15,675

Caroline County, MD Homes

Section Image Section Image
  • 203 Bernard Ave, Federalsburg, MD 21632
    203 Bernard Ave, Federalsburg, MD 21632
    203 Bernard Ave, Federalsburg, MD 21632
    /22

    $225,000 Sold Jun 18, 2025

    203 Bernard Ave, Federalsburg, MD 21632

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1972

    Last Sold Summary

    • $213/SF
    • 31 Days On Market

    Current Estimated Value $237,790

    Last Listing Agent Valerie Brown Charles C. Powell, Inc. Realtors

    203 Bernard Ave, Federalsburg, MD 21632
    • 202B Maple Ave, Federalsburg, MD 21632
      202B Maple Ave, Federalsburg, MD 21632
      202B Maple Ave, Federalsburg, MD 21632
      /23

      Est $181,976 Not Listed For Sale

      • Studio
      • 1,640 Sq Ft

      202B Maple Ave, Federalsburg, MD 21632

      202B Maple Ave, Federalsburg, MD 21632
  • 204 Academy Ave, Federalsburg, MD 21632
    204 Academy Ave, Federalsburg, MD 21632
    204 Academy Ave, Federalsburg, MD 21632
    /4

    $24,500

    • 2 Beds
    • 1 Bath
    • 1,024 Sq Ft

    204 Academy Ave, Federalsburg, MD 21632

    Investor special! This property is being sold AS-IS and is priced for land value or a full renovation. The existing structure requires extensive repairs or complete tear-down—ideal for experienced builders, contractors, or savvy investors looking for a project. Buyer to verify zoning, permits, potential use. Buyer Broker/Agent and/or Buyer must do their own due diligence to verify if the existing

    Mike Dunn Keller Williams Realty Delmarva

    204 Academy Ave, Federalsburg, MD 21632
  • 148 Main St, Preston, MD 21655
    148 Main St, Preston, MD 21655
    148 Main St, Preston, MD 21655
    /44

    $220,000 Sold Oct 30, 2025

    148 Main St, Preston, MD 21655

    • 4 Beds
    • 2 Baths
    • 2,884 Sq Ft
    • Built 1880

    Last Sold Summary

    • $76/SF
    • 69 Days On Market

    Current Estimated Value $231,818

    Last Listing Agent Cheri Bruce-Phipps TTR Sotheby's International Realty

    148 Main St, Preston, MD 21655
    • 201 Church St, Greensboro, MD 21639
      201 Church St, Greensboro, MD 21639
      201 Church St, Greensboro, MD 21639
      /52

      Est $381,926 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,559 Sq Ft

      201 Church St, Greensboro, MD 21639

      201 Church St, Greensboro, MD 21639
  • 12459 Kibler Rd, Greensboro, MD 21639
    12459 Kibler Rd, Greensboro, MD 21639
    12459 Kibler Rd, Greensboro, MD 21639
    /35

    $599,000

    • 4 Beds
    • 2 Baths
    • 1,771 Sq Ft

    12459 Kibler Rd, Greensboro, MD 21639

    Outstanding small farm property on quiet country road! This spacious home features 3-4 bedrooms and two baths, kitchen with new stainless steel appliances, breakfast bar and dining area. The large living room with wood floors over look the expansive front yard and opens to the front porch where you can enjoy your morning coffee. In the rear of the home there is a large family room that offers a

    Marcia Rostien Long & Foster Real Estate, Inc.

    12459 Kibler Rd, Greensboro, MD 21639
  • 510 Pintail St, Greensboro, MD 21639
    510 Pintail St, Greensboro, MD 21639
    510 Pintail St, Greensboro, MD 21639
    /58

    $345,000 Sold Jul 30, 2025

    510 Pintail St, Greensboro, MD 21639

    • 5 Beds
    • 2.5 Baths
    • 1,984 Sq Ft
    • Built 2005

    Last Sold Summary

    • $174/SF
    • 91 Days On Market

    Current Estimated Value $363,965

    Last Listing Agent Jon Fleming Weichert Realtors - Blue Ribbon

    510 Pintail St, Greensboro, MD 21639
    • 1513 Cattail Commons Way, Denton, MD 21629
      1513 Cattail Commons Way, Denton, MD 21629
      1513 Cattail Commons Way, Denton, MD 21629
      /40

      Est $416,645 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,424 Sq Ft

      1513 Cattail Commons Way, Denton, MD 21629

      1513 Cattail Commons Way, Denton, MD 21629
  • 14857 Oakland Rd, Ridgely, MD 21660
    14857 Oakland Rd, Ridgely, MD 21660
    14857 Oakland Rd, Ridgely, MD 21660
    /14

    $270,000

    • 3 Beds
    • 1 Bath
    • 720 Sq Ft

    14857 Oakland Rd, Ridgely, MD 21660

    Peacefully located in the countryside of Ridgely, MD, this 3-bedroom, 1-bath home sits on 4.6 acres, offering privacy and room to grow! Features include granite countertops, stainless steel appliances, a spacious updated bathroom, and hardwood floors in the living and dining rooms. Ample outdoor space provides endless possibilities for enjoyment or future use. Whether you’re dreaming of a

    VALENCIA BOYD Keller Williams Preferred Properties

    14857 Oakland Rd, Ridgely, MD 21660
  • 208 S 3rd St, Denton, MD 21629
    208 S 3rd St, Denton, MD 21629
    /2

    $150,000 Sold Jan 27, 2026

    208 S 3rd St, Denton, MD 21629

    • 3 Beds
    • 1 Bath
    • 1,136 Sq Ft
    • Built 1900

    Last Sold Summary

    • 25% Below List Price
    • $132/SF
    • 11 Days On Market

    Last Listing Agent SALLY KERCHNER Benson & Mangold, LLC

    208 S 3rd St, Denton, MD 21629
    • 10903 Collinswood Dr, Denton, MD 21629
      10903 Collinswood Dr, Denton, MD 21629
      10903 Collinswood Dr, Denton, MD 21629
      /37

      Est $874,665 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 4,404 Sq Ft

      10903 Collinswood Dr, Denton, MD 21629

      10903 Collinswood Dr, Denton, MD 21629
  • 103 Park Ave Unit 36203276, Greensboro, MD 21639
    103 Park Ave Unit 36203276, Greensboro, MD 21639
    103 Park Ave Unit 36203276, Greensboro, MD 21639
    /3

    $276,990 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
  • 512 Lincoln St, Denton, MD 21629
    512 Lincoln St, Denton, MD 21629
    512 Lincoln St, Denton, MD 21629
    /20

    $294,000 Sold Oct 24, 2025

    512 Lincoln St, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,420 Sq Ft
    • Built 2024

    Last Sold Summary

    • $207/SF
    • 28 Days On Market

    Last Listing Agent Amy Betts Coldwell Banker Realty

    512 Lincoln St, Denton, MD 21629
    • 508 N 6th St, Denton, MD 21629
      508 N 6th St, Denton, MD 21629
      508 N 6th St, Denton, MD 21629
      /15

      Est $258,161 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,192 Sq Ft

      508 N 6th St, Denton, MD 21629

      508 N 6th St, Denton, MD 21629
  • 21682 Dover Bridge Rd, Preston, MD 21655
    21682 Dover Bridge Rd, Preston, MD 21655
    21682 Dover Bridge Rd, Preston, MD 21655
    /23

    $749,000 Pending

    21682 Dover Bridge Rd, Preston, MD 21655

    Jim Corson Benson & Mangold, LLC

    21682 Dover Bridge Rd, Preston, MD 21655
  • 22716 Havercamp Rd, Preston, MD 21655
    22716 Havercamp Rd, Preston, MD 21655
    22716 Havercamp Rd, Preston, MD 21655
    /33

    $435,000 Sold Aug 29, 2025

    22716 Havercamp Rd, Preston, MD 21655

    • 3 Beds
    • 2.5 Baths
    • 2,192 Sq Ft
    • Built 2007

    Last Sold Summary

    • $198/SF
    • 72 Days On Market

    Current Estimated Value $458,233

    Last Listing Agent Chuck Mangold Benson & Mangold, LLC

    22716 Havercamp Rd, Preston, MD 21655
    • 1140 Canvasback Ln, Denton, MD 21629
      1140 Canvasback Ln, Denton, MD 21629
      1140 Canvasback Ln, Denton, MD 21629
      /39

      Est $417,738 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,602 Sq Ft

      1140 Canvasback Ln, Denton, MD 21629

      1140 Canvasback Ln, Denton, MD 21629
  • 8 W Liberty St, Ridgely, MD 21660
    8 W Liberty St, Ridgely, MD 21660
    8 W Liberty St, Ridgely, MD 21660
    /55

    $429,900

    • 5 Beds
    • 2 Baths
    • 4,060 Sq Ft

    8 W Liberty St, Ridgely, MD 21660

    Welcome to this beautiful updated Custom Built Brick 5-bedroom, 2-bath home nestled on a generous double corner lot in the quaint town of Ridgely. Combining classic charm with modern updates. This property offers comfort and convenience—perfect for growing families or those who love to entertain. Property hightlights include: Updated kitchen featuring brand-new stainless steel appliances, new

    Barbara Blosser Long & Foster Real Estate, Inc.

    8 W Liberty St, Ridgely, MD 21660
  • 305 Maple Ave, Federalsburg, MD 21632
    305 Maple Ave, Federalsburg, MD 21632
    305 Maple Ave, Federalsburg, MD 21632
    /18

    $169,900 Sold Mar 21, 2025

    305 Maple Ave, Federalsburg, MD 21632

    • 3 Beds
    • 1 Bath
    • 1,392 Sq Ft
    • Built 1940

    Last Sold Summary

    • $122/SF
    • 43 Days On Market

    Current Estimated Value $179,312

    Last Listing Agent Traci Jordan Meredith Fine Properties

    305 Maple Ave, Federalsburg, MD 21632
    • 1238 Painted Fern Rd, Denton, MD 21629
      1238 Painted Fern Rd, Denton, MD 21629
      1238 Painted Fern Rd, Denton, MD 21629
      /19

      Est $388,522 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,492 Sq Ft

      1238 Painted Fern Rd, Denton, MD 21629

      1238 Painted Fern Rd, Denton, MD 21629
  • 1233 Painted Fern Rd, Denton, MD 21629
    1233 Painted Fern Rd, Denton, MD 21629
    1233 Painted Fern Rd, Denton, MD 21629
    /4

    $459,500 Under Contract

    • 5 Beds
    • 3.5 Baths
    • 4,222 Sq Ft

    1233 Painted Fern Rd, Denton, MD 21629

    Welcome to this spacious beautiful family home in a desirable subdivision. This 5 bedroom 3.5 bathroom home is inviting the inut you walk through the door. This home boats a first and second floor primary suite tha is perfect for in laws or guests. If closet space is essential to you than you will love the closet space in the 2nd floor primary suite. It's a dream space for anyone with an

    Lesley Jackson EXIT Sunshine Realty

    1233 Painted Fern Rd, Denton, MD 21629
  • 104 Sunset Blvd, Ridgely, MD 21660
    104 Sunset Blvd, Ridgely, MD 21660
    104 Sunset Blvd, Ridgely, MD 21660
    /28

    $275,000 Sold Jul 08, 2025

    104 Sunset Blvd, Ridgely, MD 21660

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft
    • Built 1992

    Last Sold Summary

    • $273/SF
    • 215 Days On Market

    Current Estimated Value $288,796

    Last Listing Agent Marcia Rostien Long & Foster Real Estate, Inc.

    104 Sunset Blvd, Ridgely, MD 21660
    • 1306 Blue Heron Dr, Denton, MD 21629
      1306 Blue Heron Dr, Denton, MD 21629
      1306 Blue Heron Dr, Denton, MD 21629
      /45

      Est $244,167 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,620 Sq Ft

      1306 Blue Heron Dr, Denton, MD 21629

      1306 Blue Heron Dr, Denton, MD 21629
  • 506 Park Ave, Ridgely, MD 21660
    506 Park Ave, Ridgely, MD 21660
    506 Park Ave, Ridgely, MD 21660
    /59

    $298,000

    • 2 Beds
    • 1 Bath
    • 1,528 Sq Ft

    506 Park Ave, Ridgely, MD 21660

    Welcome to this delightful 2-bedroom, 1-bath rancher nestled in the heart of Ridgely. Perfectly positioned on a spacious double lot, this home offers abundant outdoor space—ideal for gardening, entertaining, or future expansion. A brand-new roof adds peace of mind and long-term value. Step inside to discover a bright and functional layout featuring a sun-drenched sunroom, a cozy living room with

    Lisa Lynch Keller Williams Realty

    506 Park Ave, Ridgely, MD 21660
  • 110 Parkland Rd, Greensboro, MD 21639
    110 Parkland Rd, Greensboro, MD 21639
    /2

    $286,990 Sold Aug 15, 2025

    110 Parkland Rd, Greensboro, MD 21639

    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft
    • Built 2025

    Last Sold Summary

    • $197/SF
    • 7 Days On Market

    Last Listing Agent Kathleen Cassidy D R Horton Realty of Virginia LLC

    110 Parkland Rd, Greensboro, MD 21639
    • 203 Wood Duck Dr, Greensboro, MD 21639
      203 Wood Duck Dr, Greensboro, MD 21639
      203 Wood Duck Dr, Greensboro, MD 21639
      /54

      Est $343,528 Not Listed For Sale

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

      203 Wood Duck Dr, Greensboro, MD 21639

      203 Wood Duck Dr, Greensboro, MD 21639
  • 536 Gay St, Denton, MD 21629
    536 Gay St, Denton, MD 21629
    536 Gay St, Denton, MD 21629
    /3

    $110,000 Pending

    • 3 Beds
    • 1 Bath
    • 1,032 Sq Ft

    536 Gay St, Denton, MD 21629

    Property will be sold in as/ is condition. General Commercial zoning.

    Diane Wenk Wright Real Estate

    536 Gay St, Denton, MD 21629
  • 5480 Bethlehem Rd, Preston, MD 21655
    5480 Bethlehem Rd, Preston, MD 21655
    5480 Bethlehem Rd, Preston, MD 21655
    /34

    $324,000 Sold Mar 03, 2025

    5480 Bethlehem Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1996

    Last Sold Summary

    • $263/SF
    • 9 Days On Market

    Current Estimated Value $353,318

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    5480 Bethlehem Rd, Preston, MD 21655
    • 322 Maple Ave, Federalsburg, MD 21632
      322 Maple Ave, Federalsburg, MD 21632
      322 Maple Ave, Federalsburg, MD 21632
      /20

      Est $240,318 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,812 Sq Ft

      322 Maple Ave, Federalsburg, MD 21632

      322 Maple Ave, Federalsburg, MD 21632
  • 28402 Liden School Rd, Denton, MD 21629
    28402 Liden School Rd, Denton, MD 21629
    28402 Liden School Rd, Denton, MD 21629
    /60

    $699,000

    • 3 Beds
    • 2 Baths

    28402 Liden School Rd, Denton, MD 21629

    Private serene living at its finest! This property has it all -- gorgeous rancher with 3 BR and 2 full baths; large pantry in the kitchen, family room with pellet stove and brick fireplace that can burn wood if buyer desires to do so; two large walk-in closets in primary bedroom; so much to mention here that you really must come see for yourself -- fresh air, peace and quiet, birds singing,

    Bonnie Duley Long & Foster Real Estate, Inc.

    28402 Liden School Rd, Denton, MD 21629
  • 22415 Hillsboro Rd, Denton, MD 21629
    22415 Hillsboro Rd, Denton, MD 21629
    /2

    $70,000 Sold Jan 09, 2026

    22415 Hillsboro Rd, Denton, MD 21629

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft
    • Built 1910

    Last Sold Summary

    • $61/SF
    • 17 Days On Market

    Last Listing Agent TAMMY GREEN Samson Properties

    22415 Hillsboro Rd, Denton, MD 21629
    • 12171 River Rd, Ridgely, MD 21660
      12171 River Rd, Ridgely, MD 21660
      12171 River Rd, Ridgely, MD 21660
      /26

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,568 Sq Ft

      12171 River Rd, Ridgely, MD 21660

      12171 River Rd, Ridgely, MD 21660
  • 5585 Harmony Woods Dr, Preston, MD 21655
    5585 Harmony Woods Dr, Preston, MD 21655
    5585 Harmony Woods Dr, Preston, MD 21655
    /54

    $549,000

    • 4 Beds
    • 2.5 Baths
    • 3,442 Sq Ft

    5585 Harmony Woods Dr, Preston, MD 21655

    Set on a private, wooded 1.37± acre lot in Harmony Woods, this beautifully maintained home offers a warm, inviting layout with abundant natural light and thoughtful updates throughout. A welcoming front porch leads into the main level with hardwood floors, detailed trim work, and easy flow from the kitchen and breakfast area to the living room with a wood-burning fireplace. Full-view doors open

    Georgi Chauvin Benson & Mangold, LLC

    5585 Harmony Woods Dr, Preston, MD 21655
  • 123 Park Ave, Greensboro, MD 21639

    $274,990 Sold Dec 16, 2025

    123 Park Ave, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $233/SF
    • 27 Days On Market

    D.R. Horton Kinnamon Meadows

    123 Park Ave, Greensboro, MD 21639
    • 1622 Blue Heron Dr, Denton, MD 21629
      1622 Blue Heron Dr, Denton, MD 21629
      1622 Blue Heron Dr, Denton, MD 21629
      /30

      Est $280,402 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 2,244 Sq Ft

      1622 Blue Heron Dr, Denton, MD 21629

      1622 Blue Heron Dr, Denton, MD 21629
  • PARCEL 91 Cool Spring Rd, Marydel, MD 21649
    PARCEL 91 Cool Spring Rd, Marydel, MD 21649
    PARCEL 91 Cool Spring Rd, Marydel, MD 21649
    /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 3-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

    Bonnie Duley Long & Foster Real Estate, Inc.

    PARCEL 91 Cool Spring Rd, Marydel, MD 21649
  • 11921 Greensboro Rd, Greensboro, MD 21639
    11921 Greensboro Rd, Greensboro, MD 21639
    11921 Greensboro Rd, Greensboro, MD 21639
    /30

    $275,000 Sold Feb 18, 2025

    11921 Greensboro Rd, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1965

    Last Sold Summary

    • $205/SF
    • 39 Days On Market

    Current Estimated Value $299,742

    Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

    11921 Greensboro Rd, Greensboro, MD 21639
    • 326 E Central Ave, Federalsburg, MD 21632
      326 E Central Ave, Federalsburg, MD 21632
      326 E Central Ave, Federalsburg, MD 21632
      /3

      Est $78,000 Not Listed For Sale

      326 E Central Ave, Federalsburg, MD 21632

      326 E Central Ave, Federalsburg, MD 21632
  • 22005 Main St, Hillsboro, MD 21641
    22005 Main St, Hillsboro, MD 21641
    22005 Main St, Hillsboro, MD 21641
    /74

    $545,000

    • 3 Beds
    • 3 Baths
    • 3,088 Sq Ft

    22005 Main St, Hillsboro, MD 21641

    This fine, brick dwelling originating from the18th c. is situated in Hillsboro on Maryland's peaceful Eastern Shore. Hillsboro, nestled along the Tuckahoe River, conveniently located to all that is important to the Eastern Shore's sought-after lifestyle. The WILLIAM SMITH HOUSE, built in 1794, exemplifies the world of a successful Grain Merchant living in an important hub for grain and tobacco.

    Nancy McGuire Maryland Heritage Properties

    22005 Main St, Hillsboro, MD 21641
  • 11255 Maplewood Dr, Ridgely, MD 21660
    11255 Maplewood Dr, Ridgely, MD 21660
    11255 Maplewood Dr, Ridgely, MD 21660
    /19

    $440,000 Sold Mar 11, 2025

    11255 Maplewood Dr, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,712 Sq Ft
    • Built 2020

    Last Sold Summary

    • $257/SF

    Current Estimated Value $467,237

    Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

    11255 Maplewood Dr, Ridgely, MD 21660

Showing Results 361 - 400, Page 10 of 18

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