Caroline County MD Homes for Sale

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  /38

  $479,000

  • 4 Beds
  • 2.5 Baths
  • 2,747 Sq Ft

  8605 Hickory Place, Denton, MD 21629

  Beautiful Colonial Farmhouse nestled on a wooded lot at the end of a cul-de-sac private lane. This 4 bedroom, 2.5 bath home has been meticulously maintained and features a traditional floor plan with a large kitchen/breakfast area, large family room with vaulted ceilings and a gas fireplace, separate dining room, living room/office. Second floor includes a primary suite with large bathroom with a

  

  Brian Gearhart

  Benson & Mangold, LLC

  8605 Hickory Place, Denton, MD 21629
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  /28

  $595,000

  • 3 Beds
  • 3.5 Baths
  • 3,276 Sq Ft

  23730 Henry Rd, Ridgely, MD 21660

  Beautiful Craftsman Cape Cod on quiet country road in Caroline County. This 3,200 sq ft home was built in 2023 and offers an open floor plan with all the amenities...large family room with vaulted ceilings, private office, large kitchen with white cabinets, farm sink, SS appliances, separate butler's pantry, and separate laundry room, first floor primary with walk-in closet, high-end primary

  

  Brian Gearhart

  Benson & Mangold, LLC

  23730 Henry Rd, Ridgely, MD 21660
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  /87

  $1,550,000

  • 5 Beds
  • 4.5 Baths
  • 4,853 Sq Ft

  322 S 2nd St, Denton, MD 21629

  Wake up to sunrise on the Choptank River and wind down with some of the most stunning sunsets on the Eastern Shore — with Ospreys, Eagles, Herons, and an abundance of wildlife as your daily backdrop. This stunning 4,853 sq ft waterfront estate sits on 2.44 acres with 268 feet of private river frontage, putting you right on the water and just steps from the best of historic downtown Denton. Built

  

  Elizabeth Osborn

  Coldwell Banker Realty

  322 S 2nd St, Denton, MD 21629
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  /63

  $399,000

  $9K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  7392 Todds Wharf Rd, Preston, MD 21655

  This very comfortable rancher with a large high-quality above-ground pool with direct access to sunroom and into the home without getting feet dirty (yeah)! Roomy kitchen and open floor plan allows large gatherings to enjoy the roominess. Working wood-burning fireplace is great for use to heat home all winter or just on-call use when you want the ambiance. Convenient mudroom off garage with

  

  Bonnie Duley

  Long & Foster Real Estate, Inc.

  7392 Todds Wharf Rd, Preston, MD 21655
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  /63

  $1,500,000

  • 3 Beds
  • 3.5 Baths
  • 3,958 Sq Ft

  7347 Harmony Rd, Preston, MD 21655

  Income-producing poultry farm situated on approximately 38.17 acres in desirable Caroline County, featuring four state-of-the-art “Tier 3” tunnel poultry houses with a combined capacity of approximately 110,000 broiler chickens. Built in 1993, the four 40’ x 500’ houses are equipped with Rotem Platinum+ controllers, Shore Time computerized controls, alarm systems, recirculation cooling pads, 6”

  

  Damon Brockenberry

  Keller Williams Preferred Properties

  7347 Harmony Rd, Preston, MD 21655
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  /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

  

  Gretchen Wichlinski

  Compass

  0 Burnt Mill Rd Unit MDCM2005294, Ridgely, MD 21660
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  /16

  $234,900

  • 3 Beds
  • 2.5 Baths
  • 1,440 Sq Ft

  163 Riverwalk Terrace, Federalsburg, MD 21632

  This end unit has units on the left side but no units on the right side, offering more quietness and privacy. This beauty has comfort and "home" written all over. Featuring 3 nice bedrooms of which two bedrooms are upstairs; a convenient half-bath is located on first level. The kitchen is very well designed with lots of beautiful cabinets and countertops. The sink has the window above so you can

  

  Bonnie Duley

  Long & Foster Real Estate, Inc.

  163 Riverwalk Terrace, Federalsburg, MD 21632
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  /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

  

  Bonnie Duley

  Long & Foster Real Estate, Inc.

  PARCEL 91 Cool Spring Rd, Marydel, MD 21649
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  /68

  $349,500

  • 3 Beds
  • 2 Baths
  • 1,436 Sq Ft

  110 N School St, Greensboro, MD 21639

  Pride of ownership is shown from top to bottom in this magnificent rancher! This custom-built home was completed in June 2025 and is like new. The owner took much pride in everything he installed/built and makes this home very desirable. The nine-foot (9') ceilings add the feeling of openness to go with the open floor plan of the living room/dining area/kitchen with an easy flow from one area to

  

  Bonnie Duley

  Long & Foster Real Estate, Inc.

  110 N School St, Greensboro, MD 21639
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  /21

  $195,000

  $20K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,371 Sq Ft

  209 Reliance Ave, Federalsburg, MD 21632

  Charming home situated on approximately half an acre, offering a solid foundation and plenty of potential. This property features 2 bedrooms and 1 full bathrooms, along with a spacious bonus room that can serve as a home office, guest space, or additional living area. The home includes a dedicated laundry area and an eat-in kitchen, perfect for casual dining. With “great bones,” this property is

  

  Charlene Spence

  The Spence Realty Group

  209 Reliance Ave, Federalsburg, MD 21632
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  /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

  

  Gretchen Wichlinski

  Compass

  0 Burnt Mill Rd Unit MDCM2005300, Ridgely, MD 21660
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  /46

  $445,000

  • 4 Beds
  • 2 Baths
  • 1,986 Sq Ft

  25699 Auction Rd, Federalsburg, MD 21632

  Opportunity to purchase this remodeled residence situated on over 18 acres. Improements include new luxury vinyl plank flooring and Advantech subfloors to a fully replaced middle beam for lasting structural integrity. Nearly all windows and doors are brand new, the heating system has been upgraded to an efficient heat pump, and the electrical system now features a 200-amp panel, a dedicated

  Barbara McCaffrey Redfin Corp

  25699 Auction Rd, Federalsburg, MD 21632
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  /50

  $419,000

  • 5 Beds
  • 2.5 Baths
  • 2,382 Sq Ft

  225 S 2nd St, Denton, MD 21629

  Welcome to one of Denton's most charming historic homes, where timeless Victorian architecture, thoughtful updates, and small-town living come together beautifully. Situated on a picturesque corner lot in Denton's historic district, this lovingly maintained five-bedroom home offers more than 2,300 square feet of character-filled living space, abundant natural light, original architectural

  Barbara McCaffrey Redfin Corp

  225 S 2nd St, Denton, MD 21629
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  /41

  $585,000

  $10K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,643 Sq Ft

  24766 Tribbett Cir, Ridgely, MD 21660

  Welcome to this meticulously crafted 2023 contemporary farmhouse, perfectly positioned on a spacious .85-acre lot in the established community of Ashworth. Offering 3,168 square feet, 4 bedrooms, and 2.5 baths, this beautifully designed home blends timeless farmhouse charm with modern finishes and thoughtful upgrades throughout. The striking exterior showcases classic white siding, bold black

  Barbara McCaffrey Redfin Corp

  24766 Tribbett Cir, Ridgely, MD 21660
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  /27

  $369,900

  $5K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 2,268 Sq Ft

  803 Market St, Denton, MD 21629

  This inviting Victorian offers 4 bedrooms and 1.5 baths, that’s perfect for unwinding at the end of the day. Inside, natural light fills the main level, highlighting warm hardwood floors and comfortable living spaces. The living and dining areas connect seamlessly, creating an easy flow for everyday living. The kitchen features ample cabinet and counter space, stainless steel appliances, and a

  Steven Parsons Coldwell Banker Realty

  803 Market St, Denton, MD 21629
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  /73

  $839,000

  • Land
  • 87 Acres
  • $9,644 per Acre

  000 Knife Box Rd, Greensboro, MD 21639

  Located just outside Greensboro in Caroline County, Maryland, this exceptional 87 acre property offers a rare combination of income-producing farmland, diverse wildlife habitat, scenic natural features, and a highly developed hunting setup. The property consists of approximately 50 acres of mature woodland and 37 acres of productive tillable acreage, creating an ideal blend of recreational and

  Mike Arajakis Whitetail Properties Real Estate

  000 Knife Box Rd, Greensboro, MD 21639
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  /16

  $260,000

  • 3 Beds
  • 2 Baths
  • 1,192 Sq Ft

  508 N 6th St, Denton, MD 21629

  Enjoy convenient one-level living on the north side of Denton, just a stone's throw from Bullock's and with easy access to Route 404 for commuting. Built in 2002, this charming 3-bedroom, 2-bath cottage offers a comfortable and functional layout. Enter from the side porch into a welcoming foyer that opens to the spacious living room, featuring a vaulted ceiling and cozy gas fireplace. Upgraded

  Traci Jordan Meredith Fine Properties

  508 N 6th St, Denton, MD 21629
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  /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
• 

  

  /22

  $467,900

  Coming Soon

  • 3 Beds
  • 4 Baths
  • 2,713 Sq Ft

  202 N Central Ave, Ridgely, MD 21660

  Charming Victorian home in the heart of Ridgely, ideally situated on a picturesque, tree-shaded corner lot. This timeless property offers classic character, curb appeal, and a prime location close to local amenities. An expansive wraparound front porch sets the stage for this beautiful home, featuring a gracious entryway, stunning columned foyer, and gleaming hardwood floors that enhance its

  Marcia Rostien Long & Foster Real Estate, Inc.

  202 N Central Ave, Ridgely, MD 21660
• 

  

  /22

  $344,500

  • 4 Beds
  • 2 Baths
  • 1,880 Sq Ft

  2691 Lorraine Ave, Federalsburg, MD 21632

  Discover 2691 Lorraine Ave, Federalsburg, MD 21632. This Cape Cod residence offers a spacious layout situated on over an acre of land at the end of a quiet cul-de-sac. The property features 4 beds, 2 baths, and a welcoming kitchen where all built in appliances stay. Enjoy a large living area with a fireplace and an entry-level bedroom for convenience. Step out onto the back deck to appreciate the

  Norman Domingo XRealty.NET LLC

  2691 Lorraine Ave, Federalsburg, MD 21632
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  /38

  $99,000

  • Land
  • 9,147 Sq Ft
  • $471,429 per Acre

  504 Central Ave, Ridgely, MD 21660

  UPDATE: The New Ridgely Comprehensive Plan draft will designate this lot for future commercial growth alongside the adjoining property—making this a strong investment opportunity. Call to request the documentation. This .21-acre vacant lot is ideally located in the heart of Ridgely. Currently zoned residential, yet future commercial allowance almost finalized - it offers access to public water

  Allie Harris Taylor Properties

  504 Central Ave, Ridgely, MD 21660
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  /32

  $625,000

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

  28402 Liden School Rd, Denton, MD 21629

  This is the one! Approx. 16.77 acres with an owner built 3 bedroom home. One acre with home plus additional acreage. Some acreage is wooded with wild life including, but not limited to, rabbit, deer, and turkey. This home has magnificent kitchen with custom cabinetry and SS appliances, including a 5 burner stove and double wall oven. Pellet stove is included for those cool evenings and damp days.

  Michael Shipley Benson & Mangold, LLC.

  28402 Liden School Rd, Denton, MD 21629
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  /2

  $210,000

  $50K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,280 Sq Ft

  27944 Possum Hill Rd, Federalsburg, MD 21632

  Lovely two bedroom one bath rancher with spacious living room and dining room plus kitchen **1 car garage plus 30 x 30 storage area ** Heating is oil furnace 3 years old** Hot water tank is 3 years old **1.42 acres ** very flat usable lot

  Bev Langley Coldwell Banker Realty

  27944 Possum Hill Rd, Federalsburg, MD 21632
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  /85

  $799,000

  $76K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,149 Sq Ft

  3547 Prchal Rd, Preston, MD 21655

  **Don't Miss This Rare Opportunity**Pride of ownership shines throughout this beautifully appointed property set on over 4 serene acres, including approximately 2.5 wooded acres with private walking trails and an abundance of wildlife. Major 2025 home improvements including a brand new roof, siding and 10 Velux skylights, along with a new Bosch heat pump installed in 2024. This one-of-a-kind

  Amy Endzel Keller Williams Select Realtors of Annapolis

  3547 Prchal Rd, Preston, MD 21655
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  /12

  $78,500

  $57K 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
• 

  

  /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
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  /26

  $390,000

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  25519 Linhard Ln, Greensboro, MD 21639

  Enjoy the peace and privacy of country living on this lovely 4.68-acre property. This well-maintained one-level rancher features durable luxury vinyl plank (LVP) flooring and an upgraded kitchen with elegant quartz countertops, ample cabinetry.This home offers 3 bedrooms and 2 full baths, providing comfortable living space for family and guests. Exterior features include low-maintenance vinyl

  Jimmy White Long & Foster Real Estate, Inc.

  25519 Linhard Ln, Greensboro, MD 21639
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  /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
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  /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
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  /64

  $527,000

  • 4 Beds
  • 2.5 Baths
  • 2,942 Sq Ft

  8590 Briar Patch Dr, Denton, MD 21629

  Enjoy the space and privacy of this beautiful home situated on over 2 acres just outside of Denton. The main level features a formal dining room, a spacious primary suite with separate his-and-her closets, and a private bath with a walk-in shower. The kitchen opens to the family room, creating an inviting space for everyday living and entertaining.Custom window treatments enhance both the

  Barbara Blosser Long & Foster Real Estate, Inc.

  8590 Briar Patch Dr, Denton, MD 21629
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  /21

  $229,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,440 Sq Ft

  103 Riverwalk Terrace, Federalsburg, MD 21632

  Hurry before it’s gone! This is an opportunity to buy in the sold out community of Riverwalk Terrace. The owner stayed at the home a few times some of the appliances never used. Open floor plan 1365 square feet , 3 bedrooms and 2.5 baths easy living. Only 2 years young this unit feels like new, was never a rental barley lived in. also backs up to the woods the private side of the community.

  Kat Thompson Benson & Mangold, LLC.

  103 Riverwalk Terrace, Federalsburg, MD 21632
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  /28

  $299,999

  New Construction $100K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,800 Sq Ft

  210 W 2nd St, Ridgely, MD 21660

  OPEN HOUSE SATURDAY 6/6 12-2 All that’s left to do? Move in and make it yours. Reach out directly about 2-1 buy down with the sellers preferred lender! Brand new. Zero honey-do list. Full peace of mind. Welcome to this newly constructed 4-bedroom, 2-bath home in Ridgely, where modern design meets small-town charm. If you’ve been waiting for that fresh-start feeling — this is it. Step inside to a

  Kenneth Jester Coldwell Banker Realty

  210 W 2nd St, Ridgely, MD 21660
• 

  

  /22

  $184,000

  $5K PRICE DROP

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

  107 Smith St, Federalsburg, MD 21632

  Move-In Ready & Beautifully Remodeled!This charming 3-bedroom, 1.5-bath home offers the perfect blend of comfort and convenience. Enjoy a spacious living room, separate dining area, and a dedicated laundry room for added functionality.The kitchen is designed for both everyday living and entertaining, featuring dual bar seating areas with open views to the living and dining spaces. One

  Dawn Hubbard Keller Williams Select Realtors of Cambridge

  107 Smith St, Federalsburg, MD 21632
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  /27

  $265,000

  • 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, Septic has been inspected and is in acceptable working condition. Stones have been added to the driveway . A few more touches and it is move in ready. Don't wait to view this Newley redone home.

  Barbara Beaudet Brenton Realty Group

  10819 Greensboro Rd, Denton, MD 21629
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  /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
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  /8

  $239,900

  New Construction

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

  205 Park Ave, Federalsburg, MD 21632

  **Construction has not yet began, please feel free to drive by the lot. Completion will be for this August 2026!!*** The photos provided in the MLS are for reference purposes only and are intended to reflect the style and quality of similar fixtures, finishes, and features. Actual materials, fixtures, finishes, and selections may vary based on builder availability and final specifications.

  Erene Katris Coldwell Banker Realty

  205 Park Ave, Federalsburg, MD 21632
• 

  

  /30

  $280,000

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft

  504 Sunset Blvd, Ridgely, MD 21660

  This delightful 3-bedroom bungalow offers a perfect blend of comfort and community. Built in 1940, this home exudes character with its sturdy block construction and inviting layout. The cozy 864 sq. ft. interior is complemented by essential appliances, including a refrigerator, stove, washer, and dryer, making daily living a breeze. The generous half-acre lot provides ample outdoor space for

  Cheryl Knotts Chesapeake Real Estate Associates, LLC

  504 Sunset Blvd, Ridgely, MD 21660
• 

  /2

  $27,500

  • Land
  • 12,196 Sq Ft
  • $98,214 per Acre

  0 Charlotte Ave, Federalsburg, MD 21632

  Build your dream home in the heart of Federalsburg! This approximately 0.28-acre residential lot is located within town limits and is zoned R-1 Single Family Residential. Public water and public sewer are available, offering a great opportunity for new construction in an established community. Conveniently located near local parks, schools, shopping, dining, and major commuter routes. Whether

  Heather Brummell Keller Williams Realty

  0 Charlotte Ave, Federalsburg, MD 21632
• 

  

  /12

  $575,000

  • Land
  • 61.88 Acres
  • $9,292 per Acre

  17619 Melville Rd, Henderson, MD 21640

  The Melville Rd Farm is located on the east side of Melville Road and is bordered to the north by Trunk Line Road. The property includes approximately 51± acres of tillable ground along with 11± acres of wooded areas primarily situated around drainage ditches, providing natural transitions and wildlife cover. Two transmission lines run through the center of the farm, offering access corridors and

  Benjamin Alder The Land Group

  17619 Melville Rd, Henderson, MD 21640
• 

  

  /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 throughout

  Stephan Strothe Washington Fine Properties, LLC

  0 Burnt Mill Rd Unit MDCM2006400, Ridgely, MD 21660

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