177

Caroline County MD Homes for Sale

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  • /43

    $245,000

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

    207 Bloomingdale Ave, Federalsburg, MD 21632

    Discover this inviting 2-bedroom, 1-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
  • /3

    $99,900

    • 3 Beds
    • 2 Baths
    • 2,312 Sq Ft

    9709 Foy Rd, Denton, MD 21629

    Priced To Sell Fast! Investor Alert! Renovate & Resell, Buy and Hold or Tear Down and Develop. Major Rehab Needed, City Will Require Permits. Per the City Lot Can be Split into 3 Parcels. 1.72 Acres Total. 3 Level Colonial, Spacious Kitchen, Spacious Bedrooms, Hardwood Floors, Much More!! Just Waiting For Your Personal Cosmetics and Renovations to Make it Shine. Close to Schools, Shopping and

    Matthew Altizer ANR Realty, LLC

    9709 Foy Rd, Denton, MD 21629
  • /90

    $849,000

    • 3 Beds
    • 4 Baths
    • 2,756 Sq Ft

    4 S 1st St, Denton, MD 21629

    Outstanding Residential OR Business Opportunity! Rare Find with-in Downtown Denton! Property would make an excellent Restaurant, Bar, or great for Venues. 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! Full list of Current

    Kathleen Brenton Brenton Realty Group

    4 S 1st St, Denton, MD 21629
  • /60

    $227,900

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

    206 N Academy St, Greensboro, MD 21639

    Charming 3-bedroom, 1.5-bath colonial in the heart of Greensboro, walking distance to Ober Park. Home features beautifully updated bathrooms, new LVP flooring on the main level and in baths, and fresh paint throughout. Kitchen will soon include brand-new cabinets. Exterior has been refreshed with attractive landscaping and newly painted siding. A 2-car detached garage adds extra storage and

    Heather Branham The Parker Group

    206 N Academy St, Greensboro, MD 21639
  • /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
  • /25

    $265,900

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    113 Boyce Mill Rd, Greensboro, MD 21639

    Enjoy the convenience of the short distance to jump onto 313 , yet a quiet location away tucked in the country side. House built in 2007 this well maintained home is waiting for the next owner. Open floor plan, the kitchen has ample room to be an eat in kitchen. Enter the home and you walk into the living room off the front porch. All living on one level makes this an easy home to navigate.

    Kat Thompson Benson & Mangold, LLC.

    113 Boyce Mill Rd, Greensboro, MD 21639
  • /2

    $20,000

    • Land
    • 0.7 Acre
    • $28,571 per Acre

    Parcel 210 Dover Bridge Rd, Preston, MD 21655

    Unimproved lot on Dover Bridge Rd. No perc on the property currently. Close to Easton and Preston. Partially cleared, seller offering to clear remaining tree stumps.

    Katie Stecklair Cross Street Realtors LLC

    Parcel 210 Dover Bridge Rd, Preston, MD 21655
  • /6

    $279,000

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

    2697 Choptank Main St, Preston, MD 21655

    Charming Renovated Home in Choptank, Preston MD Situated on a large double lot with mature landscaping. Don’t miss this beautifully renovated 2-bedroom, 2-bath home located in the quaint and peaceful community of Choptank. Every inch of this home has been thoughtfully updated from top to bottom, blending modern finishes with classic Eastern Shore charm.Currently tenant-occupied and

    Darlene Wheatley Benson & Mangold, LLC

    2697 Choptank Main St, Preston, MD 21655
  • /13

    $190,000

    • Land
    • 16.36 Acres
    • $11,614 per Acre

    0 Oakland Rd, Ridgely, MD

    Discover a unique opportunity to own two adjacent parcels on Oakland Road in beautiful Caroline County. This offering includes 16.36-acres identified as Tax Map 0009, Parcel 103, Grid 0023....Note there is an Additional Separate Parcel that is adjacent with 1.0 acres, listed in MLS: MDCM2006238 for sale, identified as Tax Map 0009, Parcel 63, Grid 0023.....Together, these properties provide ample

    Sandra Gendleman Long & Foster Real Estate, Inc.

    0 Oakland Rd, Ridgely, MD
  • /8

    $25,000

    • Land
    • 1 Acre
    • $25,000 per Acre

    0 Oakland Rd, Ridgely, MD

    Discover a unique opportunity to own two adjacent parcels on Oakland Road in beautiful Caroline County. This offering includes 1.0-acre identified as Tax Map 0009, Parcel 63, Grid 0023....Note there is an Additional Separate Parcel that is adjacent with 16.36 acres, listed in MLS: MDCM2006238 for sale, identified as Tax Map 0009, Parcel 103, Grid 0023.....Together, these properties provide ample

    Sandra Gendleman Long & Foster Real Estate, Inc.

    0 Oakland Rd, Ridgely, MD
  • /5

    $199,000

    • Land
    • 6.45 Acres
    • $30,853 per Acre

    Lot 1 Dover Bridge Rd, Preston, MD 21655

    The perfect setting for your dream home on this 6.446-acre perc-approved buildable lot, ideally located between Preston and Easton. Offering both space and convenience, this property combines the tranquility of country living with easy access to nearby towns, shopping, dining, and commuter routes. With plenty of room for your vision—whether that’s a custom residence, hobby farm, or private

    Alicia Gannon Dulin Benson & Mangold, LLC

    Lot 1 Dover Bridge Rd, Preston, MD 21655
  • /34

    $265,000

    • 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
  • /6

    $195,000

    • 2 Beds
    • 1 Bath
    • 700 Sq Ft

    546 N 6th St, Denton, MD 21629

    Deed reference 00616/00474, Plat reference 0027/1775 SDAT presents use as commercial Town Scale Residential has been zoning w/commercial zoning adopted 2/13/24. Leasing a possibility call listing agent for details.

    Randy Staats Benson & Mangold, LLC

    546 N 6th St, Denton, MD 21629
  • /25

    $279,000

    • 4 Beds
    • 1.5 Baths
    • 1,670 Sq Ft

    317 W Central Ave, Federalsburg, MD 21632

    Newly renovated 4 bedroom, 1.5 bath. Large back yard with large shed and mostly new fence. Still has many original features, lovely molding and stairs. New Central Heat and Air, new roof, new flooring and paint throughout; new kitchen appliances and countertop; large basement with two extra storage rooms, in great condition. Listing Agent is Owner, call with any questions. Thank you for

    Kelly Sharpless Kelstar Properties

    317 W Central Ave, Federalsburg, MD 21632
  • /21

    $434,900

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

    5 Lister Ln, Ridgely, MD 21660

    Price Reduced! Lister Estates = Excellent Location!! Lovely 5 Bedroom 2.5 Bath Home in very sought after Lister Estates. Roof 2 years old and HVAC system only 5 years old. High ceilings and partially open main floor plan with a warm and sunny bump-out breakfast nook, Kitchen and Family Room along with Powder room, and a separate Dinning and Sitting room area. The upper floor boasts a Huge

    Connie Mahaney Schwartz Realty, Inc.

    5 Lister Ln, Ridgely, MD 21660
  • /3

    $104,900

    • 3 Beds
    • 2 Baths
    • 2,312 Sq Ft

    9709 Foy Rd, Denton, MD 21629

    Priced To Sell Fast! Investor Alert! Renovate & Resell, Buy and Hold or Tear Down and Develop. Major Rehab Needed, City Will Require Permits. Per the City Lot Can be Split into 3 Parcels. 1.72 Acres Total. 3 Level Colonial, Spacious Kitchen, Spacious Bedrooms, Hardwood Floors, Much More!! Just Waiting For Your Personal Cosmetics and Renovations to Make it Shine. Close to Schools, Shopping and

    Matthew Altizer ANR Realty, LLC

    9709 Foy Rd, Denton, MD 21629
  • /49

    $415,000

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

    8556 Tuckahoe Rd, Denton, MD 21629

    Attractive Price Reduction -Incredible Value with InGround Pool Welcome to 8556 Tuckahoe Rd -Come take a peek at your new home—you’ll be glad you did next summer while swimming in your inground pool, grilling out, and gathering around the firepit with family and friends.A private retreat on over an acre just minutes from Tuckahoe State Park! Step outside to your own backyard oasis

    Kathleen Armiger Coldwell Banker Realty

    8556 Tuckahoe Rd, Denton, MD 21629
  • /13

    $240,000

    • 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

    $285,000

    • 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
  • /21

    $269,000

    • 3 Beds
    • 1 Bath
    • 1,019 Sq Ft

    529 N 6th St, Denton, MD 21629

    Welcome to this beautifully maintained 3 bedroom, 1 bath home that blends classic character with modern updates. Inside, you’ll find original hardwood floors that add warmth and charm throughout the living space.Enjoy a spacious backyard perfect for entertaining or relaxing, plus a brand new oversized back deck completed in 2025, ideal for outdoor gatherings. The home also features new

    Cody Weese Weese Properties, LLC

    529 N 6th St, Denton, MD 21629
  • /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
  • /60

    $724,900

    • 3 Beds
    • 2 Baths
    • 1,834 Sq Ft

    28402 Liden School Rd, Denton, MD 21629

    This home is on one acre with an additional 15.77 acres - possibly one additional acre in deed. This home says "home from the time you drive up the drive and into this gorgeous rancher with comfort written all over." The kitchen has all stainless steel appliances and a large pantry. Large Island with cabinetry as well as seating for meals or snacks or just relaxing in the kitchen. The pellet

    Bonnie Duley Long & Foster Real Estate, Inc.

    28402 Liden School Rd, Denton, MD 21629
  • /20

    $199,900

    • 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
  • /44

    $225,000

    • 4 Beds
    • 2 Baths
    • 2,884 Sq Ft

    148 Main St, Preston, MD 21655

    Welcome to this timeless 1880 Federal style House, where historic charm meets thoughtful modern updates. Situated on a serene and spacious lot dotted with beautiful mature fruit trees, this 4 bedroom, 2 bath home offers approximately 2800 sq ft of character-filled space. Many renovations have already been completed- preserving original architectural details while adding essential modern

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    148 Main St, Preston, MD 21655
  • /10

    $275,000

    • 3 Beds
    • 2 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

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    21245 Tanyard Rd, Preston, MD 21655
  • /30

    $269,000

    • 3 Beds
    • 1.5 Baths
    • 1,092 Sq Ft

    312 Fountain Ave, Denton, MD 21629

    Charming in-town living in this Beautifully Remodeled 3-Bedroom Rancher! Updates include Fresh Paint, NEW Luxury Vinyl Plank Flooring, NEW Kitchen Cabinets, NEW Tile Backsplash and NEW Quartz Countertops! Ceiling Fans in all Bedrooms, Living Room and Dining area to ensure comfort throughout. Turn-Key and ready for you to move right in! Situated on a large Corner Lot with a Spacious Driveway

    Pamela Ackermann-Doll RE/MAX Executive

    312 Fountain Ave, Denton, MD 21629
  • /25

    $289,000

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

    1904 Blue Heron Dr, Denton, MD 21629

    Welcome to Mallard Landing and your own private townhouse in the quiet, peaceful outskirts of Denton. This charming 2,640 sq ft townhouse offers thoughtfully designed living space, including four spacious bedrooms, four bathrooms, a bar-counter dine-in kitchen, and a formal dining room. As you step inside the front door, you’ll notice three levels of spacious room sizes, a walk-in closet in the

    Ralph Harvey ListWithFreedom.com

    1904 Blue Heron Dr, Denton, MD 21629
  • /46

    $429,900

    • 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
  • /20

    $199,900

    • 2 Beds
    • 1.5 Baths
    • 1,196 Sq Ft

    341 Academy Ave, Denton, MD 21629

    Welcome to Denton! Small town living with all the amenities nearby! Cute townhouse with two bedrooms, one and a half baths with washer/dryer in unit. Low maintenance and No HOA. Walk into town for coffee or a meal then walk down to the water along the Choptank River. Boat ramp and kayak/paddle board launch minutes away. Super Walmart and other shopping just minutes away. Don't miss this

    Jason Dey Kevin Dey Realty

    341 Academy Ave, Denton, MD 21629
  • /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
  • /40

    $475,000

    • 3 Beds
    • 2 Baths
    • 1,952 Sq Ft

    8452 Harmony Rd, Denton, MD 21629

    Huge price improvement! Your Own Slice of Paradise!Pride of ownership shines throughout this beautifully updated rancher, perfectly nestled on 4 acres of serene countryside complete with a pond stocked with koi, catfish and goldfish—a dream setting for nature lovers and outdoor enthusiasts alike. Step inside and fall in love with the modern touches and thoughtful upgrades throughout.

    Tracey Bellotte Coldwell Banker Realty

    8452 Harmony Rd, Denton, MD 21629
  • /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
  • /30

    $430,000

    • 4 Beds
    • 2.5 Baths
    • 3,838 Sq Ft

    1111 Daylily Ln, Denton, MD 21629

    Welcome to your dream home at 1111 Daylily Ln, nestled in the desirable community of Cattail Commons. This spacious 4-bedroom, 2.5-bath home offers the perfect blend of functionality and style, thoughtfully designed for everyday living and effortless entertaining.The bright and airy main level features an open-concept kitchen and dining area, ideal for hosting gatherings, along with a

    Joni Barrow Keller Williams Realty

    1111 Daylily Ln, Denton, MD 21629
  • /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
  • /89

    $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
  • /50

    $432,000

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

    26674 Bentley Place, Henderson, MD 21640

    Price reduction of $10,000! This beauty was built in 2004, current owners moved in 2006 added the in-ground salt water pool and property sits on 1.30 acres!! This large 4 bedroom and 2.5 bath home is just the perfect size. Beautiful hard wood floors throughout the first floor, with an open floor plan. Fireplace on first floor runs on propane, which seller does not use or have a propane

    Sally Fricke RE/MAX Solutions

    26674 Bentley Place, Henderson, MD 21640
  • /50

    $310,000

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

    8409 Harmony Rd, Denton, MD 21629

    A Rare Blend of Modern Comfort & Serene Country Living! 8409 Harmony Road – A True Hidden Gem on 1.14 Acres!Step into the perfect balance of modern upgrades and rustic charm with this beautifully renovated, move-in-ready 3-bedroom, 2-bathroom home nestled on a peaceful 1.14-acre lot with dual road access from Towers Road and Harmony Road.Inside, you'll be welcomed by a bright, airy open

    Sandra Gendleman Long & Foster Real Estate, Inc.

    8409 Harmony Rd, Denton, MD 21629

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