Caroline County MD Homes for Sale

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  /102

  $1,395,000

  • 4 Beds
  • 3.5 Baths
  • 3,356 Sq Ft

  23296 Wilder Way, Denton, MD 21629

  Right out of HGTV! Custom Built in 2020, this 3,350+/- sq ft one-level home offers an abundance of amenities including high ceilings, 4 bedrooms, 3.5 Baths, large open floorplan with huge gourmet kitchen with quartz/ss appliances, separate pantry, family room with stacked stone gas fireplace. The Primary Bedroom is located at one end of the house and includes a large bath with double vanity,

  

  Brian Gearhart

  Benson & Mangold, LLC

  (410) 376-8486

  23296 Wilder Way, Denton, MD 21629
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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

  (667) 282-1883

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

  

  Gretchen Wichlinski

  Compass

  (667) 297-6243

  0 Burnt Mill Rd Unit MDCM2005298, Ridgely, MD 21660
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  /60

  $679,000

  • 3 Beds
  • 2 Baths

  28402 Liden School Rd, Denton, MD 21629

  Private serene living at its finest! This 15.77 acres is included with one-acre parcel with the rancher on it for a total of 16.77 acres according to tax records. This property has it all -- gorgeous rancher with 3 BR and 2 full baths; large walk-in pantry in the kitchen, family room with pellet stove and brick fireplace that can burn wood if buyer desires to do so; two large walk-in closets in

  

  Bonnie Duley

  Long & Foster Real Estate, Inc.

  (410) 421-7747

  28402 Liden School Rd, Denton, MD 21629
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  /14

  $124,900

  • 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 4=bedroom home. 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 SRA noted on it so lots of the necessary paperwork is completed. So come see and come buy and be

  

  Bonnie Duley

  Long & Foster Real Estate, Inc.

  (410) 650-6268

  PARCEL 91 Cool Spring Rd, Marydel, MD 21649
• 

  

  /20

  $215,000

  • 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

  (443) 241-6882

  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

  (667) 868-0827

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

  

  /20

  $174,500

  • 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 and

  

  Bonnie Duley

  Long & Foster Real Estate, Inc.

  (410) 453-1053

  21948 Main St, Hillsboro, MD 21641
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  /63

  $407,500

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

  7392 Todds Wharf Rd, Preston, MD 21655

  This comfortable rancher with a large 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 washer and dryer on

  

  Bonnie Duley

  Long & Foster Real Estate, Inc.

  (667) 843-7490

  7392 Todds Wharf Rd, Preston, MD 21655
• 

  

  /41

  $595,000

  • 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
• 

  

  /27

  $375,000

  • 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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  /34

  $315,000

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

  8409 Harmony Rd, Denton, MD 21629

  Tucked away in a peaceful rural setting, this beautifully updated home offers space, privacy, and modern convenience on 1.14 acres. Welcome to 8409 Harmony Road—a truly special property with access from both Harmony Road and the rear of the property via Towers Road, providing added flexibility and convenience. This move-in-ready 3-bedroom, 2-bath home blends thoughtful updates with a functional

  Barbara McCaffrey Redfin Corp

  8409 Harmony Rd, Denton, MD 21629
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  /66

  $429,000

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

  225 S 2nd St, Denton, MD 21629

  Historic Victorian home with modern updates on a fenced corner lot—5 bedrooms, bonus rooms, deck, and over 2,300 sq ft just blocks from downtown Denton and the Choptank River. Built in 1906, this beautifully updated home offers 2,382 sq ft, 5 bedrooms, and 2.5 baths on a spacious .29-acre corner lot setting with a classic white picket fence and private fenced yard—perfect for outdoor living and

  Barbara McCaffrey Redfin Corp

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

  

  /22

  $525,000

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft

  8664 Mitchell Rd, Denton, MD 21629

  Nestled on a serene 5.64-acre lot, this charming ranch-style home offers a perfect blend of comfort and modern living in a tranquil rural setting. Built in 2003, (New Roof in January 2026!) this well-maintained residence boasts 2,100 square feet of thoughtfully designed space, featuring three spacious bedrooms and two full bathrooms, ideal for relaxation and everyday living. Step inside to

  Cheryl Knotts Chesapeake Real Estate Associates, LLC

  8664 Mitchell Rd, Denton, MD 21629
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  /41

  $349,900 Coming Soon

  • 4 Beds
  • 2 Baths
  • 1,700 Sq Ft

  221 Apple Ln, Preston, MD 21655

  Some homes check one or two boxes. This one checks all of them, and does it for under $350,000.Four bedrooms, two full baths, a fenced backyard, a pool, and open farmland views behind the property. In today's market, that combination at this price point is genuinely rare. This is the kind of home first-time buyers dream about and out-of-area buyers can't believe exists when they start

  Alex Archer Real Broker, LLC - Annapolis

  221 Apple Ln, Preston, MD 21655
• 

  /2

  $324,900 Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 1,848 Sq Ft

  411 Mallard Dr, Greensboro, MD 21639

  Located in the charming community of Caroline Farms in Greensboro, MD, this delightful Colonial-style home offers a perfect blend of comfort and convenience. Built in 2006, this well-maintained residence boasts 1,848 square feet of living space, providing ample room for relaxation and entertaining. As you approach the home, you'll be greeted by its inviting vinyl siding and a well-manicured front

  Vincent Payne Realty Navigator

  411 Mallard Dr, Greensboro, MD 21639
• 

  

  /47

  $674,999

  • 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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  /28

  $369,500 New Construction

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

  210 W 2nd St, Ridgely, MD 21660

  ***OPEN HOUSE SATURDAY 4/25 FROM 12-2*** 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 bright, open layout designed for real life. The spacious living area flows seamlessly into the kitchen and

  Kenneth Jester Coldwell Banker Realty

  210 W 2nd St, Ridgely, MD 21660
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  /55

  $635,000

  • 4 Beds
  • 2.5 Baths
  • 2,700 Sq Ft

  11142 Log Cabin Rd, Denton, MD 21629

  Welcome to 11142 Log Cabin Road! This unique property offers the perfect combination of residential living and valuable commercial space, all on one expansive, 4.53 acre lot. This beautiful colonial-style home has great curb appeal with its classic look, neatly trimmed landscaping, and a spacious front yard shaded by mature trees. The main home spans over 2,700 square feet and features four

  Courtney Gallagher Keller Williams Realty Central-Delaware

  11142 Log Cabin Rd, Denton, MD 21629
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  /65

  $624,900

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

  322 Deep Shore Rd, Denton, MD 21629

  This home is anything but ordinary. Thoughtfully built by the current owners in 1982, the property showcases true craftsmanship with structural beams hewn from timber sourced right from the land itself. The main living space is situated on the second floor, offering a bright, airy layout and sweeping views across 13 picturesque acres. The first floor provides incredible flexibility—ideal for

  Connie Loveland Benson & Mangold, LLC

  322 Deep Shore Rd, Denton, MD 21629
• 

  

  /29

  $319,000

  • 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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  /2

  $485,000 Coming Soon

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

  12397 Ridgely Rd, Ridgely, MD 21660

  Picture your horse here! Grazing in lush pastures safely fenced with Electro-Braid, training in the round pen or the 60' x 120' dressage arena, or resting in one of 4 fully matted stalls with fans in the main barn (there are two more stalls in the other stable along with hay storage.) In the main barn, two of the stalls can be joined to create a foaling stall with a monitor camera!For the

  Deborah Dawkins Coldwell Banker Realty

  12397 Ridgely Rd, Ridgely, MD 21660
• 

  

  /49

  $324,900

  • 4 Beds
  • 2 Baths
  • 2,448 Sq Ft

  522 Market St, Denton, MD 21629

  Investor special in the heart of Denton! This duplex at 522 Market St offers incredible potential for the right buyer looking to add value and build equity. Featuring two separate units, each level includes 2 bedrooms and 1 full bathroom, providing a functional layout ideal for rental income or multi-generational living. This also has potential to be converted back into a single family

  Mike Lee Elmore EXP Realty, LLC

  522 Market St, Denton, MD 21629
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  /27

  $334,000

  • 3 Beds
  • 1.5 Baths
  • 1,622 Sq Ft

  207 S 7th St, Denton, MD 21629

  3BR, 1.5BA home on LARGE in town lot featuring Corian countertops, hardwood floors and built-in bookshelves. Enjoy a welcoming front porch and screened breezeway connecting a 2 car attached garage with additional lean-to storage. Roof replaced 2021. Full Walkout Dry basement with French drain and sump pump. Convenient in town location close to local amenities, all that is missing is your car in

  Amy Betts Coldwell Banker Realty

  207 S 7th St, Denton, MD 21629
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  /64

  $399,000

  • 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!

  Megan Rosendale Rosendale Realty

  8578 Tuckahoe Rd, Denton, MD 21629
• 

  

  /50

  $379,000

  • 7 Beds
  • 4 Baths
  • 3,376 Sq Ft

  23267 Shady Oak Ln, Denton, MD 21629

  This is an idea for a description: "Welcome to 23267 Shady Oak Lane in Denton, MD - a spacious property set on over 4 acres. This 7-bedroom, 4-bath home offers 3,376 sq ft of living space, along with a detached 2-car garage and a private, wooded setting. The home offers a solid layout and is ready for updates, making it a great opportunity for buyers looking to renovate and create their ideal

  Mike Cowan Coldwell Banker Realty

  23267 Shady Oak Ln, Denton, MD 21629
• 

  

  /26

  $369,000

  • 3 Beds
  • 2 Baths
  • 2,412 Sq Ft

  1302 Trice Meadows Cir, Denton, MD 21629

  Lovely Raised Rancher consisting of 2,412 square feet of living with the main level having 3 bedrooms, 2 bathrooms, office/den, living room, kitchen and laundry area with a split floor plan of the bedrooms and the owner's suite on the opposite end of house. No worries about parking your vehicles with this nice 2 car attached garage and on street parking. Additionally, the second floor 52x15 bonus

  George Thompson Long & Foster Real Estate, Inc.

  1302 Trice Meadows Cir, Denton, MD 21629
• 

  

  /29

  $329,900

  • 4 Beds
  • 1.5 Baths
  • 1,350 Sq Ft

  115 Boyce Mill Rd, Greensboro, MD 21639

  Welcome to this charming, Cape-Cod with a Full Unfinished basement—perfectly nestled on a spacious 1/2 Acre! This property gives you that “welcome home” feeling the moment you arrive. Inside, you’ll find a bright and inviting living area featuring a cozy electric fireplace insert and beautiful wood‐beam accents. The freshly renovated kitchen is thoughtfully designed and opens seamlessly to the

  Kathleen Brenton Brenton Realty Group

  115 Boyce Mill Rd, Greensboro, MD 21639
• 

  

  /13

  $349,900

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  21611 Everlea Dr, Preston, MD 21655

  Welcome to this estate sale opportunity offering convenient one-level living in a wonderful, well-established community just minutes from Easton and St. Michaels. Lovingly owned by the original owner, this 3-bedroom, 2-bath home is ready for its next chapter. The home features a functional floor plan with spacious living areas and offers great potential for updates to match your personal style.

  Nicole Giordano Coldwell Banker Waterman Realty

  21611 Everlea Dr, Preston, MD 21655
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  /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
• 

  

  /18

  $340,000

  • 3 Beds
  • 2.5 Baths
  • 2,286 Sq Ft

  27279 Jenny Hye Ln, Marydel, MD 21649

  Welcome to Your Peaceful Retreat!This 3-bedroom, 2.5-bath split-foyer home offers 1,488 sq. ft. of comfortable living space, plus a full basement and an attached one-car garage. With its classic brick-and-siding exterior, inviting front patio, and serene surroundings, this property blends warmth, character, and endless potential.Step inside and imagine the possibilities—a bright, open

  Hudson Post Keller Williams Select Realtors of Easton

  27279 Jenny Hye Ln, Marydel, MD 21649
• 

  

  /15

  $314,900

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

  506 Pintail St, Greensboro, MD 21639

  Nearly new ranch style home with large front porch. Three bedrooms and two full baths plus spacious laundry room enhance this home. Large kitchen with center island with stainless appliances and granite countertops are a focal point of this open floor plan. Move in ready and waiting for a new family!

  Bonnie Johnson Keller Williams Realty

  506 Pintail St, Greensboro, MD 21639
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  /62

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,588 Sq Ft

  1010 S 2nd St, Denton, MD 21629

  Nestled on the edge of town, 1010 S 2nd Street delivers the convenience of in-town living without in-town taxes. Situated on 1.06 beautifully landscaped acres with mature plantings, this 3-bedroom, 2-bath home offers a spacious feel inside and out. Interior features include hardwood, LVP, and tile flooring, along with a cozy pellet stove fireplace insert for efficient heating, complemented by hot

  Roger Boyce Chesapeake Real Estate Associates, LLC

  1010 S 2nd St, Denton, MD 21629
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  /28

  $399,000 New Construction

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

  1 Sunrise Ave, Ridgely, MD 21660

  As morning light rises over Sunrise Village, this home, The Sunshine, thoughtfully crafted by local builder Lomaxx Custom Homes comes to life. Golden light spills across the nearby fields and settles gently indoors, where days begin with coffee on the porch, birds gliding by, and daylight drifting through the windows, filling each room with a calm, welcoming glow. Designed for easy, everyday

  Crystal Smith RE/MAX Executive

  1 Sunrise Ave, Ridgely, MD 21660
• 

  

  /43

  $339,900

  • 4 Beds
  • 2 Baths
  • 1,440 Sq Ft

  147 Mill St, Preston, MD 21655

  Well Maintained 4 Bed 2 Full Bath Cape Cod. Large Eat-in Kitchen w/ Stainless Steel Appliances, Granite Countertops and Center Island!Nice Size Family Room. Outdoors feature a Large Shed with Heat and Air (currently used as a very nice office) , Separate Shed for storage at the back of Spacious level Lot. Patio for entertaining and more... Home is less than 1 Mile to Choptank River Landing!

  Kathleen Brenton Brenton Realty Group

  147 Mill St, Preston, MD 21655
• 

  

  /52

  $314,900 Coming Soon

  • 4 Beds
  • 3 Baths
  • 1,608 Sq Ft

  529 Liberty Rd, Federalsburg, MD 21632

  There's one thing you almost never find at this price point in Caroline County: a full detached living space that's completely finished and ready to use on day one. This one has it.Set on a quiet stretch in Federalsburg, this four-bedroom, three-bath home has been thoroughly updated from top to bottom. Every major system has been replaced within the last ten years. Roof, HVAC, water heater,

  Alex Archer Real Broker, LLC - Annapolis

  529 Liberty Rd, Federalsburg, MD 21632
• 

  

  /39

  $399,500

  • 4 Beds
  • 2.5 Baths
  • 2,730 Sq Ft

  315 Morning Glory Dr, Denton, MD 21629

  From the moment you step inside, this gorgeous Colonial immediately feels like home. Thoughtfully designed with a 5-foot bump-out extension and a highly desirable open floor plan, the layout offers both space and functionality for everyday living and entertaining. The living room is filled with natural light thanks to an added third window, creating a bright and inviting atmosphere that carries

  Crystal Smith RE/MAX Executive

  315 Morning Glory Dr, Denton, MD 21629
• 

  

  /30

  $375,000

  • 4 Beds
  • 2 Baths
  • 1,568 Sq Ft

  24383 Robins Creek Rd, Preston, MD 21655

  VERY NICE 3-4 BEDROOM, 2 BATH HOME IN TWO JOHNS WATERFRONT COMMUNITY. BOAT LANDING APPROXIMATELY 1/4 MILE AWAY. LARGE LIVING ROOM, KITCHEN-DINING ROOM COMBO, PANELED WALLS ARE ALL PAINTED, MOSTLY WOOD FLOORS. LARGE DECK AT REAR OF HOUSE. PATIO AREA WITH A NICE FIRE PIT FOR EVENING ENJOYMENT. MORE PICTURES TO COME SOON. ONLY 40 MILES TO WESTERN SHORE, LESS THAN 60 MILES TO THE BEACH

  Ed Quidas Long & Foster Real Estate, Inc.

  24383 Robins Creek Rd, Preston, MD 21655
• 

  

  /15

  $135,000

  • 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

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