15,577

Caroline County, MD Homes

Section Image
    • /14

      Est $416,792

      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

      Last Listing Agent Shirley Coulbourne Coldwell Banker Realty

  • /27

    $299,000

    $40K 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

    Lish Gannon Dulin Benson & Mangold, LLC

    208 Oriole Ave, Ridgely, MD 21660
  • /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 $297,633

    Last Listing Agent Lish Gannon Dulin Benson & Mangold, LLC

    121 Edenton Ln, Denton, MD 21629
    • /42

      Est $362,782

      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

      Last Listing Agent Justin Brewer Baltimore Realty, LLC

  • /2

    $84,000

    $5K PRICE INCREASE
    • Land
    • 2.11 Acres
    • $39,810 per Acre

    lot 6 Harmony Woods Dr, Preston, MD 21655

    Barbara Nichols Results Realty Inc.

    lot 6 Harmony Woods Dr, 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 $360,955

    Last Listing Agent Janiece Hines Crown Homes Real Estate

    3345 Gallagher Rd, Preston, MD 21655
    • /38

      Est $450,857

      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

      Last Listing Agent Amy Mullen Iron Valley Real Estate Ocean City

  • /16

    $249,000

    • 2 Beds
    • 1 Bath
    • 908 Sq Ft

    1210 Market St, Denton, MD 21629

    Welcome to 1210 Market Street. Located just minutes from shopping and downtown. This charming bungalow is charming and has been well maintained. Adjoining bedrooms or bedroom and deidcated home office space. Wood accents through the home make it warm and welcoming. Efficient oil heat . All appliances convey. This is the perfect home for starting out, slowing down. More afforable than renting.

    Barbara Dayton Long & Foster Real Estate, Inc.

    1210 Market St, Denton, MD 21629
  • /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 $225,259

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

    204 Maple Ave, Greensboro, MD 21639
    • /107

      Est $677,032

      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

      Last Listing Agent Chris Rosendale CR Realty

  • /15

    $147,000

    • Land
    • 5.62 Acres
    • $26,157 per Acre

    lot 4 River Rd, Greensboro, MD 21639

    Peaceful 5.62 acre wooded lot located on the outskirts of Greensboro. Perc approved for a conventional tile septic system for up to a 4-bedroom home. Discover the perfect blend of natural beauty and rural tranquility on this perc-approved building lot, ready for your dream home. Create your own private nature retreat and enjoy peaceful country living surrounded by nature, all while being within a

    Allie Harris Taylor Properties

    lot 4 River Rd, Greensboro, MD 21639
  • /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
    • /36

      Est $390,250

      Not Listed For Sale

      11145 Branch Ct, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 1999
      11145 Branch Ct, Denton, MD 21629

      Last Sold Summary

      • 82 Days On Market

      Last Listing Agent Sean O'Connor Coldwell Banker Realty

  • /17

    $199,900

    $80K PRICE DROP
    • 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

    Chuck Mangold Benson & Mangold, LLC

    156 Main St, Preston, MD 21655
  • /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 $214,939

    Last Listing Agent Michael Shipley Benson & Mangold, LLC.

    26732 Idlewild Rd, Federalsburg, MD 21632
    • /24

      Est $461,971

      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

      Last Listing Agent Shirley Coulbourne Coldwell Banker Realty

  • /23

    $220,000

    $10K 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
  • /2

    $20,000

    Sold Sep 15, 2026

    0 Charlotte Ave, Federalsburg, MD 21632

    • Land
    • 12,196 Sq Ft
    • $71,429 per Acre

    Last Sold Summary

    • 27% Below List Price
    • 57 Days On Market

    Last Listing Agent Heather Brummell Keller Williams Realty

    0 Charlotte Ave, Federalsburg, MD 21632
    • /36

      Est $519,252

      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

      Last Listing Agent Jacob Ennis Coldwell Banker Realty

  • /2

    $165,000

    • Land
    • 7 Acres
    • $23,571 per Acre

    0 Lot 37 Paradise Ln Unit MDCM2007882, Goldsboro, MD 21636

    Rural wooded 7 acre lot, possible home site or hunting get away, Owner will have property perked at owners expense with acceptable contingent contract. From Greensboro north on route 313 to left on Union Rd to right on Golts Farm Lane, go to end of dirt road, property on right

    Karlton Morris Long & Foster Real Estate, Inc.

    0 Lot 37 Paradise Ln Unit MDCM2007882, Goldsboro, MD 21636
  • /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 $394,345

    Last Listing Agent Daniel Register Northrop Realty

    1612 Cattail Commons Way, Denton, MD 21629
    • /37

      Est $400,873

      Not Listed For Sale

      8614 Andersontown Rd, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 2,300 Sq Ft
      • Built 1880
      8614 Andersontown Rd, Denton, MD 21629

      Last Sold Summary

      • 132 Days On Market

      Last Listing Agent Andrew Beaven Wright Real Estate

  • /39

    $319,000

    • 3 Beds
    • 2 Baths
    • 2,034 Sq Ft

    105 Noble Ave, Preston, MD 21655

    105 Noble Ave is proof that you don't have to sacrifice space to stay within budget! This massive home offers 3 bedrooms, 2 full bathrooms, and an incredibly flexible floor plan to fit your needs.Originally a 4-bedroom 1 bath home, the fourth upstairs bedroom has been converted into two oversized closets. Need another bedroom? The main level features two flex rooms off the dining area that

    Heather Brummell Keller Williams Realty

    105 Noble Ave, Preston, MD 21655
  • /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 $254,860

    Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

    705 S 2nd St, Denton, MD 21629
    • /58

      Est $495,884

      Not Listed For Sale

      4925 Edmondson Creek Rd, Preston, MD 21655

      • 4 Beds
      • 3 Baths
      • 1,988 Sq Ft
      • Built 1981
      4925 Edmondson Creek Rd, Preston, MD 21655

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Thomas Lucks Keller Williams Realty

  • /2

    $39,950

    • Land
    • 10,454 Sq Ft
    • $166,458 per Acre

    0 Brooklyn Ave, Federalsburg, MD 21632

    Unimproved bulding lot . Did you know that there is a Brooklyn in Federalsburg.

    Barton Johnson/not int Marshy Hope Realty LLC

    0 Brooklyn Ave, Federalsburg, MD 21632
  • /39

    $400,000

    Sold Dec 12, 2025

    1208 Painted Fern Rd, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,994 Sq Ft
    • Built 2006

    Last Sold Summary

    • $134/SF
    • 8 Days On Market

    Current Estimated Value $407,114

    Last Listing Agent Janet Powers Berkshire Hathaway Homeservice Homesale Realty

    1208 Painted Fern Rd, Denton, MD 21629
    • /26

      Est $414,146

      Not Listed For Sale

      25698 Caroline St, Greensboro, MD 21639

      • 3 Beds
      • 2 Baths
      • 1,512 Sq Ft
      • Built 2008
      25698 Caroline St, Greensboro, MD 21639

      Last Sold Summary

      • 50 Days On Market

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

  • /55

    $435,000

    $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,720 Sq Ft

    25485 Hignutt Rd, Denton, MD 21629

    SELLER WILL CONSIDER CONTRIBUTING TOWARD THE BUYER’S ALLOWABLE CLOSING COSTS WITH AN ACCEPTABLE OFFER!Welcome to 25485 Hignutt Road—a completely renovated 3-bedroom, 2.5-bath home situated on nearly half an acre in a peaceful country setting, just minutes from Denton’s shopping, dining and everyday conveniences.This truly move-in-ready home offers comfortable one-level living with

    Justin Pokrywka Taylor Properties

    25485 Hignutt Rd, Denton, MD 21629
  • /29

    $209,000

    Sold May 15, 2026

    417 N Academy St, Greensboro, MD 21639

    • 2 Beds
    • 1 Bath
    • 936 Sq Ft
    • Built 1993

    Last Sold Summary

    • 5% Below List Price
    • $223/SF
    • 8 Days On Market

    Current Estimated Value $213,401

    Last Listing Agent Lawrence Doyle Long & Foster Real Estate, Inc.

    417 N Academy St, Greensboro, MD 21639
    • /34

      Est $333,727

      Not Listed For Sale

      8157 Arch Dr, Denton, MD 21629

      • 3 Beds
      • 1 Bath
      • 1,232 Sq Ft
      • Built 1985
      8157 Arch Dr, Denton, MD 21629

      Last Sold Summary

      • 80 Days On Market

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

  • /31

    $450,000

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

    23629 Willow Pond Rd, Denton, MD 21629

    Back on the market!! A Unique 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.Set on 6.18 acres of gently rolling land, this is One Lot, divided into 2 parcels, (one 2 .18 Acre and one 4 acre parcel).The 2.18 acre parcel

    Stephany Barrett Long & Foster Real Estate, Inc.

    23629 Willow Pond Rd, Denton, MD 21629
  • /66

    $470,000

    Sold Dec 30, 2025

    2570 Guard Rd, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 2,400 Sq Ft
    • Built 2020

    Last Sold Summary

    • $196/SF
    • 96 Days On Market

    Current Estimated Value $485,369

    Last Listing Agent Thomas Burdett Keller Williams Realty

    2570 Guard Rd, Federalsburg, MD 21632
    • /24

      Est $253,472

      Not Listed For Sale

      113 N Main St, Greensboro, MD 21639

      • 4 Beds
      • 1.5 Baths
      • 3,540 Sq Ft
      • Built 1926
      113 N Main St, Greensboro, MD 21639

      Last Sold Summary

      • 54 Days On Market

      Last Listing Agent Kathleen Brenton Brenton Realty Group

  • /2

    $308,990

    New Construction Pending
    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft

    107 Hobbs St, Greensboro, MD 21639

    Discover 107 Hobbs Street, a new home under construction in the quaint Kinnamon Meadows community of Greensboro, MD. The Helena is an inviting 1,460 square foot cottage-style ranch home that offers four bedrooms, two bathrooms, and a one-car garage. The long, welcoming foyer of this home allows for the three guest bedrooms and guest bathroom to be separate from the living areas of the

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

    107 Hobbs St, Greensboro, MD 21639
  • /33

    $449,000

    Sold Feb 27, 2026

    282 Tidewater Cir, Preston, MD 21655

    • 4 Beds
    • 2.5 Baths
    • 2,946 Sq Ft
    • Built 2006

    Last Sold Summary

    • $152/SF
    • 14 Days On Market

    Current Estimated Value $453,939

    Last Listing Agent Heather Brummell Keller Williams Realty

    282 Tidewater Cir, Preston, MD 21655
    • /15

      Est $229,220

      Not Listed For Sale

      22818 Marsh Creek Rd, Preston, MD 21655

      • 3 Beds
      • 1 Bath
      • 1,120 Sq Ft
      • Built 1976
      22818 Marsh Creek Rd, Preston, MD 21655

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Wes Russum Coldwell Banker Chesapeake Real Estate Company

  • /26

    $290,000

    • 4 Beds
    • 2 Baths
    • 2,759 Sq Ft

    105 S 5th Ave, Denton, MD 21629

    Step into a charming piece of history with this beautiful Colonial home in the desirable Denton area. Built in 1900, this 2,759-square-foot residence offers the character and craftsmanship of a bygone era while providing the space and conveniences today's buyers desire.From the moment you arrive, the large wrap-around front porch with beautiful wood decking welcomes you home. It's the

    Roger Boyce Chesapeake Real Estate Associates, LLC

    105 S 5th Ave, Denton, MD 21629
  • /19

    $189,900

    Sold Dec 29, 2025

    116 Stonesifer Dr, Greensboro, MD 21639

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft
    • Built 1954

    Last Sold Summary

    • $226/SF
    • 2 Days On Market

    Current Estimated Value $191,757

    Last Listing Agent Brett Schrader Taylor Properties

    116 Stonesifer Dr, Greensboro, MD 21639
    • /43

      Est $343,813

      Not Listed For Sale

      505 Teal Cir, Greensboro, MD 21639

      • 4 Beds
      • 2.5 Baths
      • 1,952 Sq Ft
      • Built 2004
      505 Teal Cir, Greensboro, MD 21639

      Last Sold Summary

      • 20 Days On Market

      Last Listing Agent Jillian Luna Rosendale Realty

Showing Results 241 - 280, Page 7 of 18

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