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27944 Possum Hill Rd, Federalsburg
$200,000
2 Beds ⋅ 1 Baths
Offering a peaceful country setting, nearly an acre and a half of land, and a rustic barn with an interesting connection to local history, this two-bedroom, one-bath home in Federalsburg, Maryland, presents an opportunity to enjoy country living with plenty of room to make it your own. The home's casual, comfortable interior features a spacious living room with hardwood flooring and vaulted ceilings that create an open, airy feel. A generously sized country kitchen offers ample room for everyday cooking and connects seamlessly to a large dining area, providing an easy, functional flow between the two spaces. Two nicely sized bedrooms offer comfortable accommodations, while a convenient mudroom and laundry area just off the kitchen provides direct access to the backyard. Recent improvements include an upgraded stove, washer, dryer, and hot water heater. Outside, the expansive property offers plenty of open space for gardening, outdoor activities, and a variety of possibilities. Adding character and versatility is the property's rustic barn, complete with electricity and a concrete floor. Steeped in local lore, the barn reportedly once served as the original Smithville Store, with ties to moonshine sales during the Prohibition era. Today, this piece of local history offers practical potential for a workshop, storage, hobbies, or other uses. Located in the rural countryside of Caroline County, just outside Federalsburg, this property combines a relaxed country atmosphere, a generous parcel of land, and an intriguing piece of the area's past, with plenty of opportunity to add your own personal touches. This home is being offered As-Is.

27944 Possum Hill Rd, Federalsburg

Listing courtesy of Northrop Realty. Contact:

3881 Laurel Grove Rd, Federalsburg
$699,000
4 Beds ⋅ 3 Baths
YOUR OWN PRIVATE RETREAT ON NEARLY 7 ACRES — WHERE COUNTRY CHARM MEETS COMFORT, SPACE, AND ENDLESS POSSIBILITIES! Welcome to 3881 Laurel Grove Road, an inviting Colonial-style residence nestled on 6.76 acres in the peaceful countryside of Federalsburg, Maryland. Offering the perfect combination of privacy, generous living spaces, outstanding outdoor amenities, and room to pursue your passions, this exceptional property presents a rare opportunity to embrace the Eastern Shore lifestyle you've been dreaming of. Built in 2005, this spacious two-story home features four bedrooms, two full bathrooms, and a convenient half bath, providing plenty of room to spread out, entertain, and enjoy everyday living. Thoughtfully designed with both comfort and functionality in mind, the home welcomes you with inviting gathering spaces, a dedicated dining area, and a versatile floor plan that includes a main-level bedroom. The kitchen serves as a natural gathering place, featuring beautiful granite countertops, stainless steel appliances, and plenty of opportunity to create memorable meals and celebrations. Ceramic tile finishes in the bathrooms add a timeless touch, while the home's generous proportions create an atmosphere that is both comfortable and welcoming. Step outside, and you'll discover what truly sets this property apart! Imagine spending warm summer afternoons lounging beside your very own inground swimming pool, hosting weekend cookouts, or enjoying peaceful evenings surrounded by the beauty of the countryside. Complete with a spacious deck and dedicated pool house, the outdoor entertaining area creates a private getaway right in your own backyard. Whether you're planning lively gatherings or simply enjoying a quiet afternoon, this space is designed for making memories. For those who appreciate extra space for hobbies, projects, vehicles, or equipment, the property delivers in a big way. In addition to the attached garage, a detached garage and workshop with electricity provide valuable flexibility for a variety of interests. Car enthusiasts, woodworking hobbyists, collectors, and anyone seeking additional storage or workspace will appreciate the possibilities these substantial improvements provide. And then there's the land! With 6.76 acres to call your own, you'll enjoy an extraordinary sense of openness and breathing room that is increasingly difficult to find. Envision gardens, outdoor recreation, gatherings under the stars, or simply enjoying the changing seasons from the comfort of your own property. Here, there's room to enjoy the outdoors without sacrificing the comforts of home. Located in Caroline County, this property offers the peaceful atmosphere of rural living while remaining conveniently situated for access to Federalsburg, Denton, Easton, and Seaford. Enjoy the charm of Maryland's Eastern Shore with shopping, dining, recreation, and everyday conveniences within reach. With no homeowners association, the property offers added flexibility to enjoy country living on your own terms, subject to applicable county regulations. More than just a home, 3881 Laurel Grove Road is an opportunity to create the lifestyle you've always imagined. From relaxing poolside afternoons to weekend projects in the workshop and evenings enjoying the peaceful surroundings, this remarkable property combines space, versatility, and country charm in one incredible package. Come discover the possibilities and experience everything this Eastern Shore retreat has to offer!

3881 Laurel Grove Rd, Federalsburg

Listing courtesy of Keller Williams Realty. Contact:

215 Academy Ave, Federalsburg
$255,000
3 Beds ⋅ 2 Baths
Welcome to 215 Academy in Federalsburg! This beautifully renovated three-bedroom, two-full-bath home has undergone an impressive transformation, combining modern finishes, thoughtful upgrades, and a functional layout designed for comfortable everyday living. From the moment you step inside, you'll appreciate the attention to detail and extensive improvements throughout. The main level features beautiful new floating flooring, while the upstairs offers fresh carpeting throughout. The stunning, completely renovated kitchen is truly a showstopper, featuring gorgeous stone countertops with a matching full-height backsplash, brand-new stainless steel appliances, beautiful new cabinetry with soft-close features, and a generously sized pantry offering exceptional storage. The home's thoughtfully designed layout includes both a traditional front entrance and a convenient side entrance leading into a dedicated mudroom. Just off the mudroom, you'll find a separate laundry room and a beautifully renovated full bathroom, adding convenience and functionality to the main level. Upstairs, three comfortable bedrooms and another completely renovated full bathroom continue the home's fresh, contemporary feel. Both bathrooms have been tastefully updated with beautiful tilework, modern fixtures, and stylish finishes that complement the home's overall transformation. Additional improvements include new mini-split heating and cooling systems, replacement of many of the home's windows, and updates to portions of the electrical and plumbing systems. Outside, the inviting front porch provides the perfect place to relax and unwind. A spacious driveway offers plenty of off-street parking, while a large existing concrete pad at the rear of the property provides additional flexibility for parking, storage, or exploring potential future improvements, subject to applicable zoning, permits, and approvals. The manageable in-town yard offers outdoor space without the burden of extensive lawn maintenance. With its extensive renovations, beautifully appointed kitchen, modern bathrooms, convenient layout, and generous off-street parking, this home offers an exceptional opportunity to enjoy the benefits of a thoughtfully updated property without the hassle and expense of undertaking a major renovation yourself. Simply move in, unpack, and enjoy everything this beautifully transformed home has to offer!

215 Academy Ave, Federalsburg

Listing courtesy of Eastern Shore Real Estate, LLC. Contact:

522 Denton Rd, Federalsburg
$215,000
4 Beds ⋅ 1 Baths
Adorable curb appeal, major updates, and room to make it your own! This charming 4-bedroom, 1-bath home at 522 Denton Road offers a great opportunity for buyers looking to add their personal touch without tackling all the big-ticket projects! The seller has already done much of the heavy lifting with remodeling, a new roof, new windows, and a brand-new septic system to be installed prior to settlement. Outside, you'll find two pergolas and a detached one-car garage, adding even more possibilities to this property. With its inviting exterior, important improvements, and plenty of potential left to make it your own, this home is ready for its next chapter. The hard work has started, now bring your vision and make it yours! Back on the market through no fault of the seller. Property is available for showings.

522 Denton Rd, Federalsburg

Listing courtesy of Keller Williams Realty. Contact:

3325 Sharon Ct, Federalsburg
$335,000
3 Beds ⋅ 2 Baths
Welcome to 3325 Sharon Court, a well-maintained home offering comfortable living spaces, thoughtful updates, and an inviting outdoor setup in Federalsburg, Maryland. The main level features a spacious living room with LVP flooring that continues into the kitchen and dining area. The updated kitchen offers quartz countertops, a large island, soft-close cabinetry and drawers, pantry storage, and newer appliances including a dishwasher, electric range, and built-in microwave. Sliding doors lead to the rear deck, while a convenient half bath completes the main level. Upstairs, you'll find three bedrooms with carpeting and ample closet storage, along with a shared full bathroom featuring a tub/shower and updated finishes. A laundry closet with hookups is located in the hallway, and an attic access panel provides additional storage potential. Recent improvements include a new heat pump, new LVP and carpet flooring, updated bathroom, newer kitchen appliances, exterior lighting, and new receptacle covers and switches. Outside, enjoy a tree-lined yard with partial wood fencing and an expansive outdoor living area designed for entertaining and relaxing. The rear deck features a pergola, while a gazebo with a patio and grill provides additional space for gatherings. An above-ground pool, storage shed, and gravel driveway add to the functionality of the property. Located in Federalsburg, this home offers convenient access to MD Routes 313 and 318, connecting to surrounding Eastern Shore communities. Local recreation includes Federalsburg Marina & Recreation Park and the Marshyhope Hike and Bike Trail, while Tuckahoe State Park offers boating, fishing, hiking, biking, and equestrian trails nearby. Some Images have been Virtually Staged

3325 Sharon Ct, Federalsburg

Listing courtesy of Keller Williams Realty. Contact:

2766 Veterans Dr, Federalsburg
$299,900
2 Beds ⋅ 1 Baths
Across from the boat ramp and water view of 3 ponds on the property! Outdoor enthusiasts, nature lovers, and adventure seekers — welcome to your dream retreat. This one‑of‑a‑kind property offers an extraordinary blend of privacy, recreation, and natural beauty that is nearly impossible to find elsewhere. Set on gently rolling terrain overlooking multiple deep‑water ponds, this property delivers exceptional fishing, peaceful kayaking, scenic hiking trails, and endless opportunities to observe local wildlife. Deer roam the back woods, birds frequent the water’s edge, and the entire landscape offers a sense of tranquility that feels worlds away — yet still close to everything you need. The property also includes a 2‑bedroom home (possibly a 3rd). Enjoy all the benefits of living near the water without the added taxes of owning water‑privileged property. Recent enhancements include a charming decorative three‑rail fence and a privacy fence accented with topiary evergreens, adding both character and curb appeal. With its natural setting and recreational features, this property is perfectly suited for those seeking adventure or considering investment potential such as cabin rentals or VRBO. The possibilities are wide open. Just a quarter mile away, you’ll find two boat ramps, a pavilion picnic park, an additional launch area, playground, splash pad, basketball courts, river trails, an electric vehicle charging station, and more — making this location even more desirable for outdoor enjoyment. Don’t miss this rare opportunity. Schedule your visit and experience firsthand the peace, beauty, and uniqueness of this exceptional property. It truly is a retreat like no other.

2766 Veterans Dr, Federalsburg

Listing courtesy of Benson & Mangold, LLC. Contact:

310 Park Ave, Federalsburg
$199,000
2 Beds ⋅ 2 Baths
This charming farmhouse-style home, built in 1904 has undergone a major renovation in 2026. With 812 square feet of thoughtfully designed living space, this delightful residence features two cozy bedrooms and one and a half bathrooms, making it an ideal retreat for those seeking comfort and style. Step inside to discover a beautifully updated interior adorned with luxury vinyl plank flooring, providing both elegance and durability. The heart of the home is the well-appointed kitchen, equipped with essential appliances including a built-in microwave, range, dishwasher, and refrigerator, ensuring meal preparation is a breeze. A convenient stacked washer and dryer on the main floor adds to the home's practicality. Nestled on a generous 0.17-acre lot that backs to trees, this property offers a peaceful outdoor setting perfect for relaxation or entertaining. Parking is hassle-free with a driveway and on-street options available. Experience the charm and warmth of this inviting property, where every detail has been considered for your comfort and enjoyment. Don't miss the opportunity to make this house your home!

310 Park Ave, Federalsburg

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

122 Julie Ln, Federalsburg
$220,000
3 Beds ⋅ 3 Baths
Welcome to this beautifully maintained newer town home that has been virtually staged was built in late 2025, in the charming Riverwalk community of Federalsburg. Offering 3 bedrooms, 2.5 bathrooms, and modern construction, this home combines today's sought-after finishes with the warmth and small-town charm that make Maryland's Eastern Shore such a desirable place to call home. Close to Federalsburg Community Park & Marina, as well as walking Trails. Whether you're a first-time home buyer, looking to downsize, or searching for a newer home with minimal maintenance, this Riverwalk townhome offers exceptional value in a growing community. Experience modern construction, comfortable living, and the lifestyle that makes Federalsburg one of the Eastern Shore's best-kept secrets. Schedule your private tour today and discover why so many are choosing to call Riverwalk home.

122 Julie Ln, Federalsburg

Listing courtesy of Remax Vision. Contact:

104 Chambers St, Federalsburg
$299,800
3 Beds ⋅ 3 Baths
Ready to own without the stress? This fully renovated home is one your friends will be drooling over. Move in and start your life, not your renovation. The kitchen steals the show: soft-close navy cabinets with gold hardware and quartz countertops, stainless steel appliances, a deep kitchen sink, stylish floating shelves, and a crisp white tile backsplash. It's the kind of space that makes cooking and gathering feel effortless. Your first-floor primary bedroom is your sanctuary: walk-in closet, walk-in tile shower that feels like a spa, beautiful quartz vanity. Wide plank LVP flooring keeps the whole home feeling fresh and connected. The two-car detached garage is insulated, has electric, and includes a storage room—practical space that actually works. The 0.325-acre lot sits across from Chambers Park, where you can enjoy a ball game, walking path, or tennis courts. Paved driveway, plenty of parking. This is what move-in ready actually feels like: fully updated, thoughtfully finished, zero projects waiting. And a seller who's willing to work with you on the numbers. Just unpack and live.

104 Chambers St, Federalsburg

Listing courtesy of Benson & Mangold, LLC. Contact:

3894 Old Denton Rd, Federalsburg
$230,000
2 Beds ⋅ 1 Baths
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 provide plenty of peaceful spots to relax and enjoy the outdoors. The property is as functional as it is cozy, boasting an unfinished basement with endless potential for storage, a workshop, or future living space. Outside, you’ll find ample parking, a carport, and storage sheds for all your gear. Schedule your private tour today!

3894 Old Denton Rd, Federalsburg

Listing courtesy of Keller Williams Realty. Contact:

107 Smith St, Federalsburg
$174,000
3 Beds ⋅ 2 Baths
Move-In Ready & Beautifully Remodeled! This charming 3-bedroom, 1.5-bath home offers the perfect blend of comfort and convenience. Enjoy a spacious living room, separate dining area, and a dedicated laundry room for added functionality. The kitchen is designed for both everyday living and entertaining, featuring dual bar seating areas with open views to the living and dining spaces. One bedroom includes a private half bath—ideal for guests or added flexibility. Relax on the inviting front porch, perfect for evening unwinding. Conveniently located near shopping, grocery stores, a public boat ramp, park, and walking trails—with the added bonus of tax-free shopping just a short drive away in Delaware. A must-see home ready for its new owners!

107 Smith St, Federalsburg

Listing courtesy of Mabry Real Estate LLC. Contact:

211 Bloomingdale Ave, Federalsburg
$289,000
2 Beds ⋅ 2 Baths
Back on the market, buyer didn't qualify for their loan. 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 bedroom if desired. The bright, well‑appointed kitchen is ideal for anyone who loves to cook, offering ample room for a kitchen table and direct access to a separate formal dining room—perfect for hosting guests. A convenient half bath is located on the main level, with a full bath upstairs along with two generously sized bedrooms and a large walk‑in storage area. Outside, a concrete driveway leads to an attached garage. There is a brick walkway from house to the town sidewalk. Spacious private backyard with mature trees and a newer roof. This home is truly move‑in ready and waiting for you to enjoy.

211 Bloomingdale Ave, Federalsburg

Listing courtesy of Meredith Fine Properties. Contact:

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