157

Caroline County MD Homes for Sale

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  • /59

    $483,000

    Open Sun 2PM - 4PM
    • 4 Beds
    • 3 Baths
    • 1,738 Sq Ft

    24899 Woods Dr, Denton, MD 21629

    Thoughtfully updated and exceptionally versatile, this well-maintained home is tucked away at the end of a quiet cul-de-sac with no HOA and backs to the Caroline Country Club, offering a peaceful setting and beautiful outdoor views. Major systems including the roof, septic, HVAC, well, and a fully encapsulated crawlspace were completed in 2017–2018, providing long-term peace of mind.The main

    Judith Germain Benson & Mangold, LLC

    24899 Woods Dr, Denton, MD 21629
  • /2

    $30,000

    • Land
    • 23,522 Sq Ft
    • $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
  • /37

    $309,900

    • 4 Beds
    • 3.5 Baths
    • 2,280 Sq Ft

    1624 Blue Heron Dr, Denton, MD 21629

    Move-in ready and thoughtfully updated—this is one you won’t want to miss. Step inside this newly renovated 2,200 sq. ft. townhome located in the heart of Denton, MD. Featuring four spacious bedrooms and 3.5 bathrooms, this home offers a perfect blend of comfort, functionality, and modern design. The entry level includes a versatile first-floor bedroom with a walk-in closet—ideal for guests, a

    Michelle DiDonato Island Realty, LLC

    1624 Blue Heron Dr, Denton, MD 21629
  • /2

    $155,000

    $34K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,015 Sq Ft

    208 W 2nd St, Ridgely, MD 21660

    Fixer up in town!!! New hot water 2025. More pictures coming. (Agent Owner)

    Dawn Williams Berkshire Hathaway Homeservice Homesale Realty

    208 W 2nd St, Ridgely, MD 21660
  • /30

    $725,000

    $75K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,880 Sq Ft

    1108 Camp Rd, Denton, MD 21629

    Welcome to 1108 Camp Street, sits on over 14 acres of land where modern comfort meets elegant design through an extensive list of upgrades that enhance both functionality and style. This home features stunning stone work on both the front and back, framing the house in natural beauty and providing a warm welcome. The meticulously crafted stone walls create an inviting outdoor ambiance. Venture

    Michelle Anderson Coldwell Banker Premier - Rehoboth

    1108 Camp Rd, Denton, MD 21629
  • /31

    $415,000

    $54K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 2,885 Sq Ft

    112 S 5th Ave, Denton, MD 21629

    Reduced, sellers are ready to move on! Homes like this is what they use for Christmas cards, large wrap around porch, entry foyer, detailed fireplaces, hard wood floors, and so much more. This is waiting for the right owner to continue the 126 years this home has stood. Everything in this home is in grand size. Large rooms, make this an easy home for a large family . The house current owners have

    Kat Thompson Benson & Mangold, LLC.

    112 S 5th Ave, Denton, MD 21629
  • /103

    $699,000

    • 3 Beds
    • 4 Baths
    • 2,756 Sq Ft

    4 S 1st St, Denton, MD 21629

    Outstanding Business Opportunity! Rare Find with-in Downtown Denton! Property would make an excellent Restaurant, Bar, great Venue , or a Large Victorian Home! Features include but not limited to Residential, Commerical or Mixed Use. Large Wrap around Porch for entertaining, Patio with plenty of room for seating with Firepit. Park like setting with Open Space and Large Pond! Town ERU's are

    Kathleen Brenton Brenton Realty Group

    4 S 1st St, Denton, MD 21629
  • /5

    $130,000

    • Land
    • 8.85 Acres
    • $14,689 per Acre

    15589 Union Rd, Goldsboro, MD 21636

    25309 Golt farm Ln has an old vacant double-wide on it . PLEASE DO NOT GO INSIDE THE FLOORS ARE NOT SAFE TO GO IN.

    Diane Wenk Wright Real Estate

    15589 Union Rd, Goldsboro, MD 21636
  • /45

    $469,900

    $25K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,667 Sq Ft

    22408 Hog Creek Rd, Preston, MD 21655

    NEW PRICE! Enjoy peace and space on two tranquil country acres with no deed restrictions adjacent to open farmland. The deep backyard features a large vinyl-fenced area ideal for kids and pets, an above-ground pool with deck perfect for summer fun. This lovely home offers 2,667 Square feet (estimated) of living space, new LVP flooring on the main floor, and a versitile loft upstairs. The spacious

    James Bent Benson & Mangold, LLC

    22408 Hog Creek Rd, Preston, MD 21655
  • /2

    $210,000

    • 3 Beds
    • 2 Baths
    • 1,484 Sq Ft

    112 Noble Ave, Preston, MD 21655

    Investor Alert! 100% occupied duplex with a 2 bedroom, 1 bath downstairs and a 1 bedroom 1 bath upstairs. Situated in the heart of Preston and close proximity to the school.

    Chuck Mangold Benson & Mangold, LLC

    112 Noble Ave, Preston, MD 21655
  • /10

    $275,000

    • 3 Beds
    • 3 Baths
    • 2,128 Sq Ft

    21245 Tanyard Rd, Preston, MD 21655

    Charming Country Living with Room to Make It Your Own! Welcome to 21245 Tanyard Road, a spacious rancher with 3 bedrooms and 2 full baths nestled on a peaceful 0.62-acre lot in Preston. Built in 1987, this single-level home offers a solid foundation and a functional layout, ready for your personal touch and updates.Whether you're looking for a primary residence or an investment opportunity,

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    21245 Tanyard Rd, Preston, MD 21655
  • /25

    $85,000

    • 4 Beds
    • 30 Baths
    • 1,428 Sq Ft

    28035 Possum Hill Rd, Federalsburg, MD 21632

    Back on the market after demolition of the old house, full lot cleanup, and a garage facelift!This 0.48-acre property on Possum Hill Rd offers a strong opportunity in a desirable location less than one mile from the Maryland–Delaware state line. The lot is now cleared, providing open space and flexibility for a variety of potential uses.The property features an oversized pass-through

    Sam Benkirane Proplocate Realty, LLC

    28035 Possum Hill Rd, Federalsburg, MD 21632
  • /15

    $299,000

    $16K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft

    506 Pintail St, Greensboro, MD 21639

    Nearly new ranch style home with large front porch. Three bedrooms and two full baths plus spacious laundry room enhance this home. Large kitchen with center island with stainless appliances and granite countertops are a focal point of this open floor plan. Move in ready and waiting for a new family!

    Bonnie Johnson Keller Williams Realty

    506 Pintail St, Greensboro, MD 21639
  • /30

    $289,000

    $10K PRICE DROP
    • 4 Beds
    • 1 Bath
    • 1,352 Sq Ft

    14185 Drapers Mill Rd, Greensboro, MD 21639

    Charming 2-Story Farmhouse set on 3 acres along a quiet country road, located directly next to a scenic bird sanctuary! This home offers 4 bedrooms and 1 full bath, including a convenient first-floor bedroom. The layout features a kitchen and dining combination, spacious family room, welcoming foyer, and a separate mudroom/laundry area. Enjoy the peaceful surroundings from the front and side

    John Lyons Crown Homes Real Estate

    14185 Drapers Mill Rd, Greensboro, MD 21639
  • /2

    $286,490

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

    125 Hobbs St, Greensboro, MD 21639

    Discover 125 Hobbs Street, a new home soon to be 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

    D.R. Horton Builder
    125 Hobbs St, Greensboro, MD 21639
  • /15

    $450,000

    • 4 Beds
    • 2 Baths
    • 2,111 Sq Ft

    27329 Jenny Hye Ln, Marydel, MD 21649

    Situated on a 1.51 acre lot, backing to woods, this four Bedroom, 2 full bath home's interior has been completely renovated! Kitchen with eat -in area has been updated with new cabinetry, granite countertops & s/s appliances, Separate dining room for those wanting a more formalized area or can be used as a den, Living room with wood burning fireplace leads to expansive family room with access to

    Kathleen May Synergy Realty

    27329 Jenny Hye Ln, Marydel, MD 21649
  • /26

    $299,000

    Open Sat 11AM - 1PM $16K PRICE DROP
    • 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

    $190,000

    • Land
    • 7.99 Acres
    • $23,780 per Acre

    Parcels #82 & #96 Drapers Mill Rd, Goldsboro, MD 21636

    Discover the possibilities with these 2 buildable lots totaling 7.994± acres on Maryland’s beautiful Eastern Shore. Each parcel is perc approved for a 4-bedroom home, offering flexibility whether you're ready to build now or planning for the future.The property is clearly marked with blue paint and stakes, making it easy to walk and envision your plans. Both lots are wooded, providing natural

    Erin Anderson Chesapeake Real Estate Associates, LLC

    Parcels #82 & #96 Drapers Mill Rd, Goldsboro, MD 21636
  • /37

    $299,000

    • 3 Beds
    • 1 Bath
    • 1,222 Sq Ft

    7192 American Corner Rd, Denton, MD 21629

    Come make this updated and move in ready rancher your new home. Considerable improvements have been made over the last two years to include the following. This home has a new deep well, new septic system, new tankless propane water heater, new washer/dryer. new range and refrigerator, new roof, new siding, new hvac, renovated bathroom, new flooring, fresh paint, new privacy and chain link fencing

    Andrew Beaven Wright Real Estate

    7192 American Corner Rd, Denton, MD 21629
  • /4

    $155,000

    • 1 Bed
    • 1 Bath
    • 512 Sq Ft

    26355 Marydel Rd, Marydel, MD 21649

    House is of little to no value, existing well and septic. This house includes an additional parcel of 7 acres, tax id, 0601012428 for a total of 7.27 acres. Property being SOLD AS IS.

    George Thompson Long & Foster Real Estate, Inc.

    26355 Marydel Rd, Marydel, MD 21649
  • /50

    $465,000

    Open Sat 11AM - 1PM
    • 3 Beds
    • 2.5 Baths
    • 1,840 Sq Ft

    11421 Maplewood Dr, Ridgely, MD 21660

    This charming ranch-style home in Maplewood Estates offers a perfect blend of comfort and modern living with beautiful finishes and soaring ceilings. Built in 2020, the open floor plan invites you to enjoy a spacious living area that seamlessly connects to a delightful country kitchen, complete with a huge center island and breakfast area-ideal for gatherings. The home features three nicely sized

    Tricia Wilson Wilson Realty & Staging LLC

    11421 Maplewood Dr, Ridgely, MD 21660
  • /15

    $189,000

    $26K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,406 Sq Ft

    24876 Meeting House Rd, Denton, MD 21629

    Traditional country style home sits right out side town limits. Close to town and Denton amenities, make this an excellent location for convenience. Nice size yard for a garden, pets, or children. This has been a rental for many years and has always been cared for. Continue this as a rental or make this your home. With a bit of love this could be a great starter home. Property being sold as -is,

    Kat Thompson Benson & Mangold, LLC.

    24876 Meeting House Rd, Denton, MD 21629
  • /11

    $3,700,000

    8019 Patten Rd, Denton, MD 21629

    Poultry farm features a total of 60.57 acres (40 acres tillable, 8.5 acres wooded, 1.5-acre retention pond) and a 40x72 shop that has garage parking and a separate space that could be finished for permanent living. Located approx. 5 miles from the DE line. Expired site evaluation-no septic on property.

    Tambra Reagan CALLAWAY FARNELL AND MOORE

    8019 Patten Rd, Denton, MD 21629
  • /50

    $629,000

    • 5 Beds
    • 2.5 Baths
    • 2,920 Sq Ft

    24276 Asbury Dr, Denton, MD 21629

    Nestled in the shadows of the Choptank River is a meticulously maintained home in the water-privileged neighborhood of Asbury. Expansive lot sizes give you the privacy needed within a walkable neighborhood. Sit in your rocker with a cocktail while enjoying the dream turned into a reality of a wrap-around porch. A large rear screened-in porch to watch the local wildlife opens onto extensive

    Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    24276 Asbury Dr, Denton, MD 21629
  • /111

    $939,000

    $50K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,520 Sq Ft

    8416 Harmony Rd, Denton, MD 21629

    Discover a truly rare opportunity where lifestyle, income potential, and homeownership come together on this expansive 12.7-acre, two-parcel property zoned rural—offering unmatched flexibility and endless possibilities.Currently operating as a productive orchard, greenhouse operation, and microgreens business, this property is thoughtfully equipped for both personal enjoyment and

    Casey Neves The Parker Group

    8416 Harmony Rd, Denton, MD 21629
  • /54

    $445,000

    Open Sat 11AM - 1PM
    • 3 Beds
    • 2 Baths
    • 2,044 Sq Ft

    23283 Magnolia Hills Rd, Denton, MD 21629

    This charming ranch-style home in the desirable Magnolia Hill community offers a perfect blend of comfort and modern living. With 3 spacious bedrooms and 2 full bathrooms, the open floor plan with cathedral ceilings invites natural light, creating a warm and welcoming atmosphere. The eat-in kitchen features an island, ideal for casual meals, while the adjoining dining area is perfect for

    Tricia Wilson Wilson Realty & Staging LLC

    23283 Magnolia Hills Rd, Denton, MD 21629
  • /57

    $479,900

    $15K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    7837 Shore Dr, Preston, MD 21655

    Two Johns – Charming Home in a Sought-After Waterfront Community Nestled between Preston and Denton in the desirable Two Johns subdivision, this beautifully maintained 4-bedroom, 2.5-bath home offers a rare blend of comfort, style, and location. Just a few houses away from the public boat landing, residents enjoy easy water access for boating, kayaking, or fishing. Take in serene water views from

    Eddie Matthews Benson & Mangold, LLC

    7837 Shore Dr, Preston, MD 21655
  • /2

    $179,000

    • 2 Beds
    • 2 Baths
    • 968 Sq Ft

    107 N School St Unit 3B, Greensboro, MD 21639

    Rare Opportunity ! Built 1922 as a school and converted into condo units. Many of the original elements make each building unique. With massive windows different architectural elements makes each unit distinctive. Open floor plan with updated appliances make this turn key for its next resident.. This unit has Two comfortable size bedrooms, two full baths, washer and dryer. There is an owner

    Kat Thompson Benson & Mangold, LLC.

    107 N School St Unit 3B, Greensboro, MD 21639
  • /20

    $950,000

    Open Sat 11AM - 12PM $150K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,320 Sq Ft

    6401 Laurel Grove Rd, Denton, MD 21629

    Nestled on an expansive 52.08-acre estate, this stunning ranch-style farm offers a harmonious blend of luxury and tranquility, perfect for those seeking an exclusive lifestyle in a serene rural setting. The property boasts a traditional architectural design, complemented by aluminum siding that enhances its timeless appeal. Step inside to discover a thoughtfully designed interior that exudes

    Michelle Anderson Coldwell Banker Premier - Rehoboth

    6401 Laurel Grove Rd, Denton, MD 21629
  • /6

    $400,000

    Open Sat 1PM - 3PM
    • 4 Beds
    • 2 Baths
    • 2,128 Sq Ft

    26784 Bilbrough Rd, Goldsboro, MD 21636

    Welcome to your private slice of Eastern Shore living in Goldsboro. Set on 4.7 secluded acres, this 2022-built home offers the space, comfort, and modern features today’s market demands. With over 2,100 square feet, 4 bedrooms, and 2 full baths, the layout is open, bright, and designed for seamless everyday living. Step inside to a spacious floor plan that flows effortlessly from room to

    Sandra Bradley Keller Williams Select Realtors of Easton

    26784 Bilbrough Rd, Goldsboro, MD 21636
  • /19

    $950,000

    Open Sat 11AM - 12PM
    • 3 Beds
    • 2 Baths
    • 2,320 Sq Ft

    6401 Laurel Grove Rd, Denton, MD 21629

    Nestled on an expansive 52.08-acre estate, this stunning ranch-style farm offers a harmonious blend of luxury and tranquility, perfect for those seeking an exclusive lifestyle in a serene rural setting. The property boasts a traditional architectural design, complemented by aluminum siding that enhances its timeless appeal. Step inside to discover a thoughtfully designed interior that exudes

    Michelle Anderson Coldwell Banker Premier - Rehoboth

    6401 Laurel Grove Rd, Denton, MD 21629
  • /2

    $32,500

    • Land
    • 30,056 Sq Ft
    • $47,101 per Acre

    0 Douglas & Lincoln St Unit MDCM2006716, Ridgely, MD 21660

    Just next to the quaint town of Ridgely, this .69 acre lot also comes with a bonus lot highlighted in photos. Buy and hold as an investment or see if you can perc.

    Michael Rosendale Rosendale Realty

    0 Douglas & Lincoln St Unit MDCM2006716, Ridgely, MD 21660
  • /3

    $55,000

    • Land
    • 14,810 Sq Ft
    • $161,765 per Acre

    507 W Central Ave, Federalsburg, MD 21632

    Discover a unique opportunity to create your dream home on this spacious 0.34-acre parcel of land, nestled in a serene suburban setting. This property offers a blank canvas for your vision, allowing you to design a residence that perfectly suits your lifestyle and preferences. Imagine waking up each day to the gentle sounds of nature, with the peaceful ambiance of a suburban neighborhood

    Joni Barrow Coldwell Banker Realty

    507 W Central Ave, Federalsburg, MD 21632
  • /10

    $184,900

    • 3 Beds
    • 1 Bath
    • 716 Sq Ft

    406 Lincoln St, Denton, MD 21629

    This adorable home is ready and waiting for you to move in and make it your own. The home was renovated just 2 years ago. Updated items include windows, HVAC, cabinets, flooring, carpet, plumbing, electrical, roof & new insulation in the crawl space. Enjoy being close to local restaurants, shops, parks, schools, boat ramps, and MD/DE beaches. This property was most recently used as an

    Lisa Andrews Chesapeake Real Estate Associates, LLC

    406 Lincoln St, Denton, MD 21629
  • /30

    $750,000

    • 3 Beds
    • 2 Baths
    • 1,932 Sq Ft

    7844 Shore Dr, Preston, MD 21655

    Unplug from the hustle and bustle in this well maintained one floor home on the banks of the Choptank River. The views of the native wetlands and its wildlife are unique and beautiful in a way only mother nature can create. The spacious and quiet yard receives abundant sunlight and could provide for amazing gardening opportunities. An old dock remains in need of extensive repair but the next

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    7844 Shore Dr, Preston, MD 21655
  • /4

    $24,500

    $11K PRICE DROP
    • 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
  • /36

    $250,000

    • 2 Baths
    • 3,028 Sq Ft

    130 Halltown Rd, Marydel, MD 21649

    Can you turn this space into a home? It’s the kind of opportunity that doesn’t come around often here in Marydel. This former church turned community hall sits on just under an acre and offers over 3,000 square feet to work with, including a wide open event space and a surprisingly large kitchen at just over 515 square feet. The subflooring and joists in the main hall have already been replaced

    Micheal Vakas EXP Realty, LLC

    130 Halltown Rd, Marydel, MD 21649
  • /23

    $200,000

    • 3 Beds
    • 2.5 Baths
    • 1,860 Sq Ft

    1507 Blue Heron Dr, Denton, MD 21629

    3-Story Townhome Ready for Its New Owners!Home offers 3 bedrooms and 2.5 baths with a functional layout and comfortable living spaces. The spacious first floor features an open living area and convenient half bath for guests.The second floor includes two bedrooms, a full bath, and laundry area, providing everyday convenience. The third-floor primary suite offers a private retreat with a

    KL Harris Keller Williams Select Realtors of Cambridge

    1507 Blue Heron Dr, Denton, MD 21629
  • /40

    $269,999

    $20K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,056 Sq Ft

    12 N Maple Ave, Ridgely, MD 21660

    Welcome home to this charming 2-bedroom, 1-bath gem nestled in a quiet, established neighborhood. Perfect for first-time buyers, downsizers, or anyone looking for comfortable, low-maintenance living, this home offers both warmth and functionality. Step inside to find beautiful new wood flooring flowing through the living room, kitchen, and hallway, creating a fresh and modern feel throughout the

    Wes Russum Coldwell Banker Chesapeake Real Estate Company

    12 N Maple Ave, Ridgely, MD 21660
  • /3

    $282,990

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

    Curtis Plan at Kinnamon Meadows, Greensboro, MD 21639

    The Curtis is a 1,182 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 allows for the two guest bedrooms and guest bathroom to be separate from the living areas of the home. Along

    D.R. Horton Builder
    103 Park Ave Unit 36203276, Greensboro, MD 21639

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