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$459,900
4 Beds ⋅ 4 Baths
This well-maintained duplex in Rio Vista presents an exceptional investment opportunity, featuring two spacious units, each offering 2 bedrooms and 1.5 baths. Ideally situated just moments from the heart of historic downtown St. Michaels, residents enjoy easy access to charming shops, dining, and waterfront attractions—all while benefiting from no town taxes. With both units currently 100% leased, this property provides immediate, reliable income, making it a smart addition to any investment portfolio.

104 Madison Ave, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$2,299,000
This commercial property in St Michaels presents a unique investment opportunity. Situated on a 2.24-acre lot, the property benefits from a prime highway location, ensuring high visibility and accessibility for future tenants or customers. This property lends itself to a variety of business ventures. the flexibility of parking options enhance its attractiveness for commercial use. Investors can capitalize on the growing demand for commercial spaces in this area, leveraging the strategic location while the focus remains on land utilization and development potential. This property is ideal for those looking to invest in a versatile space with the opportunity for appreciation and income generation.

941 S Talbot St, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$359,900
2 Beds ⋅ 3 Baths
Located in the desirable Martingham community, this two-bedroom, two-and-a-half-bath condominium offers comfortable living just minutes from historic downtown St. Michaels. The main level features a spacious living room with hardwood flooring and a wood-burning fireplace, a convenient half bath, and a full-season sunroom overlooking the backyard with direct access to the outdoor space. A detached one-car garage provides additional parking and storage. Upstairs, both bedrooms feature en-suite baths, including a rear bedroom with a private balcony overlooking the backyard and The Links at Perry Cabin Golf Course. Brand-new carpeting has just been installed throughout the upper level, and the home also features a brand-new water heater. Conveniently located near shopping, dining, waterfront parks, and the many attractions of downtown St. Michaels, this property offers an excellent opportunity to enjoy Eastern Shore living.

9531 Quail Hollow Dr Unit #405, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$849,000
3 Beds ⋅ 2 Baths
Thoughtfully reimagined from the studs out, this exceptional residence offers the character of an in-town cottage with the quality, comfort, and finishes of a newly constructed home. Every detail has been carefully considered, creating a seamless blend of timeless charm and modern design. A welcoming front porch with a classic porch swing sets the tone before stepping inside to a light-filled interior featuring soaring vaulted ceilings and an open-concept floor plan designed for effortless everyday living and entertaining. Rich hardwood flooring flows throughout, complemented by a beautifully appointed chef’s kitchen, three well-proportioned bedrooms, and two elegantly finished full baths—all conveniently situated on a single level. Virtually every component of the home has been renewed, allowing the next owner to enjoy a truly turnkey property with the peace of mind that comes with comprehensive renovation. Outside, professionally designed landscaping surrounds a private backyard, creating a tranquil setting for outdoor dining, entertaining, or quiet relaxation. Ideally located in the heart of St. Michaels, the home is just moments from the town’s renowned boutiques, acclaimed restaurants, waterfront parks along the Miles River, the community pool, and the YMCA. Offering the rare combination of like-new construction and one of Maryland’s most desirable small-town settings, 803 New Lane presents an exceptional opportunity to enjoy Eastern Shore living at its finest.

803 New Ln, St Michaels

Listing courtesy of TTR Sotheby's International Realty. Contact:

$309,000
3 Beds ⋅ 2 Baths
Discover this ranch-style home located 1 block to the center of downtown, perfect for those seeking convenience to everything St Michaels has to offer. This 3-bedroom, 2-bathroom residence offers 1,364 sq. ft. of potential, set on a generous 0.17-acre lot. The rails to trails is located right at the end of the street. With a little creativity and vision, this property can be transformed into your dream home. Roof was replaced in 2014, HVAC 2014, hot water heater 2015. Fence panels have been removed, posts remain, they are on the property line. No permit would be needed to add new panels. There is space for a driveway to be added to the left of the home. Embrace the opportunity to invest in a community that values connection and quality of life. Don't miss out on this chance to make it your own!

203 Canton St, St Michaels

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact: