33

Caroline County MD Homes under $300,000

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  • /30

    $299,000

    • 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
  • /28

    $249,900

    • 3 Beds
    • 1 Bath
    • 1,080 Sq Ft

    6413 Reliance Rd, Federalsburg, MD 21632

    Nice 3 bedroom 1 bath Rancher with garage in quiet country setting. This one will not last long!!

    Blaine Williamson McClain-Williamson Realty, LLC

    6413 Reliance Rd, Federalsburg, MD 21632
  • /34

    $227,000

    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft

    27320 Chipmans Ln, Federalsburg, MD 21632

    Charming country rancher with peaceful farmland views! Welcome to 27320 Chipmans Lane in Federalsburg, MD—this quaint 3-bedroom, 1-bath home offers the perfect blend of comfort, updates, and rural tranquility. Situated on over 1/3 of an acre, this home features a beautifully updated bathroom, a newer roof (just a few years old), and a brand new well—providing peace of mind for years to come.

    Justin Pokrywka Taylor Properties

    27320 Chipmans Ln, Federalsburg, MD 21632
  • /31

    $280,000

    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft

    618 Academy Ave, Federalsburg, MD 21632

    Welcome home! This beautifully cared-for property offers small-town charm with big advantages — no town taxes and only a five-minute walk to the local elementary school. Sitting on a spacious 0.78-acre lot, you'll love the huge backyard, perfect for kids, pets, or backyard cookouts. The large circular driveway provides plenty of parking, and there’s even a storage shed for all your outdoor gear.

    Kaitlyn Collins Benson & Mangold, LLC

    618 Academy Ave, Federalsburg, MD 21632
  • /21

    $238,900

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

    103 Riverwalk Terrace, Federalsburg, MD 21632

    This is an opportunity to buy in the sold out community of Riverwalk Terrace. The owner stayed at the home a few times some of the appliances never used. Open floor plan 1365 square feet , 3 bedrooms and 2.5 baths easy living. Only 2 years young this unit feels like new, was never a rental barley lived in. also backs up to the woods the private side of the community. Another perk to this location

    Kat Thompson Benson & Mangold, LLC.

    103 Riverwalk Terrace, Federalsburg, MD 21632
  • /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

    $290,000

    • 2 Beds
    • 1 Bath
    • 1,056 Sq Ft

    12 N Maple Ave, Ridgely, MD 21660

    Seller has to find home of choice. 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

    Wes Russum Coldwell Banker Chesapeake Real Estate Company

    12 N Maple Ave, Ridgely, MD 21660
  • /24

    $239,900

    • 3 Beds
    • 2 Baths
    • 1,416 Sq Ft

    329 Maple Ave, Federalsburg, MD 21632

    Charming Rancher with Beautiful Upgrades! This well-maintained 3-bedroom, 2-bath home features beautiful hardwood floors, a spacious living room, and an inviting kitchen designed for both everyday living and entertaining. The kitchen boasts quartz countertops and ample workspace, perfect for cooking and gathering.Enjoy the convenience of a separate laundry room plus an additional storage room

    Mary Mabry Keller Williams Select Realtors of Cambridge

    329 Maple Ave, Federalsburg, MD 21632
  • /3

    $265,000

    • 2 Beds
    • 1 Bath
    • 1,092 Sq Ft

    10819 Greensboro Rd, Denton, MD 21629

    This home will be a Total Renovation in 2026. Consisting of 2 BR and 1 Bath. Situated on almost a half ac. Lovely back yard, and new Well.

    Barbara Beaudet Brenton Realty Group

    10819 Greensboro Rd, Denton, MD 21629
  • /36

    $249,900

    • 3 Beds
    • 3 Baths
    • 1,678 Sq Ft

    102 S Academy St, Greensboro, MD 21639

    Classic Charm Meets In-Town Living. Enjoy the luxury of space on this generous .34-acre lot, featuring a 3-bedroom home designed for both quiet mornings on the front porch and lively backyard BBQs. Inside, flow seamlessly from the bright & airy living room to the dining area and kitchen. With three full baths, a dedicated laundry room, and a storage-ready basement, the layout is as functional as

    Karen Clark Clark & Co Realty, LLC

    102 S Academy St, Greensboro, MD 21639
  • /31

    $259,900

    • 3 Beds
    • 1.5 Baths
    • 1,155 Sq Ft

    502 W Sunset Ave, Greensboro, MD 21639

    Renovated & Move-In Ready with Detached 2-Car Garage! Welcome to this beautifully updated 3-bedroom, 1.5-bath home where modern style meets everyday comfort. From the moment you step inside, you’ll notice the fresh, clean feel created by brand-new LVP flooring, recessed lighting, fresh paint throughout, and a completely renovated kitchen and bathroom designed with today’s buyer in mind.The

    Pamela Geib Long & Foster Real Estate, Inc.

    502 W Sunset Ave, Greensboro, MD 21639
  • /16

    $220,000

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

    115 Maple Ave, Goldsboro, MD 21636

    Classic character, generous space, and a beautiful backyard create a wonderful opportunity to bring new life to this charming property. Buyers will appreciate the timeless details, inviting layout, and the chance to transform the home with thoughtful updates. With a spacious layout and a setting buyers often love, this home offers a wonderful opportunity for someone ready to refresh and

    Sandra Bradley Keller Williams Select Realtors of Easton

    115 Maple Ave, Goldsboro, MD 21636
  • /16

    $245,000

    • 3 Beds
    • 2.5 Baths
    • 1,693 Sq Ft

    1204 Blue Heron Dr, Denton, MD 21629

    Come on in to explore this beautifully maintained 3-level home offering the perfect blend of modern convenince and comfortable living. This beauty features 3 spacious bedrooms and 2.5 baths, with an open floor plan that creates an inviting flow throughout the main living areas. The home has been thoughtfully updated with fresh paint, new appliances and more to ensure it's move-in ready for you.

    Carolyn A. Page Shore Results Realty

    1204 Blue Heron Dr, Denton, MD 21629
  • /23

    $227,000

    • 3 Beds
    • 1.5 Baths
    • 1,828 Sq Ft

    126 Maple Ave, Preston, MD 21655

    Step back in time with this early 1900s home. This home is full of character, from the detail in the trim work to the upper level 'porch.' This home offers great potential to be returned to the early 1900s with a little TLC and vision. Located in the heart of Preston, it is 15 minutes from historic Easton with all its amenities. Come take a look and see the vision.

    Marsha Tull Marshy Hope Realty LLC

    126 Maple Ave, Preston, MD 21655
  • /36

    $299,900

    • 3 Beds
    • 1.5 Baths
    • 1,791 Sq Ft

    309 N Main St, Greensboro, MD 21639

    This exquisite Colonial-style home, thoughtfully renovated in 2019, seamlessly blends classic charm with modern luxury. Spanning 1,791 square feet, this residence offers a warm and inviting atmosphere, perfect for creating lasting memories. Step inside to discover a beautifully designed interior featuring engineered luxury vinyl plank flooring that exudes elegance and durability. The heart of the

    Eddie Matthews Benson & Mangold, LLC

    309 N Main St, Greensboro, MD 21639
  • /24

    $269,900

    • 3 Beds
    • 2 Baths
    • 1,436 Sq Ft

    28241 Hickman Cannery Rd, Denton, MD 21629

    Welcome to 28241 Hickman Cannery Road, a refreshed two-story home in Denton, MD, blending classic charm with modern, low-maintenance updates. Luxury vinyl plank flooring runs throughout both levels, creating a cohesive, move-in-ready feel. The main level offers a bright living room, a flexible den ideal for a home office or family room, a spacious kitchen, dedicated laundry room, and a full

    Billy Mister Keller Williams Realty

    28241 Hickman Cannery Rd, Denton, MD 21629
  • /11

    $262,500

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

    408 Bernard Ave, Greensboro, MD 21639

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

    Daniel Hill Long & Foster Real Estate, Inc.

    408 Bernard Ave, Greensboro, MD 21639
  • /53

    $225,000

    • 3 Beds
    • 1.5 Baths
    • 2,817 Sq Ft

    22060 Main St, Hillsboro, MD 21641

    Needs Work. sold as is - large home in need of updating/TLC - 2-story 3 car garage

    Keith Brooks Thurston Wyatt Real Estate, LLC

    22060 Main St, Hillsboro, MD 21641
  • /35

    $249,900

    • 2 Beds
    • 1 Bath
    • 1,140 Sq Ft

    3540 Houston Branch Rd, Federalsburg, MD 21632

    Welcome to 3540 Houston Branch Rd. It was purchased in 2021 and has undergone extensive renovations. The interior was taken down to the studs. There is new drywall, flooring and sub flooring, a complete bath room, windows, kitchen cabinets, appliances and quartz counter tops. Even the electric was updated along with plumbing. Did I mention a new roof, well and septic system!! This is a perfect

    Eddie Matthews Benson & Mangold, LLC

    3540 Houston Branch Rd, Federalsburg, MD 21632
  • /24

    $269,000

    • 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
  • /40

    $235,000

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

    212 Main St, Preston, MD 21655

    Welcome to this spacious and beautifully maintained property nestled in the peaceful town of Preston. The main residence features 5 generously sized bedrooms and 3 full bathrooms, offering plenty of space for comfortable family living, guests, or multi-generational arrangements. At the heart of the home, you’ll find a large eat-in kitchen, perfect for gathering with family, hosting friends, or

    Ross Muir EXP Realty, LLC

    212 Main St, Preston, MD 21655
  • /43

    $239,900

    • 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
  • /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 kitchen cabinets. Luxury vinyl flooring will be installed in the Living Room first week of April. Updated bath vanities and many more updates. Recent updates; septic, heat pump and newer windows. Photos will be uploaded in mid April. It will

    Darlene Wheatley Benson & Mangold, LLC

    2697 Choptank Main St, 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
  • /2

    $225,000

    • Land
    • 0 Acre

    11920 Central Ave, Ridgely, MD 21660

    Priced for a quick sale! This great property offers over 16 acres of level land with frontage on three roads: Central Avenue, Henry Road, and Holly Plains Drive. Zoned R1, this lot presents endless possibilities—whether you're looking to hold, subdivide, or develop. Located just outside the Ridgely city limits and within close proximity to the town center, this property is ideally positioned for

    Sam Benkirane Proplocate Realty, LLC

    11920 Central Ave, Ridgely, MD 21660
  • /20

    $272,490 New Construction

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

    127 Hobbs St, Greensboro, MD 21639

    Discover a new home at 127 Hobbs Street in the Kinnamon Meadows community of Greensboro, MD. This home is soon to be under construction. This 1,059 square foot open concept cottage-style ranch home offers two bedrooms, two bathrooms, and a two-car driveway. A welcoming front porch leads you into the spacious living room that seamlessly flows into the kitchen, creating a perfect space for

    D.R. Horton Builder
    127 Hobbs St, Greensboro, MD 21639
  • /24

    $294,990 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

    $269,990 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

    $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
  • /2

    $298,990 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
  • 125 Hobbs St, Greensboro, MD 21639

    $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
  • /37

    $299,000 Coming Soon

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

    7192 American Corner Rd, Denton, MD 21629

    Coming Soon! 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

    Andrew Beaven Wright Real Estate

    7192 American Corner Rd, Denton, MD 21629
  • /2

    $215,000 Coming Soon

    • 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. The current tenant owns the appliances, possible to supply needed appliances for

    Kat Thompson Benson & Mangold, LLC.

    24876 Meeting House Rd, Denton, MD 21629
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