164

Caroline County MD Homes for Sale

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  • /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
  • /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
    • 30,056 Sq Ft
    • $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
  • /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

    $23,000

    • Land
    • 6,098 Sq Ft
    • $164,286 per Acre

    12115 Lincoln St, Ridgely, MD 21660

    Vacant lot, check with the county about putting a new house on this lot. There was previously a house on this lot.

    Pamela Geib Long & Foster Real Estate, Inc.

    12115 Lincoln St, Ridgely, MD 21660
  • /2

    $30,000

    • Land
    • 23,522 Sq Ft
    • $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
  • /29

    $319,000

    $20K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 2,017 Sq Ft

    211 Bloomingdale Ave, Federalsburg, MD 21632

    Welcome to 211 Bloomingdale Ave. This custom‐built Brick Williamsburg‐style colonial showcases true craftsmanship, featuring beautiful hardwood floors throughout, custom built‐ins, and detailed moldings. The spacious living room offers an inviting wood‐burning fireplace, while the large great room with its vaulted ceiling provides flexible living space and could easily be converted into a third

    Jana Meredith Meredith Fine Properties

    211 Bloomingdale Ave, 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
  • /12

    $82,500

    $53K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    103 Chambers 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 Chambers St, Preston, MD 21655
  • /59

    $465,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,038 Sq Ft

    27329 Iron Gate Rd, Federalsburg, MD 21632

    Charming Colonial-style farmhouse set on 9 scenic acres, offering a rare blend of historic character, pastoral beauty, and endless potential. Ideal for animal lovers or those seeking a peaceful weekend retreat, the home features hardwood floors, exposed ceiling beams, and three wood-burning stoves that add warmth and timeless appeal. Large Spacious bedrooms, a screened porch and rear patio

    Shannon Parker Keller Williams Select Realtors of Cambridge

    27329 Iron Gate Rd, Federalsburg, MD 21632
  • /23

    $295,000

    • 3 Beds
    • 2 Baths
    • 1,646 Sq Ft

    130 Charlotte Ave, Federalsburg, MD 21632

    Welcome to 130 Charlotte Avenue in Federalsburg, Maryland—a well-appointed home offering three bedrooms, two full baths, and an attached two-car garage with a versatile bonus room above, ideal for a home office, gym, or guest space. Tucked away at the end of a quiet cul-de-sac, this property provides private outdoor enjoyment while remaining conveniently located for an easy commute to Seaford and

    FRANK LITTLE Berkshire Hathaway HomeServices PenFed Realty

    130 Charlotte Ave, Federalsburg, MD 21632
  • /50

    $609,000

    • 5 Beds
    • 2.5 Baths
    • 2,920 Sq Ft

    24276 Asbury Dr, Denton, MD 21629

    Nestled in the shadows of the Choptank River is a meticulously maintained home in the water-privileged neighborhood of Asbury. Beautiful Expansive lot size gives you the privacy needed within a walkable neighborhood. The flat level lot opens up future pool and other amenity possibilities. Sit in your rocker with a cocktail while enjoying the dream turned into a reality of a wrap-around porch. A

    Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    24276 Asbury Dr, Denton, MD 21629
  • /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
  • /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
  • /47

    $664,999

    • 4 Beds
    • 2.5 Baths
    • 2,576 Sq Ft

    4757 Long Swamp Rd, Federalsburg, MD 21632

    Welcome to 4757 Long Swamp Rd, a truly unique property in Federalsburg, MD, offering the perfect blend of equestrian facilities and comfortable country living on 7.04 acres. This well-maintained estate is ready for you and your horses, with no restrictions on property use and the added flexibility for the land to be subdivided. The grounds feature expansive pastures secured by electric fencing, a

    Billy Mister Keller Williams Realty

    4757 Long Swamp Rd, Federalsburg, MD 21632
  • /24

    $249,900

    • 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
  • /6

    $159,900

    $10K PRICE DROP
    • Land
    • 5.28 Acres
    • $30,284 per Acre

    0 5 281 Acres Schulyer Rd, Goldsboro, MD 21636

    Peaceful 5.281-Acre Wooded Home site with Wildlife Pond Views. Owner Financing Available with an acceptable down payment and terms. 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,

    Brett Schrader Taylor Properties

    0 5 281 Acres Schulyer Rd, Goldsboro, MD 21636
  • /28

    $399,000

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 1,768 Sq Ft

    1 Sunrise Ave, Ridgely, MD 21660

    1 Sunrise Avenue is complete and ready for your private tour today! Just imagine starting your mornings in this thoughtfully crafted Lomaxx Custom Homes new build. Golden light spills across the nearby fields and settles gently indoors, where days begin with coffee on the back deck, birds gliding by, and daylight drifting through the windows, filling each room with a calm glow. Lomaxx Custom

    Crystal Smith RE/MAX Executive

    1 Sunrise Ave, Ridgely, MD 21660
  • /14

    $120,000

    $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 640 Sq Ft

    26471 Three Bridges Rd, Federalsburg, MD 21632

    **Back Active at no fault of the seller**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

    LEE MARLAND Keller Williams Realty

    26471 Three Bridges Rd, Federalsburg, MD 21632
  • /103

    $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

    $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
  • /37

    $265,900

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

    2697 Choptank Main St, Preston, MD 21655

    Charming Renovated Home in Choptank, Preston MD. This home currently has a fresh coat of interior paint, new kitchen appliances. Luxury vinyl flooring installed in the Living Room. Updated bath vanities and many more updates. It is turn key and ready and waiting for you. Situated on a large double lot with mature landscaping. Don’t miss this beautifully completely renovated 2-bedroom, 2-bath home

    Darlene Wheatley Benson & Mangold, LLC

    2697 Choptank Main St, Preston, MD 21655
  • /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
  • /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
  • /4

    $92,000

    • Land
    • 14,374 Sq Ft
    • $278,788 per Acre

    162 Main St, Preston, MD 21655

    Anne Schmidt Long & Foster Real Estate, Inc.

    162 Main St, Preston, MD 21655
  • /9

    $89,000

    • Land
    • 3.05 Acres
    • $29,180 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 AS-IS

    Deborah Callahan Benson & Mangold, LLC

    10440 Burrsville Branch Rd, Denton, MD 21629
  • /24

    $294,990

    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
  • /22

    $269,990

    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
  • /3

    $282,990

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft

    Curtis Plan at Kinnamon Meadows, Greensboro, MD 21639

    The Curtis is a 1,182 square foot, cottage-style ranch home with three bedrooms and two bathrooms. As you enter the home through the front porch, this thoughtfully designed home has a grand open concept living area that leads into the spacious kitchen. To the right, a long, main hallway allows for the two guest bedrooms and guest bathroom to be separate from the living areas of the home. Along

    D.R. Horton Builder
    103 Park Ave Unit 36203276, Greensboro, MD 21639
  • /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
  • /4

    $24,500

    $11K PRICE DROP
    • 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
  • /14

    $124,900

    $55K PRICE DROP
    • Land
    • 10.39 Acres
    • $12,021 per Acre

    PARCEL 91 Cool Spring Rd, Marydel, MD 21649

    Ready for you to build your new home! This beautiful lot is already perc approved for a 3-bedroom home. A barnominium is permitted to be built on this property and would be wonderful on this location. 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

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    (410) 650-6268

    PARCEL 91 Cool Spring Rd, Marydel, MD 21649
  • /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
  • /8

    $125,000

    • Land
    • 2.31 Acres
    • $54,113 per Acre

    0 Burnt Mill Rd Unit MDCM2005294, Ridgely, MD 21660

    Welcome to the Oasis neighborhood, a serene and picturesque enclave nestled in the charming town of Ridgely, MD. This prestigious 2.3-acre wooded lot on Burnt Mill Road presents a unique opportunity to craft your dream home amidst nature's splendor. With its perc approval, this lot is primed and ready for you to bring your architectural vision to life. As you enter the Oasis, you're greeted by a

    Agent Photo

    Gretchen Wichlinski

    Compass

    (667) 282-1883

    0 Burnt Mill Rd Unit MDCM2005294, Ridgely, MD 21660
  • /9

    $125,000

    • Land
    • 2.54 Acres
    • $49,213 per Acre

    0 Burnt Mill Rd Unit MDCM2005298, Ridgely, MD 21660

    Welcome to the Oasis neighborhood, a serene and picturesque enclave nestled in the charming town of Ridgely, MD. This prestigious 2.5-acre wooded lot on Burnt Mill Road presents a unique opportunity to craft your dream home amidst nature's splendor. With its perc approval, this lot is primed and ready for you to bring your architectural vision to life. As you enter the Oasis, you're greeted by a

    Agent Photo

    Gretchen Wichlinski

    Compass

    (667) 297-6243

    0 Burnt Mill Rd Unit MDCM2005298, Ridgely, MD 21660
  • /8

    $125,000

    • Land
    • 2.4 Acres
    • $52,083 per Acre

    0 Burnt Mill Rd Unit MDCM2005300, Ridgely, MD 21660

    Welcome to the Oasis neighborhood, a serene and picturesque enclave nestled in the charming town of Ridgely, MD. This prestigious 2.4-acre wooded lot on Burnt Mill Road presents a unique opportunity to craft your dream home amidst nature's splendor. With its perc approval, this lot is primed and ready for you to bring your architectural vision to life. As you enter the Oasis, you're greeted by a

    Agent Photo

    Gretchen Wichlinski

    Compass

    (667) 868-0827

    0 Burnt Mill Rd Unit MDCM2005300, Ridgely, MD 21660
  • /15

    $118,000

    • 3 Beds
    • 1.5 Baths
    • 1,664 Sq Ft

    501 Lincoln St, Denton, MD 21629

    Property is being sold As/ Is. Located on a corner lot. Owner has completed some work to the property, but additional work will be required. Please contact Denton Planning and Codes to verify remaining requirements to obtain an occupancy permit.

    Diane Wenk Wright Real Estate

    501 Lincoln St, Denton, MD 21629
  • /35

    $379,900

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

    22403 Marsh Creek Rd, Preston, MD 21655

    Custom Brick rancher, close to town on large lot. Open floor plan, spacious kitchen, stainless steel appliances, large island. 3 bedrooms, 2 baths, sunroom overlooking yard. Upgrades include new windows, CAC, new roof new electric service and plumbing New Septic and Well, Closing help will be considered

    Barbara Nichols Results Realty Inc.

    22403 Marsh Creek Rd, Preston, MD 21655
  • /19

    $950,000

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

    6401 Laurel Grove Rd, Denton, MD 21629

    Nestled on an expansive 52.08-acre estate, this stunning ranch-style farm offers a harmonious blend of luxury and tranquility, perfect for those seeking an exclusive lifestyle in a serene rural setting. The property boasts a traditional architectural design, complemented by aluminum siding that enhances its timeless appeal. Step inside to discover a thoughtfully designed interior that exudes

    Michelle Anderson Coldwell Banker Premier - Rehoboth

    6401 Laurel Grove Rd, Denton, MD 21629
  • /2

    $79,900

    • Land
    • 9,147 Sq Ft
    • $380,476 per Acre

    6 N Central Ave, Ridgely, MD 21660

    Zoned commercial is this prime lot in the heart of Ridgely and next to the Town Office. Convenient street parking fronting the lot.

    Chuck Jr. Benson and Mangold

    6 N Central Ave, Ridgely, MD 21660

Showing Results 121 - 160, Page 4 of 5

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