15,625

Caroline County, MD Homes

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  • /4

    $1,200,000

    $400K PRICE DROP
    • Land
    • 11 Acres
    • $109,091 per Acre

    0 Liberty (Rifkin Village) Rd Unit MDCM2007390, Federalsburg, MD 21632

    Ready for Development! 43 lots within the Town limits of Federalsburg, Maryland. Total lot space as currently platted is 478,596 sq ft or 11 acres, according to public records. Total property area including the unbuilt road space is roughly 13 acres. Right-of-ways to the property are currently platted from Liberty Rd, Bernard Ave, and the Federalsburg Bypass. 855 ft of frontage on the

    Aaron Dixon Berkshire Hathaway HomeServices PenFed Realty

    0 Liberty (Rifkin Village) Rd Unit MDCM2007390, Federalsburg, MD 21632
  • /2

    $53,000

    Sold Mar 16, 2026

    307 Buena Vista Ave, Federalsburg, MD 21632

    • Land
    • 1.75 Acres
    • $30,286 per Acre

    Last Sold Summary

    • 18% Below List Price
    • 18 Days On Market

    Current Estimated Value $53,444

    Last Listing Agent Heather Brummell Keller Williams Realty

    307 Buena Vista Ave, Federalsburg, MD 21632
    • /7

      Est $222,889

      Not Listed For Sale

      3477 Holland Dr, Federalsburg, MD 21632

      • 3 Beds
      • 1 Bath
      • 1,164 Sq Ft
      • Built 1994
      3477 Holland Dr, Federalsburg, MD 21632

      Last Sold Summary

      • 150 Days On Market

      Last Listing Agent KL Harris Keller Williams Select Realtors of Cambridge

  • /6

    $955,000

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 2,714 Sq Ft

    8851 New Bridge Rd, Denton, MD 21629

    Private Waterfront Retreat on the Choptank RiverExperience the best of Eastern Shore waterfront living in this exceptional home built in 2021, where modern luxury, privacy, and serene views come together on one remarkable property. Situated on 8.15± private acres with approximately 600 feet of Choptank River frontage and deep water access, this stunning retreat offers the perfect balance of

    Shawn Moore Meredith Fine Properties

    8851 New Bridge Rd, Denton, MD 21629
  • /42

    $465,000

    Sold Mar 30, 2026

    24749 Woods Dr, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,550 Sq Ft
    • Built 2000

    Last Sold Summary

    • 4% Below List Price
    • $182/SF
    • 80 Days On Market

    Current Estimated Value $463,990

    Last Listing Agent Peter Stark Benson & Mangold, LLC

    24749 Woods Dr, Denton, MD 21629
    • /12

      Est $217,634

      Not Listed For Sale

      627 Camp Rd, Denton, MD 21629

      • 2 Beds
      • 1 Bath
      • 816 Sq Ft
      • Built 1955
      627 Camp Rd, Denton, MD 21629

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Linda Moore Long & Foster Real Estate, Inc.

  • /27

    $225,000

    $25K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,311 Sq Ft

    25910 Fox Grape Rd, Greensboro, MD 21639

    Quiet living in Fox Grape Farms. Whether you are downsizing or just starting out, this home offers one-level living with 3 bedrooms, 2 full baths and an open living room that flows into the dining area. Situated on a 0.60 +/- parcel, the property also features two (2) storage sheds. Located approximately 7 miles from Denton, MD, 11 miles from Tuckahoe State Park and 16 miles from the Harrington

    John Fifer Brokers Realty Group, LLC

    25910 Fox Grape Rd, Greensboro, MD 21639
  • /30

    $289,000

    Sold Jun 30, 2026

    14185 Drapers Mill Rd, Greensboro, MD 21639

    • 4 Beds
    • 1 Bath
    • 1,352 Sq Ft
    • Built 1910

    Last Sold Summary

    • 3% Below List Price
    • $214/SF
    • 56 Days On Market

    Current Estimated Value $284,002

    Last Listing Agent John Lyons Crown Homes Real Estate

    14185 Drapers Mill Rd, Greensboro, MD 21639
    • /77

      Est $504,160

      Not Listed For Sale

      22959 Lyn Oaks Dr, Preston, MD 21655

      • 3 Beds
      • 2 Baths
      • 1,904 Sq Ft
      • Built 2005
      22959 Lyn Oaks Dr, Preston, MD 21655

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Debbie Lipscomb Benson & Mangold, LLC

  • /55

    $340,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    306 Caroline Ave, Ridgely, MD 21660

    Charming updated Farmhouse style home with hardwood floors throughout and tiled bathrooms. The open kitchen features quartz countertops, a center island for extra prep space and casual dining, stainless steel appliances, and a tile backsplash. The first floor includes a full bath with a tiled walk-in stall shower, plus a separate laundry/mud room. Dual-zone heating and air for year-round comfort.

    Roger Boyce Chesapeake Real Estate Associates, LLC

    306 Caroline Ave, Ridgely, MD 21660
  • /26

    $110,000

    Sold Sep 15, 2025

    201 Denton Rd, Federalsburg, MD 21632

    • 3 Beds
    • 1 Bath
    • 1,051 Sq Ft
    • Built 1955

    Last Sold Summary

    • $105/SF
    • 6 Days On Market

    Current Estimated Value $121,440

    Last Listing Agent Alex Fox Allfirst Realty, Inc.

    201 Denton Rd, Federalsburg, MD 21632
    • /12

      Est $249,613

      Not Listed For Sale

      607 Academy Ave, Federalsburg, MD 21632

      • 3 Beds
      • 1 Bath
      • 1,148 Sq Ft
      • Built 1957
      607 Academy Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 72 Days On Market

      Last Listing Agent Lynette Bridges-Catha Hileman Real Estate Inc-Salisbury

  • /8

    $85,000

    • Land
    • 32,234 Sq Ft
    • $114,865 per Acre

    0 Mill & Lincoln St, Greensboro, MD 21639

    3 Parcels in the Town of Greensboro!! One of which has a hooked up Water/Sewer account, so instant savings on no tap fee!! Parcels are believed to total approximately 0.74 Acres, more or less. Abandoned dwelling exists in the center of the parcels, in need of tear down or possible major renovation. Town of Greensboro building codes and ordinances are online their website. NOTE: The parcel numbers

    Erin Anderson Chesapeake Real Estate Associates, LLC

    0 Mill & Lincoln St, Greensboro, MD 21639
  • /37

    $205,000

    Sold Apr 09, 2026

    318 Carter Ave, Denton, MD 21629

    • 2 Beds
    • 2 Baths
    • 606 Sq Ft
    • Built 1950

    Last Sold Summary

    • $338/SF
    • 96 Days On Market

    Current Estimated Value $202,029

    Last Listing Agent Georgi Chauvin Benson & Mangold, LLC

    318 Carter Ave, Denton, MD 21629
    • /16

      Est $206,306

      Not Listed For Sale

      207 Brooklyn Ave, Federalsburg, MD 21632

      • 3 Beds
      • 2 Baths
      • 1,216 Sq Ft
      • Built 2004
      207 Brooklyn Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Christina Smith Brenton Realty Group

  • /28

    $219,900

    $30K PRICE DROP Under Contract
    • 3 Beds
    • 1 Bath
    • 1,080 Sq Ft

    6413 Reliance Rd, Federalsburg, MD 21632

    Nice 3 bedroom 1 bath Rancher with garage in quiet country setting. This one will not last long!!

    Blaine Williamson McClain-Williamson Realty, LLC

    6413 Reliance Rd, Federalsburg, MD 21632
  • /60

    $400,000

    Sold Jan 06, 2026

    106 Briarwood Cir, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 2,551 Sq Ft
    • Built 2021

    Last Sold Summary

    • $157/SF
    • 4 Days On Market

    Current Estimated Value $406,147

    Last Listing Agent Stephanie Smith Douglas Realty, LLC

    106 Briarwood Cir, Denton, MD 21629
    • /10

      Est $231,922

      Not Listed For Sale

      1302 Blue Heron Dr, Denton, MD 21629

      • 3 Beds
      • 2.5 Baths
      • 1,753 Sq Ft
      • Built 2004
      1302 Blue Heron Dr, Denton, MD 21629

      Last Sold Summary

      • 114 Days On Market

      Last Listing Agent Mona Mohr Long & Foster Real Estate, Inc.

  • /6

    $49,900

    • Land
    • 2.55 Acres
    • $19,569 per Acre

    0 Havercamp Rd, 4, Preston, MD 21655

    If you’ve been searching for a private, wooded homesite without feeling too far removed from everyday conveniences, this is it. Offering over 2.5 acres, this property provides the perfect blend of seclusion and accessibility—ideal for building your dream home exactly the way you envision it. Located on Havercamp Rd, you’ll enjoy a peaceful, tucked-away setting while still being just minutes from

    Aubrey Campbell Keller Williams Realty Delmarva

    0 Havercamp Rd, 4, Preston, MD 21655
  • /20

    $189,000

    Sold Dec 02, 2025

    301 Central Ave, Ridgely, MD 21660

    • 4 Beds
    • 1 Bath
    • 1,706 Sq Ft
    • Built 1860

    Last Sold Summary

    • $111/SF
    • 7 Days On Market

    Current Estimated Value $193,879

    Last Listing Agent Jim Corson Benson & Mangold, LLC

    301 Central Ave, Ridgely, MD 21660
    • /32

      Est $347,723

      Not Listed For Sale

      501 Elaine Ave, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,884 Sq Ft
      • Built 1976
      501 Elaine Ave, Denton, MD 21629

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Joni Barrow Coldwell Banker Realty

  • /43

    $299,000

    Pending
    • 3 Beds
    • 1 Bath
    • 1,108 Sq Ft

    23884 Bridgetown Rd, Goldsboro, MD 21636

    Bridgetown Road - This 3 bedroom 1 bath home features a full unfinished basement for additional living space. The property is 3.55 acres on a corner lot. The detach garage is ready for your next project. The home has been painted, new vinyl flooring, new countertop, and new stove. Call today for your showing appointment.

    Linda Austin Long & Foster Real Estate, Inc.

    23884 Bridgetown Rd, Goldsboro, MD 21636
  • /22

    $364,000

    Sold May 20, 2026

    3 Sunrise Ave, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,292 Sq Ft
    • Built 2026

    Last Sold Summary

    • $282/SF
    • 134 Days On Market

    Last Listing Agent Amy Betts Coldwell Banker Realty

    3 Sunrise Ave, Ridgely, MD 21660
    • /33

      Est $603,542

      Not Listed For Sale

      14800 Day Rd, Goldsboro, MD 21636

      • 4 Beds
      • 2.5 Baths
      • 2,590 Sq Ft
      • Built 1992
      14800 Day Rd, Goldsboro, MD 21636

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Kathleen Brenton Brenton Realty Group

  • /31

    $269,000

    • 4 Beds
    • 2 Baths
    • 1,950 Sq Ft

    108 N Academy St, Greensboro, MD 21639

    This charming cape cod home is waiting for your creative touches! Lots of room on three floors. The main floor boasts a large living room with new vinyl flooring. A separate dining room, large kitchen, full bath and mudroom with washer and dryer. The second floor has four spacious bedrooms and a charming vintage bath with claw foot tub! The basement is a perfect place for crafts, hobbies and

    Marcia Rostien Long & Foster Real Estate, Inc.

    108 N Academy St, Greensboro, MD 21639
  • /21

    $249,500

    Sold Nov 10, 2025

    529 N 6th St, Denton, MD 21629

    • 3 Beds
    • 1 Bath
    • 1,019 Sq Ft
    • Built 1930

    Last Sold Summary

    • $245/SF
    • 62 Days On Market

    Current Estimated Value $242,112

    Last Listing Agent Cody Weese Weese Properties, LLC

    529 N 6th St, Denton, MD 21629
    • /23

      Est $373,302

      Not Listed For Sale

      28370 Bloomery Rd, Federalsburg, MD 21632

      • 4 Beds
      • 2 Baths
      • 1,749 Sq Ft
      • Built 1977
      28370 Bloomery Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Megan Carpenter Tesla Realty Group, LLC

  • /50

    $469,900

    • 4 Beds
    • 2.5 Baths
    • 2,488 Sq Ft

    9472 Quail Run Rd, Denton, MD 21629

    Denton - 4 bedroom home! This property offers an incredible opportunity to own a home with fantastic features, major mechanical updates, and no HOA! Inside, you will find a traditional layout highlighted by a large country kitchen featuring new countertops and an island. The formal dining room, den (with woodstove) and living room give ample opportunities for flex space. The primary bedroom

    Valerie Brown Coldwell Banker Realty

    9472 Quail Run Rd, Denton, MD 21629
  • /2

    $399,000

    Sold Jul 14, 2026

    24254 Mallow Dr, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,650 Sq Ft
    • Built 1999

    Last Sold Summary

    • $242/SF
    • 7 Days On Market

    Current Estimated Value $397,642

    Last Listing Agent Chris Haddaway Chesapeake Real Estate Associates, LLC

    24254 Mallow Dr, Preston, MD 21655
    • /22

      Est $230,587

      Not Listed For Sale

      203 Bernard Ave, Federalsburg, MD 21632

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1972
      203 Bernard Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 31 Days On Market

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

  • /53

    $525,000

    • 2 Beds
    • 1 Bath
    • 1,292 Sq Ft

    5820 Bell Creek Rd, Preston, MD 21655

    Don’t miss this exceptional 20+/- acre working horse farm thoughtfully designed for both functionality and country living. This well-equipped equestrian property offers everything needed for training, boarding, riding, and daily farm operations. The property features a 36’ x 40’ center-aisle barn with 9 stalls, water, electric, and an insulated tack room, along with a 77’ x 36’ metal barn

    Colleen Smith EXP Realty, LLC

    5820 Bell Creek Rd, Preston, MD 21655
  • /70

    $325,000

    Sold Mar 12, 2026

    25361 Calvert Dr, Greensboro, MD 21639

    • 3 Beds
    • 2 Baths
    • 1,450 Sq Ft
    • Built 1989

    Last Sold Summary

    • $224/SF
    • 50 Days On Market

    Current Estimated Value $333,875

    Last Listing Agent Chris Rosendale CR Realty

    25361 Calvert Dr, Greensboro, MD 21639
    • /10

      Est $244,499

      Not Listed For Sale

      319 Morris Ave, Federalsburg, MD 21632

      • 3 Beds
      • 2 Baths
      • 1,848 Sq Ft
      • Built 1989
      319 Morris Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 71 Days On Market

      Last Listing Agent Pamela Geib Long & Foster Real Estate, Inc.

  • /40

    $235,000

    Under Contract
    • 5 Beds
    • 3 Baths
    • 2,122 Sq Ft

    212 Main St, Preston, MD 21655

    Welcome to this spacious and beautifully maintained property nestled in the peaceful town of Preston. The main residence features 5 generously sized bedrooms and 3 full bathrooms, offering plenty of space for comfortable family living, guests, or multi-generational arrangements. At the heart of the home, you’ll find a large eat-in kitchen, perfect for gathering with family, hosting friends, or

    Ross Muir EXP Realty, LLC

    212 Main St, Preston, MD 21655
  • /71

    $450,000

    Sold Sep 19, 2025

    122 Lister Ln, Ridgely, MD 21660

    • 4 Beds
    • 3 Baths
    • 4,304 Sq Ft
    • Built 2006

    Last Sold Summary

    • $105/SF
    • 30 Days On Market

    Current Estimated Value $446,722

    Last Listing Agent Chris Rosendale CR Realty

    122 Lister Ln, Ridgely, MD 21660
    • /68

      Est $648,902

      Not Listed For Sale

      25840 Garey Rd, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,702 Sq Ft
      • Built 1900
      25840 Garey Rd, Denton, MD 21629

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent June Steinweg Long & Foster Real Estate, Inc.

  • /33

    $345,000

    • 4 Beds
    • 2 Baths
    • 2,172 Sq Ft

    612 Market St, Denton, MD 21629

    Step back in time while enjoying the comforts of modern living in this beautifully maintained 1900s historic home nestled in the heart of Denton. Rich with character and timeless charm, this spacious four-bedroom, two-bath residence showcases many of the architectural details that make historic homes so special, including original hardwood floors, detailed moldings, tall ceilings, oversized

    Joelle Dolch Cross Street Realtors LLC

    612 Market St, Denton, MD 21629
  • /23

    $365,000

    Sold Dec 22, 2025

    8 Sunrise Ave, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,292 Sq Ft
    • Built 2025

    Last Sold Summary

    • $283/SF
    • 6 Days On Market

    Last Listing Agent Amy Betts Coldwell Banker Realty

    8 Sunrise Ave, Ridgely, MD 21660
    • /20

      Est $284,451

      Not Listed For Sale

      1223 Fairfield Ct, Denton, MD 21629

      • 3 Beds
      • 2 Baths
      • 1,224 Sq Ft
      • Built 2004
      1223 Fairfield Ct, Denton, MD 21629

      Last Sold Summary

      • 49 Days On Market

      Last Listing Agent Jana Meredith Meredith Fine Properties

  • /2

    $55,000

    • Land
    • 4.17 Acres
    • $13,189 per Acre

    E/S MD RT480 Unknown, Hillsboro, MD 21641

    Seller is waiting for perk results from Caroline county health department

    Diane Wenk Wright Real Estate

    E/S MD RT480 Unknown, Hillsboro, MD 21641

Showing Results 601 - 640, Page 16 of 18

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