15,671

Caroline County, MD Homes

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  • 24749 Woods Dr, Denton, MD 21629
    24749 Woods Dr, Denton, MD 21629
    24749 Woods Dr, Denton, MD 21629
    /42

    $485,000 Open House 1/03

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

    24749 Woods Dr, Denton, MD 21629

    Beautifully maintained 4 bedroom, 2.5 bath Colonial set on a spacious lot just minutes from Denton and the newly opened Caroline Country Club. This inviting home features a comfortable, flowing layout featuring a gas fireplace, perfect for relaxing evenings or gatherings. The kitchen is conveniently located right off the main living area. The space showcases granite counter tops, stainless steel

    Peter Stark Benson & Mangold, LLC

    24749 Woods Dr, Denton, MD 21629
  • 305 Morning Glory Dr, Denton, MD 21629
    305 Morning Glory Dr, Denton, MD 21629
    305 Morning Glory Dr, Denton, MD 21629
    /55

    $390,000 Sold Jun 20, 2025

    305 Morning Glory Dr, Denton, MD 21629

    • 4 Beds
    • 2.5 Baths
    • 2,646 Sq Ft
    • Built 2021

    Last Sold Summary

    • $147/SF
    • 37 Days On Market

    Current Estimated Value $424,876

    Last Listing Agent Cornelia Fallon Coldwell Banker Waterman Realty

    305 Morning Glory Dr, Denton, MD 21629
    • 1238 Painted Fern Rd, Denton, MD 21629
      1238 Painted Fern Rd, Denton, MD 21629
      1238 Painted Fern Rd, Denton, MD 21629
      /19

      Est $388,522 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,492 Sq Ft

      1238 Painted Fern Rd, Denton, MD 21629

      1238 Painted Fern Rd, Denton, MD 21629
  • 517 W Sunset Ave, Greensboro, MD 21639
    517 W Sunset Ave, Greensboro, MD 21639
    517 W Sunset Ave, Greensboro, MD 21639
    /4

    $345,000

    • Studio
    • 2,260 Sq Ft

    517 W Sunset Ave, Greensboro, MD 21639

    Three unit apartment building. Two 1bedroom apartments, one 2 bedroom. Fully leased with positive income to support expense and debt service

    Randy Staats Benson & Mangold, LLC

    517 W Sunset Ave, Greensboro, MD 21639
  • 6074 Newton Rd, Preston, MD 21655
    6074 Newton Rd, Preston, MD 21655
    6074 Newton Rd, Preston, MD 21655
    /64

    $565,000 Sold Oct 08, 2025

    6074 Newton Rd, Preston, MD 21655

    • 3 Beds
    • 2.5 Baths
    • 2,060 Sq Ft
    • Built 1993

    Last Sold Summary

    • $274/SF
    • 64 Days On Market

    Last Listing Agent James Bent Benson & Mangold, LLC

    6074 Newton Rd, Preston, MD 21655
    • 1306 Blue Heron Dr, Denton, MD 21629
      1306 Blue Heron Dr, Denton, MD 21629
      1306 Blue Heron Dr, Denton, MD 21629
      /45

      Est $249,166 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,620 Sq Ft

      1306 Blue Heron Dr, Denton, MD 21629

      1306 Blue Heron Dr, Denton, MD 21629
  • 318 Carter Ave, Denton, MD 21629
    318 Carter Ave, Denton, MD 21629
    318 Carter Ave, Denton, MD 21629
    /38

    $214,900

    • 2 Beds
    • 2 Baths
    • 606 Sq Ft

    318 Carter Ave, Denton, MD 21629

    This charming bungalow, fully renovated in 2020 and move-in ready, blends modern comfort with timeless appeal. Behind the classic covered front porch, an open layout offers two bedrooms and two full bathrooms on a single level. The living and kitchen area features a vaulted ceiling with recessed lighting, enhancing the sense of space and adding a clean, modern feel to this efficient floor

    Georgi Chauvin Benson & Mangold, LLC

    318 Carter Ave, Denton, MD 21629
  • Lot 7 Harmony Woods Dr, Preston, MD 21655
    Lot 7 Harmony Woods Dr, Preston, MD 21655
    /2

    $53,100 Sold Jan 10, 2025

    Lot 7 Harmony Woods Dr, Preston, MD 21655

    • Land
    • 1.15 Acres
    • $46,174 per Acre

    Last Sold Summary

    • 244 Days On Market

    Last Listing Agent Barbara Nichols Results Realty Inc.

    Lot 7 Harmony Woods Dr, Preston, MD 21655
    • 203 Wood Duck Dr, Greensboro, MD 21639
      203 Wood Duck Dr, Greensboro, MD 21639
      203 Wood Duck Dr, Greensboro, MD 21639
      /54

      Est $350,983 Not Listed For Sale

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

      203 Wood Duck Dr, Greensboro, MD 21639

      203 Wood Duck Dr, Greensboro, MD 21639
  • 106 Briarwood Cir, Denton, MD 21629
    106 Briarwood Cir, Denton, MD 21629
    106 Briarwood Cir, Denton, MD 21629
    /60

    $399,900 Under Contract

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

    106 Briarwood Cir, Denton, MD 21629

    New Construction Feel—Without the Wait!Welcome to the highly sought-after Sandy Meadows community, where this beautifully maintained home—just 4 years young—is move-in ready and waiting for its next owners. Offering over 2,500 sq. ft. of living space, this property is designed for comfort, functionality, and effortless entertaining. Step inside to a spacious open-concept living room and

    Stephanie Smith Douglas Realty, LLC

    106 Briarwood Cir, Denton, MD 21629
  • 201 S 2nd St, Denton, MD 21629
    201 S 2nd St, Denton, MD 21629
    201 S 2nd St, Denton, MD 21629
    /32

    $250,000 Sold Feb 26, 2025

    201 S 2nd St, Denton, MD 21629

    • 4 Beds
    • 2 Baths
    • 1,536 Sq Ft
    • Built 1885

    Last Sold Summary

    • $163/SF
    • 135 Days On Market

    Current Estimated Value $271,225

    Last Listing Agent Darlene Winegardner RE/MAX Executive

    201 S 2nd St, Denton, MD 21629
    • 322 Maple Ave, Federalsburg, MD 21632
      322 Maple Ave, Federalsburg, MD 21632
      322 Maple Ave, Federalsburg, MD 21632
      /20

      Est $227,438 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,812 Sq Ft

      322 Maple Ave, Federalsburg, MD 21632

      322 Maple Ave, Federalsburg, MD 21632
  • 3 Sunrise Ave, Ridgely, MD 21660
    3 Sunrise Ave, Ridgely, MD 21660
    3 Sunrise Ave, Ridgely, MD 21660
    /22

    $369,000

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

    3 Sunrise Ave, Ridgely, MD 21660

    ***New Construction - TO BE BUILT with estimated completion of winter/early spring 2026. Photos are of model previously built.*** This modern "Farmhouse" Rancher is thoughtfully designed and constructed by the reputable Lomaxx Custom Homes, offering the perfect combination of style, functionality, and comfort. This beautiful home features 3 bedrooms, 2 full bathrooms, and an inviting open-concept

    Amy Betts Coldwell Banker Realty

    3 Sunrise Ave, Ridgely, MD 21660
  • 128 Mill St, Greensboro, MD 21639
    128 Mill St, Greensboro, MD 21639
    128 Mill St, Greensboro, MD 21639
    /7

    $265,000 Sold Mar 05, 2025

    128 Mill St, Greensboro, MD 21639

    • 3 Beds
    • 1 Bath
    • 1,890 Sq Ft
    • Built 1981

    Last Sold Summary

    • $140/SF
    • 18 Days On Market

    Current Estimated Value $296,877

    Last Listing Agent Phill Whitby Long & Foster Real Estate, Inc.

    128 Mill St, Greensboro, MD 21639
    • 12171 River Rd, Ridgely, MD 21660
      12171 River Rd, Ridgely, MD 21660
      12171 River Rd, Ridgely, MD 21660
      /26

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,568 Sq Ft

      12171 River Rd, Ridgely, MD 21660

      12171 River Rd, Ridgely, MD 21660
  • 25361 Calvert Dr, Greensboro, MD 21639
    25361 Calvert Dr, Greensboro, MD 21639
    25361 Calvert Dr, Greensboro, MD 21639
    /70

    $324,500 Under Contract

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

    25361 Calvert Dr, Greensboro, MD 21639

    Water privileged, privacy and lots of space, over 1,800 sqft with 3 bedrooms and 2 full baths. You won t want to miss this one. Lots of space for entertaining inside and out. Inside you will find new floors in kitchen and laundry room, recently purchased stainless appliances, fresh painted walls, updated bathroom, large open floor plan, and a sun room overlooking the large, fenced-in yard.

    Chris Rosendale CR Realty

    25361 Calvert Dr, Greensboro, MD 21639
  • 508 W Sunset Ave, Greensboro, MD 21639
    508 W Sunset Ave, Greensboro, MD 21639
    508 W Sunset Ave, Greensboro, MD 21639
    /18

    $250,000 Sold Oct 14, 2025

    508 W Sunset Ave, Greensboro, MD 21639

    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft
    • Built 1975

    Last Sold Summary

    • $223/SF
    • 8 Days On Market

    Last Listing Agent Erene Katris Coldwell Banker Realty

    508 W Sunset Ave, Greensboro, MD 21639
    • 1622 Blue Heron Dr, Denton, MD 21629
      1622 Blue Heron Dr, Denton, MD 21629
      1622 Blue Heron Dr, Denton, MD 21629
      /30

      Est $276,660 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 2,244 Sq Ft

      1622 Blue Heron Dr, Denton, MD 21629

      1622 Blue Heron Dr, Denton, MD 21629
  • 8 Sunrise Ave, Ridgely, MD 21660
    8 Sunrise Ave, Ridgely, MD 21660
    8 Sunrise Ave, Ridgely, MD 21660
    /23

    $384,900 Pending

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

    8 Sunrise Ave, Ridgely, MD 21660

    This modern "Farmhouse" Rancher is thoughtfully designed and constructed by the reputable Lomaxx Custom Homes, offering the perfect combination of style, functionality, and comfort. This beautiful home features 3 bedrooms, 2 full bathrooms, and an inviting open-concept layout—ideal for both everyday living and entertaining. High-end finishes come standard, including luxury vinyl plank flooring, a

    Amy Betts Coldwell Banker Realty

    8 Sunrise Ave, Ridgely, MD 21660
  • 27381 Greenwood Rd, Denton, MD 21629
    27381 Greenwood Rd, Denton, MD 21629
    27381 Greenwood Rd, Denton, MD 21629
    /21

    $309,000 Sold Nov 03, 2025

    27381 Greenwood Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,922 Sq Ft
    • Built 1900

    Last Sold Summary

    • $161/SF
    • 66 Days On Market

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

    27381 Greenwood Rd, Denton, MD 21629
    • 326 E Central Ave, Federalsburg, MD 21632
      326 E Central Ave, Federalsburg, MD 21632
      326 E Central Ave, Federalsburg, MD 21632
      /3

      Est $58,333 Not Listed For Sale

      326 E Central Ave, Federalsburg, MD 21632

      326 E Central Ave, Federalsburg, MD 21632
  • 1 Sunrise Ave, Ridgely, MD 21660
    1 Sunrise Ave, Ridgely, MD 21660
    1 Sunrise Ave, Ridgely, MD 21660
    /28

    $399,000 New Construction

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

    1 Sunrise Ave, Ridgely, MD 21660

    To Be Built, but you are able to do showings at the model home that is pictured NOW with renderings of the actual projected home in the first two photos. As you can see, Lomaxx Custom Homes puts effort into every detail. 1 Sunrise Ave will feature 4 bedrooms and 2.5 beautifully designed bathrooms. From the moment you step onto the brick steps of the front porch you'll notice the charm of the

    Crystal Smith RE/MAX Executive

    1 Sunrise Ave, Ridgely, MD 21660
  • 115 Riverwalk Terrace, Federalsburg, MD 21632
    115 Riverwalk Terrace, Federalsburg, MD 21632
    115 Riverwalk Terrace, Federalsburg, MD 21632
    /28

    $219,990 Sold Mar 24, 2025

    115 Riverwalk Terrace, Federalsburg, MD 21632

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

    Last Sold Summary

    • $161/SF
    • 66 Days On Market

    Current Estimated Value $237,526

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

    115 Riverwalk Terrace, Federalsburg, MD 21632
    • 8556 Andersontown Rd, Denton, MD 21629
      8556 Andersontown Rd, Denton, MD 21629
      8556 Andersontown Rd, Denton, MD 21629
      /57

      Est $449,141 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,870 Sq Ft

      8556 Andersontown Rd, Denton, MD 21629

      8556 Andersontown Rd, Denton, MD 21629
  • 1005 Market St, Denton, MD 21629
    1005 Market St, Denton, MD 21629
    1005 Market St, Denton, MD 21629
    /3

    $135,000

    • Land
    • 0.69 Acre
    • $195,652 per Acre

    1005 Market St, Denton, MD 21629

    A Rare Opportunity to Purchase a General Commercial Lot located in Denton off the High Visibility Corners of Market & Gay St. A Multitude of permissible uses. Water and Sewer hook ups are available for additional fee. There are not any structures on this cleared .69 ac lot. A wonderful Opportunity for the Entrepreneur with a Vision....Hurry to snag this one...

    Barbara Beaudet Brenton Realty Group

    1005 Market St, Denton, MD 21629
  • 208 Bloomingdale Ave, Federalsburg, MD 21632
    208 Bloomingdale Ave, Federalsburg, MD 21632
    208 Bloomingdale Ave, Federalsburg, MD 21632
    /99

    $420,000 Sold Aug 29, 2025

    208 Bloomingdale Ave, Federalsburg, MD 21632

    • 3 Beds
    • 2.5 Baths
    • 3,734 Sq Ft
    • Built 1930

    Last Sold Summary

    • $112/SF
    • 16 Days On Market

    Current Estimated Value $432,875

    Last Listing Agent Blaine Williamson McClain-Williamson Realty, LLC

    208 Bloomingdale Ave, Federalsburg, MD 21632
    • 2 Greenridge Ave, Ridgely, MD 21660
      2 Greenridge Ave, Ridgely, MD 21660
      2 Greenridge Ave, Ridgely, MD 21660
      /12

      Est $326,116 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,560 Sq Ft

      2 Greenridge Ave, Ridgely, MD 21660

      2 Greenridge Ave, Ridgely, MD 21660
  • 131 Hobbs St, Greensboro, MD 21639

    $292,990 New Construction

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

    131 Hobbs St, Greensboro, MD 21639

    Welcome to 131 Hobbs Street, a new home soon to be under construction in our newest community, Kinnamon Meadows in Greensboro, MD. 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

    D.R. Horton Builder
    131 Hobbs St, Greensboro, MD 21639
  • 326 N Main St, Federalsburg, MD 21632
    326 N Main St, Federalsburg, MD 21632
    326 N Main St, Federalsburg, MD 21632
    /31

    $227,000 Sold Jun 09, 2025

    326 N Main St, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,592 Sq Ft
    • Built 1915

    Last Sold Summary

    • $143/SF
    • 188 Days On Market

    Current Estimated Value $238,362

    Last Listing Agent Billy Mister Keller Williams Realty

    326 N Main St, Federalsburg, MD 21632
    • 1104 Osprey Ln, Denton, MD 21629
      1104 Osprey Ln, Denton, MD 21629
      1104 Osprey Ln, Denton, MD 21629
      /42

      Est $413,552 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,590 Sq Ft

      1104 Osprey Ln, Denton, MD 21629

      1104 Osprey Ln, Denton, MD 21629
  • 26355 Marydel Rd, Marydel, MD 21649
    26355 Marydel Rd, Marydel, MD 21649
    26355 Marydel Rd, Marydel, MD 21649
    /4

    $155,000

    • 1 Bed
    • 1 Bath
    • 512 Sq Ft

    26355 Marydel Rd, Marydel, MD 21649

    House is of little to no value, existing well and septic. This house includes an additional parcel of 7 acres, tax id, 0601012428 for a total of 7.27 acres. Property being SOLD AS IS.

    George Thompson Long & Foster Real Estate, Inc.

    26355 Marydel Rd, Marydel, MD 21649
  • 6939 Reliance Rd, Federalsburg, MD 21632
    6939 Reliance Rd, Federalsburg, MD 21632
    6939 Reliance Rd, Federalsburg, MD 21632
    /53

    $320,000 Sold Apr 28, 2025

    6939 Reliance Rd, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • Built 1981

    Last Sold Summary

    • $205/SF
    • 132 Days On Market

    Current Estimated Value $325,436

    Last Listing Agent Sharon Fisher RE/MAX Advantage Realty

    6939 Reliance Rd, Federalsburg, MD 21632
    • 11401 Greensboro Rd, Denton, MD 21629
      11401 Greensboro Rd, Denton, MD 21629
      11401 Greensboro Rd, Denton, MD 21629
      /19

      Est $307,538 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,036 Sq Ft

      11401 Greensboro Rd, Denton, MD 21629

      11401 Greensboro Rd, Denton, MD 21629
  • 7929 Laurel Ln, Denton, MD 21629
    7929 Laurel Ln, Denton, MD 21629
    7929 Laurel Ln, Denton, MD 21629
    /50

    $699,000

    • 4 Beds
    • 2.5 Baths
    • 2,243 Sq Ft

    7929 Laurel Ln, Denton, MD 21629

    Discover this custom-built 4-bedroom, 2.5-bath contemporary home set on nearly 4 acres in a desirable water-access community. Residents enjoy a private beach and picnic area, while the property itself offers exceptional outdoor living with a spacious fenced-in inground pool, custom greenhouse, and raised garden beds. Tax record is incorrect, actual above grade square footage is 2243 sq ft.! The

    Linda Moore Long & Foster Real Estate, Inc.

    7929 Laurel Ln, Denton, MD 21629
  • 21959 Main St, Hillsboro, MD 21641
    21959 Main St, Hillsboro, MD 21641
    21959 Main St, Hillsboro, MD 21641
    /28

    $285,000 Sold May 09, 2025

    21959 Main St, Hillsboro, MD 21641

    • 4 Beds
    • 2 Baths
    • 2,168 Sq Ft
    • Built 1885

    Last Sold Summary

    • $131/SF
    • 9 Days On Market

    Current Estimated Value $317,179

    Last Listing Agent Jimmy White Long & Foster Real Estate, Inc.

    21959 Main St, Hillsboro, MD 21641
    • 1115 Market St, Denton, MD 21629
      1115 Market St, Denton, MD 21629
      1115 Market St, Denton, MD 21629
      /17

      Est $242,962 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 788 Sq Ft

      1115 Market St, Denton, MD 21629

      1115 Market St, Denton, MD 21629
  • 24276 Asbury Dr, Denton, MD 21629
    24276 Asbury Dr, Denton, MD 21629
    24276 Asbury Dr, Denton, MD 21629
    /50

    $642,900

    • 4 Beds
    • 2.5 Baths
    • 2,920 Sq Ft

    24276 Asbury Dr, Denton, MD 21629

    Nestled in the shadows of the Choptank River is a meticulously maintained home in the water-privileged neighborhood of Asbury. Expansive lot sizes give you the privacy needed within a walkable neighborhood. Sit in your rocker with a cocktail while enjoying the dream turned into a reality of a wrap-around porch. A large rear screened-in porch to watch the local wildlife opens onto extensive

    Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    24276 Asbury Dr, Denton, MD 21629
  • 1206 Trice Meadows Cir, Denton, MD 21629
    1206 Trice Meadows Cir, Denton, MD 21629
    1206 Trice Meadows Cir, Denton, MD 21629
    /19

    $325,000 Sold Aug 08, 2025

    1206 Trice Meadows Cir, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,470 Sq Ft
    • Built 2018

    Last Sold Summary

    • $221/SF
    • 86 Days On Market

    Current Estimated Value $344,412

    Last Listing Agent Bonnie Johnson Keller Williams Realty

    1206 Trice Meadows Cir, Denton, MD 21629
    • 7881 Dyer Rd, Denton, MD 21629
      7881 Dyer Rd, Denton, MD 21629
      7881 Dyer Rd, Denton, MD 21629
      /33

      Est $306,117 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,961 Sq Ft

      7881 Dyer Rd, Denton, MD 21629

      7881 Dyer Rd, Denton, MD 21629
  • 306 Bernard Ave, Greensboro, MD 21639
    306 Bernard Ave, Greensboro, MD 21639
    306 Bernard Ave, Greensboro, MD 21639
    /9

    $198,000

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft

    306 Bernard Ave, Greensboro, MD 21639

    Step into this delightful home that perfectly blends comfort with convenience. The open-concept living and kitchen area creates an inviting space for relaxing or entertaining, complete with effortless flow and natural light. With two well-sized bedrooms and a full bathroom, it's ideal for small households or anyone seeking a cozy oasis. From the kitchen, step out onto the oversized back deck—your

    Amanda Morgan Brenton Realty Group

    306 Bernard Ave, Greensboro, MD 21639

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