15,624

Caroline County, MD Homes

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  • /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
    • /12

      Est $220,845

      Not Listed For Sale

      206 Bernard Ave, Federalsburg, MD 21632

      • 3 Beds
      • 1.5 Baths
      • 960 Sq Ft
      • Built 2004
      206 Bernard Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Kat Thompson Benson & Mangold, LLC.

  • /60

    $525,000

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

    22005 Main St, Hillsboro, MD 21641

    PLEASE NOTE that the Owner has listened to the current market, Price has been reduced to $525,000. It is a property of beautifully preserved quality on 3⁄4 of an acre in an urban setting. Most unusual! When compared to equivalent historic properties it is now very competitively priced! This fine, brick dwelling originating from the18th c. is situated in Hillsboro on Maryland's peaceful Eastern

    Nancy McGuire Maryland Heritage Properties

    22005 Main St, Hillsboro, MD 21641
  • /3

    $80,000

    Sold Sep 02, 2025

    26042 Line Rd, Denton, MD 21629

    • 3 Beds
    • 1 Bath
    • 720 Sq Ft
    • Built 1970

    Last Sold Summary

    • $111/SF
    • 9 Days On Market

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

    26042 Line Rd, Denton, MD 21629
    • /44

      Est $436,664

      Not Listed For Sale

      18 Lister Ln, Ridgely, MD 21660

      • 4 Beds
      • 2.5 Baths
      • 3,252 Sq Ft
      • Built 2005
      18 Lister Ln, Ridgely, MD 21660

      Last Sold Summary

      • 38 Days On Market

      Last Listing Agent Barbara Blosser Long & Foster Real Estate, Inc.

  • /9

    $79,000

    • Land
    • 3.05 Acres
    • $25,902 per Acre

    10440 Burrsville Branch Rd, Denton, MD 21629

    Rare opportunity to own over 3 acres in a peaceful rural setting just outside of Denton and approximately one mile from the Maryland/Delaware state line. Close to Delaware Beaches and Tax Free Shopping. This partially wooded homesite backs to open farmland, offering privacy and picturesque country views. The property provides an ideal setting for a custom home, subject to the installation of a

    Deborah Callahan Benson & Mangold, LLC

    10440 Burrsville Branch Rd, Denton, MD 21629
  • /104

    $478,000

    Sold Aug 19, 2025

    13800 Cedar Ln, Greensboro, MD 21639

    • 2 Beds
    • 1 Bath
    • 1,372 Sq Ft
    • Built 1920

    Last Sold Summary

    • $348/SF
    • 10 Days On Market

    Current Estimated Value $494,161

    Last Listing Agent Lona Todd Taylor Properties

    13800 Cedar Ln, Greensboro, MD 21639
    • /69

      Est $406,376

      Not Listed For Sale

      1130 Osprey Ln, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,644 Sq Ft
      • Built 2005
      1130 Osprey Ln, Denton, MD 21629

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Butch Groom Keller Williams Flagship

  • /20

    $170,000

    • 2 Beds
    • 1 Bath
    • 744 Sq Ft

    6140 Laurel Grove Rd, Denton, MD 21629

    Escape the noise and reconnect with what matters most. Nestled on a peaceful 1-acre country setting surrounded by mature trees and open skies, this charming cottage offers the perfect opportunity to embrace the simplicity and serenity of tiny home living. Whether you’re searching for a full-time residence, a weekend retreat, or a place to slow down and enjoy nature, this property delivers a

    Andrea Harrington Compass

    6140 Laurel Grove Rd, Denton, MD 21629
  • /24

    $165,000

    Sold Nov 10, 2025

    17990 Henderson Rd, Marydel, MD 21649

    • 1 Bed
    • 1 Bath
    • 1,527 Sq Ft
    • Built 1973

    Last Sold Summary

    • $108/SF
    • 10 Days On Market

    Current Estimated Value $206,602

    Last Listing Agent Timothy Morgan Keller Williams Realty Delmarva

    17990 Henderson Rd, Marydel, MD 21649
    • /28

      Est $184,092

      Not Listed For Sale

      321 S University Ave, Federalsburg, MD 21632

      • 2 Beds
      • 1 Bath
      • 780 Sq Ft
      • Built 1951
      321 S University Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Blaine Williamson McClain-Williamson Realty, LLC

  • /5

    $89,900

    Pending
    • 2 Beds
    • 1 Bath
    • 600 Sq Ft

    305 Old Denton Rd, Federalsburg, MD 21632

    ** BEST AND FINAL OFFERS DUE 6/12/26 AT NOON ** Investor Alert!! This rancher, situated on over half an acre, is packed with value-add potential! With some TLC and the right vision, this property could be transformed into a strong income-producing asset or profitable flip in no time. Whether you’re looking to renovate and rent or resell, the opportunity here is undeniable—especially with a

    Aubrey Campbell Keller Williams Realty Delmarva

    305 Old Denton Rd, Federalsburg, MD 21632
  • /61

    $429,900

    Sold Jan 05, 2026

    26091 Hokum Dr, Greensboro, MD 21639

    • 4 Beds
    • 2.5 Baths
    • 2,248 Sq Ft
    • Built 2004

    Last Sold Summary

    • $191/SF
    • 24 Days On Market

    Current Estimated Value $467,348

    Last Listing Agent Lori Marino Long & Foster Real Estate, Inc.

    26091 Hokum Dr, Greensboro, MD 21639
    • /17

      Est $209,750

      Not Listed For Sale

      526 High St, Denton, MD 21629

      • 2 Beds
      • 1 Bath
      • 1,232 Sq Ft
      • Built 1890
      526 High St, Denton, MD 21629

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Shirley Coulbourne Coldwell Banker Realty

  • /2

    $25,000

    • Land
    • 12,196 Sq Ft
    • $89,286 per Acre

    12087 Wayman St, Ridgely, MD 21660

    Double lot . There are the remains of a house on the property; please leave the remains "as is". Well and septic unknown.

    Bev Langley Coldwell Banker Realty

    12087 Wayman St, Ridgely, MD 21660
  • /43

    $240,000

    Sold May 06, 2026

    207 Bloomingdale Ave, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,684 Sq Ft
    • Built 1953

    Last Sold Summary

    • $143/SF
    • 202 Days On Market

    Current Estimated Value $239,915

    Last Listing Agent Dustin Parker The Parker Group

    207 Bloomingdale Ave, Federalsburg, MD 21632
    • /19

      Est $402,994

      Not Listed For Sale

      11458 Reed Cir, Ridgely, MD 21660

      • 3 Beds
      • 2 Baths
      • 1,440 Sq Ft
      • Built 1993
      11458 Reed Cir, Ridgely, MD 21660

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Chris Rosendale CR Realty

  • /42

    $334,900

    $24K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 1,800 Sq Ft

    222 S 2nd St, Denton, MD 21629

    This is 222 S. 2nd Street, a recently renovated home with historic charm. Original wood flooring, and architectural details such as moldings and antique door knobs highlight the home's history. Though it embraces the past, the house has been updated with all new appliances, new quartz kitchen countertops, newly painted walls and new siding. The house offers something that many two-story homes do

    Kathleen Brenton Brenton Realty Group

    222 S 2nd St, Denton, MD 21629
  • /20

    $265,490

    Sold Feb 06, 2026

    132 Hobbs St, Greensboro, MD 21639

    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $251/SF
    • 17 Days On Market

    D.R. Horton Kinnamon Meadows

    132 Hobbs St, Greensboro, MD 21639
    • /42

      Est $457,126

      Not Listed For Sale

      23 Lister Ln, Ridgely, MD 21660

      • 5 Beds
      • 4.5 Baths
      • 3,441 Sq Ft
      • Built 2005
      23 Lister Ln, Ridgely, MD 21660

      Last Sold Summary

      • 59 Days On Market

      Last Listing Agent Diane Donnelly Keller Williams Flagship

  • /30

    $279,900

    $40K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,791 Sq Ft

    309 N Main St, Greensboro, MD 21639

    This exquisite Colonial-style home, thoughtfully renovated in 2019, seamlessly blends classic charm with modern luxury. Spanning 1,791 square feet, this residence offers a warm and inviting atmosphere, perfect for creating lasting memories. Step inside to discover a beautifully designed interior featuring engineered luxury vinyl plank flooring that exudes elegance and durability. The heart of the

    Eddie Matthews Benson & Mangold, LLC

    309 N Main St, Greensboro, MD 21639
  • /22

    $205,000

    Sold Jun 05, 2026

    610 Lincoln St, Denton, MD 21629

    • 2 Beds
    • 1 Bath
    • 704 Sq Ft
    • Built 1915

    Last Sold Summary

    • 8% Above List Price
    • $291/SF
    • 14 Days On Market

    Current Estimated Value $197,028

    Last Listing Agent Kat Thompson Benson & Mangold, LLC.

    610 Lincoln St, Denton, MD 21629
    • /15

      Est $62,179

      Not Listed For Sale

      27515 Anthony Mill Rd, Denton, MD 21629

      27515 Anthony Mill Rd, Denton, MD 21629

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Gretchen Wichlinski Compass

  • /12

    $200,000

    Coming Soon
    • 2 Beds
    • 1 Bath
    • 1,080 Sq Ft

    6132 Harmony Rd, Preston, MD 21655

    Discover a hidden gem in this charming 2-bedroom, 1-bathroom ranch-style home, built in 1950 and brimming with potential. Nestled on a generous 0.48-acre lot, this property offers ample space for expansion or outdoor enjoyment, making it an ideal investment opportunity for those looking to enhance their portfolio. The detached structure, constructed with durable block materials, presents a solid

    Frank Davis Exit Community Realty

    6132 Harmony Rd, Preston, MD 21655
  • /3

    $27,500

    Sold Dec 04, 2025

    222 Denton Rd, Federalsburg, MD 21632

    • Land
    • 10,018 Sq Ft
    • $119,565 per Acre

    Last Sold Summary

    • 589 Days On Market

    Current Estimated Value $68,407

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

    222 Denton Rd, Federalsburg, MD 21632
    • /15

      Est $358,626

      Not Listed For Sale

      304 Kerr Ave, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,808 Sq Ft
      • Built 2005
      304 Kerr Ave, Denton, MD 21629

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Linda Moore Long & Foster Real Estate, Inc.

  • /20

    $225,000

    • 4 Beds
    • 1 Bath
    • 1,350 Sq Ft

    5258 Preston Rd, Federalsburg, MD 21632

    4 bedrooms 1 bathroom bungalow being sold "AS IS". 16,700 sq. ft. lot with detached garage. Priced to Sell.Updated 200. amp electric service.

    Barton Johnson/not int Marshy Hope Realty LLC

    5258 Preston Rd, Federalsburg, MD 21632
  • /58

    $700,000

    Sold Dec 17, 2025

    25211 Adams Landing Rd, Denton, MD 21629

    • 4 Beds
    • 2 Baths
    • 2,273 Sq Ft
    • Built 1960

    Last Sold Summary

    • $308/SF
    • 12 Days On Market

    Current Estimated Value $698,714

    Last Listing Agent Linda Moore Long & Foster Real Estate, Inc.

    25211 Adams Landing Rd, Denton, MD 21629
    • /34

      Est $398,616

      Not Listed For Sale

      306 Kerr Ave, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,064 Sq Ft
      • Built 2005
      306 Kerr Ave, Denton, MD 21629

      Last Sold Summary

      • 48 Days On Market

      Last Listing Agent Justin Pokrywka Taylor Properties

  • /43

    $359,900

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,860 Sq Ft

    412 N Main St, Greensboro, MD 21639

    Rare Find! This 3-bedroom, 2-bath renovated rancher offers the perfect blend of space and charm on a sprawling 0.73 acre in-town lot. Spanning over 1,860 sq. ft. of updated living space, you’ll love the openess of the crisp, white kitchen that flows into the cozy light filled living-dining area, the versatile bonus room/office and the entertainment-ready basement with a unique custom bar.

    Karen Clark Clark & Co Realty, LLC

    412 N Main St, Greensboro, MD 21639
  • /49

    $390,000

    Sold Feb 13, 2026

    1111 Ruddy Duck Ct, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,670 Sq Ft
    • Built 2006

    Last Sold Summary

    • $146/SF
    • 13 Days On Market

    Current Estimated Value $397,557

    Last Listing Agent Lee Wolff FSBO Broker

    1111 Ruddy Duck Ct, Denton, MD 21629
    • /31

      Est $266,444

      Not Listed For Sale

      123 Bloomingdale Ave, Federalsburg, MD 21632

      • 3 Beds
      • 1.5 Baths
      • 1,584 Sq Ft
      • Built 1900
      123 Bloomingdale Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 369 Days On Market

      Last Listing Agent Marla Baines Meredith Fine Properties

  • /32

    $224,900

    Pending
    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    304 Academy Ave, Denton, MD 21629

    Why rent when you can own for less?? This home has 3 bedrooms and one bath. Eat-in Kitchen, Large Family Room, nicely landscaped and fenced back yard. Off Street parking Newer HVAC, Kitchen with lots of cabinets, Laundry Room with Washer and Dryer and lots of extra space- Public Water and Sewer. Within walking distance to Resaturants, Parks and Shopping. Come Check this Out! Wont Last.

    Kathleen Brenton Brenton Realty Group

    304 Academy Ave, Denton, MD 21629
  • /5

    $238,000

    Sold Sep 24, 2025

    116 Maple Ave, Preston, MD 21655

    • 2 Beds
    • 1.5 Baths
    • 1,458 Sq Ft
    • Built 1915

    Last Sold Summary

    • $163/SF
    • 69 Days On Market

    Current Estimated Value $235,340

    Last Listing Agent Mary Haddaway Benson & Mangold, LLC

    116 Maple Ave, Preston, MD 21655
    • /15

      Est $223,329

      Not Listed For Sale

      22081 Dover Bridge Rd, Preston, MD 21655

      • 3 Beds
      • 1 Bath
      • 1,252 Sq Ft
      • Built 1954
      22081 Dover Bridge Rd, Preston, MD 21655

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Pamela Price Berkshire Hathaway HomeServices PenFed Realty

  • /2

    $215,000

    • 3 Beds
    • 1 Bath
    • 756 Sq Ft

    105 Lincoln St, Greensboro, MD 21639

    Tenant-occupied property offering an excellent investment opportunity with immediate rental income. Current lease in place through July 31st. Tenants have expressed interest in renewing and would prefer to stay, providing potential for continued occupancy. Property is well-maintained and conveniently located near local amenities, schools, and major routes.Please allow adequate notice for all

    emily conley Taylor Properties

    105 Lincoln St, Greensboro, MD 21639
  • /62

    $520,000

    Sold Jul 24, 2026

    8047 Laurel Ln, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,805 Sq Ft
    • Built 2000

    Last Sold Summary

    • $288/SF
    • 2 Days On Market

    Current Estimated Value $511,486

    Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

    8047 Laurel Ln, Denton, MD 21629
    • /52

      Est $504,711

      Not Listed For Sale

      5569 Harmony Woods Dr, Preston, MD 21655

      • 4 Beds
      • 2.5 Baths
      • 2,909 Sq Ft
      • Built 2005
      5569 Harmony Woods Dr, Preston, MD 21655

      Last Sold Summary

      • 185 Days On Market

      Last Listing Agent Erin Anderson Chesapeake Real Estate Associates, LLC

  • /30

    $294,900

    $14K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,640 Sq Ft

    1907 Blue Heron Dr, Denton, MD 21629

    Largest townhome in the area and the best deal! Almost 2700 square feet for only $117 a square foot! The biggest bang for your buck in the county! Highly sought after large townhome in the desirable community of Mallard Landing in Denton, featuring almost double the square footage, and a rear deck off of the kitchen. Multi-generational living has a full bedroom and bath, as well as a large family

    Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    1907 Blue Heron Dr, Denton, MD 21629
  • /15

    $265,000

    Sold Aug 20, 2025

    3181 Gallagher Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 1990

    Last Sold Summary

    • $237/SF
    • 23 Days On Market

    Current Estimated Value $278,113

    Last Listing Agent Andrew Beaven Wright Real Estate

    3181 Gallagher Rd, Preston, MD 21655

Showing Results 521 - 560, Page 14 of 18

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