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Come see a true Eastern Shore gem, set on 20 peaceful waterfront acres along Edge Creek. This beautifully renovated 4-bedroom, 4-bathroom home features all the hallmarks of a coastal getaway while providing modern, functional conveniences. Walk through the front door, and you’re met with direct water views that can be seen from virtually every room in the home. You’ll also find natural light that fills every space due to the ample window and sliding glass door installations, coupled with southwestern exposure off the back of the home. Make your way over to the well-appointed, fully renovated kitchen featuring Miele appliances. Around the corner is a first-floor primary suite with direct waterfront views, his-and-hers sink vanities, a spacious walk-in closet system with built-ins, and one of the home’s three fireplaces. Upstairs, you’ll find plenty of space for guests, including a bedroom featuring built-in bunks. On the third floor is a bonus loft area with twin walkout balconies. Across the driveway is a detached garage with two car bays, a workshop, and a storage area. Above the garage, you’ll find a separate in-law suite or apartment space with a living area, bedroom, full bathroom, and kitchenette. Around the back of the home is an entertaining space that makes for the perfect Eastern Shore weekend. A beautifully done gunite pool overlooks your 1,600 feet of shoreline. A private dock with a boat lift (insert weight capacity) provides easy access for an afternoon cruise or evening fishing expedition. With privacy from your neighbors and close proximity to historic downtown St. Michaels, this home provides the ultimate secluded Chesapeake Bay oasis.

4 Beds ⋅ 4 Baths

Come see a true Eastern Shore gem, set on 20 peaceful waterfront acres along Edge Creek. This beautifully renovated 4-bedroom, 4-bathroom home features all the hallmarks of a coastal getaway while providing modern, functional conveniences. Walk through the front door, and you’re met with direct water views that can be seen from virtually every room in the home. You’ll also find natural light that fills every space due to the ample window and sliding glass door installations, coupled with southwestern exposure off the back of the home. Make your way over to the well-appointed, fully renovated kitchen featuring Miele appliances. Around the corner is a first-floor primary suite with direct waterfront views, his-and-hers sink vanities, a spacious walk-in closet system with built-ins, and one of the home’s three fireplaces. Upstairs, you’ll find plenty of space for guests, including a bedroom featuring built-in bunks. On the third floor is a bonus loft area with twin walkout balconies. Across the driveway is a detached garage with two car bays, a workshop, and a storage area. Above the garage, you’ll find a separate in-law suite or apartment space with a living area, bedroom, full bathroom, and kitchenette. Around the back of the home is an entertaining space that makes for the perfect Eastern Shore weekend. A beautifully done gunite pool overlooks your 1,600 feet of shoreline. A private dock with a boat lift (insert weight capacity) provides easy access for an afternoon cruise or evening fishing expedition. With privacy from your neighbors and close proximity to historic downtown St. Michaels, this home provides the ultimate secluded Chesapeake Bay oasis.

7116 Pea Neck Rd, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

$5,750,000

Pine Point Farm is a remarkable 77+ acre waterfront estate on the scenic shores of Broad Creek comprising 4 total bedrooms, 4 full baths, and two half baths, and offering an exceptional combination of privacy, natural beauty, waterfront amenities, and newly constructed improvements. Built in 2023, the coastal-style main residence features an inviting open-concept kitchen, dining, and family room with beamed, vaulted ceilings and a wood-burning fireplace. Multiple sliders and doors open to the spacious rear deck and a screened-in porch, creating a seamless connection between the interior and the surrounding landscape while taking full advantage of the water views. The main house includes two en-suite bedrooms, an office/den, and a powder room, along with hardwood flooring throughout, and numerous built-ins. Also completed in 2023, the guest house and attached two-car garage are connected to the main residence by a breezeway. The guest house offers a large living room, kitchenette, and full bath on the main level, with two spacious bedrooms and a large hall bath upstairs. This thoughtfully designed space is ideal for guests, extended family, or a private retreat. The outdoor amenities are equally impressive. A large, stocked pond is home to hybrid bass, largemouth bass, and bluegill, offering a private setting for fishing and recreation. Along Broad Creek, the substantial dock features water and electric, approximately 3.5 feet mean low water, a boat lift, and multiple slips, providing excellent access for boating and waterfront activities. Additional improvements include a large block outbuilding ideal for equipment, storage, hobbies, or workshop use; an in-ground pool; irrigation system; and two generators. The sale includes a separate 0.146-acre waterfront lot on Harris Creek, and two additional, platted waterfront lots, providing more possibilities for the new owner. (Please note there is potentially an Eagles' Nest on the property). Pine Point Farm is a truly exceptional waterfront estate, combining 77+ acres, two newly constructed residences, extensive waterfront amenities, recreational features, and remarkable privacy—all in one extraordinary offering.

2 Beds ⋅ 3 Baths

Pine Point Farm is a remarkable 77+ acre waterfront estate on the scenic shores of Broad Creek comprising 4 total bedrooms, 4 full baths, and two half baths, and offering an exceptional combination of privacy, natural beauty, waterfront amenities, and newly constructed improvements. Built in 2023, the coastal-style main residence features an inviting open-concept kitchen, dining, and family room with beamed, vaulted ceilings and a wood-burning fireplace. Multiple sliders and doors open to the spacious rear deck and a screened-in porch, creating a seamless connection between the interior and the surrounding landscape while taking full advantage of the water views. The main house includes two en-suite bedrooms, an office/den, and a powder room, along with hardwood flooring throughout, and numerous built-ins. Also completed in 2023, the guest house and attached two-car garage are connected to the main residence by a breezeway. The guest house offers a large living room, kitchenette, and full bath on the main level, with two spacious bedrooms and a large hall bath upstairs. This thoughtfully designed space is ideal for guests, extended family, or a private retreat. The outdoor amenities are equally impressive. A large, stocked pond is home to hybrid bass, largemouth bass, and bluegill, offering a private setting for fishing and recreation. Along Broad Creek, the substantial dock features water and electric, approximately 3.5 feet mean low water, a boat lift, and multiple slips, providing excellent access for boating and waterfront activities. Additional improvements include a large block outbuilding ideal for equipment, storage, hobbies, or workshop use; an in-ground pool; irrigation system; and two generators. The sale includes a separate 0.146-acre waterfront lot on Harris Creek, and two additional, platted waterfront lots, providing more possibilities for the new owner. (Please note there is potentially an Eagles' Nest on the property). Pine Point Farm is a truly exceptional waterfront estate, combining 77+ acres, two newly constructed residences, extensive waterfront amenities, recreational features, and remarkable privacy—all in one extraordinary offering.

23505 Pine Point Rd, Bozman

Listing courtesy of Meredith Fine Properties. Contact:

$1,350,000

Waterfront coastal cottage living at its finest. Come see what makes this 3-bedroom, 2.5-bathroom retreat feel like a secluded getaway, approximately 10 minutes from downtown St. Michaels and two hours from the DC, and Baltimore areas. Set on 16.45 peaceful acres on Leadenham Creek, this property offers southwestern exposure and over 900 feet of shoreline. Sit back and enjoy evening sunset views from the newly installed dock (2025). Two sheds on the property, provide additional storage capability. Step inside to find a cozy, open-concept layout. The kitchen flows directly into a breakfast nook/dining area with built-in seating and an adjoining living room with a wood-burning fireplace, all with waterfront views. On the main level, you’ll find a primary bedroom suite with a full bathroom and access to a bright, private sunroom. A spiral staircase leads to two additional bedrooms. Additional updates include a new HVAC system (2022) and a new roof (2021). Privacy, waterfront, and acreage, all within a short drive of the restaurants, shops, museums, and activities St. Michaels has to offer.

3 Beds ⋅ 3 Baths

Waterfront coastal cottage living at its finest. Come see what makes this 3-bedroom, 2.5-bathroom retreat feel like a secluded getaway, approximately 10 minutes from downtown St. Michaels and two hours from the DC, and Baltimore areas. Set on 16.45 peaceful acres on Leadenham Creek, this property offers southwestern exposure and over 900 feet of shoreline. Sit back and enjoy evening sunset views from the newly installed dock (2025). Two sheds on the property, provide additional storage capability. Step inside to find a cozy, open-concept layout. The kitchen flows directly into a breakfast nook/dining area with built-in seating and an adjoining living room with a wood-burning fireplace, all with waterfront views. On the main level, you’ll find a primary bedroom suite with a full bathroom and access to a bright, private sunroom. A spiral staircase leads to two additional bedrooms. Additional updates include a new HVAC system (2022) and a new roof (2021). Privacy, waterfront, and acreage, all within a short drive of the restaurants, shops, museums, and activities St. Michaels has to offer.

7582 Leadenham Cove Rd, Bozman

Listing courtesy of Benson & Mangold, LLC. Contact:

$499,000

Embrace an effortless coastal lifestyle in the heart of Oxford, where days are shaped by the water and some of the town’s most beloved destinations are just a short stroll from home. Ideally located near beach access, waterfront dining, marinas, tennis and pickleball courts, and a local church, this beautifully refreshed cottage offers a rare combination of walkability, privacy, and Eastern Shore charm. Set on a generous 16,988+/- square foot lot, the 1,200+/- square foot, two bedroom, two full bath residence has been thoughtfully updated with a fresh coastal sensibility. The remodeled kitchen features new stainless steel appliances, while renovated baths, new luxury vinyl plank flooring throughout, windows and doors, custom window treatments, and efficient ductless heating and cooling create a polished, comfortable interior designed for easy living. A wooden deck extends the living space outdoors, providing a relaxed setting for morning coffee, meals with friends and family, and evening relaxation after a day on the water. The grounds offer room to entertain and enjoy the outdoors, complemented by ample parking and a two story outbuilding with electricity, offering potential with exceptional storage and versatility. Additional improvements include a new hot water heater and French drain installation, while affordable utility costs add to the home’s low maintenance appeal. A history of short term rental income provides additional flexibility for buyers seeking a coastal retreat with income potential. What truly distinguishes this property is its location. From 705 S. Morris Street, the waterfront lifestyle of Oxford is within easy reach. Walk to the beach, stroll to enjoy dinner overlooking the river, head to the marina for an afternoon on the Chesapeake, or spend the morning on the tennis and pickleball courts and many walking paths. Situated in sought after Talbot County, Oxford offers the understated elegance and slower pace that have long made Maryland’s Eastern Shore a coveted destination. Conveniently positioned between Washington, D.C. and the Atlantic Ocean, this inviting cottage presents an opportunity to enjoy a refined yet relaxed coastal escape in one of the Shore’s most charming waterfront towns.

2 Beds ⋅ 2 Baths

Embrace an effortless coastal lifestyle in the heart of Oxford, where days are shaped by the water and some of the town’s most beloved destinations are just a short stroll from home. Ideally located near beach access, waterfront dining, marinas, tennis and pickleball courts, and a local church, this beautifully refreshed cottage offers a rare combination of walkability, privacy, and Eastern Shore charm. Set on a generous 16,988+/- square foot lot, the 1,200+/- square foot, two bedroom, two full bath residence has been thoughtfully updated with a fresh coastal sensibility. The remodeled kitchen features new stainless steel appliances, while renovated baths, new luxury vinyl plank flooring throughout, windows and doors, custom window treatments, and efficient ductless heating and cooling create a polished, comfortable interior designed for easy living. A wooden deck extends the living space outdoors, providing a relaxed setting for morning coffee, meals with friends and family, and evening relaxation after a day on the water. The grounds offer room to entertain and enjoy the outdoors, complemented by ample parking and a two story outbuilding with electricity, offering potential with exceptional storage and versatility. Additional improvements include a new hot water heater and French drain installation, while affordable utility costs add to the home’s low maintenance appeal. A history of short term rental income provides additional flexibility for buyers seeking a coastal retreat with income potential. What truly distinguishes this property is its location. From 705 S. Morris Street, the waterfront lifestyle of Oxford is within easy reach. Walk to the beach, stroll to enjoy dinner overlooking the river, head to the marina for an afternoon on the Chesapeake, or spend the morning on the tennis and pickleball courts and many walking paths. Situated in sought after Talbot County, Oxford offers the understated elegance and slower pace that have long made Maryland’s Eastern Shore a coveted destination. Conveniently positioned between Washington, D.C. and the Atlantic Ocean, this inviting cottage presents an opportunity to enjoy a refined yet relaxed coastal escape in one of the Shore’s most charming waterfront towns.

705 S Morris St, Oxford

Listing courtesy of Meredith Fine Properties. Contact:

$724,900

Beautifully crafted, turn-key "Oxford Cottage" built in 2023 offering high-end finishes and classic Eastern Shore charm with NO HOA! Step off the welcoming front porch into a light-filled open-concept main level featuring hardwood floors throughout. The generous-sized eat-in kitchen boasts custom cabinetry, upgraded countertops, stainless steel appliances, and a seamless transition out to a spacious screened-in sunroom—ideal for outdoor dining and entertaining. The main floor offers an entry-level full bath and a versatile flex room perfect for a primary bedroom, home office, or den. Upstairs features two generous-sized bedrooms with dramatic vaulted ceilings, a full bath, and a dedicated laundry area. Outside, cedar-raised flower beds frame the home alongside a low-maintenance 0.11-acre lot and a detached frame garage with ample room for vehicles, water toys, or a workshop. Located just blocks from the Strand beach, waterfront parks, local dockside dining, the historic Oxford-Bellevue Ferry, and the Scottish Highland Creamery!

3 Beds ⋅ 2 Baths

Beautifully crafted, turn-key "Oxford Cottage" built in 2023 offering high-end finishes and classic Eastern Shore charm with NO HOA! Step off the welcoming front porch into a light-filled open-concept main level featuring hardwood floors throughout. The generous-sized eat-in kitchen boasts custom cabinetry, upgraded countertops, stainless steel appliances, and a seamless transition out to a spacious screened-in sunroom—ideal for outdoor dining and entertaining. The main floor offers an entry-level full bath and a versatile flex room perfect for a primary bedroom, home office, or den. Upstairs features two generous-sized bedrooms with dramatic vaulted ceilings, a full bath, and a dedicated laundry area. Outside, cedar-raised flower beds frame the home alongside a low-maintenance 0.11-acre lot and a detached frame garage with ample room for vehicles, water toys, or a workshop. Located just blocks from the Strand beach, waterfront parks, local dockside dining, the historic Oxford-Bellevue Ferry, and the Scottish Highland Creamery!

101 Tilghman St, Oxford

Listing courtesy of The Parker Group. Contact:

$2,995,000

With huge sunset views across Eastern Bay, this stylishly-updated property is the perfect retreat! The main house with three en-suite bedrooms overlooks a large waterside deck, saltwater pool and screened pool house. A wisteria-covered pergola leads the the 1920's two-bedroom guest house with wrap-around porch at the water's edge. The one-bedroom carriage house completes the compound. Great elevation, substantial dock with 4' MLW and heavy-duty rip rap, newer septic. And all just five miles from historic St. Michaels.

6 Beds ⋅ 7 Baths

With huge sunset views across Eastern Bay, this stylishly-updated property is the perfect retreat! The main house with three en-suite bedrooms overlooks a large waterside deck, saltwater pool and screened pool house. A wisteria-covered pergola leads the the 1920's two-bedroom guest house with wrap-around porch at the water's edge. The one-bedroom carriage house completes the compound. Great elevation, substantial dock with 4' MLW and heavy-duty rip rap, newer septic. And all just five miles from historic St. Michaels.

1002 Wades Farm Ln, Mcdaniel

Listing courtesy of Benson & Mangold, LLC. Contact:

$1,250,000

Welcome to the William J. Wrightson House, a beautifully restored c. 1897 residence where historic St. Michaels charm meets exceptional modern comfort. Located in the heart of town and just steps from the waterfront, marinas, shops, and restaurants, this distinctive 3-bedroom, 3-bath home offers an extraordinary opportunity to enjoy the very best of Eastern Shore living. Extensively renovated with an emphasis on quality and craftsmanship, the home has been updated from top to bottom. Improvements include new HVAC systems, tankless hot water heaters, updated wiring, encapsulated crawl space, new roof and gutters, recessed lighting, high-end appliances, three renovated baths, a custom butler’s pantry, complete interior and exterior painting, and improved patio drainage and grading. Natural light fills the gracious interior, highlighting heart pine and yellow pine floors, custom millwork, and beautifully appointed living spaces. The living room, anchored by a new gas fireplace, flows naturally into the formal dining room and gourmet kitchen, which features quartz countertops, top-tier appliances, generous cabinetry, and custom built-ins. At the rear of the home, the extraordinary sunroom overlooking the English garden, provides an inviting space for relaxed gatherings or entertaining. Vaulted ceilings, shiplap wall treatment, custom built-ins, and butler’s pantry with beverage chiller and bar sink make this room the heart of the house. French doors open to the brick patio and beautifully landscaped gardens. The second floor offers a serene primary suite with a luxurious marble bath, clawfoot soaking tub, antique vanity, and glass-enclosed walk-in shower. Two additional bedrooms and a beautifully renovated hall bath provide comfortable accommodations for family and guests. Outside, a private English garden creates a picturesque retreat, with roses, crepe myrtles, and hydrangeas framed by a charming French Gothic lattice shadowbox fence. Beautifully restored, thoughtfully designed, and ideally located, this is historic St. Michaels living at its finest.

3 Beds ⋅ 3 Baths

Welcome to the William J. Wrightson House, a beautifully restored c. 1897 residence where historic St. Michaels charm meets exceptional modern comfort. Located in the heart of town and just steps from the waterfront, marinas, shops, and restaurants, this distinctive 3-bedroom, 3-bath home offers an extraordinary opportunity to enjoy the very best of Eastern Shore living. Extensively renovated with an emphasis on quality and craftsmanship, the home has been updated from top to bottom. Improvements include new HVAC systems, tankless hot water heaters, updated wiring, encapsulated crawl space, new roof and gutters, recessed lighting, high-end appliances, three renovated baths, a custom butler’s pantry, complete interior and exterior painting, and improved patio drainage and grading. Natural light fills the gracious interior, highlighting heart pine and yellow pine floors, custom millwork, and beautifully appointed living spaces. The living room, anchored by a new gas fireplace, flows naturally into the formal dining room and gourmet kitchen, which features quartz countertops, top-tier appliances, generous cabinetry, and custom built-ins. At the rear of the home, the extraordinary sunroom overlooking the English garden, provides an inviting space for relaxed gatherings or entertaining. Vaulted ceilings, shiplap wall treatment, custom built-ins, and butler’s pantry with beverage chiller and bar sink make this room the heart of the house. French doors open to the brick patio and beautifully landscaped gardens. The second floor offers a serene primary suite with a luxurious marble bath, clawfoot soaking tub, antique vanity, and glass-enclosed walk-in shower. Two additional bedrooms and a beautifully renovated hall bath provide comfortable accommodations for family and guests. Outside, a private English garden creates a picturesque retreat, with roses, crepe myrtles, and hydrangeas framed by a charming French Gothic lattice shadowbox fence. Beautifully restored, thoughtfully designed, and ideally located, this is historic St. Michaels living at its finest.

202 E Chestnut St, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

$1,500,000

A stunning Farmhouse completely restored/rebuilt by renown Architect Greg Wiedemann on two glorious acres meticulously maintained on a serene Choptank River Setting. it is the Quintessential "Getaway" from the hustle/bustle of life. The focus of each room is the River. There are patios, balconies and porches galore for your leisure enjoyment and viewing pleasure. The center of the home is the Dining and Kitchen area. You enter from the side porch and exit through either twin glass doors which border large windows which overlook the River onto a flagstone patio where you can enjoy outdoor dining or just relaxing by the River. Off of the Kitchen you will find the "Mud Room" and/or Laundry Room. You will find a stackable Washer Dryer and Utility Sink in this area. Also next to the Laundry room you will find a large full bath with shower. The actual Front Door to the home is on the side of the house off of the welcoming porch with a swing. The Main entrance opens to the Living Room with Large windows which front to the Choptank. One of the four bedrooms in the home is on the first floor with a large ensuite bath, There are actually two large primary bedrooms. One can use the primary bedroom on the first floor for a large family room as the upstairs bedrooms are very spacious. The second floor primary enjoys both a balcony and a screened porch. The home is in excellent condition. The two zone air conditioning systems have just been replaced. On the grounds you will find two sheds, one for utilities and the other serves as a Workshop and storage, Enjoy a 1000 foot private beach front with a dock. Within the photos, please take the time to gaze upon the variety of seasonal trees and flowering plants that adorn this two acre paradise.

4 Beds ⋅ 3 Baths

A stunning Farmhouse completely restored/rebuilt by renown Architect Greg Wiedemann on two glorious acres meticulously maintained on a serene Choptank River Setting. it is the Quintessential "Getaway" from the hustle/bustle of life. The focus of each room is the River. There are patios, balconies and porches galore for your leisure enjoyment and viewing pleasure. The center of the home is the Dining and Kitchen area. You enter from the side porch and exit through either twin glass doors which border large windows which overlook the River onto a flagstone patio where you can enjoy outdoor dining or just relaxing by the River. Off of the Kitchen you will find the "Mud Room" and/or Laundry Room. You will find a stackable Washer Dryer and Utility Sink in this area. Also next to the Laundry room you will find a large full bath with shower. The actual Front Door to the home is on the side of the house off of the welcoming porch with a swing. The Main entrance opens to the Living Room with Large windows which front to the Choptank. One of the four bedrooms in the home is on the first floor with a large ensuite bath, There are actually two large primary bedrooms. One can use the primary bedroom on the first floor for a large family room as the upstairs bedrooms are very spacious. The second floor primary enjoys both a balcony and a screened porch. The home is in excellent condition. The two zone air conditioning systems have just been replaced. On the grounds you will find two sheds, one for utilities and the other serves as a Workshop and storage, Enjoy a 1000 foot private beach front with a dock. Within the photos, please take the time to gaze upon the variety of seasonal trees and flowering plants that adorn this two acre paradise.

31720 Ayres Dr, Trappe

Listing courtesy of Weichert, REALTORS. Contact:

$325,000

Charming Cape Cod Near Historic Downtown Easton Warm, welcoming, and full of character, this beautifully updated Cape Cod offers comfortable living spaces and a wonderful location just a short stroll from historic downtown Easton. Inside, beautiful hardwood floors add warmth and character, while the bright, inviting kitchen and updated HVAC provide everyday comfort. The spacious second level offers exceptional flexibility with a large bedroom, separate office or sitting area, walk-in closet, and abundant additional storage, ideal for a home office, reading nook, hobby space, or quiet retreat. Outdoor living is just as inviting. Enjoy morning coffee or watch the world go by from the classic front porch and porch swing. In the beautifully landscaped backyard, a newer deck and patio provide plenty of space for outdoor dining, entertaining, gardening, or simply relaxing. A large storage shed with attic space offers excellent additional storage for bikes, tools, hobbies, and seasonal items. Best of all is the location. Downtown Easton’s restaurants, boutiques, galleries, and year-round events are close at hand, with parks, shopping, schools, and major routes conveniently nearby. Move-in ready, full of charm, and close to the heart of Easton, come take another look and see all this home has to offer. Advance notice required for showings - please contact your agent to schedule your appointment.

2 Beds ⋅ 1 Baths

Charming Cape Cod Near Historic Downtown Easton Warm, welcoming, and full of character, this beautifully updated Cape Cod offers comfortable living spaces and a wonderful location just a short stroll from historic downtown Easton. Inside, beautiful hardwood floors add warmth and character, while the bright, inviting kitchen and updated HVAC provide everyday comfort. The spacious second level offers exceptional flexibility with a large bedroom, separate office or sitting area, walk-in closet, and abundant additional storage, ideal for a home office, reading nook, hobby space, or quiet retreat. Outdoor living is just as inviting. Enjoy morning coffee or watch the world go by from the classic front porch and porch swing. In the beautifully landscaped backyard, a newer deck and patio provide plenty of space for outdoor dining, entertaining, gardening, or simply relaxing. A large storage shed with attic space offers excellent additional storage for bikes, tools, hobbies, and seasonal items. Best of all is the location. Downtown Easton’s restaurants, boutiques, galleries, and year-round events are close at hand, with parks, shopping, schools, and major routes conveniently nearby. Move-in ready, full of charm, and close to the heart of Easton, come take another look and see all this home has to offer. Advance notice required for showings - please contact your agent to schedule your appointment.

347 N Washington St, Easton

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

$525,000

Just reduced to $525,000—affordable, turn-key easy living near the water in St. Michaels. Located 1.5 blocks from public boat ramps and marina access, this updated coastal getaway delivers effortless weekend living without Historic District restrictions. Major recent capital investments—a new roof (2024), updated plumbing (2025), upgraded crawlspace with French drain (2025), and Thompson Creek windows—mean zero weekend project lists. Spend your Saturdays lounging by your private in-ground pool, hosting at the beach bar with cable TV, or storing kayaks and gear in the detached garage. Convenient main-level living just steps from downtown dining, coffee shops, and harbor parks. Perfect as a low-maintenance weekend retreat or primary escape from Day 1.

2 Beds ⋅ 1 Baths

Just reduced to $525,000—affordable, turn-key easy living near the water in St. Michaels. Located 1.5 blocks from public boat ramps and marina access, this updated coastal getaway delivers effortless weekend living without Historic District restrictions. Major recent capital investments—a new roof (2024), updated plumbing (2025), upgraded crawlspace with French drain (2025), and Thompson Creek windows—mean zero weekend project lists. Spend your Saturdays lounging by your private in-ground pool, hosting at the beach bar with cable TV, or storing kayaks and gear in the detached garage. Convenient main-level living just steps from downtown dining, coffee shops, and harbor parks. Perfect as a low-maintenance weekend retreat or primary escape from Day 1.

204 E Marengo St, Saint Michaels

Listing courtesy of Compass. Contact:

$725,000

Quality construction throughout. This Custom Coastal Home has all the bells and whistles ..... hardwood cherry floors, masonry fireplace, 1st floor primary suite, double porches to enjoy the sunsets over Eastern Bay. Gourmet kitchen with stainless steel appliances. Two screened in porches for dining or sleeping. Very private with professional landscaping. Easy walk to Claiborne boat ramp, beach and jetty. More pictures to follow..

3 Beds ⋅ 3 Baths

Quality construction throughout. This Custom Coastal Home has all the bells and whistles ..... hardwood cherry floors, masonry fireplace, 1st floor primary suite, double porches to enjoy the sunsets over Eastern Bay. Gourmet kitchen with stainless steel appliances. Two screened in porches for dining or sleeping. Very private with professional landscaping. Easy walk to Claiborne boat ramp, beach and jetty. More pictures to follow..

10554 Miracle House Cir, Claiborne

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

$375,000

Located in the waterfront village of Wittman, close to the public landing and county park, this beautifully crafted two-story cottage blends charm and character with thoughtful design. The home features 2 bedrooms, 1.5 baths, multiple living areas and 2 office spaces . Open beams, wood floors, and architectural details create a warm, inviting atmosphere throughout. Meticulous renovations by a master carpenter include elevating the home, new foundation and accessible crawl space. This unique property offers a perfect blend of craftsmanship and Chesapeake lifestyle. Enjoy the nearby amenities of St. Michaels, Tilghman Island and Easton - restaurants, shops, museums, galleries and more. If you're searching for an escape - this just might be it!

2 Beds ⋅ 2 Baths

Located in the waterfront village of Wittman, close to the public landing and county park, this beautifully crafted two-story cottage blends charm and character with thoughtful design. The home features 2 bedrooms, 1.5 baths, multiple living areas and 2 office spaces . Open beams, wood floors, and architectural details create a warm, inviting atmosphere throughout. Meticulous renovations by a master carpenter include elevating the home, new foundation and accessible crawl space. This unique property offers a perfect blend of craftsmanship and Chesapeake lifestyle. Enjoy the nearby amenities of St. Michaels, Tilghman Island and Easton - restaurants, shops, museums, galleries and more. If you're searching for an escape - this just might be it!

8805 Cummings Rd, Wittman

Listing courtesy of Benson & Mangold, LLC. Contact:

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