15,709

Caroline County, MD Homes

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  • /14

    $124,900

    • Land
    • 10.39 Acres
    • $12,021 per Acre

    PARCEL 91 Cool Spring Rd, Marydel, MD 21649

    Ready for you to build your new home! This beautiful lot is already perc approved for a 4=bedroom home. The woods are a great habitat for deer and turkey and other wildlife. This lovely lot is all ready for the new owner to apply for home construction as the buyer has had the survey completed with the SRA noted on it so lots of the necessary paperwork is completed. So come see and come buy and be

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    (410) 650-6268

    PARCEL 91 Cool Spring Rd, Marydel, MD 21649
  • /11

    $1,600 Per Month

    • 3 Beds
    • 1 Bath
    • House for Rent

    7110 Noble Rd, Federalsburg, MD 21632

    This well maintained home is located in a quiet, rural setting, offering peaceful country living while remaining conveniently accessible to the town of Federalsburg and surrounding areas. Ideal for tenants seeking privacy, space, and a serene environment. 3 bedrooms, 1 bath. Hardwood floors.Property HighlightsQuiet country locationPropane furnace heatingOpen surroundings

    7110 Noble Rd, 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 $289,107

    Last Listing Agent Amanda Morgan Brenton Realty Group

    26056 Fox Grape Rd, Greensboro, MD 21639
    • /66

      Est $331,698 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

      • 2% Above List Price
      • $176/SF
      • 71 Days On Market
      • Last Sold Price $325,000
      • Oct 31, 2024

      Last Listing Agent John Tarpley Schwartz Realty, Inc.

  • /34

    $315,000 Open House 5/17

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

    8409 Harmony Rd, Denton, MD 21629

    Tucked away in a peaceful rural setting, this beautifully updated home offers space, privacy, and modern convenience on 1.14 acres. Welcome to 8409 Harmony Road—a truly special property with access from both Harmony Road and the rear of the property via Towers Road, providing added flexibility and convenience. This move-in-ready 3-bedroom, 2-bath home blends thoughtful updates with a functional

    Barbara McCaffrey Redfin Corp

    8409 Harmony Rd, Denton, MD 21629
  • /37

    $2,000 Per Month

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

    22721 Marsh Creek Rd, Preston, MD 21655

    Experience the timeless appeal of country living in this spacious 4-bedroom, 2-bath Sears farmhouse, set on a full acre with scenic views of an active farm. Rich in character, this home showcases classic farmhouse details, including knotty pine walls, hardwood floors, and built-in cabinetry, all complemented by abundant natural light and generously sized rooms. The main level features a large

    Traci Jordan Meredith Fine Properties

    22721 Marsh Creek Rd, Preston, MD 21655
  • /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 $246,968

    Last Listing Agent Brett Schrader Taylor Properties

    229 Oldtown Rd, Goldsboro, MD 21636
    • /19

      Est $210,555 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

      • 11% Above List Price
      • $152/SF
      • 17 Days On Market
      • Last Sold Price $189,900
      • Aug 12, 2024

      Last Listing Agent Karen Clark Clark & Co Realty, LLC

  • /47

    $445,000

    • 4 Beds
    • 2 Baths
    • 1,986 Sq Ft

    25699 Auction Rd, Federalsburg, MD 21632

    Opportunity to purchase a working farm with remodeled residence - from new luxury vinyl plank flooring and Advantech subfloors to a fully replaced middle beam for lasting structural integrity. Nearly all windows and doors are brand new, the heating system has been upgraded to an efficient heat pump, and the electrical system now features a 200-amp panel, a dedicated service line from Choptank

    Barbara McCaffrey Redfin Corp

    25699 Auction Rd, Federalsburg, MD 21632
  • /10

    $2,700 Per Month

    • 3 Beds
    • 2 Baths
    • 1,678 Sq Ft
    • House for Rent

    24101 Asbury Dr, Denton, MD 21629

    FOR RENT – 24101 Asbury Rd, Denton, MDAvailable May$2,700 per month$2,7000 Security DepositSpacious and well-maintained home available in a peaceful country setting just minutes from town in the desirable Asbury community. This property offers comfort, functionality, and modern updates.Property Features:• 3 Bedrooms• 2 Full Bathrooms• New Appliances• 2-Car

    24101 Asbury Dr, Denton, MD 21629
  • /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 $149,192

    Last Listing Agent Gillian Walsh Keller Williams Realty

    28471 Kinder Rd, Federalsburg, MD 21632
    • /5

      Est $514,316 Not Listed For Sale

      24776 Tribbett Cir, Ridgely, MD 21660

      • Built 2025
      24776 Tribbett Cir, Ridgely, MD 21660

      Last Sold Summary

      • 349% Above List Price
      • $53/SF
      • 261 Days On Market
      • Last Sold Price $114,500
      • Oct 15, 2024

      Last Listing Agent Stephan Strothe Washington Fine Properties, LLC

  • /66

    $429,000

    • 5 Beds
    • 2.5 Baths
    • 2,382 Sq Ft

    225 S 2nd St, Denton, MD 21629

    Historic Victorian home with modern updates on a fenced corner lot—5 bedrooms, bonus rooms, deck, and over 2,300 sq ft just blocks from downtown Denton and the Choptank River. Built in 1906, this beautifully updated home offers 2,382 sq ft, 5 bedrooms, and 2.5 baths on a spacious .29-acre corner lot setting with a classic white picket fence and private fenced yard—perfect for outdoor living and

    Barbara McCaffrey Redfin Corp

    225 S 2nd St, Denton, MD 21629
  • /10

    $2,300 Per Month

    • 4 Beds
    • 3.5 Baths
    • Townhouse for Rent

    1901 Blue Heron Dr, Denton, MD 21629

    Spacious 4-bedroom, 3.5-bath home located in a desirable Denton community. This well-maintained property offers plenty of room for comfortable living in a quiet neighborhood while remaining close to schools, shopping, and major routes.Property Features4 Bedrooms / 3.5 BathroomsMonthly Rent: $2,300Security Deposit: $2,300No petsMinimum credit score: 650Non-smoking

    1901 Blue Heron Dr, 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
    • /27

      Est $352,828 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

      • 1% Above List Price
      • $227/SF
      • 25 Days On Market
      • Last Sold Price $349,000
      • Sep 26, 2024

      Last Listing Agent Karen Clark Clark & Co Realty, LLC

  • /57

    $950,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    7805 Dyer Rd, Denton, MD 21629

    Experience the perfect harmony of modern luxury and timeless countryside living with this exceptional 3 bedroom 2.5 bath farmhouse, built in 2022, gracefully set on approximately 62 acres in the heart of Denton, Maryland. Surrounded by a serene, bucolic landscape, this remarkable property offers a rare opportunity to embrace refined rural living without sacrificing contemporary comfort. From the

    Brody Sergent Northrop Realty

    7805 Dyer Rd, Denton, MD 21629
  • /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 $357,182

    Last Listing Agent Dawn O'Day Samson Properties

    3590 Choptank Rd, Preston, MD 21655
    • /10

      Est $411,186 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

      • 13% Above List Price
      • $159/SF
      • 95 Days On Market
      • Last Sold Price $364,900
      • Feb 16, 2024

      Last Listing Agent Michelle DiDonato Island Realty, LLC

  • /41

    $585,000

    • 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
  • /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 $131,214

    Last Listing Agent Kat Thompson Benson & Mangold, LLC.

    13243 Greensboro Rd, Greensboro, MD 21639
    • /21

      Est $223,934 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

      • 4% Above List Price
      • $213/SF
      • 1 Day On Market
      • Last Sold Price $214,900
      • Apr 29, 2024

      Last Listing Agent Austin Whitehead Whitehead Real Estate Exec.

  • /27

    $375,000

    • 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
  • /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 $621,727

    Last Listing Agent Scott Judy Coldwell Banker Waterman Realty

    26067 Goldsboro Rd, Goldsboro, MD 21636
    • /3

      Est $283,557 Not Listed For Sale

      510 Lincoln St, Denton, MD 21629

      • Built 2024
      510 Lincoln St, Denton, MD 21629

      Last Sold Summary

      • 845% Above List Price
      • $23/SF
      • 200 Days On Market
      • Last Sold Price $30,000
      • Mar 06, 2024

      Last Listing Agent Barbara Beaudet Brenton Realty Group

  • /62

    $324,900

    • 3 Beds
    • 2.5 Baths
    • 1,848 Sq Ft

    411 Mallard Dr, Greensboro, MD 21639

    Located in the charming community of Caroline Farms in Greensboro, MD, this delightful Colonial-style home offers a perfect blend of comfort and convenience. Built in 2006, this well-maintained residence boasts 1,848 square feet of living space, providing ample room for relaxation and entertaining. As you approach the home, you'll be greeted by its inviting vinyl siding and a well-manicured front

    Vincent Payne Realty Navigator

    411 Mallard Dr, Greensboro, MD 21639
  • /22

    $115,000 Sold Feb 27, 2026

    208 N Main St, Federalsburg, MD 21632

    • 4 Beds
    • 1.5 Baths
    • 2,668 Sq Ft
    • Built 1913

    Last Sold Summary

    • $43/SF
    • 106 Days On Market

    Current Estimated Value $195,333

    Last Listing Agent Barton Johnson/not int Marshy Hope Realty LLC

    208 N Main St, Federalsburg, MD 21632
    • /26

      Est $136,675 Not Listed For Sale

      13416 Greensboro Rd, Greensboro, MD 21639

      • Built 1971
      13416 Greensboro Rd, Greensboro, MD 21639

      Last Sold Summary

      • 19% Above List Price
      • $160/SF
      • 71 Days On Market
      • Last Sold Price $115,000
      • Dec 27, 2024

      Last Listing Agent Erin Anderson Chesapeake Real Estate Associates, LLC

  • /2

    $79,900

    • Land
    • 9,147 Sq Ft
    • $380,476 per Acre

    6 N Central Ave, Ridgely, MD 21660

    Zoned commercial is this prime lot in the heart of Ridgely and next to the Town Office. Convenient street parking fronting the lot.

    Chuck Jr. Benson and Mangold

    6 N Central Ave, Ridgely, MD 21660
  • /52

    $470,000 Sold Jun 11, 2025

    5569 Harmony Woods Dr, Preston, MD 21655

    • 4 Beds
    • 2.5 Baths
    • 2,909 Sq Ft
    • Built 2005

    Last Sold Summary

    • $162/SF
    • 185 Days On Market

    Current Estimated Value $490,863

    Last Listing Agent Erin Anderson Chesapeake Real Estate Associates, LLC

    5569 Harmony Woods Dr, Preston, MD 21655
    • /16

      Est $161,476 Not Listed For Sale

      4845 Houston Branch Rd, Federalsburg, MD 21632

      4845 Houston Branch Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 1% Above List Price
      • 91 Days On Market
      • Last Sold Price $160,000
      • Jul 12, 2024

      Last Listing Agent Pamela Price Berkshire Hathaway HomeServices PenFed Realty

  • /37

    $325,000 Pending

    • 3 Beds
    • 1 Bath
    • 1,533 Sq Ft

    11305 River Rd, Ridgely, MD 21660

    Price Improvement!! Call today. Charming 3-bedroom, 1-bath rancher offers over 1500 SF of comfortable living space. Several updates have already been completed, making this home move in ready with room to add your own touches. Enjoy peaceful mornings and evenings on the screened-in rear porch, perfect for relaxing while taking in the surrounding wildlife. A great blend of comfort, space and

    Pamela Geib Long & Foster Real Estate, Inc.

    11305 River Rd, Ridgely, MD 21660
  • /34

    $469,000 Sold Oct 10, 2025

    25790 Herring Ln, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 2,132 Sq Ft
    • Built 1989

    Last Sold Summary

    • $220/SF
    • 18 Days On Market

    Current Estimated Value $471,939

    Last Listing Agent Elizabeth Tryon Coldwell Banker Realty

    25790 Herring Ln, Denton, MD 21629
    • /29

      Est $377,705 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

      • 61% Above List Price
      • $59/SF
      • 139 Days On Market
      • Last Sold Price $234,900
      • Nov 06, 2024

      Last Listing Agent Gina Gargeu Century 21 Downtown

  • /22

    $525,000 Pending

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

    8664 Mitchell Rd, Denton, MD 21629

    Nestled on a serene 5.64-acre lot, this charming ranch-style home offers a perfect blend of comfort and modern living in a tranquil rural setting. Built in 2003, (New Roof in January 2026!) this well-maintained residence boasts 2,100 square feet of thoughtfully designed space, featuring three spacious bedrooms and two full bathrooms, ideal for relaxation and everyday living. Step inside to

    Cheryl Knotts Chesapeake Real Estate Associates, LLC

    8664 Mitchell Rd, Denton, MD 21629
  • /26

    $402,000 Sold Dec 09, 2025

    1111 Daylily Ln, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 3,838 Sq Ft
    • Built 2007

    Last Sold Summary

    • $105/SF
    • 7 Days On Market

    Current Estimated Value $415,605

    Last Listing Agent Terri Murray RE/MAX Executive

    1111 Daylily Ln, Denton, MD 21629
    • /24

      Est $349,441 Not Listed For Sale

      5 Seward Rd, Ridgely, MD 21660

      • 3 Beds
      • 2 Baths
      • 1,538 Sq Ft
      • Built 2017
      5 Seward Rd, Ridgely, MD 21660

      Last Sold Summary

      • 8% Above List Price
      • $211/SF
      • 50 Days On Market
      • Last Sold Price $324,000
      • May 24, 2024

      Last Listing Agent Amanda Morgan Brenton Realty Group

  • /41

    $349,900 Under Contract

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

    221 Apple Ln, Preston, MD 21655

    Some homes check one or two boxes. This one checks all of them, and does it for under $350,000.Four bedrooms, two full baths, a fenced backyard, a pool, and open farmland views behind the property. In today's market, that combination at this price point is genuinely rare. This is the kind of home first-time buyers dream about and out-of-area buyers can't believe exists when they start

    Alex Archer Real Broker, LLC - Annapolis

    221 Apple Ln, Preston, MD 21655
  • /30

    $340,000 Sold Aug 20, 2025

    123 Briarwood Cir, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft
    • Built 2015

    Last Sold Summary

    • $170/SF
    • 64 Days On Market

    Current Estimated Value $347,907

    Last Listing Agent Lou Chirgott Core Maryland Real Estate LLC

    123 Briarwood Cir, Denton, MD 21629
    • /5

      Est $79,000 Not Listed For Sale

      328 E Central Ave, Federalsburg, MD 21632

      328 E Central Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 295% Above List Price
      • 28 Days On Market
      • Last Sold Price $20,000
      • Aug 16, 2023

      Last Listing Agent Heather Brummell Keller Williams Realty

Showing Results 41 - 80, Page 2 of 18

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