Caroline County MD Homes for Sale

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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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  $286,490 New Construction

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

  125 Hobbs St, Greensboro, MD 21639

  Discover 125 Hobbs Street, a new home soon to be 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, two bathrooms, and a two-car driveway. 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

  D.R. Horton Builder

  125 Hobbs St, Greensboro, MD 21639
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  /15

  $450,000

  • 4 Beds
  • 2 Baths
  • 2,111 Sq Ft

  27329 Jenny Hye Ln, Marydel, MD 21649

  Situated on a 1.51 acre lot, backing to woods, this four Bedroom, 2 full bath home's interior has been completely renovated! Kitchen with eat -in area has been updated with new cabinetry, granite countertops & s/s appliances, Separate dining room for those wanting a more formalized area or can be used as a den, Living room with wood burning fireplace leads to expansive family room with access to

  Kathleen May Synergy Realty

  27329 Jenny Hye Ln, Marydel, MD 21649
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  /26

  $304,900

  • 3 Beds
  • 2 Baths
  • 1,104 Sq Ft

  1 Oakview Ct, Ridgely, MD 21660

  Well-maintained 3BR, 2BA home offering a functional layout with a cozy living room and an updated kitchen featuring stainless steel appliances. The primary bedroom includes a full bath, and the laundry/mudroom provides added practicality. Fresh paint throughout, plus a fenced yard, gazebo, and patio create inviting outdoor space. Recent improvements include solar panels (2018) and a new roof

  Peter Stark Benson & Mangold, LLC

  1 Oakview Ct, Ridgely, MD 21660
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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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  /11

  $3,700,000

  8019 Patten Rd, Denton, MD 21629

  Poultry farm features a total of 60.57 acres (40 acres tillable, 8.5 acres wooded, 1.5-acre retention pond) and a 40x72 shop that has garage parking and a separate space that could be finished for permanent living. Located approx. 5 miles from the DE line. Expired site evaluation-no septic on property.

  Tambra Reagan CALLAWAY FARNELL AND MOORE

  8019 Patten Rd, Denton, MD 21629
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  /50

  $642,900 Open Sat 12PM - 2PM

  • 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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  /111

  $989,000

  • 4 Beds
  • 3.5 Baths
  • 2,520 Sq Ft

  8416 Harmony Rd, Denton, MD 21629

  Discover a truly rare opportunity where lifestyle, income potential, and homeownership come together on this expansive 12.7-acre, two-parcel property zoned rural—offering unmatched flexibility and endless possibilities.Currently operating as a productive orchard, greenhouse operation, and microgreens business, this property is thoughtfully equipped for both personal enjoyment and

  Casey Neves The Parker Group

  8416 Harmony Rd, Denton, MD 21629
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  /57

  $495,000

  • 4 Beds
  • 2.5 Baths
  • 1,920 Sq Ft

  7837 Shore Dr, Preston, MD 21655

  Two Johns – Charming Home in a Sought-After Waterfront Community Nestled between Preston and Denton in the desirable Two Johns subdivision, this beautifully maintained 4-bedroom, 2.5-bath home offers a rare blend of comfort, style, and location. Just a few houses away from the public boat landing, residents enjoy easy water access for boating, kayaking, or fishing. Take in serene water views from

  Eddie Matthews Benson & Mangold, LLC

  7837 Shore Dr, Preston, MD 21655
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  /2

  $179,000 Coming Soon

  • 2 Beds
  • 2 Baths
  • 968 Sq Ft

  107 N School St Unit 3B, Greensboro, MD 21639

  Rare Opportunity ! Built 1922 as a school and converted into condo units. Many of the original elements make each building unique. With massive windows different architectural elements makes each unit distinctive. Open floor plan with updated appliances make this turn key for its next resident.. This unit has Two comfortable size bedrooms, two full baths, washer and dryer. There is an owner

  Kat Thompson Benson & Mangold, LLC.

  107 N School St Unit 3B, Greensboro, MD 21639
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  /23

  $1,100,000 Open Sat 12:30PM - 1:30PM

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

  6401 Laurel Grove Rd, Denton, MD 21629

  Nestled on an expansive 52.08-acre estate, this stunning ranch-style farm offers a harmonious blend of luxury and tranquility, perfect for those seeking an exclusive lifestyle in a serene rural setting. The property boasts a traditional architectural design, complemented by aluminum siding that enhances its timeless appeal. Step inside to discover a thoughtfully designed interior that exudes

  Michelle Anderson Coldwell Banker Premier - Rehoboth

  6401 Laurel Grove Rd, Denton, MD 21629
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  /23

  $1,100,000

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

  6401 Laurel Grove Rd, Denton, MD 21629

  Nestled on an expansive 52.08-acre estate, this stunning ranch-style farm offers a harmonious blend of luxury and tranquility, perfect for those seeking an exclusive lifestyle in a serene rural setting. The property boasts a traditional architectural design, complemented by aluminum siding that enhances its timeless appeal. Step inside to discover a thoughtfully designed interior that exudes

  Michelle Anderson Coldwell Banker Premier - Rehoboth

  6401 Laurel Grove Rd, Denton, MD 21629
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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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  /69

  $740,000

  • 5 Beds
  • 4 Baths
  • 5,286 Sq Ft

  24764 Pealiquor Rd, Denton, MD 21629

  Welcome to Timeless Elegance Meets Modern Comfort. Step inside this stunning Cape Cod residence and immediately feel at home. A gracious foyer framed by classic columns invites you into a luminous interior that effortlessly blends traditional charm with modern open‐concept living. To your right, a versatile flex room offers the perfect space for a home office, formal dining, or private study.

  Dustin Parker The Parker Group

  24764 Pealiquor Rd, Denton, MD 21629
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  /10

  $184,900

  • 3 Beds
  • 1 Bath
  • 716 Sq Ft

  406 Lincoln St, Denton, MD 21629

  This adorable home is ready and waiting for you to move in and make it your own. The home was renovated just 2 years ago. Updated items include windows, HVAC, cabinets, flooring, carpet, plumbing, electric, and roof. Enjoy being close to local restaurants, shops, parks, schools, boat ramps, and MD/DE beaches. This property was most recently used as an income-producing rental property. Property is

  Lisa Secrist Chesapeake Real Estate Associates, LLC

  406 Lincoln St, Denton, MD 21629
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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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  /23

  $200,000

  • 3 Beds
  • 2.5 Baths
  • 1,860 Sq Ft

  1507 Blue Heron Dr, Denton, MD 21629

  3-Story Townhome Ready for Its New Owners!Home offers 3 bedrooms and 2.5 baths with a functional layout and comfortable living spaces. The spacious first floor features an open living area and convenient half bath for guests.The second floor includes two bedrooms, a full bath, and laundry area, providing everyday convenience. The third-floor primary suite offers a private retreat with a

  KL Harris Keller Williams Select Realtors of Cambridge

  1507 Blue Heron Dr, Denton, MD 21629
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  /23

  $290,000

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  12 N Maple Ave, Ridgely, MD 21660

  Seller has to find home of choice. Welcome home to this charming 2-bedroom, 1-bath gem nestled in a quiet, established neighborhood. Perfect for first-time buyers, downsizers, or anyone looking for comfortable, low-maintenance living, this home offers both warmth and functionality. Step inside to find beautiful new wood flooring flowing through the living room, kitchen, and hallway, creating a

  Wes Russum Coldwell Banker Chesapeake Real Estate Company

  12 N Maple Ave, Ridgely, MD 21660
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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

  $282,990 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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  /24

  $239,900

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft

  329 Maple Ave, Federalsburg, MD 21632

  Charming Rancher with Beautiful Upgrades! This well-maintained 3-bedroom, 2-bath home features beautiful hardwood floors, a spacious living room, and an inviting kitchen designed for both everyday living and entertaining. The kitchen boasts quartz countertops and ample workspace, perfect for cooking and gathering.Enjoy the convenience of a separate laundry room plus an additional storage room

  Mary Mabry Keller Williams Select Realtors of Cambridge

  329 Maple Ave, Federalsburg, MD 21632
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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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  /31

  $269,900

  • 3 Beds
  • 1.5 Baths
  • 1,155 Sq Ft

  502 W Sunset Ave, Greensboro, MD 21639

  Renovated & Move-In Ready with Detached 2-Car Garage! Welcome to this beautifully updated 3-bedroom, 1.5-bath home where modern style meets everyday comfort. From the moment you step inside, you’ll notice the fresh, clean feel created by brand-new LVP flooring, recessed lighting, fresh paint throughout, and a completely renovated kitchen and bathroom designed with today’s buyer in mind.The

  Pamela Geib Long & Foster Real Estate, Inc.

  502 W Sunset Ave, Greensboro, MD 21639
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  /28

  $179,900

  • 2 Beds
  • 1.5 Baths
  • 1,196 Sq Ft

  341 Academy Ave, Denton, MD 21629

  Welcome to Denton! Small town living with all the amenities nearby! Cute townhouse with two bedrooms, one and a half baths with washer/dryer in unit. Nice rear desk with new Trex decking, private parking in the rear. Low maintenance and No HOA. Walk into town for coffee or a meal then walk down to the water along the Choptank River. Boat ramp and kayak/paddle board launch minutes away. Super

  Jason Dey Kevin Dey Realty

  341 Academy Ave, Denton, MD 21629
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  /74

  $525,000

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

  22005 Main St, Hillsboro, MD 21641

  PLEASE NOTE that the Owner has listened to the current market, Price has been reduced to $525,000. It is a property of beautifully preserved quality on 3⁄4 of an acre in an urban setting. Most unusual! When compared to equivalent historic properties it is now very competitively priced! This fine, brick dwelling originating from the18th c. is situated in Hillsboro on Maryland's peaceful Eastern

  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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  /36

  $249,900

  • 3 Beds
  • 3 Baths
  • 1,678 Sq Ft

  102 S Academy St, Greensboro, MD 21639

  Classic Charm Meets In-Town Living. Enjoy the luxury of space on this generous .34-acre lot, featuring a 3-bedroom home designed for both quiet mornings on the front porch and lively backyard BBQs. Inside, flow seamlessly from the bright & airy living room to the dining area and kitchen. With three full baths, a dedicated laundry room, and a storage-ready basement, the layout is as functional as

  Karen Clark Clark & Co Realty, LLC

  102 S Academy St, Greensboro, MD 21639
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  /36

  $299,900

  • 3 Beds
  • 1.5 Baths
  • 1,791 Sq Ft

  309 N Main St, Greensboro, MD 21639

  This exquisite Colonial-style home, thoughtfully renovated in 2019, seamlessly blends classic charm with modern luxury. Spanning 1,791 square feet, this residence offers a warm and inviting atmosphere, perfect for creating lasting memories. Step inside to discover a beautifully designed interior featuring engineered luxury vinyl plank flooring that exudes elegance and durability. The heart of the

  Eddie Matthews Benson & Mangold, LLC

  309 N Main St, Greensboro, MD 21639
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  /29

  $434,000

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

  23116 Gilpin Point Rd, Preston, MD 21655

  A perfectly situated, water-oriented, turnkey, rancher with a piece of country is ready for your enjoyment. Produce your own vegetables, flowers or the like in the already established rear garden beds, collect your peaches, pears and other fruits from fruit bearing trees. Start your plants early in an enclosed greenhouse/produce stand. A second greenhouse area is framed and ready for a canopy.

  Edward Cartwright Benson & Mangold, LLC

  23116 Gilpin Point Rd, Preston, MD 21655
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  /37

  $609,900

  • 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

  $309,000

  • 4 Beds
  • 3.5 Baths
  • 2,640 Sq Ft

  1907 Blue Heron Dr, Denton, MD 21629

  Highly sought after large townhome in the desirable community of Mallard Landing in Denton, featuring almost double the square footage, and a rear deck off of the kitchen. Multi-generational living has a full bedroom and bath, as well as a large family room on the main floor. A few easy steps to the second floor brings you to a beautiful open kitchen, dining, and living room. The third floor

  Juliet Wells Coldwell Banker Chesapeake Real Estate Company

  1907 Blue Heron Dr, Denton, MD 21629
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  /12

  $1,300,000

  • Land
  • 92.9 Acres
  • $13,994 per Acre

  0 Liberty Rd, Federalsburg, MD 21632

  90± deeded acres located east of Federalsburg off Liberty Road. The farm is primarily comprised of tillable land with approximately 36± acres under center pivot irrigation. Soils consist primarily of Woodstown, Klej-Galloway complex, and Fallsington sandy loam soils, which are commonly used for grain and row crop production in the area. The property offers approximately one half mile of road

  Benjamin Alder The Land Group

  0 Liberty Rd, Federalsburg, MD 21632
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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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  /16

  $245,000

  • 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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  /89

  $2,750,000

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

  28219 Bridgeville Rd, Federalsburg, MD 21632

  Welcome to a rare opportunity to own a premier 105+/- acre agricultural estate combining modern comfort, income-producing farmland, and outstanding infrastructure. Ideally situated in a peaceful rural setting, this remarkable property features approximately 70± acres of fully irrigated, tillable land—perfect for high-yield row crops or specialty farming. At the heart of the farm sits a stunning

  Jim Corson Benson & Mangold, LLC

  28219 Bridgeville Rd, Federalsburg, MD 21632
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  /53

  $225,000

  • 3 Beds
  • 1.5 Baths
  • 2,817 Sq Ft

  22060 Main St, Hillsboro, MD 21641

  Needs Work. sold as is - large home in need of updating/TLC - 2-story 3 car garage

  Keith Brooks Thurston Wyatt Real Estate, LLC

  22060 Main St, Hillsboro, MD 21641
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  /40

  $235,000

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

  212 Main St, Preston, MD 21655

  Welcome to this spacious and beautifully maintained property nestled in the peaceful town of Preston. The main residence features 5 generously sized bedrooms and 3 full bathrooms, offering plenty of space for comfortable family living, guests, or multi-generational arrangements. At the heart of the home, you’ll find a large eat-in kitchen, perfect for gathering with family, hosting friends, or

  Ross Muir EXP Realty, LLC

  212 Main St, Preston, MD 21655
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  /5

  $100,000 Pre-Foreclosure

  • 3 Beds
  • 1 Bath
  • 1,036 Sq Ft

  13963 Oakland Rd, Ridgely, MD 21660

  Foreclosure Auction Ends April 07, 2026 at 11:10 AM EST. Discover this inviting 3-bedroom, 1-bathroom single-family home, offering a great opportunity in the desirable Ridgely area. Sold As-is. Explore more details and submit your bid through Federa Home App.

  Jamie Boone Federa

  

  13963 Oakland Rd, Ridgely, MD 21660

Showing Results 81 - 120, Page 3 of 4