15,671

Caroline County, MD Homes

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  • 17690 Melville Rd, Henderson, MD 21640
    17690 Melville Rd, Henderson, MD 21640
    17690 Melville Rd, Henderson, MD 21640
    /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
    • 202 N Central Ave, Ridgely, MD 21660
      202 N Central Ave, Ridgely, MD 21660
      202 N Central Ave, Ridgely, MD 21660
      /45

      Est $393,307 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 2,668 Sq Ft

      202 N Central Ave, Ridgely, MD 21660

      202 N Central Ave, Ridgely, MD 21660
  • 1403 Blue Heron Dr, Denton, MD 21629
    1403 Blue Heron Dr, Denton, MD 21629
    1403 Blue Heron Dr, Denton, MD 21629
    /38

    $225,000

    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    1403 Blue Heron Dr, Denton, MD 21629

    BACK ON THE MARKET Buyer change of plans — which means you get another shot at this amazing home! Don’t miss it this time! Welcome Home to Low-Maintenance Living! 1403 Blue Heron Drive, Denton Step inside this cozy, turn-key 3-level townhome nestled in the highly desired Mallard Landing community! Boasting over 1,680 sq ft, this 3-bedroom, 2.5-bath residence.. The open-concept main floor is

    Dale Hunter Bayside Realty

    1403 Blue Heron Dr, Denton, MD 21629
  • 17791 Keens Fright Ln, Henderson, MD 21640
    17791 Keens Fright Ln, Henderson, MD 21640
    17791 Keens Fright Ln, Henderson, MD 21640
    /27

    $675,000 Sold Feb 26, 2025

    17791 Keens Fright Ln, Henderson, MD 21640

    • 4 Beds
    • 2.5 Baths
    • 3,356 Sq Ft
    • Built 2006

    Last Sold Summary

    • $201/SF
    • 16 Days On Market

    Current Estimated Value $715,081

    Last Listing Agent Elisabeth Yeager Homes and Farms Real Estate

    17791 Keens Fright Ln, Henderson, MD 21640
    • 18 Lister Ln, Ridgely, MD 21660
      18 Lister Ln, Ridgely, MD 21660
      18 Lister Ln, Ridgely, MD 21660
      /44

      Est $467,028 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,252 Sq Ft

      18 Lister Ln, Ridgely, MD 21660

      18 Lister Ln, Ridgely, MD 21660
  • 10 Sunrise Ave, Ridgely, MD 21660
    10 Sunrise Ave, Ridgely, MD 21660
    10 Sunrise Ave, Ridgely, MD 21660
    /21

    $399,000 Pending

    • 4 Beds
    • 4 Baths
    • 1,768 Sq Ft

    10 Sunrise Ave, Ridgely, MD 21660

    Welcome to Sunrise Village! Construction is Complete and ready for its very first owners! Built by Lomaxx Custom Homes This brand-new construction offers 4 spacious bedrooms and 2.5 bathrooms, thoughtfully designed with modern finishes throughout. The heart of the home features a stylish kitchen with quartz countertops, seamlessly flowing into open living areas with luxury vinyl plank flooring.

    Amy Betts Coldwell Banker Realty

    10 Sunrise Ave, Ridgely, MD 21660
  • 111 Parkland Rd, Greensboro, MD 21639
    111 Parkland Rd, Greensboro, MD 21639
    /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 K Wood D.R. Horton Realty of Virginia, LLC

    111 Parkland Rd, Greensboro, MD 21639
    • 23592 Henry Rd, Ridgely, MD 21660
      23592 Henry Rd, Ridgely, MD 21660
      23592 Henry Rd, Ridgely, MD 21660
      /15

      Est $341,580 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,452 Sq Ft

      23592 Henry Rd, Ridgely, MD 21660

      23592 Henry Rd, Ridgely, MD 21660
  • 11146 Branch Ct, Denton, MD 21629
    11146 Branch Ct, Denton, MD 21629
    11146 Branch Ct, Denton, MD 21629
    /20

    $244,900

    • 1 Bath

    11146 Branch Ct, Denton, MD 21629

    1.65 Acres with Well and Septic in Place!! 3 Bay Garage with one Pass-thru Unit - Features include - extra storage, Office, Kitchenette,and Full Bath. Come Build your Dream Home.!! Lot features U shape Driveway with Plenty of parking and nicely landscaped with mature trees. . Check with County for all your many possiblities! Conviently located with in minutes to Downtown Denton, Choptank River

    Kathleen Brenton Brenton Realty Group

    11146 Branch Ct, Denton, MD 21629
  • 23209 Gilpin Point Rd, Preston, MD 21655
    23209 Gilpin Point Rd, Preston, MD 21655
    23209 Gilpin Point Rd, Preston, MD 21655
    /8

    $470,000 Sold Jan 30, 2025

    23209 Gilpin Point Rd, Preston, MD 21655

    • 2 Beds
    • 1 Bath
    • 1,560 Sq Ft
    • Built 1965

    Last Sold Summary

    • $301/SF
    • 127 Days On Market

    Current Estimated Value $499,877

    Last Listing Agent rachael harrison Coldwell Banker Realty

    23209 Gilpin Point Rd, Preston, MD 21655
    • 1130 Osprey Ln, Denton, MD 21629
      1130 Osprey Ln, Denton, MD 21629
      1130 Osprey Ln, Denton, MD 21629
      /69

      Est $419,868 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,644 Sq Ft

      1130 Osprey Ln, Denton, MD 21629

      1130 Osprey Ln, Denton, MD 21629
  • 103 Park Ave Unit 36203274, Greensboro, MD 21639
    103 Park Ave Unit 36203274, Greensboro, MD 21639
    /2

    $291,990 New Construction

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

    HELENA Plan at Kinnamon Meadows, Greensboro, MD 21639

    The Helena is an inviting 1,460 square foot cottage-style ranch home that offers four bedrooms, two bathrooms, and a one-car garage. The long, welcoming foyer of this home allows for the three guest bedrooms and guest bathroom to be separate from the living areas of the home. The oversized great room with an abundance of natural light is open to the kitchen making an ideal space to entertain or

    D.R. Horton Builder
    103 Park Ave Unit 36203274, Greensboro, MD 21639
  • 12087 Lincoln St, Ridgely, MD 21660
    12087 Lincoln St, Ridgely, MD 21660
    12087 Lincoln St, Ridgely, MD 21660
    /22

    $275,000 Sold Jan 23, 2025

    12087 Lincoln St, Ridgely, MD 21660

    • 3 Beds
    • 3 Baths
    • 1,512 Sq Ft
    • Built 1945

    Last Sold Summary

    • $182/SF
    • 56 Days On Market

    Current Estimated Value $293,427

    Last Listing Agent Lawrence Lessin Save 6, Incorporated

    12087 Lincoln St, Ridgely, MD 21660
    • 321 S University Ave, Federalsburg, MD 21632
      321 S University Ave, Federalsburg, MD 21632
      321 S University Ave, Federalsburg, MD 21632
      /28

      Est $184,607 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 780 Sq Ft

      321 S University Ave, Federalsburg, MD 21632

      321 S University Ave, Federalsburg, MD 21632
  • 13539 Hokum Dr, Greensboro, MD 21639
    13539 Hokum Dr, Greensboro, MD 21639
    13539 Hokum Dr, Greensboro, MD 21639
    /99

    $1,100,000

    • 6 Beds
    • 3.5 Baths
    • 3,704 Sq Ft

    13539 Hokum Dr, Greensboro, MD 21639

    A Private Eastern Shore Compound Designed for Living, Relaxing & Entertaining!Welcome to 13539 Hokum Drive, a rare Eastern Shore retreat offering privacy, amenities, and “room to breathe” on a gorgeous, partially wooded landscape. This isn’t just a home — it’s a full lifestyle setting, complete with multiple outbuildings, an in-ground pool, wooded trails, and incredible outdoor living spaces,

    Vincent Payne Realty Navigator

    13539 Hokum Dr, Greensboro, MD 21639
  • 8556 Tuckahoe Rd, Denton, MD 21629
    8556 Tuckahoe Rd, Denton, MD 21629
    8556 Tuckahoe 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

    Last Listing Agent Kathleen Armiger Coldwell Banker Realty

    8556 Tuckahoe Rd, Denton, MD 21629
    • 526 High St, Denton, MD 21629
      526 High St, Denton, MD 21629
      526 High St, Denton, MD 21629
      /17

      Est $230,756 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,232 Sq Ft

      526 High St, Denton, MD 21629

      526 High St, Denton, MD 21629
  • 26623 Bee Tree Rd, Henderson, MD 21640
    26623 Bee Tree Rd, Henderson, MD 21640
    26623 Bee Tree Rd, Henderson, MD 21640
    /34

    $339,900

    • 3 Beds
    • 1 Bath
    • 1,104 Sq Ft

    26623 Bee Tree Rd, Henderson, MD 21640

    OPEN HOUSE this Sat. 12/13/25 3-5pm! Outdoorsman’s Paradise on 4+ Acres! Discover your own private retreat with this beautifully updated countryside home, perfectly designed for comfort, adventure, and peaceful living. Recent upgrades include stylish and durable LVP flooring, a spacious, fully renovated bathroom, a fully encapsulated crawlspace, and a long-lasting metal roof for years of

    Rick Parreco RE/MAX Executive

    26623 Bee Tree Rd, Henderson, MD 21640
  • 26042 Line Rd, Denton, MD 21629
    26042 Line Rd, Denton, MD 21629
    26042 Line Rd, 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
    • 11458 Reed Cir, Ridgely, MD 21660
      11458 Reed Cir, Ridgely, MD 21660
      11458 Reed Cir, Ridgely, MD 21660
      /19

      Est $418,746 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,440 Sq Ft

      11458 Reed Cir, Ridgely, MD 21660

      11458 Reed Cir, Ridgely, MD 21660
  • 115 Boyce Mill Rd, Greensboro, MD 21639
    115 Boyce Mill Rd, Greensboro, MD 21639
    115 Boyce Mill Rd, Greensboro, MD 21639
    /25

    $219,000 Under Contract

    • 3 Beds
    • 1 Bath
    • 1,350 Sq Ft

    115 Boyce Mill Rd, Greensboro, MD 21639

    This property is full of character, rare to find beautiful pine paneling in its natural state. With Built-in book shelves and hard wood flooring under the carpets original to the house. A spare room on the first floor could be used as a 4th bedroom . The basement has room for expansion as well. The back deck is great for entertaining or just enjoying the view. Solid house making this appealing to

    Kat Thompson Benson & Mangold, LLC.

    115 Boyce Mill Rd, Greensboro, MD 21639
  • 13800 Cedar Ln, Greensboro, MD 21639
    13800 Cedar Ln, Greensboro, MD 21639
    13800 Cedar Ln, Greensboro, MD 21639
    /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 $457,754

    Last Listing Agent Lona Todd Taylor Properties

    13800 Cedar Ln, Greensboro, MD 21639
    • 23 Lister Ln, Ridgely, MD 21660
      23 Lister Ln, Ridgely, MD 21660
      23 Lister Ln, Ridgely, MD 21660
      /42

      Est $462,506 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 3,441 Sq Ft

      23 Lister Ln, Ridgely, MD 21660

      23 Lister Ln, Ridgely, MD 21660
  • 4935 Edmondson Creek Rd, Preston, MD 21655
    4935 Edmondson Creek Rd, Preston, MD 21655
    4935 Edmondson Creek Rd, Preston, MD 21655
    /10

    $318,000 Under Contract

    • 2 Beds
    • 1 Bath
    • 1,438 Sq Ft

    4935 Edmondson Creek Rd, Preston, MD 21655

    Approximately 2 acres (parcels 289, 196) on a point on Little Creek off the Choptank River. Two bedroom, one bath log cabin with loft. An additional accessary log cabin. Easy access to Easton or Preston. Great waterfowl location.

    Randy Staats Benson & Mangold, LLC

    4935 Edmondson Creek Rd, Preston, MD 21655
  • 17990 Henderson Rd, Marydel, MD 21649
    17990 Henderson Rd, Marydel, MD 21649
    17990 Henderson Rd, Marydel, MD 21649
    /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

    Last Listing Agent Timothy Morgan Keller Williams Realty Delmarva

    17990 Henderson Rd, Marydel, MD 21649
    • 27515 Anthony Mill Rd, Denton, MD 21629
      27515 Anthony Mill Rd, Denton, MD 21629
      27515 Anthony Mill Rd, Denton, MD 21629
      /15

      Est $72,990 Not Listed For Sale

      27515 Anthony Mill Rd, Denton, MD 21629

      27515 Anthony Mill Rd, Denton, MD 21629
  • 9946 New Bridge Rd, Denton, MD 21629
    9946 New Bridge Rd, Denton, MD 21629
    9946 New Bridge Rd, Denton, MD 21629
    /28

    $250,000 Pending

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    9946 New Bridge Rd, Denton, MD 21629

    Offers due Monday 12/8 by 6pm! This updated 3-bedroom, 1-bath rancher sits on a half-acre lot just outside Denton. This charming home features a newer roof, windows, and back deck. The kitchen has also been updated with new cabinets and countertops. It offers peaceful country living while still being close to Denton amenities. Enjoy easy access to Routes 404 and 50 for convenient commuting.

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    9946 New Bridge Rd, Denton, MD 21629
  • 222 Denton Rd, Federalsburg, MD 21632
    222 Denton Rd, Federalsburg, MD 21632
    222 Denton Rd, Federalsburg, MD 21632
    /3

    $27,500 Sold Dec 04, 2025

    222 Denton Rd, Federalsburg, MD 21632

    • Land
    • 0.23 Acre
    • $119,565 per Acre

    Last Sold Summary

    • 589 Days On Market

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

    222 Denton Rd, Federalsburg, MD 21632
    • 304 Kerr Ave, Denton, MD 21629
      304 Kerr Ave, Denton, MD 21629
      304 Kerr Ave, Denton, MD 21629
      /15

      Est $375,517 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,808 Sq Ft

      304 Kerr Ave, Denton, MD 21629

      304 Kerr Ave, Denton, MD 21629
  • 120 Parkland Rd, Greensboro, MD 21639
    120 Parkland Rd, Greensboro, MD 21639
    120 Parkland Rd, Greensboro, MD 21639
    /20

    $259,990 Pending

    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft

    120 Parkland Rd, Greensboro, MD 21639

    Discover the Perry in Kinnamon Meadows, a 1,059 square foot open concept cottage-style ranch home, offering two bedrooms and two bathrooms at 124 Parkland Road in Greensboro, MD. A welcoming front porch leads you into the spacious living room that seamlessly flows into the kitchen, creating a perfect space for entertaining guests or enjoying family time. The well-equipped kitchen is complete with

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

    120 Parkland Rd, Greensboro, MD 21639
  • 25211 Adams Landing Rd, Denton, MD 21629
    25211 Adams Landing Rd, Denton, MD 21629
    25211 Adams Landing Rd, Denton, MD 21629
    /58

    $700,000 Sold Dec 17, 2025

    25211 Adams Landing Rd, Denton, MD 21629

    • 4 Beds
    • 2 Baths
    • 2,273 Sq Ft
    • Built 1960

    Last Sold Summary

    • $308/SF
    • 12 Days On Market

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

    25211 Adams Landing Rd, Denton, MD 21629
    • 5577 Harmony Woods Dr, Preston, MD 21655
      5577 Harmony Woods Dr, Preston, MD 21655
      5577 Harmony Woods Dr, Preston, MD 21655
      /47

      Est $516,037 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,526 Sq Ft

      5577 Harmony Woods Dr, Preston, MD 21655

      5577 Harmony Woods Dr, Preston, MD 21655
  • 21084 Marsh Creek Rd, Preston, MD 21655
    21084 Marsh Creek Rd, Preston, MD 21655
    21084 Marsh Creek Rd, Preston, MD 21655
    /9

    $299,900 Pending

    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft

    21084 Marsh Creek Rd, Preston, MD 21655

    Amazing opportunity for a 1st time buyer or investor. The home has been recently renovated to include new kitchen cabinets, counter tops, appliances, flooring, ceiling fans, base board heating units, new windows and painting. The roof was replaced in 2024. The home is move in ready, just bring your furniture.

    Eddie Matthews Benson & Mangold, LLC

    21084 Marsh Creek Rd, Preston, MD 21655
  • 116 Maple Ave, Preston, MD 21655
    116 Maple Ave, Preston, MD 21655
    116 Maple Ave, Preston, MD 21655
    /5

    $238,000 Sold Sep 24, 2025

    116 Maple Ave, Preston, MD 21655

    • 2 Beds
    • 1.5 Baths
    • 1,458 Sq Ft
    • Built 1915

    Last Sold Summary

    • $163/SF
    • 69 Days On Market

    Last Listing Agent Mary Haddaway Benson & Mangold, LLC

    116 Maple Ave, Preston, MD 21655
    • 109 Sunset Blvd, Preston, MD 21655
      109 Sunset Blvd, Preston, MD 21655
      109 Sunset Blvd, Preston, MD 21655
      /46

      Est $358,609 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,632 Sq Ft

      109 Sunset Blvd, Preston, MD 21655

      109 Sunset Blvd, Preston, MD 21655
  • 3540 Houston Branch Rd, Federalsburg, MD 21632
    3540 Houston Branch Rd, Federalsburg, MD 21632
    3540 Houston Branch Rd, Federalsburg, MD 21632
    /35

    $279,000

    • 2 Beds
    • 1 Bath
    • 1,140 Sq Ft

    3540 Houston Branch Rd, Federalsburg, MD 21632

    Welcome to 3540 Houston Branch Rd. It was purchased in 2021 and has undergone extensive renovations. The interior was taken down to the studs. There is new drywall, flooring and sub flooring, a complete bath room, windows, kitchen cabinets, appliances and quartz counter tops. Even the electric was updated along with plumbing. Did I mention a new roof, well and septic system!! This is a perfect

    Eddie Matthews Benson & Mangold, LLC

    3540 Houston Branch Rd, Federalsburg, MD 21632
  • 306 Kerr Ave, Denton, MD 21629
    306 Kerr Ave, Denton, MD 21629
    306 Kerr Ave, Denton, MD 21629
    /34

    $386,000 Sold Jun 27, 2025

    306 Kerr Ave, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,064 Sq Ft
    • Built 2005

    Last Sold Summary

    • $187/SF
    • 48 Days On Market

    Current Estimated Value $416,051

    Last Listing Agent Justin Pokrywka Taylor Properties

    306 Kerr Ave, Denton, MD 21629
    • 1311 Fairfield Ct, Denton, MD 21629
      1311 Fairfield Ct, Denton, MD 21629
      1311 Fairfield Ct, Denton, MD 21629
      /15

      Est $346,655 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,360 Sq Ft

      1311 Fairfield Ct, Denton, MD 21629

      1311 Fairfield Ct, Denton, MD 21629
  • 13306 Greensboro Rd, Greensboro, MD 21639
    13306 Greensboro Rd, Greensboro, MD 21639
    13306 Greensboro Rd, Greensboro, MD 21639
    /48

    $355,000

    • 2 Beds
    • 1.5 Baths
    • 708 Sq Ft

    13306 Greensboro Rd, Greensboro, MD 21639

    Stunning waterfront renovation on the Choptank River—completely redone inside and out in 2025! This beautifully updated 2-bedroom, 1.5-bath home offers approximately 800± square feet of thoughtfully designed living space. Completely remodeled from top to bottom, the residence showcases modern design and high-end finishes throughout. Updates include all-new walls, bathrooms, appliances, kitchen

    Lisa Magnus Clark & Co Realty, LLC

    13306 Greensboro Rd, Greensboro, MD 21639
  • 0 Laurel Grove Unit MDCM2004422, Federalsburg, MD 21632
    0 Laurel Grove Unit MDCM2004422, Federalsburg, MD 21632
    0 Laurel Grove Unit MDCM2004422, Federalsburg, MD 21632
    /8

    $125,100 Sold Jun 12, 2025

    0 Laurel Grove Unit MDCM2004422, Federalsburg, MD 21632

    • Land
    • 9.42 Acres
    • $13,280 per Acre

    Last Sold Summary

    • 291 Days On Market

    Last Listing Agent Diane Wenk Wright Real Estate

    0 Laurel Grove Unit MDCM2004422, Federalsburg, MD 21632

Showing Results 521 - 560, Page 14 of 18

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