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$995,000
3 Beds 2 Baths
Nestled in a farm like setting, this exquisite ranch-style home offers a luxurious lifestyle on a sprawling 40.64+/-acre lot, seamlessly blending elegance with nature. The property boasts modern comforts throughout its 1,568+/- sq. ft. of meticulously designed space. Step inside to discover an inviting interior adorned with rich hardwood and plush carpet flooring. The traditional floor plan features a spacious combination kitchen and dining area, complete with upgraded countertops, a country-style kitchen island, and energy-efficient appliances, including an ENERGY STAR refrigerator and self-cleaning oven. The home is equipped with an advanced air filter system and water treatment system, enhancing indoor air quality and convenience. The exterior is equally impressive, featuring extensive hardscaping, ambient exterior lighting, and a personal heated pool, perfect for relaxation and entertainment. The property includes multiple outbuildings, such as a guest house and utility building, providing ample space for guests or hobbies. Enjoy breathtaking views of lush pastures and wooded areas, with direct access to the tranquil Marshyhope creek, ideal for fishing and outdoor activities. The lot adjoins open space and game land, offering a serene, rural lifestyle while remaining conveniently close to modern amenities. This exceptional property is a rare find, combining luxury living with the beauty of nature, making it a true sanctuary for those seeking an exclusive lifestyle.

5315 Smithville Rd, Federalsburg

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$75,000
This purchase includes two lots totaling 3.73 acres on the corner of Miles branch Rd and Meadowbrook Rd. Lot #1 is buildable and high (a perc approval was obtained in 2024) - 1.229 acres. Sellers cleared 3/4 of an acre on the buildable lot. Sellers had obtained a building permit that was approved through Caroline County for a 1650 sq ft one story home, plus garage with a well and an septic system. Lot #2 is Open space and not buildable per deed - 2.5 acres - Plat included in documents. Excellent neighborhood just outside of Federalsburg, MD with easy access to Bridgeville, DE, Seaford, DE and about 40 minutes +/- to Easton and/or Denton, MD. with a high area for your new home and a potential park setting with a stream on lot #2.

2821 Meadowbrook Rd, Federalsburg

Listing courtesy of LPT Realty, LLC. Contact: 8773662213

$325,000
5 Beds 3 Baths
Space, flexibility, and outdoor living come together at 2792 Meadowbrook Road! This spacious 5-bedroom, 2.5-bath split-level home sits on a beautiful .46-acre lot. The upper level features three bedrooms, including a primary bedroom with its own private bath. The living room offers an open feel and an opportunity to create an even more unique space with the potential for an upper balcony. The kitchen provides abundant cabinet storage and plenty of natural light. Downstairs, you'll find two additional bedrooms, a large family room with an electric fireplace, and a charming stone sitting area with a large sliding glass door that opens directly to the backyard and expansive concrete patio. The layout provides great flexibility for guests, a home office, recreation space, or whatever fits your lifestyle. Step outside and enjoy the privacy of the backyard, complete with an above-ground pool and deck, large patio, and plenty of room to create your own outdoor retreat. Imagine summer afternoons by the pool, gatherings on the patio, or adding a firepit area to make the backyard your own. The home is in good condition and is ready for its next owner to add their own personal touches to make the space their next home sweet home. Conveniently located in a quiet neighborhood setting while still offering easy access to Federalsburg, Bridgeville, Seaford, and Denton.

2792 Meadowbrook Rd, Federalsburg

Listing courtesy of Keller Williams Realty. Contact: 3023600300

$309,000
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: (410) 745-0415

$755,000
3 Beds 2 Baths
This is your farmette dream come true! This beautiful 3 bed, 2 full bath home is situated on 6+ acres of partially fenced in land, has a barn with a tack room, a large screened-in back porch, a 2 car garage and an in-ground saltwater pool. The barn features 3 stalls, a hay loft with elevator, washroom, a tack room with a closet and shelves for storage. The water to the barn is sourced from a 290 foot well that also sources to the home. There is also a paddock area for riding and training for your equestrian dreams. The saltwater pool goes up to 6 feet deep. Solar panels were installed in the yard to heat the pool which extends the months of use. The home has a nice front porch perfect for enjoying your country living setting. As you enter the home, the living room has a stand alone Argon gas stove. You'll love cooking and entertaining in the large eat-in kitchen with stainless steel appliances. The second living room has a gas fireplace perfect for cozy evenings. The updated bathrooms have walk in showers. Other features include newer Anderson windows, newer siding, tankless water heater and a semi-floored attic. You don't want to miss the opportunity to enjoy country living at it's best! Schedule your showing today.

3769 Bradley Rd, Federalsburg

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

$99,000
3 Beds 2 Baths
AS IS! GREAT INVESTMENT PROPERTY! This charming 3-bedroom, 1-bathroom traditional home, built in 1944, offers a solid investment opportunity with its AS IS condition gives you a blank slate to modernize this home to fit your needs! The traditional floor plan maximizes space, creating a warm and inviting atmosphere perfect for comfortable living. With a manageable lot size of 0.09 acres, maintenance is simplified, allowing for a focus on maximizing rental income or future resale value. The property features off-street parking, enhancing convenience for tenants or guests. Investors will appreciate the potential for appreciation in this desirable area, coupled with the opportunity to enhance the property further through updates or renovations. This home is not just a residence; it's a canvas for future growth and profitability. Don't miss the chance to add this gem with all its potential to your portfolio!

101 S University Ave, Federalsburg

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

$399,000
Exceptional owner-user or investment opportunity in the heart of Federalsburg's primary retail corridor. This ±6,375 SF Class A end-cap commercial unit is located within the established Bloomingdale Square Shopping Center, surrounded by national and regional retailers including Food Lion, McDonald's, Domino's, Royal Farms, and the future Wawa development nearby. Offered as a vanilla shell, the property is ready for immediate customization and is well suited for retail, medical, professional office, educational, fitness, restaurant, or service-oriented uses. Features include six large storefront display windows, multiple customer entrances, four HVAC units, ADA-compliant restrooms, rear storage, monument signage, and access to more than 200 shared parking spaces.

3338 Hayman, Federalsburg

Listing courtesy of Keller Williams Realty Delmarva. Contact: (410) 524-6400

$95,000
Tucked away at the end of a quiet cul-de-sac, this wooded homesite at 5602 Federal Hill Rd offers the perfect opportunity to build your dream home in a peaceful Eastern Shore setting. With no HOA restrictions, you'll enjoy the freedom to create a property that suits your lifestyle, whether you envision a private retreat, custom residence, or weekend getaway. Surrounded by mature trees, the lot provides natural privacy and a serene backdrop while remaining conveniently located near Federalsburg's local amenities, parks, schools, and outdoor recreation. Bring your own builder and your vision—this is a rare chance to own a tranquil parcel where you can enjoy the beauty of nature without sacrificing convenience. No builder tie-in's and when combined with adjacent parcel being sold with it's over 2 acres of paradise! Don't miss the opportunity to secure your own slice of Maryland's Eastern Shore and build exactly what you've been dreaming of. Being sold with 5600 Federal Hill Rd

5602 Federal Hill, Federalsburg

Listing courtesy of Engel & Volkers Ocean City. Contact: (443) 292-6767

$95,000
Discover the possibilities at 5600 Federal Hill Rd, Federalsburg, MD! Tucked away at the end of a quiet cul-de-sac, this vacant parcel offers the perfect opportunity to build the home you've been dreaming of. Enjoy the freedom of no HOA, giving you the flexibility to create a property that fits your lifestyle without restrictive community regulations. No builder tie-in's and when combined the property is little over 2 acres of paradise! Whether you're planning a custom residence, a peaceful weekend retreat, or an investment for the future, this lot provides a tranquil setting with the privacy and low-traffic appeal of a cul-de-sac location. Conveniently situated near local amenities while still offering a relaxed, rural atmosphere, this property is ready for your vision to come to life. Don't miss your chance to own a piece of land with endless potential in charming Federalsburg. Bring your builder and start planning your future today! Being sold with 5602 Federal Hill Rd adjacent to this lot

5600 Federal Hill Rd, Federalsburg

Listing courtesy of Engel & Volkers Ocean City. Contact: (443) 292-6767

$380,000
3 Beds 1 Baths
This charming ranch-style home, built in 2004, offers a cozy retreat on over 11 acres of serene land, adjoining the picturesque Marshyhope Creek with 3800 acres of Idlewild WMA just across the creek. Inside, discover a traditional floor plan featuring three inviting bedrooms and a country-style kitchen perfect for gatherings. Enjoy the warmth of luxury vinyl plank and carpet flooring throughout. Step outside to find a welcoming porch and patio, ideal for relaxing or entertaining. The property includes a detached 40x24, 2 Car garage with workshop for ample storage. Nature enthusiasts will appreciate the wooded surroundings, stream access, and opportunities for fishing and hunting right at your doorstep. Located in a peaceful, rural setting, this home is just a short drive from local parks and community amenities. Embrace the tranquility and beauty of this unique property, where comfort meets nature.

4455 Smithville Rd, Federalsburg

Listing courtesy of RE/MAX Executive. Contact:

$205,000
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:

$479,000
3 Beds 3 Baths
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, New refrigerator July 2026, new HVAC 2021, 3yr old whole house water treatment with R/O system, and a 40 breaker 4D electrical panel is new, too! With a mix of formal rooms and recreation areas all off the kitchen, but split from the generously sized Bedrooms, you will have no problem entertaining all year round. 2 Sheds, both with electric, one with garage door and workbenches help with all those indoor and outdoor projects. 3rd full bath is off the enclosed sunporch for ease of use from multiple areas and outside. In addition to Chambers Park the Federalsburg Park and Marina is just down the road for added recreation, along with shopping and restaurants in Federalsburg, Easton, Preston, or just over into Delaware not to mention multiple Beaches in both MD and DE that are close enough to spend the day and come back home. Don't miss your opportunity to see this one and call it yours!

104 Charlotte Ave, Federalsburg

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

$229,000
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:

$315,000
3 Beds 3 Baths
Ready to own without the stress? Move in and start your life, not your renovation. This fully renovated home is one your friends will be drooling over. 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. The 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, and a home that's honestly ready for you. This is what move-in ready feels like: fully updated, thoughtfully finished, and zero projects waiting. Just unpack and live.

104 Chambers St, Federalsburg

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$599,000
Enjoy 129 ± acres of recreational land in Caroline County, Maryland. The property includes approximately 80 ± acres of timberland protected by easement (see attached Restrictive Covenants) and 50 ± acres of tillable land, offering a balance of wildlife habitat and farmland. The 80 ± acres of timberland consist of a mix of Hambrook and Fallsington sandy loam soils and provide natural habitat for deer, turkey, and other wildlife. The 50 ± acres of tillable land consist primarily of Hambrook soils, supporting continued agricultural use. Located less than one mile from a Maryland Wildlife Management Area, the property provides convenient access to thousands of acres of public hunting land and conserved wildlife habitat. With road frontage, easy access, and Very Low Density Residential zoning, the property also offers the potential for a private residence, subject to county regulations. This property offers a combination of farmland, timberland, and wildlife habitat suitable for hunting, recreation, conservation, or long-term land investment.

Federalsburg

Listing courtesy of The Land Group. Contact: (410) 934-3478

$234,900
3 Beds 3 Baths
This lovely end-unit condo has units on the left side but no units on the right side, offering more quietness and privacy. This beauty has comfort of "home" written all over. Featuring 3 nice-sized bedrooms; a convenient half-bath is located on first level. The kitchen is very well designed with lots of beautiful cabinets and countertops. Bright open floor plan offering ease of flow for the kitchen, living room, and dining areas. The primary bedroom has a great walk-in closet and its en suite bathroom. Walking trails nearby is a wonderful way to get exercise and enjoy the outdoors. Located not far from shopping. Come see this beauty today and be glad you did -- you will be very impressed with its easy flow open floor plan and the condition of everything from top to bottom, like brand new!! Seller moved to be closer to his job. Come see for yourself - schedule appointment today.

163 Riverwalk Terrace, Federalsburg

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$380,000
3 Beds 2 Baths
If you've been searching for a property that offers acreage, privacy, and plenty of room to grow, this is the one you've been waiting for! Nestled on 3.80 wooded acres, this ranch-style home offers approximately 1,904 square feet of comfortable living space, featuring 3 bedrooms, 2 full baths, and two versatile bonus rooms that can easily serve as a home office, hobby room, playroom, guest space, or additional storage. The spacious primary suite provides a relaxing retreat with a large walk-in closet and an ensuite bath complete with a jetted soaking tub, tiled shower with glass sliding doors, and a single vanity with generous counter space. Two additional bedrooms and a full hall bath provide comfortable accommodations for family and guests. The heart of the home is the open living room and kitchen area, creating a welcoming space for everyday living and entertaining. The kitchen features stainless steel appliances, a built-in pantry, an island with seating for two, and room for a dining table. A separate laundry room includes a washer and dryer along with shelving for added storage. Step outside and enjoy the peaceful natural surroundings from either of the two decks, one of which is equipped with a handicap-accessible ramp. The paved driveway offers abundant parking and extends to the detached garage, making it ideal for vehicles, equipment, or workshop space. Surrounded by mature trees and offering the seclusion many buyers desire, this property combines the tranquility of country living with the functionality and space today's homeowners need. Schedule your showing and see all that this unique property has to offer!

28440 Bloomery Rd, Federalsburg

Listing courtesy of Century 21 Home Team Realty. Contact: 8004477711

$305,000
3 Beds 2 Baths
MOTIVATED SELLER!!! 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. Step outside to relax on the screened side porch or entertain from the patio overlooking mature trees that provide a peaceful, private backdrop. The partially fenced yard is ideal for pets, while the above-ground pool offers the perfect place to cool off during the summer months. Additional highlights include a roof that is less than 10 years old, attractive finishes throughout, and a property that combines charm, comfort, and outdoor enjoyment. Move-in ready and full of character, this Federalsburg gem is one you won't want to miss!

129 Bloomingdale Ave, Federalsburg

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

$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: (302) 856-1458

$11,570,000
This 178,000-square-foot industrial facility sits on 15.40 acres within an Opportunity Zone. The building features clear heights of 31 feet at the center and 24 feet at the eaves, along with 16 dock doors (including three pit docks), two drive-in doors, and a fully sprinklered dry-pipe fire protection system. The property currently generates $70,772 annual income. Approximately 30,000 square feet is leased, leaving 148,000 square feet available for an owner-occupant or additional tenant. Additional revenue is derived from leases on a portion of the parking lot and adjacent grassy areas, while still preserving ample acreage for future parking expansion or site improvements. Located within the Caroline Industrial Park, just one-half mile from downtown Federalsburg and minutes from Maryland Routes 318 and 404, the property benefits from excellent regional accessibility. The industrial park is fully served by electricity, natural gas, public water and sewer, broadband internet, paved roads, and dedicated fire and police protection, making it an ideal location for manufacturing, warehousing, distribution, and logistics operations. The property's strategic Mid-Atlantic location provides convenient access to several major ports, including Baltimore (80 miles), Philadelphia (124 miles), Norfolk (170 miles), and New York (207 miles). The surrounding region also offers a skilled workforce, competitive operating costs, and a business-friendly environment that supports continued growth and investment.

1007 Caroline Dr, Federalsburg

Listing courtesy of SVN/Miller Commercial Real Estate. Contact: 410-543-2440

$1,200,000
Ready for Development! Owner financing possible with down payment. Terms negotiable. 43 lots within the Town limits of Federalsburg, Maryland. Total lot space as currently platted is 478,596 sq ft or 11 acres, according to public records. Total property area including the unbuilt road space is roughly 13 acres. Right-of-ways to the property are currently platted from Liberty Rd, Bernard Ave, and the Federalsburg Bypass. 855 ft of frontage on the Federalsburg Bypass. Water and sewer available on Bernard Ave. Parcel 05-000211 (lot 17c) is available for purchase from a separate seller. The negotiated price of lot 17c can be deducted from the purchase price of the other 42 parcels. The space could fit an estimated 41 single family homes on conforming lots if the property is replatted to a more efficient layout and road design (see example in images). Estimated Gross Development Value (GDV) for 41 homes is $12,300,000. Listing Agent is also the owner of the property. Property to be conveyed as-is. Buyer to perform due diligence and verify all information. 44 Lots pictured in image because lot 1c is a double lot. Property ID in listing is only for the first lot. List of all property IDs attached. Make an offer!

Liberty (Rifkin Village) Rd, Federalsburg

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: