15,577

Caroline County, MD Homes

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    • /17

      Est $394,352

      Not Listed For Sale

      205 N Main St, Greensboro, MD 21639

      • 5 Beds
      • 3 Baths
      • 3,876 Sq Ft
      • Built 1890
      205 N Main St, Greensboro, MD 21639

      Last Sold Summary

      • 301 Days On Market

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

  • /30

    $348,000

    $7K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft

    8140 Haven St, Denton, MD 21629

    This charming ranch-style home, built in 1986, offers a perfect blend of comfort and functionality. Minutes to Tuckahoe Creek boat ramp! With 1,300 sq. ft. of well-designed space, it features three inviting bedrooms and two full bathrooms, including a primary suite with a walk-in closet and a tub/shower. The traditional floor plan is enhanced by built-ins and ceiling fans, creating a cozy

    Mary Haddaway Benson & Mangold, LLC

    8140 Haven St, Denton, MD 21629
  • /12

    $60,027

    Sold Mar 31, 2026

    21269 Dover Bridge Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1996

    Last Sold Summary

    • $45/SF
    • 64 Days On Market

    Last Listing Agent Donna Harrington Coldwell Banker Realty

    21269 Dover Bridge Rd, Preston, MD 21655
    • /48

      Est $288,973

      Not Listed For Sale

      219 Briarwood Cir, Denton, MD 21629

      • 4 Beds
      • 4 Baths
      • 2,088 Sq Ft
      • Built 2006
      219 Briarwood Cir, Denton, MD 21629

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Kimberly Dixson Coldwell Banker Realty

  • /36

    $414,499

    $15K PRICE DROP
    • 6 Beds
    • 2.5 Baths
    • 2,934 Sq Ft

    304 Tidewater Cir, Preston, MD 21655

    LOVELY Tidewater Farms home with a light, open layout and plenty of space to enjoy. The main level features a spacious breakfast room, open kitchen and great room with a center island, eat-at bar, and gas fireplace. There is also a 19' x 15' bonus room and convenient upstairs laundry.The primary suite offers walk-in closets, a soaking tub, separate shower, and double sink vanity. Outside,

    Judah Fashe Samson Properties

    304 Tidewater Cir, Preston, MD 21655
  • /13

    $230,000

    Sold Feb 27, 2026

    1202 Blue Heron Dr, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 1,753 Sq Ft
    • Built 2004

    Last Sold Summary

    • 2% Below List Price
    • $131/SF
    • 46 Days On Market

    Current Estimated Value $231,291

    Last Listing Agent SHANTA PHILLIPS EXP Realty, LLC

    1202 Blue Heron Dr, Denton, MD 21629
    • /9

      Est $241,000

      Not Listed For Sale

      25782 Goldsboro Rd, Goldsboro, MD 21636

      • 2 Beds
      • 1 Bath
      • 1,386 Sq Ft
      • Built 1910
      25782 Goldsboro Rd, Goldsboro, MD 21636

      Last Sold Summary

      • 46 Days On Market

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

  • /35

    $250,000

    $15K PRICE DROP Pending
    • 3 Beds
    • 2.5 Baths
    • 1,584 Sq Ft

    530 Vaughn Ave, Greensboro, MD 21639

    **Seller is offering $2,500 towards buyers closing costs with a full price offer!** Welcome home to this beautifully updated 3-bedroom, 2.5-bath home built by Gemcraft Homes in 2002. Freshly painted throughout in 2026, this move-in-ready home also features brand-new luxury vinyl plank flooring on the main level and new carpet throughout the second floor, offering a fresh, modern feel from the

    Hunter Geary Hyatt & Company Real Estate, LLC

    530 Vaughn Ave, Greensboro, MD 21639
  • /16

    $215,000

    Sold Oct 24, 2025

    522 Lincoln St, Denton, MD 21629

    • 2 Beds
    • 1 Bath
    • 640 Sq Ft
    • Built 1961

    Last Sold Summary

    • $336/SF
    • 10 Days On Market

    Current Estimated Value $210,760

    Last Listing Agent Amanda Morgan Brenton Realty Group

    522 Lincoln St, Denton, MD 21629
    • /11

      Est $290,274

      Not Listed For Sale

      408 Maple Ave, Ridgely, MD 21660

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1978
      408 Maple Ave, Ridgely, MD 21660

      Last Sold Summary

      • 62 Days On Market

      Last Listing Agent Bonnie Duley Long & Foster Real Estate, Inc.

  • /14

    $282,990

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft

    Curtis Plan at Kinnamon Meadows, Greensboro, MD 21639

    The Curtis is a 1,182 square foot, cottage-style ranch home with three bedrooms and two bathrooms. As you enter the home through the front porch, this thoughtfully designed home has a grand open concept living area that leads into the spacious kitchen. To the right, a long, main hallway allows for the two guest bedrooms and guest bathroom to be separate from the living areas of the home. Along

    D.R. Horton Builder
    103 Park Ave Unit 36203276, Greensboro, MD 21639
  • /4

    $110,000

    Sold Dec 15, 2025

    0 Whiteleysburg Rd Unit DEKT2042216, Harrington, DE 19952

    • Land
    • 2 Acres
    • $55,000 per Acre

    Last Sold Summary

    • 1 Day On Market

    Last Listing Agent Amy Torbert Diamond State Cooperative LLC

    0 Whiteleysburg Rd Unit DEKT2042216, Harrington, DE 19952
    • /20

      Est $253,247

      Not Listed For Sale

      411 N 6th St, Denton, MD 21629

      • 3 Beds
      • 1 Bath
      • 1,364 Sq Ft
      • Built 1900
      411 N 6th St, Denton, MD 21629

      Last Sold Summary

      • 115 Days On Market

      Last Listing Agent Kat Thompson Benson & Mangold, LLC.

  • /24

    $220,000

    $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    122 Julie Ln, Federalsburg, MD 21632

    Welcome to this beautifully maintained newer town home that has been virtually staged was built in late 2025, in the charming Riverwalk community of Federalsburg. Offering 3 bedrooms, 2.5 bathrooms, and modern construction, this home combines today's sought-after finishes with the warmth and small-town charm that make Maryland's Eastern Shore such a desirable place to call home. Close to

    Donna Hollifield Remax Vision

    122 Julie Ln, Federalsburg, MD 21632
  • /19

    $315,000

    Sold Jan 09, 2026

    25607 Garey Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 920 Sq Ft
    • Built 1998

    Last Sold Summary

    • $342/SF
    • 39 Days On Market

    Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

    25607 Garey Rd, Denton, MD 21629
    • /13

      Est $207,062

      Not Listed For Sale

      101 Vaughn Ave, Greensboro, MD 21639

      • 2 Beds
      • 1 Bath
      • 1,004 Sq Ft
      • Built 1950
      101 Vaughn Ave, Greensboro, MD 21639

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Kat Thompson Benson & Mangold, LLC.

  • /67

    $629,000

    $50K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,744 Sq Ft

    132 Deep Shore Rd, Denton, MD 21629

    Welcome to 132 Deep Shore Rd—an inviting homestead set on more than 3 acres of beautifully maintained gardens, thoughtfully designed outdoor spaces, and versatile outbuildings. From greenhouse and herb beds to a dedicated drying room and casual nooks for lounging, every corner invites you to savor the seasons.Inside, this spacious home offers over 2,700 sq ft with 4 bedrooms and 2.5

    Roger Boyce Chesapeake Real Estate Associates, LLC

    132 Deep Shore Rd, Denton, MD 21629
  • /16

    $230,000

    Sold Jan 30, 2026

    0 Shore Highway-404 Unit MDCM2004050, Denton, MD 21629

    • Land
    • 3.4 Acres
    • $67,647 per Acre

    Last Sold Summary

    • 30% Below List Price
    • 631 Days On Market

    Last Listing Agent Eddie Matthews Benson & Mangold, LLC

    0 Shore Highway-404 Unit MDCM2004050, Denton, MD 21629
    • /32

      Est $450,392

      Not Listed For Sale

      288 Tidewater Cir, Preston, MD 21655

      • 4 Beds
      • 2.5 Baths
      • 2,842 Sq Ft
      • Built 2006
      288 Tidewater Cir, Preston, MD 21655

      Last Sold Summary

      • 56 Days On Market

      Last Listing Agent Richard Pullin Weichert, REALTORS

  • /27

    $315,000

    $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,212 Sq Ft

    104 Chambers St, Federalsburg, MD 21632

    Ready to own without the stress? Move in and start your life, not your renovation. This fully renovated home is one your friends will be drooling over. The kitchen steals the show: soft-close navy cabinets with gold hardware and quartz countertops, stainless steel appliances, a deep kitchen sink, stylish floating shelves, and a crisp white tile backsplash. It's the kind of space that makes

    Kaitlyn Collins Benson & Mangold, LLC

    104 Chambers St, Federalsburg, MD 21632
  • /108

    $1,200,000

    Sold Jan 21, 2026

    14271 Cedar Ln, Greensboro, MD 21639

    • 6 Beds
    • 3 Baths
    • 3,756 Sq Ft
    • Built 1998

    Last Sold Summary

    • $319/SF
    • 245 Days On Market

    Current Estimated Value $1,095,860

    Last Listing Agent Travis Gray Engel & Völkers Annapolis

    14271 Cedar Ln, Greensboro, MD 21639
    • /15

      Est $400,106

      Not Listed For Sale

      1104 Canvasback Ln, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,988 Sq Ft
      • Built 2006
      1104 Canvasback Ln, Denton, MD 21629

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Kevin Waterman Coldwell Banker Waterman Realty

  • /44

    $575,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 2,426 Sq Ft

    22733 Squire Ln, Queen Anne, MD 21657

    You'll love this custom home nestled on 2.13 private acres, offering over 2,500 square feet of thoughtfully designed living space with 4 bedrooms and 2.5 baths. The open floor plan is highlighted by rich Brazilian hardwood floors, cathedral ceiling, and a welcoming great room anchored by a dramatic floor-to-ceiling brick fireplace.The spacious kitchen opens seamlessly to the great room

    Jimmy White Long & Foster Real Estate, Inc.

    22733 Squire Ln, Queen Anne, MD 21657
  • /52

    $465,000

    Sold Jun 16, 2026

    14418 Poplar St, Goldsboro, MD 21636

    • 2 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 1989

    Last Sold Summary

    • 5% Above List Price
    • $252/SF
    • 6 Days On Market

    Current Estimated Value $455,942

    Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

    14418 Poplar St, Goldsboro, MD 21636
    • /19

      Est $329,718

      Not Listed For Sale

      6 Oak St, Ridgely, MD 21660

      • 3 Beds
      • 2 Baths
      • 1,480 Sq Ft
      • Built 1979
      6 Oak St, Ridgely, MD 21660

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Heather Brummell Keller Williams Realty

  • /70

    $359,900

    • 3 Beds
    • 2 Baths
    • 2,160 Sq Ft

    412 N Main St, Greensboro, MD 21639

    RENOVATED RANCH ON 0.73 ACRE WITH IN-GROUND POOL & 3 GARAGES!Welcome to this charming ranch-style home, where classic character meets modern comfort. This spacious residence features three inviting bedrooms and two full bathrooms, providing plenty of room for both everyday living and relaxation. The beautifully renovated kitchen and bathrooms, along with fresh interior and exterior paint,

    neveela gondal Keller Williams Realty Central-Delaware

    412 N Main St, Greensboro, MD 21639
  • /2

    $289,990

    Sold Sep 25, 2025

    111 Parkland Rd, Greensboro, MD 21639

    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft

    Last Sold Summary

    • $199/SF
    • 13 Days On Market

    Last Listing Agent Justin Wood D.R. Horton Realty of Virginia, LLC

    111 Parkland Rd, Greensboro, MD 21639
    • /36

      Est $474,310

      Not Listed For Sale

      11412 Cecil Ct, Greensboro, MD 21639

      • 4 Beds
      • 2.5 Baths
      • 2,100 Sq Ft
      • Built 2005
      11412 Cecil Ct, Greensboro, MD 21639

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Deborah Shiley Long & Foster Real Estate, Inc.

  • /48

    $600,000

    • 6 Beds
    • 3.5 Baths
    • 3,592 Sq Ft

    11592 Holly Rd, Ridgely, MD 21660

    Welcome to 11592 Holly Road in Ridgely, MD! This spacious 6-bedroom, 3.5-bath home offers plenty of room inside and out, with a flexible layout to fit a variety of needs.Inside, you'll find a bright kitchen with premium appliances, a comfortable living room with a gas fireplace, and a primary suite featuring a separate sitting area and attached office. The home also includes an in-law

    Jarnell Foster Samson Properties

    11592 Holly Rd, Ridgely, MD 21660
  • /74

    $740,000

    Sold Jan 20, 2026

    3485 Gallagher Rd, Preston, MD 21655

    • 3 Beds
    • 2.5 Baths
    • 3,326 Sq Ft
    • Built 2003

    Last Sold Summary

    • $222/SF
    • 5 Days On Market

    Current Estimated Value $737,260

    Last Listing Agent Lish Gannon Dulin Benson & Mangold, LLC

    3485 Gallagher Rd, Preston, MD 21655
    • /32

      Est $251,361

      Not Listed For Sale

      203 Greenridge Rd, Federalsburg, MD 21632

      • 3 Beds
      • 2 Baths
      • 1,479 Sq Ft
      • Built 1938
      203 Greenridge Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Meme ELLIS Keller Williams Realty

  • /60

    $1,250,000

    $250K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,358 Sq Ft

    23071 Tuckahoe Springs Dr, Denton, MD 21629

    New price improvement! Beautifully positioned along the deep protected waters of the Tuckahoe, this exceptional residence has been transformed through an extensive renovation that blends timeless design with comfortable waterfront living. Every improvement was carefully planned, resulting in a home that feels as inviting as it is impressive. The heart of the home is the custom kitchen, where blue

    Sydney Johnson Cohee Sharon Real Estate P.C.

    23071 Tuckahoe Springs Dr, Denton, MD 21629
  • /44

    $367,000

    Sold Aug 14, 2026

    102 Lister Ln, Ridgely, MD 21660

    • 4 Beds
    • 3 Baths
    • 2,612 Sq Ft
    • Built 2005

    Last Sold Summary

    • 5% Below List Price
    • $141/SF
    • 19 Days On Market

    Current Estimated Value $397,378

    Last Listing Agent Kristy Collins Douglas Realty, LLC

    102 Lister Ln, Ridgely, MD 21660
    • /24

      Est $228,150

      Not Listed For Sale

      108 Liberty Rd, Federalsburg, MD 21632

      • 3 Beds
      • 1.5 Baths
      • 1,756 Sq Ft
      • Built 1890
      108 Liberty Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 177 Days On Market

      Last Listing Agent Carolina Mosquera Weichert, REALTORS

  • /74

    $599,900

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,938 Sq Ft

    23130 Sparks Rd, Ridgely, MD 21660

    Robert Walker McClain-Williamson Realty, LLC

    23130 Sparks Rd, Ridgely, MD 21660
  • /52

    $390,000

    Sold Oct 23, 2025

    8556 Tuckahoe Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2001

    Last Sold Summary

    • $290/SF
    • 42 Days On Market

    Current Estimated Value $394,883

    Last Listing Agent Kathleen Armiger Coldwell Banker Realty

    8556 Tuckahoe Rd, Denton, MD 21629
    • /11

      Est $313,825

      Not Listed For Sale

      505 S 2nd St, Denton, MD 21629

      • 3 Beds
      • 1.5 Baths
      • 2,058 Sq Ft
      • Built 1941
      505 S 2nd St, Denton, MD 21629

      Last Sold Summary

      • 12 Days On Market

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

  • /38

    $375,000

    • 4 Beds
    • 2.5 Baths
    • 2,552 Sq Ft

    4 N Maryland Ave, Ridgely, MD 21660

    Welcome to 4 N Maryland Ave in Ridgely! This spacious 4-bedroom, 2.5-bath home offers 2,552 square feet of living space on approximately 0.21 acres. The home features a two-story layout, fireplace, open and enclosed porch areas, and a private pool—perfect for relaxing and entertaining. Conveniently located in the Town of Ridgely, this property offers plenty of space and potential to make it your

    Heather Brummell Keller Williams Realty

    4 N Maryland Ave, Ridgely, MD 21660
  • /28

    $219,990

    Sold Oct 23, 2025

    124 Julie Ln, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 1,365 Sq Ft
    • Built 2025

    Last Sold Summary

    • $161/SF
    • 19 Days On Market

    Last Listing Agent Justin Wood D.R. Horton Realty of Virginia, LLC

    124 Julie Ln, Federalsburg, MD 21632
    • /20

      Est $223,189

      Not Listed For Sale

      217 Greenridge Rd, Federalsburg, MD 21632

      • 2 Beds
      • 1.5 Baths
      • 1,276 Sq Ft
      • Built 1950
      217 Greenridge Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Shirley Coulbourne Coldwell Banker Realty

Showing Results 481 - 520, Page 13 of 18

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