15,577

Caroline County, MD Homes

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  • /37

    $319,000

    $6K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,232 Sq Ft

    2792 Meadowbrook Rd, Federalsburg, MD 21632

    Space, flexibility, and outdoor living come together at 2792 Meadowbrook Road! This spacious 5-bedroom, 2.5-bath split-level home sits on a beautiful .46-acre lot.The upper level features three bedrooms, including a primary bedroom with its own private bath. The living room offers an open feel and an opportunity to create an even more unique space with the potential for an upper balcony. The

    Agent Photo

    Kate Lewis

    Keller Williams Realty

    2792 Meadowbrook Rd, Federalsburg, MD 21632
  • /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
    • /43

      Not Listed For Sale

      25266 Smith Landing Rd, Denton, MD 21629

      • 2 Beds
      • 1 Bath
      • 1,256 Sq Ft
      • Built 1953
      25266 Smith Landing Rd, Denton, MD 21629

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Megan Rosendale Rosendale Realty

  • /3

    $55,000

    • Land
    • 4 Acres
    • $13,750 per Acre

    0 Houston Branch Rd Unit MDCM2007816, Federalsburg, MD 21632

    Secluded 4 Acre lot bordering the Idylwild Nature Preserve offering excellent hunting, biking, hiking and fishing. According to the county there is a well on site. Zoned R1. Property recently acquired through tax sale foreclosure. Note that the lot is only accessible at the end of Willin Ln off of Houston Branch Rd. Do NOT go to the property without prior authorization. Please call listing agent

    Agent Photo

    Joe Howerton

    Taylor Properties

    0 Houston Branch Rd Unit MDCM2007816, Federalsburg, MD 21632
  • /11

    $1,250

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    211 Greenridge Rd Unit B, Federalsburg, MD 21632

    211 Greenridge Rd Unit B, Federalsburg, MD 21632
  • /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
    • /21

      Est $422,240

      Not Listed For Sale

      24711 Pealiquor Rd, Denton, MD 21629

      • 4 Beds
      • 2 Baths
      • 2,040 Sq Ft
      • Built 1996
      24711 Pealiquor Rd, Denton, MD 21629

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Eddie Matthews Benson & Mangold, LLC

  • /43

    $345,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,832 Sq Ft

    307 Sydney Ln, Denton, MD 21629

    Welcome home to this well maintained Cape Cod located close to everything!! Open floor plan.. Kitchen has granite countertops, stainless steel appliances and ample space!! Garage has built in cabinetry and finished floors!! Large Family Room opens to Light drenched sunroom that leads to a maintenance free deck with a retractable awning that looks over a private backyard with a stream in the back

    Agent Photo

    Tanya Lewis

    Cummings & Co. Realtors

    307 Sydney Ln, Denton, MD 21629
  • /2

    $1,450

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • Condo for Rent

    5 Maryland Ave Unit 5d, Ridgely, MD 21660

    5 Maryland Ave Unit 5d, Ridgely, MD 21660
  • /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
    • /71

      Est $465,043

      Not Listed For Sale

      122 Lister Ln, Ridgely, MD 21660

      • 4 Beds
      • 3 Baths
      • 4,304 Sq Ft
      • Built 2006
      122 Lister Ln, Ridgely, MD 21660

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Chris Rosendale CR Realty

  • /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, with few lots remaining. This prestigious 2.3-acre wooded lot (Lot 8) 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

    Agent Photo

    Gretchen Wichlinski

    Compass

    0 Burnt Mill Rd Unit MDCM2005294, Ridgely, MD 21660
  • /25

    $1,295 Per Month

    • 1 Bed
    • 1 Bath
    • House for Rent

    113 Davis Ln, Federalsburg, MD 21632

    Shane Snoots MD & DE Group Property Management

    113 Davis Ln, Federalsburg, MD 21632
  • /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
    • /26

      Est $121,440

      Not Listed For Sale

      201 Denton Rd, Federalsburg, MD 21632

      • 3 Beds
      • 1 Bath
      • 1,051 Sq Ft
      • Built 1955
      201 Denton Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Alex Fox Allfirst Realty, Inc.

  • /18

    $289,000

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

    18974 Harman Rd, Marydel, MD 21649

    Welcome to affordable, clean and peaceful livingl! Situated on a corner lot, this clean and well-maintained home offers numerous recent improvements. Interior updates include fresh paint, a new ceiling fan, luxury vinyl plank flooring in two bedrooms and the hallway, and an updated full bathroom featuring a tub-and-shower combination. The kitchen includes a new dishwasher, and the home also

    Agent Photo

    Kristina Hyland

    Coldwell Banker Chesapeake Real Estate Company

    18974 Harman Rd, Marydel, MD 21649
  • /16

    $2,450 Per Month

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

    6 N Maryland Ave, Ridgely, MD 21660

    Welcome to this nearly 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,

    6 N Maryland Ave, 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 $389,648

    Last Listing Agent Kathleen Brenton Brenton Realty Group

    11225 Shane Cir, Ridgely, MD 21660
    • /15

      Est $202,468

      Not Listed For Sale

      307 W Central Ave, Federalsburg, MD 21632

      • 3 Beds
      • 1 Bath
      • 1,340 Sq Ft
      • Built 1935
      307 W Central Ave, Federalsburg, MD 21632

      Last Sold Summary

      • 105 Days On Market

      Last Listing Agent Mary Mabry Mabry Real Estate LLC

  • /39

    $228,000

    $7K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    163 Riverwalk Terrace, Federalsburg, MD 21632

    This lovely end-unit condo has units on the left side but no units on the right side, offering more quietness and privacy. This beauty has comfort of "home" written all over. Featuring 3 good-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 ease of flow for the

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    163 Riverwalk Terrace, Federalsburg, MD 21632
  • /16

    $2,450 Per Month

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

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

    Welcome to this nearly 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 6B, 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
    • /38

      Est $237,667

      Not Listed For Sale

      12194 Knife Box Rd, Greensboro, MD 21639

      • 2 Beds
      • 2 Baths
      • 1,488 Sq Ft
      • Built 1900
      12194 Knife Box Rd, Greensboro, MD 21639

      Last Sold Summary

      • 38 Days On Market

      Last Listing Agent Dustin Parker The Parker Group

  • /94

    $380,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,904 Sq Ft

    28440 Bloomery Rd, Federalsburg, MD 21632

    If you've been searching for a property that offers acreage, privacy, and plenty of room to grow, this is the one you've been waiting for! Nestled on 3.80 wooded acres, this ranch-style home offers approximately 1,904 square feet of comfortable living space, featuring 3 bedrooms, 2 full baths, and two versatile bonus rooms that can easily serve as a home office, hobby room, playroom, guest space,

    Agent Photo

    Sean Steward

    Century 21 Home Team Realty

    28440 Bloomery Rd, Federalsburg, MD 21632
  • /9

    $1,550 Per Month

    • 3 Beds
    • 1 Bath
    • Condo for Rent

    211 S 6th St Unit A, Denton, MD 21629

    Enjoy comfortable living in this 3 bedroom, 1 bath home conveniently located at 211 A N. 6th Street, Denton, Maryland. Electric baseboard heat, window a/c units, wood flooring. Situated close to doctors' offices, restaurants, shopping, and other local amenities, this property offers both convenience and accessibility. Rental Requirements: No pets Minimum credit score of 650

    211 S 6th St Unit A, Denton, MD 21629
  • /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
    • /3

      Not Listed For Sale

      Lot 3 Clark Canning House Rd, Federalsburg, MD 21632

      Lot 3 Clark Canning House Rd, Federalsburg, MD 21632

      Last Sold Summary

      • 160 Days On Market

      Last Listing Agent Mickey Hayward Sunset Properties

  • /14

    $114,900

    $65K PRICE DROP Under Contract
    • Land
    • 10.39 Acres
    • $11,059 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
  • /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, electric stove, fridge, dish washer and microwave. Spacious kitchen with breakfast bar. Open living room to kitchen. Central heat and air. Town water and sewer is paid by the landlord.No Pets, No Smoking. Landlord is looking for a 12 month or longer lease First months rent & security

    Marcia Rostien Long & Foster Real Estate, Inc.

    101 W Sunset Ave, Greensboro, MD 21639
  • /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
    • /54

      Est $534,980

      Not Listed For Sale

      11575 Maplewood Dr, Ridgely, MD 21660

      • 4 Beds
      • 3 Baths
      • 1,900 Sq Ft
      • Built 2020
      11575 Maplewood Dr, Ridgely, MD 21660

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

  • /2

    $229,000

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft

    305 Caroline Ave, Ridgely, MD 21660

    Affordable 2-Bedroom Home in the Heart of Ridgely. Welcome to 305 Caroline Avenue, a charming and budget-friendly two bedroom, one bath that's conveniently located. It's a livable home that's ready for your updates, giving you a great opportunity to build equity. Enjoy small town living with easy drives to Denton, Easton, and Annapolis via major roadways. Located within a community known for its

    Agent Photo

    BJ Kilby

    Eastern Shore Real Estate, LLC

    305 Caroline Ave, Ridgely, MD 21660
  • /16

    $1,300 Per Month

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

    8444 Hickman Rd, Denton, MD 21629

    Unique 1 bedroom house in small town. Newer heat pump, propane stove/dryer. Has propane wall heater in enclosed porch. $1300 per month, $1300 security deposit. Credit Score of 650 or higher required, sufficient income and no criminal background.

    8444 Hickman Rd, Denton, MD 21629
  • /11

    $165,000

    Sold Sep 11, 2026

    23480 Brunkhorst Rd, Preston, MD 21655

    • 2 Beds
    • 1 Bath
    • 737 Sq Ft
    • Built 1950

    Last Sold Summary

    • $224/SF
    • 7 Days On Market

    Current Estimated Value $200,995

    Last Listing Agent Andrew Beaven Wright Real Estate

    23480 Brunkhorst Rd, Preston, MD 21655
    • /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

  • /41

    $309,900

    $40K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,436 Sq Ft

    110 N School St, Greensboro, MD 21639

    Why wait for new construction? Completed in 2025, this custom-built, move-in ready rancher offers 1,436 square feet of thoughtfully designed, single-level living--with no HOA. The bright, open-concept living, dining, and kitchen area features nine-foot ceilings, solid hardwood flooring and recessed LED lighting. The kitchen is finished with granite countertops, all-wood cabinetry, Samsung

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    110 N School St, Greensboro, MD 21639
  • /19

    $2,250 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft
    • Townhouse for Rent

    131 Riverwalk Terrace, Federalsburg, MD 21632

    End Unit 3 Bedroom 2.5 bath townhome in the heart of Federalsburg. The lower level is bright and spacious with a dining area, kitchen with stainless steel appliances and great room that leads to Deck overlooking the river. The upper levels features 3 bedrooms, 2 full baths and in unit washer and dryer. This Riverside community features nature trails along Marshyhope Creek and over the walking

    Theresa Deminne Samson Properties

    131 Riverwalk Terrace, Federalsburg, MD 21632
  • /28

    $405,000

    Sold Aug 26, 2026

    25214 Smith Landing Rd, Denton, MD 21629

    • 3 Beds
    • 2 Baths
    • 1,740 Sq Ft
    • Built 1960

    Last Sold Summary

    • $233/SF
    • 18 Days On Market

    Current Estimated Value $368,425

    Last Listing Agent John Fifer Brokers Realty Group, LLC

    25214 Smith Landing Rd, 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

Showing Results 1 - 40, Page 1 of 18

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