Caroline County MD Homes for Sale

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  /56

  $497,000

  • 3 Beds
  • 2 Baths
  • 1,904 Sq Ft

  20915 Dover Bridge Rd, Preston, MD 21655

  Set on 8.6 private, fully fenced acres just across the Dover Bridge, this Eastern Shore property offers endless possibilities with scenic surroundings, expansive land, and close proximity to the Choptank River, just minutes from Easton.The single-level home features three bedrooms and two full bathrooms, a country kitchen, and an open-concept layout highlighted by a massive brick fireplace

  Alex Martinez The Agency DC

  20915 Dover Bridge Rd, Preston, MD 21655
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  /2

  $65,000

  • Land
  • 1.75 Acres
  • $37,143 per Acre

  307 Buena Vista Ave, Federalsburg, MD 21632

  Build Your Dream in Federalsburg!Rare opportunity to own a 1.75-acre buildable lot located within the town limits of Federalsburg. This spacious parcel offers the perfect blend of small-town charm and room to breathe—plenty of space for your custom home, garage, and outdoor living without feeling boxed in. Conveniently located near local amenities, schools, and major routes, yet tucked away

  Heather Brummell Keller Williams Realty

  307 Buena Vista Ave, Federalsburg, MD 21632
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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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  /42

  $469,900

  • 4 Beds
  • 2.5 Baths
  • 2,550 Sq Ft

  24749 Woods Dr, Denton, MD 21629

  Beautifully maintained 4 bedroom, 2.5 bath Colonial set on a spacious lot just minutes from Denton and the newly opened Caroline Country Club. This inviting home features a comfortable, flowing layout featuring a gas fireplace, perfect for relaxing evenings or gatherings. The kitchen is conveniently located right off the main living area. The space showcases granite counter tops, stainless steel

  Peter Stark Benson & Mangold, LLC

  24749 Woods Dr, 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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  /38

  $214,900

  • 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 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 floor

  Georgi Chauvin Benson & Mangold, LLC

  318 Carter Ave, 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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  /4

  $155,000

  • 1 Bed
  • 1 Bath
  • 512 Sq Ft

  26355 Marydel Rd, Marydel, MD 21649

  House is of little to no value, existing well and septic. This house includes an additional parcel of 7 acres, tax id, 0601012428 for a total of 7.27 acres. Property being SOLD AS IS.

  George Thompson Long & Foster Real Estate, Inc.

  26355 Marydel Rd, Marydel, MD 21649
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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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  /2

  $249,900

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  5940 Noble Rd, Federalsburg, MD 21632

  Welcome to peaceful rural living just minutes from town conveniences in Federalsburg, MD. This well-situated single-story ranch home offers functional and accessible living across one level, perfectly suited for first-time buyers, downsizers, or those seeking country comfort with ample outdoor space. You'll have nearly 3 acres of land — great for gardening, recreation, or possbly a future

  Holly Anderson Long & Foster Real Estate, Inc.

  5940 Noble Rd, Federalsburg, MD 21632
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  /2

  $32,500

  • Land
  • 0.69 Acre
  • $47,101 per Acre

  0 Douglas & Lincoln St Unit MDCM2006716, Ridgely, MD 21660

  Just next to the quaint town of Ridgely, this .69 acre lot also comes with a bonus lot highlighted in photos. Buy and hold as an investment or see if you can perc.

  Michael Rosendale Rosendale Realty

  0 Douglas & Lincoln St Unit MDCM2006716, Ridgely, MD 21660
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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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  /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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  /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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  /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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  /60

  $699,000

  • 3 Beds
  • 2 Baths

  28402 Liden School Rd, Denton, MD 21629

  Private serene living at its finest! This property has it all -- gorgeous rancher with 3 BR and 2 full baths; large 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 primary bedroom; so much to mention here that you really must come see for yourself -- fresh air, peace and quiet, birds singing,

  Bonnie Duley Long & Foster Real Estate, Inc.

  28402 Liden School Rd, Denton, MD 21629
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  /54

  $549,000

  • 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
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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 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 completed. So come see and come buy and be

  Bonnie Duley Long & Foster Real Estate, Inc.

  PARCEL 91 Cool Spring Rd, Marydel, MD 21649
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  /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
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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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  /37

  $609,900 Open Sun 2PM - 4PM

  • 4 Beds
  • 5 Baths
  • 3,491 Sq Ft

  24712 Tribbett Cir, Ridgely, MD 21660

  Welcome to 24712 Tribbett Circle — a beautifully appointed 2016-built home set on 2.43 pristine acres in one of Ridgely’s most desirable neighborhoods. This luxurious 4-bedroom, 4-bathroom property seamlessly blends timeless style with modern comfort, offering an exceptional living experience both inside and out. The main level is adorned with rich bamboo flooring, creating a warm and

  Chris Warren Long & Foster Real Estate, Inc.

  24712 Tribbett Cir, Ridgely, MD 21660
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  /2

  $23,000

  • Land
  • 0.14 Acre
  • $164,286 per Acre

  12115 Lincoln St, Ridgely, MD 21660

  Lot in the town of Ridgely, check with the town/county about putting a new house on this lot. There was previously a house on this lot.

  Pamela Geib Long & Foster Real Estate, Inc.

  12115 Lincoln St, Ridgely, MD 21660
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  /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
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  /22

  $359,900

  • 3 Beds
  • 2 Baths
  • 1,753 Sq Ft

  311 Kerr Ave, Denton, MD 21629

  Discover this beautifully updated 3-bedroom, 2-bath corner lot rancher in Denton, Maryland, offering style, comfort, and unbeatable convenience! This single-story gem features gorgeous bamboo flooring throughout, creating a warm and modern ambiance. The traditional floor plan gives the living room area with wood burning fireplace a perfect cozy space for relaxing. Step into the Eat in Kitchen

  Justin Damadio Iron Valley Real Estate Ocean City

  311 Kerr Ave, 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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  /19

  $50,000

  • Land
  • 0.37 Acre
  • $135,135 per Acre

  2 N Main St, Greensboro, MD 21639

  Cleared and ready for your vision! This 1/3+ acre in-town parcel offers the perfect canvas for your new build. Buyer to perform all due diligence with the Town regarding development requirements, including costs for water and sewer allocation.

  Karen Clark Clark & Co Realty, LLC

  2 N Main St, Greensboro, MD 21639
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  /9

  $159,000

  • 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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  /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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  /9

  $250,000

  • 3 Beds
  • 2.5 Baths
  • 1,693 Sq Ft

  1204 Blue Heron Dr, Denton, MD 21629

  Come on in to explore this beautifully maintained 3-level home offering the perfect blend of modern convenince and comfortable living. This beauty features 3 spacious bedrooms and 2.5 baths, with an open floor plan that creates an inviting flow throughout the main living areas. The home has been thoughtfully updated with fresh paint, new appliances and more to ensure it's move-in ready for you.

  Carolyn A. Page Shore Results Realty

  1204 Blue Heron Dr, Denton, MD 21629
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  /51

  $325,000

  • 4 Beds
  • 2 Baths
  • 1,326 Sq Ft

  1203 Tuckahoe Ct, Denton, MD 21629

  Charming 4 bedroom, 2 bath cottage tucked away on a quiet cul-de-sac just minutes from downtown Denton. The first floor features a welcoming living room with LVP flooring, kitchen with updated appliances, two bedrooms, and a full bath. Upstairs, you’ll find two additional bedrooms and a second full bath, offering flexible living space. Outside enjoy a large, fenced-in backyard with a deck and

  Alicia Gannon Dulin Benson & Mangold, LLC

  1203 Tuckahoe Ct, Denton, MD 21629
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  /24

  $199,000

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  218 E Sunset Ave, Greensboro, MD 21639

  This charming 3-bedroom, 1-bath home sits just across the street from the beautiful Choptank River, offering water views right from your doorstep. Enjoy the benefits of solar panels for lower energy costs.The property also includes a spacious 24’ x 28’ detached garage—perfect for vehicles, a workshop, or extra storage. Whether you’re looking for your first home or looking to downsize this

  Stevie Brummell Keller Williams Realty

  218 E Sunset Ave, Greensboro, MD 21639
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  /7

  $145,000

  • 2 Beds
  • 1 Bath
  • 504 Sq Ft

  305 Maple Ave, Ridgely, MD 21660

  This cozy cottage, situated on a quiet alley, would be perfect for an individual or a young couple. Enjoy your morning coffee on the screened porch. Fenced backyard with a garden shed.

  Andrew Beaven Wright Real Estate

  305 Maple Ave, Ridgely, MD 21660
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  /51

  $619,000

  • 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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  /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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  /56

  $280,000

  • 5 Beds
  • 3 Baths
  • 2,122 Sq Ft

  212 Main St, Preston, MD 21655

  ***Unique Opportunity***Welcome to this spacious and well-cared-for property located in the peaceful town of Preston. The main home offers 5 generously sized bedrooms and 3 full bathrooms, providing ample space for comfortable family living or multi-generational needs. A large eat-in kitchen serves as the heart of the home, perfect for everyday meals or entertaining guests. This property

  Ross Muir EXP Realty, LLC

  212 Main St, Preston, MD 21655
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  /41

  $389,000

  • 4 Beds
  • 2.5 Baths
  • 2,138 Sq Ft

  1111 Trice Meadows Cir, Denton, MD 21629

  Discover your dream home in the highly sought-after Trice Meadows community! This delightful 4-bedroom, 2-bathroom detached single-family home perfectly combines comfort, style, and modern convenience. Its open and inviting floor plan is designed for both day-to-day living and entertaining, making it an ideal choice for families and social gatherings alike. Experience the seamless flow from the

  LaTanya Drayton United Real Estate Premier

  1111 Trice Meadows Cir, Denton, MD 21629
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  /53

  $234,000

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

  1412 Blue Heron Dr, Denton, MD 21629

  Total Re-Hab END UNIT !!! Almost New Everything.! Homes features 3 Bedrooms 2.5 Baths. Open floor plan with All new Kitchen Cabinets, Countertops& Appliances! New Luxury Vinyl Flooring and completely painted thru-out Entire Home. All Three Bathrooms have been updated including Tile Showers, New Vanities, and Fixtures. Community offers, Pool, Community Center, Playgrounds, Yard Maintenance, Boat &

  Kathleen Brenton Brenton Realty Group

  1412 Blue Heron Dr, Denton, MD 21629
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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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  /26

  $499,000

  • 4 Beds
  • 1.5 Baths
  • 2,320 Sq Ft

  11289 Gregg Rd, Denton, MD 21629

  Rare opportunity to purchase 19.1 acres with 2 dwellings, included property identified as 11285 Gregg Rd. Endless options to either rent one or have an in-law suite. It is said to have three septic systems, three electric services all on one property. Then main house which has the basement is in need of some remodeling, has 4 bedrooms and 1.1/4 baths, the remodling process has been started. The

  Kat Thompson Benson & Mangold, LLC.

  11289 Gregg Rd, Denton, MD 21629
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  /99

  $1,099,000

  • 6 Beds
  • 3.5 Baths
  • 3,704 Sq Ft

  13539 Hokum Dr, Greensboro, MD 21639

  A Private Eastern Shore Compound Designed for Living, Relaxing & Entertaining!Welcome to 13539 Hokum Drive, a rare Eastern Shore retreat offering privacy, amenities, and “room to breathe” on a gorgeous, partially wooded landscape. This isn’t just a home — it’s a full lifestyle setting, complete with multiple outbuildings, an in-ground pool, wooded trails, and incredible outdoor living spaces,

  Vincent Payne Realty Navigator

  13539 Hokum Dr, Greensboro, MD 21639

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