15,709

Caroline County, MD Homes

Section Image
    • /69

      Est $420,612 Not Listed For Sale

      1130 Osprey Ln, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,644 Sq Ft
      • Built 2005
      1130 Osprey Ln, Denton, MD 21629

      Last Sold Summary

      • 9% Above List Price
      • $146/SF
      • 4 Days On Market
      • Last Sold Price $385,000
      • Aug 02, 2023

      Last Listing Agent Butch Groom Keller Williams Flagship

  • /36

    $225,000 Under Contract

    • 3 Beds
    • 3 Baths
    • 1,678 Sq Ft

    102 S Academy St, Greensboro, MD 21639

    Classic Charm Meets In-Town Living. Enjoy the luxury of space on this generous .34-acre lot, featuring a 3-bedroom home designed for both quiet mornings on the front porch and lively backyard BBQs. Inside, flow seamlessly from the bright & airy living room to the dining area and kitchen. With three full baths, a dedicated laundry room, and a storage-ready basement, the layout is as functional as

    Karen Clark Clark & Co Realty, LLC

    102 S Academy St, Greensboro, MD 21639
  • /38

    $355,000 Sold Jun 06, 2025

    508 Teal Cir, Greensboro, MD 21639

    • 3 Beds
    • 2.5 Baths
    • 1,952 Sq Ft
    • Built 2004

    Last Sold Summary

    • $182/SF
    • 10 Days On Market

    Current Estimated Value $375,400

    Last Listing Agent Karen Clark Clark & Co Realty, LLC

    508 Teal Cir, Greensboro, MD 21639
    • /28

      Est $187,329 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

      • 3% Above List Price
      • $233/SF
      • 25 Days On Market
      • Last Sold Price $182,000
      • Oct 20, 2023

      Last Listing Agent Blaine Williamson McClain-Williamson Realty, LLC

  • /46

    $399,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,424 Sq Ft

    15204 Jarrell Rd, Goldsboro, MD 21636

    There's a feeling you get when you enter a home that is absolutely pristine, thoughtfully and intentionally updated and ready for you to move and settle in tomorrow! It's a feeling of levity...of moving into this space that feels to have been curated just for you! The improvements have been designed with timeless form and function in mind such as: handsome and durable LVP flooring throughout,

    Rachael Altemose Monument Sotheby's International Realty

    15204 Jarrell Rd, Goldsboro, MD 21636
  • /10

    $180,000 Sold Jan 14, 2026

    245 Briarwood Cir, Denton, MD 21629

    • Studio
    • Built 2010

    Last Sold Summary

    • 392 Days On Market

    Current Estimated Value $193,617

    Last Listing Agent Phil Riordan Meredith Fine Properties

    245 Briarwood Cir, Denton, MD 21629
    • /17

      Est $212,255 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

      • $172/SF
      • 2 Days On Market
      • Last Sold Price $212,000
      • Nov 08, 2024

      Last Listing Agent Shirley Coulbourne Coldwell Banker Realty

  • /30

    $299,900

    • 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
  • /4

    $110,000 Sold Dec 15, 2025

    0 Whiteleysburg Rd Unit DEKT2042216, Harrington, DE 19952

    • Land
    • 2 Acres
    • $55,000 per Acre

    Last Sold Summary

    • 1 Day On Market

    Last Listing Agent Amy Torbert Diamond State Cooperative LLC

    0 Whiteleysburg Rd Unit DEKT2042216, Harrington, DE 19952
    • /19

      Est $401,352 Not Listed For Sale

      11458 Reed Cir, Ridgely, MD 21660

      • 3 Beds
      • 2 Baths
      • 1,440 Sq Ft
      • Built 1993
      11458 Reed Cir, Ridgely, MD 21660

      Last Sold Summary

      • 15% Above List Price
      • $243/SF
      • 5 Days On Market
      • Last Sold Price $349,500
      • Feb 02, 2024

      Last Listing Agent Chris Rosendale CR Realty

  • /31

    $424,000

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

    23116 Gilpin Point Rd, Preston, MD 21655

    A perfectly situated, water-oriented, turnkey, rancher with a piece of country is ready for your enjoyment. Produce your own vegetables, flowers or the like in the already established rear garden beds, collect your peaches, pears and other fruits from fruit bearing trees. Start your plants early in an enclosed greenhouse/produce stand. Complete your 4H projects. A second greenhouse area is framed

    Edward Cartwright Benson & Mangold, LLC

    23116 Gilpin Point Rd, Preston, MD 21655
  • /19

    $315,000 Sold Jan 09, 2026

    25607 Garey Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 920 Sq Ft
    • Built 1998

    Last Sold Summary

    • $342/SF
    • 39 Days On Market

    Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

    25607 Garey Rd, Denton, MD 21629
    • /42

      Est $443,273 Not Listed For Sale

      23 Lister Ln, Ridgely, MD 21660

      • 5 Beds
      • 4.5 Baths
      • 3,441 Sq Ft
      • Built 2005
      23 Lister Ln, Ridgely, MD 21660

      Last Sold Summary

      • 5% Above List Price
      • $123/SF
      • 59 Days On Market
      • Last Sold Price $423,000
      • Aug 30, 2024

      Last Listing Agent Diane Donnelly Keller Williams Flagship

  • /44

    $625,000

    • 3 Beds
    • 2 Baths
    • 1,568 Sq Ft

    12104 Holly Rd, Ridgely, MD 21660

    Bring your horses and enjoy beautiful, country living just minutes away from town! Conveniently located with easy access to everything the eastern shore has to offer. New kitchen, new bathrooms, and new floors makes this place truly turn-key. Sitting on just over five acres, there's plenty of room to make this place yours. Two spacious paddocks, small barn including two stalls, tack room, water,

    Keith Hensley Meredith Fine Properties

    12104 Holly Rd, Ridgely, MD 21660
  • /26

    $115,000 Sold Jun 12, 2025

    17690 Melville Rd, Henderson, MD 21640

    • 2 Beds
    • 1 Bath
    • 1,080 Sq Ft
    • Built 1973

    Last Sold Summary

    • $106/SF
    • 119 Days On Market

    Last Listing Agent Erin Anderson Chesapeake Real Estate Associates, LLC

    17690 Melville Rd, Henderson, MD 21640
    • /15

      Est $60,995 Not Listed For Sale

      27515 Anthony Mill Rd, Denton, MD 21629

      27515 Anthony Mill Rd, Denton, MD 21629

      Last Sold Summary

      • 3% Above List Price
      • 14 Days On Market
      • Last Sold Price $59,500
      • Apr 18, 2024

      Last Listing Agent Gretchen Wichlinski Compass

  • /37

    $592,900 Under Contract

    • 4 Beds
    • 5 Baths
    • 3,491 Sq Ft

    24712 Tribbett Cir, Ridgely, MD 21660

    Welcome to 24712 Tribbett Circle — a beautifully appointed 2016-built home set on 2.43 pristine acres in one of Ridgely’s most desirable neighborhoods. This luxurious 4-bedroom, 4-bathroom property seamlessly blends timeless style with modern comfort, offering an exceptional living experience both inside and out. The main level is adorned with rich bamboo flooring, creating a warm and

    Chris Warren Long & Foster Real Estate, Inc.

    24712 Tribbett Cir, Ridgely, MD 21660
  • /16

    $230,000 Sold Jan 30, 2026

    0 Shore Highway-404 Unit MDCM2004050, Denton, MD 21629

    • Land
    • 3.4 Acres
    • $67,647 per Acre

    Last Sold Summary

    • 30% Below List Price
    • 631 Days On Market

    Last Listing Agent Eddie Matthews Benson & Mangold, LLC

    0 Shore Highway-404 Unit MDCM2004050, Denton, MD 21629
    • /15

      Est $346,118 Not Listed For Sale

      304 Kerr Ave, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,808 Sq Ft
      • Built 2005
      304 Kerr Ave, Denton, MD 21629

      Last Sold Summary

      • 5% Above List Price
      • $183/SF
      • 25 Days On Market
      • Last Sold Price $330,000
      • Oct 16, 2024

      Last Listing Agent Linda Moore Long & Foster

  • /44

    $369,000

    • 3 Beds
    • 2 Baths
    • 1,860 Sq Ft

    412 N Main St, Greensboro, MD 21639

    Back Active at NO fault of the Sellers!.....Rare Find! This 3-bedroom, 2-bath renovated rancher offers the perfect blend of space and charm on a sprawling 0.73 acre in-town lot. Spanning over 1,860 sq. ft. of updated living space, you’ll love the openess of the crisp, white kitchen that flows into the cozy light filled living-dining area, the versatile bonus room/office and the

    Karen Clark Clark & Co Realty, LLC

    412 N Main St, Greensboro, MD 21639
  • /108

    $1,200,000 Sold Jan 21, 2026

    14271 Cedar Ln, Greensboro, MD 21639

    • 6 Beds
    • 3 Baths
    • 3,756 Sq Ft
    • Built 1998

    Last Sold Summary

    • $319/SF
    • 245 Days On Market

    Current Estimated Value $1,169,378

    Last Listing Agent Travis Gray Engel & Völkers Annapolis

    14271 Cedar Ln, Greensboro, MD 21639
    • /15

      Est $214,162 Not Listed For Sale

      22081 Dover Bridge Rd, Preston, MD 21655

      • 3 Beds
      • 1 Bath
      • 1,252 Sq Ft
      • Built 1954
      22081 Dover Bridge Rd, Preston, MD 21655

      Last Sold Summary

      • 7% Above List Price
      • $160/SF
      • 25 Days On Market
      • Last Sold Price $200,000
      • Mar 04, 2025

      Last Listing Agent Pamela Price Berkshire Hathaway HomeServices PenFed Realty

  • /2

    $23,000

    • Land
    • 6,098 Sq Ft
    • $164,286 per Acre

    12115 Lincoln St, Ridgely, MD 21660

    Lot in the town of Ridgely, check with the town/county about putting a new house on this lot. There was previously a house on this lot.

    Pamela Geib Long & Foster Real Estate, Inc.

    12115 Lincoln St, Ridgely, MD 21660
  • /2

    $289,990 Sold Sep 25, 2025

    111 Parkland Rd, Greensboro, MD 21639

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

    Last Sold Summary

    • $199/SF
    • 13 Days On Market

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

    111 Parkland Rd, Greensboro, MD 21639
    • /47

      Est $469,152 Not Listed For Sale

      5577 Harmony Woods Dr, Preston, MD 21655

      • 3 Beds
      • 2.5 Baths
      • 2,526 Sq Ft
      • Built 2006
      5577 Harmony Woods Dr, Preston, MD 21655

      Last Sold Summary

      • 2% Above List Price
      • $182/SF
      • 21 Days On Market
      • Last Sold Price $459,000
      • May 24, 2024

      Last Listing Agent Ed Quidas Long & Foster

  • /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 31st. Tenants have expressed interest in renewing and would prefer to stay, providing potential for continued occupancy. Property is well-maintained and conveniently located near local amenities, schools, and major routes.Please allow adequate notice for all

    emily conley Taylor Properties

    105 Lincoln St, Greensboro, MD 21639
  • /74

    $740,000 Sold Jan 20, 2026

    3485 Gallagher Rd, Preston, MD 21655

    • 3 Beds
    • 2.5 Baths
    • 3,326 Sq Ft
    • Built 2003

    Last Sold Summary

    • $222/SF
    • 5 Days On Market

    Current Estimated Value $725,491

    Last Listing Agent Alicia Gannon Dulin Benson & Mangold, LLC

    3485 Gallagher Rd, Preston, MD 21655
    • /70

      Est $517,134 Not Listed For Sale

      23792 Bridgetown Rd, Henderson, MD 21640

      • 3 Beds
      • 3.5 Baths
      • 2,375 Sq Ft
      • Built 1987
      23792 Bridgetown Rd, Henderson, MD 21640

      Last Sold Summary

      • 3% Above List Price
      • $211/SF
      • 6 Days On Market
      • Last Sold Price $500,000
      • Apr 23, 2025

      Last Listing Agent Chris Rosendale CR Realty

  • /18

    $4,250,000

    • 3 Beds
    • 2.5 Baths

    10870 River Rd, Denton, MD 21629

    Productive Caroline County grain farm approximately 340 acres in 4 parcels with 270+/- tillable acres with 200+/- under pivot. Soil has been grid sampled and is well drained. Farm is improved with three large machine sheds, the potentially usable footprint of a pervious milking parlor and a 3 bedroom, 2.5 bath Rancher overlooking the Choptank River. No easements.

    Jim Corson Benson & Mangold, LLC

    10870 River Rd, Denton, MD 21629
  • /52

    $390,000 Sold Oct 23, 2025

    8556 Tuckahoe Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2001

    Last Sold Summary

    • $290/SF
    • 42 Days On Market

    Current Estimated Value $395,071

    Last Listing Agent Kathleen Armiger Coldwell Banker Realty

    8556 Tuckahoe Rd, Denton, MD 21629
    • /46

      Est $346,909 Not Listed For Sale

      109 Sunset Blvd, Preston, MD 21655

      • 3 Beds
      • 1.5 Baths
      • 1,632 Sq Ft
      • Built 1965
      109 Sunset Blvd, Preston, MD 21655

      Last Sold Summary

      • 8% Above List Price
      • $196/SF
      • 3 Days On Market
      • Last Sold Price $320,000
      • May 12, 2023

      Last Listing Agent Josh Rose LAIRD & ASSOCIATES

  • /30

    $309,000

    • 4 Beds
    • 3.5 Baths
    • 2,640 Sq Ft

    1907 Blue Heron Dr, Denton, MD 21629

    Largest townhome in the area and the best deal! Almost 2700 square feet for only $117 a square foot! The biggest bang for your buck in the county! Highly sought after large townhome in the desirable community of Mallard Landing in Denton, featuring almost double the square footage, and a rear deck off of the kitchen. Multi-generational living has a full bedroom and bath, as well as a large family

    Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    1907 Blue Heron Dr, Denton, MD 21629
  • /3

    $80,000 Sold Sep 02, 2025

    26042 Line Rd, Denton, MD 21629

    • 3 Beds
    • 1 Bath
    • 720 Sq Ft
    • Built 1970

    Last Sold Summary

    • $111/SF
    • 9 Days On Market

    Last Listing Agent Bonnie Duley Long & Foster Real Estate, Inc.

    26042 Line Rd, Denton, MD 21629
    • /15

      Est $316,909 Not Listed For Sale

      1311 Fairfield Ct, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 1,360 Sq Ft
      • Built 2003
      1311 Fairfield Ct, Denton, MD 21629

      Last Sold Summary

      • 4% Above List Price
      • $224/SF
      • 6 Days On Market
      • Last Sold Price $304,000
      • Feb 09, 2024

      Last Listing Agent Chad Robertson Compass

  • /30

    $375,000

    • 4 Beds
    • 2 Baths
    • 1,568 Sq Ft

    24383 Robins Creek Rd, Preston, MD 21655

    VERY NICE 3-4 BEDROOM, 2 BATH HOME IN TWO JOHNS WATERFRONT COMMUNITY. BOAT LANDING APPROXIMATELY 1/4 MILE AWAY. LARGE LIVING ROOM, KITCHEN-DINING ROOM COMBO, PANELED WALLS ARE ALL PAINTED, MOSTLY WOOD FLOORS. LARGE DECK AT REAR OF HOUSE. PATIO AREA WITH A NICE FIRE PIT FOR EVENING ENJOYMENT. MORE PICTURES TO COME SOON. ONLY 40 MILES TO WESTERN SHORE, LESS THAN 60 MILES TO THE BEACH

    Ed Quidas Long & Foster Real Estate, Inc.

    24383 Robins Creek Rd, Preston, MD 21655
  • /104

    $478,000 Sold Aug 19, 2025

    13800 Cedar Ln, Greensboro, MD 21639

    • 2 Beds
    • 1 Bath
    • 1,372 Sq Ft
    • Built 1920

    Last Sold Summary

    • $348/SF
    • 10 Days On Market

    Current Estimated Value $485,869

    Last Listing Agent Lona Todd Taylor Properties

    13800 Cedar Ln, Greensboro, MD 21639
    • /30

      Est $225,920 Not Listed For Sale

      1208 Blue Heron Dr, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 1,560 Sq Ft
      • Built 2004
      1208 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 11% Above List Price
      • $131/SF
      • Last Sold Price $204,000
      • May 26, 2023

      Last Listing Agent Judith Germain Benson & Mangold, LLC

  • /12

    $1,300,000

    • Land
    • 92.9 Acres
    • $13,994 per Acre

    0 Liberty Rd, Federalsburg, MD 21632

    90± deeded acres located east of Federalsburg off Liberty Road. The farm is primarily comprised of tillable land with approximately 36± acres under center pivot irrigation. Soils consist primarily of Woodstown, Klej-Galloway complex, and Fallsington sandy loam soils, which are commonly used for grain and row crop production in the area. The property offers approximately one half mile of road

    Benjamin Alder The Land Group

    0 Liberty Rd, Federalsburg, MD 21632
  • /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 $197,219

    Last Listing Agent Timothy Morgan Keller Williams Realty Delmarva

    17990 Henderson Rd, Marydel, MD 21649
    • /62

      Est $713,091 Not Listed For Sale

      23079 Tuckahoe Springs Dr, Denton, MD 21629

      • 3 Beds
      • 4 Baths
      • 3,737 Sq Ft
      • Built 1974
      23079 Tuckahoe Springs Dr, Denton, MD 21629

      Last Sold Summary

      • 10% Above List Price
      • $174/SF
      • 112 Days On Market
      • Last Sold Price $650,000
      • Sep 13, 2024

      Last Listing Agent Melanie Hopkins Coldwell Banker Chesapeake Real Estate Company

Showing Results 521 - 560, Page 14 of 18

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