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$229,700
2 Beds ⋅ 2 Baths
Discover a unique investment opportunity in the charming Victorian-style home located in the serene Tilghman Island. This detached residence, built in 1900, boasts 2 over/under units of well-maintained living space, each featuring a spacious bedroom and full bathroom. The interior is adorned with hardwood and partially carpeted floors, enhancing its classic appeal. Investors will appreciate the built-in features, energy-efficient double-pane windows, and a cozy gas fireplace, perfect for attracting quality tenants. The country-style kitchen is equipped with essential appliances, including a refrigerator, built-in microwave, oven/range, dishwasher, and washer/dryer, ensuring convenience for future occupants. The expansive 0.42-acre lot offers ample outdoor space, complemented by inviting patios and porches, ideal for relaxation or entertaining. With off-street parking and a shed for additional storage, this property is primed for rental income or long-term appreciation. Seize this chance to invest in a timeless gem with significant potential!

4869 Bar Neck Rd, Tilghman

Listing courtesy of Maryland Realty Connection. Contact: admin@mdreoconnection.com
$1,195,000
5 Beds ⋅ 6 Baths
Incredible opportunity to own a circa 1875 home in Oxford's Historic District that has been renovated with a separate 2 bedroom apartment with views of Town Creek. Formerly a Bed and Breakfast, it features 2 first floor bedrooms with 1 and 1/2 baths and 3 second floor bedrooms each with its own full bath. Entire exterior has been newly painted and most of the windows have been replaced. A lovely side garden with a fountain, front porch close to Town Park, and a one and one half car garage with room for a workshop compliment the home. The bright, newly renovated kitchen is the center of the house featuring an alcove with a large kitchen table. It overlooks the side garden. Owner prefers 24 hour notice if possible

110 N Morris St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$2,300,000
4 Beds ⋅ 3 Baths
"New Scotland Farm" First time offered in decades! This special and unique offering includes 100 +/- acres of prime farm and hunting land, encompassing a spacious farmhouse and three additional income producing properties, two ponds, and deeded water access with a dock and slip on LaTrappe Creek. There is the potential for subdivision of 4 lots outside the of the critical area. (buyer to verify) This offering consists of three parcels: Parcel #1 Main House with Rental Properties 21.34 +/- acres improved by a 5BR farmhouse (which includes a separately rented apartment above the garage), two guest cottages that are income producing, and two scenic ponds, one that can be hunted year round. A newly refurbished tennis court and pavilion overlook the second pond. The main house, a Victorian style farmhouse, has a brand new roof , geothermal units and outdoor deck. There is a historic section of the home and an addition built in the 1990’s. The main house also features a separate apartment above the garage for income potential, or ideal for a caretaker. Beautiful setting with mature trees, complete privacy and lovely vistas from several vantage points. Parcel #2 Land 83+/- acres (65 in till) in agriculture. Farm tenant in place. Community Boat Slip (25% interest) 1.424 +/- acres Deeded boat slip and water access on LaTrappe Creek via shared pier with 3 other homes. This is a unique property with an endless potential of uses, from a hunting retreat, private getaway, investment or combination of all.

28923 Island Creek Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$2,300,000
4 Beds ⋅ 3 Baths
"New Scotland Farm" First time offered in decades! This special and unique offering includes 100 +/- acres of prime farm and hunting land, encompassing a spacious farmhouse and three additional income producing properties, two ponds, and deeded water access with a dock and slip on LaTrappe Creek. There is the potential for subdivision of 4 lots outside the of the critical area. (buyer to verify) This offering consists of three parcels: Parcel #1 Main House with Rental Properties 21.34 +/- acres improved by a 5BR farmhouse (which includes a separately rented apartment above the garage), two guest cottages that are income producing, and two scenic ponds, one that can be hunted year round. A newly refurbished tennis court and pavilion overlook the second pond. The main house, a Victorian style farmhouse, has a brand new roof , geothermal units and outdoor deck. There is a historic section of the home and an addition built in the 1990’s. The main house also features a separate apartment above the garage for income potential, or ideal for a caretaker. Beautiful setting with mature trees, complete privacy and lovely vistas from several vantage points. Parcel #2 Land 83+/- acres (65 in till) in agriculture. Farm tenant in place. Community Boat Slip (25% interest) 1.424 +/- acres Deeded boat slip and water access on LaTrappe Creek via shared pier with 3 other homes. This is a unique property with an endless potential of uses, from a hunting retreat, private getaway, investment or combination of all.

28923 Island Creek Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$339,000
4 Beds ⋅ 2 Baths
Live the Tilghman Island lifestyle just steps from the Chesapeake Bay. Perfectly positioned in the heart of historic Tilghman Island, this updated four-bedroom home offers the ability to enjoy one of Maryland's most authentic waterfront communities without the waterfront price tag. Walk to marinas, waterfront restaurants, charter fishing, Tilghman Wharf, and the iconic drawbridge, or spend your days exploring the Chesapeake by boat, kayak, or bicycle. Originally inspired by one of Tilghman's classic "M" homes, the residence blends timeless island character with modern updates. Inside, you'll find a spacious, open floor plan featuring an updated kitchen with granite countertops, stainless steel appliances, and abundant cabinetry, along with beautifully renovated bathrooms, new flooring, and a flexible layout that includes a first-floor bedroom and full bath—ideal for guests or one-level living. Three additional bedrooms and another updated full bath are located upstairs, providing plenty of space for family and friends. A new HVAC system adds year-round comfort, while the generous yard offers room for gardening, entertaining, or simply relaxing after a day on the water. Whether you're searching for a full-time residence, a weekend retreat, or an investment in one of the Eastern Shore's most charming villages, this home delivers exceptional value at an attractive price point. Experience the slower pace, rich maritime heritage, and unmatched sense of community that make Tilghman Island one of the Chesapeake Bay's hidden gems.

21524 Chicken Point Rd, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$1,179,000
4 Beds ⋅ 3 Baths
Beautifully restored Historic Victorian in the heart of Saint Michaels. This charming home has a strong rental history, last tenant was paying $4,500 a month. From the wide, welcoming front porch to the gated, manicured yard—complete with a hammock ideal for long afternoon naps—every space is designed for comfort and relaxation. A brick walkway leads to the custom beveled‑glass entry door and into the warm, inviting family room. Inside, the home features rich pine floors throughout, a cherry kitchen with stainless steel appliances, granite countertops, and an open flow into the charming dining room. The spacious family room includes a propane stove for cozy winter days. The first floor also offers a full laundry room and an ornate powder room. The original staircase leads to the second floor, which includes three bedrooms and a renovated marble‑tile full bath. The private third‑floor primary suite offers a peaceful retreat with its own en‑suite bath. Just one block from the water—with water views from the street—this home captures the best of small‑town living. Enjoy walking access to Saint Michaels’ restaurants, quaint shops, kayaking, swimming, boating, and biking. It’s a special property ready for unforgettable memories with family and friends. Whether you're looking for a proven investment property or a beautiful home for your family, this one stands out.

101 Mulberry St, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$414,900
4 Beds ⋅ 3 Baths
Charming Victorian in Historic Easton! This unique single-family home offers the perfect blend of modern style and classic early-1900s character. Featuring 4 bedrooms and 2 fully renovated full baths, this multi-level home showcases timeless architectural details including two fireplaces, a welcoming large front porch, and original/rebuilt single-pane wood windows across the front that preserve its historic charm. Inside, enjoy an open-concept layout with a spacious living room, dining room, and kitchen—ideal for entertaining. Step right out from the dining area onto a huge rear deck, perfect for outdoor gatherings and relaxing evenings. While the home offers a modern feel with historic touches, it does require additional work and will not qualify for standard financing. Ideal opportunity for an investor or buyer looking to restore and build equity in one of Easton’s most desirable historic areas on Maryland’s Eastern Shore.

101 Chapel Rd, Easton

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: howardcounty@penfedrealty.com