15,671

Caroline County, MD Homes

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  • 511 Bernard Ave, Greensboro, MD 21639
    511 Bernard Ave, Greensboro, MD 21639
    511 Bernard Ave, Greensboro, MD 21639
    /43

    $245,000

    • 3 Beds
    • 1 Bath
    • 1,385 Sq Ft

    511 Bernard Ave, Greensboro, MD 21639

    Spacious rancher located on a double lot, over one-third of an acre, plenty of room for outdoor activities or potential future expansion. This home features solid construction and has had significant updates in the past 3-4 years, including a new roof, new windows, and a new HVAC system, adding considerable value and reduces the worry about major repairs in the near future. Inside the residence

    Karen Clark Clark & Co Realty, LLC

    511 Bernard Ave, Greensboro, MD 21639
  • 5213A Bethlehem Rd, Preston, MD 21655
    5213A Bethlehem Rd, Preston, MD 21655
    5213A Bethlehem Rd, Preston, MD 21655
    /50

    $875,000 Sold Jul 11, 2025

    5213A Bethlehem Rd, Preston, MD 21655

    • 4 Beds
    • 3.5 Baths
    • 2,993 Sq Ft
    • Built 2014

    Last Sold Summary

    • $292/SF
    • 3 Days On Market

    Current Estimated Value $939,007

    Last Listing Agent Amanda Morgan Brenton Realty Group

    5213A Bethlehem Rd, Preston, MD 21655
    • 202 Caroline Ave, Ridgely, MD 21660
      202 Caroline Ave, Ridgely, MD 21660
      202 Caroline Ave, Ridgely, MD 21660
      /36

      Est $298,427 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,914 Sq Ft

      202 Caroline Ave, Ridgely, MD 21660

      202 Caroline Ave, Ridgely, MD 21660
  • 300 S 1st St, Denton, MD 21629
    300 S 1st St, Denton, MD 21629
    300 S 1st St, Denton, MD 21629
    /47

    $625,000

    • 3 Beds
    • 2 Baths
    • 1,616 Sq Ft

    300 S 1st St, Denton, MD 21629

    Peaceful Living on the Choptank River!!! One level Living! Offering 3 Bed and 1.5 Bath. Home features an open Floor Plan with Large Living Room w/ Gas Burning Stove., Spacious Kitchen with Tons of Storage, Breakfast Bar, and plenty of space for your Table and Chairs! Primary Bedroom facing the Water with Great Waterfront Views. Home also features a paved driveway with 2 door garage and a full

    Kathleen Brenton Brenton Realty Group

    300 S 1st St, Denton, MD 21629
  • 534 N N 6th St, Denton, MD 21629
    534 N N 6th St, Denton, MD 21629
    /2

    $11,000 Sold Jul 02, 2025

    534 N N 6th St, Denton, MD 21629

    • Land
    • 0.51 Acre
    • $21,569 per Acre

    Last Sold Summary

    • 370 Days On Market

    Current Estimated Value $182,000

    Last Listing Agent Heather Brummell Keller Williams Realty

    534 N N 6th St, Denton, MD 21629
    • 10767 Collinswood Dr, Denton, MD 21629
      10767 Collinswood Dr, Denton, MD 21629
      10767 Collinswood Dr, Denton, MD 21629
      /32

      Est $486,531 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,182 Sq Ft

      10767 Collinswood Dr, Denton, MD 21629

      10767 Collinswood Dr, Denton, MD 21629
  • 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
  • 11489 Reed Cir, Ridgely, MD 21660
    11489 Reed Cir, Ridgely, MD 21660
    11489 Reed Cir, Ridgely, MD 21660
    /46

    $439,500 Sold May 21, 2025

    11489 Reed Cir, Ridgely, MD 21660

    • 4 Beds
    • 2.5 Baths
    • 1,923 Sq Ft
    • Built 1995

    Last Sold Summary

    • $229/SF
    • 31 Days On Market

    Current Estimated Value $473,549

    Last Listing Agent Carol Delayo Chaney Homes, LLC

    11489 Reed Cir, Ridgely, MD 21660
    • 110 S 8th St, Denton, MD 21629
      110 S 8th St, Denton, MD 21629
      110 S 8th St, Denton, MD 21629
      /22

      Est $382,409 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 1,654 Sq Ft

      110 S 8th St, Denton, MD 21629

      110 S 8th St, Denton, MD 21629
  • 162 Main St, Preston, MD 21655
    162 Main St, Preston, MD 21655
    162 Main St, Preston, MD 21655
    /4

    $92,000

    • Land
    • 0.33 Acre
    • $278,788 per Acre

    162 Main St, Preston, MD 21655

    Anne Schmidt Long & Foster Real Estate, Inc.

    162 Main St, Preston, MD 21655
  • 207 Caroline Ave, Ridgely, MD 21660
    207 Caroline Ave, Ridgely, MD 21660
    207 Caroline Ave, Ridgely, MD 21660
    /17

    $150,000 Sold Apr 30, 2025

    207 Caroline Ave, Ridgely, MD 21660

    • 3 Beds
    • 1.5 Baths
    • 1,008 Sq Ft
    • Built 1890

    Last Sold Summary

    • $149/SF
    • 6 Days On Market

    Current Estimated Value $167,922

    Last Listing Agent Timothy Caropreso Keller Williams Flagship

    207 Caroline Ave, Ridgely, MD 21660
    • 116 Main St, Preston, MD 21655
      116 Main St, Preston, MD 21655
      116 Main St, Preston, MD 21655
      /20

      Est $283,775 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,185 Sq Ft

      116 Main St, Preston, MD 21655

      116 Main St, Preston, MD 21655
  • 8578 Tuckahoe Rd, Denton, MD 21629
    8578 Tuckahoe Rd, Denton, MD 21629
    8578 Tuckahoe Rd, Denton, MD 21629
    /64

    $425,000

    • 4 Beds
    • 3 Baths
    • 1,680 Sq Ft

    8578 Tuckahoe Rd, Denton, MD 21629

    This property boasts with a 4 bedroom 3 full bathroom cape cod on a 1 acre lot in a beautiful wide open country setting! Fresh paint throughout the entire house, new refrigerator, new oven, new dryer AND new HVAC! All of the hard work has been done! Minutes to Denton or Easton. Move in ready! There is still plenty of time to be in a new home for the holidays!

    Megan Rosendale Rosendale Realty

    8578 Tuckahoe Rd, Denton, MD 21629
  • 8 N Maple Ave, Ridgely, MD 21660
    8 N Maple Ave, Ridgely, MD 21660
    8 N Maple Ave, Ridgely, MD 21660
    /22

    $226,000 Sold May 07, 2025

    8 N Maple Ave, Ridgely, MD 21660

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1977

    Last Sold Summary

    • $214/SF
    • 7 Days On Market

    Current Estimated Value $247,071

    Last Listing Agent Blaine Williamson McClain-Williamson Realty, LLC

    8 N Maple Ave, Ridgely, MD 21660
    • 1606 Cattail Commons Way, Denton, MD 21629
      1606 Cattail Commons Way, Denton, MD 21629
      1606 Cattail Commons Way, Denton, MD 21629
      /30

      Est $406,285 Not Listed For Sale

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

      1606 Cattail Commons Way, Denton, MD 21629

      1606 Cattail Commons Way, Denton, MD 21629
  • 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
  • 15885 Meeks Rd, Goldsboro, MD 21636
    15885 Meeks Rd, Goldsboro, MD 21636
    15885 Meeks Rd, Goldsboro, MD 21636
    /59

    $389,900 Sold Feb 13, 2025

    15885 Meeks Rd, Goldsboro, MD 21636

    • 3 Beds
    • 1.5 Baths
    • 1,744 Sq Ft
    • Built 1900

    Last Sold Summary

    • $224/SF
    • 200 Days On Market

    Current Estimated Value $405,955

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

    15885 Meeks Rd, Goldsboro, MD 21636
    • 1308 Trice Meadows Cir, Denton, MD 21629
      1308 Trice Meadows Cir, Denton, MD 21629
      1308 Trice Meadows Cir, Denton, MD 21629
      /18

      Est $406,582 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,505 Sq Ft

      1308 Trice Meadows Cir, Denton, MD 21629

      1308 Trice Meadows Cir, Denton, MD 21629
  • 245 Briarwood Cir, Denton, MD 21629
    245 Briarwood Cir, Denton, MD 21629
    245 Briarwood Cir, Denton, MD 21629
    /10

    $225,000 Under Contract

    • Land
    • 0.06 Acre
    • $3,750,000 per Acre

    245 Briarwood Cir, Denton, MD 21629

    Hard to Find Great Construction Project waiting for you.Improved 4 adjoining townhouse parcels with concrete slab that needs to be replaced.Beginning of the Sandy Meadows community that is its own block offering privacy outside of crowded downtown for you to Build and sell or rent.Listing shows one lotLots 55, 56, 57 & 58 This is a unique opportunity for small project in a nice

    Phil Riordan Meredith Fine Properties

    245 Briarwood Cir, Denton, MD 21629
  • 25266 Smith Landing Rd, Denton, MD 21629
    25266 Smith Landing Rd, Denton, MD 21629
    25266 Smith Landing Rd, Denton, MD 21629
    /43

    $315,000 Sold Sep 15, 2025

    25266 Smith Landing Rd, Denton, MD 21629

    • 2 Beds
    • 1 Bath
    • 1,256 Sq Ft
    • Built 1953

    Last Sold Summary

    • $251/SF
    • 2 Days On Market

    Last Listing Agent Megan Rosendale Rosendale Realty

    25266 Smith Landing Rd, Denton, MD 21629
    • 23116 Gilpin Point Rd, Preston, MD 21655
      23116 Gilpin Point Rd, Preston, MD 21655
      23116 Gilpin Point Rd, Preston, MD 21655
      /24

      Est $455,024 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,880 Sq Ft

      23116 Gilpin Point Rd, Preston, MD 21655

      23116 Gilpin Point Rd, Preston, MD 21655
  • 1302 Trice Meadows Cir, Denton, MD 21629
    1302 Trice Meadows Cir, Denton, MD 21629
    1302 Trice Meadows Cir, Denton, MD 21629
    /22

    $399,000

    • 3 Beds
    • 2 Baths
    • 2,412 Sq Ft

    1302 Trice Meadows Cir, Denton, MD 21629

    Lovely Raised Rancher consisting of 2,412 square feet of living with the main level having 3 bedrooms, 2 bathrooms, office/den, living room, kitchen and laundry area with a split floor plan of the bedrooms and the owner's suite on the opposite end of house. No worries about parking your vehicles with this nice 2 car attached garage and on street parking. Additionally, the second floor 52x15 bonus

    George Thompson Long & Foster Real Estate, Inc.

    1302 Trice Meadows Cir, Denton, MD 21629
  • 25329 Calvert Dr, Greensboro, MD 21639
    25329 Calvert Dr, Greensboro, MD 21639
    25329 Calvert Dr, Greensboro, MD 21639
    /39

    $355,000 Sold Apr 18, 2025

    25329 Calvert Dr, Greensboro, MD 21639

    • 3 Beds
    • 2.5 Baths
    • 1,688 Sq Ft
    • Built 1990

    Last Sold Summary

    • $210/SF
    • 13 Days On Market

    Current Estimated Value $390,081

    Last Listing Agent Nick Waldner Keller Williams Realty Centre

    25329 Calvert Dr, Greensboro, MD 21639
    • 6 W Liberty St, Ridgely, MD 21660
      6 W Liberty St, Ridgely, MD 21660
      6 W Liberty St, Ridgely, MD 21660
      /27

      Est $409,124 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,184 Sq Ft

      6 W Liberty St, Ridgely, MD 21660

      6 W Liberty St, Ridgely, MD 21660
  • 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
  • 114 Parkland Rd, Greensboro, MD 21639
    114 Parkland Rd, Greensboro, MD 21639
    /2

    $286,990 Sold Sep 24, 2025

    114 Parkland Rd, Greensboro, MD 21639

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

    Last Sold Summary

    • $197/SF
    • 9 Days On Market

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

    114 Parkland Rd, Greensboro, MD 21639
    • 217 Briarwood Cir, Denton, MD 21629
      217 Briarwood Cir, Denton, MD 21629
      217 Briarwood Cir, Denton, MD 21629
      /29

      Est $303,258 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,568 Sq Ft

      217 Briarwood Cir, Denton, MD 21629

      217 Briarwood Cir, Denton, MD 21629
  • 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

    • Land
    • 5.28 Acres
    • $30,284 per Acre

    0 5 281 Acres Schulyer Rd, Goldsboro, MD 21636

    Peaceful 5.281-Acre Wooded Homesite with Wildlife Pond Views. 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, deer, and turkeys are frequent visitors—creating your own private

    Brett Schrader Taylor Properties

    0 5 281 Acres Schulyer Rd, Goldsboro, MD 21636
  • 27030 Stafford Rd, Marydel, MD 21649
    27030 Stafford Rd, Marydel, MD 21649
    27030 Stafford Rd, Marydel, MD 21649
    /12

    $236,000 Sold Apr 10, 2025

    27030 Stafford Rd, Marydel, MD 21649

    • 3 Beds
    • 1 Bath
    • 1,368 Sq Ft
    • Built 1972

    Last Sold Summary

    • $173/SF
    • 352 Days On Market

    Current Estimated Value $261,433

    Last Listing Agent Myisha Walker Long & Foster Real Estate, Inc.

    27030 Stafford Rd, Marydel, MD 21649
    • 10961 Greensboro Rd, Denton, MD 21629
      10961 Greensboro Rd, Denton, MD 21629
      10961 Greensboro Rd, Denton, MD 21629
      /4

      Est $444,227 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,064 Sq Ft

      10961 Greensboro Rd, Denton, MD 21629

      10961 Greensboro Rd, Denton, MD 21629
  • 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
  • 21596 Dover Bridge Rd, Preston, MD 21655
    21596 Dover Bridge Rd, Preston, MD 21655
    /2

    $99,900 Sold Feb 14, 2025

    21596 Dover Bridge Rd, Preston, MD 21655

    • Land
    • 2.13 Acres
    • $46,901 per Acre

    Last Sold Summary

    • 4 Days On Market

    Current Estimated Value $221,506

    Last Listing Agent Liz Kirkland Iron Valley Real Estate of Central PA

    21596 Dover Bridge Rd, Preston, MD 21655
    • 308 Park Ave, Federalsburg, MD 21632
      308 Park Ave, Federalsburg, MD 21632
      308 Park Ave, Federalsburg, MD 21632
      /27

      Est $165,665 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 952 Sq Ft

      308 Park Ave, Federalsburg, MD 21632

      308 Park Ave, Federalsburg, MD 21632
  • 210 Old Line Rd, Goldsboro, MD 21636
    210 Old Line Rd, Goldsboro, MD 21636
    210 Old Line Rd, Goldsboro, MD 21636
    /27

    $349,900

    • 7 Beds
    • 3 Baths
    • 2,729 Sq Ft

    210 Old Line Rd, Goldsboro, MD 21636

    For The Love Of Old Homes!! This big and bold 1900s landmark is bursting with soul and charm. Spanning over 2700+ square feet and boasting 6-7 bedrooms / 3 full baths across three stories, it’s the ultimate setting for grand entertaining or quiet relaxation. From the welcoming foyer to the third-floor retreat, every inch exudes character. It’s move-in ready but invites your creative TLC to truly

    Karen Clark Clark & Co Realty, LLC

    210 Old Line Rd, Goldsboro, MD 21636
  • 123 Bloomingdale Ave, Federalsburg, MD 21632
    123 Bloomingdale Ave, Federalsburg, MD 21632
    123 Bloomingdale Ave, Federalsburg, MD 21632
    /31

    $292,900 Sold May 16, 2025

    123 Bloomingdale Ave, Federalsburg, MD 21632

    • 3 Beds
    • 1.5 Baths
    • 1,584 Sq Ft
    • Built 1900

    Last Sold Summary

    • $185/SF
    • 369 Days On Market

    Current Estimated Value $305,952

    Last Listing Agent Marla Baines Meredith Fine Properties

    123 Bloomingdale Ave, Federalsburg, MD 21632
    • 12141 Greensboro Rd, Greensboro, MD 21639
      12141 Greensboro Rd, Greensboro, MD 21639
      12141 Greensboro Rd, Greensboro, MD 21639
      /3

      Est $490,261 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,296 Sq Ft

      12141 Greensboro Rd, Greensboro, MD 21639

      12141 Greensboro Rd, Greensboro, MD 21639
  • 103 Park Ave Unit 36203273, Greensboro, MD 21639
    103 Park Ave Unit 36203273, Greensboro, MD 21639
    103 Park Ave Unit 36203273, Greensboro, MD 21639
    /22

    $266,990 New Construction

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

    PERRY Plan at Kinnamon Meadows, Greensboro, MD 21639

    The Perry, a 1,059 square foot open concept cottage-style ranch home, offers two bedrooms and two bathrooms. A welcoming front porch leads you into the spacious living room that seamlessly flows into the kitchen, creating a perfect space for entertaining guests or enjoying family time. The well-equipped kitchen is complete with modern cabinetry, stainless steel appliances, a spacious peninsula

    D.R. Horton Builder
    103 Park Ave Unit 36203273, Greensboro, MD 21639
  • 17635 Cool Spring Rd, Marydel, MD 21649
    17635 Cool Spring Rd, Marydel, MD 21649
    17635 Cool Spring Rd, Marydel, MD 21649
    /52

    $320,000 Sold Nov 19, 2025

    17635 Cool Spring Rd, Marydel, MD 21649

    • 3 Beds
    • 2 Baths
    • 1,782 Sq Ft
    • Built 1992

    Last Sold Summary

    • $180/SF
    • 18 Days On Market

    Last Listing Agent Daphne Reeve Keller Williams Flagship

    17635 Cool Spring Rd, Marydel, MD 21649
    • 350 Deep Shore Rd, Denton, MD 21629
      350 Deep Shore Rd, Denton, MD 21629
      350 Deep Shore Rd, Denton, MD 21629
      /22

      Est $274,315 Not Listed For Sale

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

      350 Deep Shore Rd, Denton, MD 21629

      350 Deep Shore Rd, Denton, MD 21629
  • 26606 Idlewild Rd, Federalsburg, MD 21632
    26606 Idlewild Rd, Federalsburg, MD 21632
    26606 Idlewild Rd, Federalsburg, MD 21632
    /24

    $299,900

    • 3 Beds
    • 1.5 Baths
    • 864 Sq Ft

    26606 Idlewild Rd, Federalsburg, MD 21632

    Three Bedroom, 1 and a half bathrooms, located on a quiet county road. This house has been freshly painted inside and outside, new LVP flooring installed throughout the house, all interior doors have been replaced with white six panel doors and new light fixtures in each room. New washer/dryer and refrigerator installed, heat pump is 1 year old, and there is a 22 kw Generac generator as a backup

    Robert Bringman Long & Foster Real Estate, Inc.

    26606 Idlewild Rd, Federalsburg, MD 21632

Showing Results 241 - 280, Page 7 of 18

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