125

Caroline County MD Homes for Sale

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  • /39

    $219,999

    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft

    107 Smith St, Federalsburg, MD 21632

    A must see, updated + upgraded, 1-level, 3-bedroom,1.5-bath home with an open floorplan. Situated on a nice-sized yard, this welcoming home offers more than meets the eye. Handsome + durable luxury vinyl plank flooring, fresh paint, and updated fixtures throughout. Spacious living room with a bar and radiant countertops overlook the kitchen. Dining room with breakfast bar and sliding glass door.

    Brandon Brittingham EXP Realty, LLC

    107 Smith St, Federalsburg, MD 21632
  • /12

    $125,000

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    103 Chamber St, Preston, MD 21655

    This Colonial home features timeless architecture and thoughtful design. The property offers solid construction and classic appeal, making it an excellent opportunity for discerning buyers. This distinctive property presents an outstanding opportunity for transformation and value creation. The established neighborhood setting combines small-town charm with practical accessibility to essential

    Pamela Geib Long & Foster Real Estate, Inc.

    103 Chamber St, Preston, MD 21655
  • /35

    $249,900

    • 4 Beds
    • 0.5 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
  • /14

    $140,000

    • 2 Beds
    • 2 Baths
    • 640 Sq Ft

    26471 Three Bridges Rd, Federalsburg, MD 21632

    Opportunity awaits at 26471 Three Bridges Rd in Federalsburg, MD! This partially remodeled 2-bedroom, 2-bath home is ready for your finishing touch. Inside, the property has been taken down to the framing and subflooring, giving you a true blank canvas to bring your vision to life—whether you’re an investor looking for your next project or a buyer ready to customize every detail. Set on nearly a

    LEE MARLAND Keller Williams Realty

    26471 Three Bridges Rd, Federalsburg, MD 21632
  • /3

    $99,000

    • 2 Beds
    • 1 Bath
    • 956 Sq Ft

    804 Gay St, Denton, MD 21629

    Property is being sold in as/ is condition.

    Diane Wenk Wright Real Estate

    804 Gay St, Denton, MD 21629
  • /22

    $510,000

    • Land
    • 63.16 Acres
    • $8,075 per Acre

    0 Dover Bridge Rd Unit MDCM2005586, Preston, MD 21655

    Dover Bridge Road | Preston, MarylandThis 63 ± acre parcel on Dover Bridge Road offers a rare opportunity to own a sizeable tract of woodland conveniently located just four miles from Preston, seven and a half miles from Easton, and about fifteen minutes from Route 50.The property is perc-approved for residential use and includes a forestry management plan documenting that roughly 58

    Coard Benson Benson & Mangold, LLC

    0 Dover Bridge Rd Unit MDCM2005586, Preston, MD 21655
  • /3

    $265,000 Coming Soon

    • 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. Coming Soon

    Barbara Beaudet Brenton Realty Group

    10819 Greensboro Rd, Denton, MD 21629
  • /7

    $127,000

    • Land
    • 4.14 Acres
    • $30,676 per Acre

    0 Burnt Mill Rd Unit MDCM2006400, Ridgely, MD 21660

    Discover the ideal blend of tranquil nature and prime location! 4.14 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

    Stephan Strothe Washington Fine Properties, LLC

    0 Burnt Mill Rd Unit MDCM2006400, Ridgely, MD 21660
  • /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
  • /6

    $85,000

    • Land
    • 1.15 Acres
    • $73,913 per Acre

    0 Laurel Ln, Denton, MD 21629

    Beautiful, wooded lot ready to be built on available in established Forest Landing. Conveniently located between Denton and Easton. Lot has approved perc for a 4 bedroom mound system. Community offers a private beach area, picnic tables, great spot to launch your canoe or kayak or do a little fishing. Not many opportunities to build your next home in a mature neighborhood left around.

    Michael Bozek Michael J. Bozek

    0 Laurel Ln, Denton, MD 21629
  • /17

    $230,000

    • 3 Beds
    • 2 Baths
    • 1,448 Sq Ft

    113 Maple Ave, Goldsboro, MD 21636

    Welcome to the pleasures of small town living in this updated Farmhouse. This 3 bed 2 bath home sits on a .23 acre lot with most of the land in the backyard for relaxing and entertaining. Plenty of room for gardens or playground area. Outbuilding for extra storage. Enjoy the evenings on the back deck overlooking the yard or enjoy the front porch with coffee and listen to the rain. Contract will

    Roger Boyce Chesapeake Real Estate Associates, LLC

    113 Maple Ave, Goldsboro, MD 21636
  • /24

    $286,990 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
  • /16

    $250,000

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

    115 Maple Ave, Goldsboro, MD 21636

    Step into a rare opportunity to own a beautifully updated Victorian-style home located on a quiet, established street in the heart of Goldsboro. Perfectly situated on a generous 0.55-acre lot, this home offers over 2,000 square feet of flexible living space while preserving the character buyers love. Inside, the freshly painted interior and brand new laminate flooring create a bright and

    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
  • /41

    $269,900

    • 4 Beds
    • 1.5 Baths
    • 2,820 Sq Ft

    306 S Main St, Federalsburg, MD 21632

    Bring Your Fishing Pole! Nestled along the tranquil waters of Marshyhope Creek, this waterfront retreat offers peaceful views and the rare opportunity to fish or kayak directly from your own private shoreline. This charming 2,820 sq. ft. Victorian home features 4 spacious, freshly painted bedrooms and 1.5 baths and is ready for you to add your special touches. Begin your mornings with coffee on

    Mary Mabry Keller Williams Select Realtors of Cambridge

    306 S Main St, Federalsburg, MD 21632
  • /43

    $245,000

    • 3 Beds
    • 1 Bath
    • 1,385 Sq Ft

    511 Bernard Ave, Greensboro, MD 21639

    Spacious rancher located on a double lot, over one-third of an acre, plenty of room for outdoor activities or potential future expansion. This home features solid construction and has had significant updates in the past 3-4 years, including a new roof, new windows, and a new HVAC system, adding considerable value and reduces the worry about major repairs in the near future. Inside the residence

    Karen Clark Clark & Co Realty, LLC

    511 Bernard Ave, Greensboro, MD 21639
  • /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
  • /2

    $79,000

    • Land
    • 2.11 Acres
    • $37,441 per Acre

    lot 6 Harmony Woods Dr, Preston, MD 21655

    Barbara Nichols Results Realty Inc.

    lot 6 Harmony Woods Dr, Preston, MD 21655
  • /4

    $92,000

    • Land
    • 0.33 Acre
    • $278,788 per Acre

    162 Main St, Preston, MD 21655

    Anne Schmidt Long & Foster Real Estate, Inc.

    162 Main St, Preston, MD 21655
  • /20

    $290,000 Open Sat 11AM - 1PM

    • 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 yard, perfect for outdoor activities. Inside, the home boasts 1,426 sq. ft.

    Tricia Wilson Wilson Realty & Staging LLC

    1303 Fairfield Ct, Denton, MD 21629
  • /64

    $425,000

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

    8578 Tuckahoe Rd, Denton, MD 21629

    This property boasts with a 4 bedroom 3 full bathroom cape cod on a 1 acre lot in a beautiful wide open country setting! Fresh paint throughout the entire house, new refrigerator, new oven, new dryer AND new HVAC! All of the hard work has been done! Minutes to Denton or Easton. Move in ready! There is still plenty of time to be in a new home for the holidays!

    Megan Rosendale Rosendale Realty

    8578 Tuckahoe Rd, Denton, MD 21629
  • /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
  • /32

    $450,000

    • 1 Bed
    • 1.5 Baths
    • 1,596 Sq Ft

    23629 Willow Pond Rd, Denton, MD 21629

    A Distinctive Live/Work Opportunity on Marylands Eastern Shore. This prime location tucked away between Easton & Denton, is this remarkable and beautifully maintained, 6.18 acre property that combines the tranquility of a pastoral countryside with the practicality of a live/work lifestyle. Set on 6.18 acres of gently rolling land, this is One Lot, divided into 2 parcels, (one 2 .18 Acre and one 4

    Stephany Barrett Long & Foster Real Estate, Inc.

    23629 Willow Pond Rd, Denton, MD 21629
  • /6

    $159,900

    • Land
    • 5.28 Acres
    • $30,284 per Acre

    0 5 281 Acres Schulyer Rd, Goldsboro, MD 21636

    Peaceful 5.281-Acre Wooded Homesite with Wildlife Pond Views. Discover the perfect blend of natural beauty and rural tranquility on this 5.281-acre perc-approved building lot, ready for your dream home. Nestled in a quiet country setting, this property offers a stunning overlook of a preserved wildlife pond, where geese, ducks, deer, and turkeys are frequent visitors—creating your own private

    Brett Schrader Taylor Properties

    0 5 281 Acres Schulyer Rd, Goldsboro, MD 21636
  • /3

    $25,000

    • 728 Sq Ft

    23547 Jonestown Ln, Preston, MD 21655

    Build your dream home on this available lot in Preston, Md. Old home on property - either tear down or restore. Buyer to complete due diligence with County

    Dalton Adshead Keller Williams Select Realtors of Cambridge

    23547 Jonestown Ln, Preston, MD 21655
  • /22

    $266,990 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
  • /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
  • /2

    $94,500

    • 3 Beds
    • 2 Baths
    • 2,116 Sq Ft

    103 S Main St, Federalsburg, MD 21632

    Federalsburg - can be used as office on first floor and apartment on second floor ; or as single family.

    Valerie Brown Coldwell Banker Realty

    103 S Main St, Federalsburg, MD 21632
  • /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
  • /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
  • /35

    $289,900

    • 3 Beds
    • 2 Baths
    • 1,787 Sq Ft

    3675 Seaman Rd, Preston, MD 21655

    Charming Eastern Shore property set on a peaceful stretch of Seaman’s Road in Preston, MD. Enjoy the tranquility of country living with convenient access to nearby towns, outdoor recreation, and local amenities. A great opportunity for those seeking space, privacy, and small-town charm.

    Brian Jones Keller Williams Select Realtors of Annapolis

    3675 Seaman Rd, Preston, MD 21655
  • /40

    $460,000

    • 3 Beds
    • 2.5 Baths
    • 1,816 Sq Ft

    320 N Main St, Greensboro, MD 21639

    Welcome to 320 N Main St in the quaint town of Greensboro, where you'll find a home that invites you to kick off your shoes and stay a while. This residence sits on a half-acre lot and features three bedrooms and 2.5 baths, offering an ideal balance of space, comfort, and style. The beautifully updated kitchen is ready for all your culinary adventures, boasting a five-burner gas range, stainless

    Karen Clark Clark & Co Realty, LLC

    320 N Main St, Greensboro, MD 21639
  • /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
  • /12

    $60,000

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

    21269 Dover Bridge Rd, Preston, MD 21655

    Nestled in Dover Bridge Mobile Home Park—formerly Prettyman Manor—this double-wide manufactured home sits on one of the largest lots in this peaceful community. The property offers plenty of space and potential, with a few upcoming improvements to help set the stage for its next owner. While it could use a bit of attention, it’s a wonderful opportunity to make this home your own in a quiet,

    Donna Harrington Coldwell Banker Realty

    21269 Dover Bridge Rd, Preston, MD 21655
  • /2

    $30,000

    • Land
    • 0.54 Acre
    • $55,556 per Acre

    26519 3 Bridges Rd, Federalsburg, MD 21632

    Previous building is a complete tear down. Do not enter the building. Half acre lot zoned R1, one property. Buyer must contact Caroline County for any more information. There could be a private community septic on the property. Seller will consider holding a 2 year note with $15,000 down payment.

    Charles Hajjar Smart Realty, LLC

    26519 3 Bridges Rd, Federalsburg, MD 21632
  • /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
  • /127

    $2,999,000

    • 8 Beds
    • 16 Baths
    • 9,364 Sq Ft

    4218 Harmony Rd, Preston, MD 21655

    A truly rare offering for the discerning auto enthusiast, this exceptional 58.48-acre Eastern Shore estate is a masterfully designed luxury compound where architectural elegance meets world-class automotive accommodations. Introduced by a private gated entrance and tree-lined circular drive, the stately brick home immediately conveys the scale, privacy, and prestige of this one-of-a-kind

    Donna Harrington Coldwell Banker Realty

    4218 Harmony Rd, Preston, MD 21655
  • /91

    $699,000

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

    4 S 1st St, Denton, MD 21629

    Outstanding Business Opportunity! Rare Find with-in Downtown Denton! Property would make an excellent Restaurant, Bar, great Venue , or a Large Victorian Home! 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! Town ERU's are

    Kathleen Brenton Brenton Realty Group

    4 S 1st St, Denton, MD 21629
  • /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
  • /25

    $124,900

    • 2,168 Sq Ft

    28035 Possum Hill Rd, Federalsburg, MD 21632

    Prime Half-Acre Lot Near Smithville Lake – Cleared, with Well and Oversized Garage BayThis unique 0.48-acre property on Possum Hill Rd is ideally situated less than a mile west of the Maryland-Delaware state line, offering a rare combination of open space, infrastructure, and development potential.Property Highlights:Cleared Lot with Existing Well – The land has already been cleared

    Sam Benkirane Proplocate Realty, LLC

    28035 Possum Hill Rd, Federalsburg, MD 21632

Showing Results 41 - 80, Page 2 of 4

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