Caroline County MD Homes for Sale

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  /24

  $258,900

  • 2 Beds
  • 2 Baths
  • 606 Sq Ft

  318 Carter Ave, Denton, MD 21629

  This charming bungalow, fully renovated in 2020 and move-in ready, blends modern comfort with timeless appeal. Behind the classic covered front porch, an open, light-filled layout offers two bedrooms and two full bathrooms on a single level. The living and kitchen area features a vaulted ceiling with recessed lighting, enhancing the sense of space and adding a clean, modern feel to this efficient

  Georgi Chauvin Benson & Mangold, LLC

  318 Carter Ave, Denton, MD 21629
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  /50

  $549,000 Open Sat 11AM - 1PM

  • 4 Beds
  • 2.5 Baths
  • 3,442 Sq Ft

  5585 Harmony Woods Dr, Preston, MD 21655

  Set on a private, wooded 1.37± acre lot in Harmony Woods, this beautifully maintained home offers a warm, inviting layout with abundant natural light and thoughtful updates throughout. A welcoming front porch leads into the main level with hardwood floors, detailed trim work, and easy flow from the kitchen and breakfast area to the living room with a wood-burning fireplace. Full-view doors open

  Georgi Chauvin Benson & Mangold, LLC

  5585 Harmony Woods Dr, Preston, MD 21655
• 

  $274,990 New Construction

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

  123 Park Ave, Greensboro, MD 21639

  Explore 123 Parkland Road, a new home under-construction in the quaint Kinnamon Meadows community of Greensboro, MD. 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

  D.R. Horton Builder

  123 Park Ave, Greensboro, MD 21639
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  /2

  $399,000 Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft

  24029 Meadows Dr, Ridgely, MD 21660

  Enjoy the best of Eastern Shore living with the tranquility of a quiet, country setting while remaining conveniently located just outside of the quaint little town of Ridgely. This nanticoke rancher features a nice family room addition off the kitchen and is located on a private 2 acre lot on the end of a cul-de-sac. Featuring 3 bedrooms and 2 full baths and a two car garage. This property also

  Samantha Grimes Chesapeake Real Estate Associates, LLC

  24029 Meadows Dr, Ridgely, MD 21660
• 

  

  

  /23

  $286,990 New Construction

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

  203 Hobbs St, Greensboro, MD 21639

  Welcome to 203 Hobbs Street, a new home under construction in Kinnamon Meadows in Greensboro, MD. 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

  D.R. Horton Builder

  203 Hobbs St, Greensboro, MD 21639
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  /9

  $169,000

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

  106 S 6th St, Denton, MD 21629

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

  Amy Betts Coldwell Banker Realty

  106 S 6th St, Denton, MD 21629
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  /23

  $384,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,292 Sq Ft

  8 Sunrise Ave, Ridgely, MD 21660

  This modern "Farmhouse" Rancher is thoughtfully designed and constructed by the reputable Lomaxx Custom Homes, offering the perfect combination of style, functionality, and comfort. This beautiful home features 3 bedrooms, 2 full bathrooms, and an inviting open-concept layout—ideal for both everyday living and entertaining. High-end finishes come standard, including luxury vinyl plank flooring, a

  Amy Betts Coldwell Banker Realty

  8 Sunrise Ave, Ridgely, MD 21660
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  /9

  $429,900 Open House 12/06

  • 4 Beds
  • 2.5 Baths
  • 2,248 Sq Ft

  26091 Hokum Dr, Greensboro, MD 21639

  Discover peaceful Eastern Shore living in this beautiful 4-bedroom, 2.5-bath detached home, set on 7.55 private acres bordering the Choptank River. Tucked away at the end of a quiet cul-de-sac with mature woods, this property offers exceptional privacy, nature views, and seasonal glimpses of the river during the fall and winter months. Inside, the home has been thoughtfully refreshed with

  

  Lori Marino

  Long & Foster Real Estate, Inc.

  (410) 835-4869

  26091 Hokum Dr, Greensboro, MD 21639
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  /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
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  /5

  $198,500

  • 3 Beds
  • 1 Bath
  • 1,350 Sq Ft

  6561 Bell Creek Rd, Preston, MD 21655

  Looking for peace, privacy, and wide-open views?Escape the subdivision life — no HOA, no close neighbors, just you and open fields. This charming property, tucked back from the road and surrounded by farmland, has been lovingly held since 1972. Traditional styling and ready for a your new chapter. The home is livable, but will not qualify for USDA, Rural Home or VA. Pinterest, AI and bring

  Barbara Dayton Long & Foster Real Estate, Inc.

  6561 Bell Creek Rd, Preston, MD 21655
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  /11

  $240,000

  • 3 Beds
  • 2.5 Baths
  • 1,709 Sq Ft

  1412 Blue Heron Dr, Denton, MD 21629

  Welcome home! Come and check out this 3 bed 2.5 bath End Unit Townhouse located in the highly desired Mallard Landing Community. This beautiful townhome is newly renovated and ready for it's new owners! The main level encompasses a natural bright and spacious living area, kitchen, and half bathroom. Perfect for entertaining and functional living. The second level has a laundry room, 2 well sized

  Romont Fletcher Keller Williams Flagship

  1412 Blue Heron Dr, Denton, MD 21629
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  /50

  $642,900

  • 4 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. Expansive lot sizes give you the privacy needed within a walkable neighborhood. Sit in your rocker with a cocktail while enjoying the dream turned into a reality of a wrap-around porch. A large rear screened-in porch to watch the local wildlife opens onto extensive

  Juliet Wells Coldwell Banker Chesapeake Real Estate Company

  24276 Asbury Dr, Denton, MD 21629
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  /7

  $875,000 Coming Soon

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

  3547 Prchal Rd, Preston, MD 21655

  Pride of ownership shines throughout this home, lovingly maintained since 1992. A major renovation in 2006 nearly doubled the living space, transforming this property into a spacious 4-bedroom, 3-bathroom home ideal for comfortable living and entertaining.The impressive 20' x 27' kitchen is the heart of the home, featuring cherry cabinetry, quartz countertops, a walk-in pantry, and a cozy

  Amy Endzel Keller Williams Select Realtors of Annapolis

  3547 Prchal Rd, Preston, MD 21655
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  /2

  $355,000 Coming Soon

  • 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 2-bedroom, 1.5-bath residence has been completely remodeled from top to bottom with modern design and high-end finishes throughout. The home features all-new walls, bathrooms, appliances, kitchen cabinets/countertops and luxury vinyl plank flooring throughout, with carpet in the bedrooms.

  Lisa Magnus Clark & Co Realty, LLC

  13306 Greensboro Rd, Greensboro, MD 21639
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  /35

  $279,000

  • 2 Beds
  • 1 Bath
  • 1,140 Sq Ft

  3540 Houston Branch Rd, Federalsburg, MD 21632

  Welcome to 3540 Houston Branch Rd. It was purchased in 2021 and has undergone extensive renovations. The interior was taken down to the studs. There is new drywall, flooring and sub flooring, a complete bath room, windows, kitchen cabinets, appliances and quartz counter tops. Even the electric was updated along with plumbing. Did I mention a new roof, well and septic system!! This is a perfect

  Eddie Matthews Benson & Mangold, LLC

  3540 Houston Branch Rd, Federalsburg, MD 21632
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  /10

  $318,000

  • 2 Beds
  • 1 Bath
  • 1,438 Sq Ft

  4935 Edmondson Creek Rd, Preston, MD 21655

  Approximately 2 acres (parcels 289, 196) on a point on Little Creek off the Choptank River. Two bedroom, one bath log cabin with loft. An additional accessary log cabin. Easy access to Easton or Preston. Great waterfowl location.

  Randy Staats Benson & Mangold, LLC

  4935 Edmondson Creek Rd, Preston, MD 21655
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  /24

  $280,000

  • 3 Beds
  • 1 Bath
  • 1,392 Sq Ft

  8259 Haven St, Denton, MD 21629

  This adorable 3-bedroom residence is located between Easton and Denton. Situated on a spacious one acre lot offering a perfect blend of comfort and low maintenance. Inside offers a lovely sunroom full of natural light, living room with newer flooring, kitchen has updated appliances and separate dining area and three cozy bedrooms with hall bath. Nice rear deck overlooking back yard. The expansive

  Barbara Watkins Benson & Mangold, LLC

  8259 Haven St, Denton, MD 21629
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  /48

  $362,000

  • 3 Beds
  • 2 Baths
  • 1,640 Sq Ft

  334 Deep Shore Rd, Denton, MD 21629

  Welcome to this adorable 3 bedroom, 2 bath home in the heart of Denton located on a generous 0.46 acre lot that backs up to trees. There is a short walk to Martinak State Park. Inside you will enjoy the recently updated home which includes a new roof, new HVAC, new water heater, water softener system. The bathroom and kitchen has been remodeled. You will see the beautifully refinished living room

  Laura Anthony Benson & Mangold, LLC

  334 Deep Shore Rd, Denton, MD 21629
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  /19

  $330,000 Open Sat 10AM - 1PM

  • 5 Beds
  • 2 Baths
  • 2,574 Sq Ft

  305 Central Ave, Ridgely, MD 21660

  Welcome home to this spacious 5-bedroom, 2-bath Colonial located in the heart of Ridgely. This in-town property offers a large kitchen with plenty of space for cooking and entertaining, a comfortable living room, and generously sized bedrooms throughout. The traditional floor plan provides a warm and inviting flow, perfect for both daily living and hosting guests. Enjoy the convenience of being

  Katie Moore Coldwell Banker Chesapeake Real Estate Company

  305 Central Ave, Ridgely, MD 21660
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  /35

  $361,000

  • 3 Beds
  • 2.5 Baths
  • 1,734 Sq Ft

  206 Charles St, Federalsburg, MD 21632

  This 3-bedroom, 2.5-bath Cape Cod sits on a quiet street surrounded by mature trees. Features include a covered front porch with recessed lighting, family room, formal dining room, eat-in kitchen with stainless steel appliances, and first-floor laundry. Enjoy a fully fenced backyard with a spacious deck and a basketball court in the front yard. Transform the bonus space above the two-car garage

  

  Rosezette Dennis

  Coldwell Banker Realty

  (410) 705-7651

  206 Charles St, Federalsburg, MD 21632
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  /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
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  /20

  $259,990 New Construction

  • 2 Beds
  • 2 Baths
  • 1,059 Sq Ft

  120 Parkland Rd, Greensboro, MD 21639

  Discover the Perry in Kinnamon Meadows, a 1,059 square foot open concept cottage-style ranch home, offering two bedrooms and two bathrooms at 124 Parkland Road in Greensboro, MD. 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

  D.R. Horton Builder

  120 Parkland Rd, Greensboro, MD 21639
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  /25

  $219,000

  • 3 Beds
  • 1 Bath
  • 1,350 Sq Ft

  115 Boyce Mill Rd, Greensboro, MD 21639

  This property is full of character, rare to find beautiful pine paneling in its natural state. With Built-in book shelves and hard wood flooring under the carpets original to the house. A spare room on the first floor could be used as a 4th bedroom . The basement has room for expansion as well. The back deck is great for entertaining or just enjoying the view. Solid house making this appealing to

  Kat Thompson Benson & Mangold, LLC.

  115 Boyce Mill Rd, Greensboro, MD 21639
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  /32

  $325,000

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

  121 Edenton Ln, Denton, MD 21629

  This charming rancher offers 3 bedrooms and 2 full bathrooms, nestled on a spacious .5-acre lot. Recent updates include new LVP flooring throughout, a roof replacement in 2018, and newer HVAC and water heater (both replaced in 2017). Outside enjoy a deck, patio, and large treelined backyard, offering privacy. Located just minutes from downtown Denton and major commuter routes, this home is

  Alicia Gannon Dulin Benson & Mangold, LLC

  121 Edenton Ln, Denton, MD 21629
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  /43

  $440,000

  • 4 Beds
  • 3 Baths
  • 3,212 Sq Ft

  21405 Tanyard Rd, Preston, MD 21655

  Peaceful Country Living on 3.2 Acres – Recently Renovated Home with Expansive Pole Barn! Welcome to 21405 Tanyard Rd in Preston, MD – where modern updates meet serene country living. This beautifully renovated 4-bedroom, 3-bath home sits on 3.2 acres—perfect for gardening, raising animals, or simply enjoying wide-open space and quiet surroundings. Step inside to find a bright, freshly updated

  Justin Pokrywka Taylor Properties

  21405 Tanyard Rd, Preston, MD 21655
• 

  

  /19

  $315,000

  • 3 Beds
  • 2 Baths
  • 920 Sq Ft

  25607 Garey Rd, Denton, MD 21629

  This inviting 3-bedroom, 2-bath rancher sits on 1.25 peaceful acres and is full of thoughtful updates and outdoor features you'll love. Step inside to find fresh paint, new carpet, durable LVP flooring, and newer appliances—all in a comfortable, move-in ready layout. The exterior offers just as much to enjoy: a large backyard, spacious deck, patio, and a storage shed for all your tools or toys. A

  Kaitlyn Collins Benson & Mangold, LLC

  25607 Garey Rd, Denton, MD 21629
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  /6

  $2,999,000 Coming Soon

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

  4218 Harmony Rd, Preston, MD 21655

  COMING SOON — A True Eastern Shore Estate! Experience unparalleled living at this magnificent 58+ acre Preston estate, an extraordinary opportunity to own a property that perfectly blends luxury, comfort, and versatility. The stately main residence features 5 bedrooms, 6 full and 3 half baths, and an impressive foyer with a grand double staircase. Entertain with ease in the gourmet kitchen with

  Donna Harrington Coldwell Banker Realty

  4218 Harmony Rd, Preston, MD 21655
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  /38

  $230,000

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

  1403 Blue Heron Dr, Denton, MD 21629

  Welcome Home to Low-Maintenance Living! 1403 Blue Heron Drive, Denton Step inside this cozy, turn-key 3-level townhome nestled in the highly desired Mallard Landing community! Boasting over 1,680 sq ft, this 3-bedroom, 2.5-bath residence.. The open-concept main floor is perfect for gatherings, flowing seamlessly from living to dining. Plush carpet leads you to the private, entire-floor Master

  Dale Hunter Bayside Realty

  1403 Blue Heron Dr, Denton, MD 21629
• 

  $292,990 New Construction

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

  125 Park Ave, Greensboro, MD 21639

  Welcome to 125 Parkland Road, a new home under construction in our newest community Kinnamon Meadows in Greensboro, MD. The Helena is an inviting 1,460 square foot cottage-style ranch home that offers four bedrooms, two bathrooms, and a one-car garage. The long, welcoming foyer of this home allows for the three guest bedrooms and guest bathroom to be separate from the living areas of the home.

  D.R. Horton Builder

  125 Park Ave, Greensboro, MD 21639
• 

  $292,990 New Construction

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

  131 Hobbs St, Greensboro, MD 21639

  Welcome to 131 Hobbs Street, a new home soon to be under construction in our newest community, Kinnamon Meadows in Greensboro, MD. The Helena is an inviting 1,460 square foot cottage-style ranch home that offers four bedrooms, two bathrooms, and a one-car garage. The long, welcoming foyer of this home allows for the three guest bedrooms and guest bathroom to be separate from the living areas of

  D.R. Horton Builder

  131 Hobbs St, Greensboro, MD 21639
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  /26

  $296,000

  • 3 Beds
  • 2 Baths
  • 1,368 Sq Ft

  229 Oldtown Rd, Goldsboro, MD 21636

  Fully Remodeled 3 Bedroom, 2 Bath Home in the Heart of Goldsboro, MD Welcome to 229 Main Street, where modern style meets small-town charm. This beautifully remodeled 3-bedroom, 2 full bath home has been thoughtfully updated from top to bottom, offering the perfect blend of craftsmanship and comfort. Step inside to a bright, open floor plan featuring luxury vinyl plank flooring, fresh neutral

  Brett Schrader Taylor Properties

  229 Oldtown Rd, Goldsboro, MD 21636
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  /2

  $469,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft

  13364 River Rd, Greensboro, MD 21639

  TIME IS RUNNING OUT TO PICK YOUR FINISHES! Under construction....Discover this stunning, newly built ranch-style home situated on a spacious 2.6 acre unrestricted lot. Perfect for those seeking privacy and tranquility, this beautifully appointed residence features 3 bedroom and 2 bathrooms, attached 2 car garage, rear deck, offering comfortable living in a serene setting. Thoughtfully designed

  Linda Moore Long & Foster Real Estate, Inc.

  13364 River Rd, Greensboro, MD 21639
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  /59

  $325,000

  • 2 Beds
  • 1 Bath
  • 1,528 Sq Ft

  506 Park Ave, Ridgely, MD 21660

  Welcome to this delightful 2-bedroom, 1-bath rancher nestled in the heart of Ridgely. Perfectly positioned on a spacious double lot, this home offers abundant outdoor space—ideal for gardening, entertaining, or future expansion. A brand-new roof adds peace of mind and long-term value. Step inside to discover a bright and functional layout featuring a sun-drenched sunroom, a cozy living room with

  Lisa Lynch Keller Williams Realty

  506 Park Ave, Ridgely, MD 21660
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  /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
• 

  

  /46

  $699,000

  • 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. The grounds feature expansive pastures secured by electric fencing, a well-equipped horse barn with stables that measures 36X64, and two convenient run-in sheds.

  Billy Mister Keller Williams Realty

  4757 Long Swamp Rd, Federalsburg, MD 21632
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  /43

  $260,000

  • 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
• 

  

  /46

  $399,000

  • 4 Beds
  • 2.5 Baths
  • 2,176 Sq Ft

  8548 Dogwood Blossom Ln, Denton, MD 21629

  Welcome to this well maintained Colonial on a very private road. Home only needs a little updating. Bones are Great! Home features 3 Large Bedrooms upsatirs with a Full bath in hallway. 1 Very Spacious Primary Bedroom with Two closets and a Full Bath. Downstairs you will enjoy ALL the space. Lovely Eat-in Kitchen, Separate Dining Room, Family Room w/ Wood Stove, Living Room, Laundry Room

  Kathleen Brenton Brenton Realty Group

  8548 Dogwood Blossom Ln, Denton, MD 21629
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  /43

  $425,000

  • 5 Beds
  • 2 Baths
  • 2,061 Sq Ft

  8025 Laurel Ln, Denton, MD 21629

  Southern Charm Meets Modern Comfort! Step into your own Magnolia Magazine dream home! This 5-bedroom, 2-bath beauty sits on a serene 1-acre lot filled with timeless Southern character and modern updates throughout. From the adorable front and back decks to the charming porch swing, every detail of this property invites you to slow down and savor the good life. Inside, you’ll find a bright, open

  Josh Dill Home Towne Real Estate

  8025 Laurel Ln, Denton, MD 21629
• 

  

  /125

  $1,295,000

  • 4 Beds
  • 3.5 Baths
  • 4,496 Sq Ft

  24800 Pealiquor Rd, Denton, MD 21629

  Experience timeless elegance and Eastern Shore charm at this beautifully restored 4-bedroom, 3.5-bath colonial retreat set on 7 acres along the Choptank River. Once known as “Hazelwood,” this historic Governor’s Mansion is one you don’t want to miss! Inside, you’ll find expansive formal and informal rooms flow seamlessly for entertaining and family living alike. This estate features refinished

  Christina Ginn Fathom Realty LLC

  24800 Pealiquor Rd, Denton, MD 21629
• 

  

  /50

  $575,000

  • 3 Beds
  • 2.5 Baths
  • 2,190 Sq Ft

  25749 Herring Ln, Denton, MD 21629

  Back on the market no fault of the seller. Welcome to your dream home! This beautifully maintained 3-bedroom, 2.5-bath rancher offers modern comfort and incredible outdoor amenities. Nestled on a spacious lot, just under 3 acres, this home boasts all-new stainless steel appliances, a newer HVAC system, and solar panels for energy efficiency bringing your electric bills down to $15-$50 a month!

  Justin Damadio Iron Valley Real Estate Ocean City

  25749 Herring Ln, Denton, MD 21629

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