15,709

Caroline County, MD Homes

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  • 129 Hobbs St, Greensboro, MD 21639

    $273,990 Sold Jan 15, 2026

    129 Hobbs St, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 1% Below List Price
    • $232/SF
    • 14 Days On Market

    D.R. Horton Kinnamon Meadows

    129 Hobbs St, Greensboro, MD 21639
    • /25

      Est $268,616 Not Listed For Sale

      26280 Hobbs Rd, Denton, MD 21629

      • 2 Beds
      • 1.5 Baths
      • 960 Sq Ft
      • Built 1983
      26280 Hobbs Rd, Denton, MD 21629

      Last Sold Summary

      • 6% Above List Price
      • $263/SF
      • 6 Days On Market
      • Last Sold Price $252,500
      • Nov 27, 2024

      Last Listing Agent Michelle Anderson Coldwell Banker Premier - Seaford

  • /24

    $239,900 Pending

    • 3 Beds
    • 2 Baths
    • 1,416 Sq Ft

    329 Maple Ave, Federalsburg, MD 21632

    Charming Rancher with Beautiful Upgrades! This well-maintained 3-bedroom, 2-bath home features beautiful hardwood floors, a spacious living room, and an inviting kitchen designed for both everyday living and entertaining. The kitchen boasts quartz countertops and ample workspace, perfect for cooking and gathering.Enjoy the convenience of a separate laundry room plus an additional storage room

    Mary Mabry Keller Williams Select Realtors of Cambridge

    329 Maple Ave, Federalsburg, MD 21632
  • /13

    $235,000 Sold Jul 31, 2025

    513 Vaughn Ave, Greensboro, MD 21639

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft
    • Built 1996

    Last Sold Summary

    • $204/SF
    • 8 Days On Market

    Current Estimated Value $235,392

    Last Listing Agent Chad Muse KD Realty Inc

    513 Vaughn Ave, Greensboro, MD 21639
    • /54

      Est $444,402 Not Listed For Sale

      23060 Tuckahoe Springs Dr, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 1,820 Sq Ft
      • Built 1977
      23060 Tuckahoe Springs Dr, Denton, MD 21629

      Last Sold Summary

      • 10% Above List Price
      • $223/SF
      • 7 Days On Market
      • Last Sold Price $405,000
      • Oct 25, 2023

      Last Listing Agent Glenn Hedgecoth Compass

  • /55

    $419,000 Under Contract

    • 5 Beds
    • 2 Baths
    • 4,060 Sq Ft

    8 W Liberty St, Ridgely, MD 21660

    Welcome to this beautiful updated Custom Built Brick 5-bedroom, 2-bath home nestled on a generous double corner lot in the quaint town of Ridgely. Combining classic charm with modern updates. This property offers comfort and convenience—perfect for growing families or those who love to entertain. Property hightlights include: Updated kitchen featuring brand-new stainless steel appliances, new

    Barbara Blosser Long & Foster Real Estate, Inc.

    8 W Liberty St, Ridgely, MD 21660
  • /59

    $385,000 Sold Nov 07, 2025

    502 N Academy St, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 2,378 Sq Ft
    • Built 1960

    Last Sold Summary

    • $162/SF
    • 105 Days On Market

    Current Estimated Value $382,424

    Last Listing Agent Chris Rosendale CR Realty

    502 N Academy St, Greensboro, MD 21639
    • /50

      Est $345,469 Not Listed For Sale

      315 W Sunset Ave, Greensboro, MD 21639

      • 4 Beds
      • 2.5 Baths
      • 2,416 Sq Ft
      • Built 1880
      315 W Sunset Ave, Greensboro, MD 21639

      Last Sold Summary

      • 1% Below List Price
      • $145/SF
      • 31 Days On Market
      • Last Sold Price $350,000
      • Jul 22, 2024

      Last Listing Agent Jillian Luna Rosendale Realty

  • /11

    $269,900

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    11 9th St, Ridgely, MD 21660

    Step into this well kept 2 bedroom, 1 bath rancher and feel instantly at home. Enjoy your morning coffee or an afternoon barbeque on the back patio with a privacy fenced back yard. Recent updates include vinyl plank flooring (2024), New roof, new refrigerator, new light fixtures and a fully encapsulated crawl space with sump pump - french drain and dehumidifier (2025). All that's needed is your

    Diane Wenk Wright Real Estate

    11 9th St, Ridgely, MD 21660
  • /4

    $200,000 Sold Jun 09, 2025

    0 Rte 313 Rd Unit 1001900376, Federalsburg, MD 21632

    • Land
    • 40.49 Acres
    • $4,939 per Acre

    Last Sold Summary

    • 29% Below List Price
    • 1,412 Days On Market

    Last Listing Agent Barton Johnson/not int Marshy Hope Realty LLC

    0 Rte 313 Rd Unit 1001900376, Federalsburg, MD 21632
    • /44

      Est $420,420 Not Listed For Sale

      1211 Cattail Commons Way, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 3,036 Sq Ft
      • Built 2006
      1211 Cattail Commons Way, Denton, MD 21629

      Last Sold Summary

      • 11% Above List Price
      • $125/SF
      • 16 Days On Market
      • Last Sold Price $380,000
      • Sep 08, 2023

      Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

  • /60

    $533,900 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 3,442 Sq Ft

    5585 Harmony Woods Dr, Preston, MD 21655

    Set on a private, wooded 1.37± acre lot in Harmony Woods, this beautifully maintained home offers a warm, inviting layout with abundant natural light and thoughtful updates throughout. A welcoming front porch leads into the main level with hardwood floors, detailed trim work, and easy flow from the kitchen and breakfast area to the living room with a wood-burning fireplace. Full-view doors open

    Georgi Chauvin Benson & Mangold, LLC

    5585 Harmony Woods Dr, Preston, MD 21655
  • /2

    $90,000 Sold Apr 07, 2026

    103 S Main St, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 2,116 Sq Ft
    • Built 1890

    Last Sold Summary

    • 5% Below List Price
    • $43/SF
    • 18 Days On Market

    Last Listing Agent Valerie Brown Coldwell Banker Realty

    103 S Main St, Federalsburg, MD 21632
    • /41

      Est $323,016 Not Listed For Sale

      118 Edenton Ln, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,479 Sq Ft
      • Built 1975
      118 Edenton Ln, Denton, MD 21629

      Last Sold Summary

      • 8% Above List Price
      • $203/SF
      • 113 Days On Market
      • Last Sold Price $300,000
      • Apr 11, 2025

      Last Listing Agent Nishta Gupta Samson Properties

  • /52

    $314,900 Pending

    • 4 Beds
    • 3 Baths
    • 1,608 Sq Ft

    529 Liberty Rd, Federalsburg, MD 21632

    There's one thing you almost never find at this price point in Caroline County: a full detached living space that's completely finished and ready to use on day one. This one has it.Set on a quiet stretch in Federalsburg, this four-bedroom, three-bath home has been thoroughly updated from top to bottom. Every major system has been replaced within the last ten years. Roof, HVAC, water heater,

    Alex Archer Real Broker, LLC - Annapolis

    529 Liberty Rd, Federalsburg, MD 21632
  • /28

    $240,990 Sold Jun 30, 2025

    151 Riverwalk Terrace, Federalsburg, MD 21632

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

    Last Sold Summary

    • $177/SF
    • 26 Days On Market

    Current Estimated Value $247,163

    Last Listing Agent Kathleen Cassidy D R Horton Realty of Virginia LLC

    151 Riverwalk Terrace, Federalsburg, MD 21632
    • /29

      Est $391,168 Not Listed For Sale

      1107 Canvasback Ln, Denton, MD 21629

      • 4 Beds
      • 2.5 Baths
      • 2,496 Sq Ft
      • Built 2005
      1107 Canvasback Ln, Denton, MD 21629

      Last Sold Summary

      • 1% Above List Price
      • $155/SF
      • 24 Days On Market
      • Last Sold Price $386,000
      • May 24, 2024

      Last Listing Agent Chris Haddaway Chesapeake Real Estate Associates, LLC

  • /31

    $249,900 Pending

    • 3 Beds
    • 1.5 Baths
    • 1,155 Sq Ft

    502 W Sunset Ave, Greensboro, MD 21639

    Renovated & Move-In Ready with Detached 2-Car Garage! Welcome to this beautifully updated 3-bedroom, 1.5-bath home where modern style meets everyday comfort. From the moment you step inside, you’ll notice the fresh, clean feel created by brand-new LVP flooring, recessed lighting, fresh paint throughout, and a completely renovated kitchen and bathroom designed with today’s buyer in mind.The

    Pamela Geib Long & Foster Real Estate, Inc.

    502 W Sunset Ave, Greensboro, MD 21639
  • /5

    $295,000 Sold Jan 30, 2026

    3376 Jefferson Pond Rd, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2025

    Last Sold Summary

    • $219/SF
    • 182 Days On Market

    Last Listing Agent Amy Herr Keller Williams Realty

    3376 Jefferson Pond Rd, Federalsburg, MD 21632
    • /43

      Est $455,871 Not Listed For Sale

      16911 Heritage Hills Ln, Henderson, MD 21640

      • 4 Beds
      • 2.5 Baths
      • 2,428 Sq Ft
      • Built 2006
      16911 Heritage Hills Ln, Henderson, MD 21640

      Last Sold Summary

      • 1% Below List Price
      • $189/SF
      • 36 Days On Market
      • Last Sold Price $460,000
      • Oct 02, 2023

      Last Listing Agent Blake Hoffman Fathom Realty

  • /20

    $299,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,848 Sq Ft

    9532 Corkell Rd, Denton, MD 21629

    If you’ve been searching for the perfect private sanctuary to call home, your opportunity is here. This charming Cape Cod sits on nearly 13 acres surrounded by peaceful farmland, offering unmatched privacy and endless potential. Step inside to an inviting foyer that opens to a spacious living area with a wood stove, an open kitchen and dining space, a dedicated mud/laundry room, and a main‐level

    Amanda Morgan Brenton Realty Group

    9532 Corkell Rd, Denton, MD 21629
  • 113 Parkland Rd, Greensboro, MD 21639

    $269,990 Sold Oct 13, 2025

    113 Parkland Rd, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,219 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $221/SF
    • 19 Days On Market

    D.R. Horton Kinnamon Meadows

    113 Parkland Rd, Greensboro, MD 21639
    • /26

      Est $271,209 Not Listed For Sale

      310 W Central Ave, Federalsburg, MD 21632

      • 3 Beds
      • 2 Baths
      • 1,359 Sq Ft
      • Built 1941
      310 W Central Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 2% Above List Price
      • $196/SF
      • 4 Days On Market
      • Last Sold Price $266,000
      • May 19, 2023

      Last Listing Agent Debbie McQuaid TTR Sotheby's International Realty

  • /28

    $179,900 Pending

    • 2 Beds
    • 1.5 Baths
    • 1,196 Sq Ft

    341 Academy Ave, Denton, MD 21629

    Welcome to Denton! Small town living with all the amenities nearby! Cute townhouse with two bedrooms, one and a half baths with washer/dryer in unit. Nice rear desk with new Trex decking, private parking in the rear. Low maintenance and No HOA. Walk into town for coffee or a meal then walk down to the water along the Choptank River. Boat ramp and kayak/paddle board launch minutes away. Super

    Jason Dey Kevin Dey Realty

    341 Academy Ave, Denton, MD 21629
  • /25

    $260,000 Sold Oct 30, 2025

    1904 Blue Heron Dr, Denton, MD 21629

    • 4 Beds
    • 3.5 Baths
    • 2,640 Sq Ft
    • Built 2007

    Last Sold Summary

    • $98/SF
    • 61 Days On Market

    Current Estimated Value $258,186

    Last Listing Agent Ralph Harvey ListWithFreedom.com

    1904 Blue Heron Dr, Denton, MD 21629
    • /43

      Est $711,634 Not Listed For Sale

      23278 Holly Park Dr, Preston, MD 21655

      • 3 Beds
      • 2.5 Baths
      • 1,711 Sq Ft
      • Built 1972
      23278 Holly Park Dr, Preston, MD 21655

      Last Sold Summary

      • 6% Below List Price
      • $442/SF
      • 35 Days On Market
      • Last Sold Price $756,000
      • Jul 10, 2024

      Last Listing Agent Mary Mabry Keller Williams Select Realtors of Cambridge

  • /39

    $399,500 Under Contract

    • 4 Beds
    • 2.5 Baths
    • 2,730 Sq Ft

    315 Morning Glory Dr, Denton, MD 21629

    From the moment you step inside, this gorgeous Colonial immediately feels like home. Thoughtfully designed with a 5-foot bump-out extension and a highly desirable open floor plan, the layout offers both space and functionality for everyday living and entertaining. The living room is filled with natural light thanks to an added third window, creating a bright and inviting atmosphere that carries

    Crystal Smith RE/MAX Executive

    315 Morning Glory Dr, Denton, MD 21629
  • /13

    $260,000 Sold Aug 13, 2025

    306 Sunrise Ave, Ridgely, MD 21660

    • 4 Beds
    • 2 Baths
    • 1,539 Sq Ft
    • Built 1955

    Last Sold Summary

    • $169/SF
    • 120 Days On Market

    Current Estimated Value $282,708

    Last Listing Agent Wanda Hampton Clark & Co Realty, LLC

    306 Sunrise Ave, Ridgely, MD 21660
    • /12

      Est $207,298 Not Listed For Sale

      206 Bernard Ave, Federalsburg, MD 21632

      • 3 Beds
      • 1.5 Baths
      • 960 Sq Ft
      • Built 2004
      206 Bernard Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 5% Above List Price
      • $206/SF
      • 21 Days On Market
      • Last Sold Price $198,000
      • Jun 10, 2024

      Last Listing Agent Kat Thompson Benson & Mangold, LLC.

  • /93

    $615,000 Under Contract

    • 3 Beds
    • 2.5 Baths
    • 2,968 Sq Ft

    25305 Sandy Point Rd, Greensboro, MD 21639

    Choptank River waterfront at an incredible price! Come tour this beautiful three-story waterfront home on the Choptank just five minutes from downtown Denton and Route 404 and a short ten-minute drive to Greensboro. The main level features an eat-in kitchen, formal dining room, and a living room and sunroom—both offering breathtaking river views. You'll also find a spacious primary suite, an

    Janet Larson Benson & Mangold, LLC

    25305 Sandy Point Rd, Greensboro, MD 21639
  • /18

    $425,000 Sold Jul 23, 2025

    8 N 2nd St, Denton, MD 21629

    • Studio
    • 3,482 Sq Ft
    • Built 1890

    Last Sold Summary

    • $122/SF
    • 78 Days On Market

    Last Listing Agent Andrew Beaven Wright Real Estate

    8 N 2nd St, Denton, MD 21629
    • /45

      Est $387,275 Not Listed For Sale

      202 N Central Ave, Ridgely, MD 21660

      • 3 Beds
      • 4 Baths
      • 2,668 Sq Ft
      • Built 1885
      202 N Central Ave, Ridgely, MD 21660

      Last Sold Summary

      • 1% Below List Price
      • $146/SF
      • 12 Days On Market
      • Last Sold Price $390,000
      • Oct 10, 2023

      Last Listing Agent Chris Rosendale CR Realty

  • /74

    $525,000

    • 3 Beds
    • 3 Baths
    • 3,088 Sq Ft

    22005 Main St, Hillsboro, MD 21641

    PLEASE NOTE that the Owner has listened to the current market, Price has been reduced to $525,000. It is a property of beautifully preserved quality on 3⁄4 of an acre in an urban setting. Most unusual! When compared to equivalent historic properties it is now very competitively priced! This fine, brick dwelling originating from the18th c. is situated in Hillsboro on Maryland's peaceful Eastern

    Nancy McGuire Maryland Heritage Properties

    22005 Main St, Hillsboro, MD 21641
  • /12

    $60,027 Sold Mar 31, 2026

    21269 Dover Bridge Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1996

    Last Sold Summary

    • $45/SF
    • 64 Days On Market

    Last Listing Agent Donna Harrington Coldwell Banker Realty

    21269 Dover Bridge Rd, Preston, MD 21655
    • /44

      Est $433,214 Not Listed For Sale

      18 Lister Ln, Ridgely, MD 21660

      • 4 Beds
      • 2.5 Baths
      • 3,252 Sq Ft
      • Built 2005
      18 Lister Ln, Ridgely, MD 21660

      Last Sold Summary

      • 4% Above List Price
      • $129/SF
      • 38 Days On Market
      • Last Sold Price $417,900
      • May 24, 2024

      Last Listing Agent Barbara Blosser Long & Foster

  • /9

    $89,000

    • Land
    • 3.05 Acres
    • $29,180 per Acre

    10440 Burrsville Branch Rd, Denton, MD 21629

    3+ ACRES PARTLY WOODED AND BACKS TO FARMLAND. NOT LOCATED IN A COMMUNITY AND NO HOA. (PLAT REFLECTS 3.235 +- ACRES, WHILE SDAT REFELCTS 3.05+- ACRES) PROPERTY IS IMPROVED WITH A 2 STORY HOME THAT WAS BUILT IN 1900 . THIS IS A TEAR DOWN OR PERHAPS POSSIBLY A FIXER UPPER. ***** DO NOT ENTER RESIDENCE***** THERE IS ALSO AN EXISTING WELL AND SEPTIC ON THE PROPERTY. HOUSE, WELL AND SEPTIC ARE AS-IS

    Deborah Callahan Benson & Mangold, LLC

    10440 Burrsville Branch Rd, Denton, MD 21629
  • /13

    $230,000 Sold Feb 27, 2026

    1202 Blue Heron Dr, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 1,753 Sq Ft
    • Built 2004

    Last Sold Summary

    • 2% Below List Price
    • $131/SF
    • 46 Days On Market

    Current Estimated Value $235,699

    Last Listing Agent SHANTA PHILLIPS EXP Realty, LLC

    1202 Blue Heron Dr, Denton, MD 21629
    • /15

      Est $343,555 Not Listed For Sale

      23592 Henry Rd, Ridgely, MD 21660

      • 3 Beds
      • 2 Baths
      • 1,452 Sq Ft
      • Built 1920
      23592 Henry Rd, Ridgely, MD 21660

      Last Sold Summary

      • 11% Above List Price
      • $213/SF
      • 44 Days On Market
      • Last Sold Price $310,000
      • May 12, 2023

      Last Listing Agent Pamela Geib Long & Foster

  • /39

    $425,000 Under Contract

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

    25095 Trunk Line Rd, Henderson, MD 21640

    **Under contract with a home sale contingency. Seller is continuing to show the property and is accepting backup offers.**Welcome to your private retreat on 4.11 acres, offering the perfect blend of updated living and outdoor lifestyle. This secluded property features established trails, abundant wildlife including deer and turkey, and existing hunting stands already in place. Inside, the

    Heather Branham The Parker Group

    25095 Trunk Line Rd, Henderson, MD 21640
  • /16

    $215,000 Sold Oct 24, 2025

    522 Lincoln St, Denton, MD 21629

    • 2 Beds
    • 1 Bath
    • 640 Sq Ft
    • Built 1961

    Last Sold Summary

    • $336/SF
    • 10 Days On Market

    Current Estimated Value $216,265

    Last Listing Agent Amanda Morgan Brenton Realty Group

    522 Lincoln St, Denton, MD 21629

Showing Results 481 - 520, Page 13 of 18

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