 21632

    • 3 Beds
    • 1 Bath
    • 640 Sq Ft
    • Built 1963

    Last Sold Summary

    • $206/SF
    • 71 Days On Market

    Current Estimated Value $145,368

    Last Listing Agent Gillian Walsh Keller Williams Realty

    28471 Kinder Rd, Federalsburg, MD 21632
    • /26

      Est $130,083

      Not Listed For Sale

      13416 Greensboro Rd, Greensboro, MD 21639

      • Built 1971
      13416 Greensboro Rd, Greensboro, MD 21639

      Last Sold Summary

      • 71 Days On Market

      Last Listing Agent Erin Anderson Chesapeake Real Estate Associates, LLC

  • /48

    $374,900

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

    8548 Dogwood Blossom Ln, Denton, MD 21629

    Nestled along a private road in a peaceful, tucked-away setting, this well-maintained Colonial offers the perfect blend of privacy, space, and convenience. Situated on more than 1.2 acres, the property backs to mature woods, providing beautiful wooded views and a serene backdrop to everyday living. The home needs only minor cosmetic updates, making it an excellent opportunity to add your own

    Barbara McCaffrey Redfin Corp

    8548 Dogwood Blossom Ln, Denton, MD 21629
  • /25

    $230,000

    Sold Jul 10, 2026

    28241 Hickman Cannery Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,436 Sq Ft
    • Built 1885

    Last Sold Summary

    • 18% Below List Price
    • $160/SF
    • 128 Days On Market

    Current Estimated Value $225,482

    Last Listing Agent Billy Mister Keller Williams Realty

    28241 Hickman Cannery Rd, Denton, MD 21629
    • /16

      Est $173,476

      Not Listed For Sale

      4845 Houston Branch Rd, Federalsburg, MD 21632

      4845 Houston Branch Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 91 Days On Market

      Last Listing Agent Pamela Price Berkshire Hathaway HomeServices PenFed Realty

  • /28

    $249,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,346 Sq Ft

    222 S 3rd St, Denton, MD 21629

    Discover the timeless appeal of this classic Cape Cod, ideally situated just moments from the heartof historic Denton. Lovingly maintained over the years, this three-bedroom, two-bath home offersenduring character, thoughtful updates, and an exceptional backyard retreat rarely found at thisprice point.The inviting floor plan is filled with natural light and includes comfortable

    Judith Germain Benson & Mangold, LLC

    222 S 3rd St, Denton, MD 21629
  • /37

    $238,000

    Sold Oct 07, 2025

    6238 Bethlehem Rd, Preston, MD 21655

    • 2 Beds
    • 1 Bath
    • 1,234 Sq Ft
    • Built 1875

    Last Sold Summary

    • $193/SF
    • 34 Days On Market

    Last Listing Agent Amy Betts Coldwell Banker Realty

    6238 Bethlehem Rd, Preston, MD 21655
    • /29

      Est $371,094

      Not Listed For Sale

      21994 Main St, Hillsboro, MD 21641

      • 3 Beds
      • 3 Baths
      • 4,000 Sq Ft
      • Built 1800
      21994 Main St, Hillsboro, MD 21641

      Last Sold Summary

      • 139 Days On Market

      Last Listing Agent Gina Gargeu Century 21 Downtown

  • /50

    $410,990

    $8K PRICE DROP Under Contract
    • 5 Beds
    • 2.5 Baths
    • 2,382 Sq Ft

    225 S 2nd St, Denton, MD 21629

    Welcome to one of Denton's most charming historic homes, where timeless Victorian architecture, thoughtful updates, and small-town living come together beautifully. Situated on a picturesque corner lot in Denton's historic district, this lovingly maintained five-bedroom home offers more than 2,300 square feet of character-filled living space, abundant natural light, original architectural

    Barbara McCaffrey Redfin Corp

    225 S 2nd St, Denton, MD 21629
  • /2

    $355,000

    Sold Jun 05, 2026

    221 Apple Ln, Preston, MD 21655

    • 4 Beds
    • 2 Baths
    • 1,700 Sq Ft
    • Built 1996

    Last Sold Summary

    • 1% Above List Price
    • $209/SF
    • 7 Days On Market

    Current Estimated Value $351,046

    Last Listing Agent Alex Archer Real Broker, LLC - Annapolis

    221 Apple Ln, Preston, MD 21655
  • /28

    $169,000

    • Land
    • 13.8 Acres
    • $12,246 per Acre

    000 Burnt Mill Rd, Ridgely, MD 21660

    This private 13.80 acre hunting tract offers an outstanding opportunity to own a well-managed and affordable recreational property on Maryland's Eastern Shore. Accessed by a deeded right-of-way, the property provides the privacy and seclusion serious hunters appreciate while remaining conveniently located for quick trips to the woods. The tract is comprised of mature hardwood timber and is

    Mike Arajakis Whitetail Properties Real Estate

    000 Burnt Mill Rd, Ridgely, MD 21660
  • /44

    $355,000

    Sold Aug 29, 2025

    3590 Choptank Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,476 Sq Ft
    • Built 1994

    Last Sold Summary

    • $241/SF
    • 32 Days On Market

    Current Estimated Value $356,268

    Last Listing Agent Dawn O'Day Samson Properties

    3590 Choptank Rd, Preston, MD 21655
    • /5

      Est $83,667

      Not Listed For Sale

      328 E Central Ave, Federalsburg, MD 21632

      328 E Central Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Heather Brummell Keller Williams Realty

  • /73

    $790,000

    $49K PRICE DROP
    • Land
    • 87 Acres
    • $9,080 per Acre

    000 Knife Box Rd, Greensboro, MD 21639

    PRICE IMPROVEMENT!!Located just outside Greensboro in Caroline County, Maryland, this exceptional 87 acre property offers a rare combination of income-producing farmland, diverse wildlife habitat, scenic natural features, and a highly developed hunting setup. The property consists of approximately 50 acres of mature woodland and 37 acres of productive tillable acreage, creating an ideal blend of

    Mike Arajakis Whitetail Properties Real Estate

    000 Knife Box Rd, Greensboro, MD 21639
  • /2

    $100,000

    Sold Nov 21, 2025

    13243 Greensboro Rd, Greensboro, MD 21639

    • 2 Beds
    • 2 Baths
    • 1,092 Sq Ft
    • Built 1910

    Last Sold Summary

    • $92/SF
    • 5 Days On Market

    Current Estimated Value $149,165

    Last Listing Agent Kat Thompson Benson & Mangold, LLC.

    13243 Greensboro Rd, Greensboro, MD 21639
    • /3

      Not Listed For Sale

      0 River Rd, Greensboro, MD 21639

      0 River Rd, Greensboro, MD 21639

      Last Sold Summary

      • 47 Days On Market

      Last Listing Agent Linda Moore Long & Foster Real Estate, Inc.

  • /30

    $52,000

    • Land
    • 5.2 Acres
    • $10,000 per Acre

    American Corner Rd, Denton, MD 21629

    5.20 Acres of Wooded Land for Hunting and Recreation on Paved Road in Caroline County, MdCash Price: $52,000Reservation Fee: $900 non-refundable reservation fee secures this property. Reservation fee will be counted toward purchase price or down payment.With your Purchase You Get:1. A Deed in Your Own Name2. 4. NO Closing Fees if you Close Directly In-House with

    Elegment Land Elegment.com

    American Corner Rd, Denton, MD 21629
  • /21

    $629,900

    Sold Jan 12, 2026

    26067 Goldsboro Rd, Goldsboro, MD 21636

    • 3 Beds
    • 2.5 Baths
    • 2,080 Sq Ft
    • Built 2024

    Last Sold Summary

    • $303/SF
    • 7 Days On Market

    Current Estimated Value $618,524

    Last Listing Agent Scott Judy Coldwell Banker Waterman Realty

    26067 Goldsboro Rd, Goldsboro, MD 21636
    • /5

      Est $49,303

      Not Listed For Sale

      26302 Sennett Rd, Denton, MD 21629

      26302 Sennett Rd, Denton, MD 21629

      Last Sold Summary

      • 233 Days On Market

      Last Listing Agent Michelle Anderson Coldwell Banker Premier - Seaford

  • /15

    $118,000

    Under Contract
    • 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
  • /26

    $330,000

    Sold Jul 17, 2026

    25389 Kent St, Greensboro, MD 21639

    • 3 Beds
    • 1.5 Baths
    • 1,152 Sq Ft
    • Built 1993

    Last Sold Summary

    • 6% Above List Price
    • $286/SF
    • 1 Day On Market

    Current Estimated Value $313,813

    Last Listing Agent Heather Brummell Keller Williams Realty

    25389 Kent St, Greensboro, MD 21639
    • /24

      Est $352,244

      Not Listed For Sale

      5540 American Corner Rd, Federalsburg, MD 21632

      • 3 Beds
      • 2 Baths
      • 1,200 Sq Ft
      • Built 2025
      5540 American Corner Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent David Moore Real Broker, LLC

  • /22

    $467,900

    • 3 Beds
    • 4 Baths
    • 2,713 Sq Ft

    202 N Central Ave, Ridgely, MD 21660

    Charming Victorian home in the heart of Ridgely, ideally situated on a picturesque, tree-shaded corner lot. This timeless property offers classic character, curb appeal, and a prime location close to local amenities. An expansive wraparound front porch sets the stage for this beautiful home, featuring a gracious entryway, stunning columned foyer, and gleaming hardwood floors that enhance its

    Marcia Rostien Long & Foster Real Estate, Inc.

    202 N Central Ave, Ridgely, MD 21660

Showing Results 41 - 80, Page 2 of 18

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