131

Caroline County MD Homes for Sale

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  • /2

    $359,000

    • 3 Beds
    • 2 Baths
    • 1,922 Sq Ft

    5026 Bethlehem Rd, Preston, MD 21655

    Totally renovated colonial offering nearly 2,000 sq ft of living space on a spacious 1/3-acre corner lot. Featuring 3, possibly 4 generous bedrooms and 2 full baths, this property showcases luxury vinyl plank flooring throughout. Enjoy privacy rear fencing and a large backyard—perfect for outdoor living. Ideal for a growing family and conveniently located close to Easton and Preston. This home is

    Linda Moore Long & Foster Real Estate, Inc.

    5026 Bethlehem Rd, Preston, MD 21655
  • /37

    $295,000 Open Sat 1PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 1,752 Sq Ft

    1106 Osprey Ln, Denton, MD 21629

    Welcome to 1106 Osprey Lane in Mallards Landing — a fantastic opportunity to own a spacious 4-bedroom, 2.5 bath home in one of Denton’s most desirable communities. While in overall average condition, it presents an excellent opportunity for cosmetic updates and improvements that can truly elevate the space. Fresh paint and new carpeting would go a long way in transforming the interior and

    Barbara McCaffrey Redfin Corp

    1106 Osprey Ln, Denton, MD 21629
  • /33

    $179,900

    • 3 Beds
    • 2 Baths
    • 1,078 Sq Ft

    221 Denton Rd, Federalsburg, MD 21632

    Priced to Sell! Welcome to this Fully Updated Colonial on a .37 Acre Lot, Offering Modern Finishes and Move-In Ready Comfort. The Home Features a Stunning Open Kitchen (2025 Remodel) with New Cabinets, Quartz Counters, Tile Backsplash, and Stainless Steel Appliances, Perfect For Cooking and Entertaining. Enjoy Remodeled Bathrooms, New Flooring, New Lighting, and Custom Interior Paint Throughout

    Matthew Altizer ANR Realty, LLC

    221 Denton Rd, Federalsburg, MD 21632
  • /6

    $439,000

    • 7 Beds
    • 4 Baths
    • 3,376 Sq Ft

    23267 Shady Oak Ln, Denton, MD 21629

    Welcome to 23267 Shady Oak Lane in Denton, MD — a prime investment opportunity with tremendous upside potential. Situated on a large, spacious lot, this property offers room to expand, reimagine, or create exceptional outdoor living space. Whether you're considering an addition, detached garage, workshop, garden, or simply maximizing the yard’s potential, the lot size adds significant value and

    Mike Cowan Coldwell Banker Realty

    23267 Shady Oak Ln, Denton, MD 21629
  • /43

    $375,000

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

    412 N Main St, Greensboro, MD 21639

    Rare Find! This 3-bedroom, 2-bath renovated rancher offers the perfect blend of space and charm on a sprawling 0.73 acre in-town lot. Spanning over 1,860 sq. ft. of updated living space, you’ll love the openess of the crisp, white kitchen that flows into a living-dining area anchored by a cozy wood-burning fireplace, the versatile bonus room/office and the entertainment-ready basement with a

    Karen Clark Clark & Co Realty, LLC

    412 N Main St, Greensboro, MD 21639
  • /8

    $120,000

    • 1 Bed
    • 1 Bath
    • 720 Sq Ft

    22464 Hillsboro Rd, Denton, MD 21629

    Investment Opportunity on 2.4± Acres with Expansion Potential Discover the possibilities on this 2.4± acre property featuring a 1 bed, 1 bath home including a 3-bedroom approved septic system already in place for future expansion or new construction. The well was replaced in 2013, offering added peace of mind. A detached sub-panel is installed and ready to support future building plans, making

    Shawn Moore Meredith Fine Properties

    22464 Hillsboro Rd, Denton, MD 21629
  • /39

    $525,000

    • 3 Beds
    • 2 Baths
    • 2,184 Sq Ft

    24111 Friendship Rd, Preston, MD 21655

    Welcome to 24111 Friendship Rd in Preston, MD, a beautifully maintained 3-bedroom, 2-bath rancher set on a peaceful 2-acre wooded lot. This classic home offers timeless brick accents, a large paved driveway, and a two-car attached garage, along with both a storage shed and a spacious storage building for added flexibility. Inside, you’ll find a formal living room and a formal dining room enhanced

    Billy Mister Keller Williams Realty

    24111 Friendship Rd, Preston, MD 21655
  • /13

    $479,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    11473 Holly Rd, Ridgely, MD 21660

    Brand New Rancher with massive Detached Garage sitting on OVER 2 acres!!! This home is ready for your touches! Get ready...this is one you don't want to pass by!

    Crystal Smith RE/MAX Executive

    11473 Holly Rd, Ridgely, MD 21660
  • /34

    $249,000

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft

    2451 Guard Rd, Federalsburg, MD 21632

    Highest and best by 2/23/2026 at 12pm. Charming 3-bedroom, 2-bath home set on a private 1.43+/- acre lot in a peaceful country setting. The property features a large pole barn with overhead door, plus multiple additional sheds and outbuildings. An excellent opportunity with endless potential.

    Alicia Gannon Dulin Benson & Mangold, LLC

    2451 Guard Rd, Federalsburg, MD 21632
  • /20

    $60,000

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft

    21182 Marsh Creek Rd, Preston, MD 21655

    Adorable and move-in ready 3BR/2BA single-wide home located in the quiet community of Prettyman Manor. A private driveway with parking for three cars sits just steps from the front door of your new home. Step inside to an inviting open floor plan with a spacious living room featuring a cozy wood-burning stove, and a well-equipped kitchen with plenty of cabinet and counter space, plus a double

    Shane Slacum VYBE Realty

    21182 Marsh Creek Rd, Preston, MD 21655
  • /2

    $275,000

    • Land
    • 0 Acre

    11920 Central Ave, Ridgely, MD 21660

    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 future growth. With

    Sam Benkirane Proplocate Realty, LLC

    11920 Central Ave, Ridgely, MD 21660
  • /4

    $399,999 New Construction

    • 4 Beds
    • 2 Baths
    • 1,800 Sq Ft

    210 W 2nd St, Ridgely, MD 21660

    Brand new. Zero honey-do list. Full peace of mind. Welcome to this newly constructed 4-bedroom, 2-bath home in Ridgely, where modern design meets small-town charm. If you’ve been waiting for that fresh-start feeling — this is it. Step inside to a bright, open layout designed for real life. The spacious living area flows seamlessly into the kitchen and dining space, creating the perfect setup for

    Kenneth Jester Coldwell Banker Realty

    210 W 2nd St, Ridgely, MD 21660
  • /15

    $450,000 Coming Soon

    • 5 Beds
    • 2 Baths
    • 2,000 Sq Ft

    111 Riverview Ln, Greensboro, MD 21639

    Charming Home situated on the Choptank River...Outdoor Familys & Fishing Enthusiasts here is an opportunity not to be missed! 4 Bedrooms/ 1Full Bath & 1/2 Bath make this home enjoyable for all. This home was built by the owner with love, attention to detail & quality materials & labor...now its yours to make your own. Three(3) parcels equaling approximately 1 acre...plenty of room for family

    John Howard Long & Foster Real Estate, Inc.

    111 Riverview Ln, Greensboro, MD 21639
  • /2

    $309,000 Open House 3/07

    • 4 Beds
    • 3.5 Baths
    • 2,640 Sq Ft

    1907 Blue Heron Dr, Denton, MD 21629

    Highly sought after large townhome in the desirable community of Mallard Landing in Denton, featuring almost double the square footage, and a rear deck off of the kitchen. Multi-generational living has a full bedroom and bath, as well as a large family room on the main floor. A few easy steps to the second floor brings you to a beautiful open kitchen, dining, and living room. The third floor

    Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    1907 Blue Heron Dr, Denton, MD 21629
  • /19

    $274,900 Coming Soon

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

    102 S Academy St, Greensboro, MD 21639

    Dreaming of a big yard with in-town perks....Nestled on a generous .34-acre lot, this 3-bedroom, 3-full bath home with large, airy rooms and a classice front porch is designed for both quiet relaxation and lively entertaining. The expansive, fenced-in yard is a true highlight, shaded by mature trees and ready for summer cookouts. While much improved in 2005, the home is ready for a refresh—bring

    Karen Clark Clark & Co Realty, LLC

    102 S Academy St, Greensboro, MD 21639
  • /4

    $99,000

    • Land
    • 0.21 Acre
    • $471,429 per Acre

    504 Central Ave, Ridgely, MD 21660

    .21-Acre Vacant Residential Lot in the Heart of Ridgely. Great opportunity to build within town limits! This Main Street vacant building lot is zoned residential with access to public water and sewer. Building specs and setbacks per town code. Walk to local shops, dining, and town amenities. Convenient street parking at the front of the lot or explore the option to build a garage from the rear

    Allie Harris Taylor Properties

    504 Central Ave, Ridgely, MD 21660
  • /17

    $195,000

    • 6 Beds
    • 1 Bath
    • 2,148 Sq Ft

    207 W Sunset Ave, Greensboro, MD 21639

    Welcome to 207 W Sunset Avenue, a well-located property in the heart of Greensboro, Maryland. Situated on a quiet residential street, this home offers convenient access to local shops, dining, schools, and parks, while maintaining the charm of a small-town setting. The property presents a solid opportunity for a primary residence, investment, or renovation project. With its established

    Holly Anderson Long & Foster Real Estate, Inc.

    207 W Sunset Ave, Greensboro, MD 21639
  • /93

    $5,250,000

    • 4 Beds
    • 2.5 Baths
    • 3,150 Sq Ft

    25056 E Cherry Ln, Greensboro, MD 21639

    Beautiful farmstead situated on 410± acres, featuring 355± acres of highly productive tillable ground with approximately 210± acres under irrigation. The irrigation system consists of two pivots supplied by well water, supporting efficient and reliable crop production. The property includes a very well-maintained two-story, custom home that offers comfort, space and functionality. The upper level

    Michael Davis Phoenix Real Estate

    25056 E Cherry Ln, Greensboro, MD 21639
  • /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
  • /26

    $359,900 Pre-Foreclosure

    • 4 Beds
    • 2.5 Baths
    • 2,118 Sq Ft

    118 Briarwood Cir, Denton, MD 21629

    It's NOT PERFECT - BUT IT COULD BE!!! Seller selling "AS-IS" "WHERE-IS" *Priced at least 40K Under Market!!! Add your own finishing touches to make this one yours... or just bask in the possible equity!!! One of the few in this subdivision with a BASEMENT!!! Seller just added NEW CARPET!! NEW PAINT!" Did I mention the walk-in closet?? How about the 3-piece rough-in in the basement? (Finish the

    Robert Brendel RE/MAX Components

    118 Briarwood Cir, Denton, MD 21629
  • /10

    $434,000 Coming Soon

    • 4 Beds
    • 2 Baths
    • 1,880 Sq Ft

    23116 Gilpin Point Rd, Preston, MD 21655

    A perfectly situated, water-oriented, turnkey, rancher with a piece of country is ready for your enjoyment. Produce your own vegetables, flowers or the like in the already established rear garden beds, collect your peaches, pears and other fruits from 8 fruit bearing trees. Start your plants early in an enclosed greenhouse/produce stand. A second greenhouse area is framed and ready for a canopy.

    Edward Cartwright Benson & Mangold, LLC

    23116 Gilpin Point Rd, Preston, MD 21655
  • /27

    $349,000

    • 3 Beds
    • 1.5 Baths
    • 1,622 Sq Ft

    207 S 7th St, Denton, MD 21629

    3BR, 1.5BA home on LARGE in town lot featuring Corian countertops, hardwood floors and built-in bookshelves. Enjoy a welcoming front porch and screened breezeway connecting a 2 car attached garage with additional lean-to storage. Roof replaced 2021. Full Walkout Dry basement with French drain and sump pump. Convenient in town location close to local amenities, all that is missing is your car in

    Amy Betts Coldwell Banker Realty

    207 S 7th St, Denton, MD 21629
  • /6

    $375,000

    • Land
    • 5.3 Acres
    • $70,755 per Acre

    0 Bloomingdale Ave Unit MDCM2006762, Federalsburg, MD 21632

    5.3 acre site on Bloomingdale Avenue, Federalsburg. Situated next to Dollar General, across from ProvidentState Bank and very near Royal Farm Store and McDonalds. Contains 3 parcels sold as a package. Publicutilities to the property. Shared access with Dollar General. C1 Commercial zoning allows a wide variety ofuses including: office, general business and professional uses, banks,

    Florence Adams SVN |Miller Commercial Real Estate

    0 Bloomingdale Ave Unit MDCM2006762, Federalsburg, MD 21632
  • /16

    $220,000

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

    115 Maple Ave, Goldsboro, MD 21636

    Offered below the January 2026 appraisal, creating a compelling value-add opportunity in today’s market. Victorian-style home with over 2,000 square feet on a 0.55-acre lot in established Goldsboro. Four true bedrooms, including a flexible first-floor bedroom ideal for multiple layout options. Fresh interior paint and new laminate flooring have already completed. Major system updates include a

    Sandra Bradley Keller Williams Select Realtors of Easton

    115 Maple Ave, Goldsboro, MD 21636
  • /4

    $20,000

    • Land
    • 0.5 Acre
    • $40,000 per Acre

    0 Nelpine Rd, Preston, MD 21655

    Discover a hidden gem on Nelpine Rd, a 0.50-acre property located in a small community just north of Preston off Harmony Road. This half-acre of vacant land is a blank canvas awaiting your vision. Whether you're a developer, an investor, or someone looking to build a personal sanctuary, this property offers limitless potential. Only 15 minutes to Choptank River, 20 minutes to Easton, under an

    ryan byrd Coldwell Banker Realty

    0 Nelpine Rd, Preston, MD 21655
  • /9

    $250,000

    • 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
  • /20

    $290,000

    • 2 Beds
    • 1 Bath
    • 1,426 Sq Ft

    1303 Fairfield Ct, Denton, MD 21629

    This charming ranch-style home in the Fairfield subdivision offers a blend of comfort and convenience. Built in 2003, the property features durable vinyl siding and a well-maintained exterior with a gutter system, sidewalks, and street lights enhancing the neighborhood's appeal. The 0.14-acre lot includes a private rear fenced yard, perfect for outdoor activities. Inside, the home boasts 1,426

    Tricia Wilson Wilson Realty & Staging LLC

    1303 Fairfield Ct, Denton, MD 21629
  • /102

    $1,395,000

    • 4 Beds
    • 3.5 Baths
    • 3,356 Sq Ft

    23296 Wilder Way, Denton, MD 21629

    Right out of HGTV! Custom Built in 2020, this 3,350+/- sq ft one-level home offers an abundance of amenities including high ceilings, 4 bedrooms, 3.5 Baths, large open floorplan with huge gourmet kitchen with quartz/ss appliances, separate pantry, family room with stacked stone gas fireplace. The Primary Bedroom is located at one end of the house and includes a large bath with double vanity,

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (410) 376-8486

    23296 Wilder Way, Denton, MD 21629
  • /31

    $379,900

    • 4 Beds
    • 2.5 Baths
    • 2,132 Sq Ft

    1107 Osprey Ln, Denton, MD 21629

    This well maintained 4 bedroom 2.5 bath home in the excellent community setting of Mallard Landing is ready for its new owners! This 2000 sq ft property features a partially fenced yard with a lovely patio/firepit area and plenty of room for gardening, fresh cabinets & counter tops, built in electric fireplaces throughout, new washer & dryer, oversized attached 2 car garage currently set up as a

    Megan Rosendale Rosendale Realty

    1107 Osprey Ln, Denton, MD 21629
  • /35

    $239,900

    • 4 Beds
    • 2.5 Baths
    • 1,756 Sq Ft

    515 Vaughn Ave, Greensboro, MD 21639

    This charming home in Cedar Run is set to shine with a major refresh in 2026, blending modern comforts with classic appeal. Spanning 1,756 sq. ft. , this end-of-row home offers a cozy atmosphere perfect for creating lasting memories. The spacious layout features an attached garage, providing convenience and ease. Nestled in a vibrant community, residents enjoy access to nearby parks, perfect for

    Chad Muse KD Realty Inc

    515 Vaughn Ave, Greensboro, MD 21639
  • /23

    $230,000

    • 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

    $319,900

    • 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
  • /51

    $325,000

    • 4 Beds
    • 2 Baths
    • 1,326 Sq Ft

    1203 Tuckahoe Ct, Denton, MD 21629

    Charming 4 bedroom, 2 bath cottage tucked away on a quiet cul-de-sac just minutes from downtown Denton. The first floor features a welcoming living room with LVP flooring, kitchen with updated appliances, two bedrooms, and a full bath. Upstairs, you’ll find two additional bedrooms and a second full bath, offering flexible living space. Outside enjoy a large, fenced-in backyard with a deck and

    Alicia Gannon Dulin Benson & Mangold, LLC

    1203 Tuckahoe Ct, Denton, MD 21629
  • /24

    $279,900

    • 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
  • /72

    $749,900

    • 3 Beds
    • 2 Baths
    • 2,676 Sq Ft

    12820 Porters Landing Rd, Greensboro, MD 21639

    The Ultimate Secluded Waterfront Retreat! Privately positioned along the Choptank River, this 12.43 acre waterfront property is surrounded by mature trees, open sky, and abundant natural beauty. The mostly wooded landscape offers privacy and tranquility, creating a peaceful escape that feels worlds away yet remains connected to the charm of Maryland’s Eastern Shore. Outdoor amenities elevate the

    Agent Photo

    Penny Hollis

    Keller Williams Select Realtors of Annapolis

    (410) 834-0596

    12820 Porters Landing Rd, Greensboro, MD 21639
  • /26

    $499,000

    • 4 Beds
    • 1.5 Baths
    • 2,320 Sq Ft

    11289 Gregg Rd, Denton, MD 21629

    Rare opportunity to purchase 19.1 acres with 2 dwellings, included property identified as 11285 Gregg Rd. Endless options to either rent one or have an in-law suite. It is said to have three septic systems, three electric services all on one property. Then main house which has the basement is in need of some remodeling, has 4 bedrooms and 1.1/4 baths, the remodling process has been started. The

    Kat Thompson Benson & Mangold, LLC.

    11289 Gregg Rd, Denton, MD 21629
  • /3

    $69,000

    • Land
    • 2.08 Acres
    • $33,173 per Acre

    0 Goldsboro Rd Unit MDCM2006720, Denton, MD 21629

    Beautiful 2.08 acre flat lot. Was approved for a potential mound system in 1991. All paperwork is included in the disclosures. Buyer to verify well and septic approval before closing.

    Toni Lynne Advance Realty, Inc.

    0 Goldsboro Rd Unit MDCM2006720, Denton, MD 21629
  • /2

    $32,500

    • Land
    • 0.69 Acre
    • $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
  • /54

    $425,000

    • 4 Beds
    • 2 Baths
    • 1,692 Sq Ft

    12658 Oakland Rd, Ridgely, MD 21660

    Right on the outskirts of the Historic Town of Ridgely Maryland you will find this fully remodeled 4 bedroom rancher on a beautiful acre of land. A fenced backyard perfect for your pets and or your small farm animal dreams! Plenty of room for a kitchen garden too! Inside you will find a recently remodeled open concept kitchen with large island that makes for a great workspace & great gatherings!

    John Cary Rosendale Realty

    12658 Oakland Rd, Ridgely, MD 21660
  • /19

    $50,000

    • Land
    • 0.37 Acre
    • $135,135 per Acre

    2 N Main St, Greensboro, MD 21639

    Cleared and ready for your vision! This 1/3+ acre in-town parcel offers the perfect canvas for your new build. Buyer to perform all due diligence with the Town regarding development requirements, including costs for water and sewer allocation.

    Karen Clark Clark & Co Realty, LLC

    2 N Main St, Greensboro, MD 21639

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