Caroline County MD Homes for Sale

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  /14

  $140,000

  • 2 Beds
  • 2 Baths
  • 640 Sq Ft

  26471 Three Bridges Rd, Federalsburg, MD 21632

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

  LEE MARLAND Keller Williams Realty

  26471 Three Bridges Rd, Federalsburg, MD 21632
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  /51

  $639,000

  • 4 Beds
  • 4 Baths
  • 3,484 Sq Ft

  24324 Asbury Dr, Denton, MD 21629

  Lovely grand colonial with covered front porch located on almost 4 acres. The first floor offers a huge primary suite with walk in closet and bath with soaking tub, dual headed shower and double vanity.Dining room has gleaming hardwood floors with enough space to seat 20 people, lovely overhead chandelier and warming propane fireplace . Kitchen has all stainless appliances, plenty of

  Bonnie Johnson Keller Williams Realty

  24324 Asbury Dr, Denton, MD 21629
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  /43

  $245,000

  • 3 Beds
  • 2 Baths
  • 1,684 Sq Ft

  207 Bloomingdale Ave, Federalsburg, MD 21632

  Discover this inviting 3-bedroom, 2-bath home on a 0.27-acre lot in the heart of Federalsburg. Enter to a spacious living room filled with natural light and a cozy fireplace, perfect for relaxing or entertaining. Adjacent, the family room features stunning wood-paneled walls, built-in shelving, a second fireplace, and access to both the outdoors and the kitchen and dining areas, creating a

  Dustin Parker The Parker Group

  207 Bloomingdale Ave, Federalsburg, MD 21632
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  /40

  $460,000

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

  320 N Main St, Greensboro, MD 21639

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

  Karen Clark Clark & Co Realty, LLC

  320 N Main St, Greensboro, MD 21639
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  /91

  $699,000

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

  4 S 1st St, Denton, MD 21629

  Outstanding Business Opportunity! Rare Find with-in Downtown Denton! Property would make an excellent Restaurant, Bar, great Venue , or a Large Victorian Home! Features include but not limited to Residential, Commerical or Mixed Use. Large Wrap around Porch for entertaining, Patio with plenty of room for seating with Firepit. Park like setting with Open Space and Large Pond! Town ERU's are

  Kathleen Brenton Brenton Realty Group

  4 S 1st St, Denton, MD 21629
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  /3

  $135,000

  • Land
  • 0.69 Acre
  • $195,652 per Acre

  1005 Market St, Denton, MD 21629

  A Rare Opportunity to Purchase a General Commercial Lot located in Denton off the High Visibility Corners of Market & Gay St. A Multitude of permissible uses. Water and Sewer hook ups are available for additional fee. There are not any structures on this cleared .69 ac lot. A wonderful Opportunity for the Entrepreneur with a Vision....Hurry to snag this one...

  Barbara Beaudet Brenton Realty Group

  1005 Market St, Denton, MD 21629
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  /10

  $42,999

  • Land
  • 0.24 Acre
  • $179,162 per Acre

  0 Brooklyn Ave, Federalsburg, MD 21632

  Taylor McCartney VRA Realty

  0 Brooklyn Ave, Federalsburg, MD 21632
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  /10

  $620,000

  • Studio
  • 3,600 Sq Ft

  310 Main St, Marydel, MD 21649

  Great Apartment Building investment opportunity, updated, and ready to go! The building includes three 2-bedroom, 1-bath units and one 3-bedroom, 1-bath unit — all with private entrances and separately metered utilities. A furnished office space adds additional potential for on-site management or rental income.Recent upgrades include: New well (less than a year old) with a 20-year warranty,

  

  Sharon Daugherty

  Keller Williams Realty Delmarva

  (410) 881-8824

  310 Main St, Marydel, MD 21649
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  /34

  $245,000

  • 3 Beds
  • 2 Baths
  • 1,840 Sq Ft

  158 Wright St, Preston, MD 21655

  Step back in time with this charming 3-bedroom, 2-bathroom home built in 1890, located in the heart of Preston. Full of character and original details, this home offers a unique opportunity to restore and customize a piece of local history. The inviting living room features a cozy fireplace, perfect for relaxing evenings. A large laundry room and a separate den/office provide flexibility and

  Wes Russum Coldwell Banker Chesapeake Real Estate Company

  158 Wright St, Preston, MD 21655
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  /8

  $355,000

  • 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

  Glory Bee Costa Keller Williams Select Realtors of Easton

  27279 Jenny Hye Ln, Marydel, MD 21649
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  /71

  $445,000

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

  25699 Auction Rd, Federalsburg, MD 21632

  ***BUYER WALKED AWAY!!****Mortgage savings may be available for buyers of this home. Opportunity to purchase a working farm with remodeled residence - from 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

  Barbara McCaffrey Redfin Corp

  25699 Auction Rd, Federalsburg, MD 21632
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  /47

  $625,000

  • 3 Beds
  • 2 Baths
  • 1,616 Sq Ft

  300 S 1st St, Denton, MD 21629

  Peaceful Living on the Choptank River!!! One level Living! Offering 3 Bed and 1.5 Bath. Home features an open Floor Plan with Large Living Room w/ Gas Burning Stove., Spacious Kitchen with Tons of Storage, Breakfast Bar, and plenty of space for your Table and Chairs! Primary Bedroom facing the Water with Great Waterfront Views. Home also features a paved driveway with 2 door garage and a full

  Kathleen Brenton Brenton Realty Group

  300 S 1st St, Denton, MD 21629
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  /20

  $189,900

  • 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

  Bonnie Duley Long & Foster Real Estate, Inc.

  21948 Main St, Hillsboro, MD 21641
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  /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
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  /55

  $429,900

  • 5 Beds
  • 2 Baths
  • 4,060 Sq Ft

  8 W Liberty St, Ridgely, MD 21660

  Welcome to this beautiful updated Custom Built Brick 5-bedroom, 2-bath home nestled on a generous double corner lot in the quaint town of Ridgely. Combining classic charm with modern updates. This property offers comfort and convenience—perfect for growing families or those who love to entertain. Property hightlights include: Updated kitchen featuring brand-new stainless steel appliances, new

  Barbara Blosser Long & Foster Real Estate, Inc.

  8 W Liberty St, Ridgely, MD 21660
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  /17

  $380,000 New Construction

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

  106 Lednum Ave, Preston, MD 21655

  New construction in Preston, MD offering 3 bedrooms and 2 full baths across 1,400 square feet. This home features an open layout with vaulted ceilings, LVP flooring in the main living areas, and carpeted bedrooms. The kitchen is equipped with stainless steel appliances and granite countertops. The primary suite includes a stand-up shower, while the guest bath offers a tub/shower combo. An

  Eric Haro The Parker Group

  106 Lednum Ave, Preston, MD 21655
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  /5

  $140,000

  • Land
  • 3.75 Acres
  • $37,333 per Acre

  0 Burnt Mill Rd Unit MDCM2006056, Ridgely, MD 21660

  Discover the ideal blend of tranquil nature and prime location! 3.75 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 MDCM2006056, Ridgely, MD 21660
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  /89

  $2,750,000

  • 4 Beds
  • 4.5 Baths
  • 6,520 Sq Ft

  28219 Bridgeville Rd, Federalsburg, MD 21632

  First time on the market! Discover a rare opportunity to own a 105± acre estate on Maryland’s beautiful Eastern Shore, Close to tax free shopping and the beaches. Designed by renowned California architect David Watson, the exterior of this home is one of the all-time most downloaded photos on the popular homebuilding and design website, Houzz. This one-of-a-kind property combines luxury living,

  Jim Corson Benson & Mangold, LLC

  28219 Bridgeville Rd, Federalsburg, MD 21632
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  /2

  $129,000

  • 6 Beds
  • 2 Baths
  • 2,400 Sq Ft

  321 S Main St, Federalsburg, MD 21632

  tenant occupied duplex rented for 1600/ month. agent is owner

  Bo Claggett Coldwell Banker Realty

  321 S Main St, Federalsburg, MD 21632
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  /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
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  /4

  $92,000

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

  162 Main St, Preston, MD 21655

  Anne Schmidt Long & Foster Real Estate, Inc.

  162 Main St, Preston, MD 21655
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  /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
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  /80

  $749,900

  • 6 Beds
  • 4.5 Baths
  • 5,000 Sq Ft

  15184 Jarrell Rd, Goldsboro, MD 21636

  BACK ON THE MARKET.....,Buyer financing fell through. All inspections (Home, Well and Septic) have been completed and any and all issues addressed. OWNER SAY: "COME ON DOWN, LET'S MAKE A DEAL" The Possibilities are endless on this, serene 12.12 acres just ready and waiting for you to turn it into your dream. The Property includes a Beautiful 5000+ square foot home and a Massive Detached 60X42

  Leslie Fulford Mann & Sons, Inc.

  15184 Jarrell Rd, Goldsboro, MD 21636
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  /24

  $286,990 New Construction

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

  SULLIVAN Plan at Kinnamon Meadows, Greensboro, MD 21639

  The Sullivan is a charming 1,219-square-foot, cottage-style ranch home featuring three bedrooms, two bathrooms, and a one-car garage. Just off the foyer, two spacious guest bedrooms and a shared full bathroom offer comfort and privacy for family or visitors. The open-concept kitchen boasts stainless steel appliances, modern cabinetry, and an optional island with seating that is perfect for casual

  D.R. Horton Builder

  103 Park Ave Unit 36203275, Greensboro, MD 21639
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  /22

  $266,990 New Construction

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

  PERRY Plan at Kinnamon Meadows, Greensboro, MD 21639

  The Perry, a 1,059 square foot open concept cottage-style ranch home, offers two bedrooms and two bathrooms. A welcoming front porch leads you into the spacious living room that seamlessly flows into the kitchen, creating a perfect space for entertaining guests or enjoying family time. The well-equipped kitchen is complete with modern cabinetry, stainless steel appliances, a spacious peninsula

  D.R. Horton Builder

  103 Park Ave Unit 36203273, Greensboro, MD 21639
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  /3

  $276,990 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
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  /2

  $291,990 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
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  /23

  $299,000

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  505 Maryland Ave, Ridgely, MD 21660

  Welcome to this beautifully updated 3-bedroom, 2-bath rancher located in the charming town of Ridgely, Maryland. Renovated just about two years ago, this home has been lovingly maintained and offers stylish, move-in-ready living with modern finishes throughout. The open-concept kitchen features granite countertops, a spacious island perfect for entertaining, soft-close cabinetry, and

  Kaitlyn Collins Benson & Mangold, LLC

  505 Maryland Ave, Ridgely, MD 21660
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  /4

  $24,500

  • 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
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  /25

  $217,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,365 Sq Ft

  Jefferson Plan at Riverwalk Terrace, Federalsburg, MD 21632

  The Jefferson is an open-concept 1,365 square foot two-story townhome with three bedrooms and two and a half bathrooms. The first floor is spacious with a large, thoughtfully designed kitchen with ample cabinet space, stainless steel appliances, a storage closet, and a peninsula island with space for seating. The kitchen is open to the living and dining area providing your ideal entertainment

  D.R. Horton Builder

  100 Riverwalk Terrace Unit 36203297, Federalsburg, MD 21632
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  /55

  $699,900

  • 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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  /4

  $345,000

  • Studio
  • 2,260 Sq Ft

  517 W Sunset Ave, Greensboro, MD 21639

  Three unit apartment building. Two 1bedroom apartments, one 2 bedroom. Fully leased with positive income to support expense and debt service

  Randy Staats Benson & Mangold, LLC

  517 W Sunset Ave, Greensboro, MD 21639
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  /24

  $153,000

  • Land
  • 3 Acres
  • $51,000 per Acre

  0 Asbury Dr, Denton, MD 21629

  Discover your ideal homesite in the scenic Asbury on the Choptank community, where peaceful living meets convenient access. This expansive 3-acre lot is perc approved for a three-bedroom septic system. Within this sought-after community, residents enjoy well-maintained roads, a private nature trail, and exclusive access to a community deepwater dock on the Choptank River. Ideal for boating

  Coard Benson Benson & Mangold, LLC

  0 Asbury Dr, Denton, MD 21629
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  /14

  $149,900

  • Land
  • 10.39 Acres
  • $14,427 per Acre

  PARCEL 91 Cool Spring Rd, Marydel, MD 21649

  Ready for you to build your new home! This beautiful lot is already perc tested for a 3-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 complete. So come see and come buy and

  Bonnie Duley Long & Foster Real Estate, Inc.

  PARCEL 91 Cool Spring Rd, Marydel, MD 21649
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  /35

  $599,000

  • 4 Beds
  • 2 Baths
  • 1,771 Sq Ft

  12459 Kibler Rd, Greensboro, MD 21639

  Outstanding small farm property on quiet country road! This spacious home features 3-4 bedrooms and two baths, kitchen with new stainless steel appliances, breakfast bar and dining area. The large living room with wood floors over look the expansive front yard and opens to the front porch where you can enjoy your morning coffee. In the rear of the home there is a large family room that offers a

  Marcia Rostien Long & Foster Real Estate, Inc.

  12459 Kibler Rd, Greensboro, MD 21639
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  /28

  $339,000

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

  208 Oriole Ave, Ridgely, MD 21660

  Come see this Beautiful well maintained Ranch home in the heart of Ridgely. The house is a block away from the local park. The house has had many upgrades including an addition in 2020. New siding in 2020. New deck after 2020. New windows in 2017. There are solar panels on the roof. Spacious back yard with a patio. Many other upgrades to come and see.

  Rachel Penska Long & Foster Real Estate, Inc.

  208 Oriole Ave, Ridgely, MD 21660
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  /22

  $510,000

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

  0 Dover Bridge Rd Unit MDCM2005586, Preston, MD 21655

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

  Coard Benson Benson & Mangold, LLC

  0 Dover Bridge Rd Unit MDCM2005586, Preston, MD 21655
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  /10

  $157,499

  • Land
  • 1.01 Acres
  • $155,940 per Acre

  707 W Sunset Ave, Greensboro, MD 21639

  Several individual parcels on Sunset, Cosden and Harold Streets. One parcel has a large 50' x 70' Morton style building, town water and sewer are available. The offering does seem to have some ownership of another parcel consisting of Cosden St. Any interested buyer should perform their own suitable level of due diligence.

  BRIAN MORRIS The Land Group

  707 W Sunset Ave, Greensboro, MD 21639
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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

  (443) 232-1392

  23296 Wilder Way, Denton, MD 21629
• 

  

  /74

  $545,000

  • 3 Beds
  • 3 Baths
  • 3,088 Sq Ft

  22005 Main St, Hillsboro, MD 21641

  This fine, brick dwelling originating from the18th c. is situated in Hillsboro on Maryland's peaceful Eastern Shore. Hillsboro, nestled along the Tuckahoe River, conveniently located to all that is important to the Eastern Shore's sought-after lifestyle. The WILLIAM SMITH HOUSE, built in 1794, exemplifies the world of a successful Grain Merchant living in an important hub for grain and tobacco.

  Nancy McGuire Maryland Heritage Properties

  22005 Main St, Hillsboro, MD 21641

Showing Results 81 - 120, Page 3 of 4