15,718

Caroline County, MD Homes

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  • 0 Cool Spring Rd Unit MDCM2005520, Marydel, MD 21649
    0 Cool Spring Rd Unit MDCM2005520, Marydel, MD 21649
    0 Cool Spring Rd Unit MDCM2005520, Marydel, MD 21649
    /49

    $750,000

    Sold Nov 12, 2025

    0 Cool Spring Rd Unit MDCM2005520, Marydel, MD 21649

    • Land
    • 187 Acres
    • $4,011 per Acre

    Last Sold Summary

    • 139 Days On Market

    Last Listing Agent Benjamin Alder The Land Group

    0 Cool Spring Rd Unit MDCM2005520, Marydel, MD 21649
    • 128 Mill St, Greensboro, MD 21639
      128 Mill St, Greensboro, MD 21639
      128 Mill St, Greensboro, MD 21639
      /7

      Est $290,758

      Not Listed For Sale

      128 Mill St, Greensboro, MD 21639

      • 3 Beds
      • 1 Bath
      • 1,890 Sq Ft
      • Built 1981
      128 Mill St, Greensboro, MD 21639

      Last Sold Summary

      • 18 Days On Market

  • 208 Oriole Ave, Ridgely, MD 21660
    208 Oriole Ave, Ridgely, MD 21660
    208 Oriole Ave, Ridgely, MD 21660
    /27

    $319,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    208 Oriole Ave, Ridgely, MD 21660

    Charming 3-bedroom, 2-bath rancher located in Ridgely! Inside, you’ll find comfortable one-level living with a functional open layout connecting the living room and kitchen, complete with stainless steel appliances. The spacious primary suite features a large en-suite bath and private doors leading directly to the backyard deck. Two additional generously sized bedrooms provide plenty of space for

    Alicia Gannon Dulin Benson & Mangold, LLC

    208 Oriole Ave, Ridgely, MD 21660
  • 130 Walnut St, Ridgely, MD 21660
    130 Walnut St, Ridgely, MD 21660
    130 Walnut St, Ridgely, MD 21660
    /27

    $369,000

    Sold Nov 17, 2025

    130 Walnut St, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,548 Sq Ft
    • Built 2011

    Last Sold Summary

    • $238/SF
    • 5 Days On Market

    Current Estimated Value $360,180

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

    130 Walnut St, Ridgely, MD 21660
    • 13274 Greensboro Rd, Greensboro, MD 21639
      13274 Greensboro Rd, Greensboro, MD 21639
      13274 Greensboro Rd, Greensboro, MD 21639
      /26

      Est $336,112

      Not Listed For Sale

      13274 Greensboro Rd, Greensboro, MD 21639

      • 3 Beds
      • 2 Baths
      • 1,872 Sq Ft
      • Built 1925
      13274 Greensboro Rd, Greensboro, MD 21639

      Last Sold Summary

      • 18 Days On Market

  • lot 6 Harmony Woods Dr, Preston, MD 21655
    lot 6 Harmony Woods Dr, Preston, MD 21655
    /2

    $79,000

    • Land
    • 2.11 Acres
    • $37,441 per Acre

    lot 6 Harmony Woods Dr, Preston, MD 21655

    Barbara Nichols Results Realty Inc.

    lot 6 Harmony Woods Dr, Preston, MD 21655
  • 4516 Frazier Neck Rd, Preston, MD 21655
    4516 Frazier Neck Rd, Preston, MD 21655
    4516 Frazier Neck Rd, Preston, MD 21655
    /13

    $350,000

    Sold Sep 05, 2025

    4516 Frazier Neck Rd, Preston, MD 21655

    • 2 Beds
    • 1 Bath
    • 1,050 Sq Ft
    • Built 1969

    Last Sold Summary

    • $333/SF
    • 5 Days On Market

    Current Estimated Value $361,512

    Last Listing Agent Benjamin Alder The Land Group

    4516 Frazier Neck Rd, Preston, MD 21655
    • 105 Chamber St, Preston, MD 21655
      105 Chamber St, Preston, MD 21655
      105 Chamber St, Preston, MD 21655
      /6

      Est $270,593

      Not Listed For Sale

      105 Chamber St, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,140 Sq Ft
      • Built 2024
      105 Chamber St, Preston, MD 21655

      Last Sold Summary

  • 162 Main St, Preston, MD 21655
    162 Main St, Preston, MD 21655
    162 Main St, Preston, MD 21655
    /4

    $92,000

    • Land
    • 14,374 Sq Ft
    • $278,788 per Acre

    162 Main St, Preston, MD 21655

    Anne Schmidt Long & Foster Real Estate, Inc.

    162 Main St, Preston, MD 21655
  • 17753 Marvel Rd, Marydel, MD 21649
    17753 Marvel Rd, Marydel, MD 21649
    17753 Marvel Rd, Marydel, MD 21649
    /65

    $550,000

    Sold Jun 02, 2026

    17753 Marvel Rd, Marydel, MD 21649

    • 4 Beds
    • 2.5 Baths
    • 2,475 Sq Ft
    • Built 2021

    Last Sold Summary

    • 4% Below List Price
    • $222/SF
    • 47 Days On Market

    Current Estimated Value $556,990

    Last Listing Agent Vincent Payne Realty Navigator

    17753 Marvel Rd, Marydel, MD 21649
    • 22510 Ash Blvd, Preston, MD 21655
      22510 Ash Blvd, Preston, MD 21655
      22510 Ash Blvd, Preston, MD 21655
      /31

      Not Listed For Sale

      22510 Ash Blvd, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,612 Sq Ft
      • Built 1999
      22510 Ash Blvd, Preston, MD 21655

      Last Sold Summary

      • 4 Days On Market

  • 156 Main St, Preston, MD 21655
    156 Main St, Preston, MD 21655
    156 Main St, Preston, MD 21655
    /18

    $279,900

    • 3 Beds
    • 1.5 Baths
    • 1,694 Sq Ft

    156 Main St, Preston, MD 21655

    Located in the heart of Preston, this classic 1900-built home offers a solid opportunity for both homeowners and investors alike. Inside, the home features 3 bedrooms and1.5 bathrooms and a functional layout that includes a combined laundry room, bath, and mudroom with direct access to the back deck—adding everyday practicality. The kitchen has been updated with durable luxury vinyl plank (LVP)

    Chuck Mangold Benson & Mangold, LLC

    156 Main St, Preston, MD 21655
  • 312 Fountain Ave, Denton, MD 21629
    312 Fountain Ave, Denton, MD 21629
    312 Fountain Ave, Denton, MD 21629
    /38

    $245,000

    Sold Nov 14, 2025

    312 Fountain Ave, Denton, MD 21629

    • 3 Beds
    • 1.5 Baths
    • 1,092 Sq Ft
    • Built 1982

    Last Sold Summary

    • $224/SF
    • 72 Days On Market

    Current Estimated Value $239,037

    Last Listing Agent Pamela Ackermann-Doll RE/MAX Executive

    312 Fountain Ave, Denton, MD 21629
    • 136 Halltown Rd, Marydel, MD 21649
      136 Halltown Rd, Marydel, MD 21649
      136 Halltown Rd, Marydel, MD 21649
      /14

      Est $185,303

      Not Listed For Sale

      136 Halltown Rd, Marydel, MD 21649

      • 3 Beds
      • 1.5 Baths
      • 1,440 Sq Ft
      • Built 1900
      136 Halltown Rd, Marydel, MD 21649

      Last Sold Summary

      • 7 Days On Market

  • 127 Hobbs St, Greensboro, MD 21639
    127 Hobbs St, Greensboro, MD 21639
    127 Hobbs St, Greensboro, MD 21639
    /20

    $272,490

    New Construction $3K PRICE INCREASE Pending
    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft

    127 Hobbs St, Greensboro, MD 21639

    Discover a new home at 127 Hobbs Street in the Kinnamon Meadows community of Greensboro, MD. This home is under construction. This 1,059 square foot open concept cottage-style ranch home offers two bedrooms, two bathrooms, and a two-car driveway. A welcoming front porch leads you into the spacious living room that seamlessly flows into the kitchen, creating a perfect space for entertaining guests

    Justin Wood D.R. Horton Realty of Virginia, LLC

    127 Hobbs St, Greensboro, MD 21639
  • 125 Park Ave, Greensboro, MD 21639
    125 Park Ave, Greensboro, MD 21639
    /2

    $292,990

    Sold Oct 28, 2025

    125 Park Ave, Greensboro, MD 21639

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

    Move in Ready Sold Summary

    • $201/SF
    • 18 Days On Market

    Current Estimated Value $244,088

    D.R. Horton Kinnamon Meadows

    125 Park Ave, Greensboro, MD 21639
    • 3498 Pepper Rd, Federalsburg, MD 21632
      3498 Pepper Rd, Federalsburg, MD 21632
      3498 Pepper Rd, Federalsburg, MD 21632
      /17

      Est $483,192

      Not Listed For Sale

      3498 Pepper Rd, Federalsburg, MD 21632

      • 3 Beds
      • 2 Baths
      • 1,680 Sq Ft
      • Built 1996
      3498 Pepper Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 49 Days On Market

  • 24872 Meeting House Rd, Denton, MD 21629
    24872 Meeting House Rd, Denton, MD 21629
    24872 Meeting House Rd, Denton, MD 21629
    /73

    $175,000

    Pending
    • 3 Beds
    • 1 Bath
    • 1,763 Sq Ft

    24872 Meeting House Rd, Denton, MD 21629

    Own your own vacation home only a short distnce to Ocean City Md. and Rehoboth Beach. The renovation process has been started and you are just in time to choose your own finishes. Have you ever wanted to have your very own AirBNB or vacation home for your family and friends? From here you can walk to the Choptank River where you can fish, enjoy a nice picnic area or you can bring your boat down

    Saad Jamil Samson Properties

    24872 Meeting House Rd, Denton, MD 21629
  • 8197 Detour Rd, Denton, MD 21629
    8197 Detour Rd, Denton, MD 21629
    8197 Detour Rd, Denton, MD 21629
    /77

    $590,000

    Sold Jan 09, 2026

    8197 Detour Rd, Denton, MD 21629

    • 3 Beds
    • 3 Baths
    • 2,565 Sq Ft
    • Built 1989

    Last Sold Summary

    • $230/SF
    • 250 Days On Market

    Current Estimated Value $592,698

    Last Listing Agent Penny Windsor Benson & Mangold, LLC

    8197 Detour Rd, Denton, MD 21629
    • 1211 Painted Fern Rd, Denton, MD 21629
      1211 Painted Fern Rd, Denton, MD 21629
      1211 Painted Fern Rd, Denton, MD 21629
      /14

      Est $407,770

      Not Listed For Sale

      1211 Painted Fern Rd, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 3,238 Sq Ft
      • Built 2006
      1211 Painted Fern Rd, Denton, MD 21629

      Last Sold Summary

      • 19 Days On Market

  • 126 Maple Ave, Preston, MD 21655
    126 Maple Ave, Preston, MD 21655
    126 Maple Ave, Preston, MD 21655
    /23

    $224,000

    $6K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,828 Sq Ft

    126 Maple Ave, Preston, MD 21655

    Step back in time with this early 1900s home. This home is full of character, from the detail in the trim work to the upper level 'porch.' This home offers great potential to be returned to the early 1900s with a little TLC and vision. Located in the heart of Preston, it is 15 minutes from historic Easton with all its amenities. Come take a look and see the vision.

    Marsha Tull Marshy Hope Realty LLC

    126 Maple Ave, Preston, MD 21655
  • 121 Edenton Ln, Denton, MD 21629
    121 Edenton Ln, Denton, MD 21629
    121 Edenton Ln, Denton, MD 21629
    /29

    $299,000

    Sold Mar 05, 2026

    121 Edenton Ln, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1978

    Last Sold Summary

    • $243/SF
    • 98 Days On Market

    Current Estimated Value $297,363

    Last Listing Agent Alicia Gannon Dulin Benson & Mangold, LLC

    121 Edenton Ln, Denton, MD 21629
    • 12041 Crouse Mill Rd, Ridgely, MD 21660
      12041 Crouse Mill Rd, Ridgely, MD 21660
      12041 Crouse Mill Rd, Ridgely, MD 21660
      /42

      Est $387,693

      Not Listed For Sale

      12041 Crouse Mill Rd, Ridgely, MD 21660

      • 3 Beds
      • 2 Baths
      • 1,978 Sq Ft
      • Built 1994
      12041 Crouse Mill Rd, Ridgely, MD 21660

      Last Sold Summary

      • 18 Days On Market

  • 310 Main St, Marydel, MD 21649
    310 Main St, Marydel, MD 21649
    310 Main St, Marydel, MD 21649
    /45

    $529,900

    $100K PRICE DROP
    • Studio
    • 3,600 Sq Ft

    310 Main St, Marydel, MD 21649

    Excellent investment opportunity. Also perfect for a homeowner, live in one unit and let the other units pay your mortgage. 4-unit residential apartments fully rented with long-term tenants. Additional office space available. 5 units total. Current income from 4 units is $5,100/month, potentially $6,100/month including the office. Plenty of parking for tenants, guests, and customers. Updated

    Raphael Szendro R&R Executive Realty

    310 Main St, Marydel, MD 21649
  • 3345 Gallagher Rd, Preston, MD 21655
    3345 Gallagher Rd, Preston, MD 21655
    3345 Gallagher Rd, Preston, MD 21655
    /9

    $370,000

    Sold Dec 23, 2025

    3345 Gallagher Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,312 Sq Ft
    • Built 2025

    Last Sold Summary

    • $282/SF
    • 22 Days On Market

    Current Estimated Value $362,336

    Last Listing Agent Janiece Hines Crown Homes Real Estate

    3345 Gallagher Rd, Preston, MD 21655
    • 28012 Bloomery Rd, Federalsburg, MD 21632
      28012 Bloomery Rd, Federalsburg, MD 21632
      28012 Bloomery Rd, Federalsburg, MD 21632
      /32

      Est $264,930

      Not Listed For Sale

      28012 Bloomery Rd, Federalsburg, MD 21632

      • 3 Beds
      • 1 Bath
      • 1,548 Sq Ft
      • Built 1900
      28012 Bloomery Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 10 Days On Market

  • 25485 Hignutt Rd, Denton, MD 21629
    25485 Hignutt Rd, Denton, MD 21629
    25485 Hignutt Rd, Denton, MD 21629
    /55

    $445,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,720 Sq Ft

    25485 Hignutt Rd, Denton, MD 21629

    Welcome to 25485 Hignutt Rd. in Denton, MD — a completely renovated 3-bedroom, 2.5-bath home situated on nearly a half-acre in a peaceful country setting, while still being just minutes from all the shopping, dining, and conveniences Denton has to offer. This beautifully updated and meticulously maintained home is truly move-in ready. Inside, you'll find durable luxury vinyl plank flooring

    Justin Pokrywka Taylor Properties

    25485 Hignutt Rd, Denton, MD 21629
  • 204 Maple Ave, Greensboro, MD 21639
    204 Maple Ave, Greensboro, MD 21639
    204 Maple Ave, Greensboro, MD 21639
    /16

    $223,000

    Sold May 08, 2026

    204 Maple Ave, Greensboro, MD 21639

    • 3 Beds
    • 1.5 Baths
    • 1,920 Sq Ft
    • Built 1905

    Last Sold Summary

    • 3% Below List Price
    • $116/SF
    • 13 Days On Market

    Current Estimated Value $234,021

    Last Listing Agent Ursula Encarnacion Long & Foster Real Estate, Inc.

    204 Maple Ave, Greensboro, MD 21639
    • 25938 Beauchamp Branch Rd, Denton, MD 21629
      25938 Beauchamp Branch Rd, Denton, MD 21629
      25938 Beauchamp Branch Rd, Denton, MD 21629
      /38

      Est $442,649

      Not Listed For Sale

      25938 Beauchamp Branch Rd, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 2,016 Sq Ft
      • Built 2007
      25938 Beauchamp Branch Rd, Denton, MD 21629

      Last Sold Summary

      • 0 Days On Market

  • 23629 Willow Pond Rd, Denton, MD 21629
    23629 Willow Pond Rd, Denton, MD 21629
    23629 Willow Pond Rd, Denton, MD 21629
    /32

    $450,000

    • 1 Bed
    • 1.5 Baths
    • 1,596 Sq Ft

    23629 Willow Pond Rd, Denton, MD 21629

    A Distinctive Live/Work Opportunity on Marylands Eastern Shore. This prime location tucked away between Easton & Denton, is this remarkable and beautifully maintained, 6.18 acre property that combines the tranquility of a pastoral countryside with the practicality of a live/work lifestyle. Set on 6.18 acres of gently rolling land, this is One Lot, divided into 2 parcels, (one 2 .18 Acre and one 4

    Stephany Barrett Long & Foster Real Estate, Inc.

    23629 Willow Pond Rd, Denton, MD 21629
  • 0 Asbury Dr, Denton, MD 21629
    0 Asbury Dr, Denton, MD 21629
    0 Asbury Dr, Denton, MD 21629
    /24

    $125,000

    Sold Mar 03, 2026

    0 Asbury Dr, Denton, MD 21629

    • Land
    • 3 Acres
    • $41,667 per Acre

    Last Sold Summary

    • 255 Days On Market

    Last Listing Agent Coard Benson Benson & Mangold, LLC

    0 Asbury Dr, Denton, MD 21629
    • 23956 Willow Pond Rd, Denton, MD 21629
      23956 Willow Pond Rd, Denton, MD 21629
      23956 Willow Pond Rd, Denton, MD 21629
      /107

      Est $639,845

      Not Listed For Sale

      23956 Willow Pond Rd, Denton, MD 21629

      • 4 Beds
      • 2 Baths
      • 2,888 Sq Ft
      • Built 1955
      23956 Willow Pond Rd, Denton, MD 21629

      Last Sold Summary

      • 22 Days On Market

  • 0 5 281 Acres Schulyer Rd, Goldsboro, MD 21636
    0 5 281 Acres Schulyer Rd, Goldsboro, MD 21636
    0 5 281 Acres Schulyer Rd, Goldsboro, MD 21636
    /6

    $159,900

    $10K PRICE DROP
    • Land
    • 5.28 Acres
    • $30,284 per Acre

    0 5 281 Acres Schulyer Rd, Goldsboro, MD 21636

    Peaceful 5.281-Acre Wooded Home site with Wildlife Pond Views. Owner Financing Available with an acceptable down payment and terms. Discover the perfect blend of natural beauty and rural tranquility on this 5.281-acre perc-approved building lot, ready for your dream home. Nestled in a quiet country setting, this property offers a stunning overlook of a preserved wildlife pond, where geese, ducks,

    Brett Schrader Taylor Properties

    0 5 281 Acres Schulyer Rd, Goldsboro, MD 21636
  • 26732 Idlewild Rd, Federalsburg, MD 21632
    26732 Idlewild Rd, Federalsburg, MD 21632
    26732 Idlewild Rd, Federalsburg, MD 21632
    /15

    $195,000

    Sold Mar 17, 2026

    26732 Idlewild Rd, Federalsburg, MD 21632

    • 2 Beds
    • 1 Bath
    • 1,040 Sq Ft
    • Built 1966

    Last Sold Summary

    • $188/SF
    • 91 Days On Market

    Current Estimated Value $207,064

    Last Listing Agent Michael Shipley Benson & Mangold, LLC.

    26732 Idlewild Rd, Federalsburg, MD 21632
    • 22700 Thawley Rd, Denton, MD 21629
      22700 Thawley Rd, Denton, MD 21629
      22700 Thawley Rd, Denton, MD 21629
      /24

      Est $433,385

      Not Listed For Sale

      22700 Thawley Rd, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,560 Sq Ft
      • Built 1989
      22700 Thawley Rd, Denton, MD 21629

      Last Sold Summary

      • 3 Days On Market

  • 23547 Jonestown Ln, Preston, MD 21655
    23547 Jonestown Ln, Preston, MD 21655
    23547 Jonestown Ln, Preston, MD 21655
    /3

    $25,000

    • 728 Sq Ft

    23547 Jonestown Ln, Preston, MD 21655

    Build your dream home on this available lot in Preston, Md. Old home on property - either tear down or restore. Buyer to complete due diligence with County

    Dalton Adshead Keller Williams Select Realtors of Cambridge

    23547 Jonestown Ln, Preston, MD 21655
  • 1612 Cattail Commons Way, Denton, MD 21629
    1612 Cattail Commons Way, Denton, MD 21629
    1612 Cattail Commons Way, Denton, MD 21629
    /67

    $385,000

    Sold Dec 31, 2025

    1612 Cattail Commons Way, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,492 Sq Ft
    • Built 2007

    Last Sold Summary

    • $154/SF
    • 77 Days On Market

    Current Estimated Value $387,735

    Last Listing Agent Daniel Register Northrop Realty

    1612 Cattail Commons Way, Denton, MD 21629
    • 24911 Woods Dr, Denton, MD 21629
      24911 Woods Dr, Denton, MD 21629
      24911 Woods Dr, Denton, MD 21629
      /36

      Est $505,655

      Not Listed For Sale

      24911 Woods Dr, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 3,222 Sq Ft
      • Built 1988
      24911 Woods Dr, Denton, MD 21629

      Last Sold Summary

      • 74 Days On Market

  • 115 Boyce Mill Rd, Greensboro, MD 21639
    115 Boyce Mill Rd, Greensboro, MD 21639
    115 Boyce Mill Rd, Greensboro, MD 21639
    /29

    $299,900

    $30K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,350 Sq Ft

    115 Boyce Mill Rd, Greensboro, MD 21639

    Welcome to this charming, Cape-Cod with a Full Unfinished basement—perfectly nestled on a spacious 1/2 Acre! This property gives you that “welcome home” feeling the moment you arrive. Inside, you’ll find a bright and inviting living area featuring a cozy electric fireplace insert and beautiful wood‐beam accents. The freshly renovated kitchen is thoughtfully designed and opens seamlessly to the

    Kathleen Brenton Brenton Realty Group

    115 Boyce Mill Rd, Greensboro, MD 21639
  • 705 S 2nd St, Denton, MD 21629
    705 S 2nd St, Denton, MD 21629
    705 S 2nd St, Denton, MD 21629
    /37

    $250,000

    Sold Jun 08, 2026

    705 S 2nd St, Denton, MD 21629

    • 2 Beds
    • 2 Baths
    • 2,024 Sq Ft
    • Built 1953

    Last Sold Summary

    • $124/SF
    • 5 Days On Market

    Current Estimated Value $324,087

    Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

    705 S 2nd St, Denton, MD 21629

Showing Results 241 - 280, Page 7 of 18

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