15,577

Caroline County, MD Homes

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  • /63

    $1,500,000

    Under Contract
    • 3 Beds
    • 3.5 Baths
    • 3,958 Sq Ft

    7347 Harmony Rd, Preston, MD 21655

    Income-producing poultry farm situated on approximately 38.17 acres in desirable Caroline County, featuring four state-of-the-art “Tier 3” tunnel poultry houses with a combined capacity of approximately 110,000 broiler chickens. Built in 1993, the four 40’ x 500’ houses are equipped with Rotem Platinum+ controllers, Shore Time computerized controls, alarm systems, recirculation cooling pads, 6”

    Agent Photo

    Damon Brockenberry

    Keller Williams Preferred Properties

    7347 Harmony Rd, Preston, MD 21655
  • /13

    $2,150 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft
    • Townhouse for Rent

    104 Riverwalk Terrace, Federalsburg, MD 21632

    Recently built in 2024, this 3-bedroom, 2.5-bath townhome offers approximately 1,440 sq. ft. of comfortable, low-maintenance living. The main level features LVP flooring and an open layout with a spacious family room flowing into the eat-in kitchen, complete with breakfast bar seating and room for a dining table. A sliding glass door leads to the flat backyard, and a powder room completes the

    Jennifer Norfolk Coldwell Banker Waterman Realty

    104 Riverwalk Terrace, Federalsburg, MD 21632
  • /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
    • /30

      Est $315,877

      Not Listed For Sale

      319 Mallard Dr, Greensboro, MD 21639

      • 3 Beds
      • 2 Baths
      • 1,468 Sq Ft
      • Built 2023
      319 Mallard Dr, Greensboro, MD 21639

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Juliet Wells Coldwell Banker Chesapeake Real Estate Company

  • /37

    $319,000

    $6K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,232 Sq Ft

    2792 Meadowbrook Rd, Federalsburg, MD 21632

    Space, flexibility, and outdoor living come together at 2792 Meadowbrook Road! This spacious 5-bedroom, 2.5-bath split-level home sits on a beautiful .46-acre lot.The upper level features three bedrooms, including a primary bedroom with its own private bath. The living room offers an open feel and an opportunity to create an even more unique space with the potential for an upper balcony. The

    Agent Photo

    Kate Lewis

    Keller Williams Realty

    2792 Meadowbrook Rd, Federalsburg, MD 21632
  • /22

    $2,000 Per Month

    • 4 Beds
    • 2 Baths
    • 2,688 Sq Ft
    • House for Rent

    22721 Marsh Creek Rd, Preston, MD 21655

    VERY NICE 4 BEDROOM 2 BATH COUNTRY HOME NEAR PRESTON. A FOUR SQUARE HOUSE WITH BUILT-IN CORNER CABINETS, SOME KNOTTY PINE WALLS AND SHELVING, WOOD FLOORS AND A FULL WIDTH FRONT PORCH. QUIET AND SECLUDED WITH LARGE SHADE TREES AND FARM FIELDS ALL AROUND FOR A BEAUTIFUL, COMFORTING VIEW. Back on rental market, previous applicants had to withdraw.

    Ed Quidas Long & Foster Real Estate, Inc.

    22721 Marsh Creek Rd, Preston, MD 21655
  • /22

    $329,500

    Sold Aug 24, 2026

    2691 Lorraine Ave, Federalsburg, MD 21632

    • 4 Beds
    • 2 Baths
    • 1,880 Sq Ft
    • Built 1987

    Last Sold Summary

    • 4% Below List Price
    • $175/SF
    • 32 Days On Market

    Current Estimated Value $349,661

    Last Listing Agent Norman Domingo XRealty.NET LLC

    2691 Lorraine Ave, Federalsburg, MD 21632
    • /23

      Est $298,736

      Not Listed For Sale

      105 Elmor Ct, Greensboro, MD 21639

      • 3 Beds
      • 2 Baths
      • 1,192 Sq Ft
      • Built 2013
      105 Elmor Ct, Greensboro, MD 21639

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent BJ Kilby Eastern Shore Real Estate, LLC

  • /3

    $55,000

    • Land
    • 4 Acres
    • $13,750 per Acre

    0 Houston Branch Rd Unit MDCM2007816, Federalsburg, MD 21632

    Secluded 4 Acre lot bordering the Idylwild Nature Preserve offering excellent hunting, biking, hiking and fishing. According to the county there is a well on site. Zoned R1. Property recently acquired through tax sale foreclosure. Note that the lot is only accessible at the end of Willin Ln off of Houston Branch Rd. Do NOT go to the property without prior authorization. Please call listing agent

    Agent Photo

    Joe Howerton

    Taylor Properties

    0 Houston Branch Rd Unit MDCM2007816, Federalsburg, MD 21632
  • /23

    $1,395 Per Month

    • 1 Bed
    • 1 Bath
    • House for Rent

    119 Davis Ln, Federalsburg, MD 21632

    Shane Snoots MD & DE Group Property Management

    119 Davis Ln, Federalsburg, MD 21632
  • /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
    • /66

      Est $335,951

      Not Listed For Sale

      25970 Three Bridges Rd, Federalsburg, MD 21632

      • 4 Beds
      • 2 Baths
      • 1,844 Sq Ft
      • Built 1996
      25970 Three Bridges Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 71 Days On Market

      Last Listing Agent John Tarpley Schwartz Realty, Inc.

  • /41

    $449,000

    • 3 Beds
    • 2 Baths
    • 1,392 Sq Ft

    11509 Reed Cir, Ridgely, MD 21660

    Welcome to 11509 Reed Cir, a charming 3-bedroom, 2-bathroom rancher nestled on 1.10 acres in Ridgely, Maryland. Set against a peaceful, tree-lined backdrop, this home offers comfortable one-level living with plenty of space to enjoy both indoors and out.A covered front porch welcomes you inside, where the inviting living room makes a statement with a floor-to-ceiling brick propane

    Samantha Jackson Keller Williams Realty

    11509 Reed 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
    • /19

      Est $222,373

      Not Listed For Sale

      206 Maple Ave, Ridgely, MD 21660

      • 2 Beds
      • 1.5 Baths
      • 1,248 Sq Ft
      • Built 1890
      206 Maple Ave, Ridgely, MD 21660

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Karen Clark Clark & Co Realty, LLC

  • /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
    • /5

      Est $508,673

      Not Listed For Sale

      24776 Tribbett Cir, Ridgely, MD 21660

      • Built 2025
      24776 Tribbett Cir, Ridgely, MD 21660

      Last Sold Summary

      • 261 Days On Market

      Last Listing Agent Stephan Strothe Washington Fine Properties, LLC

  • /66

    $374,990

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

    23116 Gilpin Point Rd, Preston, MD 21655

    BACK ACTIVE and offering another opportunity to make this special Eastern Shore property your own!Welcome to 23116 Gilpin Point Road in Preston, an updated Eastern Shore rancher offering the perfect blend of one-floor living, privacy, history, and a water-oriented lifestyle. Beautifully situated on a spacious setting in the historic Gilpin Point area, this inviting home provides a

    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
    • /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

    • 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

    Barbara McCaffrey Redfin Corp

    111 Maple Ave, Greensboro, MD 21639
  • /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
    • /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

  • /28

    $169,000

    Pending
    • 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
  • /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
    • /30

      Est $342,024

      Not Listed For Sale

      123 Briarwood Cir, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 2,000 Sq Ft
      • Built 2015
      123 Briarwood Cir, Denton, MD 21629

      Last Sold Summary

      • 64 Days On Market

      Last Listing Agent Lou Chirgott Core Maryland Real Estate LLC

  • /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

    $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
    • /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.

  • /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
  • /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
    • /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

  • /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
  • /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 $630,185

    Last Listing Agent Scott Judy Coldwell Banker Waterman Realty

    26067 Goldsboro Rd, Goldsboro, MD 21636
    • /16

      Est $171,927

      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

  • /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
  • /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
    • /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

  • /2

    $149,900

    Pending
    • Studio
    • 1,484 Sq Ft

    112 Noble Ave, Preston, MD 21655

    Investors! Subject to current month-to-month leases this duplex is located in the heart of Preston and close proximity to the school.

    Chuck Mangold Benson & Mangold, LLC

    112 Noble Ave, Preston, MD 21655

Showing Results 41 - 80, Page 2 of 18

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