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1115 Market St, Denton
$224,900
2 Beds ⋅ 1 Baths
REDUCED $15,000! 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:

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:

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!

522 Denton Rd, Federalsburg

Listing courtesy of Keller Williams Realty. Contact:

Trunk Rd, Henderson
$199,900
Discover the possibilities on this 14.71± acre wooded parcel on Trunk Line Rd in Henderson, MD, now offered at $224,900. Perc approved for a conventional septic system serving a 4+ bedroom dwelling, this property offers the opportunity to build a custom home while enjoying the privacy and space of a rural setting. With approximately 466 feet of road frontage along Trunk Line Road and a designated sewage reserve area shown on the recorded plat, the property provides flexibility for your future plans. The mature woods make this parcel well-suited for outdoor recreation, hiking, wildlife observation, and, subject to applicable laws and regulations, hunting. Whether you’re looking to build a primary residence, weekend retreat, or private getaway, this property offers a peaceful setting with convenient access to nearby towns, shopping, dining, and major travel routes. No builder tie-in. Buyer is responsible for verifying all information and performing due diligence regarding permits, utilities, zoning, land use, and building plans.

Trunk Rd, Henderson

Listing courtesy of The Parker Group. 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:

215 N Main St, Federalsburg
$199,500
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:

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:

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:

11920 Central Ave, Ridgely
$179,000
Huge Price Drop – Act Fast Before It’s Gone! (Serious Buyers Only) This exceptional property features over 16 acres of level land with frontage on three roads: Central Avenue, Henry Road, and Holly Plains Drive. Zoned R-1, it offers outstanding potential—perfect for holding, subdividing, or developing. Located just outside the Ridgely city limits and close to the town center, the property is well-positioned for future growth. With nearby sub-acre lots selling for around $130K, this presents a rare and compelling opportunity for subdivision and investment. Serious buyers only—don’t miss your chance to secure this versatile and high-potential piece of real estate. MLS listing is limited service for entry purposes only. Seller will handle all inquiries, negotiations, and contract details directly. Listing agent has a financial interest in the transaction.

11920 Central Ave, Ridgely

Listing courtesy of Proplocate 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:

Pond Rd, Ruther Glen
$154,900
USE 18330 POND RD RUTHER GLEN FOR GPS - WILL TAKE YOU RIGHT TO THE PARCEL B Incredible opportunity to build on this beautiful piece of land! Years before seller purchased, this parcel had a functioning well and septic. Purchaser will be responsible to get a perk test - soil study etc. The property has electricity in place (power pole). Please schedule your showing so the seller can make sure she is present to help understand the location of the corners. The property has “Do Not Enter” signs intended to discourage unauthorized recreational access, including dirt-bike riding and fishing. These signs do not prevent scheduled property showings. Please do not enter or explore the property without an appointment. Contact the listing agent for pricing, additional information, and access instructions.

Pond Rd, Ruther Glen

Listing courtesy of Real Broker, LLC. Contact:

6132 Harmony Rd, Preston
$150,000
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:

Trunk Line Rd, Henderson
$134,900
Secluded 5-Acre Perc-Approved Building Lot Nestled on a quiet country back road, this beautiful 5-acre parcel offers peace, privacy, and great potential. The front section—where the perc test has been approved—is lightly overgrown with small saplings, making for easy clearing and minimal cost to install a driveway and run utilities to your future home site. The rear portion of the property features a mix of mature hardwoods, offering a serene natural backdrop and added privacy. Abundant deer signs make this spot perfect for hunters or nature lovers looking to enjoy wildlife right in their own backyard. Whether you're dreaming of a rural retreat, homestead, or hunting getaway, this property is ready for your vision.

Trunk Line Rd, Henderson

Listing courtesy of Taylor Properties. Contact:

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