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Homes for Sale near Colonel Richardson High School

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  • /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
  • /46

    $699,000

    • 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. The grounds feature expansive pastures secured by electric fencing, a well-equipped horse barn with stables that measures 36X64, and two convenient run-in sheds.

    Billy Mister Keller Williams Realty

    4757 Long Swamp Rd, Federalsburg, MD 21632
  • /100

    $330,000

    • 3 Beds
    • 1 Bath
    • 1,284 Sq Ft

    2766 Veterans Dr, Federalsburg, MD 21632

    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 topography,

    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
  • /37

    $279,000

    • 3 Beds
    • 1 Bath
    • 1,032 Sq Ft

    22991 Westview Dr, Preston, MD 21655

    Welcome home to this beautifully updated 3-bedroom rancher just minutes from downtown Preston! Move right in and enjoy peace of mind with major updates already done — including a New Roof and Septic (2022), new Well, HVAC, & Electrical panel upgrade (2023). Inside, you’ll find Fresh Paint, New Carpet, a Brand-new Gas range and Refrigerator + New Countertops (2025), and BRIGHT Living Spaces that

    Jennifer Norfolk Coldwell Banker Waterman Realty

    22991 Westview Dr, Preston, MD 21655
  • /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
  • /9

    $299,900

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

    21084 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

    21084 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
  • /39

    $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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /56

    $319,999

    • 3 Beds
    • 2 Baths
    • 2,504 Sq Ft

    135 Kerney St, Federalsburg, MD 21632

    Welcome to this well-maintained home that exudes pride in ownership with just over 2500 square feet of living space. This home boasts upgrades throughout. The kitchen features Granite countertops, stainless steel appliances large island, and a spacious pantry. Large dining room or convert to another living area. Well-appointed bedrooms and a primary with ex large walk-in closet and bathroom. As

    Roger Boyce Chesapeake Real Estate Associates, LLC

    135 Kerney St, Federalsburg, MD 21632
  • /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

    $304,500 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
  • /2

    $299,900 Coming Soon

    • 2 Beds
    • 1.5 Baths
    • 1,700 Sq Ft

    3622 Choptank Rd, Preston, MD 21655

    Listing details and professional photos coming soon!

    Brooke Tephabock VYBE Realty

    3622 Choptank 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

    $220,000

    • 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
  • /21

    $59,900

    • 4 Beds
    • 1 Bath
    • 1,696 Sq Ft

    125 Bloomingdale Ave, Federalsburg, MD 21632

    Attention investors and DIY enthusiasts! Multiple exit strategies: finish this remodel then either flip, rent or move in! Home being sold as is. Cash preferred but will consider financed all offers. Seller is assisted by an Attorney in Fact. Do not knock on door or approach house without prior communication.

    Daniel Demers Sell Your Home Services

    125 Bloomingdale Ave, Federalsburg, MD 21632
  • /22

    $150,000

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

    208 N Main St, Federalsburg, MD 21632

    Coming Soon.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
  • /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
  • /2

    $15,000

    • Land
    • 0.7 Acre
    • $21,429 per Acre

    Parcel 210 Dover Bridge Rd, Preston, MD 21655

    Unimproved lot on Dover Bridge Rd. No perc on the property currently. Close to Easton and Preston. Partially cleared, seller offering to clear remaining tree stumps.

    Katie Stecklair Cross Street Realtors LLC

    Parcel 210 Dover Bridge Rd, Preston, MD 21655
  • /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

    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
  • /51

    $525,000

    • 3 Beds
    • 3.5 Baths
    • 2,667 Sq Ft

    22408 Hog Creek Rd, Preston, MD 21655

    NEW PRICE! Two Tranquil Country Acres with No Restrictions, backs to open farmland. Deep Back Yard includes an above ground pool with a deck for your summer enjoyment, large vinyl fenced area for pets and kids, more fenced area for farm animals (pets) and includes a shooting mound should that be of interest. This lovely home Boasts 2,667 Sq. Ft. of Family Space with new LVP flooring though out

    James Bent Benson & Mangold, LLC

    22408 Hog Creek Rd, Preston, MD 21655
  • /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
  • /4

    $89,000

    • Land
    • 2 Acres
    • $44,500 per Acre

    Lot 1 Clark Canning House Rd, Federalsburg, MD 21632

    Enjoy country living on this nice 2-acre lot that's already perc-approved for a septic system. Just outside the town limits. Minutes away from the town and shopping on the north side and potential job opportunities at the industrial parks on the east side. Already perc-approved. No covenants or restrictions. As you know, large, cleared, building lots near Federalsburg, Maryland, are near

    Mickey Hayward Sunset Properties

    Lot 1 Clark Canning House Rd, Federalsburg, MD 21632
  • /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
  • /16

    $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

    $489,999

    • Land
    • 0.24 Acre
    • $2,041,662 per Acre

    0 Brooklyn Ave, Federalsburg, MD 21632

    Taylor McCartney VRA Realty

    0 Brooklyn Ave, Federalsburg, MD 21632

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