158

Caroline County MD Homes for Sale

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  • /48

    $395,000

    • 4 Beds
    • 2.5 Baths
    • 2,040 Sq Ft

    502 Kathryn Ct, Denton, MD 21629

    Updated + Upgraded - Turn-key 4BR/2.5BA contemporary 2-story home on a culdesac lot backing to trees, near historic downtown Denton - a true gem of an Eastern Shore town, perchec on the banks of the Choptank River - but tucked away on a residential court. New flooring + paint throughout, new granite counters, new kitchen appliances, new fixtures. Wide open floorplan boasts tall ceilings, spacious

    Charlene Reaser EXP Realty, LLC

    502 Kathryn Ct, Denton, MD 21629
  • /37

    $299,900

    $10K PRICE DROP
    • 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
  • /28

    $669,000

    Open Sat 11AM - 12PM $131K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,880 Sq Ft

    1108 Camp Rd, Denton, MD 21629

    Price Reduction! Motivated Seller. 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

    Michelle Anderson Coldwell Banker Premier - Rehoboth

    1108 Camp Rd, Denton, MD 21629
  • /31

    $399,000

    $70K 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
  • /35

    $379,900

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

    22403 Marsh Creek Rd, Preston, MD 21655

    Custom Brick rancher, close to town on large lot. Open floor plan, spacious kitchen, stainless steel appliances, large island. 3 bedrooms, 2 baths, sunroom overlooking yard. Upgrades include new windows, CAC, new roof new electric service and plumbing New Septic and Well, Closing help will be considered

    Barbara Nichols Results Realty Inc.

    22403 Marsh Creek Rd, Preston, MD 21655
  • /16

    $323,000

    $17K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,892 Sq Ft

    11502 Greensboro Rd, Greensboro, MD 21639

    This is an auction property.This property has been placed in an upcoming event. Please reach out to the listing agent on where the bids are to be submitted. Please submit any pre-auction offer received through the property details page, please reach out to the listing agent. Any post-auction offers will need to be submitted directly to the listing agent. Response within 3 business days. All

    Pamela Geib Long & Foster Real Estate, Inc.

    11502 Greensboro Rd, Greensboro, MD 21639
  • /123

    $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
  • /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
  • /62

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft

    1010 S 2nd St, Denton, MD 21629

    Nestled on the edge of town, 1010 S 2nd Street delivers the convenience of in-town living without in-town taxes. Situated on 1.06 beautifully landscaped acres with mature plantings, this 3-bedroom, 2-bath home offers a spacious feel inside and out. Interior features include hardwood, LVP, and tile flooring, along with a cozy pellet stove fireplace insert for efficient heating, complemented by hot

    Roger Boyce Chesapeake Real Estate Associates, LLC

    1010 S 2nd St, Denton, MD 21629
  • /2

    $279,990

    New Construction $7K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft

    125 Hobbs St, Greensboro, MD 21639

    Discover 125 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
    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
  • /28

    $399,000

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 1,768 Sq Ft

    1 Sunrise Ave, Ridgely, MD 21660

    1 Sunrise Avenue is complete and ready for your private tour today! Just imagine starting your mornings in this thoughtfully crafted Lomaxx Custom Homes new build. Golden light spills across the nearby fields and settles gently indoors, where days begin with coffee on the back deck, birds gliding by, and daylight drifting through the windows, filling each room with a calm glow. Lomaxx Custom

    Crystal Smith RE/MAX Executive

    1 Sunrise Ave, Ridgely, MD 21660
  • /28

    $180,000

    $10K PRICE DROP
    • Land
    • 7.99 Acres
    • $22,528 per Acre

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

    **SELLERS ARE OPEN TO ANY REASONABLE OFFER!!!** 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

    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
  • /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

    $609,000

    • 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. Beautiful Expansive lot size gives you the privacy needed within a walkable neighborhood. The flat level lot opens up future pool and other amenity possibilities. Sit in your rocker with a cocktail while enjoying the dream turned into a reality of a wrap-around porch. A

    Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    24276 Asbury Dr, Denton, MD 21629
  • /111

    $889,000

    $100K 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
  • /94

    $380,000

    • 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,

    Sean Steward Century 21 Home Team Realty

    28440 Bloomery Rd, Federalsburg, MD 21632
  • /20

    $850,000

    $250K 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

    $360,000

    $40K PRICE DROP
    • 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

    $850,000

    • 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

    $49,000

    $6K PRICE DROP
    • Land
    • 14,810 Sq Ft
    • $144,118 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
  • /62

    $630,000

    • 4 Beds
    • 3.5 Baths
    • 3,725 Sq Ft

    26927 Boyce Mill Rd, Greensboro, MD 21639

    Nestled on 5 beautiful acres, this spacious 4-bedroom, 3.5-bath home offers the perfect blend of privacy, comfort, and country living. Approximately 1.8 acres are wooded, providing a peaceful backdrop and frequent visits from local wildlife, while the remaining acreage is cleared and ideal for outdoor enjoyment. The inviting front porch overlooks the private rural setting, while the interior

    Barbara Blosser Long & Foster Real Estate, Inc.

    26927 Boyce Mill Rd, Greensboro, MD 21639
  • /4

    $21,000

    $14K 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
  • /30

    $355,000

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft

    8140 Haven St, Denton, MD 21629

    This charming ranch-style home, built in 1986, offers a perfect blend of comfort and functionality. Minutes to Tuckahoe Creek boat ramp! With 1,300 sq. ft. of well-designed space, it features three inviting bedrooms and two full bathrooms, including a primary suite with a walk-in closet and a tub/shower. The traditional floor plan is enhanced by built-ins and ceiling fans, creating a cozy

    Mary Haddaway Benson & Mangold, LLC

    8140 Haven St, Denton, MD 21629
  • /25

    $334,900

    $5K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,440 Sq Ft

    147 Mill St, Preston, MD 21655

    Well Maintained 4 Bed 2 Full Bath Cape Cod. Large Eat-in Kitchen w/ Stainless Steel Appliances, Granite Countertops and Center Island!Nice Size Family Room. Outdoors feature a Large Shed with Heat and Air (currently used as a very nice office) , Separate Shed for storage at the back of Spacious level Lot. Patio for entertaining and more... Home is less than 1 Mile to Choptank River Landing!

    Kathleen Brenton Brenton Realty Group

    147 Mill St, Preston, MD 21655
  • /35

    $265,000

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 1,584 Sq Ft

    530 Vaughn Ave, Greensboro, MD 21639

    COMING SOON!! Welcome home to this beautifully updated 3-bedroom, 2.5-bath home built by Gemcraft Homes in 2002. Freshly painted throughout in 2026, this move-in-ready home also features brand-new luxury vinyl plank flooring on the main level and new carpet throughout the second floor, offering a fresh, modern feel from the moment you step inside. The main level offers a bright and inviting

    Hunter Geary Hyatt & Company Real Estate, LLC

    530 Vaughn Ave, Greensboro, MD 21639
  • /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
  • /67

    $679,000

    • 4 Beds
    • 2.5 Baths
    • 2,744 Sq Ft

    132 Deep Shore Rd, Denton, MD 21629

    Welcome to 132 Deep Shore Rd—an inviting homestead set on more than 3 acres of beautifully maintained gardens, thoughtfully designed outdoor spaces, and versatile outbuildings. From greenhouse and herb beds to a dedicated drying room and casual nooks for lounging, every corner invites you to savor the seasons. Inside, this spacious home offers over 2,700 sq ft with 4 bedrooms and 2.5 baths. An

    Roger Boyce Chesapeake Real Estate Associates, LLC

    132 Deep Shore Rd, Denton, MD 21629
  • /2

    $272,000

    $2K PRICE INCREASE
    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    325 Carter Ave, Denton, MD 21629

    Excellent cozy home just waiting for you in the town of Denton with the small town atmosphere and a lot of amenities. Affordably priced, close to shopping, easy commute to the Western Shore and close enough to Delaware and Maryland beaches. Come see today because this home will not last long.

    George Thompson Long & Foster Real Estate, Inc.

    325 Carter Ave, Denton, MD 21629
  • /25

    $299,000

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    113 Chamber St, Preston, MD 21655

    Welcome to 113 Chamber Street in the heart of Preston! This well-maintained single-story home offers comfortable living on a spacious 0.42-acre lot within town limits. Featuring 2 full bathrooms, a practical floor plan, and a large detached garage with approximately 880 square feet of space, this property provides plenty of room for parking, storage, hobbies, or a workshop. Enjoy outdoor living

    Heather Brummell Keller Williams Realty

    113 Chamber St, Preston, MD 21655
  • /2

    $330,000

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 1,212 Sq Ft

    104 Chambers St, Federalsburg, MD 21632

    This is the home where you stop worrying about what needs to be fixed. Fully renovated from the ground up—new electrical, new plumbing, new bathrooms, new kitchen with updated appliances and countertops, and beautiful wide plank LVP flooring throughout. Every major system is done. No surprises, no contractor calls, no "we'll need to replace that soon." Just a solid, move-in-ready home where you

    Kaitlyn Collins Benson & Mangold, LLC

    104 Chambers St, Federalsburg, MD 21632
  • /29

    $750,000

    • 3 Beds
    • 2 Baths
    • 4,580 Sq Ft

    14236 Drapers Mill Rd, Greensboro, MD 21639

    STOP, LOOK, and READ...this may be exactly the property you’ve been searching for!! RESIDENTIAL / COMMERCIAL OPPORTUNITY – Zoned C-2, this versatile multi-use property offers endless possibilities! Relocate your business, expand to a second location, or launch your next venture while enjoying the convenience of living and working side by side on this incredible 2+ acre property. This unique

    Karen Clark Clark & Co Realty, LLC

    14236 Drapers Mill Rd, Greensboro, MD 21639
  • /59

    $1,500,000

    Coming Soon
    • 4 Beds
    • 3 Baths
    • 3,358 Sq Ft

    23071 Tuckahoe Springs Dr, Denton, MD 21629

    Beautifully positioned along the deep protected waters of the Tuckahoe, this exceptional residence has been transformed through an extensive renovation that blends timeless design with comfortable waterfront living. Every improvement was carefully planned, resulting in a home that feels as inviting as it is impressive. The heart of the home is the custom kitchen, where blue marble countertops,

    Sydney Johnson Cohee Sharon Real Estate P.C.

    23071 Tuckahoe Springs Dr, Denton, MD 21629
  • /31

    $305,000

    $5K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,234 Sq Ft

    106 Main St, Preston, MD 21655

    Welcome to this charming and spacious home in Preston offering 3 bedrooms, 1.5 bathrooms, and 2,050 square feet of comfortable living space. Freshly painted throughout, this home features beautiful hardwood flooring that adds warmth and timeless character. With generous living areas and a move-in-ready feel, this property blends comfort and style while providing plenty of space for everyday

    Shay Prattis Keller Williams Realty

    106 Main St, Preston, MD 21655

Showing Results 81 - 120, Page 3 of 4

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