Caroline County MD Homes for Sale

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  /127

  $2,999,000

  • 8 Beds
  • 16 Baths
  • 9,364 Sq Ft

  4218 Harmony Rd, Preston, MD 21655

  A truly rare offering for the discerning auto enthusiast, this exceptional 58.48-acre Eastern Shore estate is a masterfully designed luxury compound where architectural elegance meets world-class automotive accommodations. Introduced by a private gated entrance and tree-lined circular drive, the stately brick home immediately conveys the scale, privacy, and prestige of this one-of-a-kind

  Donna Harrington Coldwell Banker Realty

  4218 Harmony Rd, Preston, MD 21655
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  /38

  $214,900 Open House 1/18

  • 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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  /54

  $549,000 Open Sat 11AM - 1PM

  • 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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  /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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  /64

  $425,000

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

  8578 Tuckahoe Rd, Denton, MD 21629

  This property boasts with a 4 bedroom 3 full bathroom cape cod on a 1 acre lot in a beautiful wide open country setting! Fresh paint throughout the entire house, new refrigerator, new oven, new dryer AND new HVAC! All of the hard work has been done! Minutes to Denton or Easton. Move in ready! There is still plenty of time to be in a new home for the holidays!

  Megan Rosendale Rosendale Realty

  8578 Tuckahoe Rd, Denton, MD 21629
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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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  /46

  $875,000 Coming Soon

  • 4 Beds
  • 3 Baths
  • 3,149 Sq Ft

  3547 Prchal Rd, Preston, MD 21655

  Pride of ownership shines throughout this home, lovingly maintained since 1992. A major renovation in 2006 nearly doubled the living space, transforming this property into a spacious 4-bedroom, 3-bathroom home ideal for comfortable living and entertaining.The impressive 20' x 27' kitchen is the heart of the home, featuring cherry cabinetry, quartz countertops, a walk-in pantry, and a cozy

  Amy Endzel Keller Williams Select Realtors of Annapolis

  3547 Prchal Rd, Preston, MD 21655
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  /35

  $269,900

  • 2 Beds
  • 1 Bath
  • 1,140 Sq Ft

  3540 Houston Branch Rd, Federalsburg, MD 21632

  Welcome to 3540 Houston Branch Rd. It was purchased in 2021 and has undergone extensive renovations. The interior was taken down to the studs. There is new drywall, flooring and sub flooring, a complete bath room, windows, kitchen cabinets, appliances and quartz counter tops. Even the electric was updated along with plumbing. Did I mention a new roof, well and septic system!! This is a perfect

  Eddie Matthews Benson & Mangold, LLC

  3540 Houston Branch Rd, Federalsburg, MD 21632
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  /19

  $299,000

  • 5 Beds
  • 2 Baths
  • 2,574 Sq Ft

  305 Central Ave, Ridgely, MD 21660

  Welcome home to this spacious 5-bedroom, 2-bath Colonial located in the heart of Ridgely. This in-town property offers a large kitchen with plenty of space for cooking and entertaining, a comfortable living room, and generously sized bedrooms throughout. The traditional floor plan provides a warm and inviting flow, perfect for both daily living and hosting guests. Enjoy the convenience of being

  Katie Moore Coldwell Banker Chesapeake Real Estate Company

  305 Central Ave, Ridgely, MD 21660
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  /35

  $349,000

  • 3 Beds
  • 2.5 Baths
  • 1,734 Sq Ft

  206 Charles St, Federalsburg, MD 21632

  This 3-bedroom, 2.5-bath Cape Cod sits on a quiet street surrounded by mature trees. Features include a covered front porch with recessed lighting, family room, formal dining room, eat-in kitchen with stainless steel appliances, and first-floor laundry. Enjoy a fully fenced backyard with a spacious deck and a basketball court in the front yard. Transform the bonus space above the two-car garage

  

  Rosezette Dennis

  Coldwell Banker Realty

  (410) 705-7651

  206 Charles St, Federalsburg, MD 21632
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  /32

  $450,000

  • 1 Bed
  • 1.5 Baths
  • 1,596 Sq Ft

  23629 Willow Pond Rd, Denton, MD 21629

  A Distinctive Live/Work Opportunity on Marylands Eastern Shore. This prime location tucked away between Easton & Denton, is this remarkable and beautifully maintained, 6.18 acre property that combines the tranquility of a pastoral countryside with the practicality of a live/work lifestyle. Set on 6.18 acres of gently rolling land, this is One Lot, divided into 2 parcels, (one 2 .18 Acre and one 4

  Stephany Barrett Long & Foster Real Estate, Inc.

  23629 Willow Pond Rd, Denton, MD 21629
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  /29

  $315,000

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

  121 Edenton Ln, Denton, MD 21629

  This charming rancher offers 3 bedrooms and 2 full bathrooms, nestled on a spacious .5-acre lot. Recent updates include new LVP flooring throughout, a roof replacement in 2018, and newer HVAC, water heater, furnace, siding, and gutter guards (2017). Outside enjoy a new deck and walkways, patio, and large treelined backyard, offering privacy. Located just minutes from downtown Denton and major

  Alicia Gannon Dulin Benson & Mangold, LLC

  121 Edenton Ln, Denton, MD 21629
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  /43

  $399,999

  • 3 Beds
  • 2.5 Baths
  • 3,212 Sq Ft

  21405 Tanyard Rd, Preston, MD 21655

  Peaceful Country Living on 3.2 Acres – Recently Renovated Home with Expansive Pole Barn! Welcome to 21405 Tanyard Rd in Preston, MD – where modern updates meet serene country living. This beautifully renovated 3-bedroom, 3-bath home sits on 3.2 acres—perfect for gardening, raising animals, or simply enjoying wide-open space and quiet surroundings. Step inside to find a bright, freshly updated

  Justin Pokrywka Taylor Properties

  21405 Tanyard Rd, Preston, MD 21655
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  /38

  $220,000

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

  1403 Blue Heron Dr, Denton, MD 21629

  BACK ON THE MARKET Buyer change of plans — which means you get another shot at this amazing home! Don’t miss it this time! Welcome Home to Low-Maintenance Living! 1403 Blue Heron Drive, Denton Step inside this cozy, turn-key 3-level townhome nestled in the highly desired Mallard Landing community! Boasting over 1,680 sq ft, this 3-bedroom, 2.5-bath residence.. The open-concept main floor is

  Dale Hunter Bayside Realty

  1403 Blue Heron Dr, Denton, MD 21629
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  /50

  $410,000

  • 4 Beds
  • 2.5 Baths
  • 2,731 Sq Ft

  406 Morning Glory Dr, Denton, MD 21629

  2020-BUILT EASTERN SHORE COLONIAL EXUDES CHARM & HOSPITALITY ! On the outskirts of historic Denton, you will find this 4-bedroom, 2.5 bathroom home in the pleasant neighborhood of “The Gardens!" This one-owner home offers high-end detailing including a fresh decorator neutral paint palette, free-flowing open concept floor plan, beautiful NEW carpeting, as well as luxury vinyl tile flooring, a

  Mary Stevens Long & Foster Real Estate, Inc.

  406 Morning Glory Dr, Denton, MD 21629
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  $292,990 New Construction

  • 4 Beds
  • 2 Baths
  • 1,460 Sq Ft

  131 Hobbs St, Greensboro, MD 21639

  Welcome to 131 Hobbs Street, a new home soon to be under construction in our newest community, Kinnamon Meadows in Greensboro, MD. 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

  D.R. Horton Builder

  131 Hobbs St, Greensboro, MD 21639
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  /27

  $259,000

  • 3 Beds
  • 2 Baths
  • 1,368 Sq Ft

  229 Oldtown Rd, Goldsboro, MD 21636

  Fully Remodeled 3 Bedroom, 2 Bath Home in the Heart of Goldsboro, MD Welcome to 229 Main Street, where modern style meets small-town charm. This beautifully remodeled 3-bedroom, 2 full bath home has been thoughtfully updated from top to bottom, offering the perfect blend of craftsmanship and comfort. Step inside to a bright, open floor plan featuring luxury vinyl plank flooring, fresh neutral

  Brett Schrader Taylor Properties

  229 Oldtown Rd, Goldsboro, MD 21636
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  /59

  $298,000

  • 2 Beds
  • 1 Bath
  • 1,528 Sq Ft

  506 Park Ave, Ridgely, MD 21660

  Welcome to this delightful 2-bedroom, 1-bath rancher nestled in the heart of Ridgely. Perfectly positioned on a spacious double lot, this home offers abundant outdoor space—ideal for gardening, entertaining, or future expansion. A brand-new roof adds peace of mind and long-term value. Step inside to discover a bright and functional layout featuring a sun-drenched sunroom, a cozy living room with

  Lisa Lynch Keller Williams Realty

  506 Park Ave, Ridgely, MD 21660
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  /2

  $79,000

  • Land
  • 2.11 Acres
  • $37,441 per Acre

  lot 6 Harmony Woods Dr, Preston, MD 21655

  Barbara Nichols Results Realty Inc.

  lot 6 Harmony Woods Dr, Preston, MD 21655
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  /47

  $695,000

  • 4 Beds
  • 2.5 Baths
  • 2,576 Sq Ft

  4757 Long Swamp Rd, Federalsburg, MD 21632

  Welcome to 4757 Long Swamp Rd, a truly unique property in Federalsburg, MD, offering the perfect blend of equestrian facilities and comfortable country living on 7.04 acres. This well-maintained estate is ready for you and your horses, with no restrictions on property use and the added flexibility for the land to be subdivided. The grounds feature expansive pastures secured by electric fencing, a

  Billy Mister Keller Williams Realty

  4757 Long Swamp Rd, Federalsburg, MD 21632
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  /43

  $245,000

  • 3 Beds
  • 1 Bath
  • 1,385 Sq Ft

  511 Bernard Ave, Greensboro, MD 21639

  Spacious rancher located on a double lot, over one-third of an acre, plenty of room for outdoor activities or potential future expansion. This home features solid construction and has had significant updates in the past 3-4 years, including a new roof, new windows, and a new HVAC system, adding considerable value and reduces the worry about major repairs in the near future. Inside the residence

  Karen Clark Clark & Co Realty, LLC

  511 Bernard Ave, Greensboro, MD 21639
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  /125

  $1,295,000

  • 4 Beds
  • 3.5 Baths
  • 4,496 Sq Ft

  24800 Pealiquor Rd, Denton, MD 21629

  Experience timeless elegance and Eastern Shore charm at this beautifully restored 4-bedroom, 3.5-bath colonial retreat set on 7 acres along the Choptank River. Once known as “Hazelwood,” this historic Governor’s Mansion is one you don’t want to miss! Inside, you’ll find expansive formal and informal rooms flow seamlessly for entertaining and family living alike. This estate features refinished

  Christina Ginn Fathom Realty LLC

  24800 Pealiquor Rd, Denton, MD 21629
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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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  /100

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,284 Sq Ft

  2766 Veterans Dr, Federalsburg, MD 21632

  ""PRICE REDUCTION"" *Attention, All "OUTDOOR ENTHUSIAST" are Welcome!!! This Unique Property is comprised of Multiple Deep Water Ponds loaded with a variety of fish making fishing TOP NOTCH and the back Woods loaded with Deer. Truly A Nature Lovers Dream, offers Peace & Tranquility, like no other, You can look long and hard and not find a property like this. This property has a gently rolling

  Barbara Beaudet Brenton Realty Group

  2766 Veterans Dr, Federalsburg, MD 21632
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  /39

  $229,990

  • 3 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  107 Smith St, Federalsburg, MD 21632

  A must see, updated + upgraded, 1-level, 3-bedroom,1.5-bath home with an open floorplan. Situated on a nice-sized yard, this welcoming home offers more than meets the eye. Handsome + durable luxury vinyl plank flooring, fresh paint, and updated fixtures throughout. Spacious living room with a bar and radiant countertops overlook the kitchen. Dining room with breakfast bar and sliding glass door.

  Brandon Brittingham EXP Realty, LLC

  107 Smith St, Federalsburg, MD 21632
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  /15

  $215,000

  • 2 Beds
  • 1 Bath
  • 1,040 Sq Ft

  26732 Idlewild Rd, Federalsburg, MD 21632

  Cute 2 bedroom one story on quiet street. Metal roof. One car garage. Large room off of the kitchen has lots of possibilities, along with the closed in back porch. Updated bathroom. New Andersen windows 2024. New mini Split 2021. Night Owl security with six working cameras. Seamless gutter 2025. Septic cleaned and inspected 2025. Close to nature trails and not far from the boat ramp. Just enough

  Michael Shipley Benson & Mangold, LLC.

  26732 Idlewild Rd, Federalsburg, MD 21632
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  /24

  $299,900

  • 3 Beds
  • 1.5 Baths
  • 864 Sq Ft

  26606 Idlewild Rd, Federalsburg, MD 21632

  Three Bedroom, 1 and a half bathrooms, located on a quiet county road. This house has been freshly painted inside and outside, new LVP flooring installed throughout the house, all interior doors have been replaced with white six panel doors and new light fixtures in each room. New washer/dryer and refrigerator installed, heat pump is 1 year old, and there is a 22 kw Generac generator as a backup

  Robert Bringman Long & Foster Real Estate, Inc.

  26606 Idlewild Rd, Federalsburg, MD 21632
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  /19

  $205,000

  • 2 Beds
  • 1.5 Baths
  • 1,252 Sq Ft

  409 Main St, Goldsboro, MD 21636

  After no fault of the Sellers this property is back to Active and ready for its new Owners. Welcome to 409 Main Street, a delightful 2 bedroom, 1.5 bath home nestled in the heart of Goldsboro. This property features a cozy living room with pellet stove, dining room, a functional kitchen, bonus room (use as an office or 3rd bedroom), comfortable bedrooms and a basement offering endless potential

  Amy Betts Coldwell Banker Realty

  409 Main St, Goldsboro, MD 21636
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  /6

  $159,900

  • Land
  • 5.28 Acres
  • $30,284 per Acre

  0 5 281 Acres Schulyer Rd, Goldsboro, MD 21636

  Peaceful 5.281-Acre Wooded Homesite with Wildlife Pond Views. Discover the perfect blend of natural beauty and rural tranquility on this 5.281-acre perc-approved building lot, ready for your dream home. Nestled in a quiet country setting, this property offers a stunning overlook of a preserved wildlife pond, where geese, ducks, deer, and turkeys are frequent visitors—creating your own private

  Brett Schrader Taylor Properties

  0 5 281 Acres Schulyer Rd, Goldsboro, MD 21636
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  /41

  $269,900

  • 4 Beds
  • 1.5 Baths
  • 2,820 Sq Ft

  306 S Main St, Federalsburg, MD 21632

  Bring Your Fishing Boat! Nestled along the tranquil waters of Marshyhope Creek, this waterfront retreat offers peaceful views and the rare opportunity to fish or kayak directly from your own private shoreline. This charming 2,820 sq. ft. Victorian home features 4 spacious, freshly painted bedrooms and 1.5 baths and is ready for you to add your special touches. Begin your mornings with coffee on

  Mary Mabry Keller Williams Select Realtors of Cambridge

  306 S Main St, Federalsburg, MD 21632
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  /23

  $495,000

  • 0.5 Baths
  • 3,321 Sq Ft

  7 W Belle St, Ridgely, MD 21660

  Over 3,300 sq. ft. two-story building, constructed in 2006, offers endless potential with a little imagina Previously a pharmacy, gift shop, and ice cream parlor, it could easily be transformed into a fantastic four-bedroom, 2.5-bath residence or adapted for other mixed-use purposes. Both levels feature open, flexible layouts—ready to be reimagined to suit your vision. Located in the charming

  Traci Jordan Meredith Fine Properties

  7 W Belle St, Ridgely, MD 21660
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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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  /7

  $127,000

  • Land
  • 4.14 Acres
  • $30,676 per Acre

  0 Burnt Mill Rd Unit MDCM2006400, Ridgely, MD 21660

  Discover the ideal blend of tranquil nature and prime location! 4.14 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

  Stephan Strothe Washington Fine Properties, LLC

  0 Burnt Mill Rd Unit MDCM2006400, Ridgely, MD 21660
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  /20

  $244,900

  • Land
  • 1.65 Acres
  • $148,424 per Acre

  11146 Branch Ct, Denton, MD 21629

  1.65 Acres with Well and Septic in Place!! 3 Bay Garage with one Pass-thru Unit - Features include - extra storage, Office, Kitchenette,and Full Bath. Come Build your Dream Home.!! Lot features U shape Driveway with Plenty of parking and nicely landscaped with mature trees. . Check with County for all your many possiblities! Conviently located with in minutes to Downtown Denton, Choptank River

  Kathleen Brenton Brenton Realty Group

  11146 Branch Ct, Denton, MD 21629
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  /49

  $797,500

  • 3 Beds
  • 2 Baths
  • 2,342 Sq Ft

  12618 Knife Box Rd, Greensboro, MD 21639

  Custom home built in 2007, this home features a large eat in kitchen, a lovely screened porch over looking the park like property. Living room featuring a fireplace, and tray ceiling. to add another cozy feature. Hard wood flooring through out the living space gives that warm welcoming vibe. The property has the potential to be off the grid, the geothermal system is the basis., and a wood stove

  Kat Thompson Benson & Mangold, LLC.

  12618 Knife Box Rd, Greensboro, MD 21639
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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; pantry in the kitchen, family room with pellet stove and brick fireplace that can burn wood; 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, wildlife, and more. Want horses; this

  Bonnie Duley Long & Foster Real Estate, Inc.

  28402 Liden School Rd, Denton, MD 21629
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  /24

  $208,000

  • 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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  /22

  $150,000

  • 4 Beds
  • 1.5 Baths
  • 2,668 Sq Ft

  208 N Main St, Federalsburg, MD 21632

  Traditional Victorian. 4 bedrooms, 1 1/2 baths, basement, attic, wraparound porch.Sold as is. Cash or conventional financing. Estate of Bonnie Jefferson.

  Barton Johnson/not int Marshy Hope Realty LLC

  208 N Main St, Federalsburg, MD 21632
• 

  

  /41

  $319,900

  • 3 Beds
  • 2.5 Baths
  • 1,364 Sq Ft

  406 Wood Duck Dr, Greensboro, MD 21639

  MOTIVATED SELLER! Schedule and tour, fall in love, and write an offer! Featuring a traditional two story floor plan, this home welcomes you from the start. This 3 bedroom, and 2.5 bathroom home offers a move in ready space to make your own! As you enter you’ll love the newer vinyl plank flooring throughout the main level, with fresh paint. The family room, and near by dining room gives ample

  Brittany Gough RE/MAX One

  406 Wood Duck Dr, Greensboro, MD 21639
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  /28

  $399,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 1,768 Sq Ft

  1 Sunrise Ave, Ridgely, MD 21660

  As morning light rises over Sunrise Village, this home, The Sunshine, thoughtfully crafted by local builder Lomaxx Custom Homes comes to life. Golden light spills across the nearby fields and settles gently indoors, where days begin with coffee on the porch, birds gliding by, and daylight drifting through the windows, filling each room with a calm, welcoming glow. Designed for easy, everyday

  Crystal Smith RE/MAX Executive

  1 Sunrise Ave, Ridgely, MD 21660

Showing Results 41 - 80, Page 2 of 4