Caroline County MD Houses 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

  $369,900

  • 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
• 

  

  /31

  $345,000 Open Sun 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,772 Sq Ft

  1109 Trice Meadows Cir, Denton, MD 21629

  Welcome to 1109 Trice Meadows Circle — a beautifully refreshed and move-in-ready 3-bedroom, 2-bath rancher nestled in the desirable Trice Meadows community in charming Denton, Maryland. This thoughtfully updated home offers a perfect blend of comfort, style, and convenience, making it an ideal choice for anyone looking to settle into a peaceful neighborhood setting with modern features already in

  Laura Anderson Coldwell Banker Realty

  1109 Trice Meadows Cir, Denton, MD 21629
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  /44

  $449,900

  • 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 ample space, comfort, and convenience—perfect for growing families or those who love to entertain. Property hightlights include: Updated kitchen featuring brand-new stainless steel

  Barbara Blosser Long & Foster Real Estate, Inc.

  8 W Liberty St, Ridgely, MD 21660
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  /65

  $465,000

  • 4 Beds
  • 4 Baths
  • 3,408 Sq Ft

  135 Walnut St, Ridgely, MD 21660

  Welcome to this Grande Home in Lister Estates. This home offer Three Full Levels of living space. Main floor features the Owners Primary with En Suite and two closets. 2 additional bedrooms and full bath. Dining Room or Office, Large open kitchen overlooks Great Room and added Morning Room for additional dining or needed space. Exterior backyard offers deck for entertaining and area for garden

  Roger Boyce Chesapeake Real Estate Associates, LLC

  135 Walnut St, Ridgely, MD 21660
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  /43

  $399,000 Open Sat 10AM - 12PM

  • 5 Beds
  • 2.5 Baths
  • 2,267 Sq Ft

  306 S 2nd St, Denton, MD 21629

  Location! Location! Welcome to 306 S 2nd St, (highly sought after area in town Denton), a lovingly restored colonial farmhouse style home on a private lane in a great neighborhood. Situated on a large in-town lot, the home features gleaming hardwood floors, new carpeting, and well-maintained gardens. From roof to basement, nearly everything in this home has been updated or upgraded. New

  Jana Meredith Meredith Fine Properties

  306 S 2nd St, Denton, MD 21629
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  /40

  $485,000

  • 3 Beds
  • 2 Baths
  • 1,952 Sq Ft

  8452 Harmony Rd, Denton, MD 21629

  Huge price improvement! Your Own Slice of Paradise!Pride of ownership shines throughout this beautifully updated rancher, perfectly nestled on 4 acres of serene countryside complete with a pond stocked with koi, catfish and goldfish—a dream setting for nature lovers and outdoor enthusiasts alike. Step inside and fall in love with the modern touches and thoughtful upgrades throughout.

  Tracey Bellotte Coldwell Banker Realty

  8452 Harmony Rd, Denton, MD 21629
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  /29

  $335,000

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

  614 Market St, Denton, MD 21629

  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 home office, welcoming

  Michael Bozek Michael J. Bozek

  614 Market St, Denton, MD 21629
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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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  /44

  $419,900

  • 3 Beds
  • 3 Baths
  • 1,884 Sq Ft

  14267 Cherry Ln, Queen Anne, MD 21657

  Enjoy peaceful rural living in this beautifully crafted home on over 2 wooded acres. Features include exposed wood beams, hardwood floors, a cozy wood stove, stunning stone fireplace, country kitchen, and clawfoot soaking tub. Relax on the large front porch or back deck surrounded by nature. Includes a spacious detached garage/workshop, new roof, and freshly painted exterior. Don’t miss the

  Rick Parreco RE/MAX Executive

  14267 Cherry Ln, Queen Anne, MD 21657
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  /30

  $430,000

  • 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

  Welcome to 6074 Newton Road Preston, MD - Winding gravel drive invites you to 5.82 acres, a Nature Lover's Paradise of woods and open spaces on Crowberry Creek just off the Choptank River. Enjoy the stone walkway heading 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

  James Bent Benson & Mangold, LLC

  6074 Newton Rd, Preston, MD 21655
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  /36

  $325,000

  • 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

  $415,000

  • 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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  /56

  $357,000

  • 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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  /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
• 

  

  /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
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  /30

  $289,000

  • 3 Beds
  • 1.5 Baths
  • 1,092 Sq Ft

  312 Fountain Ave, Denton, MD 21629

  Charming in-town living in this Beautifully Remodeled 3-Bedroom Rancher! Updates include Fresh Paint, NEW Luxury Vinyl Plank Flooring, NEW Kitchen Cabinets, NEW Tile Backsplash and NEW Quartz Countertops! Ceiling Fans in all Bedrooms, Living Room and Dining area to ensure comfort throughout. Turn-Key and ready for you to move right in! Situated on a large Corner Lot with a Spacious Driveway

  Pamela Ackermann-Doll RE/MAX Executive

  312 Fountain Ave, Denton, MD 21629
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  /18

  $119,000

  • 2 Beds
  • 2 Baths
  • 1,520 Sq Ft

  215 Academy Ave, Federalsburg, MD 21632

  This property offers an exceptional chance for a BRRRR investment, fix and flip opportunities or a DIY restoration project. Recent improvements, including partial window replacements and a newer roof, set the stage for a transformative renovation. The property features two bedrooms on the second floor, a bonus room, two bathrooms, a flex room, an enclosed front porch, large driveway and a fairly

  Nora Turner Long & Foster Real Estate, Inc.

  215 Academy Ave, Federalsburg, MD 21632
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  /33

  $289,000

  • 3 Beds
  • 1 Bath
  • 1,392 Sq Ft

  6101 Bethlehem Rd, Preston, MD 21655

  Charming 3-bedroom, 1-bathroom home on 1.3 acres with room to grow! This well-maintained, one-family-owned property features recent upgrades throughout, including a new roof (2024), hot water heater (2023), new appliances and countertops (2024), fresh paint (2024), new fencing (2024), and a brand-new septic system. The oversized 2-car garage offers ample storage or workspace. The primary bedroom

  Katie Moore Coldwell Banker Chesapeake Real Estate Company

  6101 Bethlehem Rd, Preston, MD 21655
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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
• 

  

  /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
• 

  

  /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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  /89

  $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
• 

  

  /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
• 

  

  /28

  $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
• 

  

  /13

  $79,900

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  27980 Ruritan Rd, Denton, MD 21629

  CALLING ALL INVESTORS! This property in Denton is the one you have been waiting for! This one will not last! This Property is being sold As-Is condition. Buyer is responsible for all certifications. Seller never occupied. Neither the seller or listing agent make any representation as to the accuracy of any information contained herein. Buyer must conduct their own due diligence, verification,

  Megan Carpenter Tesla Realty Group, LLC

  27980 Ruritan Rd, Denton, MD 21629
• 

  

  /4

  $35,000

  • 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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