Caroline County MD Homes for Sale

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  /8

  $69,000

  $16K PRICE DROP

  • Land
  • 32,234 Sq Ft
  • $93,243 per Acre

  0 Mill & Lincoln St, Greensboro, MD 21639

  With LAND becoming less and less available, here is your opportunity to own 3 PARCELS in the Town of Greensboro!! At least one of which has a hooked up Water/Sewer account, so INSTANT SAVINGS on no tap fee!! AND WITH THIS NEW PRICE, DON'T HESITATE -- GREAT PRICE & GREAT OPPORTUNITY! Parcels are believed to total approximately 0.74 Acres, more or less. Abandoned dwelling exists in the center of

  Erin Anderson Chesapeake Real Estate Associates, LLC

  0 Mill & Lincoln St, Greensboro, MD 21639
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  /23

  $230,000

  • 2 Beds
  • 1 Bath
  • 1,108 Sq Ft

  3894 Old Denton Rd, Federalsburg, MD 21632

  Nestled in a quiet setting, 3894 Old Denton Rd is a charming rancher that offers the ease of true single-level living. The home features an inviting, open layout where a spacious living room leads into the kitchen and dining area, making it feel bright and connected. Two comfortable bedrooms are tucked away for privacy, while a bright sunroom, a covered front porch, and a rear screened porch

  Billy Mister Keller Williams Realty

  3894 Old Denton Rd, Federalsburg, MD 21632
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  /41

  $319,900

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,436 Sq Ft

  110 N School St, Greensboro, MD 21639

  Why wait for new construction? Completed in 2025, this custom-built, move-in ready rancher offers 1,436 square feet of thoughtfully designed, single-level living--with no HOA. The bright, open-concept living, dining, and kitchen area features nine-foot ceilings, solid hardwood flooring and recessed LED lighting. The kitchen is finished with granite countertops, all-wood cabinetry, Samsung

  

  Bonnie Duley

  Long & Foster Real Estate, Inc.

  110 N School St, Greensboro, MD 21639
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  /2

  $499,999

  New Construction

  • 4 Beds
  • 2 Baths
  • 1,613 Sq Ft

  25660 Cherry Blossom Ln, Denton, MD 21629

  Beautiful to be built new construction on 1.8 acres just outside Denton. This home offers 4 bedrooms, 2 full baths, great open kitchen with island, pantry, separate laundry room, large family room plus dining area. The crawl space will be conditioned for total peace of mind. The garage is huge measuring 32x22 and will be fully insulated with R19 Batts insulation. There will be a slider leading to

  Bonnie Johnson Keller Williams Realty

  25660 Cherry Blossom Ln, Denton, MD 21629
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  /42

  $359,000

  $20K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,712 Sq Ft

  410 Wood Duck Dr, Greensboro, MD 21639

  Welcome to this spacious three-level home offering flexible living space and a functional floor plan! The main level features a bright living room that flows in the open kitchen. Separate dining room for those family gatherings. Also, on this level is a half bath and a small guest bedroom or turn into your reading area or an office space. Upstairs, you'll find three additional bedrooms and the

  Pamela Geib Long & Foster Real Estate, Inc.

  410 Wood Duck Dr, Greensboro, MD 21639
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  /8

  $17,000

  • Land
  • 8,712 Sq Ft
  • $85,000 per Acre

  0 Brooklyn Ave, Federalsburg, MD 21632

  Opportunity awaits in Federalsburg! This residential lot offers the convenience of public water and sewer connections, making it a great option for your next build or investment project. Located close to local shops, dining, schools, and everyday amenities, this property provides both accessibility and potential. The lot next door is also available for sale, creating an opportunity to purchase

  Aubrey Campbell Keller Williams Realty Delmarva

  0 Brooklyn Ave, Federalsburg, MD 21632
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  /42

  $329,900

  $29K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 1,800 Sq Ft

  222 S 2nd St, Denton, MD 21629

  This is 222 S. 2nd Street, a recently renovated home with historic charm.Original wood flooring, and architectural details such as moldings and antique door knobs highlight the home's history.Though it embraces the past, the house has been updated with all new appliances, new quartz kitchen countertops, newly painted walls and new siding.The house offers something that

  Kathleen Brenton Brenton Realty Group

  222 S 2nd St, Denton, MD 21629
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  /6

  $49,900

  • Land
  • 2.55 Acres
  • $19,569 per Acre

  0 Havercamp Rd, 4, Preston, MD 21655

  If you’ve been searching for a private, wooded homesite without feeling too far removed from everyday conveniences, this is it. Offering over 2.5 acres, this property provides the perfect blend of seclusion and accessibility—ideal for building your dream home exactly the way you envision it. Located on Havercamp Rd, you’ll enjoy a peaceful, tucked-away setting while still being just minutes from

  Aubrey Campbell Keller Williams Realty Delmarva

  0 Havercamp Rd, 4, Preston, MD 21655
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  /2

  $190,000

  $70K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,280 Sq Ft

  27944 Possum Hill Rd, Federalsburg, MD 21632

  Lovely two bedroom one bath rancher with spacious living room and dining room plus kitchen **1 car garage plus 30 x 30 storage area ** Heating is oil furnace 3 years old** Hot water tank is 3 years old **1.42 acres ** very flat usable lot

  Bev Langley Coldwell Banker Realty

  27944 Possum Hill Rd, Federalsburg, MD 21632
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  /2

  $299,990

  New Construction $2K PRICE DROP

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

  121 Hobbs St, Greensboro, MD 21639

  Come discover 121 Hobbs Street, a new home under construction in the quaint Kinnamon Meadows community of 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 the

  D.R. Horton Builder

  121 Hobbs St, Greensboro, MD 21639
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  /4

  $1,200,000

  $400K PRICE DROP

  • Land
  • 11 Acres
  • $109,091 per Acre

  0 Liberty (Rifkin Village) Rd Unit MDCM2007390, Federalsburg, MD 21632

  Ready for Development! Owner financing possible with down payment. Terms negotiable. 43 lots within the Town limits of Federalsburg, Maryland. Total lot space as currently platted is 478,596 sq ft or 11 acres, according to public records. Total property area including the unbuilt road space is roughly 13 acres. Right-of-ways to the property are currently platted from Liberty Rd, Bernard Ave, and

  Aaron Dixon Berkshire Hathaway HomeServices PenFed Realty

  0 Liberty (Rifkin Village) Rd Unit MDCM2007390, Federalsburg, MD 21632
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  /40

  $280,000

  $25K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 1,884 Sq Ft

  407 W Sunset Ave, Greensboro, MD 21639

  Charming 5BR detached home, located in a quiet neighborhood in Greensboro. Experience the great outdoors in your own backyard on a nearly 1/2 acre lot, adjacent to 140 acres of farmland. Enjoy the 'Sunset' from the 320 sf sunroom with sliding glass doors, or sit outside to watch the sunrise on the new 230 sf wooden front porch. Several updates include replacement windows, upgraded plumbing &

  Raphael Szendro R&R Executive Realty

  407 W Sunset Ave, Greensboro, MD 21639
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  /20

  $225,000

  • 4 Beds
  • 1 Bath
  • 1,350 Sq Ft

  5258 Preston Rd, Federalsburg, MD 21632

  4 bedrooms 1 bathroom bungalow being sold "AS IS". 16,700 sq. ft. lot with detached garage. Priced to Sell.Updated 200. amp electric service.

  Barton Johnson/not int Marshy Hope Realty LLC

  5258 Preston Rd, Federalsburg, MD 21632
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  /2

  $25,000

  • Land
  • 12,196 Sq Ft
  • $89,286 per Acre

  12087 Wayman St, Ridgely, MD 21660

  Double lot . There are the remains of a house on the property; please leave the remains "as is". Well and septic unknown.

  Bev Langley Coldwell Banker Realty

  12087 Wayman St, Ridgely, MD 21660
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  /23

  $289,990

  New Construction $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,219 Sq Ft

  109 Hobbs St, Greensboro, MD 21639

  Welcome to 109 Hobbs Street where a new home can be yours in Kinnamon Meadows in Greensboro, MD. This home is not currently under construction. The Sullivan is a charming 1,219-square-foot, cottage-style ranch home featuring three bedrooms, two bathrooms, and a one-car garage. Just off the foyer, two spacious guest bedrooms and a shared full bathroom offer comfort and privacy for family or

  Justin Wood D.R. Horton Realty of Virginia, LLC

  109 Hobbs St, Greensboro, MD 21639
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  /30

  $348,000

  $7K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  8140 Haven St, Denton, MD 21629

  This charming ranch-style home, built in 1986, offers a perfect blend of comfort and functionality. Minutes to Tuckahoe Creek boat ramp! With 1,300 sq. ft. of well-designed space, it features three inviting bedrooms and two full bathrooms, including a primary suite with a walk-in closet and a tub/shower. The traditional floor plan is enhanced by built-ins and ceiling fans, creating a cozy

  Mary Haddaway Benson & Mangold, LLC

  8140 Haven St, Denton, MD 21629
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  /67

  $629,000

  $50K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,744 Sq Ft

  132 Deep Shore Rd, Denton, MD 21629

  Welcome to 132 Deep Shore Rd—an inviting homestead set on more than 3 acres of beautifully maintained gardens, thoughtfully designed outdoor spaces, and versatile outbuildings. From greenhouse and herb beds to a dedicated drying room and casual nooks for lounging, every corner invites you to savor the seasons.Inside, this spacious home offers over 2,700 sq ft with 4 bedrooms and 2.5

  Roger Boyce Chesapeake Real Estate Associates, LLC

  132 Deep Shore Rd, Denton, MD 21629
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  /53

  $525,000

  • 2 Beds
  • 1 Bath
  • 1,292 Sq Ft

  5820 Bell Creek Rd, Preston, MD 21655

  Don’t miss this exceptional 20+/- acre working horse farm thoughtfully designed for both functionality and country living. This well-equipped equestrian property offers everything needed for training, boarding, riding, and daily farm operations. The property features a 36’ x 40’ center-aisle barn with 9 stalls, water, electric, and an insulated tack room, along with a 77’ x 36’ metal barn

  Colleen Smith EXP Realty, LLC

  5820 Bell Creek Rd, Preston, MD 21655
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  /8

  $239,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft

  205 Park Ave, Federalsburg, MD 21632

  Framing has begun! Schedule your tour today!The photos provided in the MLS are for reference purposes only and are intended to reflect the style and quality of similar fixtures, finishes, and features. Actual materials, fixtures, finishes, and selections may vary based on builder availability and final specifications. **Get it under contract prior to completion**Welcome to 205 Park

  Erene Katris Coldwell Banker Realty

  205 Park Ave, Federalsburg, MD 21632
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  /55

  $435,000

  $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,720 Sq Ft

  25485 Hignutt Rd, Denton, MD 21629

  SELLER WILL CONSIDER CONTRIBUTING TOWARD THE BUYER’S ALLOWABLE CLOSING COSTS WITH AN ACCEPTABLE OFFER!Welcome to 25485 Hignutt Road—a completely renovated 3-bedroom, 2.5-bath home situated on nearly half an acre in a peaceful country setting, just minutes from Denton’s shopping, dining and everyday conveniences.This truly move-in-ready home offers comfortable one-level living with

  Justin Pokrywka Taylor Properties

  25485 Hignutt Rd, Denton, MD 21629
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  /29

  $700,000

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 4,580 Sq Ft

  14236 Drapers Mill Rd, Greensboro, MD 21639

  STOP, LOOK, and READ...this may be exactly the property you’ve been searching for!! RESIDENTIAL / COMMERCIAL OPPORTUNITY – Zoned C-2, this versatile multi-use property offers endless possibilities! Relocate your business, expand to a second location, or launch your next venture while enjoying the convenience of living and working side by side on this incredible 2+ acre property. This unique

  Karen Clark Clark & Co Realty, LLC

  14236 Drapers Mill Rd, Greensboro, MD 21639
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  /40

  $345,000

  $15K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,056 Sq Ft

  608 Market St, Denton, MD 21629

  Full Re-Hab 2023! Home shows well. The best of Downtown Living! This refurbished Farmhouse, has all the feels of intown country living with all the new modern ammenties! Large Eat- in Kitchen with Tons of Storage! Family Room with Fireplace, leads to a side yard Patio for entertaining! Upstairs you will find three nice size Bedrooms, 2 Full Baths, and a Loft area. Attic has finished space

  Kathleen Brenton Brenton Realty Group

  608 Market St, Denton, MD 21629
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  /11

  $224,900

  $45K PRICE DROP

  • Land
  • 14.71 Acres
  • $15,289 per Acre

  0 Trunk Rd Unit MDCM2007270, Henderson, MD 21640

  Discover the possibilities on this 14.71± acre wooded parcel on Trunk Line Rd in Henderson, MD, now offered at $224,900. Perc approved for a conventional septic system serving a 4+ bedroom dwelling, this property offers the opportunity to build a custom home while enjoying the privacy and space of a rural setting. With approximately 466 feet of road frontage along Trunk Line Road and a designated

  Heather Branham The Parker Group

  0 Trunk Rd Unit MDCM2007270, Henderson, MD 21640
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  /27

  $299,000

  $40K PRICE DROP

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

  208 Oriole Ave, Ridgely, MD 21660

  Charming 3-bedroom, 2-bath rancher located in Ridgely! Inside, you’ll find comfortable one-level living with a functional open layout connecting the living room and kitchen, complete with stainless steel appliances. The spacious primary suite features a large en-suite bath and private doors leading directly to the backyard deck. Two additional generously sized bedrooms provide plenty of space for

  Lish Gannon Dulin Benson & Mangold, LLC

  208 Oriole Ave, Ridgely, MD 21660
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  /20

  $350,000

  $50K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,128 Sq Ft

  26784 Bilbrough Rd, Goldsboro, MD 21636

  Welcome to your private slice of Eastern Shore living in Goldsboro. Set on 4.7 secluded acres, this 2022-built home offers the space, comfort, and modern features today's market demands. With over 2,100 square feet, 4 bedrooms, and 2 full baths, the layout is open, bright, and designed for seamless everyday living.Step inside to a spacious floor plan that flows effortlessly from room to

  Sandra Bradley Keller Williams Select Realtors of Easton

  26784 Bilbrough Rd, Goldsboro, MD 21636
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  /27

  $369,900

  $5K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 2,268 Sq Ft

  803 Market St, Denton, MD 21629

  This inviting Victorian offers 4 bedrooms and 1.5 baths, that’s perfect for unwinding at the end of the day. Inside, natural light fills the main level, highlighting warm hardwood floors and comfortable living spaces. The living and dining areas connect seamlessly, creating an easy flow for everyday living. The kitchen features ample cabinet and counter space, stainless steel appliances, and a

  Steven Parsons Coldwell Banker Realty

  803 Market St, Denton, MD 21629
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  /62

  $375,000

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

  1010 S 2nd St, Denton, MD 21629

  Nestled on the edge of town, 1010 S 2nd Street delivers the convenience of in-town living without in-town taxes. Situated on 1.06 beautifully landscaped acres with mature plantings, this 3-bedroom, 2-bath home offers a spacious feel inside and out. Interior features include hardwood, LVP, and tile flooring, along with a cozy pellet stove fireplace insert for efficient heating, complemented by hot

  Roger Boyce Chesapeake Real Estate Associates, LLC

  1010 S 2nd St, Denton, MD 21629
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  /18

  $219,900

  $60K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,694 Sq Ft

  156 Main St, Preston, MD 21655

  Located in the heart of Preston, this classic 1900-built home offers a solid opportunity for both homeowners and investors alike. Inside, the home features 3 bedrooms and1.5 bathrooms and a functional layout that includes a combined laundry room, bath, and mudroom with direct access to the back deck—adding everyday practicality. The kitchen has been updated with durable luxury vinyl plank (LVP)

  Chuck Mangold Benson & Mangold, LLC

  156 Main St, Preston, MD 21655
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  /63

  $399,000

  $9K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  7392 Todds Wharf Rd, Preston, MD 21655

  This very comfortable rancher has ramps at rear of home for accessibility for those not able to walk up steps very well. Roomy kitchen and open floor plan allows large gatherings to enjoy the roominess. Large counter seats 4 comfortably. Dining area for full-size table and chairs. Working stone wood-burning fireplace is great for use to heat home all winter or just on-call use when you want the

  

  Bonnie Duley

  Long & Foster Real Estate, Inc.

  7392 Todds Wharf Rd, Preston, MD 21655
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  /12

  $575,000

  • Land
  • 61.88 Acres
  • $9,292 per Acre

  17619 Melville Rd, Henderson, MD 21640

  The Melville Rd Farm is located on the east side of Melville Road and is bordered to the north by Trunk Line Road. The property includes approximately 51± acres of tillable ground along with 11± acres of wooded areas primarily situated around drainage ditches, providing natural transitions and wildlife cover. Two transmission lines run through the center of the farm, offering access corridors and

  Benjamin Alder The Land Group

  17619 Melville Rd, Henderson, MD 21640
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  /36

  $425,000

  $20K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,492 Sq Ft

  1709 Cattail Commons Way, Denton, MD 21629

  Welcome to 1709 Cattail Commons Way, located in the highly desirable Savannah Overlook community in Denton, MD. This beautifully maintained 4-bedroom, 2.5-bath home offers a spacious open floor plan, modern upgrades, and move-in ready convenience—perfect for today’s buyer seeking comfort, functionality, and style.The main level features a bright and open layout ideal for both everyday

  Kaitlyn Collins Benson & Mangold, LLC

  1709 Cattail Commons Way, Denton, MD 21629
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  /29

  $284,900

  $45K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 1,350 Sq Ft

  115 Boyce Mill Rd, Greensboro, MD 21639

  Welcome to this charming, Cape-Cod with a Full Unfinished basement—perfectly nestled on a spacious 1/2 Acre! This property gives you that “welcome home” feeling the moment you arrive.Inside, you’ll find a bright and inviting living area featuring a cozy electric fireplace insert and beautiful wood‑beam accents. The freshly renovated kitchen is thoughtfully designed and opens seamlessly to

  Kathleen Brenton Brenton Realty Group

  115 Boyce Mill Rd, Greensboro, MD 21639
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  /18

  $115,000

  $5K PRICE DROP

  • Land
  • 1.89 Acres
  • $60,847 per Acre

  27202 Sandtown Rd, Goldsboro, MD 21636

  Discover the perfect blend of tranquility and convenience with this perc-approved 1.88-acre homesite, ready for your dream build. Overlooking a scenic tributary of the Upper Choptank River, this property offers breathtaking natural views and a serene setting that wildlife enthusiasts will truly appreciate. Ducks and geese are common visitors on the water with fishing right in your back yard.

  Brett Schrader Taylor Properties

  27202 Sandtown Rd, Goldsboro, MD 21636
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  /2

  $215,000

  • 3 Beds
  • 1 Bath
  • 756 Sq Ft

  105 Lincoln St, Greensboro, MD 21639

  Tenant-occupied property offering an excellent investment opportunity with immediate rental income. Current lease in place through July 31st. Tenants have expressed interest in renewing and would prefer to stay, providing potential for continued occupancy. Property is well-maintained and conveniently located near local amenities, schools, and major routes.Please allow adequate notice for all

  emily conley Taylor Properties

  105 Lincoln St, Greensboro, MD 21639
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  /22

  $174,000

  $15K PRICE DROP

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

  107 Smith St, Federalsburg, MD 21632

  Move-In Ready & Beautifully Remodeled!This charming 3-bedroom, 1.5-bath home offers the perfect blend of comfort and convenience. Enjoy a spacious living room, separate dining area, and a dedicated laundry room for added functionality.The kitchen is designed for both everyday living and entertaining, featuring dual bar seating areas with open views to the living and dining spaces. One

  Dawn Hubbard Keller Williams Select Realtors of Cambridge

  107 Smith St, Federalsburg, MD 21632
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  /37

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,222 Sq Ft

  7192 American Corner Rd, Denton, MD 21629

  Come make this updated and move in ready rancher your new home. Considerable improvements have been made over the last two years to include the following. This home has a new deep well, new septic system, new tankless propane water heater, new washer/dryer. new range and refrigerator, new roof, new siding, new hvac, renovated bathroom, new flooring, fresh paint, new privacy and chain link fencing

  Andrew Beaven Wright Real Estate

  7192 American Corner Rd, Denton, MD 21629
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  /15

  $289,900

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft

  506 Pintail St, Greensboro, MD 21639

  Nearly new ranch style home with large front porch. Three bedrooms and two full baths plus spacious laundry room enhance this home. Large kitchen with center island with stainless appliances and granite countertops are a focal point of this open floor plan. Move in ready and waiting for a new family!

  Bonnie Johnson Keller Williams Realty

  506 Pintail St, Greensboro, MD 21639
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  /41

  $579,900

  $15K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,643 Sq Ft

  24766 Tribbett Cir, Ridgely, MD 21660

  Welcome to this meticulously crafted 2023 contemporary farmhouse, perfectly positioned on a spacious .85-acre lot in the established community of Ashworth. Offering 3,168 square feet, 4 bedrooms, and 2.5 baths, this beautifully designed home blends timeless farmhouse charm with modern finishes and thoughtful upgrades throughout. The striking exterior showcases classic white siding, bold black

  Barbara McCaffrey Redfin Corp

  24766 Tribbett Cir, Ridgely, MD 21660
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  /29

  $669,000

  $131K PRICE DROP

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

  1108 Camp Rd, Denton, MD 21629

  Price Reduction! Motivated Seller. Welcome to 1108 Camp Street, sits on over 14 acres of land where modern comfort meets elegant design through an extensive list of upgrades that enhance both functionality and style.Secluded in a great location for Dirt biking, bow hunting. The included outbuilding is great for car enthusiast.This home features stunning stone work on both the front and

  Michelle Anderson Coldwell Banker Premier - Rehoboth

  1108 Camp Rd, Denton, MD 21629
• 

  

  /21

  $229,000

  $10K PRICE DROP

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

  103 Riverwalk Terrace, Federalsburg, MD 21632

  Hurry before it’s gone! This is an opportunity to buy in the sold out community of Riverwalk Terrace. The owner stayed at the home a few times some of the appliances never used. Open floor plan 1365 square feet , 3 bedrooms and 2.5 baths easy living. Only 2 years young this unit feels like new, was never a rental barley lived in. also backs up to the woods the private side of the community.

  Kat Thompson Benson & Mangold, LLC.

  103 Riverwalk Terrace, Federalsburg, MD 21632

Showing Results 81 - 120, Page 3 of 4