15,675

Caroline County, MD Homes

Section Image Section Image
  • 24636 Williston Rd, Denton, MD 21629
    24636 Williston Rd, Denton, MD 21629
    24636 Williston Rd, Denton, MD 21629
    /25

    $350,000 Sold May 29, 2025

    24636 Williston Rd, Denton, MD 21629

    • 3 Beds
    • 1.5 Baths
    • 1,472 Sq Ft
    • Built 1959

    Last Sold Summary

    • $238/SF
    • 320 Days On Market

    Current Estimated Value $377,042

    Last Listing Agent Andrew Beaven Wright Real Estate

    24636 Williston Rd, Denton, MD 21629
    • 6 Oak St, Ridgely, MD 21660
      6 Oak St, Ridgely, MD 21660
      6 Oak St, Ridgely, MD 21660
      /19

      Est $341,677 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,480 Sq Ft

      6 Oak St, Ridgely, MD 21660

      6 Oak St, Ridgely, MD 21660
  • 11289 Gregg Rd, Denton, MD 21629
    11289 Gregg Rd, Denton, MD 21629
    11289 Gregg Rd, Denton, MD 21629
    /26

    $499,000

    • 4 Beds
    • 1.5 Baths
    • 2,320 Sq Ft

    11289 Gregg Rd, Denton, MD 21629

    Rare opportunity to purchase 19.1 acres with 2 dwellings, included property identified as 11285 Gregg Rd. Endless options to either rent one or have an in-law suite. It is said to have three septic systems, three electric services all on one property. Then main house which has the basement is in need of some remodeling, has 4 bedrooms and 1.1/4 baths, the remodling process has been started. The

    Kat Thompson Benson & Mangold, LLC.

    11289 Gregg Rd, Denton, MD 21629
  • 6315 Harmony Rd, Preston, MD 21655
    6315 Harmony Rd, Preston, MD 21655
    6315 Harmony Rd, Preston, MD 21655
    /36

    $325,000 Sold Sep 26, 2025

    6315 Harmony Rd, Preston, MD 21655

    • 3 Beds
    • 3 Baths
    • 2,016 Sq Ft
    • Built 1994

    Last Sold Summary

    • $161/SF
    • 28 Days On Market

    Current Estimated Value $340,870

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    6315 Harmony Rd, Preston, MD 21655
    • 312 Hughlett St, Preston, MD 21655
      312 Hughlett St, Preston, MD 21655
      312 Hughlett St, Preston, MD 21655
      /18

      Est $395,410 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,130 Sq Ft

      312 Hughlett St, Preston, MD 21655

      312 Hughlett St, Preston, MD 21655
  • 13539 Hokum Dr, Greensboro, MD 21639
    13539 Hokum Dr, Greensboro, MD 21639
    13539 Hokum Dr, Greensboro, MD 21639
    /99

    $1,099,000

    • 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
  • 25820 Dogwood Rd, Greensboro, MD 21639
    25820 Dogwood Rd, Greensboro, MD 21639
    25820 Dogwood Rd, Greensboro, MD 21639
    /59

    $385,000 Sold May 12, 2025

    25820 Dogwood Rd, Greensboro, MD 21639

    • 3 Beds
    • 2.5 Baths
    • 1,568 Sq Ft
    • Built 1979

    Last Sold Summary

    • $246/SF
    • 203 Days On Market

    Current Estimated Value $419,618

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

    25820 Dogwood Rd, Greensboro, MD 21639
    • 3 Robins Ct, Ridgely, MD 21660
      3 Robins Ct, Ridgely, MD 21660
      3 Robins Ct, Ridgely, MD 21660
      /54

      Est $466,893 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,898 Sq Ft

      3 Robins Ct, Ridgely, MD 21660

      3 Robins Ct, Ridgely, MD 21660
  • 5026 Bethlehem Rd, Preston, MD 21655
    5026 Bethlehem Rd, Preston, MD 21655
    /2

    $359,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,922 Sq Ft

    5026 Bethlehem Rd, Preston, MD 21655

    Totally renovated colonial offering nearly 2,000 sq ft of living space on a spacious 1/3-acre corner lot. Featuring 3, possibly 4 generous bedrooms and 2 full baths, this property showcases luxury vinyl plank flooring throughout. Enjoy privacy rear fencing and a large backyard—perfect for outdoor living. Ideal for a growing family and conveniently located close to Easton and Preston. This home is

    Linda Moore Long & Foster Real Estate, Inc.

    5026 Bethlehem Rd, Preston, MD 21655
  • 28268 Bridgeville Rd, Federalsburg, MD 21632
    28268 Bridgeville Rd, Federalsburg, MD 21632
    28268 Bridgeville Rd, Federalsburg, MD 21632
    /42

    $1,550,000 Sold Jun 13, 2025

    28268 Bridgeville Rd, Federalsburg, MD 21632

    • 4 Beds
    • 2 Baths
    • 1,888 Sq Ft
    • Built 1900

    Last Sold Summary

    • $821/SF
    • 11 Days On Market

    Current Estimated Value $1,596,302

    Last Listing Agent Nick Campanaro The Land Group

    28268 Bridgeville Rd, Federalsburg, MD 21632
    • 112 Vernon Ave, Federalsburg, MD 21632
      112 Vernon Ave, Federalsburg, MD 21632
      112 Vernon Ave, Federalsburg, MD 21632
      /10

      Est $158,089 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 884 Sq Ft

      112 Vernon Ave, Federalsburg, MD 21632

      112 Vernon Ave, Federalsburg, MD 21632
  • 25056 E Cherry Ln, Greensboro, MD 21639
    25056 E Cherry Ln, Greensboro, MD 21639
    25056 E Cherry Ln, Greensboro, MD 21639
    /4

    $5,250,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 3,150 Sq Ft

    25056 E Cherry Ln, Greensboro, MD 21639

    Beautiful farmstead situated on 410± acres, featuring 355± acres of highly productive tillable ground with approximately 210± acres under irrigation. The irrigation system consists of two pivots supplied by well water, supporting efficient and reliable crop production. The property includes a very well-maintained two-story, custom home that offers comfort, space and functionality. The upper level

    Michael Davis Phoenix Real Estate

    25056 E Cherry Ln, Greensboro, MD 21639
  • 25265 Smith Landing Rd, Denton, MD 21629
    25265 Smith Landing Rd, Denton, MD 21629
    25265 Smith Landing Rd, Denton, MD 21629
    /45

    $410,100 Sold Mar 18, 2025

    25265 Smith Landing Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 1976

    Last Sold Summary

    • $342/SF
    • 335 Days On Market

    Current Estimated Value $441,007

    Last Listing Agent Brenda Fornos Taylor Properties

    25265 Smith Landing Rd, Denton, MD 21629
    • 108 Liberty Rd, Federalsburg, MD 21632
      108 Liberty Rd, Federalsburg, MD 21632
      108 Liberty Rd, Federalsburg, MD 21632
      /24

      Est $234,081 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,756 Sq Ft

      108 Liberty Rd, Federalsburg, MD 21632

      108 Liberty Rd, Federalsburg, MD 21632
  • 25903 Dogwood Rd, Greensboro, MD 21639
    25903 Dogwood Rd, Greensboro, MD 21639
    25903 Dogwood Rd, Greensboro, MD 21639
    /28

    $330,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 1,590 Sq Ft

    25903 Dogwood Rd, Greensboro, MD 21639

    Welcome to the tucked away community of Fox Grape Farms. This home offers a comfortable layout designed for everyday living and easy entertaining. To the left of the foyer is the dining area that has stunning oak floors and exposed beams. The dining area is open to the kitchen which features great cabinet and counter space for cooking and prep. Bar seating at the kitchen counter and direct access

    Courtney Gallagher Keller Williams Realty Central-Delaware

    25903 Dogwood Rd, Greensboro, MD 21639
  • 6561 Bell Creek Rd, Preston, MD 21655
    6561 Bell Creek Rd, Preston, MD 21655
    6561 Bell Creek Rd, Preston, MD 21655
    /5

    $201,000 Sold Dec 19, 2025

    6561 Bell Creek Rd, Preston, MD 21655

    • 3 Beds
    • 1 Bath
    • 1,350 Sq Ft
    • Built 1915

    Last Sold Summary

    • $149/SF
    • 14 Days On Market

    Last Listing Agent Barbara Dayton Long & Foster Real Estate, Inc.

    6561 Bell Creek Rd, Preston, MD 21655
    • 505 S 2nd St, Denton, MD 21629
      505 S 2nd St, Denton, MD 21629
      505 S 2nd St, Denton, MD 21629
      /11

      Est $319,288 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,058 Sq Ft

      505 S 2nd St, Denton, MD 21629

      505 S 2nd St, Denton, MD 21629
  • 3540 Houston Branch Rd, Federalsburg, MD 21632
    3540 Houston Branch Rd, Federalsburg, MD 21632
    3540 Houston Branch Rd, Federalsburg, MD 21632
    /35

    $259,900

    • 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
  • 513 Vaughn Ave, Greensboro, MD 21639
    513 Vaughn Ave, Greensboro, MD 21639
    513 Vaughn Ave, Greensboro, MD 21639
    /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 $242,895

    Last Listing Agent Chad Muse KD Realty Inc

    513 Vaughn Ave, Greensboro, MD 21639
    • 217 Greenridge Rd, Federalsburg, MD 21632
      217 Greenridge Rd, Federalsburg, MD 21632
      217 Greenridge Rd, Federalsburg, MD 21632
      /20

      Est $227,829 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,276 Sq Ft

      217 Greenridge Rd, Federalsburg, MD 21632

      217 Greenridge Rd, Federalsburg, MD 21632
  • 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
  • 502 N Academy St, Greensboro, MD 21639
    502 N Academy St, Greensboro, MD 21639
    502 N Academy St, Greensboro, MD 21639
    /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 $381,167

    Last Listing Agent Chris Rosendale CR Realty

    502 N Academy St, Greensboro, MD 21639
    • 26280 Hobbs Rd, Denton, MD 21629
      26280 Hobbs Rd, Denton, MD 21629
      26280 Hobbs Rd, Denton, MD 21629
      /25

      Est $285,608 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 960 Sq Ft

      26280 Hobbs Rd, Denton, MD 21629

      26280 Hobbs Rd, Denton, MD 21629
  • 13364 River Rd, Greensboro, MD 21639
    13364 River Rd, Greensboro, MD 21639
    13364 River Rd, Greensboro, MD 21639
    /11

    $449,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft

    13364 River Rd, Greensboro, MD 21639

    NEARING COMPLETION!!....Discover this stunning, newly built ranch-style home situated on a spacious 2.6 acre unrestricted lot. Perfect for those seeking privacy and tranquility, this beautifully appointed residence features 3 bedroom and 2 bathrooms, attached 2 car garage, rear deck, conditioned crawlspace, offering comfortable living in a serene setting. Thoughtfully designed with high quality

    Linda Moore Long & Foster Real Estate, Inc.

    13364 River Rd, Greensboro, MD 21639
  • 0 Rte 313 Rd Unit 1001900376, Federalsburg, MD 21632
    0 Rte 313 Rd Unit 1001900376, Federalsburg, MD 21632
    0 Rte 313 Rd Unit 1001900376, Federalsburg, MD 21632
    /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
    • 23060 Tuckahoe Springs Dr, Denton, MD 21629
      23060 Tuckahoe Springs Dr, Denton, MD 21629
      23060 Tuckahoe Springs Dr, Denton, MD 21629
      /54

      Est $443,922 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,820 Sq Ft

      23060 Tuckahoe Springs Dr, Denton, MD 21629

      23060 Tuckahoe Springs Dr, Denton, MD 21629
  • E/S MD RT480 Unknown, Hillsboro, MD 21641
    E/S MD RT480 Unknown, Hillsboro, MD 21641
    /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
  • 14581 Poplar St, Goldsboro, MD 21636
    14581 Poplar St, Goldsboro, MD 21636
    14581 Poplar St, Goldsboro, MD 21636
    /11

    $250,000 Sold Mar 24, 2025

    14581 Poplar St, Goldsboro, MD 21636

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 2001

    Last Sold Summary

    • $203/SF
    • 118 Days On Market

    Current Estimated Value $275,537

    Last Listing Agent Peter Mellor Wright Real Estate

    14581 Poplar St, Goldsboro, MD 21636
    • 315 W Sunset Ave, Greensboro, MD 21639
      315 W Sunset Ave, Greensboro, MD 21639
      315 W Sunset Ave, Greensboro, MD 21639
      /50

      Est $375,053 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,416 Sq Ft

      315 W Sunset Ave, Greensboro, MD 21639

      315 W Sunset Ave, Greensboro, MD 21639
  • 151 Riverwalk Terrace, Federalsburg, MD 21632
    151 Riverwalk Terrace, Federalsburg, MD 21632
    151 Riverwalk Terrace, 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 $249,541

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

    151 Riverwalk Terrace, Federalsburg, MD 21632
    • 1211 Cattail Commons Way, Denton, MD 21629
      1211 Cattail Commons Way, Denton, MD 21629
      1211 Cattail Commons Way, Denton, MD 21629
      /44

      Est $422,488 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,036 Sq Ft

      1211 Cattail Commons Way, Denton, MD 21629

      1211 Cattail Commons Way, Denton, MD 21629
  • 0 Liberty Rd, Federalsburg, MD 21632
    0 Liberty Rd, Federalsburg, MD 21632
    0 Liberty Rd, Federalsburg, MD 21632
    /8

    $83,500 Sold Jun 20, 2025

    0 Liberty Rd, Federalsburg, MD 21632

    • Land
    • 7.9 Acres
    • $10,570 per Acre

    Last Sold Summary

    • 11 Days On Market

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

    0 Liberty Rd, Federalsburg, MD 21632
    • 1107 Canvasback Ln, Denton, MD 21629
      1107 Canvasback Ln, Denton, MD 21629
      1107 Canvasback Ln, Denton, MD 21629
      /29

      Est $440,075 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,496 Sq Ft

      1107 Canvasback Ln, Denton, MD 21629

      1107 Canvasback Ln, Denton, MD 21629
  • 118 Edenton Ln, Denton, MD 21629
    118 Edenton Ln, Denton, MD 21629
    118 Edenton Ln, Denton, MD 21629
    /41

    $300,000 Sold Apr 11, 2025

    118 Edenton Ln, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,479 Sq Ft
    • Built 1975

    Last Sold Summary

    • $203/SF
    • 113 Days On Market

    Current Estimated Value $330,436

    Last Listing Agent Nishta Gupta Samson Properties

    118 Edenton Ln, Denton, MD 21629
    • 16911 Heritage Hills Ln, Henderson, MD 21640
      16911 Heritage Hills Ln, Henderson, MD 21640
      16911 Heritage Hills Ln, Henderson, MD 21640
      /43

      Est $499,042 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,428 Sq Ft

      16911 Heritage Hills Ln, Henderson, MD 21640

      16911 Heritage Hills Ln, Henderson, MD 21640
  • 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
    • 310 W Central Ave, Federalsburg, MD 21632
      310 W Central Ave, Federalsburg, MD 21632
      310 W Central Ave, Federalsburg, MD 21632
      /26

      Est $272,329 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,359 Sq Ft

      310 W Central Ave, Federalsburg, MD 21632

      310 W Central Ave, Federalsburg, MD 21632
  • 1904 Blue Heron Dr, Denton, MD 21629
    1904 Blue Heron Dr, Denton, MD 21629
    1904 Blue Heron Dr, 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 $263,405

    Last Listing Agent Ralph Harvey ListWithFreedom.com

    1904 Blue Heron Dr, Denton, MD 21629
    • 4 N Maple Ave, Ridgely, MD 21660
      4 N Maple Ave, Ridgely, MD 21660
      4 N Maple Ave, Ridgely, MD 21660
      /18

      Est $267,513 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 864 Sq Ft

      4 N Maple Ave, Ridgely, MD 21660

      4 N Maple Ave, Ridgely, MD 21660
  • 306 Sunrise Ave, Ridgely, MD 21660
    306 Sunrise Ave, Ridgely, MD 21660
    306 Sunrise Ave, Ridgely, MD 21660
    /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 $289,134

    Last Listing Agent Wanda Hampton Clark & Co Realty, LLC

    306 Sunrise Ave, Ridgely, MD 21660

Showing Results 481 - 520, Page 13 of 18

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