154

Caroline County MD Homes for Sale

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  • /13

    $259,900

    • 2 Beds
    • 1 Bath
    • 869 Sq Ft

    3644 Houston Branch Rd, Federalsburg, MD 21632

    Beautiful immaculate with open floor plan. chefs kitchen, stainlus steel appliances. Granit counters and island. New bathroom, cac with one car garage. 2 acres of land, 2 bedroomand den which could be third bedroom

    Barbara Nichols Results Realty Inc.

    3644 Houston Branch Rd, Federalsburg, MD 21632
  • /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
  • /87

    $2,995,000

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

    28219 Bridgeville Rd, Federalsburg, MD 21632

    Welcome to a rare opportunity to own a premier 105+/- acre agricultural estate combining modern comfort, income-producing farmland, and outstanding infrastructure. Ideally situated in a peaceful rural setting, this remarkable property features approximately 70± acres of fully irrigated, tillable land—perfect for high-yield row crops or specialty farming. At the heart of the farm sits a stunning

    Jim Corson Benson & Mangold, LLC

    28219 Bridgeville Rd, 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
  • /9

    $99,000

    • Land
    • 3.05 Acres
    • $32,459 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

    Deborah Callahan Benson & Mangold, LLC

    10440 Burrsville Branch Rd, Denton, MD 21629
  • /17

    $230,000 Open Sat 10AM - 12PM

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    218 E Sunset Ave, Greensboro, MD 21639

    Welcome to 218 E Main St Greensboro, MD. This home offers 3 bedrooms and 1 bath. Home has a large, dethatched garage and off-street parking. Located next to the public boat ramp, with easy access to local shopping and Delaware tax free shopping. This home is located in a flood zone and is being sold as is. Sellers are offering $5,000 in closing assistance with acceptable offer!

    Dawn Williams Berkshire Hathaway Homeservice Homesale Realty

    218 E Sunset Ave, Greensboro, MD 21639
  • /42

    $239,000

    • 3 Beds
    • 2 Baths
    • 1,212 Sq Ft

    102 Roe St, Greensboro, MD 21639

    This 3-bedroom, 2-bath bungalow offers the perfect blend of warmth, space, and character. Set on a quiet street just minutes from downtown Greensboro. Step inside to a bright, welcoming living area and enjoy the comfort of a wood stove that keeps the whole house cozy during the winter months.The layout offers flexibility with three comfortable bedrooms and two full baths, providing just

    Jillian Luna Rosendale Realty

    102 Roe St, Greensboro, MD 21639
  • /18

    $169,900

    • 2 Beds
    • 1 Bath
    • 700 Sq Ft

    601 Cedar Ln, Greensboro, MD 21639

    Nice location out of town on 4 Acres, Carport/Canopy, 2 Bedrooms, one bath house, close to town, nice enclosed porch, large front and back yard, two outbuildings, horseshoe driveway

    Diane Wenk Wright Real Estate

    601 Cedar Ln, Greensboro, MD 21639
  • /10

    $249,000

    • Land
    • 0.23 Acre
    • $1,082,609 per Acre

    520 S 5th Ave, Denton, MD 21629

    LET’S MAKE A DEAL***INVEST IN A PRIME MULTI USE SITE * DESIRABLE LOCATIONS * BUYERS CHOICEDEVELOP NOW? Or HOLD AND LET TIME INCREASE YPUR PROFIT OPPORTUNITY.... FOUR 10,000 SQ FT ADJOINING LOTS IN A GREAT IN TOWN SETTING S DUPLEX. IS ONE OF SEVERAL PERMITTED USES SO EASILY to build total 8 UNITS. Office, Shop or Studio with 2nd floor Residential for a Live Work

    Phil Riordan Meredith Fine Properties

    520 S 5th Ave, Denton, MD 21629
  • /13

    $79,900

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    27980 Ruritan Rd, Denton, MD 21629

    CALLING ALL INVESTORS! This property in Denton is the one you have been waiting for! This one will not last! This Property is being sold As-Is condition. Buyer is responsible for all certifications. Seller never occupied. Neither the seller or listing agent make any representation as to the accuracy of any information contained herein. Buyer must conduct their own due diligence, verification,

    Megan Carpenter Tesla Realty Group, LLC

    27980 Ruritan Rd, Denton, MD 21629
  • /4

    $35,000

    • 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
  • /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
  • /5

    $247,000

    • 2 Beds
    • 1.5 Baths
    • 1,458 Sq Ft

    116 Maple Ave, Preston, MD 21655

    Small town location and close to SO many amenities - enjoy the best of both worlds! Great location in town and just around the corner from stores, restaurants, elementary school and more. Water access isn't too far away (about 5 minutes, if that!). The seller has done many updates since purchasing 3 years ago -- all new appliances, windows, front door, landscaping, refreshed painting throughout

    Mary Haddaway Benson & Mangold, LLC

    116 Maple Ave, Preston, MD 21655
  • /51

    $575,000

    • 3 Beds
    • 3.5 Baths
    • 2,667 Sq Ft

    22408 Hog Creek Rd, Preston, MD 21655

    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 the main

    James Bent Benson & Mangold, LLC

    22408 Hog Creek Rd, Preston, MD 21655
  • /55

    $975,000

    • 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
  • /83

    $995,500

    • 4 Beds
    • 3 Baths
    • 2,119 Sq Ft

    23274 Holly Park Dr, Preston, MD 21655

    Come Experience Waterfront Living Like Never Before on the Choptank River! Welcome to “One Sweet World", where breathtaking sunsets and expansive sky views await you just 50 feet from the river’s edge. This extraordinary waterfront retreat features a beautifully designed 2-bedroom, 2-bathroom main house, complemented by a cozy 2-bedroom, 1-bathroom guest house and a separate guest room/tackle

    Rick Parreco RE/MAX Executive

    23274 Holly Park Dr, Preston, MD 21655
  • /106

    $580,000

    • 4 Beds
    • 3 Baths
    • 3,039 Sq Ft

    8534 Briar Patch Dr, Denton, MD 21629

    Welcome to 8534 Briar Patch Drive. This very well maintained home has so much to offer. This beautifully maintained property offers four spacious bedrooms and three bathrooms, providing ample space and comfort for family living or entertaining guests. The main floor includes a foyer, living room, formal dining room, family room, living room, kitchen, sunroom, and a breakfast nook that

    Alana Taylor Worthington Realty Group, LLC

    8534 Briar Patch Dr, Denton, MD 21629
  • /6

    $199,900

    • Land
    • 4.00 Acres
    • $49,975 per Acre

    12316 Ridgely Rd, Ridgely, MD 21660

    BUILD YOUR DREAM HOME IN HISTORIC RIDGELY, MARYLANDNestled just outside the charming town of Ridgeley, this expansive 4-acre parcel offers a unique opportunity to create your custom retreat amidst the rich tapestry of Maryland's Eastern Shore. Ridgeley, often referred to as the ' Dream City', was meticulously planned in 1867 during the post -Civil War railroad boom. Though the grand vision of a

    Gary Lucks Keller Williams Realty

    12316 Ridgely Rd, Ridgely, MD 21660
  • /4

    $345,000

    • Studio
    • 2,260 Sq Ft

    517 W Sunset Ave, Greensboro, MD 21639

    Three unit apartment building. Two 1bedroom apartments, one 2 bedroom. Fully leased with positive income to support expense and debt service

    Randy Staats Benson & Mangold, LLC

    517 W Sunset Ave, Greensboro, MD 21639
  • /25

    $259,000

    • Studio
    • 1,820 Sq Ft

    207 Gay St, Denton, MD 21629

    Price Improvement! Great investment. Perfect opportunity for an investor or owner-occupied duplex as first floor unit generates $1100/month and second floor unit is currently vacant.Conveniently located, multi-family in Downtown Denton with the Denton Police Department directly across the street.Vinyl siding, replacement windows, ductless mini split HVAC and off-street parking in the rear.

    Andrew Beaven Wright Real Estate

    207 Gay St, Denton, MD 21629
  • /10

    $195,000

    • Land
    • 15 Acres
    • $13,338 per Acre

    12837 Ridgely Rd, Greensboro, MD 21639

    14.62 acres of privacy, nature, and waterfront access. This wooded recreational lot offers — a serene wooded 14.62 acre escape surrounded by the Choptank River.This vacant property is perfect for hunting, camping, kayaking, and outdoor enjoyment. The woods offer access for hiking, exploring, and wildlife watching — including deer, turkeys, and geese. This lot is not perc approved and has no

    Melissa Tippett TTR Sotheby's International Realty

    12837 Ridgely Rd, Greensboro, MD 21639
  • /31

    $290,000

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

    202 Maryland Ave, Ridgely, MD 21660

    INCREDIBLE VALUE! Looking for a well maintained and move-in ready home with no HOA?! Look no further - this home is just awaiting your personal touch, and you can move in with peace of mind with the one-year home warranty the sellers are offering to the new buyer! Situated on a corner lot, 202 Maryland Avenue comes with a large back yard - perfect for entertaining, gardening, or turning into your

    Mikeshia Wilson Chesapeake Real Estate Associates, LLC

    202 Maryland Ave, Ridgely, MD 21660
  • /24

    $153,000

    • Land
    • 3.00 Acres
    • $51,000 per Acre

    0 Asbury Dr, Denton, MD 21629

    Discover your ideal homesite in the scenic Asbury on the Choptank community, where peaceful living meets convenient access. This expansive 3-acre lot is perc approved for a three-bedroom septic system.Within this sought-after community, residents enjoy well-maintained roads, a private nature trail, and exclusive access to a community deepwater dock on the Choptank River. Ideal for boating

    Coard Benson Benson & Mangold, LLC

    0 Asbury Dr, Denton, MD 21629
  • /63

    $499,900

    • 3 Beds
    • 3 Baths
    • 2,645 Sq Ft

    14957 Cherry Ln, Ridgely, MD 21660

    Welcome to 14957 Cherry Ln. This property offers a pond and an in-ground pool. Large 2.5 acre lot. Home is over 2600 sq. ft. with the entire upstairs set-up as a primary suite with deck overlooking both the front and rear yard. Downstairs offer a large living area with kitchen and 2 additional bedrooms with 2 full baths. Oversized garage offer ample storage for all your toys. Pool liner was

    Eddie Matthews Benson & Mangold, LLC

    14957 Cherry Ln, Ridgely, MD 21660
  • /74

    $1,213,650

    • Land
    • 135 Acres
    • $9,000 per Acre

    0 Marblehead Rd, Ridgely, MD 21660

    Your Eastern Shore Hunting Legacy Awaits on Marblehead Road!Presenting 134.85 +/- acres of prime hunting land nestled on Marblehead Road in Ridgely, Maryland – a true Hunter's Paradise poised to deliver unforgettable adventures and a lifetime of cherished memories.Imagine stepping onto your own expansive tract, meticulously crafted by nature for the avid sportsman. This property

    Dale Hunter Bayside Realty

    0 Marblehead Rd, Ridgely, MD 21660
  • /3

    $30,000

    • Land
    • 0.50 Acre
    • $60,000 per Acre

    0 Gadow Rd, 4, Preston, MD 21655

    Tucked away in the heart of Caroline County, this -acre parcel of raw land in Preston, Maryland offers an affordable opportunity to create your perfect escape or future investment. Whether you're dreaming of a peaceful rural retreat, a new build, or simply a spot to call your own, this lot is a blank canvas full of potential. Why Preston? Living in Preston means enjoying a small-town, rural

    Lisa Longest Realty Navigator

    0 Gadow Rd, 4, Preston, MD 21655
  • /20

    $2,225,000

    • 3 Beds
    • 2 Baths

    16255 Jackson Ln, Goldsboro, MD 21636

    Incredible opportunity to own approximately 204± acres spanning Delaware and Maryland, featuring a charming 3-bedroom, 2-bath home with hardwood floors, a custom kitchen with island, dining room, living room with wood-burning stove, and a covered back porch. The property includes two large outbuildings with electric—a 30' x 105' four-bay building and a 30' x 50' three-bay pole building—along with

    Timothy Caropreso Keller Williams Realty Delmarva

    16255 Jackson Ln, Goldsboro, MD 21636
  • /20

    $2,225,000

    • 3 Beds
    • 2 Baths

    16255 Jackson Ln, Goldsboro, MD 21636

    Incredible opportunity to own approximately 204± acres spanning Delaware and Maryland, featuring a charming 3-bedroom, 2-bath home with hardwood floors, a custom kitchen with island, dining room, living room with wood-burning stove, and a covered back porch. The property includes two large outbuildings with electric—a 30' x 105' four-bay building and a 30' x 50' three-bay pole building—along with

    Timothy Caropreso Keller Williams Realty Delmarva

    16255 Jackson Ln, Goldsboro, MD 21636
  • /7

    $65,000

    • Land
    • 0.58 Acre
    • $112,069 per Acre

    205 New St, Goldsboro, MD 21636

    Currently home on the lot. DO NOT ENTER. Value in the land. This 0.57-acre corner lot in Goldsboro offers a great opportunity for new construction. Property is ready to be tapped into Town of Greensboro's Sewage. Existing well on site, (condition unknown, not hooked up) Current home allows per Planning and Zoning no Excise tax on next build. Permits for new construction to be applied through

    Roger Boyce Chesapeake Real Estate Associates, LLC

    205 New St, Goldsboro, MD 21636
  • /4

    $169,500

    • Land
    • 10 Acres
    • $16,314 per Acre

    PARCEL 91 Cool Spring Rd, Marydel, MD 21649

    Ready for you to build your new home! This beautiful lot is already perc tested for a 3-bedroom home. The woods are a great habitat for deer and turkey and other wildlife. This lovely lot is all ready for the new owner to apply for home construction as the buyer has had the survey completed with the SRA noted on it so lots of the necessary paperwork is complete. So come see and come buy and

    Bonnie Duley Long & Foster Real Estate, Inc.

    PARCEL 91 Cool Spring Rd, Marydel, MD 21649
  • /38

    $630,000

    • Studio
    • 3,600 Sq Ft

    310 Main St, Marydel, MD 21649

    Great Investment Opportunity Available Now!!! This Apartment Building is a Turn-Key Investment with 4 Large Apartments that are currently Occupied, and a Furnished Office on half an Acre of property. There are 3 - Two Bedroom/One Bathroom Units, and 1 - Three Bedroom/One Bathroom Unit. All units have separate entrances & meters, Assigned Tenant Parking & Handicapped Space. Potential Rental

    Christopher Sidoriak Keller Williams Flagship

    310 Main St, Marydel, MD 21649
  • /71

    $1,150,000

    • 4 Beds
    • 3.5 Baths
    • 4,092 Sq Ft

    8816 Dorothy Ln, Denton, MD 21629

    Nestled on over six acres of pristine land with direct access to the Choptank River, this contemporary waterfront estate offers the ultimate in Eastern Shore luxury living. Designed to impress, the home features four spacious bedrooms, three and a half baths, and soaring cathedral ceilings that crown a dramatic two-story living room with floor-to-ceiling windows—flooding the home with natural

    Dustin Parker The Parker Group

    8816 Dorothy Ln, Denton, MD 21629
  • /28

    $359,000

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    208 Oriole Ave, Ridgely, MD 21660

    Come see this Beautiful well maintained Ranch home in the heart of Ridgely. The house is a block away from the local park. The house has had many upgrades including an addition in 2020. New siding in 2020. New deck after 2020. New windows in 2017. There are solar panels on the roof. Spacious back yard with a patio. Many other upgrades to come and see.

    Rachel Penska Long & Foster Real Estate, Inc.

    208 Oriole Ave, Ridgely, MD 21660
  • /22

    $540,000

    • Land
    • 63 Acres
    • $8,550 per Acre

    0 Dover Bridge Rd Unit MDCM2005586, Preston, MD 21655

    63 Acre parcel located on Dover Bridge Road, just 4 miles to Preston and 7.5 miles to Easton. The property is perc-approved for residential use and there is a forestry management plan attached in the documents section explaining that 58 acres was timbered in 2008 and reforested with Loblolly Pine in 2009 with several acres around the perimeter remaining in hardwoods. The interior of the parcel

    Coard Benson Benson & Mangold, LLC

    0 Dover Bridge Rd Unit MDCM2005586, Preston, MD 21655
  • /15

    $319,900

    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft

    506 Pintail St, Greensboro, MD 21639

    Nearly new ranch style home with large front porch. Three bedrooms and two full baths plus spacious laundry room enhance this home. Large kitchen with center island with stainless appliances and granite countertops are a focal point of this open floor plan. Move in ready and waiting for a new family!

    Bonnie Johnson Keller Williams Realty

    506 Pintail St, Greensboro, MD 21639
  • /11

    $239,000

    • 4 Beds
    • 3 Baths
    • 1,190 Sq Ft

    210 Denton Rd, Federalsburg, MD 21632

    JUST REDUCED, WHAT A DEAL!Square footage is not reflected correctly, please confirm square footage the estimate is 1190. This listing including , the adjacent lot (property ID-05-0159272). Charming 4 bedroom, 3 full bath home sits up on a hill over looking open space. The kitchen and living area are a nice open floor plan, with a bonus area for reading or office area. Up-date kitchen

    Kat Thompson Benson & Mangold, LLC.

    210 Denton Rd, Federalsburg, MD 21632
  • /28

    $180,000

    • 2 Beds
    • 1 Bath
    • 700 Sq Ft

    213 W Central Ave, Federalsburg, MD 21632

    Large Lot! Must See if you are looking for a bit of privacy with in-Town living and a VERY Large Shop; insulated steel building with electric and 2 bays behind the house (separate meter). Great for small business owner shop or hobbyist. Cottage style home, 2 bedrooms, 1 bath, Open Floor plan to living room. Close to waterfront for fishing or access to the Trail. Whether its your first home,

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    213 W Central Ave, Federalsburg, MD 21632
  • /10

    $172,500

    • Land
    • 1.01 Acres
    • $170,792 per Acre

    707 W Sunset Ave, Greensboro, MD 21639

    Several individual parcels on Sunset, Cosden and Harold Streets. One parcel has a large 50' x 70' Morton style building, town water and sewer are available. The offering does seem to have some ownership of another parcel consisting of Cosden St. Any interested buyer should perform their own suitable level of due diligence.

    BRIAN MORRIS The Land Group

    707 W Sunset Ave, Greensboro, MD 21639
  • /56

    $295,000

    • 3 Beds
    • 2 Baths
    • 1,508 Sq Ft

    4972 Preston Rd, Federalsburg, MD 21632

    Welcome home to this beautifully renovated Cape Cod style 3-bedroom, 2-bathroom gem on 0.96 acres. This home has been thoughtfully updated with modern features while maintaining its cozy charm. Step inside to find brand-new LVP flooring, complemented by fresh lighting fixtures that brighten the space. The upgraded kitchen features new cabinetry, quartz countertops, a kitchen island, and new

    Jon Fleming Weichert Realtors - Blue Ribbon

    4972 Preston Rd, Federalsburg, MD 21632
  • /49

    $899,000

    • Land
    • 187 Acres
    • $4,807 per Acre

    0 Cool Spring Rd Unit MDCM2005520, Marydel, MD 21649

    Cool Spring Sporting Property is approximately 187+/- acres.  The Perpetual Deed of Easement calls for 182 acres of the parent deed to be enrolled in conservation with an additional 5+/- acre field left out of the Easement. Located south of Marydel, MD in the village of Henderson, the land runs North and South along Cool Spring Road and North to Northeast along Marvel Road. In 2009, the landowner

    Benjamin Alder The Land Group

    0 Cool Spring Rd Unit MDCM2005520, Marydel, MD 21649

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