156

Caroline County MD Homes for Sale

Section Image Section Image
  • /34

    $245,000

    • 3 Beds
    • 2 Baths
    • 1,840 Sq Ft

    158 Wright St, Preston, MD 21655

    Step back in time with this charming 3-bedroom, 2-bathroom home built in 1890, located in the heart of Preston. Full of character and original details, this home offers a unique opportunity to restore and customize a piece of local history. The inviting living room features a cozy fireplace, perfect for relaxing evenings. A large laundry room and a separate den/office provide flexibility and

    Wes Russum Coldwell Banker Chesapeake Real Estate Company

    158 Wright St, Preston, MD 21655
  • /8

    $355,000

    • 3 Beds
    • 2.5 Baths
    • 2,286 Sq Ft

    27279 Jenny Hye Ln, Marydel, MD 21649

    Welcome to Your Peaceful Retreat!This 3-bedroom, 2.5-bath split-foyer home offers 1,488 sq. ft. of comfortable living space, plus a full basement and an attached one-car garage. With its classic brick-and-siding exterior, inviting front patio, and serene surroundings, this property blends warmth, character, and endless potential.Step inside and imagine the possibilities—a bright, open

    Glory Bee Costa Keller Williams Select Realtors of Easton

    27279 Jenny Hye Ln, Marydel, MD 21649
  • /25

    $429,500 Open Sat 12PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 2,692 Sq Ft

    5 Lister Ln, Ridgely, MD 21660

    PRICE REDUCED 10/30/2025! This house is the one you've been waiting for! Huge amount of space with 4 to 5 bedrooms, unfinished basement and a 2-car garage. Located in the fantastic community of Lister Estates. Situated right next to the Ridgely Elementary School and just steps from the Middle School and High School Bus Stops that can be seen from the front porch! New Roof 2 years old and HVAC

    Connie Mahaney Schwartz Realty, Inc.

    5 Lister Ln, Ridgely, MD 21660
  • /71

    $500,000

    • 4 Beds
    • 2 Baths
    • 1,986 Sq Ft

    25699 Auction Rd, Federalsburg, MD 21632

    ***BUYER WALKED AWAY!!****Mortgage savings may be available for buyers of this home.Opportunity to purchase a working farm with remodeled residence - from new luxury vinyl plank flooring and Advantech subfloors to a fully replaced middle beam for lasting structural integrity. Nearly all windows and doors are brand new, the heating system has been upgraded to an efficient heat pump, and

    Barbara McCaffrey Redfin Corp

    25699 Auction Rd, Federalsburg, MD 21632
  • /32

    $315,000

    • 4 Beds
    • 2.5 Baths
    • 1,624 Sq Ft

    407 Wood Duck Dr, Greensboro, MD 21639

    SELLERS ARE OFFERING A $2,500 CREDIT toward refinishing hardwood floors with a reasonable offer, an amazing opportunity to customize the look to your taste. TOP 10 FEATURES you will love about this home: 1) FOUR spacious bedrooms for under $330,000 with the primary bedroom having its on en-suite. 2) Built in 2004, offering modern construction, efficient systems, and a solid layout. 3) Backs to

    Kathryn Matic Patterson-Schwartz - Greenville

    407 Wood Duck Dr, Greensboro, MD 21639
  • /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,

    SHANTA PHILLIPS EXP Realty, LLC

    1202 Blue Heron Dr, Denton, MD 21629
  • /72

    $260,000

    • 2 Beds
    • 2 Baths
    • 2,048 Sq Ft

    115 Maple Ave, Goldsboro, MD 21636

    Step into this beautifully renovated Victorian home, nestled on a generous .55-acre lot. This 2048 sqft gem blends timeless architectural charm with contemporary updates, offering a perfect blend of classic style and modern comfort.The home features three spacious bedrooms on the second floor, complemented by two full bathrooms—one on each level. The freshly painted interior, along with

    Phill Whitby Long & Foster Real Estate, Inc.

    115 Maple Ave, Goldsboro, MD 21636
  • /7

    $199,000

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft

    306 Bernard Ave, Greensboro, MD 21639

    Step into this delightful home that perfectly blends comfort with convenience. The open-concept living and kitchen area creates an inviting space for relaxing or entertaining, complete with effortless flow and natural light. With two well-sized bedrooms and a full bathroom, it's ideal for small households or anyone seeking a cozy oasis. From the kitchen, step out onto the oversized back deck—your

    Amanda Morgan Brenton Realty Group

    306 Bernard Ave, Greensboro, MD 21639
  • /47

    $625,000

    • 3 Beds
    • 2 Baths
    • 1,616 Sq Ft

    300 S 1st St, Denton, MD 21629

    Peaceful Living on the Choptank River!!! One level Living! Offering 3 Bed and 1.5 Bath. Home features an open Floor Plan with Large Living Room w/ Gas Burning Stove., Spacious Kitchen with Tons of Storage, Breakfast Bar, and plenty of space for your Table and Chairs! Primary Bedroom facing the Water with Great Waterfront Views. Home also features a paved driveway with 2 door garage and a full

    Kathleen Brenton Brenton Realty Group

    300 S 1st St, Denton, MD 21629
  • /20

    $189,900

    • 3 Beds
    • 1 Bath
    • 1,904 Sq Ft

    21948 Main St, Hillsboro, MD 21641

    This home is high on a hill across from the Tuckahoe Creek with some winter views of the water. --the park across the street has a ramp for boats, kayaks, and canoes. The home has 3 bedrooms and a small room for office or nursery or whatever you want it to be;, and one full bath -- all upstairs. The front porch entrance opens to a foyer and the living room to the right and then the dining room

    Bonnie Duley Long & Foster Real Estate, Inc.

    21948 Main St, Hillsboro, MD 21641
  • /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
  • /55

    $429,900 Open Sat 12PM - 2PM

    • 5 Beds
    • 2 Baths
    • 4,060 Sq Ft

    8 W Liberty St, Ridgely, MD 21660

    Welcome to this beautiful updated Custom Built Brick 5-bedroom, 2-bath home nestled on a generous double corner lot in the quaint town of Ridgely. Combining classic charm with modern updates. This property offers comfort and convenience—perfect for growing families or those who love to entertain. Property hightlights include: Updated kitchen featuring brand-new stainless steel appliances, new

    Barbara Blosser Long & Foster Real Estate, Inc.

    8 W Liberty St, Ridgely, MD 21660
  • /17

    $380,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft

    106 Lednum Ave, Preston, MD 21655

    New construction in Preston, MD offering 3 bedrooms and 2 full baths across 1,400 square feet. This home features an open layout with vaulted ceilings, LVP flooring in the main living areas, and carpeted bedrooms. The kitchen is equipped with stainless steel appliances and granite countertops. The primary suite includes a stand-up shower, while the guest bath offers a tub/shower combo. An

    Eric Haro The Parker Group

    106 Lednum Ave, Preston, MD 21655
  • /18

    $99,000

    • 2 Beds
    • 2 Baths
    • 1,520 Sq Ft

    215 Academy Ave, Federalsburg, MD 21632

    This property offers an exceptional chance for a BRRRR investment, fix and flip opportunities or a DIY restoration project. Recent improvements, including partial window replacements and a newer roof, set the stage for a transformative renovation. The property features two bedrooms on the second floor, a bonus room, two bathrooms, a flex room, an enclosed front porch, large driveway and a fairly

    Nora Turner Long & Foster Real Estate, Inc.

    215 Academy Ave, Federalsburg, MD 21632
  • /5

    $140,000

    • Land
    • 3.75 Acres
    • $37,333 per Acre

    0 Burnt Mill Rd Unit MDCM2006056, Ridgely, MD 21660

    Discover the ideal blend of tranquil nature and prime location! 3.75 acres with mature trees, offering unparalleled privacy and peaceful country living in one of the area's most scenic subdivisions -- all just minutes away from Ridgely and Denton, and less than 1 mile from North Caroline High School. Build your dream home on this beautiful level building lot, providing an even terrain throughout

    Stephan Strothe Washington Fine Properties, LLC

    0 Burnt Mill Rd Unit MDCM2006056, Ridgely, MD 21660
  • /32

    $289,000

    • 3 Beds
    • 1 Bath
    • 1,392 Sq Ft

    6101 Bethlehem Rd, Preston, MD 21655

    Charming 3-bedroom, 1-bathroom mobile home on 1.37 acres with plenty of room to grow! This well-maintained, one-family-owned property boasts numerous recent upgrades, including a new roof (2024), hot water heater (2023), new appliances and countertops (2024), fresh paint (2024), new fencing (2024), and a brand-new septic system. The oversized 2-car garage provides ample storage or workspace.

    Katie Moore Coldwell Banker Chesapeake Real Estate Company

    6101 Bethlehem Rd, Preston, MD 21655
  • /26

    $299,000

    • 3 Beds
    • 2.5 Baths
    • 1,664 Sq Ft

    504 Pintail St, Greensboro, MD 21639

    Practically New Home in Greensboro, MD — Built in 2024!Why wait to build when you can move right into this stunning, barely lived-in home? Built in 2024 and meticulously maintained, this property offers the perfect blend of modern style and low-maintenance living.Step inside to an inviting open floor plan filled with natural light. The spacious kitchen features sleek granite countertops,

    Kaitlyn Collins Benson & Mangold, LLC

    504 Pintail St, Greensboro, MD 21639
  • /18

    $529,000

    • Land
    • 53.01 Acres
    • $9,979 per Acre

    0 Temple Rd Unit MDCM2006034, Marydel, MD 21649

    This ±53-acre timber property offers a blend of residential potential and quality recreational opportunity. The land features a mix of hardwood and pine stands in various age classes, with a healthy understory, topography changes, and seasonal wetland bottoms—ideal characteristics for managing whitetail deer and turkey habitat.The property consists of five separate parcels, four of which

    Benjamin Alder The Land Group

    0 Temple Rd Unit MDCM2006034, Marydel, MD 21649
  • /9

    $269,900

    • 3 Beds
    • 1.5 Baths
    • 1,584 Sq Ft

    3406 Rose St, Federalsburg, MD 21632

    Totally renovated doublewide. beautiful tile work,large kitchen. new foundation, electric, cacNew dry wall, flooring, roof, welland septic. New concrete pad in rear yard ready for new shed

    Barbara Nichols Results Realty Inc.

    3406 Rose St, Federalsburg, MD 21632
  • /2

    $30,000

    • 1 Bath

    12087 Wayman St, Ridgely, MD 21660

    Property is uninhabitable.

    Samantha Johnson Keller Williams Preferred Properties

    12087 Wayman St, Ridgely, MD 21660
  • /89

    $2,750,000

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

    28219 Bridgeville Rd, Federalsburg, MD 21632

    First time on the market! Discover a rare opportunity to own a 105± acre estate on Maryland’s beautiful Eastern Shore, Close to tax free shopping and the beaches. Designed by renowned California architect David Watson, the exterior of this home is one of the all-time most downloaded photos on the popular homebuilding and design website, Houzz. This one-of-a-kind property combines luxury living,

    Jim Corson Benson & Mangold, LLC

    28219 Bridgeville Rd, Federalsburg, MD 21632
  • /2

    $129,000

    • 6 Beds
    • 2 Baths
    • 2,400 Sq Ft

    321 S Main St, Federalsburg, MD 21632

    tenant occupied duplex rented for 1600/ month. agent is owner

    Bo Claggett Coldwell Banker Realty

    321 S Main St, Federalsburg, MD 21632
  • /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
  • /32

    $427,000

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

    26674 Bentley Place, Henderson, MD 21640

    You can still call this home by the end of the year for the holidays! If you're dreaming of peaceful country living, this beautiful home is the perfect retreat. Built in 2004 and lovingly maintained since 2006, it sits on a spacious 1.30-acre lot and features 4 bedrooms and 2.5 baths—just the right size for comfort and functionality. The first floor boasts gorgeous hardwood floors and an open

    Sally Fricke RE/MAX Solutions

    26674 Bentley Place, Henderson, MD 21640
  • /4

    $92,000

    • Land
    • 0.33 Acre
    • $278,788 per Acre

    162 Main St, Preston, MD 21655

    Anne Schmidt Long & Foster Real Estate, Inc.

    162 Main St, Preston, MD 21655
  • /9

    $89,000

    • Land
    • 3.05 Acres
    • $29,180 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 AS-IS

    Deborah Callahan Benson & Mangold, LLC

    10440 Burrsville Branch Rd, Denton, MD 21629
  • /62

    $775,000

    • 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, featuring a

    Crystal Smith RE/MAX Executive

    26943 Fueller Dr, Marydel, MD 21649
  • /80

    $749,900

    • 6 Beds
    • 4.5 Baths
    • 5,000 Sq Ft

    15184 Jarrell Rd, Goldsboro, MD 21636

    BACK ON THE MARKET.....,Buyer financing fell through. All inspections (Home, Well and Septic) have been completed and any and all issues addressed. OWNER SAY: "COME ON DOWN, LET'S MAKE A DEAL" The Possibilities are endless on this, serene 12.12 acres just ready and waiting for you to turn it into your dream. The Property includes a Beautiful 5000+ square foot home and a Massive Detached 60X42

    Leslie Fulford Mann & Sons, Inc.

    15184 Jarrell Rd, Goldsboro, MD 21636
  • /62

    $365,900

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

    1010 S 2nd St, Denton, MD 21629

    1010 S 2nd Street offers in-town living WITHOUT in-town Taxes!!! This home rests at the edge of town on 1.06 acres with mature plantings. This 3-bed 2-bath home boasts hardwood, LVP, and tile floors. A fireplace insert for the pellet stove for heat, while the seller uses the Hot water baseboard as a backup. Full basement for additional entertaining or storage. Screened-in porch overlooks

    Roger Boyce Chesapeake Real Estate Associates, LLC

    1010 S 2nd St, Denton, MD 21629
  • /54

    $595,000

    • 4 Beds
    • 2.5 Baths
    • 3,168 Sq Ft

    24766 Tribbett Cir, Ridgely, MD 21660

    Why wait months to build when you can start enjoying this meticulously built, and finely crafted contemporary farmhouse home right now? Situated on an .85 acre lot in the established community of Ashworth, this 2023 built, 3,168 square foot, 4 bedroom, 2.5 bath home contemporary farmhouse-style home blends rustic charm with contemporary elegance. The exterior features classic white siding,

    Barbara McCaffrey Redfin Corp

    24766 Tribbett Cir, Ridgely, MD 21660
  • /24

    $286,990 New Construction

    • 3 Beds
    • 2 Baths
    • 1,219 Sq Ft

    SULLIVAN Plan at Kinnamon Meadows, Greensboro, MD 21639

    The Sullivan is a charming 1,219-square-foot, cottage-style ranch home featuring three bedrooms, two bathrooms, and a one-car garage. Just off the foyer, two spacious guest bedrooms and a shared full bathroom offer comfort and privacy for family or visitors. The open-concept kitchen boasts stainless steel appliances, modern cabinetry, and an optional island with seating that is perfect for casual

    D.R. Horton Builder
    103 Park Ave Unit 36203275, Greensboro, MD 21639
  • /22

    $266,990 New Construction

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

    PERRY Plan at Kinnamon Meadows, Greensboro, MD 21639

    The Perry, a 1,059 square foot open concept cottage-style ranch home, offers two bedrooms and two bathrooms. 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 modern cabinetry, stainless steel appliances, a spacious peninsula

    D.R. Horton Builder
    103 Park Ave Unit 36203273, Greensboro, MD 21639
  • /3

    $276,990 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
  • /2

    $291,990 New Construction

    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft

    HELENA Plan at Kinnamon Meadows, Greensboro, MD 21639

    The Helena is an inviting 1,460 square foot cottage-style ranch home that offers four bedrooms, two bathrooms, and a one-car garage. The long, welcoming foyer of this home allows for the three guest bedrooms and guest bathroom to be separate from the living areas of the home. The oversized great room with an abundance of natural light is open to the kitchen making an ideal space to entertain or

    D.R. Horton Builder
    103 Park Ave Unit 36203274, 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
  • /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
  • /25

    $217,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,365 Sq Ft

    Jefferson Plan at Riverwalk Terrace, Federalsburg, MD 21632

    The Jefferson is an open-concept 1,365 square foot two-story townhome with three bedrooms and two and a half bathrooms. The first floor is spacious with a large, thoughtfully designed kitchen with ample cabinet space, stainless steel appliances, a storage closet, and a peninsula island with space for seating. The kitchen is open to the living and dining area providing your ideal entertainment

    D.R. Horton Builder
    100 Riverwalk Terrace Unit 36203297, Federalsburg, MD 21632
  • /51

    $525,000

    • 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
  • /55

    $899,900

    • 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
  • /2

    $440,000

    • Land
    • 44.74 Acres
    • $9,835 per Acre

    0 River Rd Unit MDCM2005824, Ridgely, MD 21660

    Secluded property comprised of 2 perc approved parcels totaling 44.74 acres. This property is a mix of mature timber, wooded marshland, a tidal pond and frontage on the Choptank River. More info and photos soon.Tax id # 0607014147 and # 0607002408

    Andrew Beaven Wright Real Estate

    0 River Rd Unit MDCM2005824, Ridgely, MD 21660

Showing Results 81 - 120, Page 3 of 4

How to Buy a Home How to Finance a Home How to Sell a Home