158

Caroline County MD Homes for Sale

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  • /74

    $525,000

    • 3 Beds
    • 3 Baths
    • 3,088 Sq Ft

    22005 Main St, Hillsboro, MD 21641

    PLEASE NOTE that the Owner has listened to the current market, Price has been reduced to $525,000. It is a property of beautifully preserved quality on 3⁄4 of an acre in an urban setting. Most unusual! When compared to equivalent historic properties it is now very competitively priced! This fine, brick dwelling originating from the18th c. is situated in Hillsboro on Maryland's peaceful Eastern

    Nancy McGuire Maryland Heritage Properties

    22005 Main St, Hillsboro, MD 21641
  • /9

    $79,000

    • Land
    • 3.05 Acres
    • $25,902 per Acre

    10440 Burrsville Branch Rd, Denton, MD 21629

    Rare opportunity to own over 3 acres in a peaceful rural setting just outside of Denton and approximately one mile from the Maryland/Delaware state line. Close to Delaware Beaches and Tax Free Shopping. This partially wooded homesite backs to open farmland, offering privacy and picturesque country views. The property provides an ideal setting for a custom home, subject to the installation of a

    Deborah Callahan Benson & Mangold, LLC

    10440 Burrsville Branch Rd, Denton, MD 21629
  • /2

    $239,000

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 1,248 Sq Ft

    27311 Patricia Ct, Federalsburg, MD 21632

    Nestled on 3.26 private wooded acres, this charming 3 bedroom, 2.5 bath home offers the perfect blend of comfort and privacy. Enjoy peaceful views from the rear deck, a full walkout basement with endless potential, a Rinnai tankless water heater, and a Generac whole house generator for added peace of mind. Professional Photos Coming Soon A wonderful opportunity to enjoy country living with modern

    Amy Betts Coldwell Banker Realty

    27311 Patricia Ct, Federalsburg, MD 21632
  • /2

    $25,000

    • Land
    • 12,196 Sq Ft
    • $89,286 per Acre

    12087 Wayman St, Ridgely, MD 21660

    Double lot . There are the remains of a house on the property; please leave the remains "as is". Well and septic unknown.

    Bev Langley Coldwell Banker Realty

    12087 Wayman St, Ridgely, MD 21660
  • /42

    $344,900

    $14K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 1,800 Sq Ft

    222 S 2nd St, Denton, MD 21629

    This is 222 S. 2nd Street, a recently renovated home with historic charm. Original wood flooring, and architectural details such as moldings and antique door knobs highlight the home's history. Though it embraces the past, the house has been updated with all new appliances, new quartz kitchen countertops, newly painted walls and new siding. The house offers something that many two-story homes do

    Kathleen Brenton Brenton Realty Group

    222 S 2nd St, Denton, MD 21629
  • /30

    $299,900

    $20K PRICE DROP
    • 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
  • /20

    $225,000

    • 4 Beds
    • 1 Bath
    • 1,350 Sq Ft

    5258 Preston Rd, Federalsburg, MD 21632

    4 bedrooms 1 bathroom bungalow being sold "AS IS". 16,700 sq. ft. lot with detached garage. Priced to Sell.Updated 200. amp electric service.

    Barton Johnson/not int Marshy Hope Realty LLC

    5258 Preston Rd, Federalsburg, MD 21632
  • /43

    $364,000

    $11K PRICE DROP
    • 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 the cozy light filled living-dining area, the versatile bonus room/office and the entertainment-ready basement with a unique custom bar.

    Karen Clark Clark & Co Realty, LLC

    412 N Main St, Greensboro, MD 21639
  • /2

    $215,000

    • 3 Beds
    • 1 Bath
    • 756 Sq Ft

    105 Lincoln St, Greensboro, MD 21639

    Tenant-occupied property offering an excellent investment opportunity with immediate rental income. Current lease in place through July 31st. Tenants have expressed interest in renewing and would prefer to stay, providing potential for continued occupancy. Property is well-maintained and conveniently located near local amenities, schools, and major routes.Please allow adequate notice for all

    emily conley Taylor Properties

    105 Lincoln St, Greensboro, MD 21639
  • /67

    $426,000

    • 4 Beds
    • 3.5 Baths
    • 3,372 Sq Ft

    109 Briarwood Cir, Denton, MD 21629

    Welcome to 109 Briarwood Cir in the sought-after Sandy Meadows community of Denton, offering an impressive blend of space, comfort, and flexibility with over 3,300 finished square feet plus an additional 1,525 sq ft unfinished walkout basement ready for your future vision. With its stately two-story presence, beautiful architectural windows, mature landscaping, and inviting curb appeal, this home

    Anissa Hastings Keller Williams Flagship

    109 Briarwood Cir, Denton, MD 21629
  • /18

    $4,250,000

    • 3 Beds
    • 2.5 Baths

    10870 River Rd, Denton, MD 21629

    Productive Caroline County grain farm approximately 340 acres in 4 parcels with 270+/- tillable acres with 200+/- under pivot. Soil has been grid sampled and is well drained. Farm is improved with three large machine sheds, the potentially usable footprint of a pervious milking parlor and a 3 bedroom, 2.5 bath Rancher overlooking the Choptank River. No easements.

    Jim Corson Benson & Mangold, LLC

    10870 River Rd, Denton, MD 21629
  • /30

    $299,900

    $9K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,640 Sq Ft

    1907 Blue Heron Dr, Denton, MD 21629

    Largest townhome in the area and the best deal! Almost 2700 square feet for only $117 a square foot! The biggest bang for your buck in the county! 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

    Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    1907 Blue Heron Dr, Denton, MD 21629
  • /34

    $349,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,575 Sq Ft

    215 Apple Ln, Preston, MD 21655

    Welcome to this beautiful 3-bedroom, 2-bathroom home filled with wonderful updates throughout. As you arrive, you’ll immediately notice the brand-new roof, offering peace of mind for years to come. Step inside to discover a stunning updated kitchen featuring quartz countertops and stainless steel appliances, perfect for both everyday living and entertaining. With spring just around the corner,

    Amy Endzel Keller Williams Select Realtors of Annapolis

    215 Apple Ln, Preston, MD 21655
  • /10

    $42,999

    • Land
    • 10,454 Sq Ft
    • $179,162 per Acre

    0 Brooklyn Ave, Federalsburg, MD 21632

    Taylor McCartney VRA Realty

    0 Brooklyn Ave, Federalsburg, MD 21632
  • /11

    $249,999

    $20K PRICE DROP
    • Land
    • 14.71 Acres
    • $16,995 per Acre

    0 Trunk Rd Unit MDCM2007270, Henderson, MD 21640

    14.71± acre perc-approved parcel on Trunk Line Rd in Henderson, MD! This beautiful wooded lot offers a conventional perc approved for 4+ bedrooms and provides an excellent opportunity to build your dream home, private retreat, or future homestead. Property features approximately 466 feet of road frontage along Trunk Line Road and includes a designated sewage reserve area shown on recorded plat.

    Heather Branham The Parker Group

    0 Trunk Rd Unit MDCM2007270, Henderson, MD 21640
  • /2

    $307,490

    New Construction
    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft

    111 Hobbs St, Greensboro, MD 21639

    Explore 111 Hobbs Street, a new home under construction in the quaint Kinnamon Meadows community of Greensboro, MD. 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

    D.R. Horton Builder
    111 Hobbs St, Greensboro, MD 21639
  • /2

    $299,990

    New Construction $2K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft

    121 Hobbs St, Greensboro, MD 21639

    Come discover 121 Hobbs Street, a new home under construction in the quaint Kinnamon Meadows community of Greensboro, MD. 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.

    D.R. Horton Builder
    121 Hobbs St, Greensboro, MD 21639
  • /9

    $159,000

    • 3 Beds
    • 2 Baths
    • 2,776 Sq Ft

    106 S 6th St, Denton, MD 21629

    Charming colonial in the heart of Denton, thoughtfully converted into a two-unit multifamily property. Nestled on a quiet street, this home offers flexible living options with spacious layouts, classic character, and excellent potential for rental income or multigenerational living. A wonderful opportunity to invest or reside in a peaceful in-town setting. Great investment property.

    Amy Betts Coldwell Banker Realty

    106 S 6th St, Denton, MD 21629
  • /16

    $235,000

    $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,693 Sq Ft

    1204 Blue Heron Dr, Denton, MD 21629

    ***NEWLY ADJUSTED PRICE***Come on in to explore this beautifully maintained 3-level home offering the perfect blend of modern convenience 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 updated with fresh paint, new appliances and more to ensure it's move-in

    Carolyn A. Page Shore Results Realty

    1204 Blue Heron Dr, Denton, MD 21629
  • /12

    $299,900

    • 3 Beds
    • 1 Bath
    • 1,024 Sq Ft

    5 7th St, Ridgely, MD 21660

    Don't wait to tour this wonderfully renovated home in the Greenridge community! Lots to love from top to bottom. Completely rehabbed with Hickory Vinyl Plank flooring throughout and all freshly painted. New stainless steel appliances in the spacious kitchen with center island and lots of cabinet and working space plus a full pantry. All new beautiful bathroom with rain shower head. A laundry room

    Marcia Rostien Long & Foster Real Estate, Inc.

    5 7th St, Ridgely, MD 21660
  • /39

    $399,900

    $20K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 3,159 Sq Ft

    25331 Adams Landing Rd, Denton, MD 21629

    2 Acre cleared lot. Great opportunity for a fixer upper. Home needs a fair amount of work but it has a great layout. Main level primary, office/den separate dining room. Additional main level bedroom and full bath on main level. Spacious living room with access to the large screened porch. Corner eat-in kitchen & main level laundry. Cash or 203(K).***The property is being sold in its current

    Lisa Whited Keller Williams Realty

    25331 Adams Landing Rd, Denton, MD 21629
  • /23

    $304,990

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,219 Sq Ft

    109 Hobbs St, Greensboro, MD 21639

    Welcome to 109 Hobbs Street where a new home can be yours in Kinnamon Meadows in Greensboro, MD. This home is not currently under construction. 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

    D.R. Horton Builder
    109 Hobbs St, Greensboro, MD 21639
  • /41

    $385,000

    $4K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,138 Sq Ft

    1111 Trice Meadows Cir, Denton, MD 21629

    ****PRICE ADJUSTMENT****Discover your dream home in the highly sought-after Trice Meadows community! This delightful 4-bedroom, 2-bathroom detached single-family home perfectly combines comfort, style, and modern convenience. Its open and inviting floor plan is designed for both day-to-day living and entertaining, making it an ideal choice for families and social gatherings alike. Experience

    LaTanya Drayton United Real Estate Premier

    1111 Trice Meadows Cir, Denton, MD 21629
  • /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
  • /36

    $430,000

    $15K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,492 Sq Ft

    1709 Cattail Commons Way, Denton, MD 21629

    Welcome to 1709 Cattail Commons Way, located in the highly desirable Savannah Overlook community in Denton, MD. This beautifully maintained 4-bedroom, 2.5-bath home offers a spacious open floor plan, modern upgrades, and move-in ready convenience—perfect for today’s buyer seeking comfort, functionality, and style. The main level features a bright and open layout ideal for both everyday living and

    Kaitlyn Collins Benson & Mangold, LLC

    1709 Cattail Commons Way, Denton, MD 21629
  • /14

    $95,000

    • 1 Bed
    • 1 Bath
    • 692 Sq Ft

    316 Liberty Rd, Federalsburg, MD 21632

    Nestled in the charming TOWN OF FEDERALSBURG, this exquisite bungalow, built in 1930, seamlessly blends timeless elegance with modern comforts. This delightful residence invites you to experience a lifestyle of warmth and sophistication, perfect for those seeking a serene retreat. As you approach the property, the classic vinyl siding and inviting front entry beckon you inside. Step into a cozy

    Barton Johnson/not int Marshy Hope Realty LLC

    316 Liberty Rd, Federalsburg, MD 21632
  • /2

    $175,000

    • Land
    • 18.51 Acres
    • $9,454 per Acre

    0 Houston Branch Rd Unit MDCM2006924, Federalsburg, MD 21632

    These parcels are being sold as part of an estate. Three contiguous parcels with a total of 18.51 acres. Parcel 2 received Preliminary Perc Approval April 2015.

    Andrew Beaven Wright Real Estate

    0 Houston Branch Rd Unit MDCM2006924, Federalsburg, MD 21632
  • /27

    $225,000

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,311 Sq Ft

    25910 Fox Grape Rd, Greensboro, MD 21639

    Quiet living in Fox Grape Farms. Whether you are downsizing or just starting out, this home offers one-level living with 3 bedrooms, 2 full baths and an open living room that flows into the dining area. Situated on a 0.60 +/- parcel, the property also features two (2) storage sheds. Located approximately 7 miles from Denton, MD, 11 miles from Tuckahoe State Park and 16 miles from the Harrington

    John Fifer Brokers Realty Group, LLC

    25910 Fox Grape Rd, Greensboro, MD 21639
  • /2

    $355,000

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

    306 Caroline Ave, Ridgely, MD 21660

    Charming updated Farmhouse style home with hardwood floors throughout and tiled bathrooms. The open kitchen features quartz countertops, a center island for extra prep space and casual dining, stainless steel appliances, and a tile backsplash. The first floor includes a full bath with a tiled walk-in stall shower, plus a separate laundry/mud room. Dual-zone heating and air for year-round comfort.

    Roger Boyce Chesapeake Real Estate Associates, LLC

    306 Caroline Ave, Ridgely, MD 21660
  • /8

    $85,000

    • Land
    • 32,234 Sq Ft
    • $114,865 per Acre

    0 Mill & Lincoln St, Greensboro, MD 21639

    3 Parcels in the Town of Greensboro!! One of which has a hooked up Water/Sewer account, so instant savings on no tap fee!! Parcels are believed to total approximately 0.74 Acres, more or less. Abandoned dwelling exists in the center of the parcels, in need of tear down or possible major renovation. Town of Greensboro building codes and ordinances are online their website. NOTE: The parcel numbers

    Erin Anderson Chesapeake Real Estate Associates, LLC

    0 Mill & Lincoln St, Greensboro, MD 21639
  • /16

    $415,000

    New Construction
    • 4 Beds
    • 2 Baths
    • 1,628 Sq Ft

    5 Sunrise Ave, Ridgely, MD 21660

    Colors, materials, and finishes are subject to change New Construction Home built by the reputable Lomaxx Custom Homes! The final home in Sunrise Village, this is your opportunity to get in early and make your personal selections. This one story home will offer 4 bedrooms, 2 full bathrooms and an open concept layout with stylish and on trend finishes throughout. Home to be completed July 2026

    Amy Betts Coldwell Banker Realty

    5 Sunrise Ave, Ridgely, MD 21660
  • /28

    $229,900

    $20K PRICE DROP
    • 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
  • /48

    $299,000

    $56K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 708 Sq Ft

    13306 Greensboro Rd, Greensboro, MD 21639

    Stunning waterfront renovation on the Choptank River—completely redone inside and out in 2025! This beautifully updated 2-bedroom, 1.5-bath home offers approximately 800± square feet of thoughtfully designed living space. Completely remodeled from top to bottom, the residence showcases modern design and high-end finishes throughout. Updates include all-new walls, bathrooms, appliances, kitchen

    Lisa Magnus Clark & Co Realty, LLC

    13306 Greensboro Rd, Greensboro, MD 21639
  • /6

    $49,900

    • Land
    • 2.55 Acres
    • $19,569 per Acre

    0 Havercamp Rd, 4, Preston, MD 21655

    If you’ve been searching for a private, wooded homesite without feeling too far removed from everyday conveniences, this is it. Offering over 2.5 acres, this property provides the perfect blend of seclusion and accessibility—ideal for building your dream home exactly the way you envision it. Located on Havercamp Rd, you’ll enjoy a peaceful, tucked-away setting while still being just minutes from

    Aubrey Campbell Keller Williams Realty Delmarva

    0 Havercamp Rd, 4, Preston, MD 21655
  • /53

    $525,000

    • 2 Beds
    • 1 Bath
    • 1,292 Sq Ft

    5820 Bell Creek Rd, Preston, MD 21655

    Don’t miss this exceptional 20+/- acre working horse farm thoughtfully designed for both functionality and country living. This well-equipped equestrian property offers everything needed for training, boarding, riding, and daily farm operations. The property features a 36’ x 40’ center-aisle barn with 9 stalls, water, electric, and an insulated tack room, along with a 77’ x 36’ metal barn

    Colleen Smith EXP Realty, LLC

    5820 Bell Creek Rd, Preston, MD 21655
  • /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
  • /33

    $345,000

    • 4 Beds
    • 2 Baths
    • 2,172 Sq Ft

    612 Market St, Denton, MD 21629

    Step back in time while enjoying the comforts of modern living in this beautifully maintained 1900s historic home nestled in the heart of Denton. Rich with character and timeless charm, this spacious four-bedroom, two-bath residence showcases many of the architectural details that make historic homes so special, including original hardwood floors, detailed moldings, tall ceilings, oversized

    Joelle Dolch Cross Street Realtors LLC

    612 Market St, Denton, MD 21629
  • /2

    $55,000

    • Land
    • 4.17 Acres
    • $13,189 per Acre

    E/S MD RT480 Unknown, Hillsboro, MD 21641

    Seller is waiting for perk results from Caroline county health department

    Diane Wenk Wright Real Estate

    E/S MD RT480 Unknown, Hillsboro, MD 21641

Showing Results 121 - 158, Page 4 of 4

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