Caroline County MD Homes under $300,000

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  /2

  $245,000

  • 3 Beds
  • 1 Bath
  • 1,190 Sq Ft

  210 Caroline Ave, Ridgely, MD 21660

  Welcome to 210 Caroline Avenue – a delightful farmhouse full of charm, right in the heart of Ridgely, MD! This 3-bedroom, 1-bath home blends classic character with thoughtful updates. Recent improvements include energy-efficient mini-split systems for year-round comfort and a brand-new back deck—ideal for morning coffee or evening gatherings. Situated on a spacious corner lot, this property

  

  Linda Moran

  Berkshire Hathaway HomeServices PenFed Realty-WOC

  (410) 698-1579

  210 Caroline Ave, Ridgely, MD 21660
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  /35

  $299,999

  • 3 Beds
  • 2 Baths
  • 1,448 Sq Ft

  113 Maple Ave, Goldsboro, MD 21636

  Welcome to 113 Maple Avenue, GoldsboroStep into comfort and convenience with this updated home in the heart of Goldsboro. Inside this 3 bedroom, 2 full bath property, you’ll find a fresh look with brand-new countertops, a new refrigerator, and a new washer and dryer. Major updates have already been taken care of, including a new hot water heater, new HVAC system, and new well pump—giving

  Shawn Moore Meredith Fine Properties

  113 Maple Ave, Goldsboro, MD 21636
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  /57

  $300,000

  • 3 Beds
  • 2 Baths
  • 1,104 Sq Ft

  122 Mill St, Greensboro, MD 21639

  Wow!!! Huge price reduction- priced to sell-* Be sure to click the link for the interactive floor plan*Like New Construction! This beautifully renovated 3-bedroom, 2-full bath rancher is move-in ready and shines throughout. Featuring a brand-new kitchen with modern finishes, updated bathrooms, fresh flooring, paint, roof and a new HVAC system, this home truly has it all. The open and

  Carolyn Buchleitner Long & Foster Real Estate, Inc.

  122 Mill St, Greensboro, MD 21639
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  /6

  $279,000

  • 2 Beds
  • 2 Baths
  • 1,104 Sq Ft

  2697 Choptank Main St, Preston, MD 21655

  Charming Renovated Home in Choptank, Preston MD Situated on a large double lot with mature landscaping. Don’t miss this beautifully renovated 2-bedroom, 2-bath home located in the quaint and peaceful community of Choptank. Every inch of this home has been thoughtfully updated from top to bottom, blending modern finishes with classic Eastern Shore charm.Currently tenant-occupied and

  Darlene Wheatley Benson & Mangold, LLC

  2697 Choptank Main St, Preston, MD 21655
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  /28

  $299,000 Open Sat 11AM - 1PM

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

  113 Chambers St, Preston, MD 21655

  Welcome to the quiet quaint town of Preston, MD, just outside of Easton and a short drive to the Famous Suicide Bridge Restaurant! This will not last long! Schedule your showing today!This 3 bedroom two bathroom rancher sits on .42 acres that is fenced in! Rear deck, large detached garage that is temperature controlled, plumbing, electric and plenty of space to park your car and still

  Amy Betts Coldwell Banker Realty

  113 Chambers St, Preston, MD 21655
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  /25

  $279,000

  • 4 Beds
  • 1.5 Baths
  • 1,670 Sq Ft

  317 W Central Ave, Federalsburg, MD 21632

  Newly renovated 4 bedroom, 1.5 bath. Large back yard with large shed and mostly new fence. New central heat and air, new roof, new flooring and paint throughout; new kitchen appliances; new countertop and sink; new hot water heater. Large basement with two extra storage rooms. Home still retains many original features, lovely molding and stair, great back yard; good condition. Listing Agent is

  Kelly Sharpless Kelstar Properties

  317 W Central Ave, Federalsburg, MD 21632
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  /72

  $285,000

  • 2 Beds
  • 2 Baths
  • 2,048 Sq Ft

  115 Maple Ave, Goldsboro, MD 21636

  Step into this beautifully renovated Victorian home, nestled on a generous .55-acre lot. This 2048 sqft gem blends timeless architectural charm with contemporary updates, offering a perfect blend of classic style and modern comfort.The home features three spacious bedrooms on the second floor, complemented by two full bathrooms—one on each level. The freshly painted interior, along with

  Phill Whitby Long & Foster Real Estate, Inc.

  115 Maple Ave, Goldsboro, MD 21636
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  /10

  $275,000

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

  21245 Tanyard Rd, Preston, MD 21655

  Charming Country Living with Room to Make It Your Own!Welcome to 21245 Tanyard Road, a spacious rancher with 3 bedrooms and 2 full baths nestled on a peaceful 0.62-acre lot in Preston. Built in 1987, this single-level home offers a solid foundation and a functional layout, ready for your personal touch and updates.Whether you're looking for a primary residence or an investment

  Samantha Grimes Chesapeake Real Estate Associates, LLC

  21245 Tanyard Rd, Preston, MD 21655
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  /32

  $289,000

  • 3 Beds
  • 1 Bath
  • 1,392 Sq Ft

  6101 Bethlehem Rd, Preston, MD 21655

  Charming 3-bedroom, 1-bathroom mobile home on 1.37 acres with plenty of room to grow! This well-maintained, one-family-owned property boasts numerous recent upgrades, 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 provides ample storage or workspace.

  Katie Moore Coldwell Banker Chesapeake Real Estate Company

  6101 Bethlehem Rd, Preston, MD 21655
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  /29

  $279,000 New Construction

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

  1105 Market St, Denton, MD 21629

  One Level Living! Nothing to do but Move-in! Home built in 2022. Home features Large Open Floor Plan, Kitchen Dining Combo with Breakfast Bar. Spacious Family Room. Primary Bedroom has two nice size closets an additional walk-in closet inside primary Bathroom w/ Double sinks and a Walk-in Shower! 2 other bedrooms are nice size. Full Bath in the Hall with Tub. Seperate laundry Room w shelving.

  Kathleen Brenton Brenton Realty Group

  1105 Market St, Denton, MD 21629
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  /2

  $277,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,182 Sq Ft

  123 Parkland Rd, Greensboro, MD 21639

  Explore 123 Parkland Road, a new home under-construction in the quaint Kinnamon Meadows community of Greensboro, MD. The Curtis is a 1,182 square foot, cottage-style ranch home with three bedrooms and two bathrooms. As you enter the home through the front porch, this thoughtfully designed home has a grand open concept living area that leads into the spacious kitchen. To the right, a long,

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

  123 Parkland Rd, Greensboro, MD 21639
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  /3

  $276,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,182 Sq Ft

  CURTIS Plan at Kinnamon Meadows, Greensboro, MD 21639

  The Curtis is a 1,182 square foot, cottage-style ranch home with three bedrooms and two bathrooms. As you enter the home through the front porch, this thoughtfully designed home has a grand open concept living area that leads into the spacious kitchen. To the right, a long, main hallway allows for the two guest bedrooms and guest bathroom to be separate from the living areas of the home. Along

  

  D.R. Horton

  Builder

  103 Park Ave Unit 36203276, Greensboro, MD 21639
• 

  $279,990 New Construction

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

  113 Parkland Rd, Greensboro, MD 21639

  Welcome to 113 Parkland Road, a new home under-construction in Kinnamon Meadows in Greensboro, MD. 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

  

  D.R. Horton

  Builder

  113 Parkland Rd, Greensboro, MD 21639
• 

  $277,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,182 Sq Ft

  123 Park Ave, Greensboro, MD 21639

  Explore 123 Parkland Road, a new home under-construction in the quaint Kinnamon Meadows community of Greensboro, MD. The Curtis is a 1,182 square foot, cottage-style ranch home with three bedrooms and two bathrooms. As you enter the home through the front porch, this thoughtfully designed home has a grand open concept living area that leads into the spacious kitchen. To the right, a long, main

  

  D.R. Horton

  Builder

  123 Park Ave, Greensboro, MD 21639
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  /9

  $219,000

  • Studio
  • 1,744 Sq Ft

  328 N Main St, Federalsburg, MD 21632

  Investment Opportunity – Duplex with Strong Rental History!Don’t miss this chance to own a well-maintained duplex offering two separate rental units with a proven track record of income. Priced at just $219,000, this property is ideal for investors seeking steady cash flow or those looking to live in one unit and rent the other.Each unit offers comfortable living space and is

  Jeff Kemp EXP Realty, LLC

  328 N Main St, Federalsburg, MD 21632
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  /16

  $215,000

  • 2 Beds
  • 1 Bath
  • 640 Sq Ft

  522 Lincoln St, Denton, MD 21629

  Coming Soon! Downtown Charm Meets Cozy Comfort Step into this delightful downtown bungalow—move-in ready and brimming with character. Featuring 2 spacious bedrooms, 1 full bathroom, a welcoming living area, and a functional galley kitchen, this home offers the perfect blend of simplicity and style.Start your mornings on the cozy front porch, ideal for sipping coffee and watching the world

  Amanda Morgan Brenton Realty Group

  522 Lincoln St, Denton, MD 21629
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  /43

  $245,000

  • 3 Beds
  • 2 Baths
  • 1,684 Sq Ft

  207 Bloomingdale Ave, Federalsburg, MD 21632

  Discover this inviting 2-bedroom, 1-bath home on a 0.27-acre lot in the heart of Federalsburg. Enter to a spacious living room filled with natural light and a cozy fireplace, perfect for relaxing or entertaining. Adjacent, the family room features stunning wood-paneled walls, built-in shelving, a second fireplace, and access to both the outdoors and the kitchen and dining areas, creating a

  Dustin Parker The Parker Group

  207 Bloomingdale Ave, Federalsburg, MD 21632
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  /60

  $227,900

  • 3 Beds
  • 1.5 Baths
  • 1,565 Sq Ft

  206 N Academy St, Greensboro, MD 21639

  Seller offering $5,000 in closing cost assistance with acceptable offer!Welcome home to this charming 3-bedroom, 1.5-bath colonial in the heart of Greensboro—just a short walk to Ober Park. Step inside to find beautifully updated bathrooms, new LVP flooring on the main level and in the baths, and fresh paint throughout. The kitchen is in the process of receiving brand-new cabinets, a

  Heather Branham The Parker Group

  206 N Academy St, Greensboro, MD 21639
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  /25

  $265,900

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

  113 Boyce Mill Rd, Greensboro, MD 21639

  Enjoy the convenience of the short distance to jump onto 313 , yet a quiet location away tucked in the country side. House built in 2007 this well maintained home is waiting for the next owner. Open floor plan, the kitchen has ample room to be an eat in kitchen. Enter the home and you walk into the living room off the front porch. All living on one level makes this an easy home to navigate.

  Kat Thompson Benson & Mangold, LLC.

  113 Boyce Mill Rd, Greensboro, MD 21639
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  /34

  $265,000

  • 3 Beds
  • 2 Baths
  • 1,840 Sq Ft

  158 Wright St, Preston, MD 21655

  Step back in time with this charming 3-bedroom, 2-bathroom home built in 1890, located in the heart of Preston. Full of character and original details, this home offers a unique opportunity to restore and customize a piece of local history. The inviting living room features a cozy fireplace, perfect for relaxing evenings. A large laundry room and a separate den/office provide flexibility and

  Wes Russum Coldwell Banker Chesapeake Real Estate Company

  158 Wright St, Preston, MD 21655
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  /13

  $240,000

  • 3 Beds
  • 2.5 Baths
  • 1,753 Sq Ft

  1202 Blue Heron Dr, Denton, MD 21629

  WELCOME HOME!!! 1753 SQ FT OF COMFORT...... 3 FLOORS, 3 SPACIOUS BEDROOMS, 3 BATHROOMS, WHITE WOOD CABINETS, MARBLE COUNTERTOPS, STAINLESS STEEL APPLIANCES, LUXURY VINYL FLOORING DOWNSTAIRS, FULLY CARPETED UPSTAIRS, LAUNDRY ROOM, PANTRY AND MORE. CORNER LOT/ QUICK ENTRY & EXIT/ PLAYGROUND/ POOL / CLUBHOUSE/ PET FRIENDLY NEIGHBORHOOD/ HOA / CLOSE DRIVE TO SCHOOLS, STORES, OCEAN CITY,

  SHANTA PHILLIPS EXP Realty, LLC

  1202 Blue Heron Dr, Denton, MD 21629
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  /21

  $269,000

  • 3 Beds
  • 1 Bath
  • 1,019 Sq Ft

  529 N 6th St, Denton, MD 21629

  Welcome to this beautifully maintained 3 bedroom, 1 bath home that blends classic character with modern updates. Inside, you’ll find original hardwood floors that add warmth and charm throughout the living space.Enjoy a spacious backyard perfect for entertaining or relaxing, plus a brand new oversized back deck completed in 2025, ideal for outdoor gatherings. The home also features new

  Cody Weese Weese Properties, LLC

  529 N 6th St, Denton, MD 21629
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  /44

  $225,000

  • 4 Beds
  • 2 Baths
  • 2,884 Sq Ft

  148 Main St, Preston, MD 21655

  Welcome to this timeless 1880 Federal style House, where historic charm meets thoughtful modern updates. Situated on a serene and spacious lot dotted with beautiful mature fruit trees, this 4 bedroom, 2 bath home offers approximately 2800 sq ft of character-filled space. Many renovations have already been completed- preserving original architectural details while adding essential modern

  Cheri Bruce-Phipps TTR Sotheby's International Realty

  148 Main St, Preston, MD 21655
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  /30

  $269,000

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

  312 Fountain Ave, Denton, MD 21629

  **100% Financing/NO MONEY DOWN eligible property with a USDA Loan (check with your Lender to confirm)** Charming in-town living in this 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

  Pamela Ackermann-Doll RE/MAX Executive

  312 Fountain Ave, Denton, MD 21629
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  /25

  $289,000

  • 4 Beds
  • 3.5 Baths
  • 2,640 Sq Ft

  1904 Blue Heron Dr, Denton, MD 21629

  Welcome to Mallard Landing and your own private townhouse in the quiet, peaceful outskirts of Denton. This charming 2,640 sq ft townhouse offers thoughtfully designed living space, including four spacious bedrooms, four bathrooms, a bar-counter dine-in kitchen, and a formal dining room. As you step inside the front door, you’ll notice three levels of spacious room sizes, a walk-in closet in the

  Ralph Harvey ListWithFreedom.com

  1904 Blue Heron Dr, Denton, MD 21629
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  /9

  $269,900

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

  3406 Rose St, Federalsburg, MD 21632

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

  Barbara Nichols Results Realty Inc.

  3406 Rose St, Federalsburg, MD 21632
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  /20

  $230,000

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  218 E Sunset Ave, Greensboro, MD 21639

  Welcome to 218 E Main St Greensboro, MD. This home offers 3 bedrooms and 1 bath. Home has a large, dethatched garage and off-street parking. Located next to the public boat ramp, with easy access to local shopping and Delaware tax free shopping. This home is located in a flood zone and is being sold as is. Sellers are offering $5,000 in closing assistance with acceptable offer!

  Dawn Williams Berkshire Hathaway Homeservice Homesale Realty

  218 E Sunset Ave, Greensboro, MD 21639
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  /10

  $249,000

  • Land
  • 0.23 Acre
  • $1,082,609 per Acre

  520 S 5th Ave, Denton, MD 21629

  LET’S MAKE A DEAL***INVEST IN A PRIME MULTI USE SITE * DESIRABLE LOCATIONS * BUYERS CHOICEDEVELOP NOW? Or HOLD AND LET TIME INCREASE YPUR PROFIT OPPORTUNITY.... FOUR 10,000 SQ FT ADJOINING LOTS IN A GREAT IN TOWN SETTING S DUPLEX. IS ONE OF SEVERAL PERMITTED USES SO EASILY to build total 8 UNITS. Office, Shop or Studio with 2nd floor Residential for a Live Work

  Phil Riordan Meredith Fine Properties

  520 S 5th Ave, Denton, MD 21629
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  /24

  $299,000

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

  505 Maryland Ave, Ridgely, MD 21660

  Welcome to this beautifully updated 3-bedroom, 2-bath rancher located in the charming town of Ridgely, Maryland. Renovated just about two years ago, this home has been lovingly maintained and offers stylish, move-in-ready living with modern finishes throughout. The open-concept kitchen features granite countertops, a spacious island perfect for entertaining, soft-close cabinetry, and

  Kaitlyn Collins Benson & Mangold, LLC

  505 Maryland Ave, Ridgely, MD 21660
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  /25

  $259,000

  • Studio
  • 1,820 Sq Ft

  207 Gay St, Denton, MD 21629

  Price Improvement! Great investment. Perfect opportunity for an investor or owner-occupied duplex as first floor unit generates $1100/month and second floor unit is currently vacant.Conveniently located, multi-family in Downtown Denton with the Denton Police Department directly across the street.Vinyl siding, replacement windows, ductless mini split HVAC and off-street parking in the rear.

  Andrew Beaven Wright Real Estate

  207 Gay St, Denton, MD 21629
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  /17

  $285,000

  • 3 Beds
  • 2 Baths
  • 2,546 Sq Ft

  14706 Cherry Ln, Ridgely, MD 21660

  Are you looking for a diamond in the rough with endless potential at a great price? Here is your opportunity! Make this home shine again and create your own retreat! Leave the stress of every day life behind in this 3 bedrooms, 2 baths rambler with basement, on a beautiful lot and outside of all the hustle and bustle. Come and see for yourself! Hurry! Don't let this one get away! Needs work. Sold

  Ingrid Butler CENTURY 21 New Millennium

  14706 Cherry Ln, Ridgely, MD 21660
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  /8

  $225,000

  • Land
  • 0.06 Acre
  • $3,750,000 per Acre

  245 Briarwood Cir, Denton, MD 21629

  LETS MAKE A DEAL****Hard to Find Great Construction Project waiting for you.Improved 4 adjoining townhouse parcels with concrete slab (check with governmental officials for usability?)Or remove and build new for this special block of 4 town house lots. Beginning of the Sandy Meadows community that is its own block offering privacy outside of crowded downtown for you to Build and sell or

  Phil Riordan Meredith Fine Properties

  245 Briarwood Cir, Denton, MD 21629
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  /8

  $225,000

  • Studio

  245 Briarwood Cir, Denton, MD 21629

  Improved 4 adjoining townhouse parcels with concrete slab (check with governmental officials for usability?)Beginning of the Sandy Meadows community that is its own block offering privacy outside of crowded downtown for you to Build and sell or rent.Listing shows one lotLots 55, 56, 57 & 58 This is a unique opportunity for small project in a nice setting.Call for details.

  Phil Riordan Meredith Fine Properties

  245 Briarwood Cir, Denton, MD 21629
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  /16

  $249,900

  • Land
  • 3.4 Acres
  • $73,500 per Acre

  0 Shore Highway-404 Unit MDCM2004050, Denton, MD 21629

  Farm land or a Home site. Convenient to Denton and 404. 3 parcels totaling 21.11 acres are included in the offering. Tillable land and wooded. Great spot for someone with horses or that wants to hunt. Perk approval on Parcel 83. Approx. 3.7 tillable acreage.

  Eddie Matthews Benson & Mangold, LLC

  0 Shore Highway-404 Unit MDCM2004050, Denton, MD 21629
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  /2

  $230,000

  • Land
  • 16.06 Acres
  • $14,321 per Acre

  11900 Central Ave Central, Ridgely, MD 21660

  This great property offers over 16 acres of level land with frontage on three roads: Central Avenue, Henry Road, and Holly Plains Drive. Zoned R1, this lot presents endless possibilities—whether you're looking to hold, subdivide, or develop. Located just outside the Ridgely city limits and within close proximity to the town center, this property is ideally positioned for future growth. With

  Sam Benkirane Proplocate Realty, LLC

  11900 Central Ave Central, Ridgely, MD 21660
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  /20

  $266,990 New Construction

  • 2 Beds
  • 2 Baths
  • 1,059 Sq Ft

  120 Parkland Rd, Greensboro, MD 21639

  Discover the Perry in Kinnamon Meadows, a 1,059 square foot open concept cottage-style ranch home, offering two bedrooms and two bathrooms at 124 Parkland Road in Greensboro, MD. A welcoming front porch leads you into the spacious living room that seamlessly flows into the kitchen, creating a perfect space for entertaining guests or enjoying family time. The well-equipped kitchen is complete

  

  D.R. Horton

  Builder

  120 Parkland Rd, Greensboro, MD 21639
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  /20

  $294,000 Open Sun 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,420 Sq Ft

  512 Lincoln St, Denton, MD 21629

  Charming Home Near Downtown Denton!Welcome to this beautiful BRAND NEW CONSTRUCTION home near Downtown Denton! 3 Bedrooms, 2 Bathroom home featuring an inviting open concept floor plan perfect for entertaining or everyday living. The kitchen boasts granite countertops, modern cabinetry, and plenty of prep space. A spacious living area flows seamlessly into the dining space,

  Amy Betts Coldwell Banker Realty

  512 Lincoln St, Denton, MD 21629
• 

  /2

  $291,990 New Construction

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

  HELENA Plan at Kinnamon Meadows, Greensboro, MD 21639

  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 home. The oversized great room with an abundance of natural light is open to the kitchen making an ideal space to entertain or

  

  D.R. Horton

  Builder

  103 Park Ave Unit 36203274, Greensboro, MD 21639
• 

  

  /22

  $266,990 New Construction

  • 2 Beds
  • 2 Baths
  • 1,059 Sq Ft

  PERRY Plan at Kinnamon Meadows, Greensboro, MD 21639

  The Perry, a 1,059 square foot open concept cottage-style ranch home, offers two bedrooms and two bathrooms. A welcoming front porch leads you into the spacious living room that seamlessly flows into the kitchen, creating a perfect space for entertaining guests or enjoying family time. The well-equipped kitchen is complete with modern cabinetry, stainless steel appliances, a spacious peninsula

  

  D.R. Horton

  Builder

  103 Park Ave Unit 36203273, Greensboro, MD 21639
• 

  /2

  $286,990 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

  

  D.R. Horton

  Builder

  103 Park Ave Unit 36203275, Greensboro, MD 21639

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