15,671

Caroline County, MD Homes

Section Image
  • 23993 E Cherry Ln, Goldsboro, MD 21636
    23993 E Cherry Ln, Goldsboro, MD 21636
    23993 E Cherry Ln, Goldsboro, MD 21636
    /17

    $110,000 Sold Apr 11, 2025

    23993 E Cherry Ln, Goldsboro, MD 21636

    • Land
    • 2.2 Acres
    • $50,000 per Acre

    Last Sold Summary

    • 2 Days On Market

    Current Estimated Value $116,528

    Last Listing Agent Kathleen Brenton Brenton Realty Group

    23993 E Cherry Ln, Goldsboro, MD 21636
    • 25970 Three Bridges Rd, Federalsburg, MD 21632
      25970 Three Bridges Rd, Federalsburg, MD 21632
      25970 Three Bridges Rd, Federalsburg, MD 21632
      /66

      Est $322,549 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,844 Sq Ft

      25970 Three Bridges Rd, Federalsburg, MD 21632

      25970 Three Bridges Rd, Federalsburg, MD 21632
  • 25699 Auction Rd, Federalsburg, MD 21632
    25699 Auction Rd, Federalsburg, MD 21632
    25699 Auction Rd, Federalsburg, MD 21632
    /71

    $500,000

    • 4 Beds
    • 2 Baths
    • 1,986 Sq Ft

    25699 Auction Rd, Federalsburg, MD 21632

    ***BUYER WALKED AWAY!!****Mortgage savings may be available for buyers of this home. Opportunity to purchase a working farm with remodeled residence - from new luxury vinyl plank flooring and Advantech subfloors to a fully replaced middle beam for lasting structural integrity. Nearly all windows and doors are brand new, the heating system has been upgraded to an efficient heat pump, and the

    Barbara McCaffrey Redfin Corp

    25699 Auction Rd, Federalsburg, MD 21632
  • 403 Gay St, Denton, MD 21629
    403 Gay St, Denton, MD 21629
    403 Gay St, Denton, MD 21629
    /25

    $420,000 Sold Feb 11, 2025

    403 Gay St, Denton, MD 21629

    • Studio
    • 1,280 Sq Ft
    • Built 1880

    Last Sold Summary

    • $328/SF
    • 93 Days On Market

    Last Listing Agent Andrew Beaven Wright Real Estate

    403 Gay St, Denton, MD 21629
    • 206 Maple Ave, Ridgely, MD 21660
      206 Maple Ave, Ridgely, MD 21660
      206 Maple Ave, Ridgely, MD 21660
      /19

      Est $231,968 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,248 Sq Ft

      206 Maple Ave, Ridgely, MD 21660

      206 Maple Ave, Ridgely, MD 21660
  • 6 N Central Ave, Ridgely, MD 21660
    6 N Central Ave, Ridgely, MD 21660
    /2

    $79,900

    • Land
    • 0.21 Acre
    • $380,476 per Acre

    6 N Central Ave, Ridgely, MD 21660

    Zoned commercial is this prime lot in the heart of Ridgely and next to the Town Office. Convenient street parking fronting the lot.

    Chuck Jr. Benson and Mangold

    6 N Central Ave, Ridgely, MD 21660
  • 28471 Kinder Rd, Federalsburg, MD 21632
    28471 Kinder Rd, Federalsburg, MD 21632
    28471 Kinder Rd, Federalsburg, MD 21632
    /5

    $132,000 Sold Sep 25, 2025

    28471 Kinder Rd, Federalsburg, MD 21632

    • 3 Beds
    • 1 Bath
    • 640 Sq Ft
    • Built 1963

    Last Sold Summary

    • $206/SF
    • 71 Days On Market

    Last Listing Agent Gillian Walsh Worthington Realty Group, LLC

    28471 Kinder Rd, Federalsburg, MD 21632
    • 24776 Tribbett Cir, Ridgely, MD 21660
      24776 Tribbett Cir, Ridgely, MD 21660
      24776 Tribbett Cir, Ridgely, MD 21660
      /5

      Est $507,182 Not Listed For Sale

      24776 Tribbett Cir, Ridgely, MD 21660

      24776 Tribbett Cir, Ridgely, MD 21660
  • 2766 Veterans Dr, Federalsburg, MD 21632
    2766 Veterans Dr, Federalsburg, MD 21632
    2766 Veterans Dr, Federalsburg, MD 21632
    /100

    $299,000

    • 3 Beds
    • 1 Bath
    • 1,284 Sq Ft

    2766 Veterans Dr, Federalsburg, MD 21632

    ""PRICE REDUCTION"" *Attention, All "OUTDOOR ENTHUSIAST" are Welcome!!! This Unique Property is comprised of Multiple Deep Water Ponds loaded with a variety of fish making fishing TOP NOTCH and the back Woods loaded with Deer. Truly A Nature Lovers Dream, offers Peace & Tranquility, like no other, You can look long and hard and not find a property like this. This property has a gently rolling

    Barbara Beaudet Brenton Realty Group

    2766 Veterans Dr, Federalsburg, MD 21632
  • 6238 Bethlehem Rd, Preston, MD 21655
    6238 Bethlehem Rd, Preston, MD 21655
    6238 Bethlehem Rd, Preston, MD 21655
    /37

    $238,000 Sold Oct 07, 2025

    6238 Bethlehem Rd, Preston, MD 21655

    • 2 Beds
    • 1 Bath
    • 1,234 Sq Ft
    • Built 1875

    Last Sold Summary

    • $193/SF
    • 34 Days On Market

    Last Listing Agent Amy Betts Coldwell Banker Realty

    6238 Bethlehem Rd, Preston, MD 21655
    • 1202 Trice Meadows Cir, Denton, MD 21629
      1202 Trice Meadows Cir, Denton, MD 21629
      1202 Trice Meadows Cir, Denton, MD 21629
      /27

      Est $370,178 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,540 Sq Ft

      1202 Trice Meadows Cir, Denton, MD 21629

      1202 Trice Meadows Cir, Denton, MD 21629
  • 501 Lincoln St, Denton, MD 21629
    501 Lincoln St, Denton, MD 21629
    501 Lincoln St, Denton, MD 21629
    /15

    $135,000

    • 3 Beds
    • 1.5 Baths
    • 1,664 Sq Ft

    501 Lincoln St, Denton, MD 21629

    Property is being sold As/ Is. Located on a corner lot. Owner has completed some work to the property, but additional work will be required. Please contact Denton Planning and Codes to verify remaining requirements to obtain an occupancy permit.

    Diane Wenk Wright Real Estate

    501 Lincoln St, Denton, MD 21629
  • 13243 Greensboro Rd, Greensboro, MD 21639
    13243 Greensboro Rd, Greensboro, MD 21639
    /2

    $100,000 Sold Nov 21, 2025

    13243 Greensboro Rd, Greensboro, MD 21639

    • 2 Beds
    • 2 Baths
    • 1,092 Sq Ft
    • Built 1910

    Last Sold Summary

    • $92/SF
    • 5 Days On Market

    Last Listing Agent Kat Thompson Benson & Mangold, LLC.

    13243 Greensboro Rd, Greensboro, MD 21639
    • 1101 Trice Meadows Cir, Denton, MD 21629
      1101 Trice Meadows Cir, Denton, MD 21629
      1101 Trice Meadows Cir, Denton, MD 21629
      /10

      Est $420,378 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,300 Sq Ft

      1101 Trice Meadows Cir, Denton, MD 21629

      1101 Trice Meadows Cir, Denton, MD 21629
  • 0 River Rd Unit MDCM2005824, Ridgely, MD 21660
    0 River Rd Unit MDCM2005824, Ridgely, MD 21660
    /2

    $440,000

    • Land
    • 44.74 Acres
    • $9,835 per Acre

    0 River Rd Unit MDCM2005824, Ridgely, MD 21660

    Secluded property comprised of 2 perc approved parcels totaling 44.74 acres. This property is a mix of mature timber, wooded marshland, a tidal pond and frontage on the Choptank River. More info and photos soon.Tax id # 0607014147 and # 0607002408

    Andrew Beaven Wright Real Estate

    0 River Rd Unit MDCM2005824, Ridgely, MD 21660
  • 3590 Choptank Rd, Preston, MD 21655
    3590 Choptank Rd, Preston, MD 21655
    3590 Choptank Rd, Preston, MD 21655
    /44

    $355,000 Sold Aug 29, 2025

    3590 Choptank Rd, Preston, MD 21655

    • 3 Beds
    • 2 Baths
    • 1,476 Sq Ft
    • Built 1994

    Last Sold Summary

    • $241/SF
    • 32 Days On Market

    Current Estimated Value $373,343

    Last Listing Agent Dawn O'Day Samson Properties

    3590 Choptank Rd, Preston, MD 21655
    • 204 Briarwood Cir, Denton, MD 21629
      204 Briarwood Cir, Denton, MD 21629
      204 Briarwood Cir, Denton, MD 21629
      /15

      Est $381,226 Not Listed For Sale

      • 3 Beds
      • 2 Baths

      204 Briarwood Cir, Denton, MD 21629

      204 Briarwood Cir, Denton, MD 21629
  • 21948 Main St, Hillsboro, MD 21641
    21948 Main St, Hillsboro, MD 21641
    21948 Main St, Hillsboro, MD 21641
    /20

    $189,900

    • 3 Beds
    • 1 Bath
    • 1,904 Sq Ft

    21948 Main St, Hillsboro, MD 21641

    This home is high on a hill across from the Tuckahoe Creek with some winter views of the water. --the park across the street has a ramp for boats, kayaks, and canoes. The home has 3 bedrooms and a small room for office or nursery or whatever you want it to be;, and one full bath -- all upstairs. The front porch entrance opens to a foyer and the living room to the right and then the dining room

    Bonnie Duley Long & Foster Real Estate, Inc.

    21948 Main St, Hillsboro, MD 21641
  • 9585 Legion Rd, Denton, MD 21629
    9585 Legion Rd, Denton, MD 21629
    9585 Legion Rd, Denton, MD 21629
    /25

    $298,900 Sold Dec 26, 2024

    9585 Legion Rd, Denton, MD 21629

    • 2 Beds
    • 1 Bath
    • 1,291 Sq Ft
    • Built 1956

    Last Sold Summary

    • $232/SF
    • 64 Days On Market

    Current Estimated Value $340,138

    Last Listing Agent Ralph Harvey ListWithFreedom.com

    9585 Legion Rd, Denton, MD 21629
    • 613 Denton Rd, Federalsburg, MD 21632
      613 Denton Rd, Federalsburg, MD 21632
      613 Denton Rd, Federalsburg, MD 21632
      /21

      Est $235,573 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,008 Sq Ft

      613 Denton Rd, Federalsburg, MD 21632

      613 Denton Rd, Federalsburg, MD 21632
  • 15184 Jarrell Rd, Goldsboro, MD 21636
    15184 Jarrell Rd, Goldsboro, MD 21636
    15184 Jarrell Rd, Goldsboro, MD 21636
    /80

    $749,900

    • 6 Beds
    • 4.5 Baths
    • 5,000 Sq Ft

    15184 Jarrell Rd, Goldsboro, MD 21636

    BACK ON THE MARKET.....,Buyer financing fell through. All inspections (Home, Well and Septic) have been completed and any and all issues addressed. OWNER SAY: "COME ON DOWN, LET'S MAKE A DEAL" The Possibilities are endless on this, serene 12.12 acres just ready and waiting for you to turn it into your dream. The Property includes a Beautiful 5000+ square foot home and a Massive Detached 60X42

    Leslie Fulford Mann & Sons, Inc.

    15184 Jarrell Rd, Goldsboro, MD 21636
  • 8602 Hickory Place, 3, Denton, MD 21629
    8602 Hickory Place, 3, Denton, MD 21629
    8602 Hickory Place, 3, Denton, MD 21629
    /3

    $20,000 Sold Apr 23, 2025

    8602 Hickory Place, 3, Denton, MD 21629

    • Land
    • 1.28 Acres
    • $15,625 per Acre

    Last Sold Summary

    • 11 Days On Market

    Current Estimated Value $30,667

    Last Listing Agent Amanda Morgan Brenton Realty Group

    8602 Hickory Place, 3, Denton, MD 21629
    • 510 Lincoln St, Denton, MD 21629
      510 Lincoln St, Denton, MD 21629
      510 Lincoln St, Denton, MD 21629
      /3

      Est $294,478 Not Listed For Sale

      510 Lincoln St, Denton, MD 21629

      510 Lincoln St, Denton, MD 21629
  • 26056 Fox Grape Rd, Greensboro, MD 21639
    26056 Fox Grape Rd, Greensboro, MD 21639
    26056 Fox Grape Rd, Greensboro, MD 21639
    /24

    $275,000 Under Contract

    • 3 Beds
    • 1.5 Baths
    • 1,215 Sq Ft

    26056 Fox Grape Rd, Greensboro, MD 21639

    The Home You’ve Been Waiting For! Welcome to 26056 Fox Grape, where country charm meets modern functionality. This 3-bedroom, 1.5 -bath rancher boasts an open-concept layout with a spacious eat-in kitchen flowing seamlessly into the living area—perfect for gatherings and everyday comfort. Step outside to enjoy a 16x16 back deck overlooking a private, fully fenced yard with plenty of room to play,

    Amanda Morgan Brenton Realty Group

    26056 Fox Grape Rd, Greensboro, MD 21639
  • 103 Riverwalk Terrace, Federalsburg, MD 21632
    103 Riverwalk Terrace, Federalsburg, MD 21632
    103 Riverwalk Terrace, Federalsburg, MD 21632
    /27

    $218,990 Sold Jan 28, 2025

    103 Riverwalk Terrace, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 1,365 Sq Ft
    • Built 2024

    Last Sold Summary

    • $160/SF
    • 90 Days On Market

    Current Estimated Value $232,162

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

    103 Riverwalk Terrace, Federalsburg, MD 21632
    • 4845 Houston Branch Rd, Federalsburg, MD 21632
      4845 Houston Branch Rd, Federalsburg, MD 21632
      4845 Houston Branch Rd, Federalsburg, MD 21632
      /16

      Est $169,483 Not Listed For Sale

      4845 Houston Branch Rd, Federalsburg, MD 21632

      4845 Houston Branch Rd, Federalsburg, MD 21632
  • 229 Oldtown Rd, Goldsboro, MD 21636
    229 Oldtown Rd, Goldsboro, MD 21636
    229 Oldtown Rd, Goldsboro, MD 21636
    /27

    $265,000

    • 3 Beds
    • 2 Baths
    • 1,368 Sq Ft

    229 Oldtown Rd, Goldsboro, MD 21636

    Fully Remodeled 3 Bedroom, 2 Bath Home in the Heart of Goldsboro, MD Welcome to 229 Main Street, where modern style meets small-town charm. This beautifully remodeled 3-bedroom, 2 full bath home has been thoughtfully updated from top to bottom, offering the perfect blend of craftsmanship and comfort. Step inside to a bright, open floor plan featuring luxury vinyl plank flooring, fresh neutral

    Brett Schrader Taylor Properties

    229 Oldtown Rd, Goldsboro, MD 21636
  • 5569 Harmony Woods Dr, Preston, MD 21655
    5569 Harmony Woods Dr, Preston, MD 21655
    5569 Harmony Woods Dr, Preston, MD 21655
    /52

    $470,000 Sold Jun 11, 2025

    5569 Harmony Woods Dr, Preston, MD 21655

    • 4 Beds
    • 2.5 Baths
    • 2,909 Sq Ft
    • Built 2005

    Last Sold Summary

    • $162/SF
    • 185 Days On Market

    Current Estimated Value $511,210

    Last Listing Agent Erin Anderson Chesapeake Real Estate Associates, LLC

    5569 Harmony Woods Dr, Preston, MD 21655
    • 712 Gay St, Denton, MD 21629
      712 Gay St, Denton, MD 21629
      712 Gay St, Denton, MD 21629
      /13

      Not Listed For Sale

      • Studio
      • 2,184 Sq Ft

      712 Gay St, Denton, MD 21629

      712 Gay St, Denton, MD 21629
  • 28219 Bridgeville Rd, Federalsburg, MD 21632
    28219 Bridgeville Rd, Federalsburg, MD 21632
    28219 Bridgeville Rd, Federalsburg, MD 21632
    /89

    $2,750,000

    • 4 Beds
    • 4.5 Baths
    • 6,520 Sq Ft

    28219 Bridgeville Rd, Federalsburg, MD 21632

    First time on the market! Discover a rare opportunity to own a 105± acre estate on Maryland’s beautiful Eastern Shore, Close to tax free shopping and the beaches. Designed by renowned California architect David Watson, the exterior of this home is one of the all-time most downloaded photos on the popular homebuilding and design website, Houzz. This one-of-a-kind property combines luxury living,

    Jim Corson Benson & Mangold, LLC

    28219 Bridgeville Rd, Federalsburg, MD 21632
  • 313 Reliance Ave, Federalsburg, MD 21632
    313 Reliance Ave, Federalsburg, MD 21632
    313 Reliance Ave, Federalsburg, MD 21632
    /31

    $158,000 Sold Feb 26, 2025

    313 Reliance Ave, Federalsburg, MD 21632

    • 1 Bed
    • 1 Bath
    • 988 Sq Ft
    • Built 1960

    Last Sold Summary

    • $160/SF
    • 8 Days On Market

    Current Estimated Value $168,913

    Last Listing Agent Mary Jameson Long & Foster Real Estate, Inc.

    313 Reliance Ave, Federalsburg, MD 21632
    • 21994 Main St, Hillsboro, MD 21641
      21994 Main St, Hillsboro, MD 21641
      21994 Main St, Hillsboro, MD 21641
      /29

      Est $317,394 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 4,000 Sq Ft

      21994 Main St, Hillsboro, MD 21641

      21994 Main St, Hillsboro, MD 21641
  • 113 Parkland Rd, Greensboro, MD 21639
    113 Parkland Rd, Greensboro, MD 21639
    /2

    $269,990 Pending

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

    113 Parkland Rd, Greensboro, MD 21639

    Welcome to 113 Parkland Road, a new home under-construction 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 kitchen boasts stainless

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

    113 Parkland Rd, Greensboro, MD 21639
  • 25790 Herring Ln, Denton, MD 21629
    25790 Herring Ln, Denton, MD 21629
    25790 Herring Ln, Denton, MD 21629
    /34

    $469,000 Sold Oct 10, 2025

    25790 Herring Ln, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 2,132 Sq Ft
    • Built 1989

    Last Sold Summary

    • $220/SF
    • 18 Days On Market

    Last Listing Agent Elizabeth Tryon Meredith Fine Properties

    25790 Herring Ln, Denton, MD 21629
    • 5 Seward Rd, Ridgely, MD 21660
      5 Seward Rd, Ridgely, MD 21660
      5 Seward Rd, Ridgely, MD 21660
      /24

      Est $360,845 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,538 Sq Ft

      5 Seward Rd, Ridgely, MD 21660

      5 Seward Rd, Ridgely, MD 21660
  • 26067 Goldsboro Rd, Goldsboro, MD 21636
    26067 Goldsboro Rd, Goldsboro, MD 21636
    26067 Goldsboro Rd, Goldsboro, MD 21636
    /21

    $629,900 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,080 Sq Ft

    26067 Goldsboro Rd, Goldsboro, MD 21636

    One year new over 2,000 square foot custom built 3 bedroom 2 1/2 bath home with a 36' X 30' three care garage. Upgraded build with Pennsylvania pine beams, 2 zone heated floors for the house and garage, sprinkler system and whole house spray foam for maximum efficiency. Beautiful porches with view of trees, fields and wildlife. This home is sitting on over 2.50 acres with Wi-Fi and usb's on

    Scott Judy Coldwell Banker Waterman Realty

    26067 Goldsboro Rd, Goldsboro, MD 21636
  • 1111 Daylily Ln, Denton, MD 21629
    1111 Daylily Ln, Denton, MD 21629
    1111 Daylily Ln, Denton, MD 21629
    /26

    $402,000 Sold Dec 09, 2025

    1111 Daylily Ln, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 3,838 Sq Ft
    • Built 2007

    Last Sold Summary

    • $105/SF
    • 7 Days On Market

    Last Listing Agent Terri Murray RE/MAX Executive

    1111 Daylily Ln, Denton, MD 21629
    • 328 E Central Ave, Federalsburg, MD 21632
      328 E Central Ave, Federalsburg, MD 21632
      328 E Central Ave, Federalsburg, MD 21632
      /5

      Est $80,333 Not Listed For Sale

      328 E Central Ave, Federalsburg, MD 21632

      328 E Central Ave, Federalsburg, MD 21632
  • 107 Smith St, Federalsburg, MD 21632
    107 Smith St, Federalsburg, MD 21632
    107 Smith St, Federalsburg, MD 21632
    /39

    $229,990

    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft

    107 Smith St, Federalsburg, MD 21632

    A must see, updated + upgraded, 1-level, 3-bedroom,1.5-bath home with an open floorplan. Situated on a nice-sized yard, this welcoming home offers more than meets the eye. Handsome + durable luxury vinyl plank flooring, fresh paint, and updated fixtures throughout. Spacious living room with a bar and radiant countertops overlook the kitchen. Dining room with breakfast bar and sliding glass door.

    Brandon Brittingham EXP Realty, LLC

    107 Smith St, Federalsburg, MD 21632
  • 12400 & 12316 Ridgely Rd, Greensboro, MD 21639
    12400 & 12316 Ridgely Rd, Greensboro, MD 21639
    12400 & 12316 Ridgely Rd, Greensboro, MD 21639
    /14

    $2,000,000 Sold Mar 21, 2025

    12400 & 12316 Ridgely Rd, Greensboro, MD 21639

    • 3 Beds
    • 1 Bath
    • 1,896 Sq Ft
    • Built 1975

    Last Sold Summary

    • $1,055/SF
    • 7 Days On Market

    Last Listing Agent BRIAN MORRIS The Land Group

    12400 & 12316 Ridgely Rd, Greensboro, MD 21639

Showing Results 41 - 80, Page 2 of 18

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