156

Caroline County MD Homes for Sale

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  • /22

    $359,900

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

    311 Kerr Ave, Denton, MD 21629

    Discover this beautifully updated 3-bedroom, 2-bath corner lot rancher in Denton, Maryland, offering style, comfort, and unbeatable convenience! This single-story gem features gorgeous bamboo flooring throughout, creating a warm and modern ambiance. The traditional floor plan gives the living room area with wood burning fireplace a perfect cozy space for relaxing. Step into the Eat in Kitchen

    Justin Damadio Iron Valley Real Estate Ocean City

    311 Kerr Ave, Denton, MD 21629
  • /100

    $319,900

    • 3 Beds
    • 1 Bath
    • 1,284 Sq Ft

    2766 Veterans Dr, Federalsburg, MD 21632

    ""PRICE REDUCTION"" *Attention, All "OUTDOOR ENTHUSIAST" are Welcome!!! This Unique Property is comprised of Multiple Deep Water Ponds loaded with a variety of fish making fishing TOP NOTCH and the back Woods loaded with Deer. Truly A Nature Lovers Dream, offers Peace & Tranquility, like no other, You can look long and hard and not find a property like this. This property has a gently rolling

    Barbara Beaudet Brenton Realty Group

    2766 Veterans Dr, Federalsburg, MD 21632
  • /39

    $229,990

    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft

    107 Smith St, Federalsburg, MD 21632

    A must see, updated + upgraded, 1-level, 3-bedroom,1.5-bath home with an open floorplan. Situated on a nice-sized yard, this welcoming home offers more than meets the eye. Handsome + durable luxury vinyl plank flooring, fresh paint, and updated fixtures throughout. Spacious living room with a bar and radiant countertops overlook the kitchen. Dining room with breakfast bar and sliding glass door.

    Brandon Brittingham EXP Realty, LLC

    107 Smith St, Federalsburg, MD 21632
  • /15

    $215,000

    • 2 Beds
    • 1 Bath
    • 1,040 Sq Ft

    26732 Idlewild Rd, Federalsburg, MD 21632

    Cute 2 bedroom one story on quiet street. Metal roof. One car garage. Large room off of the kitchen has lots of possibilities, along with the closed in back porch. Updated bathroom. New Andersen windows 2024. New mini Split 2021. Night Owl security with six working cameras. Seamless gutter 2025. Septic cleaned and inspected 2025. Close to nature trails and not far from the boat ramp. Just enough

    Michael Shipley Benson & Mangold, LLC.

    26732 Idlewild Rd, Federalsburg, MD 21632
  • /24

    $299,900

    • 3 Beds
    • 1.5 Baths
    • 864 Sq Ft

    26606 Idlewild Rd, Federalsburg, MD 21632

    Three Bedroom, 1 and a half bathrooms, located on a quiet county road. This house has been freshly painted inside and outside, new LVP flooring installed throughout the house, all interior doors have been replaced with white six panel doors and new light fixtures in each room. New washer/dryer and refrigerator installed, heat pump is 1 year old, and there is a 22 kw Generac generator as a backup

    Robert Bringman Long & Foster Real Estate, Inc.

    26606 Idlewild Rd, Federalsburg, MD 21632
  • /38

    $249,500

    • 3 Beds
    • 1.5 Baths
    • 1,565 Sq Ft

    206 N Academy St, Greensboro, MD 21639

    **Seller Motivated** Welcome home to 206 Academy Street — a beautifully updated 3-bedroom, 1.5-bath home in the heart of Greensboro. This charming property features a spacious living room and dining area, a large walk-in pantry, and a newly refreshed kitchen with brand-new cabinets (including a turnstyle corner cabinet), a new sink, and a stainless-steel dishwasher. A new refrigerator and stove

    Heather Branham The Parker Group

    206 N Academy St, Greensboro, MD 21639
  • /6

    $169,900

    • Land
    • 5.28 Acres
    • $32,178 per Acre

    0 5 281 Acres Schulyer Rd, Goldsboro, MD 21636

    Peaceful 5.281-Acre Wooded Homesite with Wildlife Pond Views.Discover the perfect blend of natural beauty and rural tranquility on this 5.281-acre perc-approved building lot, ready for your dream home. Nestled in a quiet country setting, this property offers a stunning overlook of a preserved wildlife pond, where geese, ducks, deer, and turkeys are frequent visitors—creating your own

    Brett Schrader Taylor Properties

    0 5 281 Acres Schulyer Rd, Goldsboro, MD 21636
  • /41

    $289,900

    • 4 Beds
    • 1.5 Baths
    • 2,820 Sq Ft

    306 S Main St, Federalsburg, MD 21632

    Step into timeless charm and modern comfort with this beautifully maintained -move in ready!-2,820 sq ft Victorian home, featuring 4 spacious bedrooms (freshly painted) and 1.5 baths. Nestled along the tranquil Marshyhope Creek, this waterfront retreat offers peaceful views and the rare opportunity to fish or kayak directly from your own private shoreline.Start your mornings with coffee on

    Mary Mabry Keller Williams Select Realtors of Cambridge

    306 S Main St, Federalsburg, MD 21632
  • /23

    $495,000

    • 0.5 Baths
    • 3,321 Sq Ft

    7 W Belle St, Ridgely, MD 21660

    Over 3,300 sq. ft. two-story building, constructed in 2006, offers endless potential with a little imagination. Currently a pharmacy, gift shop, and ice cream parlor, it could easily be transformed into a fantastic four-bedroom, 2.5-bath residence or adapted for other mixed-use purposes. Both levels feature open, flexible layouts—ready to be reimagined to suit your vision.Located in the

    Traci Jordan Meredith Fine Properties

    7 W Belle St, Ridgely, MD 21660
  • /56

    $320,000

    • 5 Beds
    • 3 Baths
    • 2,122 Sq Ft

    212 Main St, Preston, MD 21655

    ***Unique Opportunity***Welcome to this spacious and well-cared-for property located in the peaceful town of Preston. The main home offers 5 generously sized bedrooms and 3 full bathrooms, providing ample space for comfortable family living or multi-generational needs. A large eat-in kitchen serves as the heart of the home, perfect for everyday meals or entertaining guests.This

    Ross Muir EXP Realty, LLC

    212 Main St, Preston, MD 21655
  • /7

    $127,000

    • Land
    • 4.14 Acres
    • $30,676 per Acre

    0 Burnt Mill Rd Unit MDCM2006400, Ridgely, MD 21660

    Discover the ideal blend of tranquil nature and prime location! 4.14 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

    Stephan Strothe Washington Fine Properties, LLC

    0 Burnt Mill Rd Unit MDCM2006400, Ridgely, MD 21660
  • /20

    $244,900

    • 1 Bath

    11146 Branch Ct, Denton, MD 21629

    1.65 Acres with Well and Septic in Place!! 3 Bay Garage with one Pass-thru Unit - Features include - extra storage, Office, Kitchenette,and Full Bath. Come Build your Dream Home.!! Lot features U shape Driveway with Plenty of parking and nicely landscaped with mature trees. . Check with County for all your many possiblities! Conviently located with in minutes to Downtown Denton, Choptank River

    Kathleen Brenton Brenton Realty Group

    11146 Branch Ct, Denton, MD 21629
  • /46

    $797,500

    • 3 Beds
    • 2 Baths
    • 2,342 Sq Ft

    12618 Knife Box Rd, Greensboro, MD 21639

    Custom home built in 2007, this home features a large eat in kitchen, a lovely screened porch over looking the park like property. Living room featuring a fireplace, and tray ceiling. to add another cozy feature. Hard wood flooring through out the living space gives that warm welcoming vibe. The property has the potential to be off the grid, the geothermal system is the basis., and a wood stove

    Kat Thompson Benson & Mangold, LLC.

    12618 Knife Box Rd, Greensboro, MD 21639
  • /60

    $699,000

    • 3 Beds
    • 2 Baths

    28402 Liden School Rd, Denton, MD 21629

    Private serene living at its finest! This property has it all -- gorgeous rancher with 3 BR and 2 full baths; pantry in the kitchen, family room with pellet stove and brick fireplace that can burn wood; two large walk-in closets in primary bedroom; so much to mention here that you really must come see for yourself -- fresh air, peace and quiet, birds singing, wildlife, and more. Want horses; this

    Bonnie Duley Long & Foster Real Estate, Inc.

    28402 Liden School Rd, Denton, MD 21629
  • /24

    $218,000

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    218 E Sunset Ave, Greensboro, MD 21639

    This charming 3-bedroom, 1-bath home sits just across the street from the beautiful Choptank River, offering water views right from your doorstep. Enjoy the benefits of solar panels for lower energy costs.The property also includes a spacious 24’ x 28’ detached garage—perfect for vehicles, a workshop, or extra storage. Whether you’re looking for your first home or looking to downsize this

    Stevie Brummell Keller Williams Realty

    218 E Sunset Ave, Greensboro, MD 21639
  • /22

    $150,000

    • 4 Beds
    • 1.5 Baths
    • 2,668 Sq Ft

    208 N Main St, Federalsburg, MD 21632

    Traditional Victorian. 4 bedrooms, 1 1/2 baths, basement, attic, wraparound porch.Sold as is. Cash or conventional financing. Estate of Bonnie Jefferson.

    Barton Johnson/not int Marshy Hope Realty LLC

    208 N Main St, Federalsburg, MD 21632
  • /41

    $325,000

    • 3 Beds
    • 2.5 Baths
    • 1,364 Sq Ft

    406 Wood Duck Dr, Greensboro, MD 21639

    BACK ON THE MARKET! Buyers home sale contingency fell through days before settlement! This beautiful colonial, in the heart of Greensboro is one you don’t want to miss! Featuring a traditional two story floor plan, this home welcomes you from the start. This 3 bedroom, and 2.5 bathroom home offers a move in ready space to make your own! As you enter you’ll love the newer vinyl plank flooring

    Brittany Gough RE/MAX One

    406 Wood Duck Dr, Greensboro, MD 21639
  • /28

    $399,000 New Construction

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

    1 Sunrise Ave, Ridgely, MD 21660

    To Be Built, but you are able to do showings at the model home that is pictured NOW with renderings of the actual projected home in the first two photos. As you can see, Lomaxx Custom Homes puts effort into every detail. 3 Sunrise Ave will feature 4 bedrooms and 2.5 beautifully designed bathrooms. From the moment you step onto the brick steps of the front porch you'll notice the charm of the

    Crystal Smith RE/MAX Executive

    1 Sunrise Ave, Ridgely, MD 21660
  • /10

    $299,900

    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft

    21090 Marsh Creek Rd, Preston, MD 21655

    Amazing opportunity for a 1st time buyer or investor. The home has been recently renovated to include new kitchen cabinets, counter tops, appliances, flooring, ceiling fans, base board heating units, new windows and painting. The roof was replaced in 2024. The home is move in ready, just bring your furniture.

    Eddie Matthews Benson & Mangold, LLC

    21090 Marsh Creek Rd, Preston, MD 21655
  • /51

    $399,000

    • 3 Beds
    • 2 Baths
    • 2,016 Sq Ft

    14990 Greensboro Rd, Goldsboro, MD 21636

    Considerable Price Improvement! This property is being sold as/is to settle an estate. Bring your horse, goats, pigs and sheep. This 3 bedroom, 2 bath Cape has additional unfinished space on the second floor. Partially wooded with a fenced pasture and barn with 4 stalls. With a few upgrades and some TLC, this private home on 5+ acres could be your paradise.

    Andrew Beaven Wright Real Estate

    14990 Greensboro Rd, Goldsboro, MD 21636
  • /9

    $299,900

    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft

    21084 Marsh Creek Rd, Preston, MD 21655

    Amazing opportunity for a 1st time buyer or investor. The home has been recently renovated to include new kitchen cabinets, counter tops, appliances, flooring, ceiling fans, base board heating units, new windows and painting. The roof was replaced in 2024. The home is move in ready, just bring your furniture.

    Eddie Matthews Benson & Mangold, LLC

    21084 Marsh Creek Rd, Preston, MD 21655
  • /34

    $349,900

    • 3 Beds
    • 1 Bath
    • 1,104 Sq Ft

    26623 Bee Tree Rd, Henderson, MD 21640

    Outdoorsman’s Paradise on 4+ Acres! Discover your own private retreat with this beautifully updated countryside home, perfectly designed for comfort, adventure, and peaceful living. Recent upgrades include stylish and durable LVP flooring, a spacious, fully renovated bathroom, a fully encapsulated crawlspace, and a long-lasting metal roof for years of worry-free ownership. Love the outdoors? This

    Rick Parreco RE/MAX Executive

    26623 Bee Tree Rd, Henderson, MD 21640
  • /55

    $359,900

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

    26722 Sandtown Rd, Goldsboro, MD 21636

    Bring your horses! This 4 acre property nestled in small town Goldsboro has everything you need to make your very own farmette, live fencing & well maintained horse run ins with electric. Plenty of room to spread out in this country setting! This updated 3 bed 2 full bath rancher features a new roof & new flooring. Short drive to Denton, Greensboro, and the DE State Line for the commuter!

    Megan Rosendale Rosendale Realty

    26722 Sandtown Rd, Goldsboro, MD 21636
  • /35

    $273,000

    • 3 Beds
    • 2 Baths
    • 2,079 Sq Ft

    302 Kerr Ave, Denton, MD 21629

    Welcome to this delightful single-story ranch home tucked away on a nearly half‐acre lot in the heart of Denton. Built in 1958, this residence blends classic appeal with modern conveniences to offer a comfortable, relaxed lifestyle. Step inside to a warm, inviting living space anchored by a fireplace and enhanced by built-in shelving and generous windows. The kitchen is functional and connects

    Brian Jones Keller Williams Select Realtors of Annapolis

    302 Kerr Ave, Denton, MD 21629
  • /14

    $150,000

    • 2 Beds
    • 2 Baths
    • 640 Sq Ft

    26471 Three Bridges Rd, Federalsburg, MD 21632

    Opportunity awaits at 26471 Three Bridges Rd in Federalsburg, MD! This partially remodeled 2-bedroom, 2-bath home is ready for your finishing touch. Inside, the property has been taken down to the framing and subflooring, giving you a true blank canvas to bring your vision to life—whether you’re an investor looking for your next project or a buyer ready to customize every detail.Set on

    LEE MARLAND Keller Williams Realty

    26471 Three Bridges Rd, Federalsburg, MD 21632
  • /67

    $399,900

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

    1612 Cattail Commons Way, Denton, MD 21629

    Discover this charming home in the desirable Cattail Commons neighborhood. Lots of recent upgrades completed and ready for you to move-in. As you arrive, you will immediately notice the brand new white fence which is ideal for privacy and the cozy front porch for those days you wish to unwind. Open the door and you are greeted with an expansive and open floorplan with fresh paint throughout. To

    Daniel Register Northrop Realty

    1612 Cattail Commons Way, Denton, MD 21629
  • /51

    $639,000

    • 4 Beds
    • 4 Baths
    • 3,484 Sq Ft

    24324 Asbury Dr, Denton, MD 21629

    Lovely grand colonial with covered front porch located on almost 4 acres. The first floor offers a huge primary suite with walk in closet and bath with soaking tub, dual headed shower and double vanity.Dining room has gleaming hardwood floors with enough space to seat 20 people, lovely overhead chandelier and warming propane fireplace . Kitchen has all stainless appliances, plenty of

    Bonnie Johnson Keller Williams Realty

    24324 Asbury Dr, Denton, MD 21629
  • /2

    $274,990 New Construction

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

    123 Parkland Rd, Greensboro, MD 21639

    Explore 123 Parkland Road, 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 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

    Justin K Wood D.R. Horton Realty of Virginia, LLC

    123 Parkland Rd, Greensboro, MD 21639
  • /43

    $247,500

    • 3 Beds
    • 2 Baths
    • 1,684 Sq Ft

    207 Bloomingdale Ave, Federalsburg, MD 21632

    Discover this inviting 3-bedroom, 2-bath home on a 0.27-acre lot in the heart of Federalsburg. Enter to a spacious living room filled with natural light and a cozy fireplace, perfect for relaxing or entertaining. Adjacent, the family room features stunning wood-paneled walls, built-in shelving, a second fireplace, and access to both the outdoors and the kitchen and dining areas, creating a

    Dustin Parker The Parker Group

    207 Bloomingdale Ave, Federalsburg, MD 21632
  • /40

    $460,000

    • 3 Beds
    • 2.5 Baths
    • 1,816 Sq Ft

    320 N Main St, Greensboro, MD 21639

    Welcome to 320 N Main St in the quaint town of Greensboro, where you'll find a home that invites you to kick off your shoes and stay a while. This residence sits on a half-acre lot and features three bedrooms and 2.5 baths, offering an ideal balance of space, comfort, and style. The beautifully updated kitchen is ready for all your culinary adventures, boasting a five-burner gas range, stainless

    Karen Clark Clark & Co Realty, LLC

    320 N Main St, Greensboro, MD 21639
  • /90

    $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
  • /57

    $529,000

    • 4 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    7837 Shore Dr, Preston, MD 21655

    Two Johns – Charming Home in a Sought-After Waterfront CommunityNestled 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

    Eddie Matthews Benson & Mangold, LLC

    7837 Shore Dr, Preston, MD 21655
  • /3

    $135,000

    • Land
    • 0.69 Acre
    • $195,652 per Acre

    1005 Market St, Denton, MD 21629

    A Rare Opportunity to Purchase a General Commercial Lot located in Denton off the High Visibility Corners of Market & Gay St. A Multitude of permissible uses. Water and Sewer hook ups are available for additional fee. There are not any structures on this cleared .69 ac lot. A wonderful Opportunity for the Entrepreneur with a Vision....Hurry to snag this one...

    Barbara Beaudet Brenton Realty Group

    1005 Market St, Denton, MD 21629
  • /39

    $750,000

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

    7844 Shore Dr, Preston, MD 21655

    Enjoy the waterfront lifestyle with this one floor gem perched up on the banks of the Choptank River just 10 minutes from historic Denton. Relaxation and a connection with nature are easily achieved inside and outside of the home. Outdoor living areas are abundant with a private screened-in gazebo to sit back and enjoy the wildlife, winter deck to catch some rays, and a back patio with Choptank

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    7844 Shore Dr, Preston, MD 21655
  • /10

    $48,999

    • Land
    • 0.24 Acre
    • $204,162 per Acre

    0 Brooklyn Ave, Federalsburg, MD 21632

    Taylor McCartney VRA Realty

    0 Brooklyn Ave, Federalsburg, MD 21632
  • /66

    $479,900

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

    2570 Guard Rd, Federalsburg, MD 21632

    Welcome to this 3-bedroom, 2-bathroom home nestled on more than Eight acres of land, offering the perfect blend of comfort, space, and opportunity. The main level features a practical layout with three bedrooms, two full baths, and a warm, inviting living space. Upstairs, you’ll find an unfinished second story, a blank slate ideal for adding extra bedrooms, a bonus room, or a private retreat

    Thomas Burdett Keller Williams Realty

    2570 Guard Rd, Federalsburg, MD 21632
  • /14

    $279,000

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

    2697 Choptank Main St, Preston, MD 21655

    Charming Renovated Home in Choptank, Preston MD Additional Photos coming. This home is currently getting a fresh coat of interior paint, new appliances and updates coming. It will be turn key ready for you. Situated on a large double lot with mature landscaping. Don’t miss this beautifully completely renovated 2-bedroom, 2-bath home located in the quaint and peaceful community of

    Darlene Wheatley Benson & Mangold, LLC

    2697 Choptank Main St, Preston, MD 21655
  • /35

    $345,000

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

    25291 Calvert Dr, Greensboro, MD 21639

    Welcome to Passapae Landing community, where peace, privacy, and comfort come together! This beautiful maintained 3-bedroom, 2-full bathroom ranch style home offers 1,344 sq ft of easy, single level living on nearly 1/2-acre lot-and its ready for you to move right in! Step inside to a bright, inviting layout perfect for both everyday living and entertaining. the spacious living area flows into a

    Erene Katris Coldwell Banker Realty

    25291 Calvert Dr, Greensboro, MD 21639
  • /10

    $620,000

    • Studio
    • 3,600 Sq Ft

    310 Main St, Marydel, MD 21649

    Great Apartment Building investment opportunity, updated, and ready to go! The building includes three 2-bedroom, 1-bath units and one 3-bedroom, 1-bath unit — all with private entrances and separately metered utilities. A furnished office space adds additional potential for on-site management or rental income.Recent upgrades include: New well (less than a year old) with a 20-year warranty,

    Agent Photo

    Sharon Daugherty

    Keller Williams Realty Delmarva

    (410) 881-8824

    310 Main St, Marydel, MD 21649
  • /40

    $389,000

    • 4 Beds
    • 2.5 Baths
    • 2,138 Sq Ft

    1111 Trice Meadows Cir, Denton, MD 21629

    Welcome to 1111 Trice Meadows Circle in Denton, MD! PRICE REDUCEDThis charming 4-bedroom, 2-bath detached single-family home offers comfort, style, and convenience in the sought-after Trice Meadows community. Featuring an open and inviting floor plan, this home is perfect for both everyday living and entertaining.The spacious living room flows seamlessly into a modern kitchen,

    LaTanya Drayton United Real Estate Premier

    1111 Trice Meadows Cir, Denton, MD 21629

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