15,675

Caroline County, MD Homes

Section Image Section Image
  • /102

    $1,395,000

    • 4 Beds
    • 3.5 Baths
    • 3,356 Sq Ft

    23296 Wilder Way, Denton, MD 21629

    Right out of HGTV! Custom Built in 2020, this 3,350+/- sq ft one-level home offers an abundance of amenities including high ceilings, 4 bedrooms, 3.5 Baths, large open floorplan with huge gourmet kitchen with quartz/ss appliances, separate pantry, family room with stacked stone gas fireplace. The Primary Bedroom is located at one end of the house and includes a large bath with double vanity,

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (410) 376-8486

    23296 Wilder Way, Denton, MD 21629
  • /16

    $465 - $1,290 per month

    Riverwoods at Denton

    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

    101 Quinn Cir, 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
    • /25

      Est $356,209 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,512 Sq Ft

      407 Maryland Ave, Ridgely, MD 21660

      407 Maryland Ave, Ridgely, MD 21660
  • /8

    $129,000

    • Land
    • 3.51 Acres
    • $36,752 per Acre

    0 Burnt Mill Rd Unit MDCM2005292, Ridgely, MD 21660

    Welcome to the Oasis neighborhood, a serene and picturesque enclave nestled in the charming town of Ridgely, MD. This prestigious 3.5-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

    (410) 705-7988

    0 Burnt Mill Rd Unit MDCM2005292, Ridgely, MD 21660
  • /3

    $2,450 per month

    • 4 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Townhouse for Rent

    6 N Maryland Ave Unit 6A / 6B, Ridgely, MD 21660

    Welcome to this stunning New Construction 4-bedroom, 2 full-bath duplex located in Ridgely, MD. Thoughtfully designed and developed by Lomaxx Custom Homes with modern living in mind, this spacious home offers a functional layout, quality finishes, and the convenience. The main level features one bedroom and a full bathroom, perfect for guests, a home office, or flexible living needs. Upstairs,

    Romont Fletcher Keller Williams Flagship

    6 N Maryland Ave Unit 6A / 6B, Ridgely, MD 21660
  • /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 $389,165

    Last Listing Agent Kathleen Brenton Brenton Realty Group

    11225 Shane Cir, Ridgely, MD 21660
    • /112

      Est $1,514,981 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,864 Sq Ft

      18870 Crown Stone Rd, Marydel, MD 21649

      18870 Crown Stone Rd, Marydel, MD 21649
  • /9

    $125,000

    • 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

    (667) 297-6243

    0 Burnt Mill Rd Unit MDCM2005298, Ridgely, MD 21660
  • /10

    $1,165 - $1,415 per month

    Sunset Hargraves Ridgely

    1 - 3 Beds

    502 Sunset Blvd, Ridgely, MD 21660

    Welcome to Sunset Hargraves Ridgely, where newly renovated affordable apartment homes meet the charm of Maryland’s Eastern Shore. Located in the heart of Ridgely, our spacious 1, 2, and 3-bedroom apartments feature brand-new kitchens, energy-efficient appliances, luxury vinyl plank flooring, new windows, and more. Community-wide upgrades include new roofing, gutters, and refreshed breezeways,

    502 Sunset Blvd, Ridgely, MD 21660
  • /24

    $199,000 Sold Jun 05, 2025

    311 S 4th St, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,304 Sq Ft
    • Built 1910

    Last Sold Summary

    • $153/SF
    • 13 Days On Market

    Current Estimated Value $229,960

    Last Listing Agent Kathleen Brenton Brenton Realty Group

    311 S 4th St, Denton, MD 21629
    • /27

      Est $898,850 Not Listed For Sale

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

      12805 Kibler Rd, Greensboro, MD 21639

      12805 Kibler Rd, Greensboro, MD 21639
  • /10

    $620,000

    • Studio
    • 3,600 Sq Ft

    310 Main St, Marydel, MD 21649

    Great Apartment Building investment opportunity, updated, and ready to go! The building includes three 2-bedroom, 1-bath units and one 3-bedroom, 1-bath unit — all with private entrances and separately metered utilities. A furnished office space adds additional potential for on-site management or rental income.Recent upgrades include: New well (less than a year old) with a 20-year warranty,

    Agent Photo

    Sharon Daugherty

    Keller Williams Realty Delmarva

    (410) 881-8824

    310 Main St, Marydel, MD 21649
  • /8

    $1,975 per month

    • 3 Beds
    • 2.5 Baths
    • Townhouse for Rent

    163 Riverwalk Terrace, Federalsburg, MD 21632

    Brand New Spacious end-unit townhouse. This community is located along Marshyhope Creek with trails to the river, marina and park. First floor features an open floor plan with kitchen, dining, family room and half bath. Luxury vinyl plank floors, stainless steel appliances and granite countertops. All three bedrooms and two full baths are located on the second floor as well as the laundry.

    Andrew Beaven Wright Real Estate

    163 Riverwalk Terrace, Federalsburg, MD 21632
  • /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 $238,107

    Last Listing Agent Justin Pokrywka Taylor Properties

    1303 Blue Heron Dr, Denton, MD 21629
    • /18

      Est $220,628 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,376 Sq Ft

      26220 Auction Rd, Federalsburg, MD 21632

      26220 Auction Rd, Federalsburg, MD 21632
  • /8

    $125,000

    • Land
    • 2.4 Acres
    • $52,083 per Acre

    0 Burnt Mill Rd Unit MDCM2005300, Ridgely, MD 21660

    Welcome to the Oasis neighborhood, a serene and picturesque enclave nestled in the charming town of Ridgely, MD. This prestigious 2.4-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

    (667) 868-0827

    0 Burnt Mill Rd Unit MDCM2005300, Ridgely, MD 21660
  • /2

    $670 - $1,454 per month

    Riverview Gardens

    1 - 4 Beds

    500 High St, Denton, MD 21629

    500 High St, Denton, MD 21629
  • /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 $246,035

    Last Listing Agent Barbara Nichols Results Realty Inc.

    4539 Houston Branch Rd, Federalsburg, MD 21632
    • /48

      Est $297,177 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 3,076 Sq Ft

      213 N Main St, Federalsburg, MD 21632

      213 N Main St, Federalsburg, MD 21632
  • /7

    $129,000

    • Land
    • 3.33 Acres
    • $38,739 per Acre

    0 Burnt Mill Rd Unit MDCM2005290, Ridgely, MD 21660

    Welcome to the Oasis neighborhood, a serene and picturesque enclave nestled in the charming town of Ridgely, MD. This prestigious 3.3-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

    (667) 249-9508

    0 Burnt Mill Rd Unit MDCM2005290, Ridgely, MD 21660
  • /17

    $2,500 per month

    • 3 Beds
    • 2 Baths
    • 8,096 Sq Ft
    • House for Rent

    15329 Church Ln, Goldsboro, MD 21636

    Welcome to this clean 3-bedroom 2-bath home that offers fenced in backyard and a large front porch for relaxing. Large kitchen and huge Primary with access to the backyard. Large soaking tube and separate shower. Walk-in closet. No Pets or Smoking.

    Roger Boyce Chesapeake Real Estate Associates, LLC

    15329 Church Ln, Goldsboro, MD 21636
  • /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 $240,434

    Last Listing Agent Dustin Parker The Parker Group

    12194 Knife Box Rd, Greensboro, MD 21639
    • /20

      Est $196,264 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,008 Sq Ft

      313 Holt St, Federalsburg, MD 21632

      313 Holt St, Federalsburg, MD 21632
  • /65

    $599,000

    • 4 Beds
    • 2.5 Baths
    • 2,475 Sq Ft

    17753 Marvel Rd, Marydel, MD 21649

    Stylish 2021 Colonial on 4.41 acres — space, serenity & seaside access just minutes away!Stop scrolling — this one checks every box. Settled on a private, unrestricted 4.41-acre canvas, this modern 4-bed, 3-bath Colonial delivers peace, light, and room to roam without sacrificing convenience. A thoughtful open plan marries everyday comfort with effortless entertaining — ideal whether you’re

    Agent Photo

    Petra Quinn

    Realty Navigator

    (667) 297-6065

    17753 Marvel Rd, Marydel, MD 21649
  • /20

    $2,700 per month

    • 3 Beds
    • 2.5 Baths
    • 1,520 Sq Ft
    • House for Rent

    3995 American Corner Rd, Federalsburg, MD 21632

    Property Id: 2326406Step into timeless charm with modern comfort at 3995 American Corner Rd in Federalsburg…a beautifully refreshed 1890 farmhouse set on 2.6 peaceful acres that offers space, character, and endless possibilities.This 3-bedroom, 2.5-bath single-family home features 1,520 square feet of inviting living space, thoughtfully updated while preserving its historic soul.

    3995 American Corner Rd, Federalsburg, MD 21632
  • /2

    $380,000 Sold Jan 23, 2026

    0 River Rd Unit MDCM2005824, Ridgely, MD 21660

    • Land
    • 44.74 Acres
    • $8,494 per Acre

    Last Sold Summary

    • 17% Below List Price
    • 203 Days On Market

    Last Listing Agent Andrew Beaven Wright Real Estate

    0 River Rd Unit MDCM2005824, Ridgely, MD 21660
    • /4

      Not Listed For Sale

      0 Idlewild Rd, Federalsburg, MD 21632

      0 Idlewild Rd, Federalsburg, MD 21632
  • /73

    $749,900

    • 3 Beds
    • 2 Baths
    • 2,676 Sq Ft

    12820 Porters Landing Rd, Greensboro, MD 21639

    The Ultimate Secluded Waterfront Retreat! Privately positioned along the Choptank River, this 12.43 acre waterfront property is surrounded by mature trees, open sky, and abundant natural beauty. The mostly wooded landscape offers privacy and tranquility, creating a peaceful escape that feels worlds away yet remains connected to the charm of Maryland’s Eastern Shore. Outdoor amenities elevate the

    Agent Photo

    Penny Hollis

    Keller Williams Select Realtors of Annapolis

    (410) 834-0596

    12820 Porters Landing Rd, Greensboro, MD 21639
  • /17

    $1,550 per month

    • 2 Beds
    • 1 Bath
    • 1,742 Sq Ft
    • House for Rent

    108 W Sunset Ave, Greensboro, MD 21639

    Charming older home with hardwood floors and plenty of space. Separate large living room and dining room. Eat in space in kitchen. Kitchen has exit to mud room, that also leads to back yard. Very spacious laundry room with shelving for pantry and storage. The home has 3 rooms upstairs that could all be bedrooms; one does not have a closet. There is a cellar with workbench and HVAC unit. Nice

    Cindy Jacobs Maryland Residential Management Co

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

    $274,900 Sold Feb 19, 2025

    14185 Drapers Mill Rd, Greensboro, MD 21639

    • 4 Beds
    • 1 Bath
    • 1,352 Sq Ft
    • Built 1910

    Last Sold Summary

    • $203/SF
    • 101 Days On Market

    Current Estimated Value $296,427

    Last Listing Agent Kathleen Brenton Brenton Realty Group

    14185 Drapers Mill Rd, Greensboro, MD 21639
    • /27

      Est $230,010 Not Listed For Sale

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

      103 Riverwalk Terrace, Federalsburg, MD 21632

      103 Riverwalk Terrace, Federalsburg, MD 21632
  • /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

    (667) 282-1883

    0 Burnt Mill Rd Unit MDCM2005294, Ridgely, MD 21660
  • /12

    $1,275 per month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    10 Maryland Ave Unit 1, Ridgely, MD 21660

    Welcome to this unique, studio-style apartment located in the heart of the charming town of Ridgely, MD. This rental offers a perfect blend of comfort, practicality, and town charm. Among the property's key features is a spacious open layout that makes the 600 square foot space feel expansive and comfortable. Large windows welcome an abundance of natural light, enhancing the town views and

    10 Maryland Ave Unit 1, Ridgely, MD 21660
  • /19

    $25,000 Sold Nov 24, 2025

    310 Park Ave, Federalsburg, MD 21632

    • 1 Bed
    • 1.5 Baths
    • 812 Sq Ft
    • Built 1904

    Last Sold Summary

    • $31/SF
    • 8 Days On Market

    Last Listing Agent Daniel Demers Sell Your Home Services

    310 Park Ave, Federalsburg, MD 21632
    • /28

      Not Listed For Sale

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

      114 Riverwalk Terrace, Federalsburg, MD 21632

      114 Riverwalk Terrace, Federalsburg, MD 21632
  • /71

    $445,000

    • 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
  • /20

    $1,350 per month

    • 3 Beds
    • 1 Bath
    • 1,140 Sq Ft
    • House for Rent

    3530 Houston Branch Rd, Federalsburg, MD 21632

    Nice 3 Bedroom 1 bath rental. Tenants must apply online through RentSpree. Pets on a “case by case” scenario, No smoking, 600 min credit score, minimum income requirements, and will need to provide recent pay stubs for income verification. First months, last months, and security deposit due at singing of lease.

    Blaine Williamson McClain-Williamson Realty, LLC

    3530 Houston Branch Rd, Federalsburg, MD 21632
  • /23

    $360,000 Sold May 07, 2025

    435 Main St, Goldsboro, MD 21636

    • 2 Beds
    • 1 Bath
    • 1,680 Sq Ft
    • Built 1940

    Last Sold Summary

    • $214/SF
    • 16 Days On Market

    Last Listing Agent Elizabeth Tryon Coldwell Banker Realty

    435 Main St, Goldsboro, MD 21636
    • /27

      Est $228,060 Not Listed For Sale

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

      104 Riverwalk Terrace, Federalsburg, MD 21632

      104 Riverwalk Terrace, Federalsburg, MD 21632

Showing Results 1 - 40, Page 1 of 18

How to Buy a Home How to Finance a Home How to Sell a Home