15,577

Caroline County, MD Homes

Section Image
    • /30

      Est $409,804

      Not Listed For Sale

      1106 Daylily Ln, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 3,096 Sq Ft
      • Built 2007
      1106 Daylily Ln, Denton, MD 21629

      Last Sold Summary

      • 61 Days On Market

      Last Listing Agent Shirley Coulbourne Coldwell Banker Realty

  • /23

    $299,990

    New Construction $5K PRICE INCREASE Pending
    • 3 Beds
    • 2 Baths
    • 1,219 Sq Ft

    119 Hobbs St, Greensboro, MD 21639

    Welcome to 119 Hobbs Street where a move-in ready new home can be yours in Kinnamon Meadows in Greensboro, MD.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 visitors. The open-concept

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

    119 Hobbs St, Greensboro, MD 21639
  • /41

    $325,000

    Sold Feb 27, 2026

    406 Wood Duck Dr, Greensboro, MD 21639

    • 3 Beds
    • 2.5 Baths
    • 1,364 Sq Ft
    • Built 2003

    Last Sold Summary

    • $238/SF
    • 114 Days On Market

    Current Estimated Value $331,452

    Last Listing Agent Brittany Gough Samson Properties

    406 Wood Duck Dr, Greensboro, MD 21639
    • /27

      Est $423,231

      Not Listed For Sale

      5576 Harmony Woods Dr, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,700 Sq Ft
      • Built 2020
      5576 Harmony Woods Dr, Preston, MD 21655

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Amy Betts Coldwell Banker Realty

  • /5

    $130,000

    • Land
    • 8.85 Acres
    • $14,689 per Acre

    15589 Union Rd, Goldsboro, MD 21636

    25309 Golt farm Ln has an old vacant double-wide on it . PLEASE DO NOT GO INSIDE THE FLOORS ARE NOT SAFE TO GO IN.

    Diane Wenk Wright Real Estate

    15589 Union Rd, Goldsboro, MD 21636
  • /41

    $270,000

    Sold Apr 15, 2026

    306 S Main St, Federalsburg, MD 21632

    • 4 Beds
    • 1.5 Baths
    • 2,820 Sq Ft
    • Built 1908

    Last Sold Summary

    • $96/SF
    • 139 Days On Market

    Current Estimated Value $266,476

    Last Listing Agent Mary Mabry Mabry Real Estate LLC

    306 S Main St, Federalsburg, MD 21632
    • /6

      Est $118,067

      Not Listed For Sale

      27105 River Bridge Rd, Henderson, MD 21640

      • Built 1955
      27105 River Bridge Rd, Henderson, MD 21640

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent David Moore Real Broker, LLC

  • /10

    $275,000

    Under Contract
    • 3 Beds
    • 3 Baths
    • 2,128 Sq Ft

    21245 Tanyard Rd, Preston, MD 21655

    Charming Country Living with Room to Make It Your Own! Welcome to 21245 Tanyard Road, a spacious rancher with 3 bedrooms and 2 full baths nestled on a peaceful 0.62-acre lot in Preston. Built in 1987, this single-level home offers a solid foundation and a functional layout, ready for your personal touch and updates.Whether you're looking for a primary residence or an investment opportunity,

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    21245 Tanyard Rd, Preston, MD 21655
  • /27

    $214,990

    Sold Sep 29, 2025

    157 Riverwalk Terrace, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 1,365 Sq Ft
    • Built 2025

    Last Sold Summary

    • $158/SF
    • 26 Days On Market

    Current Estimated Value $220,000

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

    157 Riverwalk Terrace, Federalsburg, MD 21632
    • /32

      Est $410,728

      Not Listed For Sale

      26062 Holly Ln, Greensboro, MD 21639

      • 3 Beds
      • 2 Baths
      • 1,798 Sq Ft
      • Built 2007
      26062 Holly Ln, Greensboro, MD 21639

      Last Sold Summary

      • 89 Days On Market

      Last Listing Agent Norma Coursey Benson & Mangold, LLC

  • /36

    $350,000

    $40K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 936 Sq Ft

    4455 Smithville Rd, Federalsburg, MD 21632

    This charming ranch-style home, built in 2004, offers a cozy retreat on over 11 acres of serene land, adjoining the picturesque Marshyhope Creek with 3800 acres of Idlewild WMA just across the creek. Inside, discover a traditional floor plan featuring three inviting bedrooms and a country-style kitchen perfect for gatherings. Enjoy the warmth of luxury vinyl plank and carpet flooring throughout.

    Nathan Murray RE/MAX Executive

    4455 Smithville Rd, Federalsburg, MD 21632
  • /37

    $349,000

    Sold Aug 28, 2026

    10280 Log Cabin Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,748 Sq Ft
    • Built 1984

    Last Sold Summary

    • 3% Above List Price
    • $200/SF
    • 110 Days On Market

    Current Estimated Value $367,735

    Last Listing Agent Kathleen Brenton Brenton Realty Group

    10280 Log Cabin Rd, Denton, MD 21629
    • /33

      Est $1,032,725

      Not Listed For Sale

      21498 Dover Bridge Rd, Preston, MD 21655

      • 3 Beds
      • 3 Baths
      • 2,748 Sq Ft
      • Built 1954
      21498 Dover Bridge Rd, Preston, MD 21655

      Last Sold Summary

      • 162 Days On Market

      Last Listing Agent SCOTT REAGAN CALLAWAY FARNELL AND MOORE

  • /43

    $424,900

    Pending
    • 3 Beds
    • 1.5 Baths
    • 1,800 Sq Ft

    509 S 2nd St, Denton, MD 21629

    Welcome to one of Denton’s most enchanting hidden retreats — a beautifully restored and thoughtfully updated 1941 Cape Cod tucked among towering trees, lush gardens, and comfortable living spaces in the heart of town.Lovingly renovated while preserving its original charm and architectural character, the main residence offers timeless warmth and understated elegance throughout. Rich hardwood

    Judith Germain Benson & Mangold, LLC

    509 S 2nd St, Denton, MD 21629
  • /33

    $340,000

    Sold Sep 09, 2026

    401 S 2nd St, Denton, MD 21629

    • 3 Beds
    • 1.5 Baths
    • 1,560 Sq Ft
    • Built 1942

    Last Sold Summary

    • 8% Below List Price
    • $218/SF
    • 60 Days On Market

    Current Estimated Value $351,522

    Last Listing Agent Wes Russum Coldwell Banker Chesapeake Real Estate Company

    401 S 2nd St, Denton, MD 21629
    • /52

      Est $378,854

      Not Listed For Sale

      201 Church St, Greensboro, MD 21639

      • 4 Beds
      • 2 Baths
      • 2,559 Sq Ft
      • Built 1910
      201 Church St, Greensboro, MD 21639

      Last Sold Summary

      • 59 Days On Market

      Last Listing Agent Julie Stevenson Shore Living Real Estate

  • /19

    $415,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,408 Sq Ft

    13166 Oakland Rd, Ridgely, MD 21660

    Possibilities! This Caroline County 3-bedroom 2 bath Victorian sitting on almost 4 acres with fencing and plenty of usable buildings in a country setting. Nearby points of interest include Tuckahoe state park with equestrian trails, hiking trails, even a lake to paddle or fish. Gooden Airpark is just down the road along with a few boat ramps to the Choptank River. The property offers several

    BRIAN MORRIS The Land Group

    13166 Oakland Rd, Ridgely, MD 21660
  • /2

    $70,000

    Sold Jan 09, 2026

    22415 Hillsboro Rd, Denton, MD 21629

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft
    • Built 1910

    Last Sold Summary

    • $61/SF
    • 17 Days On Market

    Current Estimated Value $109,265

    Last Listing Agent TAMMY GREEN Samson Properties

    22415 Hillsboro Rd, Denton, MD 21629
    • /37

      Est $791,639

      Not Listed For Sale

      10903 Collinswood Dr, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 4,404 Sq Ft
      • Built 2007
      10903 Collinswood Dr, Denton, MD 21629

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Bruce Hechmer Long & Foster Real Estate, Inc.

  • /8

    $130,000

    • Land
    • 1.01 Acres
    • $128,713 per Acre

    707 W Sunset Ave, Greensboro, MD 21639

    Several individual parcels on Sunset, Cosden and Harold Streets. One parcel has a large 50' x 70' Morton style building, town water is on site and sewer is available. Any interested buyer should perform their own suitable level of due diligence.

    BRIAN MORRIS The Land Group

    707 W Sunset Ave, Greensboro, MD 21639
  • /19

    $200,000

    Sold Mar 27, 2026

    409 Main St, Goldsboro, MD 21636

    • 2 Beds
    • 1.5 Baths
    • 1,252 Sq Ft
    • Built 1955

    Last Sold Summary

    • $160/SF
    • 134 Days On Market

    Current Estimated Value $201,292

    Last Listing Agent Amy Betts Coldwell Banker Realty

    409 Main St, Goldsboro, MD 21636
    • /39

      Est $403,191

      Not Listed For Sale

      1140 Canvasback Ln, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,602 Sq Ft
      • Built 2007
      1140 Canvasback Ln, Denton, MD 21629

      Last Sold Summary

      • 74 Days On Market

      Last Listing Agent Mark Milligan RE/Max Experience

  • /15

    $289,900

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft

    506 Pintail St, Greensboro, MD 21639

    Nearly new ranch style home with large front porch. Three bedrooms and two full baths plus spacious laundry room enhance this home. Large kitchen with center island with stainless appliances and granite countertops are a focal point of this open floor plan. Move in ready and waiting for a new family!

    Bonnie Johnson Keller Williams Realty

    506 Pintail St, Greensboro, MD 21639
  • /2

    $274,990

    Sold Dec 16, 2025

    123 Park Ave, Greensboro, MD 21639

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

    Move in Ready Sold Summary

    • $233/SF
    • 27 Days On Market

    Current Estimated Value $294,243

    D.R. Horton Kinnamon Meadows

    123 Park Ave, Greensboro, MD 21639
    • /45

      Est $239,050

      Not Listed For Sale

      1306 Blue Heron Dr, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 1,620 Sq Ft
      • Built 2004
      1306 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Lawrence Lessin Save 6, Incorporated

  • /75

    $1,150,000

    Under Contract
    • 4,368 Sq Ft

    6354 Statum Rd, Preston, MD 21655

    This wonderful 20 acre property is a horse person’s dream facility. Located in a rural setting, northeast of Preston Maryland. The farm is highlighted by a well-constructed and maintained 75’ x 225’ indoor riding arena, and an 8 stall concrete center aisle horse barn. The barn includes a heated tack room, wash stall with hot water, grooming stall, loft, and overhangs for great ventilation.

    A. John Price Patterson-Schwartz-Middletown

    6354 Statum Rd, Preston, MD 21655
  • /43

    $245,000

    Sold Mar 18, 2026

    511 Bernard Ave, Greensboro, MD 21639

    • 3 Beds
    • 1 Bath
    • 1,385 Sq Ft
    • Built 1950

    Last Sold Summary

    • $177/SF
    • 118 Days On Market

    Current Estimated Value $252,565

    Last Listing Agent Karen Clark Clark & Co Realty, LLC

    511 Bernard Ave, Greensboro, MD 21639
    • /54

      Est $333,181

      Not Listed For Sale

      203 Wood Duck Dr, Greensboro, MD 21639

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 2003
      203 Wood Duck Dr, Greensboro, MD 21639

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Christina Smith Brenton Realty Group

  • /62

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft

    1010 S 2nd St, Denton, MD 21629

    Nestled on the edge of town, 1010 S 2nd Street delivers the convenience of in-town living without in-town taxes. Situated on 1.06 beautifully landscaped acres with mature plantings, this 3-bedroom, 2-bath home offers a spacious feel inside and out. Interior features include hardwood, LVP, and tile flooring, along with a cozy pellet stove fireplace insert for efficient heating, complemented by hot

    Roger Boyce Chesapeake Real Estate Associates, LLC

    1010 S 2nd St, Denton, MD 21629
  • /18

    $300,000

    Sold Nov 20, 2025

    202 Maryland Ave, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2000

    Last Sold Summary

    • $223/SF
    • 123 Days On Market

    Current Estimated Value $302,184

    Last Listing Agent Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    202 Maryland Ave, Ridgely, MD 21660
    • /20

      Est $227,190

      Not Listed For Sale

      322 Maple Ave, Federalsburg, MD 21632

      • 3 Beds
      • 2 Baths
      • 1,812 Sq Ft
      • Built 1958
      322 Maple Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 67 Days On Market

      Last Listing Agent Dale Hunter Bayside Realty

  • /66

    $574,900

    • 4 Beds
    • 3 Baths
    • 2,440 Sq Ft

    24308 Marlyn Dr, Preston, MD 21655

    Beautifully Maintained Home with Private In-Law Suite, Pool & Exceptional Workshop SpaceThis well-maintained property offers outstanding flexibility with a spacious private in-law suite connected to the main home by a bright sunroom with direct access to the deck and backyard. Perfect for multi-generational living, guests, or potential rental income.The main home features an updated

    Kathleen Brenton Brenton Realty Group

    24308 Marlyn Dr, Preston, MD 21655
  • /43

    $500,000

    Sold May 20, 2026

    300 S 1st St, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,616 Sq Ft
    • Built 1996

    Last Sold Summary

    • 20% Below List Price
    • $309/SF
    • 279 Days On Market

    Current Estimated Value $498,662

    Last Listing Agent Kathleen Brenton Brenton Realty Group

    300 S 1st St, Denton, MD 21629
    • /26

      Not Listed For Sale

      12171 River Rd, Ridgely, MD 21660

      • 3 Beds
      • 2 Baths
      • 1,568 Sq Ft
      • Built 1996
      12171 River Rd, Ridgely, MD 21660

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Justin Pokrywka Taylor Properties

  • /46

    $699,000

    • 3 Beds
    • 5 Baths
    • 3,968 Sq Ft

    24634 Pealiquor Rd, Denton, MD 21629

    Tucked away on a private lot, this spacious property offers a combination of privacy and convenience. The main level features LVP flooring, a large updated kitchen with cherry cabinetry and an owner’s suite for easy one-floor living. A breezy screened porch overlooks the peaceful backyard and provides the perfect setting for relaxing or entertaining. Upstairs, you’ll find a generous recreation

    Barbara Watkins Benson & Mangold, LLC

    24634 Pealiquor Rd, Denton, MD 21629
  • /64

    $565,000

    Sold Oct 08, 2025

    6074 Newton Rd, Preston, MD 21655

    • 3 Beds
    • 2.5 Baths
    • 2,060 Sq Ft
    • Built 1993

    Last Sold Summary

    • $274/SF
    • 64 Days On Market

    Current Estimated Value $564,164

    Last Listing Agent James Bent Benson & Mangold, LLC

    6074 Newton Rd, Preston, MD 21655
    • /22

      Est $410,752

      Not Listed For Sale

      24771 Woods Dr, Denton, MD 21629

      • 3 Beds
      • 3 Baths
      • 1,816 Sq Ft
      • Built 1991
      24771 Woods Dr, Denton, MD 21629

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Brian Gearhart Benson & Mangold, LLC

  • /30

    $259,900

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    325 Carter Ave, Denton, MD 21629

    The joy of one level living!! This home is in Move-in ready condition. Nice size 2 Bedroom 1 Full Bath. Level lot with Patio for enetertaining. Conveniently located within town limits. Shop, parks, restuarants, Brewery.Public Boat ramp to the Choptank River less than a mile.

    Kathleen Brenton Brenton Realty Group

    325 Carter Ave, Denton, MD 21629
  • /18

    $250,000

    Sold Oct 14, 2025

    508 W Sunset Ave, Greensboro, MD 21639

    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft
    • Built 1975

    Last Sold Summary

    • $223/SF
    • 8 Days On Market

    Current Estimated Value $254,625

    Last Listing Agent Erene Katris Coldwell Banker Realty

    508 W Sunset Ave, Greensboro, MD 21639
    • /30

      Est $280,138

      Not Listed For Sale

      1622 Blue Heron Dr, Denton, MD 21629

      • 4 Beds
      • 4 Baths
      • 2,244 Sq Ft
      • Built 2006
      1622 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Jason Dey Kevin Dey Realty

Showing Results 361 - 400, Page 10 of 18

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