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$425,000

Welcome to this beautifully updated cottage in the heart of St. Michaels—where modern comfort meets Eastern Shore charm. Perfectly situated within walking distance to the town’s shops, restaurants, Rails to Trails, and the renowned Maritime Museum, this single‑level home offers both convenience and a peaceful, private setting. Sitting on nearly a quarter acre, the property features a fully fenced backyard with a 6‑ft wood privacy fence, creating an ideal space for outdoor living, pets, or quiet relaxation. Inside, the home presents like new with thoughtful upgrades throughout, including hardwood flooring, recessed lighting & fresh interior paint. The kitchen and bathrooms shine with quartz countertops, tile flooring, and modern finishes. The kitchen is equipped with stainless steel appliances, new cabinetry, quartz countertops, and an under‑sink water filtration system. A front‑loading Samsung washer and dryer and a 50‑gallon water heater add to the home’s move‑in‑ready appeal. Offering 3 bedrooms and 2 full bathrooms, this well‑designed floor plan provides comfortable single‑floor living in one of the Eastern Shore’s most desirable towns. Whether you’re seeking a full‑time residence, a weekend retreat, or an investment opportunity, this St. Michaels gem delivers style, convenience, and exceptional value. The driveway access is on N Talbot St. Please see agent remarks. Try before you buy with a minimum 4-month lease. Please see rental listing! Seller may accept an offer at any time without notice.

3 Beds ⋅ 2 Baths

Welcome to this beautifully updated cottage in the heart of St. Michaels—where modern comfort meets Eastern Shore charm. Perfectly situated within walking distance to the town’s shops, restaurants, Rails to Trails, and the renowned Maritime Museum, this single‑level home offers both convenience and a peaceful, private setting. Sitting on nearly a quarter acre, the property features a fully fenced backyard with a 6‑ft wood privacy fence, creating an ideal space for outdoor living, pets, or quiet relaxation. Inside, the home presents like new with thoughtful upgrades throughout, including hardwood flooring, recessed lighting & fresh interior paint. The kitchen and bathrooms shine with quartz countertops, tile flooring, and modern finishes. The kitchen is equipped with stainless steel appliances, new cabinetry, quartz countertops, and an under‑sink water filtration system. A front‑loading Samsung washer and dryer and a 50‑gallon water heater add to the home’s move‑in‑ready appeal. Offering 3 bedrooms and 2 full bathrooms, this well‑designed floor plan provides comfortable single‑floor living in one of the Eastern Shore’s most desirable towns. Whether you’re seeking a full‑time residence, a weekend retreat, or an investment opportunity, this St. Michaels gem delivers style, convenience, and exceptional value. The driveway access is on N Talbot St. Please see agent remarks. Try before you buy with a minimum 4-month lease. Please see rental listing! Seller may accept an offer at any time without notice.

101 Brooks Ln, Saint Michaels

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

$779,000

A rare opportunity to pair a half-acre+ wooded in-town parcel with a thoughtfully designed single-level home concept in the heart of St. Michaels. This Concept A plan illustrates a 3-bedroom, 2-bath residence totaling approximately 1,710 square feet, featuring one-level living and an attached one-car garage. Designed to maximize functionality and flow, the concept offers flexible living spaces that can be tailored to the buyer’s preferences while preserving privacy and connection to the natural setting. Restaurants, shops, seasonal events, waterfront parks, and the character of the historic district are all close at hand, yet the setting feels quiet and tucked away. Approximately three times the size of a typical in-town lot, the parcel allows generous room for outdoor living and thoughtful home placement, with driveway access possible from Miles Avenue, Canton Street, or both, depending on final design. Infrastructure upgrades are already complete, including paved roads, a State-approved gravel extension, town water, county sewer, electric service, and fiber-optic internet—allowing for a smoother path from planning to construction. With the appropriate Town approvals, the parcel also offers future subdivision potential. Adjacent to the scenic Rails-to-Trails corridor and near San Domingo Creek, the Miles River, and multiple neighborhood parks, the location provides access to nature and open space without giving up the benefits of being in town. Architectural concept drawings illustrating one potential approach to the site will convey to the new owner, with the option to continue working with the original architect if desired. A unique chance to create something truly exceptional in one of the Eastern Shore’s most sought-after communities: space, privacy, and the freedom to design a home that reflects your vision. By Vehicle: A portion of Canton St is a one-way and Miles Ave is not a completely through Street from Railroad Ave. It is recommended to head north on Talbot St., turn left on Railroad Ave., then left on Glory Ave (also known as Gloria), and right on Canton St. Proceed a short way to the corner of the lot at Miles Ave. & Canton St.

3 Beds ⋅ 2 Baths

A rare opportunity to pair a half-acre+ wooded in-town parcel with a thoughtfully designed single-level home concept in the heart of St. Michaels. This Concept A plan illustrates a 3-bedroom, 2-bath residence totaling approximately 1,710 square feet, featuring one-level living and an attached one-car garage. Designed to maximize functionality and flow, the concept offers flexible living spaces that can be tailored to the buyer’s preferences while preserving privacy and connection to the natural setting. Restaurants, shops, seasonal events, waterfront parks, and the character of the historic district are all close at hand, yet the setting feels quiet and tucked away. Approximately three times the size of a typical in-town lot, the parcel allows generous room for outdoor living and thoughtful home placement, with driveway access possible from Miles Avenue, Canton Street, or both, depending on final design. Infrastructure upgrades are already complete, including paved roads, a State-approved gravel extension, town water, county sewer, electric service, and fiber-optic internet—allowing for a smoother path from planning to construction. With the appropriate Town approvals, the parcel also offers future subdivision potential. Adjacent to the scenic Rails-to-Trails corridor and near San Domingo Creek, the Miles River, and multiple neighborhood parks, the location provides access to nature and open space without giving up the benefits of being in town. Architectural concept drawings illustrating one potential approach to the site will convey to the new owner, with the option to continue working with the original architect if desired. A unique chance to create something truly exceptional in one of the Eastern Shore’s most sought-after communities: space, privacy, and the freedom to design a home that reflects your vision. By Vehicle: A portion of Canton St is a one-way and Miles Ave is not a completely through Street from Railroad Ave. It is recommended to head north on Talbot St., turn left on Railroad Ave., then left on Glory Ave (also known as Gloria), and right on Canton St. Proceed a short way to the corner of the lot at Miles Ave. & Canton St.

108 Miles Ave, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$3,100,000

Located within 2 miles of historic St. Michaels this exceptional waterfront estate blends timeless elegance with a resort-style setting. This 4,200± sq. ft. custom, single-level all brick residence showcases soaring ceilings, an abundance of natural light, and panoramic views of Broad Creek from almost every room. A huge great room featuring a large brick fireplace and open living / dining options. There is a gorgeous gourmet kitchen complete with quartz counters, stainless steel appliances and walk in pantry, seamlessly flowing into a spacious family room with a timeless double sided brick fireplace and built-in bookcase. An architecturally stunning screened octagonal porch—perfect for relaxing or entertaining. A brick-floored sunroom with gas fireplace and pool bath leads to an expansive patio overlooking the waterside pool, framed by a rock waterfall, and custom gazebo. The luxurious primary suite features cathedral ceilings, French doors leading to the sunroom and a spa-inspired bath with walk in tile shower and soaking tub. Two additional en-suite bedrooms, a large den with custom built-ins perfect for library or additional bedroom, and a spacious butler’s pantry with granite counters, extra refrigerator, stainless sink and additional cabinetry. A separate study and conditioned workshop offer versatile space. Set on five beautifully landscaped acres with southern exposure, the property boasts 370+/- feet of protected shoreline and a 350-foot private pier with 6 feet of deep water. Boating enthusiasts will appreciate the 15,000-lb and 8,000-lb lifts, two additional slips, and a floating dock. A gated 30' x 40' flower/vegetable garden with raised beds, an oversized 2-car garage and large garden shed complete this beautiful home. Septic is for 3 BR but office could be BR #4.

4 Beds ⋅ 4 Baths

Located within 2 miles of historic St. Michaels this exceptional waterfront estate blends timeless elegance with a resort-style setting. This 4,200± sq. ft. custom, single-level all brick residence showcases soaring ceilings, an abundance of natural light, and panoramic views of Broad Creek from almost every room. A huge great room featuring a large brick fireplace and open living / dining options. There is a gorgeous gourmet kitchen complete with quartz counters, stainless steel appliances and walk in pantry, seamlessly flowing into a spacious family room with a timeless double sided brick fireplace and built-in bookcase. An architecturally stunning screened octagonal porch—perfect for relaxing or entertaining. A brick-floored sunroom with gas fireplace and pool bath leads to an expansive patio overlooking the waterside pool, framed by a rock waterfall, and custom gazebo. The luxurious primary suite features cathedral ceilings, French doors leading to the sunroom and a spa-inspired bath with walk in tile shower and soaking tub. Two additional en-suite bedrooms, a large den with custom built-ins perfect for library or additional bedroom, and a spacious butler’s pantry with granite counters, extra refrigerator, stainless sink and additional cabinetry. A separate study and conditioned workshop offer versatile space. Set on five beautifully landscaped acres with southern exposure, the property boasts 370+/- feet of protected shoreline and a 350-foot private pier with 6 feet of deep water. Boating enthusiasts will appreciate the 15,000-lb and 8,000-lb lifts, two additional slips, and a floating dock. A gated 30' x 40' flower/vegetable garden with raised beds, an oversized 2-car garage and large garden shed complete this beautiful home. Septic is for 3 BR but office could be BR #4.

23961 Lynnewood Dr, Saint Michaels

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

$1,679,000

Significant price improvement! Welcome to your private waterfront retreat just minutes from the charming, historic town of St. Michaels, Maryland. Tucked away on a quiet cul-de-sac in the serene Oakwood Park community along San Domingo Creek, this one-story residence offers four bedrooms, three and a half baths, and a harmonious blend of space and comfort. With approximately 2,839 finished square feet, all on the main level, the home is designed for convenience and ease of living. Inside, generous rooms are enhanced by rich custom yellow pine floors, premium carpeting, and tile. At the heart of the home, the living room impresses with a vaulted ceiling, exposed beams, custom built-ins, and a rustic wood-burning fireplace. A waterfront family room flows into the dining area, while the country kitchen features handsome cabinetry, premium countertops, modern appliances, and a pantry with washer and dryer. The waterside primary suite offers a fireplace, walk-in closet, and a spacious bathroom with dual vanities. On the opposite side of the home, a second bedroom includes an ensuite bath and walk-in closet, complemented by two additional bedrooms with ample closet space (one used as den) and a full bath. The exterior showcases cedar shake siding, a welcoming covered front porch, a private patio between the main bedrooms, a large rear waterside deck, a two-car detached garage, and a wide gravel driveway with ample guest parking. The property is served by a private well and septic system, with public sewer hookup approved and coming soon, offering flexibility for future expansion or renovation. This home is part of a unique five-property HOA (fees $600/year) with each property owning 20% of a central community lot, a deepwater dock with five slips, and a historic pavilion available for member events and leisure. Residents also enjoy a kayak rack and a small sandy beach for launching boats or paddle boards. The setting provides not only a comfortable home but a lifestyle of Chesapeake Bay waterfront living. According to research, the grounds of the five lots and the “Oakwood Association” belonged long ago to the Oakwood Inn, a prominent retreat in the early 20th century. Known for its scenic harbor views and role in local leisure culture, the inn appeared in postcards from the 1930s and was a hub for skating, swimming, pleasure boating, regattas, and log canoe races. Its legacy adds a rich historical dimension to the property, connecting today’s residents to St. Michaels’ vibrant past as a sailing and leisure destination. There are photos of two pieces of memorabilia at the end of the photo section of this listing for your enjoyment. See attached documents for HOA information ($600/year per property), easement information, C&Rs, Contract Disclosures, etc. Flood Zone X, no flood insurance required. Three-bedroom septic, public sewer hookup available near future.

4 Beds ⋅ 4 Baths

Significant price improvement! Welcome to your private waterfront retreat just minutes from the charming, historic town of St. Michaels, Maryland. Tucked away on a quiet cul-de-sac in the serene Oakwood Park community along San Domingo Creek, this one-story residence offers four bedrooms, three and a half baths, and a harmonious blend of space and comfort. With approximately 2,839 finished square feet, all on the main level, the home is designed for convenience and ease of living. Inside, generous rooms are enhanced by rich custom yellow pine floors, premium carpeting, and tile. At the heart of the home, the living room impresses with a vaulted ceiling, exposed beams, custom built-ins, and a rustic wood-burning fireplace. A waterfront family room flows into the dining area, while the country kitchen features handsome cabinetry, premium countertops, modern appliances, and a pantry with washer and dryer. The waterside primary suite offers a fireplace, walk-in closet, and a spacious bathroom with dual vanities. On the opposite side of the home, a second bedroom includes an ensuite bath and walk-in closet, complemented by two additional bedrooms with ample closet space (one used as den) and a full bath. The exterior showcases cedar shake siding, a welcoming covered front porch, a private patio between the main bedrooms, a large rear waterside deck, a two-car detached garage, and a wide gravel driveway with ample guest parking. The property is served by a private well and septic system, with public sewer hookup approved and coming soon, offering flexibility for future expansion or renovation. This home is part of a unique five-property HOA (fees $600/year) with each property owning 20% of a central community lot, a deepwater dock with five slips, and a historic pavilion available for member events and leisure. Residents also enjoy a kayak rack and a small sandy beach for launching boats or paddle boards. The setting provides not only a comfortable home but a lifestyle of Chesapeake Bay waterfront living. According to research, the grounds of the five lots and the “Oakwood Association” belonged long ago to the Oakwood Inn, a prominent retreat in the early 20th century. Known for its scenic harbor views and role in local leisure culture, the inn appeared in postcards from the 1930s and was a hub for skating, swimming, pleasure boating, regattas, and log canoe races. Its legacy adds a rich historical dimension to the property, connecting today’s residents to St. Michaels’ vibrant past as a sailing and leisure destination. There are photos of two pieces of memorabilia at the end of the photo section of this listing for your enjoyment. See attached documents for HOA information ($600/year per property), easement information, C&Rs, Contract Disclosures, etc. Flood Zone X, no flood insurance required. Three-bedroom septic, public sewer hookup available near future.

24390 Oakwood Park Rd, Saint Michaels

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

$489,888

3 Beds ⋅ 2 Baths

5654 Trafalgar Cir, Tilghman

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

$529,888

Built in 2025, this new construction home offers the best of Eastern Shore living in the water-privileged community of Tilghman on the Chesapeake. Enjoy the ease of one-level living and a thoughtfully designed split-bedroom floor plan. The welcoming covered front porch opens to a bright entry foyer leading to the spacious, open-concept living area. The kitchen boasts granite countertops, a center island with bar seating, a pantry and ample cabinet space, perfect for everyday living and entertaining. The kitchen overlooks the living room, featuring a cozy gas fireplace and an open dining area with a sliding glass door, ideal for adding a future deck or patio. The primary suite is privately situated off the main living space and features two walk-in closets and a luxurious bathroom with a granite double-sink vanity, tile and glass shower and a linen closet. Two additional bedrooms and a full guest bath are located on the opposite side of the home, offering privacy for guests or family members. A separate laundry/mudroom provides convenient access to the attached two-car garage. Built by Gemcraft Homes, a highly regarded regional builder, this home provides peace of mind with a 1-year builder warranty, 2-year HVAC/plumbing/electrical coverage and a 5-year structural warranty. For a separate fee, owners can enjoy the amenities of the Tilghman on the Chesapeake waterfront clubhouse, which features a pool and recreation room with an expansive deck and balcony, perfect for hosting events or gatherings. Boat slips are also available, offering easy access to the Bay. Located just moments from local restaurants, multiple boat landings, prime fishing spots and centrally positioned for boating to St. Michaels, Kent Island, Oxford, Cambridge and Annapolis. This isn’t just a home, it’s a lifestyle.

3 Beds ⋅ 2 Baths

Built in 2025, this new construction home offers the best of Eastern Shore living in the water-privileged community of Tilghman on the Chesapeake. Enjoy the ease of one-level living and a thoughtfully designed split-bedroom floor plan. The welcoming covered front porch opens to a bright entry foyer leading to the spacious, open-concept living area. The kitchen boasts granite countertops, a center island with bar seating, a pantry and ample cabinet space, perfect for everyday living and entertaining. The kitchen overlooks the living room, featuring a cozy gas fireplace and an open dining area with a sliding glass door, ideal for adding a future deck or patio. The primary suite is privately situated off the main living space and features two walk-in closets and a luxurious bathroom with a granite double-sink vanity, tile and glass shower and a linen closet. Two additional bedrooms and a full guest bath are located on the opposite side of the home, offering privacy for guests or family members. A separate laundry/mudroom provides convenient access to the attached two-car garage. Built by Gemcraft Homes, a highly regarded regional builder, this home provides peace of mind with a 1-year builder warranty, 2-year HVAC/plumbing/electrical coverage and a 5-year structural warranty. For a separate fee, owners can enjoy the amenities of the Tilghman on the Chesapeake waterfront clubhouse, which features a pool and recreation room with an expansive deck and balcony, perfect for hosting events or gatherings. Boat slips are also available, offering easy access to the Bay. Located just moments from local restaurants, multiple boat landings, prime fishing spots and centrally positioned for boating to St. Michaels, Kent Island, Oxford, Cambridge and Annapolis. This isn’t just a home, it’s a lifestyle.

5648 Trafalgar Cir, Tilghman

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

$2,095,000

**Discover Your Waterfront Oasis in Royal Oak** Nestled in the charming town of Royal Oak, these exceptional waterfront properties present breathtaking views of Oak Creek, conveniently located near the Miles River and the renowned Chesapeake Bay. Positioned between the picturesque communities of Saint Michael’s and Easton, this rare gem boasts approximately 541 feet of pristine water frontage, enhanced by a newly installed bulkhead as of summer 2025. Comprising two distinct parcels, both properties offer expansive water vistas that are truly captivating. Imagine enjoying serene afternoons by one of the two existing pools, each perfectly situated to overlook the tranquil waters. Each home is equipped with its own dedicated well and is connected to public sewer, ensuring convenience and reliability. Elevated above flood risks, this property requires no flood insurance, providing peace of mind for future owners. The first residence, a charming brick rancher at 7049 Acorn Alley, features single-story living with three bedrooms and 1.5 baths, set on a generous .81 acres. Built in 1963, it offers 1,454 square feet of cozy, inviting space. Across the way, the colonial-style home at 7047 Acorn Alley boasts four bedrooms and two full baths, nestled on .73 acres. Constructed in 1975, this expansive 1,920-square-foot residence provides ample room for family gatherings and entertaining. Ideal for outdoor enthusiasts, this location is a paradise for boating, fishing, kayaking, and paddle boarding, with calm waterways that invite exploration. The property is also perfect for bird watching and cycling, making it an ideal haven for nature lovers. Whether you envision a lucrative investment, a serene vacation retreat, or the canvas for your dream home, the endless possibilities await. Centrally located in Talbot County, with easy access to Easton, Baltimore, and the DC metro area, as well as a short ferry ride to Oxford, this property is a unique opportunity not to be missed. Embrace the lifestyle you've always desired and make this waterfront paradise your own.

6 Beds ⋅ 4 Baths

**Discover Your Waterfront Oasis in Royal Oak** Nestled in the charming town of Royal Oak, these exceptional waterfront properties present breathtaking views of Oak Creek, conveniently located near the Miles River and the renowned Chesapeake Bay. Positioned between the picturesque communities of Saint Michael’s and Easton, this rare gem boasts approximately 541 feet of pristine water frontage, enhanced by a newly installed bulkhead as of summer 2025. Comprising two distinct parcels, both properties offer expansive water vistas that are truly captivating. Imagine enjoying serene afternoons by one of the two existing pools, each perfectly situated to overlook the tranquil waters. Each home is equipped with its own dedicated well and is connected to public sewer, ensuring convenience and reliability. Elevated above flood risks, this property requires no flood insurance, providing peace of mind for future owners. The first residence, a charming brick rancher at 7049 Acorn Alley, features single-story living with three bedrooms and 1.5 baths, set on a generous .81 acres. Built in 1963, it offers 1,454 square feet of cozy, inviting space. Across the way, the colonial-style home at 7047 Acorn Alley boasts four bedrooms and two full baths, nestled on .73 acres. Constructed in 1975, this expansive 1,920-square-foot residence provides ample room for family gatherings and entertaining. Ideal for outdoor enthusiasts, this location is a paradise for boating, fishing, kayaking, and paddle boarding, with calm waterways that invite exploration. The property is also perfect for bird watching and cycling, making it an ideal haven for nature lovers. Whether you envision a lucrative investment, a serene vacation retreat, or the canvas for your dream home, the endless possibilities await. Centrally located in Talbot County, with easy access to Easton, Baltimore, and the DC metro area, as well as a short ferry ride to Oxford, this property is a unique opportunity not to be missed. Embrace the lifestyle you've always desired and make this waterfront paradise your own.

7049 & 7047 Acorn Aly, Royal Oak

Listing courtesy of McClain-Williamson Realty, LLC. Contact: