15,709

Caroline County, MD Homes

Section Image Section Image
  • /25

    $369,900 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,380 Sq Ft

    23168 Deer Run Ct, Denton, MD 21629

    Tucked away on a quiet street, this well-maintained home offers easy single-level living on a full one-acre lot. With a thoughtful layout, updated finishes, and a peaceful setting, it strikes a great balance between comfort and functionality. Inside, the home features durable LVP flooring throughout and a bright, open feel that flows from the living spaces into the kitchen, complete with

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (410) 709-4607

    23168 Deer Run Ct, Denton, MD 21629
  • /23

    $2,200 Per Month

    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft
    • House for Rent

    102 Sycamore Ln, Greensboro, MD 21639

    Brand New Home in sought after Kinnamon Meadows for lease. This beautiful subdivision is on the edge of town and is waiting for a family to call it home. Large backyard that owner is having graded/seeded. Walk to the nearby park, restaurants or Choptank River. DE beaches only 90 min away. This is a Smart Home and features Smart home touchscreen panel, Smart door lock, Smart Thermostat, Smart

    Agent Photo

    Brenda Fornos

    Taylor Properties

    (410) 429-2833

    102 Sycamore Ln, Greensboro, MD 21639
  • /24

    $160,000 Sold Apr 02, 2026

    315 Cool Spring Rd, Marydel, MD 21649

    • 3 Beds
    • 1.5 Baths
    • 1,524 Sq Ft
    • Built 1920

    Last Sold Summary

    • 5% Below List Price
    • $105/SF
    • 19 Days On Market

    Current Estimated Value $176,607

    Last Listing Agent John Fifer Brokers Realty Group, LLC

    315 Cool Spring Rd, Marydel, MD 21649
    • /28

      Est $228,877 Not Listed For Sale

      125 Riverwalk Terrace, Federalsburg, MD 21632

      • 3 Beds
      • 2.5 Baths
      • 1,365 Sq Ft
      • Built 2024
      125 Riverwalk Terrace, Federalsburg, MD 21632

      Last Sold Summary

      • 4% Above List Price
      • $161/SF
      • 42 Days On Market
      • Last Sold Price $219,990
      • Apr 25, 2025

      Last Listing Agent Kathleen Cassidy DRH Realty Capital, LLC.

  • /102

    $1,250,000

    • 4 Beds
    • 3.5 Baths
    • 3,356 Sq Ft

    23296 Wilder Way, Denton, MD 21629

    Right out of HGTV! Custom Built in 2020, this 3,350+/- sq ft one-level home offers an abundance of amenities including high ceilings, 4 bedrooms, 3.5 Baths, large open floorplan with huge gourmet kitchen with quartz/ss appliances, separate pantry, family room with stacked stone gas fireplace. The Primary Bedroom is located at one end of the house and includes a large bath with double vanity,

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (410) 376-8486

    23296 Wilder Way, Denton, MD 21629
  • /16

    Starting at $465 Per Month

    • 1 - 3 Beds

    101 Quinn Cir, Denton, MD 21629

    Riverwoods at Denton is an affordable housing community featuring newly renovated existing apartments and 36 apartment homes. All of the apartments offer the latest Green energy-saving and conserving features and include a modern kitchen, with abundant cabinetry as well as dishwasher, disposal and microwave. Handicap accessible apartments are also available.Riverwoods at Denton features a 1,500

    Riverwoods at Denton

    (667) 220-5689

    101 Quinn Cir, Denton, MD 21629
  • /5

    $1,020,000 Sold Sep 26, 2025

    0 River Rd Unit MDCM2006210, Ridgely, MD 21660

    • Land
    • 134.85 Acres
    • $7,564 per Acre

    Last Sold Summary

    • 9 Days On Market

    Last Listing Agent Nick Haiduk Thyme Real Estate Co LLC

    0 River Rd Unit MDCM2006210, Ridgely, MD 21660
    • /50

      Est $391,333 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

      • 4% Above List Price
      • $146/SF
      • 7 Days On Market
      • Last Sold Price $375,000
      • May 08, 2025

      Last Listing Agent Kathleen Higginbotham Samson Properties

  • /8

    $125,000

    • Land
    • 2.31 Acres
    • $54,113 per Acre

    0 Burnt Mill Rd Unit MDCM2005294, Ridgely, MD 21660

    Welcome to the Oasis neighborhood, a serene and picturesque enclave nestled in the charming town of Ridgely, MD. This prestigious 2.3-acre wooded lot on Burnt Mill Road presents a unique opportunity to craft your dream home amidst nature's splendor. With its perc approval, this lot is primed and ready for you to bring your architectural vision to life. As you enter the Oasis, you're greeted by a

    Agent Photo

    Gretchen Wichlinski

    Compass

    (667) 282-1883

    0 Burnt Mill Rd Unit MDCM2005294, Ridgely, MD 21660
  • /10

    Starting at $1,165 Per Month

    • 1 - 3 Beds

    502 Sunset Blvd, Ridgely, MD 21660

    Welcome to Sunset Hargraves Ridgely, where newly renovated affordable apartment homes meet the charm of Maryland’s Eastern Shore. Located in the heart of Ridgely, our spacious 1, 2, and 3-bedroom apartments feature brand-new kitchens, energy-efficient appliances, luxury vinyl plank flooring, new windows, and more. Community-wide upgrades include new roofing, gutters, and refreshed breezeways,

    Sunset Hargraves Ridgely

    (410) 634-7485

    502 Sunset Blvd, Ridgely, MD 21660
  • /80

    $710,000 Sold Mar 20, 2026

    15184 Jarrell Rd, Goldsboro, MD 21636

    • 6 Beds
    • 4.5 Baths
    • 5,000 Sq Ft
    • Built 1995

    Last Sold Summary

    • $142/SF
    • 494 Days On Market

    Current Estimated Value $767,207

    Last Listing Agent Leslie Fulford Mann & Sons, Inc.

    15184 Jarrell Rd, Goldsboro, MD 21636
    • /22

      Est $247,479 Not Listed For Sale

      8 N Maple Ave, Ridgely, MD 21660

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1977
      8 N Maple Ave, Ridgely, MD 21660

      Last Sold Summary

      • 10% Above List Price
      • $214/SF
      • 7 Days On Market
      • Last Sold Price $226,000
      • May 07, 2025

      Last Listing Agent Blaine Williamson McClain-Williamson Realty, LLC

  • /9

    $125,000

    • Land
    • 2.54 Acres
    • $49,213 per Acre

    0 Burnt Mill Rd Unit MDCM2005298, Ridgely, MD 21660

    Welcome to the Oasis neighborhood, a serene and picturesque enclave nestled in the charming town of Ridgely, MD. This prestigious 2.5-acre wooded lot on Burnt Mill Road presents a unique opportunity to craft your dream home amidst nature's splendor. With its perc approval, this lot is primed and ready for you to bring your architectural vision to life. As you enter the Oasis, you're greeted by a

    Agent Photo

    Gretchen Wichlinski

    Compass

    (667) 297-6243

    0 Burnt Mill Rd Unit MDCM2005298, Ridgely, MD 21660
  • /2

    Starting at $670 Per Month

    • 1 - 4 Beds

    500 High St, Denton, MD 21629

    Riverview Gardens

    (443) 448-8909

    500 High St, Denton, MD 21629
  • /21

    $391,000 Sold Oct 29, 2025

    11225 Shane Cir, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 2017

    Last Sold Summary

    • $261/SF
    • 4 Days On Market

    Current Estimated Value $394,459

    Last Listing Agent Kathleen Brenton Brenton Realty Group

    11225 Shane Cir, Ridgely, MD 21660
    • /53

      Est $343,973 Not Listed For Sale

      6939 Reliance Rd, Federalsburg, MD 21632

      • 3 Beds
      • 2 Baths
      • 1,560 Sq Ft
      • Built 1981
      6939 Reliance Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 7% Above List Price
      • $205/SF
      • 132 Days On Market
      • Last Sold Price $320,000
      • Apr 28, 2025

      Last Listing Agent Sharon Fisher RE/MAX Advantage Realty

  • /60

    $679,000

    • 3 Beds
    • 2 Baths

    28402 Liden School Rd, Denton, MD 21629

    Private serene living at its finest! This 15.77 acres is included with one-acre parcel with the rancher on it for a total of 16.77 acres according to tax records. This property has it all -- gorgeous rancher with 3 BR and 2 full baths; large walk-in pantry in the kitchen, family room with pellet stove and brick fireplace that can burn wood if buyer desires to do so; two large walk-in closets in

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    (410) 421-7747

    28402 Liden School Rd, Denton, MD 21629
  • /5

    $2,000 Per Month

    • 4 Beds
    • 2 Baths
    • 3,692 Sq Ft
    • House for Rent

    26360 Whiteleysburg Rd, Greensboro, MD 21639

    Property Id: 1799471This 4 bedrooms, 1 3/4 bath home has been remodeled with new carpet, paint, fixtures. It's located close to town with shopping, stores and everything you need. Lawn care, water & sewer are included in the rent! Oil heat and plenty of yard for family gatherings and cook outs. No pets and credit score must be at least 625. To schedule a showing, call or text Chris with

    (667) 220-6658

    26360 Whiteleysburg Rd, Greensboro, MD 21639
  • /24

    $199,000 Sold Jun 05, 2025

    311 S 4th St, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,304 Sq Ft
    • Built 1910

    Last Sold Summary

    • $153/SF
    • 13 Days On Market

    Current Estimated Value $216,096

    Last Listing Agent Kathleen Brenton Brenton Realty Group

    311 S 4th St, Denton, MD 21629
    • /20

      Est $318,137 Not Listed For Sale

      24033 Friendship Rd, Preston, MD 21655

      • 3 Beds
      • 1 Bath
      • 1,120 Sq Ft
      • Built 1976
      24033 Friendship Rd, Preston, MD 21655

      Last Sold Summary

      • 1% Above List Price
      • $281/SF
      • 11 Days On Market
      • Last Sold Price $315,000
      • Apr 30, 2025

      Last Listing Agent Mary Mabry Keller Williams Select Realtors of Cambridge

  • /14

    $124,900

    • Land
    • 10.39 Acres
    • $12,021 per Acre

    PARCEL 91 Cool Spring Rd, Marydel, MD 21649

    Ready for you to build your new home! This beautiful lot is already perc approved for a 4=bedroom home. The woods are a great habitat for deer and turkey and other wildlife. This lovely lot is all ready for the new owner to apply for home construction as the buyer has had the survey completed with the SRA noted on it so lots of the necessary paperwork is completed. So come see and come buy and be

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    (410) 650-6268

    PARCEL 91 Cool Spring Rd, Marydel, MD 21649
  • /8

    $2,200 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft
    • Townhouse for Rent

    113 Riverwalk Terrace, Federalsburg, MD 21632

    Bright and beautifully maintained townhouse in the desirable Riverwalk Terrace community. This like-new home offers modern finishes and a comfortable living space, perfect for tenants seeking quality and convenience. The owner covers HOA fees and the security system for added peace of mind. Tenants are responsible for water, sewer and trash utilities. All applicants must apply through the

    Barbara Blosser Long & Foster Real Estate, Inc.

    113 Riverwalk Terrace, Federalsburg, MD 21632
  • /32

    $227,500 Sold Aug 20, 2025

    1303 Blue Heron Dr, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 1,816 Sq Ft
    • Built 2004

    Last Sold Summary

    • $125/SF
    • 27 Days On Market

    Current Estimated Value $233,241

    Last Listing Agent Justin Pokrywka Taylor Properties

    1303 Blue Heron Dr, Denton, MD 21629
    • /27

      Not Listed For Sale

      112 Riverwalk Terrace, Federalsburg, MD 21632

      • 3 Beds
      • 2.5 Baths
      • 1,365 Sq Ft
      • Built 2024
      112 Riverwalk Terrace, Federalsburg, MD 21632

      Last Sold Summary

      • $154/SF
      • 84 Days On Market
      • Last Sold Price $209,990
      • May 05, 2025

      Last Listing Agent Kathleen Cassidy DRH Realty Capital, LLC.

  • /20

    $215,000

    • 2 Beds
    • 1 Bath
    • 1,371 Sq Ft

    209 Reliance Ave, Federalsburg, MD 21632

    Charming home situated on approximately half an acre, offering a solid foundation and plenty of potential. This property features 2 bedrooms and 1 full bathrooms, along with a spacious bonus room that can serve as a home office, guest space, or additional living area. The home includes a dedicated laundry area and an eat-in kitchen, perfect for casual dining. With “great bones,” this property is

    Agent Photo

    Charlene Spence

    The Spence Realty Group

    (443) 241-6882

    209 Reliance Ave, Federalsburg, MD 21632
  • /10

    $2,000

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • 1,500 Sq Ft
    • House for Rent

    205 Church St, Greensboro, MD 21639

    3 bed, 1 bath single family home. New kitchen and an updated bathroom. Washer and dryer hook-ups.

    205 Church St, Greensboro, MD 21639
  • /7

    $240,000 Sold Aug 29, 2025

    4539 Houston Branch Rd, Federalsburg, MD 21632

    • 2 Beds
    • 1 Bath
    • 736 Sq Ft
    • Built 1949

    Last Sold Summary

    • $326/SF
    • 0 Days On Market

    Current Estimated Value $241,083

    Last Listing Agent Barbara Nichols Results Realty Inc.

    4539 Houston Branch Rd, Federalsburg, MD 21632
    • /23

      Not Listed For Sale

      435 Main St, Goldsboro, MD 21636

      • 2 Beds
      • 1 Bath
      • 1,680 Sq Ft
      • Built 1940
      435 Main St, Goldsboro, MD 21636

      Last Sold Summary

      • $214/SF
      • 16 Days On Market
      • Last Sold Price $360,000
      • May 07, 2025

      Last Listing Agent Elizabeth Tryon Coldwell Banker Realty

  • /8

    $125,000

    • Land
    • 2.4 Acres
    • $52,083 per Acre

    0 Burnt Mill Rd Unit MDCM2005300, Ridgely, MD 21660

    Welcome to the Oasis neighborhood, a serene and picturesque enclave nestled in the charming town of Ridgely, MD. This prestigious 2.4-acre wooded lot on Burnt Mill Road presents a unique opportunity to craft your dream home amidst nature's splendor. With its perc approval, this lot is primed and ready for you to bring your architectural vision to life. As you enter the Oasis, you're greeted by a

    Agent Photo

    Gretchen Wichlinski

    Compass

    (667) 868-0827

    0 Burnt Mill Rd Unit MDCM2005300, Ridgely, MD 21660
  • /10

    $1,150 Per Month

    • 1 Bed
    • 1 Bath
    • 738 Sq Ft
    • House for Rent

    101 W Sunset Ave, Greensboro, MD 21639

    Cute one bedroom apt in the heart of downtown! Upstairs unit has all appliances including washer and dryer. Spacious kitchen with breakfast bar. Open living room to kitchen. Central air. Town water and sewer.

    Marcia Rostien Long & Foster Real Estate, Inc.

    101 W Sunset Ave, Greensboro, MD 21639
  • /38

    $225,000 Sold Sep 19, 2025

    12194 Knife Box Rd, Greensboro, MD 21639

    • 2 Beds
    • 2 Baths
    • 1,488 Sq Ft
    • Built 1900

    Last Sold Summary

    • $151/SF
    • 38 Days On Market

    Current Estimated Value $246,254

    Last Listing Agent Dustin Parker The Parker Group

    12194 Knife Box Rd, Greensboro, MD 21639
    • /26

      Est $502,391 Not Listed For Sale

      11490 Maplewood Dr, Ridgely, MD 21660

      • 4 Beds
      • 3 Baths
      • 2,346 Sq Ft
      • Built 2019
      11490 Maplewood Dr, Ridgely, MD 21660

      Last Sold Summary

      • 12% Above List Price
      • $191/SF
      • 6 Days On Market
      • Last Sold Price $449,000
      • Feb 14, 2025

      Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

  • /20

    $174,500

    • 3 Beds
    • 1 Bath
    • 1,904 Sq Ft

    21948 Main St, Hillsboro, MD 21641

    This home is high on a hill across from the Tuckahoe Creek with some winter views of the water. --the park across the street has a ramp for boats, kayaks, and canoes. The home has 3 bedrooms and a small room for office or nursery or whatever you want it to be; and one full bath -- all upstairs. The front porch entrance opens to a foyer and the living room to the right and then the dining room and

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    (410) 453-1053

    21948 Main St, Hillsboro, MD 21641
  • /16

    $2,350 Per Month

    • 4 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • House for Rent

    6 N Maryland Ave, Ridgely, MD 21660

    Welcome to this stunning New Construction 4-bedroom, 2 full-bath duplex located in Ridgely, MD. Thoughtfully designed and developed by Lomaxx Custom Homes with modern living in mind, this spacious home offers a functional layout, quality finishes, and the convenience. The main level features one bedroom and a full bathroom, perfect for guests, a home office, or flexible living needs. Upstairs,

    6 N Maryland Ave, Ridgely, MD 21660
  • /2

    $380,000 Sold Jan 23, 2026

    0 River Rd Unit MDCM2005824, Ridgely, MD 21660

    • Land
    • 44.74 Acres
    • $8,494 per Acre

    Last Sold Summary

    • 17% Below List Price
    • 203 Days On Market

    Last Listing Agent Andrew Beaven Wright Real Estate

    0 River Rd Unit MDCM2005824, Ridgely, MD 21660
    • /23

      Est $331,978 Not Listed For Sale

      323 Mallard Dr, Greensboro, MD 21639

      • 3 Beds
      • 2.5 Baths
      • 1,632 Sq Ft
      • Built 2023
      323 Mallard Dr, Greensboro, MD 21639

      Last Sold Summary

      • 5% Above List Price
      • $193/SF
      • 10 Days On Market
      • Last Sold Price $315,000
      • Oct 13, 2023

      Last Listing Agent Juliet Wells Coldwell Banker Chesapeake Real Estate Company

  • /63

    $407,500

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft

    7392 Todds Wharf Rd, Preston, MD 21655

    This comfortable rancher with a large above-ground pool with direct access to sunroom and into the home without getting feet dirty (yeah)! Roomy kitchen and open floor plan allows large gatherings to enjoy the roominess. Working wood-burning fireplace is great for use to heat home all winter or just on-call use when you want the ambiance. Convenient mudroom off garage with washer and dryer on

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    (667) 843-7490

    7392 Todds Wharf Rd, Preston, MD 21655
  • /16

    $2,350 Per Month

    • 4 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Townhouse for Rent

    6 N Maryland Ave Unit 6A / 6B, Ridgely, MD 21660

    Welcome to this stunning New Construction 4-bedroom, 2 full-bath duplex located in Ridgely, MD. Thoughtfully designed and developed by Lomaxx Custom Homes with modern living in mind, this spacious home offers a functional layout, quality finishes, and the convenience. The main level features open one bedroom and a full bathroom, perfect for guests, a home office, or flexible living needs. With

    Romont Fletcher Keller Williams Flagship

    6 N Maryland Ave Unit 6A / 6B, Ridgely, MD 21660
  • /19

    $25,000 Sold Nov 24, 2025

    310 Park Ave, Federalsburg, MD 21632

    • 1 Bed
    • 1.5 Baths
    • 812 Sq Ft
    • Built 1904

    Last Sold Summary

    • $31/SF
    • 8 Days On Market

    Current Estimated Value $61,401

    Last Listing Agent Daniel Demers Sell Your Home Services

    310 Park Ave, Federalsburg, MD 21632
    • /30

      Est $316,228 Not Listed For Sale

      319 Mallard Dr, Greensboro, MD 21639

      • 3 Beds
      • 2 Baths
      • 1,468 Sq Ft
      • Built 2023
      319 Mallard Dr, Greensboro, MD 21639

      Last Sold Summary

      • $215/SF
      • 35 Days On Market
      • Last Sold Price $315,000
      • Nov 17, 2023

      Last Listing Agent Juliet Wells Coldwell Banker Chesapeake Real Estate Company

Showing Results 1 - 40, Page 1 of 18

How to Buy a Home How to Finance a Home How to Sell a Home