15,577

Caroline County, MD Homes

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  • /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 ¾ 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

    Nancy McGuire Maryland Heritage Properties

    22005 Main St, Hillsboro, MD 21641
  • /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
    • /25

      Est $271,487

      Not Listed For Sale

      26280 Hobbs Rd, Denton, MD 21629

      • 2 Beds
      • 1.5 Baths
      • 960 Sq Ft
      • Built 1983
      26280 Hobbs Rd, Denton, MD 21629

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Michelle Anderson Coldwell Banker Premier - Seaford

  • /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
  • /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
    • /50

      Est $396,464

      Not Listed For Sale

      1104 Ruddy Duck Ct, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,577 Sq Ft
      • Built 2005
      1104 Ruddy Duck Ct, Denton, MD 21629

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Kathleen Higginbotham Samson Properties

  • /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
  • /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
    • /54

      Est $437,113

      Not Listed For Sale

      23060 Tuckahoe Springs Dr, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 1,820 Sq Ft
      • Built 1977
      23060 Tuckahoe Springs Dr, Denton, MD 21629

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Glenn Hedgecoth Compass

  • /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
  • /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
    • /50

      Est $371,007

      Not Listed For Sale

      315 W Sunset Ave, Greensboro, MD 21639

      • 4 Beds
      • 2.5 Baths
      • 2,416 Sq Ft
      • Built 1880
      315 W Sunset Ave, Greensboro, MD 21639

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Jillian Luna Rosendale Realty

  • /42

    $324,900

    $34K 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

    Kathleen Brenton Brenton Realty Group

    222 S 2nd St, Denton, MD 21629
  • /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
    • /41

      Est $311,796

      Not Listed For Sale

      118 Edenton Ln, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,479 Sq Ft
      • Built 1975
      118 Edenton Ln, Denton, MD 21629

      Last Sold Summary

      • 113 Days On Market

      Last Listing Agent Nishta Gupta Samson Properties

  • /23

    $289,990

    New Construction $15K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,219 Sq Ft

    109 Hobbs St, Greensboro, MD 21639

    Welcome to 109 Hobbs Street where a new home can be yours in Kinnamon Meadows in Greensboro, MD. This home is not currently under construction.The Sullivan is a charming 1,219-square-foot, cottage-style ranch home featuring three bedrooms, two bathrooms, and a one-car garage. Just off the foyer, two spacious guest bedrooms and a shared full bathroom offer comfort and privacy for family or

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

    109 Hobbs St, Greensboro, MD 21639
  • /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
    • /29

      Est $405,635

      Not Listed For Sale

      1107 Canvasback Ln, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,496 Sq Ft
      • Built 2005
      1107 Canvasback Ln, Denton, MD 21629

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Chris Haddaway Chesapeake Real Estate Associates, LLC

  • /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
  • /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
    • /70

      Est $408,902

      Not Listed For Sale

      1110 Osprey Ln, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,650 Sq Ft
      • Built 2005
      1110 Osprey Ln, Denton, MD 21629

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Judith Germain Benson & Mangold, LLC

  • /38

    $289,900

    New Construction $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,936 Sq Ft

    247 Briarwood Cir, Denton, MD 21629

    New Price, Move In Ready & Closing Cost Help! Welcome home to this beautifully designed new construction interior townhome, ideally situated in an established community in the heart of Denton, Maryland. Offering 4 spacious bedrooms, 2.5 baths, and an oversized rear-load garage, this thoughtfully designed home delivers the perfect combination of modern finishes, comfortable living, and everyday

    Michelle DiDonato Island Realty, LLC

    247 Briarwood Cir, Denton, MD 21629
  • /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
    • /43

      Est $496,728

      Not Listed For Sale

      16911 Heritage Hills Ln, Henderson, MD 21640

      • 4 Beds
      • 2.5 Baths
      • 2,428 Sq Ft
      • Built 2006
      16911 Heritage Hills Ln, Henderson, MD 21640

      Last Sold Summary

      • 36 Days On Market

      Last Listing Agent Blake Hoffman Fathom Realty MD, LLC

  • /32

    $175,000

    $25K PRICE DROP
    • 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
  • /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
    • /43

      Est $747,284

      Not Listed For Sale

      23278 Holly Park Dr, Preston, MD 21655

      • 3 Beds
      • 2.5 Baths
      • 1,711 Sq Ft
      • Built 1972
      23278 Holly Park Dr, Preston, MD 21655

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Mary Mabry Mabry Real Estate LLC

  • /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
  • /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
    • /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.

  • /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 31, 2027. The property is well-maintained and conveniently located near local amenities, schools, and major routes.Please allow adequate notice for all showings.

    emily conley Taylor Properties

    105 Lincoln St, Greensboro, MD 21639
  • /2

    $269,950

    Sold Jan 23, 2026

    123 Parkland Rd, Greensboro, MD 21639

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

    Last Sold Summary

    • $228/SF
    • 85 Days On Market

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

    123 Parkland Rd, Greensboro, MD 21639
    • /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.

  • /20

    $265,900

    Pending
    • 3 Beds
    • 2 Baths
    • 1,548 Sq Ft

    106 S University Ave, Federalsburg, MD 21632

    Attention: First time home buyers, looking to Downsize or needing move-in Ready? This home is for you!Well-maintained 3-bedroom, 2-full-bath Rancher offering comfortable one-level living! This inviting home features a Spacious Kitchen and Living room, along with a generously sized primary suite with an ensuite bath and convenient access to the rear yard. Freshly painted and move-in ready.

    Mary Mabry Mabry Real Estate LLC

    106 S University Ave, Federalsburg, MD 21632
  • /7

    $55,000

    Sold Mar 20, 2026

    205 New St, Goldsboro, MD 21636

    • Land
    • 25,264 Sq Ft
    • $94,828 per Acre

    Last Sold Summary

    • 2 Days On Market

    Current Estimated Value $56,127

    Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

    205 New St, Goldsboro, MD 21636
    • /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

  • /34

    $349,000

    $20K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,575 Sq Ft

    215 Apple Ln, Preston, MD 21655

    *Back Up Offers Will Be Considered*Welcome to this beautiful 3-bedroom, 2-bathroom home filled with wonderful updates throughout. As you arrive, you’ll immediately notice the brand-new roof, offering peace of mind for years to come.Step inside to discover a stunning updated kitchen featuring quartz countertops and stainless steel appliances, perfect for both everyday living and

    Amy Endzel Keller Williams Select Realtors of Annapolis

    215 Apple Ln, Preston, MD 21655
  • /12

    $160,000

    Sold Apr 07, 2026

    2578 Hilltop Rd, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,992 Sq Ft
    • Built 1977

    Last Sold Summary

    • $80/SF
    • 4 Days On Market

    Current Estimated Value $211,135

    Last Listing Agent Heather Brummell Keller Williams Realty

    2578 Hilltop Rd, Federalsburg, MD 21632
    • /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

  • /25

    $299,000

    • 3 Beds
    • 2.5 Baths
    • 1,760 Sq Ft

    107 Chamber St, Preston, MD 21655

    This spacious two-story home offers three bedrooms, two-and-a-half bathrooms, and plenty of room to spread out. The main level features a generously sized living room and a large kitchen with ample space for cooking, gathering, and entertaining. Upstairs, you’ll find a spacious primary suite with its own private bathroom, along with two additional bedrooms and a second full bath. Enjoy your

    Heather Brummell Keller Williams Realty

    107 Chamber St, Preston, MD 21655

Showing Results 521 - 560, Page 14 of 18

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