Caroline County MD Houses for Sale

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  /38

  $479,000

  • 4 Beds
  • 2.5 Baths
  • 2,747 Sq Ft

  8605 Hickory Place, Denton, MD 21629

  Beautiful Colonial Farmhouse nestled on a wooded lot at the end of a cul-de-sac private lane. This 4 bedroom, 2.5 bath home has been meticulously maintained and features a traditional floor plan with a large kitchen/breakfast area, large family room with vaulted ceilings and a gas fireplace, separate dining room, living room/office. Second floor includes a primary suite with large bathroom with a

  

  Brian Gearhart

  Benson & Mangold, LLC

  8605 Hickory Place, Denton, MD 21629
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  /28

  $595,000

  • 3 Beds
  • 3.5 Baths
  • 3,276 Sq Ft

  23730 Henry Rd, Ridgely, MD 21660

  Beautiful Craftsman Cape Cod on quiet country road in Caroline County. This 3,200 sq ft home was built in 2023 and offers an open floor plan with all the amenities...large family room with vaulted ceilings, private office, large kitchen with white cabinets, farm sink, SS appliances, separate butler's pantry, and separate laundry room, first floor primary with walk-in closet, high-end primary

  

  Brian Gearhart

  Benson & Mangold, LLC

  23730 Henry Rd, Ridgely, MD 21660
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  /68

  $329,900

  $20K PRICE DROP

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

  110 N School St, Greensboro, MD 21639

  Price to purchase has been lowered to help you afford top quality at a fantastic price. Come see this beautiful home. Pride of ownership is shown from top to bottom in this magnificent rancher! This custom-built home was completed in June 2025 and is like new. The owner took much pride in everything he installed/built and makes this home very desirable. The nine-foot (9') ceilings add the feeling

  

  Bonnie Duley

  Long & Foster Real Estate, Inc.

  110 N School St, Greensboro, MD 21639
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  /87

  $1,550,000

  • 5 Beds
  • 4.5 Baths
  • 4,853 Sq Ft

  322 S 2nd St, Denton, MD 21629

  Wake up to sunrise on the Choptank River and wind down with some of the most stunning sunsets on the Eastern Shore — with Ospreys, Eagles, Herons, and an abundance of wildlife as your daily backdrop. This stunning 4,853 sq ft waterfront estate sits on 2.44 acres with 268 feet of private river frontage, putting you right on the water and just steps from the best of historic downtown Denton. Built

  

  Elizabeth Osborn

  Coldwell Banker Realty

  322 S 2nd St, Denton, MD 21629
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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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  /24

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  11139 Central Ave, Ridgely, MD 21660

  Welcome to 11139 Central Avenue, where the tranquility of country living meets the convenience of a prime Caroline County location. Nestled on one acre outside Ridgely, this updated 3 bed 2 bath rancher offers space, functionality, and modern updates. The open concept layout is great for entertaining, while the 30 x 50 shop shines for those who need serious workspace, storage, or just a big

  

  BJ Kilby

  Eastern Shore Real Estate, LLC

  11139 Central Ave, Ridgely, MD 21660
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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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  /48

  $374,900

  • 4 Beds
  • 2.5 Baths
  • 2,176 Sq Ft

  8548 Dogwood Blossom Ln, Denton, MD 21629

  Nestled along a private road in a peaceful, tucked-away setting, this well-maintained Colonial offers the perfect blend of privacy, space, and convenience. Situated on more than 1.2 acres, the property backs to mature woods, providing beautiful wooded views and a serene backdrop to everyday living. The home needs only minor cosmetic updates, making it an excellent opportunity to add your own

  Barbara McCaffrey Redfin Corp

  8548 Dogwood Blossom Ln, Denton, MD 21629
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  /49

  $315,000

  Open House 8/15

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

  111 Maple Ave, Greensboro, MD 21639

  Step into the timeless charm of this beautifully maintained circa-1880 home, where historic elegance meets thoughtful modern updates. Offering over 2,774 square feet of living space, this exceptional residence features 4 spacious bedrooms, 2 full bathrooms, and an abundance of original architectural character that has been lovingly preserved while incorporating today's modern conveniences. From

  Barbara McCaffrey Redfin Corp

  111 Maple Ave, Greensboro, MD 21639
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  /41

  $579,900

  Open Sat 11AM - 1PM $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
• 

  

  /22

  $467,900

  • 3 Beds
  • 4 Baths
  • 2,713 Sq Ft

  202 N Central Ave, Ridgely, MD 21660

  Charming Victorian home in the heart of Ridgely, ideally situated on a picturesque, tree-shaded corner lot. This timeless property offers classic character, curb appeal, and a prime location close to local amenities. An expansive wraparound front porch sets the stage for this beautiful home, featuring a gracious entryway, stunning columned foyer, and gleaming hardwood floors that enhance its

  Marcia Rostien Long & Foster Real Estate, Inc.

  202 N Central Ave, Ridgely, MD 21660
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  /47

  $425,000

  • 3 Beds
  • 1.5 Baths
  • 1,356 Sq Ft

  21370 Skeleton Creek Rd, Preston, MD 21655

  Very rustic and private 3 bedroom, 1 and a 1/2 bath log cabin on 15 private wooded acres. There is a large building and a sun porch overlooking a stream running through the property. Excellent hunting property for whitetail deer and turkey!

  Henry Gibbons-Neff Meredith Fine Properties

  21370 Skeleton Creek Rd, Preston, MD 21655
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  /32

  $615,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,834 Sq Ft

  28402 Liden School Rd, Denton, MD 21629

  This is the one! Approx. 16.77 acres with an owner built 3 bedroom home. One acre with home plus additional acreage. Some acreage is wooded with wild life including, but not limited to, rabbit, deer, and turkey. This home has magnificent kitchen with custom cabinetry and SS appliances, including a 5 burner stove and double wall oven. Pellet stove is included for those cool evenings and damp days.

  Michael Shipley Benson & Mangold, LLC.

  28402 Liden School Rd, Denton, MD 21629
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  /2

  $210,000

  $50K 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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  /85

  $769,000

  $106K PRICE DROP

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

  3547 Prchal Rd, Preston, MD 21655

  **Don't Miss This Rare Opportunity**Pride of ownership shines throughout this beautifully appointed home, featuring 3 bedrooms, a bonus room, 3 full bathrooms, a dedicated office space and much more- set on over 4 serene acres. This property includes approximately 2.5 wooded acres with private walking trails and an abundance of wildlife. Major 2025 home improvements including a brand new

  Amy Endzel Keller Williams Select Realtors of Annapolis

  3547 Prchal Rd, Preston, MD 21655
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  /4

  $200,000

  • 3 Beds
  • 1 Bath
  • 2,020 Sq Ft

  22971 Tuckahoe Springs Dr, Denton, MD 21629

  Ranch style home situated on a 1.18 acre lot. There is no access to the interior of the home. Priced below assessed value, home to be transferred occupied, as-is. Please do not disturb the occupants.

  Michael Johnson Marathon Real Estate

  22971 Tuckahoe Springs Dr, Denton, MD 21629
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  /25

  $325,000

  • 4 Beds
  • 2 Baths
  • 1,539 Sq Ft

  306 Sunrise Ave, Ridgely, MD 21660

  Charming & Move-In Ready in Ridgely! This 4-bedroom, 2-full-bath home is priced to sell and ready for its next owner. New $25,000 roof with 50-year transferable warranty! Situated on a spacious corner lot in the friendly town of Ridgely, MD, the property includes 2 utility sheds for extra storage and plenty of parking with off-street spaces in both the front and rear, plus additional on-street

  Vincent De Lorenzo Samson Properties

  306 Sunrise Ave, Ridgely, MD 21660
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  /47

  $644,995

  • 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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  /58

  $620,000

  • 4 Beds
  • 2.5 Baths
  • 2,704 Sq Ft

  16881 Heritage Hills Ln, Henderson, MD 21640

  Privacy, space, and endless possibilities — this 5.06-acre retreat offers the lifestyle you've been looking for. Tucked into a partially wooded setting at the end of a quiet drive, 16881 Heritage Hills Ln provides the perfect blend of seclusion, functionality, and room to grow. Best of all, there's no HOA, giving you the freedom to truly enjoy your property. Built in 2005, the home offers 2,704

  Kaitlyn Collins Benson & Mangold, LLC

  16881 Heritage Hills Ln, Henderson, MD 21640
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  /14

  $110,000

  $40K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 640 Sq Ft

  26471 Three Bridges Rd, Federalsburg, MD 21632

  **Back Active at no fault of the seller**Opportunity awaits at 26471 Three Bridges Rd in Federalsburg, MD! This partially remodeled 2-bedroom, 2-bath home is ready for your finishing touch. Inside, the property has been taken down to the framing and subflooring, giving you a true blank canvas to bring your vision to life—whether you’re an investor looking for your next project or a buyer ready to

  LEE MARLAND Keller Williams Realty

  26471 Three Bridges Rd, Federalsburg, MD 21632
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  /28

  $699,000

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  14540 Drapers Mill Rd, Goldsboro, MD 21636

  Searching for your own private oasis with endless possibilities? Welcome to a rare 16.29-acre offering made up of four separate parcels, thoughtfully improved and ready for whatever vision you bring. Whether you dream of a hobby farm, a multi-use homestead, or a private retreat, this property delivers space, versatility, and infrastructure you won’t find anywhere else. Across the acreage you’ll

  Amanda Morgan Brenton Realty Group

  14540 Drapers Mill Rd, Goldsboro, MD 21636
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  /47

  $509,900

  • 4 Beds
  • 3.5 Baths
  • 2,231 Sq Ft

  14631 Fox Chase Cir, Ridgely, MD 21660

  OPEN House this Saturday Aug. 1, 3:30-5:30pm! Welcome home to your own private country paradise. Nestled on 2.43 peaceful acres, this beautifully renovated log cabin blends rustic charm with modern comfort. Designed to impress, the home features both a main-level primary suite and a spacious second-floor primary suite, offering exceptional flexibility for family or guests. Thoughtfully updated

  Rick Parreco RE/MAX Executive

  14631 Fox Chase Cir, Ridgely, MD 21660
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  /2

  $95,000

  • 3 Beds
  • 1.5 Baths
  • 1,408 Sq Ft

  310 E Central Ave, Federalsburg, MD 21632

  Excellent investment opportunity! Over 1/4 acre lot. Home needs TLC. Partial owner financing available. Call for more info. This deal will not last long. Grab it while you have the chance!

  Raphael Szendro R&R Executive Realty

  310 E Central Ave, Federalsburg, MD 21632
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  /29

  $299,000

  $40K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 2,017 Sq Ft

  211 Bloomingdale Ave, Federalsburg, MD 21632

  Welcome to 211 Bloomingdale Ave. This custom‐built Brick Williamsburg‐style colonial showcases true craftsmanship, featuring beautiful hardwood floors throughout, custom built‐ins, and detailed moldings. The spacious living room offers an inviting wood‐burning fireplace, while the large great room with its vaulted ceiling provides flexible living space and could easily be converted into a third

  Jana Meredith Meredith Fine Properties

  211 Bloomingdale Ave, Federalsburg, MD 21632
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  /8

  $239,900

  New Construction

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

  205 Park Ave, Federalsburg, MD 21632

  **Construction has not yet began, please feel free to drive by the lot. Completion will be for this August 2026!!*** 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.

  Erene Katris Coldwell Banker Realty

  205 Park Ave, Federalsburg, MD 21632
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  /30

  $275,000

  $5K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft

  504 Sunset Blvd, Ridgely, MD 21660

  ***Price Improvement *** This delightful 3-bedroom bungalow offers a perfect blend of comfort and community. Built in 1940, this home exudes character with its sturdy block construction and inviting layout. The cozy 864 sq. ft. interior is complemented by essential appliances, including a refrigerator, stove, washer, and dryer, making daily living a breeze. The generous half-acre lot provides

  Cheryl Knotts Chesapeake Real Estate Associates, LLC

  504 Sunset Blvd, Ridgely, MD 21660
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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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  /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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  /74

  $479,000

  • 3 Beds
  • 3 Baths
  • 2,506 Sq Ft

  104 Charlotte Ave, Federalsburg, MD 21632

  Custom Brick Rancher with 2500 sq ft of living space sitting on over half an acre just outside of downtown Federalsburg overlooking Chambers Park is waiting for you to come see to appreciate. Owners have done many improvements and upgrades to the property, but left some of it's timeless charm. New carpet has been installed on the porch, breakfast nook, and family room July 2026, new windows 2026,

  Shelby Roney Benson & Mangold, LLC

  104 Charlotte Ave, Federalsburg, MD 21632
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  /24

  $294,990

  New Construction

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

  Sullivan Plan at Kinnamon Meadows, Greensboro, MD 21639

  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 visitors. The open-concept kitchen boasts stainless steel appliances, modern cabinetry, and an optional island with seating that is perfect for casual

  D.R. Horton Builder

  103 Park Ave Unit 36203275, Greensboro, MD 21639
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  /45

  $319,999

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,079 Sq Ft

  129 Bloomingdale Ave, Federalsburg, MD 21632

  Welcome home to this beautifully updated 3-bedroom, 2-bath ranch offering over 2,000 square feet of comfortable living space. Thoughtfully improved throughout, this home features stylish board-and-batten accents, quartz countertops, and a functional layout designed for everyday living and entertaining. Enjoy generous-sized bedrooms, a spacious second living area, and plenty of room to spread out.

  Beverly Brown Coldwell Banker Realty

  129 Bloomingdale Ave, Federalsburg, MD 21632
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  /39

  $349,900

  • 3 Beds
  • 2 Baths
  • 1,414 Sq Ft

  504 Main St, Goldsboro, MD 21636

  Welcome to this turn-key, eco-friendly rancher offering single-level living and a modern, open layout. Step inside to a fluid floor plan featuring striking dark wood-look laminate flooring throughout. The spacious living room features a designer green accent wall and flows seamlessly into the country kitchen and dining combination. The kitchen boasts sleek white cabinetry, stainless steel

  Dustin Parker The Parker Group

  504 Main St, Goldsboro, MD 21636
• 

  

  /23

  $285,000

  $24K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  505 Maryland Ave, Ridgely, MD 21660

  Welcome to 505 Maryland Ave in the heart of charming Ridgely! This beautifully remodeled 3-bedroom, 2-bath rancher is truly move-in ready and offers the perfect blend of modern updates and everyday comfort. Renovated just a few years ago, the home features luxury vinyl plank flooring throughout, stylish soft-close cabinetry, granite countertops, stainless steel appliances, and a bright,

  Heather Brummell Keller Williams Realty

  505 Maryland Ave, Ridgely, MD 21660
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  /59

  $465,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,038 Sq Ft

  27329 Iron Gate Rd, Federalsburg, MD 21632

  Charming Colonial-style farmhouse set on 9 scenic acres, offering a rare blend of historic character, pastoral beauty, and endless potential. Ideal for animal lovers or those seeking a peaceful weekend retreat, the home features hardwood floors, exposed ceiling beams, and three wood-burning stoves that add warmth and timeless appeal. Large Spacious bedrooms, a screened porch and rear patio

  Shannon Parker Keller Williams Select Realtors of Cambridge

  27329 Iron Gate Rd, Federalsburg, MD 21632
• 

  

  /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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  /33

  $340,000

  $29K PRICE DROP

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

  401 S 2nd St, Denton, MD 21629

  This charming 2-story colonial home in Denton offers a perfect blend of classic character and modern updates. Featuring 3 bedrooms and 11⁄2 bathrooms, this well-maintained home is conveniently located close to downtown, giving you easy access to local restaurants, shopping, and community events. Inside, you’ll find beautiful hardwood floors that add warmth and timeless appeal throughout much of

  Wes Russum Coldwell Banker Chesapeake Real Estate Company

  401 S 2nd St, Denton, MD 21629
• 

  

  /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

  Alicia Gannon Dulin Benson & Mangold, LLC

  208 Oriole Ave, Ridgely, MD 21660
• 

  

  /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
• 

  

  /23

  $224,000

  $6K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,828 Sq Ft

  126 Maple Ave, Preston, MD 21655

  Step back in time with this early 1900s home. This home is full of character, from the detail in the trim work to the upper level 'porch.' This home offers great potential to be returned to the early 1900s with a little TLC and vision. Located in the heart of Preston, it is 15 minutes from historic Easton with all its amenities. Come take a look and see the vision.

  Marsha Tull Marshy Hope Realty LLC

  126 Maple Ave, Preston, MD 21655
• 

  

  /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 luxury vinyl

  Justin Pokrywka Taylor Properties

  25485 Hignutt Rd, Denton, MD 21629

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