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Discover a prime investment opportunity in the desirable St. Michaels community. This 3-bedroom, 2-bathroom ranch-style home, built in 1960, boasts a spacious 1,340 sq. ft. of potential. With its classic vinyl siding, this property is ready for some TLA and future enhancements. The roof is less than 5 years old and layout offers flexibility, making it easy to adapt the space. The 0.17-acre lot provides ample outdoor space for potential landscaping or recreational activities, enhancing the property's appeal. Homeowners or Investors will appreciate the potential to transform this property into your personal residence or investment property. Being sold As Is condition.

3 Beds ⋅ 2 Baths

Discover a prime investment opportunity in the desirable St. Michaels community. This 3-bedroom, 2-bathroom ranch-style home, built in 1960, boasts a spacious 1,340 sq. ft. of potential. With its classic vinyl siding, this property is ready for some TLA and future enhancements. The roof is less than 5 years old and layout offers flexibility, making it easy to adapt the space. The 0.17-acre lot provides ample outdoor space for potential landscaping or recreational activities, enhancing the property's appeal. Homeowners or Investors will appreciate the potential to transform this property into your personal residence or investment property. Being sold As Is condition.

210 Brooks Ln, St Michaels

Listing courtesy of Meredith Fine Properties. Contact:

$525,000

Located in Bentley Hay and within walking distance of Historic St. Michaels, this charming cottage would make an exceptional pied-à-terre. Enjoy two bedrooms and two bathrooms on separate levels, with tremendous privacy and rear alley access. Easy access to nearby parks is perfect for leisurely strolls. Convenient public services and amenities are just a stone's throw away, making daily errands a breeze. Whether you're exploring local shops or enjoying a meal nearby, you'll find everything you need within reach.

2 Beds ⋅ 2 Baths

Located in Bentley Hay and within walking distance of Historic St. Michaels, this charming cottage would make an exceptional pied-à-terre. Enjoy two bedrooms and two bathrooms on separate levels, with tremendous privacy and rear alley access. Easy access to nearby parks is perfect for leisurely strolls. Convenient public services and amenities are just a stone's throw away, making daily errands a breeze. Whether you're exploring local shops or enjoying a meal nearby, you'll find everything you need within reach.

806 Calvert Ave, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

$329,000

This property has been gutted and the floor joists replaced, new Advantac subfloor installed, drywall removed, new interior framing, new roof, insulation, new electric and a new sewer line to the street.. The hard work has been done. It's ready for you to make it your own. Off street parking and large rear yard. Please be careful showing as there is still building materials on the property.

3 Beds ⋅ 2 Baths

This property has been gutted and the floor joists replaced, new Advantac subfloor installed, drywall removed, new interior framing, new roof, insulation, new electric and a new sewer line to the street.. The hard work has been done. It's ready for you to make it your own. Off street parking and large rear yard. Please be careful showing as there is still building materials on the property.

409 Railroad Ave, St Michaels

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

$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:

$525,000

**OPEN HOUSE, Saturday, 10/10, 10:00am - Noon** Priced to Sell - Huge Price Improvement! Your St. Michaels weekend escape may be more attainable than you think. Trade the traffic and weekly routine for weekends in one of the Eastern Shore’s most beloved waterfront towns. 204 E Marengo Street offers the perfect combination of location, low-maintenance living, and your own private backyard oasis—ideal as a weekend retreat or primary home. Located just outside the Historic District and approximately 1.5 blocks from water access, including a marina and public boat ramp, this move-in-ready cottage puts restaurants, coffee shops, boutiques, waterfront parks, marinas, and all the charm of St. Michaels within easy reach. Inside, enjoy bright, inviting spaces, convenient main-level living, an updated bathroom, and numerous improvements. Major updates include a new roof (2024), upgraded crawl space with French drain, insulation, and vapor barrier (2025), updated plumbing (2025), Thompson Creek windows, HVAC and water heater (2018), plus updated appliances and plantation shutters —meaning less time on projects and more time enjoying the Shore. Outside is where weekends really begin. Spend summer afternoons by the in-ground pool, entertain friends at the beach-inspired outdoor bar with cable TV, or simply unwind after a day on the water. The detached garage with electric offers additional space for bikes, kayaks, water toys, and weekend gear. And because the property is outside the Historic District, you'll have greater flexibility for future improvements without Historic District oversight. Come for the weekends and stay for the lifestyle. Whether you're looking for a primary home, weekend getaway, or your own place to escape and recharge, 204 E Marengo Street is ready to enjoy from day one.

2 Beds ⋅ 1 Baths

**OPEN HOUSE, Saturday, 10/10, 10:00am - Noon** Priced to Sell - Huge Price Improvement! Your St. Michaels weekend escape may be more attainable than you think. Trade the traffic and weekly routine for weekends in one of the Eastern Shore’s most beloved waterfront towns. 204 E Marengo Street offers the perfect combination of location, low-maintenance living, and your own private backyard oasis—ideal as a weekend retreat or primary home. Located just outside the Historic District and approximately 1.5 blocks from water access, including a marina and public boat ramp, this move-in-ready cottage puts restaurants, coffee shops, boutiques, waterfront parks, marinas, and all the charm of St. Michaels within easy reach. Inside, enjoy bright, inviting spaces, convenient main-level living, an updated bathroom, and numerous improvements. Major updates include a new roof (2024), upgraded crawl space with French drain, insulation, and vapor barrier (2025), updated plumbing (2025), Thompson Creek windows, HVAC and water heater (2018), plus updated appliances and plantation shutters —meaning less time on projects and more time enjoying the Shore. Outside is where weekends really begin. Spend summer afternoons by the in-ground pool, entertain friends at the beach-inspired outdoor bar with cable TV, or simply unwind after a day on the water. The detached garage with electric offers additional space for bikes, kayaks, water toys, and weekend gear. And because the property is outside the Historic District, you'll have greater flexibility for future improvements without Historic District oversight. Come for the weekends and stay for the lifestyle. Whether you're looking for a primary home, weekend getaway, or your own place to escape and recharge, 204 E Marengo Street is ready to enjoy from day one.

204 E Marengo St, Saint Michaels

Listing courtesy of Compass. Contact:

$775,000

PUBLIC OPEN HOUSE SUNDAY 10/11 FROM 1-3PM ***BRAND NEW & MOVE-IN READY*** this Arts & Crafts home sits on a quaint corner lot in picturesque Saint Michaels, MD and is clad with high end finishes throughout. Step from the covered front porch into the luxurious kitchen which features stylish pistachio and linen cabinetry with satin bronze hardware, Z-Line appliances including a 36" dual fuel 6 burner range with champagne bronze accessories, artisan wood range hood, spacious center island w/breakfast bar, high end d'oro quartz countertops and herringbone tile backsplash. The living room includes a gas fireplace w/shiplap surround, custom coffered ceiling, large picture windows and a four panel Pella slider door which allows abundance of natural light and direct access to the backyard. Rounding out the main level is a flexible multi-purpose space - perfect for a formal dining room, office or a sitting room. On the upper level enjoy 3 bedrooms and two baths, including an owner's suite with walk-in closet and a luxurious spa-like bath with dual vanities, rich blue cabinetry and walk-in shower with dual shower heads and floor-to-ceiling attache calacatta tile. Additional amenities include LVP flooring throughout main level, ceramic or porcelain tile in all baths, custom light fixtures, public water and sewer, 30 year architectural singles, 92% efficient Carrier HVAC, Pella windows, 2x6 framing, R49 insulation in ceiling, R21 insulation in walls, air seal package, covered front porch and much more. All of this in a convenient location adjacent to all historic Saint Michaels has to offer. Loaded with amenities and unbound by an HOA or restrictive covenants, this one of a kind property will not last long! Schedule your private tour today!

3 Beds ⋅ 3 Baths

PUBLIC OPEN HOUSE SUNDAY 10/11 FROM 1-3PM ***BRAND NEW & MOVE-IN READY*** this Arts & Crafts home sits on a quaint corner lot in picturesque Saint Michaels, MD and is clad with high end finishes throughout. Step from the covered front porch into the luxurious kitchen which features stylish pistachio and linen cabinetry with satin bronze hardware, Z-Line appliances including a 36" dual fuel 6 burner range with champagne bronze accessories, artisan wood range hood, spacious center island w/breakfast bar, high end d'oro quartz countertops and herringbone tile backsplash. The living room includes a gas fireplace w/shiplap surround, custom coffered ceiling, large picture windows and a four panel Pella slider door which allows abundance of natural light and direct access to the backyard. Rounding out the main level is a flexible multi-purpose space - perfect for a formal dining room, office or a sitting room. On the upper level enjoy 3 bedrooms and two baths, including an owner's suite with walk-in closet and a luxurious spa-like bath with dual vanities, rich blue cabinetry and walk-in shower with dual shower heads and floor-to-ceiling attache calacatta tile. Additional amenities include LVP flooring throughout main level, ceramic or porcelain tile in all baths, custom light fixtures, public water and sewer, 30 year architectural singles, 92% efficient Carrier HVAC, Pella windows, 2x6 framing, R49 insulation in ceiling, R21 insulation in walls, air seal package, covered front porch and much more. All of this in a convenient location adjacent to all historic Saint Michaels has to offer. Loaded with amenities and unbound by an HOA or restrictive covenants, this one of a kind property will not last long! Schedule your private tour today!

807 Radcliff Ave, Saint Michaels

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