15,674

Caroline County, MD Homes

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    • /124

      Est $758,183 Not Listed For Sale

      • 4 Beds
      • 4 Baths
      • 3,921 Sq Ft

      24754 Pealiquor Rd, Denton, MD 21629

      24754 Pealiquor Rd, Denton, MD 21629
  • /89

    $2,995,000

    • 4 Beds
    • 4.5 Baths
    • 6,520 Sq Ft

    28219 Bridgeville Rd, Federalsburg, MD 21632

    Welcome to a rare opportunity to own a premier 105+/- acre agricultural estate combining modern comfort, income-producing farmland, and outstanding infrastructure. Ideally situated in a peaceful rural setting, this remarkable property features approximately 70± acres of fully irrigated, tillable land—perfect for high-yield row crops or specialty farming. At the heart of the farm sits a stunning

    Jim Corson Benson & Mangold, LLC

    28219 Bridgeville Rd, Federalsburg, MD 21632
  • /26

    $375,000 Sold Jul 08, 2025

    • 1,648 Sq Ft
    • $228/SF
    • 197 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1973

    22965 Tuckahoe Springs Dr, Denton, MD 21629

    New and Improved! Welcome to Tuckahoe Springs, where easy living meets the Eastern Shore! This ranch style home has so much to offer. Step into the spacious living area open to the recently renovated kitchen/dining room featuring rustic cabinetry aplenty and granite countertops. Off the main living area, there is a smaller sitting room and laundry area. Down the hall you will find two

    Amanda Morgan Brenton Realty Group

    22965 Tuckahoe Springs Dr, Denton, MD 21629
    • /26

      Est $394,762 Not Listed For Sale

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

      25698 Caroline St, Greensboro, MD 21639

      25698 Caroline St, Greensboro, MD 21639
  • /13

    $435,000

    • Studio
    • 7,260 Sq Ft

    25548 Hill Rd, Greensboro, MD 21639

    HUGE POTENTIAL. Residential/commercial property combined. 4 residential units available. Two units occupied with annual leases (one at $700.00 and the other at $725.00). Two units vacant (one needs some work and the other needs extensive work. All 4 units are Certified Lead Free. Large main section is gutted and has excellent potential for apartments, etc. Buyer and or Buyer's agent to

    Rosa Tyre Kelark Real Estate

    25548 Hill Rd, Greensboro, MD 21639
  • /28

    $275,000 Sold Jul 08, 2025

    • 1,008 Sq Ft
    • $273/SF
    • 215 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1992

    104 Sunset Blvd, Ridgely, MD 21660

    This beautiful home is waiting for you! Pretty much everything is new! Just move right in! The outside is all maintenance free, with new 100 year Metal roof, new vinyl clad windows, new Amish made front and back doors, vinyl siding and new sidewalks. Inside you will find the updated kitchen with new fridge & counter tops, freshly painted cabinetry, center island with dish washer and large

    Marcia Rostien Long & Foster Real Estate, Inc.

    104 Sunset Blvd, Ridgely, MD 21660
    • /34

      Est $338,725 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,232 Sq Ft

      8157 Arch Dr, Denton, MD 21629

      8157 Arch Dr, Denton, MD 21629
  • /50

    $432,000

    • 4 Beds
    • 2.5 Baths
    • 2,124 Sq Ft

    26674 Bentley Place, Henderson, MD 21640

    Price reduction of $10,000! This beauty was built in 2004, current owners moved in 2006 added the in-ground salt water pool and property sits on 1.30 acres!! This large 4 bedroom and 2.5 bath home is just the perfect size. Beautiful hard wood floors throughout the first floor, with an open floor plan. Fireplace on first floor runs on propane, which seller does not use or have a propane

    Sally Fricke RE/MAX Solutions

    26674 Bentley Place, Henderson, MD 21640
  • /71

    $429,000 Sold Jul 07, 2025

    • 1,648 Sq Ft
    • $260/SF
    • 29 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1984

    25612 Auction Rd, Federalsburg, MD 21632

    Nothing but wide open spaces at 25612 Auction Rd! This 3 bedroom 1 full bath rancher sits on 1.26 acres with a beautiful country setting just on the Denton line. Featuring a paver patio, bonus room, pellet stove, LVP flooring, updated kitchen with granite countertops, attached oversized garage. The 40x50 pole building with 12 ft doors has space for your camper, boat, 4 wheelers & then some!

    Megan Rosendale Rosendale Realty

    25612 Auction Rd, Federalsburg, MD 21632
    • /8

      Est $173,247 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 845 Sq Ft

      108 Roe St, Greensboro, MD 21639

      108 Roe St, Greensboro, MD 21639
  • /9

    $99,000

    • Land
    • 3.05 Acres
    • $32,459 per Acre

    10440 Burrsville Branch Rd, Denton, MD 21629

    3+ ACRES PARTLY WOODED AND BACKS TO FARMLAND. NOT LOCATED IN A COMMUNITY AND NO HOA. (PLAT REFLECTS 3.235 +- ACRES, WHILE SDAT REFELCTS 3.05+- ACRES) PROPERTY IS IMPROVED WITH A 2 STORY HOME THAT WAS BUILT IN 1900 . THIS IS A TEAR DOWN OR PERHAPS POSSIBLY A FIXER UPPER. ***** DO NOT ENTER RESIDENCE***** THERE IS ALSO AN EXISTING WELL AND SEPTIC ON THE PROPERTY. HOUSE, WELL AND SEPTIC ARE

    Deborah Callahan Benson & Mangold, LLC

    10440 Burrsville Branch Rd, Denton, MD 21629
  • /28

    $299,000 Sold Jul 07, 2025

    • 1,320 Sq Ft
    • $227/SF
    • 84 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1956

    607 N Main St, Greensboro, MD 21639

    RARE FIND!! In-Town lot with 1.4 Acres! Home Features 3 Bedrooms 1 Full Bath, Nice Living Room, Dining Room, Kitchen, Finished Sun Room. Full Unfinished Basement. (High Ceilings and Very Dry) Attic has Blown to Foam insulation for very economical heat and cool. Oversize Attached Two-Car Garage- Detached 1.5 Car Garage to include wood stove and work bench! Barn with 4 stalls .Makes for Tons of

    Kathleen Brenton Brenton Realty Group

    607 N Main St, Greensboro, MD 21639
    • /52

      Est $410,348 Not Listed For Sale

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

      1709 Cattail Commons Way, Denton, MD 21629

      1709 Cattail Commons Way, Denton, MD 21629
  • /20

    $230,000

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    218 E Sunset Ave, Greensboro, MD 21639

    Welcome to 218 E Main St Greensboro, MD. This home offers 3 bedrooms and 1 bath. Home has a large, dethatched garage and off-street parking. Located next to the public boat ramp, with easy access to local shopping and Delaware tax free shopping. This home is located in a flood zone and is being sold as is. Sellers are offering $5,000 in closing assistance with acceptable offer!

    Dawn Williams Berkshire Hathaway Homeservice Homesale Realty

    218 E Sunset Ave, Greensboro, MD 21639
  • /2

    $399,000 Sold Jul 03, 2025

    • 1,750 Sq Ft
    • $228/SF
    • 42 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2025

    5549 Harmony Woods Dr, Preston, MD 21655

    Welcome to Harmony Woods right outside of Preston, MD ! This beautiful new construction rancher offers 3 bedrooms, 2 full bathrooms, and stylish modern finishes throughout Step inside to discover an open-concept living space, perfect for entertaining or cozy evenings at home. The kitchen is a true centerpiece, featuring granite countertops, stainless steel appliances, and plenty of cabinet space.

    Shirley Coulbourne Coldwell Banker Realty

    5549 Harmony Woods Dr, Preston, MD 21655
    • /18

      Est $340,357 Not Listed For Sale

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

      13585 Dahlia Ct, Greensboro, MD 21639

      13585 Dahlia Ct, Greensboro, MD 21639
  • /64

    $625,000

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

    6074 Newton Rd, Preston, MD 21655

    Welcome to 6074 Newton Road Preston, MD - Winding gravel drive invites you to 5.82 acres, a Nature Lover's Paradise of woods and open spaces on Crowberry Creek just off the Choptank River. Enjoy the stone walkway heading to the front door and enter the foyer of this 2,060 Sq. Ft Home. Enjoy as you walk past a more formal living area, past the totally updated Country Kitchen and into the

    James Bent Benson & Mangold, LLC

    6074 Newton Rd, Preston, MD 21655
  • /2

    $274,490 Sold Jun 30, 2025

    • 1,182 Sq Ft
    • $232/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2025

    108 Parkland Rd, Greensboro, MD 21639

    Explore 108 Parkland Road, a new home in the quaint Kinnamon Meadows community of Greensboro, MD. The Curtis is a 1,282 square foot, cottage-style ranch home with three bedrooms and two bathrooms. As you enter the home through the front porch, this thoughtfully designed home has a grand open concept living area that leads into the spacious kitchen. To the right, a long, main hallway

    Kathleen Cassidy D R Horton Realty of Virginia LLC

    108 Parkland Rd, Greensboro, MD 21639
    • /43

      Est $314,253 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,952 Sq Ft

      505 Teal Cir, Greensboro, MD 21639

      505 Teal Cir, Greensboro, MD 21639
  • /61

    $799,000

    • 4 Beds
    • 3.5 Baths
    • 3,819 Sq Ft

    26943 Fueller Dr, Marydel, MD 21649

    Serene 18-Acre Retreat with Endless Potential!Welcome to your private escape, nearly 18 acres of open space, wooded serenity, and room to bring your vision to life. Whether you're dreaming of a homestead, hobby farm, or multi-use property, this one-of-a-kind opportunity offers versatility, space, and freedom.The home boasts over 3,800 sq ft of thoughtfully designed living space,

    Crystal Smith RE/MAX Executive

    26943 Fueller Dr, Marydel, MD 21649
  • /36

    $375,000 Sold Jun 30, 2025

    • 1,344 Sq Ft
    • $279/SF
    • 82 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1999

    11145 Branch Ct, Denton, MD 21629

    Come see this 3-bedroom, 2-bath house tucked away with 2 acres of land and no HOA. This home includes a large oversized 3-bay detached garage which includes LED lights, speakers, and overhead storage. You will be greeted by a nice-sized living room and a large open kitchen when you enter the home. Relax on your front porch or back screened-in porch. The 2 acres is a flat and open area with

    Sean O'Connor Coldwell Banker Realty

    11145 Branch Ct, Denton, MD 21629
    • /28

      Est $187,761 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,272 Sq Ft

      316 N Main St, Greensboro, MD 21639

      316 N Main St, Greensboro, MD 21639
  • /10

    $249,000

    • Land
    • 0.23 Acre
    • $1,082,609 per Acre

    520 S 5th Ave, Denton, MD 21629

    LET’S MAKE A DEAL***INVEST IN A PRIME MULTI USE SITE * DESIRABLE LOCATIONS * BUYERS CHOICEDEVELOP NOW? Or HOLD AND LET TIME INCREASE YPUR PROFIT OPPORTUNITY.... FOUR 10,000 SQ FT ADJOINING LOTS IN A GREAT IN TOWN SETTING S DUPLEX. IS ONE OF SEVERAL PERMITTED USES SO EASILY to build total 8 UNITS. Office, Shop or Studio with 2nd floor Residential for a Live Work

    Phil Riordan Meredith Fine Properties

    520 S 5th Ave, Denton, MD 21629
  • /41

    $440,000 Sold Jun 30, 2025

    • 1,976 Sq Ft
    • $223/SF
    • 25 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1978

    24706 Pealiquor Rd, Denton, MD 21629

    Truly move in ready and anything but cookie cutter, this charming Cape Cod offers a unique living experience that is hard to find. With 4 bedrooms and 2 baths, This home sits on a serene .69 acre wooded lot, offering peace, privacy, and a bird lover's paradise. Inside a beautiful masonry gas fireplace serves as a cozy focal point. The home has been impeccably maintained and well-loved with

    Terri Murray RE/MAX Executive

    24706 Pealiquor Rd, Denton, MD 21629
    • /51

      Est $334,855 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 936 Sq Ft

      25720 Burrsville Rd, Denton, MD 21629

      25720 Burrsville Rd, Denton, MD 21629
  • /34

    $440,000

    • 4 Beds
    • 2.5 Baths
    • 3,096 Sq Ft

    1207 Painted Fern Rd, Denton, MD 21629

    Welcome to 1207 Painted Fern Road — a beautifully maintained and thoughtfully upgraded home nestled in the heart of Denton. This spacious residence offers the perfect blend of modern comfort, functional design, and serene natural surroundings.Step inside to a dramatic two-story foyer that sets an elegant tone for the rest of the home. To the right, a private office provides an ideal space

    Trudie Colvin Coldwell Banker Realty

    1207 Painted Fern Rd, Denton, MD 21629
  • /28

    $240,990 Sold Jun 30, 2025

    • 1,365 Sq Ft
    • $177/SF
    • 26 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2025

    151 Riverwalk Terrace, Federalsburg, MD 21632

    Relax on your back deck and enjoy picturesque views of the Marshyhope Creek at 151 Riverwalk Terrace in Federalsburg, MD, in the scenic Riverwalk Terrace community. The Jefferson is an open-concept 1,365 square foot two-story end-of-unit townhome with three bedrooms, two and a half bathrooms, and on-street parking. The first floor is spacious with a large, thoughtfully designed kitchen

    Kathleen Cassidy D R Horton Realty of Virginia LLC

    151 Riverwalk Terrace, Federalsburg, MD 21632
    • /34

      Est $421,802 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 3,056 Sq Ft

      1610 Cattail Commons Way, Denton, MD 21629

      1610 Cattail Commons Way, Denton, MD 21629
  • /4

    $24,500

    • 2 Beds
    • 1 Bath
    • 1,024 Sq Ft

    204 Academy Ave, Federalsburg, MD 21632

    Investor special! This property is being sold AS-IS and is priced for land value or a full renovation. The existing structure requires extensive repairs or complete tear-down—ideal for experienced builders, contractors, or savvy investors looking for a project. Buyer to verify zoning, permits, potential use. Buyer Broker/Agent and/or Buyer must do their own due diligence to verify if the existing

    Mike Dunn Keller Williams Realty Delmarva

    204 Academy Ave, Federalsburg, MD 21632
  • /27

    $219,990 Sold Jun 30, 2025

    • 1,365 Sq Ft
    • $161/SF
    • 36 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2025

    147 Riverwalk Terrace, Federalsburg, MD 21632

    **Red Tag Sales Event now through April 20, 2025! Was $226,990 Now: $219,990! Home must close on or before 06/13/2025.** Take in stunning river views of the Marshyhope Creek from the back deck of your new home at 147 Riverwalk Terrace in Federalsburg, MD, located in the charming Riverwalk Terrace community. The Jefferson is an open-concept 1,365 square foot two-story interior townhome with three

    Kathleen Cassidy D R Horton Realty of Virginia LLC

    147 Riverwalk Terrace, Federalsburg, MD 21632
    • /47

      Est $403,366 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,768 Sq Ft

      25711 Mockingbird Ln, Greensboro, MD 21639

      25711 Mockingbird Ln, Greensboro, MD 21639
  • /24

    $299,000

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

    505 Maryland Ave, Ridgely, MD 21660

    Welcome to this beautifully updated 3-bedroom, 2-bath rancher located in the charming town of Ridgely, Maryland. Renovated just about two years ago, this home has been lovingly maintained and offers stylish, move-in-ready living with modern finishes throughout. The open-concept kitchen features granite countertops, a spacious island perfect for entertaining, soft-close cabinetry, and

    Kaitlyn Collins Benson & Mangold, LLC

    505 Maryland Ave, Ridgely, MD 21660
  • /23

    $280,000 Sold Jun 28, 2025

    • 1,192 Sq Ft
    • $235/SF
    • 35 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2013

    105 Elmor Ct, Greensboro, MD 21639

    Charming Rancher on a Quiet Cul-de-Sac!Welcome to 105 Elmor Ct, Greensboro, MD 21639 — a beautifully maintained 3-bedroom, 2-bath rancher nestled in a peaceful cul-de-sac in one of Greensboro's most desirable neighborhoods. Built in 2013, this single-level home offers the perfect blend of modern comfort and quiet suburban living.Step inside to find a bright and open layout ideal for

    BJ Kilby Eastern Shore Real Estate, LLC

    105 Elmor Ct, Greensboro, MD 21639
    • /35

      Est $419,174 Not Listed For Sale

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

      1524 Cattail Commons Way, Denton, MD 21629

      1524 Cattail Commons Way, Denton, MD 21629
  • /51

    $549,000

    • 3 Beds
    • 3.5 Baths
    • 2,667 Sq Ft

    22408 Hog Creek Rd, Preston, MD 21655

    NEW PRICE! Two Tranquil Country Acres with No Restrictions, backs to open farmland. Deep Back Yard includes an above ground pool with a deck for your summer enjoyment, large vinyl fenced area for pets and kids, more fenced area for farm animals (pets) and includes a shooting mound should that be of interest. This lovely home Boasts 2,667 Sq. Ft. of Family Space with new LVP flooring though out

    James Bent Benson & Mangold, LLC

    22408 Hog Creek Rd, Preston, MD 21655
  • /70

    $398,000 Sold Jun 27, 2025

    • 2,650 Sq Ft
    • $150/SF
    • 3 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2005

    1110 Osprey Ln, Denton, MD 21629

    Discover this stunning contemporary four bedroom, 2.5 bath home located in a fantastic community that features a pool, tot lots and a community building that's perfect for gatherings! As you step inside, you'll be greeted by a fresh, modern design. The heart of the home is it's gorgeous kitchen, featuring a deep stainless farmhouse sink with a sprayer nozzle, ample storage space in the

    Judith Germain Benson & Mangold, LLC

    1110 Osprey Ln, Denton, MD 21629
    • /36

      Est $300,843 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,914 Sq Ft

      202 Caroline Ave, Ridgely, MD 21660

      202 Caroline Ave, Ridgely, MD 21660
  • /55

    $950,000

    • 4 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    11142 Log Cabin Rd, Denton, MD 21629

    Welcome to 11142 Log Cabin Road! This unique property offers the perfect combination of residential living and valuable commercial space, all on one expansive, 4.53 acre lot. This beautiful colonial-style home has great curb appeal with its classic look, neatly trimmed landscaping, and a spacious front yard shaded by mature trees. The main home spans over 2,700 square feet and features four

    Courtney Gallagher Keller Williams Realty Central-Delaware

    11142 Log Cabin Rd, Denton, MD 21629
  • /22

    $399,900 Sold Jun 27, 2025

    • 1,816 Sq Ft
    • $220/SF
    • 2 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1991

    24771 Woods Dr, Denton, MD 21629

    Welcome to 24771 Woods Drive! This 3-bedroom, 3-bathroom single-level rancher sits on a 0.96+- acre lot with mature landscaping, offering ample space and privacy. The home features an attached 2-car garage for convenient parking and storage. Inside, hardwood floors run throughout the main living areas. The sunken living room includes vaulted ceilings and a wood-burning fireplace, creating a focal

    Brian Gearhart Benson & Mangold, LLC

    24771 Woods Dr, Denton, MD 21629
    • /22

      Est $368,365 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 1,654 Sq Ft

      110 S 8th St, Denton, MD 21629

      110 S 8th St, Denton, MD 21629

Showing Results 201 - 240, Page 6 of 18

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