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409 Railroad Ave, St Michaels

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

With extensive updating done less than three years ago, this home in the popular Martingham community shows beautifully! The spacious, open living room with hardwood floors and fireplace overlooks a pavered patio and lots of greenspace beyond. The kitchen is up to date and well designed, and a pocket door separates it from the first floor bedroom suite, which could also be a den or office. Upstairs are two generous ensuite bedrooms with updated baths. A slider off the primary bedroom leads to a porch overlooking the landscaped grounds. A one-car garage is just outside the front door, and additional parking is available just steps away. All this within a mile of historic St. Michaels (but no town taxes!).

3 Beds ⋅ 3 Baths

With extensive updating done less than three years ago, this home in the popular Martingham community shows beautifully! The spacious, open living room with hardwood floors and fireplace overlooks a pavered patio and lots of greenspace beyond. The kitchen is up to date and well designed, and a pocket door separates it from the first floor bedroom suite, which could also be a den or office. Upstairs are two generous ensuite bedrooms with updated baths. A slider off the primary bedroom leads to a porch overlooking the landscaped grounds. A one-car garage is just outside the front door, and additional parking is available just steps away. All this within a mile of historic St. Michaels (but no town taxes!).

9521 Quail Hollow Dr Unit #605, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$799,950

Enjoy the best of St. Michaels with convenient access to recreation, waterfront activities, schools and downtown. The newly renovated split-foyer home is truly move-in ready. The nicely landscaped grounds feature a fenced rear yard with mature trees, large patio and an in-ground swimming pool, creating a wonderful setting for outdoor enjoyment. Inside, the main level is filled with natural light and offers an open floor plan with a comfortable living room, dining area and brand new beautifully updated kitchen featuring white cabinetry and new appliances. Beautiful wood floors throughout. The home offers four bedrooms and three and a half baths, with the added convenience of stacked washer and dryer setups on both levels. Large family room overlooking rear yard with wood burning brick fireplace with outside access to pool. First and second floor primary suites with custom tile bathrooms. Off street parking with no rental restrictions and no town taxes. Close to YMCA, school, restaurants, grocery stores, museums, and downtown shops. A wonderful place to settle in and enjoy the lifestyle that makes St. Michaels so special.

4 Beds ⋅ 4 Baths

Enjoy the best of St. Michaels with convenient access to recreation, waterfront activities, schools and downtown. The newly renovated split-foyer home is truly move-in ready. The nicely landscaped grounds feature a fenced rear yard with mature trees, large patio and an in-ground swimming pool, creating a wonderful setting for outdoor enjoyment. Inside, the main level is filled with natural light and offers an open floor plan with a comfortable living room, dining area and brand new beautifully updated kitchen featuring white cabinetry and new appliances. Beautiful wood floors throughout. The home offers four bedrooms and three and a half baths, with the added convenience of stacked washer and dryer setups on both levels. Large family room overlooking rear yard with wood burning brick fireplace with outside access to pool. First and second floor primary suites with custom tile bathrooms. Off street parking with no rental restrictions and no town taxes. Close to YMCA, school, restaurants, grocery stores, museums, and downtown shops. A wonderful place to settle in and enjoy the lifestyle that makes St. Michaels so special.

407 Seymour Ave, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$299,900

INVESTOR SPECIAL – PRIME IN-TOWN ST. MICHAELS OPPORTUNITY! Bring your contractor, vision, and renovation plans to 105 W Marengo St. This circa-1890 home offers approximately 1,656 square feet and presents an excellent value-add opportunity for an investor, renovator, or buyer looking for a substantial project in highly desirable St. Michaels. The property is ready for renovation, providing an opportunity to restore its character while updating the home for today's buyer. Whether your strategy is renovate and resell, hold as an investment, or create a distinctive personal residence, the location makes this one worth a serious look. Enjoy an in-town St. Michaels location convenient to downtown shops, restaurants, attractions, and the waterfront. Properties with renovation potential in established Eastern Shore destinations can be difficult to duplicate—here's an opportunity to improve the property from the ground up and make it your own. SOLD AS-IS. Seller will make no repairs. Cash, renovation financing, or other appropriate financing may be best suited for the property. Buyer to independently verify property condition, square footage, permits, zoning, and intended use.

3 Beds ⋅ 1 Baths

INVESTOR SPECIAL – PRIME IN-TOWN ST. MICHAELS OPPORTUNITY! Bring your contractor, vision, and renovation plans to 105 W Marengo St. This circa-1890 home offers approximately 1,656 square feet and presents an excellent value-add opportunity for an investor, renovator, or buyer looking for a substantial project in highly desirable St. Michaels. The property is ready for renovation, providing an opportunity to restore its character while updating the home for today's buyer. Whether your strategy is renovate and resell, hold as an investment, or create a distinctive personal residence, the location makes this one worth a serious look. Enjoy an in-town St. Michaels location convenient to downtown shops, restaurants, attractions, and the waterfront. Properties with renovation potential in established Eastern Shore destinations can be difficult to duplicate—here's an opportunity to improve the property from the ground up and make it your own. SOLD AS-IS. Seller will make no repairs. Cash, renovation financing, or other appropriate financing may be best suited for the property. Buyer to independently verify property condition, square footage, permits, zoning, and intended use.

105 Marengo St, St Michaels

Listing courtesy of Witz Realty, LLC. Contact:

$1,195,000

Experience the quintessential coastal lifestyle in this historic gem, situated on one of the most sought-after streets in the St. Michaels historic district. Featuring timeless charm and character, this stately property perfectly blends classic architectural details (such as multiple built-ins and four working fireplaces) with modern convenience, all just a stone's throw from the town's vibrant harbor, boutique shops, and award-winning restaurants. Enter from the wide, covered front porch - ideal for morning coffee or greeting neighbors - into a grand, elongated foyer that sets a welcoming tone. The interior features gorgeous hardwood floors throughout, seamlessly connecting the bright living spaces. This home offers four spacious bedrooms, generously sized bathrooms, and ample storage, providing comfort for family and guests alike. The rear yard is a private retreat designed for both relaxation and entertaining. Tucked into the lush landscaping (which includes an in-ground irrigation system) is a fully finished, detached accessory building. This versatile, light-filled structure is perfect for a dedicated craft studio, hobby workshop, private home office, or fitness room. This property also includes rare, highly coveted off-street parking. Situated just steps from San Domingo creek and less than a block from Talbot Street, the house provides quick access to the waterfront park/kayak launch and the nature trail as well to the town's maritime attractions, local ice cream parlors, and fine dining. An 1850 historic treasure in a premier in-town location doesn't come along often-schedule your private tour today and make the magic of the Eastern Shore your reality.

4 Beds ⋅ 4 Baths

Experience the quintessential coastal lifestyle in this historic gem, situated on one of the most sought-after streets in the St. Michaels historic district. Featuring timeless charm and character, this stately property perfectly blends classic architectural details (such as multiple built-ins and four working fireplaces) with modern convenience, all just a stone's throw from the town's vibrant harbor, boutique shops, and award-winning restaurants. Enter from the wide, covered front porch - ideal for morning coffee or greeting neighbors - into a grand, elongated foyer that sets a welcoming tone. The interior features gorgeous hardwood floors throughout, seamlessly connecting the bright living spaces. This home offers four spacious bedrooms, generously sized bathrooms, and ample storage, providing comfort for family and guests alike. The rear yard is a private retreat designed for both relaxation and entertaining. Tucked into the lush landscaping (which includes an in-ground irrigation system) is a fully finished, detached accessory building. This versatile, light-filled structure is perfect for a dedicated craft studio, hobby workshop, private home office, or fitness room. This property also includes rare, highly coveted off-street parking. Situated just steps from San Domingo creek and less than a block from Talbot Street, the house provides quick access to the waterfront park/kayak launch and the nature trail as well to the town's maritime attractions, local ice cream parlors, and fine dining. An 1850 historic treasure in a premier in-town location doesn't come along often-schedule your private tour today and make the magic of the Eastern Shore your reality.

114 W Chestnut St, St Michaels

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

$459,900

This well-maintained duplex with new roof 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.

4 Beds ⋅ 4 Baths

This well-maintained duplex with new roof 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

$339,900

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.

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

$695,000

NEW PRICE!! 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.

3 Beds ⋅ 2 Baths

NEW PRICE!! 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: