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Charming Cape Cod in the Heart of St. Michaels Welcome to this beautifully maintained Cape Cod in the heart of St. Michaels, where newer construction, timeless charm, and exceptional indoor-outdoor living come together in a truly special property. Built in 2019, this inviting home features three generously sized bedrooms, two full bathrooms, and one half bath, with beautiful hardwood flooring throughout. Meticulously maintained and move-in ready, the home offers the comfort and quality of a newer home with the character and warmth of a classic Cape Cod. The outdoor living space is truly exceptional. Step onto the large deck, perfect for entertaining family and friends, and enjoy a private backyard that backs to peaceful woods. Gather around the fire pit, relax with a drink at your own tiki bar, or simply enjoy the tranquility of the wooded setting. It's an ideal space for summer entertaining, weekend gatherings, or quiet evenings at home. And then there's the location. Situated within walking distance of downtown St. Michaels, you can easily leave the car behind and enjoy the town's wonderful restaurants, shops, waterfront, and attractions. Few properties offer this combination of privacy and convenient in-town living. Inside, the home offers spacious bedrooms, three bathrooms, hardwood floors, and the peace of mind that comes with a 2019 build. Whether you're looking for a full-time residence, weekend retreat, or Eastern Shore getaway, this home offers an exceptional opportunity to enjoy the St. Michaels lifestyle. Property Highlights Built in 2019 3 large bedrooms 2 full bathrooms + 1 half bath Beautiful hardwood flooring throughout Beautifully maintained and move-in ready Large deck designed for entertaining Private backyard backing to woods Outdoor tiki bar Fire pit Excellent indoor-outdoor entertaining space Walk to downtown St. Michaels Close to restaurants, shops, waterfront, and attractions Rare combination of in-town convenience and private wooded setting Come discover a home where entertaining comes naturally, privacy is preserved, and the best of St. Michaels is just a short walk away. This home is also for Rent on MLS MDTA2015258

3 Beds ⋅ 3 Baths

Charming Cape Cod in the Heart of St. Michaels Welcome to this beautifully maintained Cape Cod in the heart of St. Michaels, where newer construction, timeless charm, and exceptional indoor-outdoor living come together in a truly special property. Built in 2019, this inviting home features three generously sized bedrooms, two full bathrooms, and one half bath, with beautiful hardwood flooring throughout. Meticulously maintained and move-in ready, the home offers the comfort and quality of a newer home with the character and warmth of a classic Cape Cod. The outdoor living space is truly exceptional. Step onto the large deck, perfect for entertaining family and friends, and enjoy a private backyard that backs to peaceful woods. Gather around the fire pit, relax with a drink at your own tiki bar, or simply enjoy the tranquility of the wooded setting. It's an ideal space for summer entertaining, weekend gatherings, or quiet evenings at home. And then there's the location. Situated within walking distance of downtown St. Michaels, you can easily leave the car behind and enjoy the town's wonderful restaurants, shops, waterfront, and attractions. Few properties offer this combination of privacy and convenient in-town living. Inside, the home offers spacious bedrooms, three bathrooms, hardwood floors, and the peace of mind that comes with a 2019 build. Whether you're looking for a full-time residence, weekend retreat, or Eastern Shore getaway, this home offers an exceptional opportunity to enjoy the St. Michaels lifestyle. Property Highlights Built in 2019 3 large bedrooms 2 full bathrooms + 1 half bath Beautiful hardwood flooring throughout Beautifully maintained and move-in ready Large deck designed for entertaining Private backyard backing to woods Outdoor tiki bar Fire pit Excellent indoor-outdoor entertaining space Walk to downtown St. Michaels Close to restaurants, shops, waterfront, and attractions Rare combination of in-town convenience and private wooded setting Come discover a home where entertaining comes naturally, privacy is preserved, and the best of St. Michaels is just a short walk away. This home is also for Rent on MLS MDTA2015258

207 Brooks Ln, St Michaels

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

$279,000

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:

9521 Quail Hollow Dr Unit 605, St Michaels

$490,000

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:

$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:

$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:

$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:

9531 Quail Hollow Dr Unit 405, St Michaels

$319,900

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: