Caroline County MD Homes for Sale

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  /54

  $595,000

  • 4 Beds
  • 2.5 Baths
  • 3,168 Sq Ft

  24766 Tribbett Cir, Ridgely, MD 21660

  Why wait months to build when you can start enjoying this meticulously built, and finely crafted contemporary farmhouse home right now? Situated on an .85 acre lot in the established community of Ashworth, this 2023 built, 3,168 square foot, 4 bedroom, 2.5 bath home contemporary farmhouse-style home blends rustic charm with contemporary elegance. The exterior features classic white siding,

  Barbara McCaffrey Redfin Corp

  24766 Tribbett Cir, Ridgely, MD 21660
• 

  

  

  /22

  $389,900

  • 3 Beds
  • 2 Baths
  • 1,746 Sq Ft

  25432 Piney Branch Ln, Denton, MD 21629

  Beautiful country rancher sitting on private 1.16 +- acre lot with mature landscaping. The property features 3 bedrooms, 2 bathrooms, large kitchen, family room, and attached 2 car garage. A bright screened in porch off the back of the home leads to a spacious yard and additional storage shed. Single level with modern amenities, just minutes to downtown Denton shopping and restaurants!

  Brian Gearhart Benson & Mangold, LLC

  25432 Piney Branch Ln, Denton, MD 21629
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  /102

  $1,450,000

  • 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

  23296 Wilder Way, Denton, MD 21629
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  /144

  $1,449,000

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

  24512 Marblehead Rd, Ridgely, MD 21660

  This 99-acre wooded farm offers a well-rounded mix of equestrian, hunting, and homesteading features. Lovely 2 bedroom, 3 bath home, built in 2004, includes vaulted ceilings, a brick hearth propane fireplace with remote, hardwood flooring, and a fully conditioned crawlspace. A wrap-around front porch overlooks the horse pasture and garden, and the rear enclosed screen porch opens to a large brick

  Mike Arajakis

  24512 Marblehead Rd, Ridgely, MD 21660
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  /80

  $749,900

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

  15184 Jarrell Rd, Goldsboro, MD 21636

  AMAZING PRICE REDUCTION - WELL BELOW PROFESSIONAL APPRAISAL - 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 Morton Building with electric and HVAC to house anything needed for your farm. The

  Leslie Fulford Mann & Sons, Inc.

  15184 Jarrell Rd, Goldsboro, MD 21636
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  /10

  $32,000

  • Land
  • 1.00 Acre
  • $32,000 per Acre

  3 Bridges Rd, Federalsburg, MD 21632

  Discover 1 acre of vacant land for sale in peaceful Caroline County, Maryland. Located in Federalsburg, this wooded property offers 110 ft of road frontage along 3 Bridges Rd. The terrain is flat and tree-covered, providing the perfect canvas for a small homestead, garden, or recreational getaway.Property Highlights Size: 1 acre of wooded, undeveloped land Access: 110 ft of road

  Community Lands

  3 Bridges Rd, Federalsburg, MD 21632
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  /51

  Call for Price

  • Land
  • 58 Acres

  4218 Harmony Rd, Preston, MD 21655

  US Treasury Dept. Online Auction - Friday July 25, 2025 - 4218 Harmony Rd., Preston MD 21655 (includes 4228 & 4208 Harmony Rd). Estate property with 8 bedrooms, 8.8 baths, foyer with double staircase, kitchen with butler's pantry, dining room, living room, 2 offices, family room, indoor grill room, 2nd floor family room, 4 fireplaces, gym, laundry room, and attached 3-car and 4-car garages. Over

  Nancy Robbins

  4218 Harmony Rd, Preston, MD 21655
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  /14

  $335,000

  • 3 Beds
  • 2.5 Baths
  • 2,508 Sq Ft

  614 Market St, Denton, MD 21629

  More photos coming soon! Welcome to 614 Market Street. Situated on a corner lot, conveniently located in town of Denton. Just a short walk to downtown to enjoy the local shops, eateries, parks, and the beautiful Choptank River. This historical, charmer will not let you down. Home features a spacious, traditional floor plan, table space in the large kitchen, separate/formal dining room, large

  Michael Bozek Michael J. Bozek

  614 Market St, Denton, MD 21629
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  /19

  $315,000

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft

  14 N Maple Ave, Ridgely, MD 21660

  Fully Renovated Rancher with a bonus shed fitted out with electric and drywall!Welcome to this beautifully remodeled 3-bedroom, 1-bath ranch-style home in the heart of Ridgely, Maryland. Every inch of this home has been thoughtfully updated—featuring a brand new roof, siding, energy-efficient windows, and new front and back doors for enhanced curb appeal and peace of mind.Step inside

  Joshua Clark Chesapeake Real Estate Associates, LLC

  14 N Maple Ave, Ridgely, MD 21660
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  /26

  $335,000

  • 3 Beds
  • 2.5 Baths
  • 1,664 Sq Ft

  504 Pintail St, Greensboro, MD 21639

  Practically New Home in Greensboro, MD — Built in 2024!Why wait to build when you can move right into this stunning, barely lived-in home? Built in 2024 and meticulously maintained, this property offers the perfect blend of modern style and low-maintenance living.Step inside to an inviting open floor plan filled with natural light. The spacious kitchen features sleek granite countertops,

  Kaitlyn Collins Benson & Mangold, LLC

  504 Pintail St, Greensboro, MD 21639
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  /30

  $450,000

  • 4 Beds
  • 2.5 Baths
  • 3,838 Sq Ft

  1111 Daylily Ln, Denton, MD 21629

  Welcome to your dream home at 1111 Daylily Ln, nestled in the desirable community of Cattail Commons. This spacious 4-bedroom, 2.5-bath home offers the perfect blend of functionality and style, thoughtfully designed for everyday living and effortless entertaining.The bright and airy main level features an open-concept kitchen and dining area, ideal for hosting gatherings, along with a

  Joni Barrow Keller Williams Realty

  1111 Daylily Ln, Denton, MD 21629
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  /59

  $374,000

  • 4 Beds
  • 1.5 Baths
  • 2,974 Sq Ft

  107 Butler Dr, Denton, MD 21629

  Charming Home with Timeless Character, Modern Updates & Expansion PotentialStep into this beautifully maintained 4-bedroom, 1.5-bath home that perfectly blends classic charm with thoughtful modern updates. Nestled on a generous 1/3-acre fenced-in town lot, this property offers the privacy and space you’ve been looking for, complete with mature shade trees that create a peaceful,

  Justin Pokrywka Meredith Fine Properties

  107 Butler Dr, Denton, MD 21629
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  /50

  $442,000

  • 4 Beds
  • 2.5 Baths
  • 2,124 Sq Ft

  26674 Bentley Place, Henderson, MD 21640

  This beauty was built in 2004, current owners moved in 2006 added the in-ground salt water pool and property sits on 1.30 acres!! This large 4 bedroom and 2.5 bath home is just the perfect size. Beautiful hard wood floors throughout the first floor, with an open floor plan. Fireplace on first floor runs on propane, which seller does not use or have a propane tank being sold "as-is". The

  Sally Fricke RE/MAX Solutions

  26674 Bentley Place, Henderson, MD 21640
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  /46

  $325,000

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

  8409 Harmony Rd, Denton, MD 21629

  Charming Single-Level Living on 1.14 Acres – Income Potential + Upgrades Galore!Welcome to this Beautifully updated, Move-In-Ready home tucked away on 1.14 Peaceful Acres with mature trees and dual road access (Towers Rd & Harmony Rd). Whether you're looking for comfort, space, or income potential—this property delivers, with the possibility of earning $2,000/month in rental

  Sandra Gendleman Long & Foster Real Estate, Inc.

  8409 Harmony Rd, Denton, MD 21629
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  /64

  $625,000

  • 3 Beds
  • 2.5 Baths
  • 2,060 Sq Ft

  6074 Newton Rd, Preston, MD 21655

  Welome to 6074 Newton Road Preston, MD - Winding gravel drive brings you to 5.82 acres of woods and open spaces on Crowberry Creek just off the Choptank River. Enjoy the walkway to the front door and enter the foyer of this 2,060 Sq. Ft Home. Enjoy as you walk past a more formal living area, past the totally updated Country Kitchen and into the addition of a large Family and Dining area. Just

  James Bent Benson & Mangold, LLC

  6074 Newton Rd, Preston, MD 21655
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  /36

  $339,000

  • 3 Beds
  • 3 Baths
  • 2,016 Sq Ft

  6315 Harmony Rd, Preston, MD 21655

  This spacious Cape Cod is nestled on a half-acre lot offering expansive views of farmland and conveniently located between Easton and Denton. Built in 1994, this home offers over 2,000sqft of living space with 3 bedrooms and 3 full baths. The main level features a comfortable living room that flows into the dining area and a generously sized kitchen with ample cabinet and counter space plus

  Kim Crouch Ozman Benson & Mangold, LLC

  6315 Harmony Rd, Preston, MD 21655
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  /61

  $819,900

  • 4 Beds
  • 3.5 Baths
  • 3,819 Sq Ft

  26943 Fueller Dr, Marydel, MD 21649

  Serene 18-Acre Retreat with Endless Potential!Welcome to your private escape, nearly 18 acres of open space, wooded serenity, and room to bring your vision to life. Whether you're dreaming of a homestead, hobby farm, or multi-use property, this one-of-a-kind opportunity offers versatility, space, and freedom.The home boasts over 3,800 sq ft of thoughtfully designed living space,

  Crystal Smith RE/MAX Executive

  26943 Fueller Dr, Marydel, MD 21649
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  /29

  $422,000

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

  24887 Holsinger Ln, Ridgely, MD 21660

  Welcome to this beautifully maintained property offers the perfect blend of privacy, comfort, and rural charm. Set on an expansive lot, 24887 Holsinger Lane features [insert 3 bedrooms and 2 bathrooms, with an open floor pain for both relaxing and entertaining.Inside, you'll find new hardwood floors, stainless steel appliances and a pellet stove making every room warm and inviting.

  Laura Anthony Benson & Mangold, LLC

  24887 Holsinger Ln, Ridgely, MD 21660
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  /81

  $314,900

  • 3 Beds
  • 2.5 Baths
  • 1,520 Sq Ft

  3995 American Corner Rd, Federalsburg, MD 21632

  Freshly redone and updated 1890 farmhouse with 3 bedroom, 2.5 baths. Spacious kitchen with new stainless appliances. First floor primary bedroom with walk-in closet and private bath.This house is ready for you to move in and make it your own with your furniture and decorations. There is a large screened room on the back of the house to enjoy the outdoors and have room for your crab feasts or

  Earl Sheats Long & Foster Real Estate, Inc.

  3995 American Corner Rd, Federalsburg, MD 21632
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  /6

  $459,000

  • 3 Beds
  • 3 Baths
  • 2,607 Sq Ft

  12615 Eveland Rd, Ridgely, MD 21660

  *COUNTRY living on 1 acre across from Adkins Arboretum. *HORSE farm fields surround. *HOT TUB in covered Gazebo. *60x40 POLE BARN w/200amp and wood stove for winter comfort. RUN A BUSINESS!*LARGE 2BR, 2 BA Rancher w/front porch for sitting & relaxing. *LARGE master suite. *LARGE Living room with Dining "L". *LARGE kitchen w/breakfast bar. *LARGE Sun or Game room. *SEPARATE laundry

  Lynn Collins Long & Foster Real Estate, Inc.

  12615 Eveland Rd, Ridgely, MD 21660
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  /56

  $365,000

  • 3 Beds
  • 2 Baths
  • 2,504 Sq Ft

  135 Kerney St, Federalsburg, MD 21632

  Welcome to this well-maintained home that exudes pride in ownership with just over 2500 square feet of living space. This home boasts upgrades throughout. The kitchen features Granite countertops, stainless steel appliances large island, and a spacious pantry. Large dining room or convert to another living area. Well-appointed bedrooms and a primary with ex large walk-in closet and bathroom. As

  Roger Boyce Chesapeake Real Estate Associates, LLC

  135 Kerney St, Federalsburg, MD 21632
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  /71

  $434,500

  • 4 Beds
  • 3 Baths
  • 4,304 Sq Ft

  122 Lister Ln, Ridgely, MD 21660

  Welcome to 122 Lister Lane in the charming town of Ridgely, MD, nestled on a picturesque corner lot in the highly coveted Lister Estates community. This delightful home is a treasure trove of possibilities, catering to a diverse range of lifestyles.As you approach the property, you'll be greeted by its stunning brick facade that exudes classic elegance, complemented by a fully fenced

  Chris Rosendale CR Realty

  122 Lister Ln, Ridgely, MD 21660
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  /62

  $375,000

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

  1010 S 2nd St, Denton, MD 21629

  1010 S 2nd Street offers in-town living WITHOUT in-town Taxes!!! This home rests at the edge of town on 1.06 acres with mature plantings. This 3-bed 2-bath home boasts hardwood, LVP, and tile floors. A fireplace insert for the pellet stove for heat, while the seller uses the Hot water baseboard as a backup. Full basement for additional entertaining or storage. Screened-in porch overlooks

  Roger Boyce Chesapeake Real Estate Associates, LLC

  1010 S 2nd St, Denton, MD 21629
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  /80

  $409,000

  • 5 Beds
  • 3.5 Baths
  • 2,330 Sq Ft

  13001 Beech Ln, Greensboro, MD 21639

  Your dream home is waiting for you! Nestled in the woods of Fox Grape Farms, 13001 Beech Lane features a DOUBLE LOT giving you just over an acre of land. This 5 Bedroom 3.5 Bathroom home includes, Multiple Outbuildings, Huge Yard, Income Producing Solar Panels, Primary Suite Loft with Balcony, Wood Burning Stove, Recently Remodeled Kitchen, & Wood Burning Fireplace. LVP & hardwood floors

  Megan Rosendale Rosendale Realty

  13001 Beech Ln, Greensboro, MD 21639
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  /34

  $440,000

  • 4 Beds
  • 2.5 Baths
  • 3,096 Sq Ft

  1207 Painted Fern Rd, Denton, MD 21629

  Welcome to 1207 Painted Fern Road — a beautifully maintained and thoughtfully upgraded home nestled in the heart of Denton. This spacious residence offers the perfect blend of modern comfort, functional design, and serene natural surroundings.Step inside to a dramatic two-story foyer that sets an elegant tone for the rest of the home. To the right, a private office provides an ideal space

  Trudie Colvin Coldwell Banker Realty

  1207 Painted Fern Rd, Denton, MD 21629
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  /30

  $349,900

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  15 Ridgeway Dr, Ridgely, MD 21660

  Welcome to 15 Ridgeway Drive! Where comfort, convenience, and pride of ownership meet.This well maintained 3-bedroom, 2-bath home features an additional flex room perfect for a home office, den, or playroom. The updated kitchen features stainless steel appliances and a functional layout that opens into the living space, making it ideal for entertaining or everyday living.Step outside

  Jarnell Foster Benson & Mangold, LLC

  15 Ridgeway Dr, Ridgely, MD 21660
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  /21

  $330,000

  • 3 Beds
  • 2 Baths
  • 1,922 Sq Ft

  27381 Greenwood Rd, Denton, MD 21629

  Surrounded by farmland is what you will find at this spacious 3 bedroom, 2 bath home. Small fenced in area for small pets. Listen to the rain on the tin roof. Galley kitchen opens into the dining area that is open to the large living room. Primary bedroom located on the first floor with an extra-large bathroom. Upstairs bedrooms have mini split systems for heating and air. Plenty of parking

  Pamela Geib Long & Foster Real Estate, Inc.

  27381 Greenwood Rd, Denton, MD 21629
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  /59

  $399,500

  • 3 Beds
  • 2 Baths
  • 2,378 Sq Ft

  502 N Academy St, Greensboro, MD 21639

  Welcome to 502 Academy Street, Greensboro, MD, a charming retreat that embodies the essence of cozy cottage living. This turnkey property has been meticulously cared for and spans almost 2,400 square feet of thoughtfully designed space on a beautifully landscaped lot.Inside, you'll find three inviting bedrooms, with two located on the lower level for added privacy and convenience. Each of the two

  Chris Rosendale CR Realty

  502 N Academy St, Greensboro, MD 21639
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  /47

  $339,990

  • 4 Beds
  • 2 Baths
  • 2,774 Sq Ft

  111 Maple Ave, Greensboro, MD 21639

  SELLER OFFERING CONCESSIONS TOWARD CLOSING !!!Under contract with next home and motivated to sell !!! Welcome to your dream home, a charming farmhouse-style residence that beautifully blends historic character with modern comforts, that is situated on a 0.21 acre lot. Over $70,000 in upgrades since the home was purchased!!! The recently installed 6ft privacy, fenced back yard, brick patio and

  Betsy Brown Long & Foster Real Estate, Inc.

  111 Maple Ave, Greensboro, MD 21639
• 

  

  /19

  $339,000

  • 3 Beds
  • 2 Baths
  • 1,470 Sq Ft

  1206 Trice Meadows Cir, Denton, MD 21629

  Beautiful open floor plan ranch style home in Trice Meadows . Lot backs to elementary school with trees for privacy. Lovely kitchen with granite countertops, all stainless-steel appliances including propane stove top, dishwasher, garbage disposal, built in microwave and refrigerator. The great room offers large dining area with upgraded lighting and living area with propane fireplace. The primary

  Bonnie Johnson Keller Williams Realty

  1206 Trice Meadows Cir, Denton, MD 21629
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  /30

  $385,000

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

  313 S 3rd St, Denton, MD 21629

  Meticulously Maintained & Move In Ready!! Many recent Improvements to this 3 bedroom, 2 bath, Open floor plan rancher with Large Yard, Deck, Multiple Organically prepped Gardens (including an asparagus) ready for your harvest this summer, Covered Porch, Pool with Decking, Oversized 2 Car Garage. Top is off with a large bonus room ready to make it your own! Plenty of off street parking. Close

  Cheri Bruce-Phipps TTR Sotheby's International Realty

  313 S 3rd St, Denton, MD 21629
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  /34

  $299,900

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft

  104 Hobbs St, Greensboro, MD 21639

  Fully Remodeled 3-Bedroom Home – Modern Comfort Meets Timeless CharmWelcome to 104 Hobbs St, where quality craftsmanship and stylish upgrades define this beautifully updated 3-bedroom, 1-bath home with 1,248 square feet of living space. Completely renovated from the studs, this home offers peace of mind with all-new electrical, plumbing systems, HVAC, roof & siding plus a fresh modern

  Brett Schrader Taylor Properties

  104 Hobbs St, Greensboro, MD 21639
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  /18

  $529,000

  • Land
  • 53 Acres
  • $9,979 per Acre

  0 Temple Rd Unit MDCM2006034, Marydel, MD 21649

  This ±53-acre timber property offers a blend of residential potential and quality recreational opportunity. The land features a mix of hardwood and pine stands in various age classes, with a healthy understory, topography changes, and seasonal wetland bottoms—ideal characteristics for managing whitetail deer and turkey habitat.The property consists of five separate parcels, four of which

  Benjamin Alder The Land Group

  0 Temple Rd Unit MDCM2006034, Marydel, MD 21649
• 

  

  /13

  $259,900

  • 2 Beds
  • 1 Bath
  • 869 Sq Ft

  3644 Houston Branch Rd, Federalsburg, MD 21632

  Beautiful immaculate with open floor plan. chefs kitchen, stainlus steel appliances. Granit counters and island. New bathroom, cac with one car garage. 2 acres of land, 2 bedroomand den which could be third bedroom

  Barbara Nichols Results Realty Inc.

  3644 Houston Branch Rd, Federalsburg, MD 21632
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  /9

  $269,900

  • 3 Beds
  • 1.5 Baths
  • 1,584 Sq Ft

  3406 Rose St, Federalsburg, MD 21632

  Totally renovated doublewide. beautiful tile work,large kitchen. new foundation, electric, cacNew dry wall, flooring, roof, welland septic. New concrete pad in rear yard ready for new shed

  Barbara Nichols Results Realty Inc.

  3406 Rose St, Federalsburg, MD 21632
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  /87

  $2,995,000

  • 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
• 

  

  /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
• 

  

  /9

  $99,000

  • Land
  • 3.05 Acres
  • $32,459 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

  Deborah Callahan Benson & Mangold, LLC

  10440 Burrsville Branch Rd, Denton, MD 21629
• 

  

  /17

  $230,000

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  218 E Sunset Ave, Greensboro, MD 21639

  Welcome to 218 E Main St Greensboro, MD. This home offers 3 bedrooms and 1 bath. Home has a large, dethatched garage and off-street parking. Located next to the public boat ramp, with easy access to local shopping and Delaware tax free shopping. This home is located in a flood zone and is being sold as is.

  Dawn Williams Berkshire Hathaway Homeservice Homesale Realty

  218 E Sunset Ave, Greensboro, MD 21639
• 

  

  /42

  $239,000

  • 3 Beds
  • 2 Baths
  • 1,212 Sq Ft

  102 Roe St, Greensboro, MD 21639

  This 3-bedroom, 2-bath bungalow offers the perfect blend of warmth, space, and character. Set on a quiet street just minutes from downtown Greensboro. Step inside to a bright, welcoming living area and enjoy the comfort of a wood stove that keeps the whole house cozy during the winter months.The layout offers flexibility with three comfortable bedrooms and two full baths, providing just

  Jillian Luna Rosendale Realty

  102 Roe St, Greensboro, MD 21639

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