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SECOND WIND is a remarkable Eastern Shore sanctuary where history, privacy, and the beauty of the water define everyday living. As noted in The Eastern Shore Dependent in 1963, “Nature provided the idyllic setting.” Set amid nearly 3 acres of magnificent landscaping, with more than 400 feet of protected and licensed shoreline, this property captures sweeping broad water views and unforgettable sunsets from almost every room. The historic c. 1800 two-story section enjoys random width Georgia pine floors. On the main level you will find a fireside den with built-in bookcases plus a private office with fireplace and two bedrooms and a full bath upstairs. The more contemporary additions include multiple living areas offering a welcoming blend of historic character and comfortable living, including living/dining room, an inviting county kitchen and a main-level primary suite with vaulted beamed ceiling and en-suite bath. The kitchen features a breakfast bar and casual dining area, opening to a patio and heated pool and spa – an inviting setting for relaxation and entertaining. A private pier and protected and licensed shoreline incorporating a living shoreline enhance the waterfront setting, while magnificent perennial gardens, an attached garage, a detached workshop with artist studio above, and several outbuildings add to the property's appeal. Recent improvements include a new roof. Lovingly maintained and exceptionally private, SECOND WIND offers a rare opportunity to own a truly distinctive waterfront property steeped in Eastern Shore history.

3 Beds ⋅ 3 Baths

SECOND WIND is a remarkable Eastern Shore sanctuary where history, privacy, and the beauty of the water define everyday living. As noted in The Eastern Shore Dependent in 1963, “Nature provided the idyllic setting.” Set amid nearly 3 acres of magnificent landscaping, with more than 400 feet of protected and licensed shoreline, this property captures sweeping broad water views and unforgettable sunsets from almost every room. The historic c. 1800 two-story section enjoys random width Georgia pine floors. On the main level you will find a fireside den with built-in bookcases plus a private office with fireplace and two bedrooms and a full bath upstairs. The more contemporary additions include multiple living areas offering a welcoming blend of historic character and comfortable living, including living/dining room, an inviting county kitchen and a main-level primary suite with vaulted beamed ceiling and en-suite bath. The kitchen features a breakfast bar and casual dining area, opening to a patio and heated pool and spa – an inviting setting for relaxation and entertaining. A private pier and protected and licensed shoreline incorporating a living shoreline enhance the waterfront setting, while magnificent perennial gardens, an attached garage, a detached workshop with artist studio above, and several outbuildings add to the property's appeal. Recent improvements include a new roof. Lovingly maintained and exceptionally private, SECOND WIND offers a rare opportunity to own a truly distinctive waterfront property steeped in Eastern Shore history.

5704 Irish Creek Rd, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

$939,900

Boat-ready waterfront on Tar Creek, with minutes-by-water access to the Tred Avon! Welcome to a turn-key Eastern Shore weekend retreat, quietly tucked at the end of a private lane in the historic village of Bellevue, ideally positioned between St. Michaels and Oxford. This custom 2013 Cape Cod-style home sits gracefully on a tree-framed third of an acre, offering 55 feet of prime shoreline protected by an engineered bulkhead. Designed for water enthusiasts, a private 60-foot pier extends into the creek, complete with an electric lift for jet skis or small tenders, plus dockside power and water. Inside, light-filled living spaces flow across espresso-toned plank floors. Soaring cathedral ceilings, gable windows, and skylights crown the great room, where a stacked-stone gas fireplace anchors the open floor plan. The kitchen features a six-burner gas range, maple Shaker cabinetry, and a center island, adjoining a dining area that easily seats eight or more. Two sets of sliding glass doors open to the backyard deck, leading out to a stone patio, firepit, and outdoor shower. The main level includes two comfortable bedrooms, a full bath, and a laundry room. Upstairs, a skylit loft framed by cherry wood and stainless cable rails overlooks the great room. The vaulted primary suite offers dual closets, barn doors, and an en-suite bath complete with a walk-in tile shower and soapstone trough vanity. Built for low-maintenance, lock-and-leave ownership, the home features a tankless water heater, fire sprinklers, heat pump with central A/C, phone-managed Nest controls, county sewer, and a clean cement crawlspace equipped with a sump pump. Located steps from the Oxford-Bellevue Ferry. About two hours from Washington, D.C., Northern Virginia, Montgomery County, and Wilmington, with Route 301 through Delaware allowing you to bypass Bay Bridge traffic. Leave Friday, be on the water by sunset. Bring your boat!

3 Beds ⋅ 2 Baths

Boat-ready waterfront on Tar Creek, with minutes-by-water access to the Tred Avon! Welcome to a turn-key Eastern Shore weekend retreat, quietly tucked at the end of a private lane in the historic village of Bellevue, ideally positioned between St. Michaels and Oxford. This custom 2013 Cape Cod-style home sits gracefully on a tree-framed third of an acre, offering 55 feet of prime shoreline protected by an engineered bulkhead. Designed for water enthusiasts, a private 60-foot pier extends into the creek, complete with an electric lift for jet skis or small tenders, plus dockside power and water. Inside, light-filled living spaces flow across espresso-toned plank floors. Soaring cathedral ceilings, gable windows, and skylights crown the great room, where a stacked-stone gas fireplace anchors the open floor plan. The kitchen features a six-burner gas range, maple Shaker cabinetry, and a center island, adjoining a dining area that easily seats eight or more. Two sets of sliding glass doors open to the backyard deck, leading out to a stone patio, firepit, and outdoor shower. The main level includes two comfortable bedrooms, a full bath, and a laundry room. Upstairs, a skylit loft framed by cherry wood and stainless cable rails overlooks the great room. The vaulted primary suite offers dual closets, barn doors, and an en-suite bath complete with a walk-in tile shower and soapstone trough vanity. Built for low-maintenance, lock-and-leave ownership, the home features a tankless water heater, fire sprinklers, heat pump with central A/C, phone-managed Nest controls, county sewer, and a clean cement crawlspace equipped with a sump pump. Located steps from the Oxford-Bellevue Ferry. About two hours from Washington, D.C., Northern Virginia, Montgomery County, and Wilmington, with Route 301 through Delaware allowing you to bypass Bay Bridge traffic. Leave Friday, be on the water by sunset. Bring your boat!

5734 Poplar Ln, Royal Oak

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

$425,000

Handsome, cozy Farmhouse in the village of Royal Oak. Built in 1999 with a modern floor plan and amenities providing three bedrooms and two and a half baths. Great covered front porch and side patio with privacy screening. Second floor sun deck and primary suite with walk-in closet and attached full bath. New LVP flooring upstairs and wood flooring downstairs. Sited on a generous .69 acre lot with mature tree canopy, nice lawn expanse and a sturdy shed. Well water and County sewer service. OWNER FINANCING AVAILABLE FOR QUALIFIED BUYERS

3 Beds ⋅ 3 Baths

Handsome, cozy Farmhouse in the village of Royal Oak. Built in 1999 with a modern floor plan and amenities providing three bedrooms and two and a half baths. Great covered front porch and side patio with privacy screening. Second floor sun deck and primary suite with walk-in closet and attached full bath. New LVP flooring upstairs and wood flooring downstairs. Sited on a generous .69 acre lot with mature tree canopy, nice lawn expanse and a sturdy shed. Well water and County sewer service. OWNER FINANCING AVAILABLE FOR QUALIFIED BUYERS

6935 Bellevue Rd, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

$2,375,000

Solitude on Edge Creek with over 300+/- feet of tranquil waterfrontage and protected shoreline. Five-foot-wide pier with ample room for boats, substantial boat lift and 2-3+/- feet mean low water. A private, serene Eastern Shore retreat on manageable 3+/- acres with its very own nature walking-trail. The park-like setting features southeast exposure, a multitude of beautiful, specimen trees, and waterside pool with shaded patio. The additional charming and practical one bedroom guest house with separate kitchen offers a sanctuary for any weekend visitors. The main house includes first and second floor primary suites with views of the creek and all its natural inhabitants, an additional 3 bedrooms (one with en-suite bath), a total of 4 1/2 bathrooms, a terrific light-filled, large sunroom and waterside deck. Conveniently located close to the wonderful dining at The Oaks Waterfront Hotel and t at The General Store, while also not far from the Bellevue Ferry to historic Oxford, MD or shops of St. Michaels.

5 Beds ⋅ 5 Baths

Solitude on Edge Creek with over 300+/- feet of tranquil waterfrontage and protected shoreline. Five-foot-wide pier with ample room for boats, substantial boat lift and 2-3+/- feet mean low water. A private, serene Eastern Shore retreat on manageable 3+/- acres with its very own nature walking-trail. The park-like setting features southeast exposure, a multitude of beautiful, specimen trees, and waterside pool with shaded patio. The additional charming and practical one bedroom guest house with separate kitchen offers a sanctuary for any weekend visitors. The main house includes first and second floor primary suites with views of the creek and all its natural inhabitants, an additional 3 bedrooms (one with en-suite bath), a total of 4 1/2 bathrooms, a terrific light-filled, large sunroom and waterside deck. Conveniently located close to the wonderful dining at The Oaks Waterfront Hotel and t at The General Store, while also not far from the Bellevue Ferry to historic Oxford, MD or shops of St. Michaels.

25705 Edgeview Rd, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

$695,000

3 Beds ⋅ 3 Baths

25857 Royal Oak Rd, Royal Oak

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

$179,000

1.5 +/- acres perc approved building lot located in Royal Oak Md. Located minutes from St. Michaels and Easton Md and only a short drive to the Oxford / Bellevue Ferry. A perfect opportunity to build your eastern shore dream home in a rural setting while enjoying 5-star dining and amenities only a short drive away. Building lots of this caliber are rare in the county and do not come available often. AI image of potential home provided for buyer's vision.

Deep Neck Rd, Royal Oak

Listing courtesy of Meredith Fine Properties. Contact:

$599,000

This beautifully maintained 3-bedroom, 3-bathroom home is special the second you pull into the driveway. Situated on nearly an acre in a private and peaceful setting. When you enter the front door, you will be drawn to the large screen porch ion the rear of the home and you are also greeted by a generous living room with two fireplaces. The kitchen is large and functional with plenty of space for a large table with an office/den directly off the kitchen. Upstairs you will find 3 ensuite bedrooms with a stunning primary with a beautiful walk in shower. The outside space is stunning with a large screen porch and separate patio to enjoy the very private and parklike back yard. Other features include a conditioned crawlspace, tankless hot water heater and high speed internet provided by Easton Utilities. The ferry to Oxford, and public boat ramp are right down the road and this area is renowned for its biking and beauty. Being 10 minutes from Easton and Saint Michaels this is the ideal setting to enjoy the peaceful Eastern Shore with easy proximity to all intown amenities.

3 Beds ⋅ 3 Baths

This beautifully maintained 3-bedroom, 3-bathroom home is special the second you pull into the driveway. Situated on nearly an acre in a private and peaceful setting. When you enter the front door, you will be drawn to the large screen porch ion the rear of the home and you are also greeted by a generous living room with two fireplaces. The kitchen is large and functional with plenty of space for a large table with an office/den directly off the kitchen. Upstairs you will find 3 ensuite bedrooms with a stunning primary with a beautiful walk in shower. The outside space is stunning with a large screen porch and separate patio to enjoy the very private and parklike back yard. Other features include a conditioned crawlspace, tankless hot water heater and high speed internet provided by Easton Utilities. The ferry to Oxford, and public boat ramp are right down the road and this area is renowned for its biking and beauty. Being 10 minutes from Easton and Saint Michaels this is the ideal setting to enjoy the peaceful Eastern Shore with easy proximity to all intown amenities.

6280 Bellevue Rd, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

$4,000,000

A masterpiece of Eastern Shore living, this Tidewater colonial estate is set against sweeping, panoramic views where the Choptank River, Chesapeake Bay, and three creeks converge. Showcasing breathtaking sunsets, the private oasis features a waterside pool, a main floor primary suite built in 2023, rich hardwood floors, and a detached 3-car garage. Tucked away in the desirable Ferry Neck enclave of Royal Oak, this estate offers the ultimate waterfront lifestyle. As you approach via tree-lined W. Ferry Neck Road, you enter "Tranquility" and are greeted by a circular driveway, mature landscaping, and a profound sense of privacy. Designed for classic Eastern Shore comfort, " Tranquility" offers impressive water perspectives from every room. The Main Level features gleaming hardwood floors, formal living room and dining room, gourmet kitchen with walk-in pantry, screened porch, sunroom, two wood-burning fireplaces, and two convenient powder rooms. The spectacular first-floor primary suite offers an exceptional private sanctuary. The Second Level boasts three well-appointed, ensuite bedrooms, ensuring privacy and comfort for family and guests. Structural Updates: The home also features a brand-new roof installed in 2023. Beyond the main residence, the 3-car detached garage ideal for car enthusiasts has an upper level that presently serves as an office and a substantial storage room. "Tranquility" truly provides the best of both worlds. For just under three acres, the property's privacy is unmatched. The endless water views , the close proximity to the sandy bottom shore, the pier with water, electric, and boat lift, all contribute to the perfect retreat. Furthermore, the convenience to Oxford by boat or the Bellevue Ferry, as well as a 15-minute car ride to both Easton and St. Michaels, define the perfect Talbot County location.

4 Beds ⋅ 6 Baths

A masterpiece of Eastern Shore living, this Tidewater colonial estate is set against sweeping, panoramic views where the Choptank River, Chesapeake Bay, and three creeks converge. Showcasing breathtaking sunsets, the private oasis features a waterside pool, a main floor primary suite built in 2023, rich hardwood floors, and a detached 3-car garage. Tucked away in the desirable Ferry Neck enclave of Royal Oak, this estate offers the ultimate waterfront lifestyle. As you approach via tree-lined W. Ferry Neck Road, you enter "Tranquility" and are greeted by a circular driveway, mature landscaping, and a profound sense of privacy. Designed for classic Eastern Shore comfort, " Tranquility" offers impressive water perspectives from every room. The Main Level features gleaming hardwood floors, formal living room and dining room, gourmet kitchen with walk-in pantry, screened porch, sunroom, two wood-burning fireplaces, and two convenient powder rooms. The spectacular first-floor primary suite offers an exceptional private sanctuary. The Second Level boasts three well-appointed, ensuite bedrooms, ensuring privacy and comfort for family and guests. Structural Updates: The home also features a brand-new roof installed in 2023. Beyond the main residence, the 3-car detached garage ideal for car enthusiasts has an upper level that presently serves as an office and a substantial storage room. "Tranquility" truly provides the best of both worlds. For just under three acres, the property's privacy is unmatched. The endless water views , the close proximity to the sandy bottom shore, the pier with water, electric, and boat lift, all contribute to the perfect retreat. Furthermore, the convenience to Oxford by boat or the Bellevue Ferry, as well as a 15-minute car ride to both Easton and St. Michaels, define the perfect Talbot County location.

24879 W Ferry Neck Rd, Royal Oak

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

$5,850,000

Introducing White Swan Point, an exceptional Chesapeake waterfront estate offering one of the Eastern Shore's most commanding settings. Positioned at the confluence of Broad Creek and the Choptank River, the property enjoys nearly 5,000 feet of shoreline with sweeping western and southwestern vistas that capture spectacular sunsets, cooling summer breezes, and an ever-changing panorama of sailboats, yachts, and waterfowl. With close proximity to major metropolitan areas, this private waterfront retreat offers a rare combination of architectural quality, recreational opportunity, and lasting investment. Whether envisioned as a family compound, executive retreat, or waterfront residence for entertaining on a grand scale, the setting delivers an experience that is increasingly difficult to replicate along the Chesapeake Bay. Constructed in 2006 by its builder as their personal residence, the approximately 8,500 square foot home reflects enduring craftsmanship and design throughout. Seven ensuite bedrooms provide generous accommodations for family and guests, while soaring ceilings, three fireplaces, richly appointed living spaces, and a sunlit morning room create an atmosphere that is both elegant and welcoming. A distinctive turret crowns the residence, providing a remarkable vantage point from which to enjoy the sunset as it settles across Broad Creek. Outdoor living is at the heart of the estate. Expansive terraces, waterside porches, and beautifully landscaped gathering spaces transition naturally toward the shoreline, where the pool, pool house, outdoor kitchen, and riverfront fire pit become the backdrop for unforgettable evenings overlooking the water. Nearly every outdoor amenity has been carefully positioned to take advantage of the property's extraordinary western exposure and uninterrupted water views. For the boating enthusiast, the estate offers exceptional privacy and water access along Broad Creek, providing an ideal setting for cruising to St. Michaels, Oxford, Tilghman Island, and destinations throughout the Chesapeake Bay. Approximately 1,900+/- feet of stone revetment protects the prominent shoreline, while an additional 2,500+/- feet along the quiet waters of Bridge Creek remains preserved in its natural state, creating a diverse waterfront environment rich with wildlife and native vegetation. Beyond the residence, the property continues to offer remarkable flexibility. Approximately 13 acres are under cultivation with an additional 3.5 acres in pasture, presenting opportunities for equestrian pursuits, hobby farming, or simply preserving the estate's open landscape. A substantial 40-foot by 60-foot barn includes workshop space, equipment storage, and a second-floor caretaker or guest apartment, providing exceptional utility for managing the property or accommodating extended stays. White Swan Point represents far more than an extraordinary waterfront home. It is an opportunity to own one of Maryland's signature Chesapeake estates, where privacy, recreation, architectural quality, and timeless waterfront living come together in one exceptional offering.

7 Beds ⋅ 6 Baths

Introducing White Swan Point, an exceptional Chesapeake waterfront estate offering one of the Eastern Shore's most commanding settings. Positioned at the confluence of Broad Creek and the Choptank River, the property enjoys nearly 5,000 feet of shoreline with sweeping western and southwestern vistas that capture spectacular sunsets, cooling summer breezes, and an ever-changing panorama of sailboats, yachts, and waterfowl. With close proximity to major metropolitan areas, this private waterfront retreat offers a rare combination of architectural quality, recreational opportunity, and lasting investment. Whether envisioned as a family compound, executive retreat, or waterfront residence for entertaining on a grand scale, the setting delivers an experience that is increasingly difficult to replicate along the Chesapeake Bay. Constructed in 2006 by its builder as their personal residence, the approximately 8,500 square foot home reflects enduring craftsmanship and design throughout. Seven ensuite bedrooms provide generous accommodations for family and guests, while soaring ceilings, three fireplaces, richly appointed living spaces, and a sunlit morning room create an atmosphere that is both elegant and welcoming. A distinctive turret crowns the residence, providing a remarkable vantage point from which to enjoy the sunset as it settles across Broad Creek. Outdoor living is at the heart of the estate. Expansive terraces, waterside porches, and beautifully landscaped gathering spaces transition naturally toward the shoreline, where the pool, pool house, outdoor kitchen, and riverfront fire pit become the backdrop for unforgettable evenings overlooking the water. Nearly every outdoor amenity has been carefully positioned to take advantage of the property's extraordinary western exposure and uninterrupted water views. For the boating enthusiast, the estate offers exceptional privacy and water access along Broad Creek, providing an ideal setting for cruising to St. Michaels, Oxford, Tilghman Island, and destinations throughout the Chesapeake Bay. Approximately 1,900+/- feet of stone revetment protects the prominent shoreline, while an additional 2,500+/- feet along the quiet waters of Bridge Creek remains preserved in its natural state, creating a diverse waterfront environment rich with wildlife and native vegetation. Beyond the residence, the property continues to offer remarkable flexibility. Approximately 13 acres are under cultivation with an additional 3.5 acres in pasture, presenting opportunities for equestrian pursuits, hobby farming, or simply preserving the estate's open landscape. A substantial 40-foot by 60-foot barn includes workshop space, equipment storage, and a second-floor caretaker or guest apartment, providing exceptional utility for managing the property or accommodating extended stays. White Swan Point represents far more than an extraordinary waterfront home. It is an opportunity to own one of Maryland's signature Chesapeake estates, where privacy, recreation, architectural quality, and timeless waterfront living come together in one exceptional offering.

24390 Deep Neck Farm Ln, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

$725,000

Discover a prime investment opportunity with this 1.991-acre parcel of land featuring direct access to the picturesque Plaindealing Creek. This waterfront property offers significant potential with a perc test approved for a 4-bedroom dwelling. With navigable water access, this land is ideal for activities such as boating, swimming, and kayaking, or for creating a serene retreat, enhancing its appeal to future residents. The combination of land size and water features positions this property as a wonderful opportunity to make your own. Don't miss the chance to secure a valuable asset in a sought-after area.

n/s N/S Gosling Ln, Royal Oak

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

$6,495,000

Irish Creek Waterfront Estate Set along more than 1,000 +/- feet of pristine, navigable waterfront on Irish Creek, this remarkable 22.14 +/- acre waterfront estate captures the very essence of luxury living on Maryland’s Eastern Shore. Surrounded by sweeping southwest-facing water views and unspoiled natural beauty, the property offers exceptional privacy and scale just minutes from the charming towns of Easton and St. Michaels. Approached by a long, private paved drive, the stately Colonial residence blends timeless architecture with comfortable sophistication, designed for both elegant entertaining and relaxed waterfront living. Inside, refined interiors feature rich hardwood flooring, extensive crown molding, custom built-ins, and four wood-burning fireplaces, creating warm gathering spaces throughout the home. The main level is thoughtfully designed for hosting and everyday living, with gracious formal and informal spaces that flow effortlessly together. A formal dining room, expansive living and family rooms, and a well-appointed kitchen with island and pantry create the perfect setting for gatherings with family and friends. The main-level primary suite offers a peaceful retreat with its own fireplace, walk-in closet, and spa-inspired bath. Upstairs, three additional bedrooms and two full baths comfortably accommodate guests for extended weekends on the Shore. Outdoors, the estate unfolds as a private waterfront retreat designed for unforgettable weekends and celebrations. Spend warm summer days by the Gunite pool and outdoor spa, gather around the built-in fire pit at sunset, or enjoy a friendly match on the bocce court. A tranquil pond and expansive grounds enhance the sense of serenity, while the vaulted three-season porch provides the perfect vantage point for watching boats drift by and taking in the breathtaking evening sunsets over Irish Creek. The property is exceptionally well-suited for hosting, with a charming pool house and a separate two-bedroom guest apartment above the detached four-car side-entry garage—ideal for visiting family, weekend guests, or extended stays. Located in the coveted Royal Oak waterfront community, and within easy reach of Easton, St. Michaels, and the Chesapeake Bay, this extraordinary offering is less than two hours from Washington, D.C., Baltimore, and Philadelphia, making it the perfect luxury retreat for weekend escapes or year-round living on the Eastern Shore. Here, life slows down—boating at sunset, long summer weekends with family and friends, and the timeless beauty of Chesapeake Bay living.

4 Beds ⋅ 5 Baths

Irish Creek Waterfront Estate Set along more than 1,000 +/- feet of pristine, navigable waterfront on Irish Creek, this remarkable 22.14 +/- acre waterfront estate captures the very essence of luxury living on Maryland’s Eastern Shore. Surrounded by sweeping southwest-facing water views and unspoiled natural beauty, the property offers exceptional privacy and scale just minutes from the charming towns of Easton and St. Michaels. Approached by a long, private paved drive, the stately Colonial residence blends timeless architecture with comfortable sophistication, designed for both elegant entertaining and relaxed waterfront living. Inside, refined interiors feature rich hardwood flooring, extensive crown molding, custom built-ins, and four wood-burning fireplaces, creating warm gathering spaces throughout the home. The main level is thoughtfully designed for hosting and everyday living, with gracious formal and informal spaces that flow effortlessly together. A formal dining room, expansive living and family rooms, and a well-appointed kitchen with island and pantry create the perfect setting for gatherings with family and friends. The main-level primary suite offers a peaceful retreat with its own fireplace, walk-in closet, and spa-inspired bath. Upstairs, three additional bedrooms and two full baths comfortably accommodate guests for extended weekends on the Shore. Outdoors, the estate unfolds as a private waterfront retreat designed for unforgettable weekends and celebrations. Spend warm summer days by the Gunite pool and outdoor spa, gather around the built-in fire pit at sunset, or enjoy a friendly match on the bocce court. A tranquil pond and expansive grounds enhance the sense of serenity, while the vaulted three-season porch provides the perfect vantage point for watching boats drift by and taking in the breathtaking evening sunsets over Irish Creek. The property is exceptionally well-suited for hosting, with a charming pool house and a separate two-bedroom guest apartment above the detached four-car side-entry garage—ideal for visiting family, weekend guests, or extended stays. Located in the coveted Royal Oak waterfront community, and within easy reach of Easton, St. Michaels, and the Chesapeake Bay, this extraordinary offering is less than two hours from Washington, D.C., Baltimore, and Philadelphia, making it the perfect luxury retreat for weekend escapes or year-round living on the Eastern Shore. Here, life slows down—boating at sunset, long summer weekends with family and friends, and the timeless beauty of Chesapeake Bay living.

24679 Deep Neck Rd, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

$147,200

Buildable 1/2 +/- acre lot ready for your vision and a builder ready to help you make it a reality! Over 500 ft of shoreline on the Tred Avon River. Close to the public park/playground and just a short boat ride or ferry ride to Oxford. Centrally located between Easton and St Michaels. Just minutes to Talbot County's favorite waterfront towns by car, bike, or boat.

25832 Turner Ave, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

$126,400

Buildable 1/2 +/- acre lot ready for your vision and a builder ready to help you make it a reality! Over 500 ft of shoreline on the Tred Avon River. Close to the public park/playground and just a short boat ride or ferry ride to Oxford. Centrally located between Easton and St Michaels. Just minutes to Talbot County's favorite waterfront towns by car, bike, or boat.

25833 Turner Ave, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

$100,800

Buildable 1/2 +/- acre lot ready for your vision and a builder ready to help you make it a reality! Over 500 ft of shoreline on the Tred Avon River. Close to the public park/playground and just a short boat ride or ferry ride to Oxford. Centrally located between Easton and St Michaels. Just minutes to Talbot County's favorite waterfront towns by car, bike, or boat.

25831 Turner Ave, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

$6,890,000

An Exceptional Eastern Shore Estate - 145 Acres of Waterfront, Farmland & Timeless Beauty. There are properties that offer a beautiful setting and then there are properties that possess an unmistakable sense of place. This extraordinary 145 acre estate in coveted Royal Oak is one of the latter - a private waterfront sanctuary where expansive farmland and pasture, mature trees, tranquil ponds and sweeping waterviews converge to create a setting of rare distinction. From the gated drive, the experience is extraordinary. A gracefully paved approach winds through a pastoral landscape of open vistas, three ponds, white-fenced fields and paddocks, and a magnificent canopy of mature sawtooth oaks. Beyond the landscape, the elegant Colonial-style main residence reveals itself, perfectly positioned to capture the serenity of Fox Hole Creek and its long view toward the Tred Avon River. The architecture is gracious and beautifully proportioned. The two-and-a-half-story central section is framed by side wings that step down elegantly to one-story elevations, creating a classic country estate character. Inside, generous proportions, heart pine floors, and natural light complement the home's timeless design. A compelling feature of the residence is its relationship to the water. On the main level, the sunroom, breakfast room, living room, family room, and primary suite all enjoy direct visual connections to the waterfront and open to a sweeping brick terrace extending the length of the house. It is an extraordinary setting for entertaining or simply enjoying the seasons of the Eastern Shore. The second-floor stair hall opens onto a substantial private deck, creating an elevated vantage point overlooking the water and surrounding acreage. Two-bedroom suites and two offices occupy this level, while an additional bedroom suite on the third floor provides comfortable accommodations for guests. The grounds unfold as a collection of distinct destinations. A two-bedroom guest house offers privacy for visitors while the detached garage with apartment above provides versatile space. The resort-style pool is complemented by an elegant pool house featuring a sauna, bath, kitchenette, porch, and lounging areas. A private pier and small boathouse extend the experience to the water, while a greenhouse with its own sitting area offers a tranquil retreat for gardening or quiet reflection. The estate includes a handsome five-stall barn with tack room, washroom, and fenced paddocks. A second barn has been transformed into an impressive garage accommodating classic automobiles—an exceptional amenity that could serve a collector or those seeking extraordinary workspace. Outdoor living is woven throughout the property. The front porch welcomes guests; the expansive covered brick terrace provides an exceptional setting for waterfront entertaining; and a covered brick walkway connects the main residence to the pool and pool house. At the pool, a pergola-shaded lounging area creates an intimate outdoor room designed for long afternoons and summer evenings. The estate is impeccably maintained and equipped for modern living, including a new composite roof, geothermal HVAC, wine cellar, sprinkler system, and high-speed connectivity. Starlink internet is in place, broadband cable is available, and Easton Velocity service is available for hookup. A gated main entrance and separate farm entrance provide convenience and privacy. The Bellevue Ferry to Oxford is nearby, while Easton and St. Michaels are approximately equidistant. Annapolis is approximately 50 miles, Washington, D.C. approximately 70 miles, and Easton Airport: 12 miles. This is a complete Eastern Shore lifestyle—private, elegant, equestrian, agricultural, and intimately connected to the water. SUBDIVISION POTENTIAL presents an additional opportunity, further enhancing the possibilities of this rare offering.

4 Beds ⋅ 5 Baths

An Exceptional Eastern Shore Estate - 145 Acres of Waterfront, Farmland & Timeless Beauty. There are properties that offer a beautiful setting and then there are properties that possess an unmistakable sense of place. This extraordinary 145 acre estate in coveted Royal Oak is one of the latter - a private waterfront sanctuary where expansive farmland and pasture, mature trees, tranquil ponds and sweeping waterviews converge to create a setting of rare distinction. From the gated drive, the experience is extraordinary. A gracefully paved approach winds through a pastoral landscape of open vistas, three ponds, white-fenced fields and paddocks, and a magnificent canopy of mature sawtooth oaks. Beyond the landscape, the elegant Colonial-style main residence reveals itself, perfectly positioned to capture the serenity of Fox Hole Creek and its long view toward the Tred Avon River. The architecture is gracious and beautifully proportioned. The two-and-a-half-story central section is framed by side wings that step down elegantly to one-story elevations, creating a classic country estate character. Inside, generous proportions, heart pine floors, and natural light complement the home's timeless design. A compelling feature of the residence is its relationship to the water. On the main level, the sunroom, breakfast room, living room, family room, and primary suite all enjoy direct visual connections to the waterfront and open to a sweeping brick terrace extending the length of the house. It is an extraordinary setting for entertaining or simply enjoying the seasons of the Eastern Shore. The second-floor stair hall opens onto a substantial private deck, creating an elevated vantage point overlooking the water and surrounding acreage. Two-bedroom suites and two offices occupy this level, while an additional bedroom suite on the third floor provides comfortable accommodations for guests. The grounds unfold as a collection of distinct destinations. A two-bedroom guest house offers privacy for visitors while the detached garage with apartment above provides versatile space. The resort-style pool is complemented by an elegant pool house featuring a sauna, bath, kitchenette, porch, and lounging areas. A private pier and small boathouse extend the experience to the water, while a greenhouse with its own sitting area offers a tranquil retreat for gardening or quiet reflection. The estate includes a handsome five-stall barn with tack room, washroom, and fenced paddocks. A second barn has been transformed into an impressive garage accommodating classic automobiles—an exceptional amenity that could serve a collector or those seeking extraordinary workspace. Outdoor living is woven throughout the property. The front porch welcomes guests; the expansive covered brick terrace provides an exceptional setting for waterfront entertaining; and a covered brick walkway connects the main residence to the pool and pool house. At the pool, a pergola-shaded lounging area creates an intimate outdoor room designed for long afternoons and summer evenings. The estate is impeccably maintained and equipped for modern living, including a new composite roof, geothermal HVAC, wine cellar, sprinkler system, and high-speed connectivity. Starlink internet is in place, broadband cable is available, and Easton Velocity service is available for hookup. A gated main entrance and separate farm entrance provide convenience and privacy. The Bellevue Ferry to Oxford is nearby, while Easton and St. Michaels are approximately equidistant. Annapolis is approximately 50 miles, Washington, D.C. approximately 70 miles, and Easton Airport: 12 miles. This is a complete Eastern Shore lifestyle—private, elegant, equestrian, agricultural, and intimately connected to the water. SUBDIVISION POTENTIAL presents an additional opportunity, further enhancing the possibilities of this rare offering.

5289 Ferry Neck Rd, Royal Oak

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

$799,900

Designed to optimize water views of the Tred Avon and access to the community kayak launch and beach area is this to be built home. Centrally located between Easton and St Michaels and just a stone's throw from the Oxford Bellevue Ferry on the Tred Avon, one of Talbot County's premier waterfront communities with 13 half acre to 1.5 acre home sites. The community features its own private beach and kayak launch with nearby public park with playground and marina. Additional floor plans, options, and upgrades available. Some photos and renderings are for illustrative purposes only and may include additional upgrades.

3 Beds ⋅ 3 Baths

Designed to optimize water views of the Tred Avon and access to the community kayak launch and beach area is this to be built home. Centrally located between Easton and St Michaels and just a stone's throw from the Oxford Bellevue Ferry on the Tred Avon, one of Talbot County's premier waterfront communities with 13 half acre to 1.5 acre home sites. The community features its own private beach and kayak launch with nearby public park with playground and marina. Additional floor plans, options, and upgrades available. Some photos and renderings are for illustrative purposes only and may include additional upgrades.

25831 Turner Ave, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

$4,000,000

Exceptional opportunity to own a private Eastern Shore estate in Royal Oak. Anderby Hall, rooted in an original 1680 land grant, spans 12± breathtaking acres with over 3,260 feet of rip-rapped shoreline. Complete with a tidal pond, private cove, and an exclusive island peninsula connected by bridge, this estate offers unmatched privacy and natural beauty. Pass through the gated entrance to the 3,000± sq. ft. main residence featuring hand-hewn ceiling beams, antique pine floors, a great room with a fireplace, and a gourmet kitchen with a granite island. The main-floor primary suite boasts dual closets, while a second-floor office/den provides a quiet workspace. Nearly every room frames unobstructed views of Irish Creek. Step outside to brick walkways leading to a waterside custom pool. Boaters will appreciate the private deep-water dock (5' MLW) with two slips, offering quick access to the Choptank River. Outstanding property features include a 2,600 sq. ft. guest house, a tennis/pickleball court with a gazebo, a 30'x50' insulated 3-car garage, an additional 1-car garage/workshop, a new well, and a service shed. Enjoy an extraordinary coastal lifestyle surrounded by abundant wildlife, just minutes from St. Michaels and Easton.

3 Beds ⋅ 4 Baths

Exceptional opportunity to own a private Eastern Shore estate in Royal Oak. Anderby Hall, rooted in an original 1680 land grant, spans 12± breathtaking acres with over 3,260 feet of rip-rapped shoreline. Complete with a tidal pond, private cove, and an exclusive island peninsula connected by bridge, this estate offers unmatched privacy and natural beauty. Pass through the gated entrance to the 3,000± sq. ft. main residence featuring hand-hewn ceiling beams, antique pine floors, a great room with a fireplace, and a gourmet kitchen with a granite island. The main-floor primary suite boasts dual closets, while a second-floor office/den provides a quiet workspace. Nearly every room frames unobstructed views of Irish Creek. Step outside to brick walkways leading to a waterside custom pool. Boaters will appreciate the private deep-water dock (5' MLW) with two slips, offering quick access to the Choptank River. Outstanding property features include a 2,600 sq. ft. guest house, a tennis/pickleball court with a gazebo, a 30'x50' insulated 3-car garage, an additional 1-car garage/workshop, a new well, and a service shed. Enjoy an extraordinary coastal lifestyle surrounded by abundant wildlife, just minutes from St. Michaels and Easton.

5499 Anderby Hall Rd, Royal Oak

Listing courtesy of Coldwell Banker Realty. Contact:

How much is your home worth?

How much is your home worth?