15,623

Caroline County, MD Homes

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  • /38

    $479,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,747 Sq Ft

    8605 Hickory Place, Denton, MD 21629

    Beautiful Colonial Farmhouse nestled on a wooded lot at the end of a cul-de-sac private lane. This 4 bedroom, 2.5 bath home has been meticulously maintained and features a traditional floor plan with a large kitchen/breakfast area, large family room with vaulted ceilings and a gas fireplace, separate dining room, living room/office. Second floor includes a primary suite with large bathroom with a

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    8605 Hickory Place, Denton, MD 21629
  • /16

    Starting at $465 Per Month

    • 1 - 3 Beds

    101 Quinn Cir, Denton, MD 21629

    Riverwoods at Denton is an affordable housing community featuring newly renovated existing apartments and 36 apartment homes. All of the apartments offer the latest Green energy-saving and conserving features and include a modern kitchen, with abundant cabinetry as well as dishwasher, disposal and microwave. Handicap accessible apartments are also available.Riverwoods at Denton features a 1,500

    Riverwoods at Denton

    101 Quinn Cir, Denton, MD 21629
  • /24

    $160,000

    Sold Apr 02, 2026

    315 Cool Spring Rd, Marydel, MD 21649

    • 3 Beds
    • 1.5 Baths
    • 1,524 Sq Ft
    • Built 1920

    Last Sold Summary

    • 5% Below List Price
    • $105/SF
    • 19 Days On Market

    Current Estimated Value $161,428

    Last Listing Agent John Fifer Brokers Realty Group, LLC

    315 Cool Spring Rd, Marydel, MD 21649
    • /53

      Est $557,904

      Not Listed For Sale

      25833 Spring Branch Dr, Greensboro, MD 21639

      • 4 Beds
      • 2.5 Baths
      • 2,960 Sq Ft
      • Built 2004
      25833 Spring Branch Dr, Greensboro, MD 21639

      Last Sold Summary

      • 111 Days On Market

      Last Listing Agent Dan Foster Long & Foster Real Estate, Inc.

  • /28

    $595,000

    • 3 Beds
    • 3.5 Baths
    • 3,276 Sq Ft

    23730 Henry Rd, Ridgely, MD 21660

    Beautiful Craftsman Cape Cod on quiet country road in Caroline County. This 3,200 sq ft home was built in 2023 and offers an open floor plan with all the amenities...large family room with vaulted ceilings, private office, large kitchen with white cabinets, farm sink, SS appliances, separate butler's pantry, and separate laundry room, first floor primary with walk-in closet, high-end primary

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    23730 Henry Rd, Ridgely, MD 21660
  • /2

    Starting at $670 Per Month

    • 1 - 4 Beds

    500 High St, Denton, MD 21629

    Riverview Gardens

    500 High St, Denton, MD 21629
  • /5

    $1,020,000

    Sold Sep 26, 2025

    0 River Rd Unit MDCM2006210, Ridgely, MD 21660

    • Land
    • 134.85 Acres
    • $7,564 per Acre

    Last Sold Summary

    • 9 Days On Market

    Last Listing Agent Nick Haiduk Thyme Real Estate Co LLC

    0 River Rd Unit MDCM2006210, Ridgely, MD 21660
    • /31

      Est $264,755

      Not Listed For Sale

      213 S 6th St, Denton, MD 21629

      • 3 Beds
      • 1 Bath
      • 1,120 Sq Ft
      • Built 1983
      213 S 6th St, Denton, MD 21629

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Christian Schou TTR Sotheby's International Realty

  • /87

    $1,550,000

    • 5 Beds
    • 4.5 Baths
    • 4,853 Sq Ft

    322 S 2nd St, Denton, MD 21629

    Wake up to sunrise on the Choptank River and wind down with some of the most stunning sunsets on the Eastern Shore — with Ospreys, Eagles, Herons, and an abundance of wildlife as your daily backdrop. This stunning 4,853 sq ft waterfront estate sits on 2.44 acres with 268 feet of private river frontage, putting you right on the water and just steps from the best of historic downtown Denton. Built

    Agent Photo

    Elizabeth Osborn

    Coldwell Banker Realty

    322 S 2nd St, Denton, MD 21629
  • /11

    $1,495 Per Month

    • 2 Beds
    • 1 Bath
    • House for Rent

    202 N 6th St Unit 102, Denton, MD 21629

    Very Nice 2 Bedroom 1 bath only 3 Years old! Large Kitchen /Famiy Room Combo. Downstairs unit. Front Porch. Off Street parking. Separate Laundry Room.Walking distance to Shopping & Restaurants. Available Now.

    Kathleen Brenton Brenton Realty Group

    202 N 6th St Unit 102, Denton, MD 21629
  • /37

    $325,000

    Sold May 12, 2026

    11305 River Rd, Ridgely, MD 21660

    • 3 Beds
    • 1 Bath
    • 1,533 Sq Ft
    • Built 1972

    Last Sold Summary

    • 13% Below List Price
    • $212/SF
    • 87 Days On Market

    Current Estimated Value $325,046

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

    11305 River Rd, Ridgely, MD 21660
    • /29

      Est $221,192

      Not Listed For Sale

      306 Railroad Ave, Goldsboro, MD 21636

      • 3 Beds
      • 1 Bath
      • 1,568 Sq Ft
      • Built 1900
      306 Railroad Ave, Goldsboro, MD 21636

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Brett Schrader Taylor Properties

  • /63

    $399,000

    $9K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft

    7392 Todds Wharf Rd, Preston, MD 21655

    This very comfortable rancher has ramps at rear of home for accessibility for those not able to walk up steps very well. Roomy kitchen and open floor plan allows large gatherings to enjoy the roominess. Large counter seats 4 comfortably. Dining area for full-size table and chairs. Working stone wood-burning fireplace is great for use to heat home all winter or just on-call use when you want the

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    7392 Todds Wharf Rd, Preston, MD 21655
  • /13

    $1,800 Per Month

    • 3 Beds
    • 1.5 Baths
    • House for Rent

    203 S 2nd St, Denton, MD 21629

    Charming 3 bedroom, 1 1/2 bath Victorian house in the town of Denton. Foyer, living room, 1/2 bath, kitchen, laundry and dining room downstairs. All bedrooms and full bath upstairs. Wood floors throughout with slate floor in kitchen and carpet in 2 of the bedrooms. Screened porch, nice size yard with off-street parking and shed. Propane heat, central air. Appliances included. Tenant takes care of

    203 S 2nd St, Denton, MD 21629
  • /80

    $710,000

    Sold Mar 20, 2026

    15184 Jarrell Rd, Goldsboro, MD 21636

    • 6 Beds
    • 4.5 Baths
    • 5,000 Sq Ft
    • Built 1995

    Last Sold Summary

    • $142/SF
    • 494 Days On Market

    Current Estimated Value $725,366

    Last Listing Agent Leslie Fulford Mann & Sons, Inc.

    15184 Jarrell Rd, Goldsboro, MD 21636
    • /6

      Est $1,094,657

      Not Listed For Sale

      21171 Wood Wharf Ln, Preston, MD 21655

      • 3 Beds
      • 2.5 Baths
      • 1,872 Sq Ft
      • Built 1900
      21171 Wood Wharf Ln, Preston, MD 21655

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Coard Benson Benson & Mangold, LLC

  • /63

    $1,500,000

    Under Contract
    • 3 Beds
    • 3.5 Baths
    • 3,958 Sq Ft

    7347 Harmony Rd, Preston, MD 21655

    Income-producing poultry farm situated on approximately 38.17 acres in desirable Caroline County, featuring four state-of-the-art “Tier 3” tunnel poultry houses with a combined capacity of approximately 110,000 broiler chickens. Built in 1993, the four 40’ x 500’ houses are equipped with Rotem Platinum+ controllers, Shore Time computerized controls, alarm systems, recirculation cooling pads, 6”

    Agent Photo

    Damon Brockenberry

    Keller Williams Preferred Properties

    7347 Harmony Rd, Preston, MD 21655
  • /10

    $1,150 Per Month

    • 1 Bed
    • 1 Bath
    • 738 Sq Ft
    • House for Rent

    101 W Sunset Ave, Greensboro, MD 21639

    Cute one bedroom apt in the heart of downtown! Upstairs unit has all appliances including washer and dryer. Spacious kitchen with breakfast bar. Open living room to kitchen. Central air. Town water and sewer.

    Marcia Rostien Long & Foster Real Estate, Inc.

    101 W Sunset Ave, Greensboro, MD 21639
  • /21

    $391,000

    Sold Oct 29, 2025

    11225 Shane Cir, Ridgely, MD 21660

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 2017

    Last Sold Summary

    • $261/SF
    • 4 Days On Market

    Current Estimated Value $389,648

    Last Listing Agent Kathleen Brenton Brenton Realty Group

    11225 Shane Cir, Ridgely, MD 21660
    • /26

      Est $472,338

      Not Listed For Sale

      11490 Maplewood Dr, Ridgely, MD 21660

      • 4 Beds
      • 3 Baths
      • 2,346 Sq Ft
      • Built 2019
      11490 Maplewood Dr, Ridgely, MD 21660

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

  • /8

    $125,000

    • Land
    • 2.31 Acres
    • $54,113 per Acre

    0 Burnt Mill Rd Unit MDCM2005294, Ridgely, MD 21660

    Welcome to the Oasis neighborhood, a serene and picturesque enclave nestled in the charming town of Ridgely, MD. This prestigious 2.3-acre wooded lot on Burnt Mill Road presents a unique opportunity to craft your dream home amidst nature's splendor. With its perc approval, this lot is primed and ready for you to bring your architectural vision to life. As you enter the Oasis, you're greeted by a

    Agent Photo

    Gretchen Wichlinski

    Compass

    0 Burnt Mill Rd Unit MDCM2005294, Ridgely, MD 21660
  • /24

    $1,300 Per Month

    • 2 Beds
    • 1 Bath
    • 1,388 Sq Ft
    • House for Rent

    152 E Belle St, Ridgely, MD 21660

    Historic home in the out skirts of Ridgely, MD. Down stairs features new vinyl flooring throughout. Kitchen, bathroom, laundry room, dining room, living room and office/bedroom. Up stairs has a great room with 2 bedrooms/storage area. Propane heat, central hair. Choptank Fiber provides internet. Choptank Electric provides power. Credit score of 650 or higher required. Apply at

    152 E Belle St, Ridgely, MD 21660
  • /32

    $227,500

    Sold Aug 20, 2025

    1303 Blue Heron Dr, Denton, MD 21629

    • 3 Beds
    • 2.5 Baths
    • 1,816 Sq Ft
    • Built 2004

    Last Sold Summary

    • $125/SF
    • 27 Days On Market

    Current Estimated Value $234,430

    Last Listing Agent Justin Pokrywka Taylor Properties

    1303 Blue Heron Dr, Denton, MD 21629
    • /23

      Est $336,541

      Not Listed For Sale

      323 Mallard Dr, Greensboro, MD 21639

      • 3 Beds
      • 2.5 Baths
      • 1,632 Sq Ft
      • Built 2023
      323 Mallard Dr, Greensboro, MD 21639

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Juliet Wells Coldwell Banker Chesapeake Real Estate Company

  • /16

    $234,900

    Under Contract
    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    163 Riverwalk Terrace, Federalsburg, MD 21632

    This end unit has units on the left side but no units on the right side, offering more quietness and privacy. This beauty has comfort and "home" written all over. Featuring 3 nice-sized bedrooms; a convenient half-bath is located on first level. The kitchen is very well designed with lots of beautiful cabinets and countertops. Bright open floor plan offering nice flow for the kitchen, living

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    163 Riverwalk Terrace, Federalsburg, MD 21632
  • /22

    $2,000 Per Month

    • 4 Beds
    • 2 Baths
    • 2,688 Sq Ft
    • House for Rent

    22721 Marsh Creek Rd, Preston, MD 21655

    VERY NICE 4 BEDROOM 2 BATH COUNTRY HOME NEAR PRESTON. A FOUR SQUARE HOUSE WITH BUILT-IN CORNER CABINETS, SOME KNOTTY PINE WALLS AND SHELVING, WOOD FLOORS AND A FULL WIDTH FRONT PORCH. QUIET AND SECLUDED WITH LARGE SHADE TREES AND FARM FIELDS ALL AROUND FOR A BEAUTIFUL, COMFORTING VIEW.

    Ed Quidas Long & Foster Real Estate, Inc.

    22721 Marsh Creek Rd, Preston, MD 21655
  • /8

    $78,000

    Sold Jun 16, 2026

    lot 4 River Rd, Greensboro, MD 21639

    • Land
    • 5.62 Acres
    • $13,879 per Acre

    Last Sold Summary

    • 13% Below List Price
    • 5 Days On Market

    Last Listing Agent Marcia Rostien Long & Foster Real Estate, Inc.

    lot 4 River Rd, Greensboro, MD 21639
    • /30

      Est $315,877

      Not Listed For Sale

      319 Mallard Dr, Greensboro, MD 21639

      • 3 Beds
      • 2 Baths
      • 1,468 Sq Ft
      • Built 2023
      319 Mallard Dr, Greensboro, MD 21639

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Juliet Wells Coldwell Banker Chesapeake Real Estate Company

  • /9

    $125,000

    Under Contract
    • Land
    • 2.54 Acres
    • $49,213 per Acre

    0 Burnt Mill Rd Unit MDCM2005298, Ridgely, MD 21660

    Welcome to the Oasis neighborhood, a serene and picturesque enclave nestled in the charming town of Ridgely, MD. This prestigious 2.5-acre wooded lot on Burnt Mill Road presents a unique opportunity to craft your dream home amidst nature's splendor. With its perc approval, this lot is primed and ready for you to bring your architectural vision to life. As you enter the Oasis, you're greeted by a

    Agent Photo

    Gretchen Wichlinski

    Compass

    0 Burnt Mill Rd Unit MDCM2005298, Ridgely, MD 21660
  • /8

    $89,900

    Sold Jun 16, 2026

    lot 2 E Sunset Ave, Greensboro, MD 21639

    • Land
    • 5.64 Acres
    • $15,940 per Acre

    Last Sold Summary

    • 5 Days On Market

    Last Listing Agent Marcia Rostien Long & Foster Real Estate, Inc.

    lot 2 E Sunset Ave, Greensboro, MD 21639
    • /23

      Est $298,736

      Not Listed For Sale

      105 Elmor Ct, Greensboro, MD 21639

      • 3 Beds
      • 2 Baths
      • 1,192 Sq Ft
      • Built 2013
      105 Elmor Ct, Greensboro, MD 21639

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent BJ Kilby Eastern Shore Real Estate, LLC

  • /24

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    11139 Central Ave, Ridgely, MD 21660

    Welcome to 11139 Central Avenue, where the tranquility of country living meets the convenience of a prime Caroline County location. Nestled on one acre outside Ridgely, this updated 3 bed 2 bath rancher offers space, functionality, and modern updates. The open concept layout is great for entertaining, while the 30 x 50 shop shines for those who need serious workspace, storage, or just a big

    Agent Photo

    BJ Kilby

    Eastern Shore Real Estate, LLC

    11139 Central Ave, Ridgely, MD 21660
  • /5

    $305,000

    Sold Jun 25, 2026

    3390 Jefferson Pond Rd, Federalsburg, MD 21632

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2026

    Last Sold Summary

    • $227/SF
    • 6 Days On Market

    Last Listing Agent Amy Herr Keller Williams Realty

    3390 Jefferson Pond Rd, Federalsburg, MD 21632
    • /66

      Est $335,951

      Not Listed For Sale

      25970 Three Bridges Rd, Federalsburg, MD 21632

      • 4 Beds
      • 2 Baths
      • 1,844 Sq Ft
      • Built 1996
      25970 Three Bridges Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 71 Days On Market

      Last Listing Agent John Tarpley Schwartz Realty, Inc.

  • /14

    $124,900

    $55K PRICE DROP
    • Land
    • 10.39 Acres
    • $12,021 per Acre

    PARCEL 91 Cool Spring Rd, Marydel, MD 21649

    Ready for you to build your new home! This beautiful lot is already perc approved for a 3-bedroom home. A barnominium is permitted to be built on this property and would be wonderful on this location. The woods are a great habitat for deer and turkey and other wildlife. This lovely lot is all ready for the new owner to apply for home construction as the buyer has had the survey completed with the

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    PARCEL 91 Cool Spring Rd, Marydel, MD 21649
  • /7

    $240,000

    Sold Aug 29, 2025

    4539 Houston Branch Rd, Federalsburg, MD 21632

    • 2 Beds
    • 1 Bath
    • 736 Sq Ft
    • Built 1949

    Last Sold Summary

    • $326/SF
    • 0 Days On Market

    Current Estimated Value $243,892

    Last Listing Agent Barbara Nichols Results Realty Inc.

    4539 Houston Branch Rd, Federalsburg, MD 21632
    • /19

      Est $222,373

      Not Listed For Sale

      206 Maple Ave, Ridgely, MD 21660

      • 2 Beds
      • 1.5 Baths
      • 1,248 Sq Ft
      • Built 1890
      206 Maple Ave, Ridgely, MD 21660

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Karen Clark Clark & Co Realty, LLC

  • /68

    $329,900

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,436 Sq Ft

    110 N School St, Greensboro, MD 21639

    Price to purchase has been lowered to help you afford top quality at a fantastic price. Come see this beautiful home. Pride of ownership is shown from top to bottom in this magnificent rancher! This custom-built home was completed in June 2025 and is like new. The owner took much pride in everything he installed/built and makes this home very desirable. The nine-foot (9') ceilings add the feeling

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    110 N School St, Greensboro, MD 21639
  • /38

    $225,000

    Sold Sep 19, 2025

    12194 Knife Box Rd, Greensboro, MD 21639

    • 2 Beds
    • 2 Baths
    • 1,488 Sq Ft
    • Built 1900

    Last Sold Summary

    • $151/SF
    • 38 Days On Market

    Current Estimated Value $255,536

    Last Listing Agent Dustin Parker The Parker Group

    12194 Knife Box Rd, Greensboro, MD 21639
    • /5

      Est $508,673

      Not Listed For Sale

      24776 Tribbett Cir, Ridgely, MD 21660

      • Built 2025
      24776 Tribbett Cir, Ridgely, MD 21660

      Last Sold Summary

      • 261 Days On Market

      Last Listing Agent Stephan Strothe Washington Fine Properties, LLC

Showing Results 1 - 40, Page 1 of 18

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