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215 N Main St, Federalsburg
$225,000
3 Beds ⋅ 2 Baths
Welcome to this charming 3BR/2BA classic Craftsman. Pull into the driveway and make your way to the covered front porch and the door to your forever home. Step inside to discover a home filled with original character, including beautiful original hardwood floors throughout. The main level showcases the traditional layout and timeless charm of a Craftsman, featuring a spacious living room that flows seamlessly into the dining room and kitchen. Just off the dining area is a cozy cabin-style room, offering incredible versatility as a family room, home office, or guest bedroom. This space also provides convenient access to a full bathroom featuring a walk-in shower. Upstairs, you'll find two spacious secondary bedrooms and a large primary bedroom filled with abundant natural light. The bedrooms share a full bathroom. The unfinished lower level offers laundry, ample storage, and plenty of room to create additional living space. Outside, the expansive lot provides abundant green space and endless possibilities, making this classic Craftsman a wonderful place to call home. Within the past six years, the home has benefited from several updates, including a new roof and multiple split HVAC units. The main unit can expand the system to accommodate up to three additional units, providing flexibility for future needs. This home also includes a Rinnai tankless hot water heater (2018). From the main floor, step outside onto a large wood deck that leads down to the expansive lot, offering abundant green space and so many possibilities. This home is ideal for any new homeowner and is located in a beautiful neighborhood with convenient access to shopping, restaurants, and commuter routes.

215 N Main St, Federalsburg

Listing courtesy of LPT Realty, LLC. Contact:

216 S 3rd St, Denton
$250,000
3 Beds ⋅ 2 Baths
Why rent when you can own and start building equity and an asset of your own? Priced at just $250,000, this charming home in the heart of downtown Denton offers an affordable opportunity to put your personal touches into a home and make it your own. The main level features a spacious living room with updated flooring, kitchen with separate dining area, office/flex space, mudroom, and a full bathroom, while upstairs you'll find three bedrooms and another full bathroom. An unfinished basement provides additional storage space & laundry and the inviting front porch with swing is the perfect spot to relax and enjoy the charm of this walkable downtown location. Conveniently located near the Choptank River, shops, dining, and everything downtown Denton has to offer. This home offers plenty of space, character, and potential for someone looking for an opportunity to own rather than rent. Seller will need a short 1 week rent back & subject to finding a home of choice. Don't delay and schedule your showing on this adorable bungalow today!

216 S 3rd St, Denton

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

215 Hamilton Dr, Ruther Glen
$200,000
3 Beds ⋅ 2 Baths
Bring your contractor, your vision, and your imagination—215 Hamilton Dr is ready for a complete transformation. This property needs a full renovation from top to bottom and is priced accordingly, offering an opportunity for an investor, experienced renovator, or buyer looking for a serious project. This is not a little paint-and-flooring makeover. The home needs substantial work, but the asking price reflects the condition and is positioned well below comparable renovated homes. For the right buyer, the value is in what this property can become. Renovate for resale, create a rental investment, or completely reimagine it for yourself. If you've been waiting for a true fixer-upper where you aren't paying for someone else's updates, this may be the one. Bring your ideas and take a look at the possibilities!

215 Hamilton Dr, Ruther Glen

Listing courtesy of 1st Choice Better Homes & Land, LC. Contact:

1115 Market St, Denton
$229,900
2 Beds ⋅ 1 Baths
REDUCED $10,000!! Nestled in the charming Town of Denton, this Adorable Cottage exudes warmth and character! Lots of Upgrades and Updates are all sure to please! This beautiful home features 2 Bedrooms and an updated Full Bathroom. The inviting living space is enhanced by luxury vinyl plank flooring, seamlessly blending comfort and style. Set on a generous sized lot, the property offers room for expansion, along with ample outdoor space for gardening, playing, and relaxing in the sun! The private driveway accommodates up to three vehicles, ensuring convenience for you and your guests. A handy shed provides extra storage for your outdoor tools and hobbies. The Denton Area is known for its friendly community vibe, with local parks, shops, waterfront restaurant and eateries just a stone's throw away. Enjoy leisurely strolls through tree-lined streets or explore nearby recreational opportunities. Embrace the charm and make this cute cottage your own!

1115 Market St, Denton

Listing courtesy of RE/MAX Executive. Contact:

12246 Bunya Ln, Ruther Glen
$190,000
3 Beds ⋅ 1 Baths
Investor Special or Make It Your Own! This Ruther Glen home is priced for a buyer ready to put in some work and is being sold strictly as-is. Currently livable but in need of repairs and updates throughout, this property offers an opportunity for an investor looking to build equity or a homeowner ready to renovate and make it their own. Seller has disclosed that a floor joist beneath the kitchen is damaged/broken and that there is visible sagging/depression in the kitchen floor. Seller and Listing Broker make no representation regarding the extent of the condition. Buyer is advised to conduct any inspections deemed necessary. Conveniently located in Caroline County, this home is ready for a fresh start. Bring your vision, your crew, or your Pinterest board and see the possibilities. Seller will make no repairs. Inspections are welcome for buyer's informational purposes only. Cash or hard money financing preferred, though buyers should confirm financing options and property eligibility directly with their lender based on the property's current condition.

12246 Bunya Ln, Ruther Glen

Listing courtesy of Samson Properties. Contact:

6132 Harmony Rd, Preston
$175,000
2 Beds ⋅ 1 Baths
Discover a hidden gem in this charming 2-bedroom, 1-bathroom ranch-style home, built in 1950 and brimming with potential. Nestled on a generous 0.48-acre lot, this property offers ample space for expansion or outdoor enjoyment, making it an ideal investment opportunity for those looking to enhance their portfolio. The detached structure, constructed with durable block materials, presents a solid foundation for your vision. While the home is currently in below-average condition, this offers a unique chance for savvy investors to renovate and increase its value significantly. With a little creativity and effort, you can transform this space into a cozy retreat or a lucrative rental property. The expansive driveway accommodates up to six vehicles, providing convenience for tenants or guests. Located in a peaceful neighborhood, this property is poised for appreciation, especially as the demand for rental homes continues to rise. With the right updates, you can create a warm and inviting atmosphere that appeals to a broad range of tenants, ensuring a steady stream of rental income. Seize this opportunity to invest in a property with great potential and make it your own. The possibilities are endless-turn this house into a home that generates returns for years to come!

6132 Harmony Rd, Preston

Listing courtesy of Exit Community Realty. 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:

163 Riverwalk Ter, Federalsburg
$228,000
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 good-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!! Come see for yourself - schedule appointment today.

163 Riverwalk Ter, Federalsburg

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

305 Old Denton Rd, Federalsburg
$89,900
2 Beds ⋅ 1 Baths
** BEST AND FINAL OFFERS DUE 6/12/26 AT NOON ** Investor Alert!! This rancher, situated on over half an acre, is packed with value-add potential! With some TLC and the right vision, this property could be transformed into a strong income-producing asset or profitable flip in no time. Whether you’re looking to renovate and rent or resell, the opportunity here is undeniable—especially with a motivated seller ready to make a deal. Located in Caroline County, you’ll benefit from an area known for its affordability, growth, and rural charm. Larger lot sizes, fewer restrictions, and strong rental demand make this a smart choice for investors. Plus, you’re conveniently positioned within driving distance to Annapolis, Easton, and Dover, giving you access to major hubs while still enjoying a quieter, more laid-back setting. If you’ve been waiting for your next project with upside potential in a growing area—this is it.

305 Old Denton Rd, Federalsburg

Listing courtesy of Keller Williams Realty Delmarva. Contact:

205 Park Ave, Federalsburg
$239,900
3 Beds ⋅ 2 Baths
Framing has begun! Schedule your tour today! The photos provided in the MLS are for reference purposes only and are intended to reflect the style and quality of similar fixtures, finishes, and features. Actual materials, fixtures, finishes, and selections may vary based on builder availability and final specifications. **Get it under contract prior to completion** Welcome to 205 Park Ave in the charming Town of Federalsburg, MD! Built by Lomaxx Custom Homes, this beautifully designed brand new construction home blends modern comfort, quality craftsmanship, and timeless style. Offering 1,320 sq. ft. of thoughtfully designed living space, this home features 3 bedrooms and 2 full bathrooms, providing both functionality and everyday comfort. Inside, thoughtfully selected finishes create a modern yet cozy atmosphere throughout the home. Luxury LVP flooring, stainless steel appliances, quartz countertops, and beautifully tiled showers combine durability with elevated design. The open-concept living spaces are perfect for gathering and entertaining, while cozy corners throughout the home create inviting spaces to relax and unwind. Designed with low-maintenance living in mind, with nearby amenities such as shopping. The property includes a private driveway. Located in the heart of Federalsburg, residents enjoy the charm of small-town Eastern Shore living with nearby parks, local restaurants, shopping, community events, and outdoor recreation such as fishing. Short commute to other local towns such as Easton, Denton, and tax-free Delaware for tax-free shopping. If you love the beach, Ocean City is about an hour drive! Estimated completion is projected for September 2026, giving buyers the opportunity to secure a stunning brand-new home before completion. Exterior photo has been provided by the builder. Interior colors, finishes, and selections are subject to change at the builder’s discretion. All transfer and recordation taxes to be paid by the buyer. Public water and sewer. Built by Lomaxx Custom Homes — where quality craftsmanship meets modern living.

205 Park Ave, Federalsburg

Listing courtesy of Coldwell Banker Realty. Contact:

156 Main St, Preston
$199,900
3 Beds ⋅ 2 Baths
Located in the heart of Preston, this classic 1900-built home offers a solid opportunity for both homeowners and investors alike. Inside, the home features 3 bedrooms and1.5 bathrooms and a functional layout that includes a combined laundry room, bath, and mudroom with direct access to the back deck—adding everyday practicality. The kitchen has been updated with durable luxury vinyl plank (LVP) flooring, offering a clean and low-maintenance foundation for the space. Enjoy outdoor living from both the covered front porch and the rear porch, providing comfortable areas to relax or entertain. With its central location and existing rental history, this property presents a strong investment opportunity or a chance to make it your own.

156 Main St, Preston

Listing courtesy of Benson & Mangold, LLC. Contact:

522 Market St, Denton
$225,000
4 Beds ⋅ 2 Baths
ATTENTION INVESTORS -- Incredible opportunity in the heart of Denton - Roomy DUPLEX with tons of potential - renovate and hold, fix and flip, or create a long-term income-producing asset. Featuring 2 separate units, each level includes 2 bedrooms and 1 full bathroom, ideal for rental income or multi-family living - OR - convert this home back to its original colonial charm as a single-family home. Denton is a quintessential Eastern Shore town on the banks of the Choptank River. Minutes to the best that Denton and Caroline County offers - great local restaurants, boutique and big-box store shopping, arts + culture, history galore, plenty of public launches and marinas, boating, world-class fishing, crabbing, hunting, wildlife estuaries, incredible state parks - a true paradise for nature lovers, photographers, boaters, fishermen and anyone who wants to enjoy the more relaxed pace on the Eastern Shore - from the beaches to the bays and beyond! Great central location on the Delmarva Peninsula -- 15mi to Easton, 30mi to the Bay Bridge or Cambridge, 40mi to Annapolis's Downtown, about an hour to the Delaware Beaches or Newark, half hour more to Ocean City's Boardwalk. Sizes, taxes, distances approximate

522 Market St, Denton

Listing courtesy of EXP Realty, LLC. 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:

1204 Blue Heron Dr, Denton
$230,000
3 Beds ⋅ 3 Baths
***NEWLY ADJUSTED PRICE***Come on in to explore this beautifully maintained 3-level home offering the perfect blend of modern convenience and comfortable living. This beauty features 3 spacious bedrooms and 2.5 baths, with an open floor plan that creates an inviting flow throughout the main living areas. The home has been updated with fresh paint, new appliances and more to ensure it's move-in ready for you. Each level offers its own distinct living space providing flexibility for various lifestyle needs. Location is everything, and this home delivers convenience. Situated in a premium location with ideal access to both Route 404 and Route 50 for effortless commuting and easy access to shopping, dining and entertainment. Whether you're headed to work or exploring the area, everything you need is just minutes away.

1204 Blue Heron Dr, Denton

Listing courtesy of Shore Results Realty. Contact: