133

Caroline County MD Homes for Sale

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  • /26

    $315,000

    • 3 Beds
    • 2 Baths
    • 1,104 Sq Ft

    1 Oakview Ct, Ridgely, MD 21660

    Well-maintained 3BR, 2BA home offering a functional layout with a cozy living room and an updated kitchen featuring stainless steel appliances. The primary bedroom includes a full bath, and the laundry/mudroom provides added practicality. Fresh paint throughout, plus a fenced yard, gazebo, and patio create inviting outdoor space. Recent improvements include solar panels (2018) and a new roof

    Peter Stark Benson & Mangold, LLC

    1 Oakview Ct, Ridgely, MD 21660
  • /28

    $330,000

    • 3 Beds
    • 2 Baths
    • 1,590 Sq Ft

    25903 Dogwood Rd, Greensboro, MD 21639

    Welcome to the tucked away community of Fox Grape Farms. This home offers a comfortable layout designed for everyday living and easy entertaining. To the left of the foyer is the dining area that has stunning oak floors and exposed beams. The dining area is open to the kitchen which features great cabinet and counter space for cooking and prep. Bar seating at the kitchen counter and direct access

    Courtney Gallagher Keller Williams Realty Central-Delaware

    25903 Dogwood Rd, Greensboro, MD 21639
  • /2

    $60,000

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

    21269 Dover Bridge Rd, Preston, MD 21655

    Nestled in Dover Bridge Mobile Home Park—formerly Prettyman Manor—this double-wide manufactured home sits on one of the largest lots in this peaceful community. The property offers plenty of space and potential, with a few upcoming improvements to help set the stage for its next owner. While it could use a bit of attention, it’s a wonderful opportunity to make this home your own in a quiet,

    Kelly Howard Coldwell Banker Realty

    21269 Dover Bridge Rd, Preston, MD 21655
  • /2

    $145,000

    • 2 Beds
    • 1 Bath
    • 504 Sq Ft

    305 Maple Ave, Ridgely, MD 21660

    This cozy cottage, situated on a quiet alley, would be perfect for an individual or a young couple. Enjoy your morning coffee on the screened porch. Fenced backyard with a garden shed.More photos soon.

    Andrew Beaven Wright Real Estate

    305 Maple Ave, Ridgely, MD 21660
  • /2

    $484,900 Coming Soon

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

    24846 Branfields Dr, Ridgely, MD 21660

    Beautifully semi-custom home built in 2016, ideally sited on a 1+ acre lot alongside open space in the sought after Branfields neighborhood. This meticulously maintained property offers one - level living with select handicap-accessible features. Inside, enjoy cathedral ceilings, a cozy fireplace and gourmet kitchen perfect for entertaining. Outdoor living shines with a fabulous 16x24 screened

    Kelly Showell Benson & Mangold, LLC

    24846 Branfields Dr, Ridgely, MD 21660
  • /3

    $265,000 Coming Soon

    • 1 Bed
    • 1 Bath
    • 1,092 Sq Ft

    10819 Greensboro Rd, Denton, MD 21629

    Newly Renovated in 2026. Coming Soon

    Barbara Beaudet Brenton Realty Group

    10819 Greensboro Rd, Denton, MD 21629
  • /56

    $497,000

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

    20915 Dover Bridge Rd, Preston, MD 21655

    Set on 8.6 private, fully fenced acres just across the Dover Bridge, this Eastern Shore property offers endless possibilities with scenic surroundings, expansive land, and close proximity to the Choptank River and minutes to Easton. The single-level home features 3 bedrooms and 2 full bathrooms, a country kitchen, and an open-concept layouthighlighted by a massive brick fireplace with insert and

    Alex Martinez The Agency DC

    20915 Dover Bridge Rd, Preston, MD 21655
  • /14

    $375,000

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

    11305 River Rd, Ridgely, MD 21660

    Charming 3-bedroom, 1-bath rancher offers over 1500 SF of comfortable living space. Several updates have already been completed, making this home move in ready with room to add your own touches. Enjoy peaceful mornings and evenings on the screened-in rear porch, perfect for relaxing while taking in the surrounding wildlife. A great blend of comfort, space and natural serenity.

    Pamela Geib Long & Foster Real Estate, Inc.

    11305 River Rd, Ridgely, MD 21660
  • 129 Hobbs St, Greensboro, MD 21639

    $273,990 New Construction

    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft

    129 Hobbs St, Greensboro, MD 21639

    Discover 129 Hobbs Street, a new home under-construction in the quaint Kinnamon Meadows community of Greensboro, MD. The Curtis is a 1,182 square foot, cottage-style ranch home with three bedrooms, two bathrooms, and a two-car driveway. 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

    D.R. Horton Builder
    129 Hobbs St, Greensboro, MD 21639
  • /11

    $267,500

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    408 Bernard Ave, Greensboro, MD 21639

    This charming ranch-style home in the serene Town of Greensboro offers a perfect blend of comfort and functionality. With 1,232 square feet of well-designed living space, this residence features three inviting bedrooms and two full bathrooms, ideal for both relaxation and entertaining. Step inside to discover a warm and welcoming atmosphere, highlighted by plush carpeting and stylish vinyl

    Daniel Hill Long & Foster Real Estate, Inc.

    408 Bernard Ave, Greensboro, MD 21639
  • /2

    $23,000

    • Land
    • 0.14 Acre
    • $164,286 per Acre

    12115 Lincoln St, Ridgely, MD 21660

    Lot in the town of Ridgely, check with the town/county about putting a new house on this lot. There was previously a house on this lot.

    Pamela Geib Long & Foster Real Estate, Inc.

    12115 Lincoln St, Ridgely, MD 21660
  • /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

    $268,490 New Construction

    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft

    132 Hobbs St, Greensboro, MD 21639

    Discover the Perry in Kinnamon Meadows, a 1,059 square foot open concept cottage-style ranch home, offering two bedrooms and two bathrooms at 132 Hobbs Street in Greensboro, MD. A welcoming front porch leads you into the spacious living room that seamlessly flows into the kitchen, creating a perfect space for entertaining guests or enjoying family time. The well-equipped kitchen is complete with

    D.R. Horton Builder
    132 Hobbs St, Greensboro, MD 21639
  • /9

    $89,900

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft

    11584 Greensboro Rd, Greensboro, MD 21639

    This Craftsman style home offers a blank canvas for your vision of classic architectural elements for the discerning buyers. This property presents excellent investment potential. The solid construction provides a strong foundation for future appreciation. With thoughtful updates, this home could significantly increase in value while maintaining its distinctive character. The exterior storage

    Pamela Geib Long & Foster Real Estate, Inc.

    11584 Greensboro Rd, Greensboro, MD 21639
  • /2

    $30,000

    • Land
    • 0.54 Acre
    • $55,556 per Acre

    26519 3 Bridges Rd, Federalsburg, MD 21632

    Previous building is a complete tear down. Do not enter the building. Half acre lot zoned R1, one property. Buyer must contact Caroline County for any more information. There could be a private community septic on the property. Seller will consider holding a 2 year note with $15,000 down payment.

    Charles Hajjar Smart Realty, LLC

    26519 3 Bridges Rd, Federalsburg, MD 21632
  • /29

    $339,000

    • 2 Beds
    • 1.5 Baths
    • 2,017 Sq Ft

    211 Bloomingdale Ave, Federalsburg, MD 21632

    Welcome to 211 Bloomingdale Ave. This custom‐built Brick Williamsburg‐style colonial showcases true craftsmanship, featuring beautiful hardwood floors throughout, custom built‐ins, and detailed moldings. The spacious living room offers an inviting wood‐burning fireplace, while the large great room with its vaulted ceiling provides flexible living space and could easily be converted into a third

    Jana Meredith Meredith Fine Properties

    211 Bloomingdale Ave, Federalsburg, MD 21632
  • /35

    $299,000

    • 3 Beds
    • 2 Baths
    • 1,787 Sq Ft

    3675 Seaman Rd, Preston, MD 21655

    Charming Eastern Shore property set on a peaceful stretch of Seaman’s Road in Preston, MD. Enjoy the tranquility of country living with convenient access to nearby towns, outdoor recreation, and local amenities. A great opportunity for those seeking space, privacy, and small-town charm.

    Brian Jones Keller Williams Select Realtors of Annapolis

    3675 Seaman Rd, Preston, MD 21655
  • /70

    $324,500

    • 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
  • /2

    $249,900

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    5940 Noble Rd, Federalsburg, MD 21632

    Welcome to peaceful rural living just minutes from town conveniences in Federalsburg, MD. This well-situated single-story ranch home offers functional and accessible living across one level, perfectly suited for first-time buyers, downsizers, or those seeking country comfort with ample outdoor space. You'll have nearly 3 acres of land — great for gardening, recreation, or possbly a future

    Holly Anderson Long & Foster Real Estate, Inc.

    5940 Noble Rd, Federalsburg, MD 21632
  • /48

    $355,000

    • 2 Beds
    • 1.5 Baths
    • 708 Sq Ft

    13306 Greensboro Rd, Greensboro, MD 21639

    Stunning waterfront renovation on the Choptank River—completely redone inside and out in 2025! This beautifully updated 2-bedroom, 1.5-bath home offers approximately 800± square feet of thoughtfully designed living space. Completely remodeled from top to bottom, the residence showcases modern design and high-end finishes throughout. Updates include all-new walls, bathrooms, appliances, kitchen

    Lisa Magnus Clark & Co Realty, LLC

    13306 Greensboro Rd, Greensboro, MD 21639
  • /14

    $399,000

    • 3 Beds
    • 2 Baths

    0 Quail Ct Unit MDCM2006644, Greensboro, MD 21639

    Quick Delivery – To Be Built Rancher!This beautifully designed rancher offers 3 bedrooms and 2 full baths with an open-concept floor plan and cathedral ceilings in the main living area. The builder includes a generous package of upgrades at no additional cost. Enjoy an oversized attached two-car garage and a rear deck perfect for outdoor living. Situated on a cleared 1-acre lot in a private

    Barbara Blosser Long & Foster Real Estate, Inc.

    0 Quail Ct Unit MDCM2006644, Greensboro, MD 21639
  • /2

    $110,000

    • 3 Beds
    • 1 Bath
    • 888 Sq Ft

    3471 Laurel Grove Rd, Federalsburg, MD 21632

    Looking for a project with potential? This 3-bedroom, 1-bath home in Federalsburg is ready for someone with vision. Offering solid bones and a large detached garage, it’s the perfect opportunity to renovate, customize, and build equity. Whether you’re an investor or a handy buyer wanting a fixer-upper, this property gives you room to make it your own. Great possibilities — bring your ideas and

    Heather Brummell Keller Williams Realty

    3471 Laurel Grove Rd, Federalsburg, MD 21632
  • /27

    $325,000

    • 7 Beds
    • 3 Baths
    • 2,729 Sq Ft

    210 Old Line Rd, Goldsboro, MD 21636

    For The Love Of Old Homes!! This big and bold 1900s landmark is bursting with soul and charm. Spanning over 2700+ square feet and boasting 6-7 bedrooms / 3 full baths across three stories, it’s the ultimate setting for grand entertaining or quiet relaxation. From the welcoming foyer to the third-floor retreat, every inch exudes character. It’s move-in ready but invites your creative TLC to truly

    Karen Clark Clark & Co Realty, LLC

    210 Old Line Rd, Goldsboro, MD 21636
  • /13

    $235,000

    • 3 Beds
    • 2.5 Baths
    • 1,753 Sq Ft

    1202 Blue Heron Dr, Denton, MD 21629

    WELCOME HOME!!! 1753 SQ FT OF COMFORT...... 3 FLOORS, 3 SPACIOUS BEDROOMS, 3 BATHROOMS, WHITE WOOD CABINETS, MARBLE COUNTERTOPS, STAINLESS STEEL APPLIANCES, LUXURY VINYL FLOORING DOWNSTAIRS, FULLY CARPETED UPSTAIRS, LAUNDRY ROOM, PANTRY AND MORE. CORNER LOT/ QUICK ENTRY & EXIT/ PLAYGROUND/ POOL / CLUBHOUSE/ PET FRIENDLY NEIGHBORHOOD/ HOA / CLOSE DRIVE TO SCHOOLS, STORES, OCEAN CITY, CHESAPEAKE

    SHANTA PHILLIPS EXP Realty, LLC

    1202 Blue Heron Dr, Denton, MD 21629
  • /50

    $674,900

    • 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
  • /71

    $1,099,999

    • 4 Beds
    • 2.5 Baths
    • 3,242 Sq Ft

    7904 Clark Rd, Denton, MD 21629

    This ±45-acre previously certified organic farm is located just south of Denton and offers a well-rounded combination of productive farmland, agricultural infrastructure, and residential living. The property includes approximately ±41 acres of tillable ground equipped with a subsurface irrigation system fed by six on-site wells, providing efficient and reliable water delivery for a wide range of

    Jesse Highling The Land Group

    7904 Clark Rd, Denton, MD 21629
  • /12

    $135,000

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    103 Chamber St, Preston, MD 21655

    This Colonial home features timeless architecture and thoughtful design. The property offers solid construction and classic appeal, making it an excellent opportunity for discerning buyers. This distinctive property presents an outstanding opportunity for transformation and value creation. The established neighborhood setting combines small-town charm with practical accessibility to essential

    Pamela Geib Long & Foster Real Estate, Inc.

    103 Chamber St, Preston, MD 21655
  • /27

    $379,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 2 Baths
    • 1,792 Sq Ft

    25999 Fox Grape Rd, Greensboro, MD 21639

    Welcome to this beautifully updated 4-bedroom, 2-bath home nestled in the peaceful Fox Grape Farms community. This move-in-ready property features a recently remodeled kitchen and bathrooms, along with refinished hardwood floors that add warmth and charm throughout. Set on a serene half-acre wooded lot, the home offers wonderful outdoor living with an 8' x 14' enclosed porch, a rear deck with a

    Amy Betts Coldwell Banker Realty

    25999 Fox Grape Rd, Greensboro, MD 21639
  • /57

    $475,000

    • 3 Beds
    • 2 Baths
    • 2,038 Sq Ft

    27329 Iron Gate Rd, Federalsburg, MD 21632

    Charming Colonial-style farmhouse set on 9 scenic acres, offering a rare blend of historic character, pastoral beauty, and endless potential. Ideal for animal lovers or those seeking a peaceful weekend retreat, the home features hardwood floors, exposed ceiling beams, and three wood-burning stoves that add warmth and timeless appeal. Large Spacious bedrooms, a screened porch and rear patio

    Shannon Parker Keller Williams Select Realtors of Cambridge

    27329 Iron Gate Rd, Federalsburg, MD 21632
  • /42

    $485,000

    • 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
  • /17

    $230,000

    • 3 Beds
    • 2 Baths
    • 1,448 Sq Ft

    113 Maple Ave, Goldsboro, MD 21636

    Welcome to the pleasures of small town living in this updated Farmhouse. This 3 bed 2 bath home sits on a .23 acre lot with most of the land in the backyard for relaxing and entertaining. Plenty of room for gardens or playground area. Outbuilding for extra storage. Enjoy the evenings on the back deck overlooking the yard or enjoy the front porch with coffee and listen to the rain.

    Roger Boyce Chesapeake Real Estate Associates, LLC

    113 Maple Ave, Goldsboro, MD 21636
  • /22

    $399,000

    • 3 Beds
    • 2 Baths
    • 2,412 Sq Ft

    1302 Trice Meadows Cir, Denton, MD 21629

    Lovely Raised Rancher consisting of 2,412 square feet of living with the main level having 3 bedrooms, 2 bathrooms, office/den, living room, kitchen and laundry area with a split floor plan of the bedrooms and the owner's suite on the opposite end of house. No worries about parking your vehicles with this nice 2 car attached garage and on street parking. Additionally, the second floor 52x15 bonus

    George Thompson Long & Foster Real Estate, Inc.

    1302 Trice Meadows Cir, Denton, MD 21629
  • /99

    $1,100,000

    • 6 Beds
    • 3.5 Baths
    • 3,704 Sq Ft

    13539 Hokum Dr, Greensboro, MD 21639

    A Private Eastern Shore Compound Designed for Living, Relaxing & Entertaining!Welcome to 13539 Hokum Drive, a rare Eastern Shore retreat offering privacy, amenities, and “room to breathe” on a gorgeous, partially wooded landscape. This isn’t just a home — it’s a full lifestyle setting, complete with multiple outbuildings, an in-ground pool, wooded trails, and incredible outdoor living spaces,

    Vincent Payne Realty Navigator

    13539 Hokum Dr, Greensboro, MD 21639
  • /3

    $99,000

    • 2 Beds
    • 1 Bath
    • 956 Sq Ft

    804 Gay St, Denton, MD 21629

    Property is being sold in as/ is condition.

    Diane Wenk Wright Real Estate

    804 Gay St, Denton, MD 21629
  • /23

    $315,000

    • 3 Beds
    • 2 Baths
    • 1,646 Sq Ft

    130 Charlotte Ave, Federalsburg, MD 21632

    Welcome to this well-maintained 3BR/2BA home offering convenient one-level living in a quiet Federalsburg neighborhood. Built in 2006, this home features a bright and functional layout with all bedrooms and baths located on the main floor. The brick-front exterior provides great curb appeal, and the spacious 0.43-acre lot offers plenty of outdoor enjoyment. An attached 2-car garage provides

    FRANK LITTLE Berkshire Hathaway HomeServices PenFed Realty

    130 Charlotte Ave, Federalsburg, MD 21632
  • /30

    $375,000

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

    24383 Robins Creek Rd, Preston, MD 21655

    VERY NICE 3-4 BEDROOM, 2 BATH HOME IN TWO JOHNS WATERFRONT COMMUNITY. BOAT LANDING APPROXIMATELY 1/4 MILE AWAY. LARGE LIVING ROOM, KITCHEN-DINING ROOM COMBO, PANELED WALLS ARE ALL PAINTED, MOSTLY WOOD FLOORS. LARGE DECK AT REAR OF HOUSE. MORE PICTURES TO COME SOON. ONLY 40 MILES TO WESTERN SHORE, LESS THAN 60 MILES TO THE BEACH

    Ed Quidas Long & Foster Real Estate, Inc.

    24383 Robins Creek Rd, Preston, MD 21655
  • /39

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft

    24029 Meadows Dr, Ridgely, MD 21660

    Enjoy the best of Eastern Shore living with the tranquility of a quiet, country setting while remaining conveniently located just outside of the quaint little town of Ridgely. This nanticoke rancher features a nice family room addition off the kitchen and is located on a private 2 acre lot on the end of a cul-de-sac. Featuring 3 bedrooms and 2 full baths and a two car garage. This property also

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    24029 Meadows Dr, Ridgely, MD 21660
  • /37

    $609,900 Open Sat 10AM - 12PM

    • 4 Beds
    • 5 Baths
    • 3,491 Sq Ft

    24712 Tribbett Cir, Ridgely, MD 21660

    Welcome to 24712 Tribbett Circle — a beautifully appointed 2016-built home set on 2.43 pristine acres in one of Ridgely’s most desirable neighborhoods. This luxurious 4-bedroom, 4-bathroom property seamlessly blends timeless style with modern comfort, offering an exceptional living experience both inside and out. The main level is adorned with rich bamboo flooring, creating a warm and

    Chris Warren Long & Foster Real Estate, Inc.

    24712 Tribbett Cir, 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
  • /127

    $2,999,000

    • 8 Beds
    • 16 Baths
    • 9,364 Sq Ft

    4218 Harmony Rd, Preston, MD 21655

    A truly rare offering for the discerning auto enthusiast, this exceptional 58.48-acre Eastern Shore estate is a masterfully designed luxury compound where architectural elegance meets world-class automotive accommodations. Introduced by a private gated entrance and tree-lined circular drive, the stately brick home immediately conveys the scale, privacy, and prestige of this one-of-a-kind

    Donna Harrington Coldwell Banker Realty

    4218 Harmony Rd, Preston, MD 21655

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