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Homes for Sale near Colonel Richardson Middle School

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  • /35

    $361,000

    • 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

    Agent Photo

    Rosezette Dennis

    Coldwell Banker Realty

    (410) 705-7651

    206 Charles St, Federalsburg, MD 21632
  • /71

    $500,000

    • 4 Beds
    • 2 Baths
    • 1,986 Sq Ft

    25699 Auction Rd, Federalsburg, MD 21632

    ***BUYER WALKED AWAY!!****Mortgage savings may be available for buyers of this home.Opportunity to purchase a working farm with remodeled residence - from new luxury vinyl plank flooring and Advantech subfloors to a fully replaced middle beam for lasting structural integrity. Nearly all windows and doors are brand new, the heating system has been upgraded to an efficient heat pump, and

    Barbara McCaffrey Redfin Corp

    25699 Auction Rd, Federalsburg, MD 21632
  • /54

    $549,000

    • 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
  • /35

    $279,000

    • 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
  • /43

    $440,000

    • 4 Beds
    • 3 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 4-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
  • /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
  • /100

    $319,900

    • 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
  • /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
  • /41

    $289,900

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

    306 S Main St, Federalsburg, MD 21632

    Step into timeless charm and modern comfort with this beautifully maintained -move in ready!-2,820 sq ft Victorian home, featuring 4 spacious bedrooms (freshly painted) and 1.5 baths. Nestled along the tranquil Marshyhope Creek, this waterfront retreat offers peaceful views and the rare opportunity to fish or kayak directly from your own private shoreline.Start your mornings with coffee on

    Mary Mabry Keller Williams Select Realtors of Cambridge

    306 S Main St, Federalsburg, MD 21632
  • /56

    $320,000

    • 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

    Ross Muir EXP Realty, LLC

    212 Main St, Preston, MD 21655
  • /10

    $299,900

    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft

    21090 Marsh Creek Rd, Preston, MD 21655

    Amazing opportunity for a 1st time buyer or investor. The home has been recently renovated to include new kitchen cabinets, counter tops, appliances, flooring, ceiling fans, base board heating units, new windows and painting. The roof was replaced in 2024. The home is move in ready, just bring your furniture.

    Eddie Matthews Benson & Mangold, LLC

    21090 Marsh Creek Rd, Preston, MD 21655
  • /57

    $529,000

    • 4 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    7837 Shore Dr, Preston, MD 21655

    Two Johns – Charming Home in a Sought-After Waterfront CommunityNestled between Preston and Denton in the desirable Two Johns subdivision, this beautifully maintained 4-bedroom, 2.5-bath home offers a rare blend of comfort, style, and location. Just a few houses away from the public boat landing, residents enjoy easy water access for boating, kayaking, or fishing. Take in serene water

    Eddie Matthews Benson & Mangold, LLC

    7837 Shore Dr, Preston, MD 21655
  • /29

    $750,000

    • 3 Beds
    • 2 Baths
    • 1,932 Sq Ft

    7844 Shore Dr, Preston, MD 21655

    Enjoy the waterfront lifestyle with this one floor gem perched up on the banks of the Choptank River just 10 minutes from historic Denton. Relaxation and a connection with nature are easily achieved inside and outside of the home. Outdoor living areas are abundant with a private screened-in gazebo to sit back and enjoy the wildlife, winter deck to catch some rays, and a back patio with Choptank

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    7844 Shore Dr, Preston, MD 21655
  • /14

    $279,000

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

    2697 Choptank Main St, Preston, MD 21655

    Charming Renovated Home in Choptank, Preston MD Additional Photos coming. This home is currently getting a fresh coat of interior paint, new appliances and updates coming. It will be turn key ready for you. Situated on a large double lot with mature landscaping. Don’t miss this beautifully completely renovated 2-bedroom, 2-bath home located in the quaint and peaceful community of

    Darlene Wheatley Benson & Mangold, LLC

    2697 Choptank Main St, Preston, MD 21655
  • /10

    $275,000

    • 3 Beds
    • 3 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 opportunity,

    Samantha Grimes Chesapeake Real Estate Associates, LLC

    21245 Tanyard Rd, Preston, MD 21655
  • /35

    $384,900

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

    22403 Marsh Creek Rd, Preston, MD 21655

    Custom Brick rancher, close to town on large lot. Open floor plan, spacious kitchen, stainless steel appliances, large island. 3 bedrooms, 2 baths, sunroom overlooking yard. New Well and septic being installed. Upgrades include new windows, CAC, new roof new electric service and plumbing

    Barbara Nichols Results Realty Inc.

    22403 Marsh Creek Rd, Preston, MD 21655
  • /17

    $380,000 New Construction

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

    106 Lednum Ave, Preston, MD 21655

    New construction in Preston, MD offering 3 bedrooms and 2 full baths across 1,400 square feet. This home features an open layout with vaulted ceilings, LVP flooring in the main living areas, and carpeted bedrooms. The kitchen is equipped with stainless steel appliances and granite countertops. The primary suite includes a stand-up shower, while the guest bath offers a tub/shower combo. An

    Eric Haro The Parker Group

    106 Lednum Ave, Preston, MD 21655
  • /5

    $300,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    3376 Jefferson Pond Rd, Federalsburg, MD 21632

    This beautifully crafted 3 bedroom, 2 bathroom home offers modern living in a sought-after community with a low annual HOA fee of just $200. Step inside to find luxury vinyl plank flooring throughout the main living areas, a spacious open-concept layout, and a stunning kitchen featuring granite countertops, stainless steel appliances, and plenty of cabinet space. Enjoy peace of mind with a

    Amy Herr Keller Williams Realty

    3376 Jefferson Pond Rd, Federalsburg, MD 21632
  • /6

    $2,999,000

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

    4218 Harmony Rd, Preston, MD 21655

    PROFESSIONAL PHOTOS COMING SOON. CHECK WITH LISTING AGENT FOR MORE DETAILS. A True Eastern Shore Estate! Experience unparalleled living at this magnificent 58+ acre Preston estate, an extraordinary opportunity to own a property that perfectly blends luxury, comfort, and versatility. The stately main residence features 5 bedrooms, 6 full and 3 half baths, and an impressive foyer with a grand

    Donna Harrington Coldwell Banker Realty

    4218 Harmony Rd, Preston, MD 21655
  • /5

    $198,500

    • 3 Beds
    • 1 Bath
    • 1,350 Sq Ft

    6561 Bell Creek Rd, Preston, MD 21655

    Looking for peace, privacy, and wide-open views?Escape the subdivision life — no HOA, no close neighbors, just you and open fields. This charming property, tucked back from the road and surrounded by farmland, has been lovingly held since 1972. Traditional styling and ready for a your new chapter. The home is livable, but will not qualify for USDA, Rural Home or VA. Pinterest, AI and bring

    Barbara Dayton Long & Foster Real Estate, Inc.

    6561 Bell Creek Rd, Preston, MD 21655
  • /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
  • /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
  • /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
  • /14

    $150,000

    • 2 Beds
    • 2 Baths
    • 640 Sq Ft

    26471 Three Bridges Rd, Federalsburg, MD 21632

    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 customize every detail.Set on

    LEE MARLAND Keller Williams Realty

    26471 Three Bridges Rd, Federalsburg, MD 21632
  • /43

    $247,500

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

    207 Bloomingdale Ave, Federalsburg, MD 21632

    Discover this inviting 3-bedroom, 2-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
  • /66

    $479,900

    • 3 Beds
    • 2 Baths
    • 2,400 Sq Ft

    2570 Guard Rd, Federalsburg, MD 21632

    Welcome to this 3-bedroom, 2-bathroom home nestled on more than Eight acres of land, offering the perfect blend of comfort, space, and opportunity. The main level features a practical layout with three bedrooms, two full baths, and a warm, inviting living space. Upstairs, you’ll find an unfinished second story, a blank slate ideal for adding extra bedrooms, a bonus room, or a private retreat

    Thomas Burdett Keller Williams Realty

    2570 Guard Rd, Federalsburg, MD 21632
  • /34

    $245,000

    • 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
  • /18

    $99,000

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

    215 Academy Ave, Federalsburg, MD 21632

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

    Nora Turner Long & Foster Real Estate, Inc.

    215 Academy Ave, Federalsburg, MD 21632
  • /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
  • /89

    $2,750,000

    • 4 Beds
    • 4.5 Baths
    • 6,520 Sq Ft

    28219 Bridgeville Rd, Federalsburg, MD 21632

    First time on the market! Discover a rare opportunity to own a 105± acre estate on Maryland’s beautiful Eastern Shore, Close to tax free shopping and the beaches. Designed by renowned California architect David Watson, the exterior of this home is one of the all-time most downloaded photos on the popular homebuilding and design website, Houzz. This one-of-a-kind property combines luxury living,

    Jim Corson Benson & Mangold, LLC

    28219 Bridgeville Rd, Federalsburg, MD 21632
  • /4

    $24,500

    • 2 Beds
    • 1 Bath
    • 1,024 Sq Ft

    204 Academy Ave, Federalsburg, MD 21632

    Investor special! This property is being sold AS-IS and is priced for land value or a full renovation. The existing structure requires extensive repairs or complete tear-down—ideal for experienced builders, contractors, or savvy investors looking for a project. Buyer to verify zoning, permits, potential use. Buyer Broker/Agent and/or Buyer must do their own due diligence to verify if the existing

    Mike Dunn Keller Williams Realty Delmarva

    204 Academy Ave, Federalsburg, MD 21632
  • /3

    $30,000

    • Land
    • 0.5 Acre
    • $60,000 per Acre

    0 Gadow Rd, 4, Preston, MD 21655

    Tucked away in the heart of Caroline County, this 1⁄2-acre parcel of raw land in Preston, Maryland offers an affordable opportunity to create your perfect escape or future investment. Whether you're dreaming of a peaceful rural retreat, a new build, or simply a spot to call your own, this lot is a blank canvas full of potential. Why Preston? Living in Preston means enjoying a small-town, rural

    Lisa Longest Realty Navigator

    0 Gadow Rd, 4, Preston, MD 21655
  • /22

    $525,000

    • Land
    • 63.16 Acres
    • $8,312 per Acre

    0 Dover Bridge Rd Unit MDCM2005586, Preston, MD 21655

    Dover Bridge Road | Preston, MarylandThis 63 ± acre parcel on Dover Bridge Road offers a rare opportunity to own a sizeable tract of woodland conveniently located just four miles from Preston, seven and a half miles from Easton, and about fifteen minutes from Route 50.The property is perc-approved for residential use and includes a forestry management plan documenting that roughly 58

    Coard Benson Benson & Mangold, LLC

    0 Dover Bridge Rd Unit MDCM2005586, Preston, MD 21655
  • /2

    $49,900

    • Land
    • 1.92 Acres
    • $25,990 per Acre

    5735 Reliance Rd, Rhodesdale, MD 21659

    Wooded country lot waiting to be your next home site.

    Sean Steward Century 21 Home Team Realty

    5735 Reliance Rd, Rhodesdale, MD 21659
  • /25

    $125,000

    • 2,168 Sq Ft

    28035 Possum Hill Rd, Federalsburg, MD 21632

    Prime Half-Acre Lot Near Smithville Lake – Cleared, with Well and Oversized Garage BayThis unique 0.48-acre property on Possum Hill Rd is ideally situated less than a mile west of the Maryland-Delaware state line, offering a rare combination of open space, infrastructure, and development potential.Property Highlights:Cleared Lot with Existing Well – The land has already been cleared

    Sam Benkirane Proplocate Realty, LLC

    28035 Possum Hill Rd, Federalsburg, MD 21632
  • /3

    $25,000

    • 728 Sq Ft

    23547 Jonestown Ln, Preston, MD 21655

    Build your dream home on this available lot in Preston, Md. Old home on property - either tear down or restore. Buyer to complete due diligence with County

    Dalton Adshead Keller Williams Select Realtors of Cambridge

    23547 Jonestown Ln, Preston, MD 21655
  • /2

    $129,000

    • 6 Beds
    • 2 Baths
    • 2,400 Sq Ft

    321 S Main St, Federalsburg, MD 21632

    tenant occupied duplex rented for 1600/ month. agent is owner

    Bo Claggett Coldwell Banker Realty

    321 S Main St, Federalsburg, MD 21632
  • /10

    $48,999

    • Land
    • 0.24 Acre
    • $204,162 per Acre

    0 Brooklyn Ave, Federalsburg, MD 21632

    Taylor McCartney VRA Realty

    0 Brooklyn Ave, Federalsburg, MD 21632
  • /4

    $92,000

    • Land
    • 0.33 Acre
    • $278,788 per Acre

    162 Main St, Preston, MD 21655

    Anne Schmidt Long & Foster Real Estate, Inc.

    162 Main St, Preston, MD 21655
  • /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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