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Experience the epitome of waterfront living in this stunning ranch-style residence nestled along the serene banks of the Choptank River. Spanning 1.35 acres, this exquisite property offers breathtaking river views that create a tranquil backdrop for your everyday life. The private dock invites you to indulge in water activities, from fishing to kayaking, ensuring endless adventures right at your doorstep. Step inside to discover a cozy ambiance highlighted by a charming brick fireplace, perfect for intimate gatherings. With 1,588 sq. ft. of thoughtfully designed space, this home seamlessly blends comfort and elegance. The expansive outdoor area is ideal for entertaining or simply unwinding while soaking in the picturesque surroundings. Embrace an exclusive lifestyle where nature meets sophistication, and every day feels like a vacation. This is more than a home; it's a sanctuary where luxury and leisure intertwine, offering you the ultimate escape. Don't miss your chance to own this riverfront gem!

2 Beds ⋅ 1 Baths

Experience the epitome of waterfront living in this stunning ranch-style residence nestled along the serene banks of the Choptank River. Spanning 1.35 acres, this exquisite property offers breathtaking river views that create a tranquil backdrop for your everyday life. The private dock invites you to indulge in water activities, from fishing to kayaking, ensuring endless adventures right at your doorstep. Step inside to discover a cozy ambiance highlighted by a charming brick fireplace, perfect for intimate gatherings. With 1,588 sq. ft. of thoughtfully designed space, this home seamlessly blends comfort and elegance. The expansive outdoor area is ideal for entertaining or simply unwinding while soaking in the picturesque surroundings. Embrace an exclusive lifestyle where nature meets sophistication, and every day feels like a vacation. This is more than a home; it's a sanctuary where luxury and leisure intertwine, offering you the ultimate escape. Don't miss your chance to own this riverfront gem!

3617 Willey Rd, Hurlock

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$95,000

Create your own private weekend getaway, hunting retreat or full-time residence with this 3 bedroom, 1 bath rancher featuring a newer well and septic system. The home needs TLC and is ready for your personal touches. Enjoy a private setting just a short drive from two marinas, public boat ramps, public hunting areas and Elijah’s General Store. Spend your days fishing, crabbing and hunting, then head home to unwind after a day outdoors. The property across the street, featuring 5.71 acres with a pond and access to Wingate Creek, is also available for sale (Land Listing MLS# MDDO2013492). The properties are listed separately and may be purchased together with an acceptable offer for a combined 7+ acres. Purchase both properties to enjoy opportunities for waterfowl, Sika deer and turkey hunting along with crabbing from the recreational parcel.

3 Beds ⋅ 1 Baths

Create your own private weekend getaway, hunting retreat or full-time residence with this 3 bedroom, 1 bath rancher featuring a newer well and septic system. The home needs TLC and is ready for your personal touches. Enjoy a private setting just a short drive from two marinas, public boat ramps, public hunting areas and Elijah’s General Store. Spend your days fishing, crabbing and hunting, then head home to unwind after a day outdoors. The property across the street, featuring 5.71 acres with a pond and access to Wingate Creek, is also available for sale (Land Listing MLS# MDDO2013492). The properties are listed separately and may be purchased together with an acceptable offer for a combined 7+ acres. Purchase both properties to enjoy opportunities for waterfowl, Sika deer and turkey hunting along with crabbing from the recreational parcel.

2249 Wingate Bishops Head Rd, Wingate

Listing courtesy of Meredith Fine Properties. Contact:

Kirwans Neck Rd - Kirwans Neck Rd - Waterfowl & Sika Deer, Church Creek

$1,990,000

Welcome to Holly Marsh, an exceptional waterfront sporting estate spanning over 87 acres across three adjoining parcels on Maryland’s Eastern Shore. Established waterfowl impoundments with a well and newly updated piping and gates (2026) provide excellent duck and goose hunting, while the property also offers great sika deer and turkey hunting, along with great fishing in the Honga River and Chesapeake Bay. Expansive water views, spectacular sunrises and sunsets and a private setting capture the outdoor traditions and natural beauty of the Eastern Shore. Complementing the land is a 5 bedroom, 4 bath waterfront home with ample space to gather after a day outdoors. A pool, hot tub, private beach and pier with boat lift provide additional opportunities to enjoy this remarkable private setting. Recent improvements include a fully renovated kitchen and laundry room with new appliances, fresh paint throughout, a new dock and boat lift, shoreline riprap and a resurfaced parking area (2024), followed by a new retractable pool cover and rescreened porch and hot tub area (2025). From mornings in the waterfowl impoundments to evenings overlooking the water, Holly Marsh brings together exceptional hunting, waterfront recreation and the comforts of home in a private Eastern Shore retreat.

Kirwans Neck Rd - Kirwans Neck Rd - Waterfowl & Sika Deer, Church Creek

Listing courtesy of Meredith Fine Properties. Contact:

$998,500

Set along the shores of Church Creek, this property spans 3.395+/- acres, offering a private setting, sweeping water views, and direct boating access. With over 470 feet of protected shoreline, a private dock with four feet of water depth, and a boat lift, the property embraces the best of Eastern Shore living. The approximately 3,400+/- square-foot home features four bedrooms and thoughtfully arranged living spaces designed to take full advantage of the waterfront setting. The main level offers an updated kitchen, spacious living and dining areas with creek views, and a stunning screened porch ideal for waterfront entertaining and quiet evenings overlooking the water. Upstairs, the primary suite features walk-in closets, a clawfoot soaking tub, a walk-in shower, and a private deck with sweeping views of Church Creek. Two additional bedrooms and a full bath complete the second floor. The third floor offers two additional rooms, providing flexible space for a home office, media room, or guest retreat. A detached two-car garage, three-bay kennel, and separate storage building add versatility to the property. Located just minutes from downtown Cambridge with restaurants, marinas, and community activities.

4 Beds ⋅ 3 Baths

Set along the shores of Church Creek, this property spans 3.395+/- acres, offering a private setting, sweeping water views, and direct boating access. With over 470 feet of protected shoreline, a private dock with four feet of water depth, and a boat lift, the property embraces the best of Eastern Shore living. The approximately 3,400+/- square-foot home features four bedrooms and thoughtfully arranged living spaces designed to take full advantage of the waterfront setting. The main level offers an updated kitchen, spacious living and dining areas with creek views, and a stunning screened porch ideal for waterfront entertaining and quiet evenings overlooking the water. Upstairs, the primary suite features walk-in closets, a clawfoot soaking tub, a walk-in shower, and a private deck with sweeping views of Church Creek. Two additional bedrooms and a full bath complete the second floor. The third floor offers two additional rooms, providing flexible space for a home office, media room, or guest retreat. A detached two-car garage, three-bay kennel, and separate storage building add versatility to the property. Located just minutes from downtown Cambridge with restaurants, marinas, and community activities.

4928 Gregory Rd, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact:

$1,990,000

Welcome to Holly Marsh, this exceptional waterfront estate spans over 87 acres across three adjoining parcels on Maryland’s Eastern Shore. Expansive water views, spectacular sunrises and sunsets create a remarkable setting for this 5 bedroom, 4 bath waterfront home. A pool, hot tub, private beach and pier with boat lift offer endless opportunities to relax, entertain and enjoy life on the water. Recent improvements include a fully renovated kitchen and laundry room with new appliances, fresh paint throughout, a new dock and boat lift, shoreline riprap and a resurfaced parking area (2024), plus a new retractable pool cover, rescreened porch and hot tub area (2025). Established waterfowl impoundments with well, updated with new piping and gates (2026), provide excellent duck and goose hunting, while great sika deer & turkey hunting can be enjoyed throughout the property. Rooted in the outdoor traditions of the Eastern Shore, Holly Marsh offers privacy, natural beauty and a waterfront retreat to share with family and friends.

5 Beds ⋅ 4 Baths

Welcome to Holly Marsh, this exceptional waterfront estate spans over 87 acres across three adjoining parcels on Maryland’s Eastern Shore. Expansive water views, spectacular sunrises and sunsets create a remarkable setting for this 5 bedroom, 4 bath waterfront home. A pool, hot tub, private beach and pier with boat lift offer endless opportunities to relax, entertain and enjoy life on the water. Recent improvements include a fully renovated kitchen and laundry room with new appliances, fresh paint throughout, a new dock and boat lift, shoreline riprap and a resurfaced parking area (2024), plus a new retractable pool cover, rescreened porch and hot tub area (2025). Established waterfowl impoundments with well, updated with new piping and gates (2026), provide excellent duck and goose hunting, while great sika deer & turkey hunting can be enjoyed throughout the property. Rooted in the outdoor traditions of the Eastern Shore, Holly Marsh offers privacy, natural beauty and a waterfront retreat to share with family and friends.

3214 Kirwans Neck Rd, Church Creek

Listing courtesy of Meredith Fine Properties. Contact:

$330,000

Experience effortless luxury at 2700 Willow Oak Drive, nestled within the prestigious waterfront setting of the Hyatt Regency community. Offered completely fully furnished with exquisite, high-end taste, this turnkey residence blends sophisticated coastal design with ultimate convenience. Step inside to discover a bright, beautifully curated interior where every detail has been thoughtfully considered. Enjoy stunning views, premium finishes, and a seamless layout designed for both relaxing and entertaining. Located just moments from the region's finest golf, dining, and resort amenities—this is resort-style living at its absolute finest. Simply pack your bags and move right in!

2 Beds ⋅ 2 Baths

Experience effortless luxury at 2700 Willow Oak Drive, nestled within the prestigious waterfront setting of the Hyatt Regency community. Offered completely fully furnished with exquisite, high-end taste, this turnkey residence blends sophisticated coastal design with ultimate convenience. Step inside to discover a bright, beautifully curated interior where every detail has been thoughtfully considered. Enjoy stunning views, premium finishes, and a seamless layout designed for both relaxing and entertaining. Located just moments from the region's finest golf, dining, and resort amenities—this is resort-style living at its absolute finest. Simply pack your bags and move right in!

2700 Willow Oak Dr Unit 411B, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact:

$1,495,000

Custom-built new construction on 3.73 acres along the Choptank River, offering a truly unique waterfront setting with views of the river, a peaceful backwater slough and a picturesque pond. With water and open landscape in nearly every direction, this property offers a sense of space and tranquility that is hard to duplicate. Step inside to an open, light-filled floor plan where thoughtful design and custom details are evident throughout. Wide-plank wood flooring flows through the main living areas, while vaulted ceilings and a striking fireplace create a dramatic focal point in the great room. Expansive glass doors open directly to a large patio, extending the living space outdoors and providing another place to enjoy the surrounding landscape and water views. The gourmet kitchen is a standout with custom cabinetry, an oversized island, stainless steel appliances, double wall ovens and a cleverly concealed butler’s pantry offering exceptional storage and prep space. Just off the eat-in kitchen area, a spacious screened porch takes full advantage of the peaceful setting and provides the perfect spot for outdoor dining, entertaining or simply relaxing and enjoying the view. Offering 3 spacious bedrooms and 3.5 baths, each bedroom has its own private ensuite bath, providing comfort and privacy for both owners and guests. The second-floor bedroom creates an especially inviting retreat with a private balcony overlooking the Choptank River and surrounding property. Distinctive tile selections, contemporary finishes and thoughtful architectural details throughout give this home a character all its own. Outdoor living is an integral part of this special property. Enjoy morning coffee on the screened porch, gather with friends on the patio, or retreat to the upstairs balcony to take in the river views. Nature lovers will appreciate the abundant birdlife, with eagles, osprey and other native birds frequently seen throughout the area. And as the day comes to a close, settle in for the spectacular sunsets that make the name “Sunset Cove” especially fitting. The waterfront lifestyle continues with a shared community pier on the Choptank River. Slips are planned, with one reserved for this property, providing future access for boating, fishing, crabbing and exploring the waterways of the Eastern Shore. An attached two-car garage, paved driveway and generous acreage complete this exceptional property. Custom new construction, 3.73 acres, remarkable waterfront, outdoor living spaces and future boat slip access come together in a setting that truly captures the beauty and lifestyle of Maryland’s Eastern Shore. Shown by appointment only.

3 Beds ⋅ 4 Baths

Custom-built new construction on 3.73 acres along the Choptank River, offering a truly unique waterfront setting with views of the river, a peaceful backwater slough and a picturesque pond. With water and open landscape in nearly every direction, this property offers a sense of space and tranquility that is hard to duplicate. Step inside to an open, light-filled floor plan where thoughtful design and custom details are evident throughout. Wide-plank wood flooring flows through the main living areas, while vaulted ceilings and a striking fireplace create a dramatic focal point in the great room. Expansive glass doors open directly to a large patio, extending the living space outdoors and providing another place to enjoy the surrounding landscape and water views. The gourmet kitchen is a standout with custom cabinetry, an oversized island, stainless steel appliances, double wall ovens and a cleverly concealed butler’s pantry offering exceptional storage and prep space. Just off the eat-in kitchen area, a spacious screened porch takes full advantage of the peaceful setting and provides the perfect spot for outdoor dining, entertaining or simply relaxing and enjoying the view. Offering 3 spacious bedrooms and 3.5 baths, each bedroom has its own private ensuite bath, providing comfort and privacy for both owners and guests. The second-floor bedroom creates an especially inviting retreat with a private balcony overlooking the Choptank River and surrounding property. Distinctive tile selections, contemporary finishes and thoughtful architectural details throughout give this home a character all its own. Outdoor living is an integral part of this special property. Enjoy morning coffee on the screened porch, gather with friends on the patio, or retreat to the upstairs balcony to take in the river views. Nature lovers will appreciate the abundant birdlife, with eagles, osprey and other native birds frequently seen throughout the area. And as the day comes to a close, settle in for the spectacular sunsets that make the name “Sunset Cove” especially fitting. The waterfront lifestyle continues with a shared community pier on the Choptank River. Slips are planned, with one reserved for this property, providing future access for boating, fishing, crabbing and exploring the waterways of the Eastern Shore. An attached two-car garage, paved driveway and generous acreage complete this exceptional property. Custom new construction, 3.73 acres, remarkable waterfront, outdoor living spaces and future boat slip access come together in a setting that truly captures the beauty and lifestyle of Maryland’s Eastern Shore. Shown by appointment only.

6016 Blue Heron Dr, East New Market

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

$799,000

Private Eastern Shore retreat with panoramic water views! This spacious newly renovated 6 bedroom, 4.5 bath home offers an abundance of room for family, guests and entertaining, with beautiful water views and a peaceful, private setting. Currently operating as an Airbnb and family retreat, the property is on track to generate approximately $40,000–$50,000 in rental income this year, with projected earnings of $50,000+ for 2027. This property offers flexibility for continued short-term rental use, a full-time residence and private getaway. The 40' x 60' pole barn with concrete floor and electric provides ample space for boats, vehicles, equipment, hobbies and storage. Close to marinas and public boat ramps for easy access to boating, fishing and crabbing. Property may convey furnished with an acceptable offer. Enjoy the Hoopers Island lifestyle! Bring your bikes and golf cart, enjoy nearby favorites like Old Salty's Restaurant and Blackwater National Wildlife Refuge.

6 Beds ⋅ 5 Baths

Private Eastern Shore retreat with panoramic water views! This spacious newly renovated 6 bedroom, 4.5 bath home offers an abundance of room for family, guests and entertaining, with beautiful water views and a peaceful, private setting. Currently operating as an Airbnb and family retreat, the property is on track to generate approximately $40,000–$50,000 in rental income this year, with projected earnings of $50,000+ for 2027. This property offers flexibility for continued short-term rental use, a full-time residence and private getaway. The 40' x 60' pole barn with concrete floor and electric provides ample space for boats, vehicles, equipment, hobbies and storage. Close to marinas and public boat ramps for easy access to boating, fishing and crabbing. Property may convey furnished with an acceptable offer. Enjoy the Hoopers Island lifestyle! Bring your bikes and golf cart, enjoy nearby favorites like Old Salty's Restaurant and Blackwater National Wildlife Refuge.

2144 Hoopersville Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact:

$385,000

Immaculate end-unit condo overlooks the Choptank River and the 18th Fairway. Willow Oaks in the Residences at River Marsh - adjacent to the Hyatt Regency - is your Eastern Shore home destination - as relaxing or full of adventure as you choose! Enjoy carefree, maintenace-free living in this turn-key 2BR/2BA, with a great floorplan and even greater views. Spacious great room with gorgeous wood floors, crown molding, and loads of natural light through the many windows over the golf course greens and glorious Choptank River. Formal dining room opens to the balcony. Large kitchen features an informal dining area, breakfast bar, pantry, and plentiful cabinetry. Primary bedroom also offers warm hardwood floors, walk-in closet, and a full, en-suite bath - soaking tub, custom tile shower. Welcoming guest bedroom and 2nd full bath with a tub/shower combo. Nice-sized laundry room includes a front-load washer and dryer, and storage space. Assigned parking space in the covered parking garage, and additional parking in the outdoor lot. The common areas in the building are well-maintained and stylishly-appointed. Lush, gorgeous grounds surround the building.Walking trails, lawn maintenace, common area maintenance, exterior building insurance and maintenace, snow removal, water, trash, reserve funds - all included in your monthly condo dues. Residents may purchase many different passes to enjoy the many amenities at the Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina - pools and spas, cabanas passes, private guest rooms, birthday party packages, multiple restaurants - all just a short stroll from home. Quick drive to Downtown Cambridge - a quintessential waterfront town on the Eastern Shore - full of incredible seafood, unique boutiques, arts and entertainment, tons of history, and local brews and restaurants. On the banks of the Choptank River, you'll be charmed by this gem of the Shore. Great central location - hour West to Annapolis, East to Ocean City beach and boardwalks, Assateague Island or the Delaware Beaches; half hour to Salisbury. Don't miss this unique opportunity to live the good life on the Eastern Shore! Sizes, taxes, distances approximate

2 Beds ⋅ 2 Baths

Immaculate end-unit condo overlooks the Choptank River and the 18th Fairway. Willow Oaks in the Residences at River Marsh - adjacent to the Hyatt Regency - is your Eastern Shore home destination - as relaxing or full of adventure as you choose! Enjoy carefree, maintenace-free living in this turn-key 2BR/2BA, with a great floorplan and even greater views. Spacious great room with gorgeous wood floors, crown molding, and loads of natural light through the many windows over the golf course greens and glorious Choptank River. Formal dining room opens to the balcony. Large kitchen features an informal dining area, breakfast bar, pantry, and plentiful cabinetry. Primary bedroom also offers warm hardwood floors, walk-in closet, and a full, en-suite bath - soaking tub, custom tile shower. Welcoming guest bedroom and 2nd full bath with a tub/shower combo. Nice-sized laundry room includes a front-load washer and dryer, and storage space. Assigned parking space in the covered parking garage, and additional parking in the outdoor lot. The common areas in the building are well-maintained and stylishly-appointed. Lush, gorgeous grounds surround the building.Walking trails, lawn maintenace, common area maintenance, exterior building insurance and maintenace, snow removal, water, trash, reserve funds - all included in your monthly condo dues. Residents may purchase many different passes to enjoy the many amenities at the Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina - pools and spas, cabanas passes, private guest rooms, birthday party packages, multiple restaurants - all just a short stroll from home. Quick drive to Downtown Cambridge - a quintessential waterfront town on the Eastern Shore - full of incredible seafood, unique boutiques, arts and entertainment, tons of history, and local brews and restaurants. On the banks of the Choptank River, you'll be charmed by this gem of the Shore. Great central location - hour West to Annapolis, East to Ocean City beach and boardwalks, Assateague Island or the Delaware Beaches; half hour to Salisbury. Don't miss this unique opportunity to live the good life on the Eastern Shore! Sizes, taxes, distances approximate

2700 Willow Oak Dr Unit 310C, Cambridge

Listing courtesy of EXP Realty, LLC. Contact:

$424,500

Nestled in the charming and historic West End of Cambridge, this delightful top floor 2-bedroom, 2-bathroom condominium at Oakley Beach offers a perfect blend of comfort and style. Built in 2005, this traditional unit features an inviting open floor plan, highlighted by beautiful hardwood floors and an abundance of natural light. The spacious kitchen boasts an island, ideal for casual dining or entertaining, while the adjoining dining area creates a warm atmosphere for gatherings. Relax in the cozy living room, complete with a gas fireplace, or step out onto your private balcony to enjoy unparalleled river views. The master suite features a luxurious walk-in shower, ensuring a spa-like experience at home. With convenient in-unit laundry and modern appliances-everyday living is a breeze. The exterior of the property is equally appealing, featuring well-maintained landscaping, sidewalks, and community amenities such as a refreshing outdoor pool. Enjoy the tranquility of waterfront living with direct access to the Choptank River, perfect for kayaking or leisurely strolls along the shore. Located in a vibrant neighborhood, you'll find local shops, dining, and recreational activities just moments away. With easy access to major routes and community docks, this home is a true gem for those seeking a peaceful yet connected lifestyle. Experience the best of riverfront living in this inviting condominium!

2 Beds ⋅ 2 Baths

Nestled in the charming and historic West End of Cambridge, this delightful top floor 2-bedroom, 2-bathroom condominium at Oakley Beach offers a perfect blend of comfort and style. Built in 2005, this traditional unit features an inviting open floor plan, highlighted by beautiful hardwood floors and an abundance of natural light. The spacious kitchen boasts an island, ideal for casual dining or entertaining, while the adjoining dining area creates a warm atmosphere for gatherings. Relax in the cozy living room, complete with a gas fireplace, or step out onto your private balcony to enjoy unparalleled river views. The master suite features a luxurious walk-in shower, ensuring a spa-like experience at home. With convenient in-unit laundry and modern appliances-everyday living is a breeze. The exterior of the property is equally appealing, featuring well-maintained landscaping, sidewalks, and community amenities such as a refreshing outdoor pool. Enjoy the tranquility of waterfront living with direct access to the Choptank River, perfect for kayaking or leisurely strolls along the shore. Located in a vibrant neighborhood, you'll find local shops, dining, and recreational activities just moments away. With easy access to major routes and community docks, this home is a true gem for those seeking a peaceful yet connected lifestyle. Experience the best of riverfront living in this inviting condominium!

5 Oakley St Unit 304/302, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact:

$1,590,000

PUBLIC AUCTION: Saturday, November 14, 2026, at 12 PM (noon), on site, with reserve. OPEN HOUSES: Saturday, October 31, 2026, from 12–2 PM, and Sunday, November 8, 2026, from 12–2 PM, or by appointment. AUCTION TERMS: A $30,000 deposit is due on the day of sale. Settlement must occur on or before 60 days from the sale date. Purchaser is responsible for all closing costs and transfer and settlement fees. Seller reserves the right to reject or accept any and all bids on the day of sale. NO BUYER’S PREMIUM. This property is being offered at public auction and is subject to the auction terms and conditions. Auctioneer: Bud Foxwell. A rare opportunity on the Honga River! Jenny Island Hunt Club offers a recreational property spanning 156 acres with an established hunt club marketed through Gage Outdoors Expeditions and short-term airbnb rental business. This active, turnkey operation generates six figures in income, with multiple bookings already in place for the upcoming 2026-2027 hunting season. The 7-bedroom, 3-bath waterfront lodge is rich in history and character. Enjoy incredible water views, stunning sunrises and sunsets, cozy fireplaces and abundant wildlife right outside your door. A private beach and 105-foot pier with boat lift provide direct access to the Honga River. The property borders Blackwater National Wildlife Refuge no-hunting zone, providing abundant wildlife habitat with no hunting pressure. Multiple offshore blinds provide excellent opportunities for waterfowl hunting. Enjoy premier waterfowl and Sika deer hunting, boating, kayaking, crabbing and excellent fishing right from the property. For outfitters looking to expand their business or anyone looking for an established hunting and recreational operation or a private family retreat, Jenny Island Hunt Club is a truly unique Eastern Shore property. Two Argos, a lawn mower, center console boat, several other pieces of equipment and home furnishings may convey with the property depending on an acceptable offer.

1510 Crocheron Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact:

$1,590,000

PUBLIC AUCTION: Saturday, November 14, 2026, at 12 PM (noon), on site, with reserve. OPEN HOUSES: Saturday, October 31, 2026, from 12–2 PM, and Sunday, November 8, 2026, from 12–2 PM, or by appointment. AUCTION TERMS: A $30,000 deposit is due on the day of sale. Settlement must occur on or before 60 days from the sale date. Purchaser is responsible for all closing costs and transfer and settlement fees. Seller reserves the right to reject or accept any and all bids on the day of sale. NO BUYER’S PREMIUM. This property is being offered at public auction and is subject to the auction terms and conditions. Auctioneer: Bud Foxwell. A rare opportunity on the Honga River! Jenny Island Hunt Club offers a recreational property spanning 156 acres with an established hunt club marketed through Gage Outdoors Expeditions and short-term airbnb rental business. This active, turnkey operation generates six figures in income, with multiple bookings already in place for the upcoming 2026-2027 hunting season. The 7-bedroom, 3-bath waterfront lodge is rich in history and character. Enjoy incredible water views, stunning sunrises and sunsets, cozy fireplaces and abundant wildlife right outside your door. A private beach and 105-foot pier with boat lift provide direct access to the Honga River. The property borders Blackwater National Wildlife Refuge no-hunting zone, providing abundant wildlife habitat with no hunting pressure. Multiple offshore blinds provide excellent opportunities for waterfowl hunting. Enjoy premier waterfowl and Sika deer hunting, boating, kayaking, crabbing and excellent fishing right from the property. For outfitters looking to expand their business or anyone looking for an established hunting and recreational operation or a private family retreat, Jenny Island Hunt Club is a truly unique Eastern Shore property. Two Argos, a lawn mower, center console boat, several other pieces of equipment and home furnishings may convey with the property depending on an acceptable offer.

7 Beds ⋅ 3 Baths

PUBLIC AUCTION: Saturday, November 14, 2026, at 12 PM (noon), on site, with reserve. OPEN HOUSES: Saturday, October 31, 2026, from 12–2 PM, and Sunday, November 8, 2026, from 12–2 PM, or by appointment. AUCTION TERMS: A $30,000 deposit is due on the day of sale. Settlement must occur on or before 60 days from the sale date. Purchaser is responsible for all closing costs and transfer and settlement fees. Seller reserves the right to reject or accept any and all bids on the day of sale. NO BUYER’S PREMIUM. This property is being offered at public auction and is subject to the auction terms and conditions. Auctioneer: Bud Foxwell. A rare opportunity on the Honga River! Jenny Island Hunt Club offers a recreational property spanning 156 acres with an established hunt club marketed through Gage Outdoors Expeditions and short-term airbnb rental business. This active, turnkey operation generates six figures in income, with multiple bookings already in place for the upcoming 2026-2027 hunting season. The 7-bedroom, 3-bath waterfront lodge is rich in history and character. Enjoy incredible water views, stunning sunrises and sunsets, cozy fireplaces and abundant wildlife right outside your door. A private beach and 105-foot pier with boat lift provide direct access to the Honga River. The property borders Blackwater National Wildlife Refuge no-hunting zone, providing abundant wildlife habitat with no hunting pressure. Multiple offshore blinds provide excellent opportunities for waterfowl hunting. Enjoy premier waterfowl and Sika deer hunting, boating, kayaking, crabbing and excellent fishing right from the property. For outfitters looking to expand their business or anyone looking for an established hunting and recreational operation or a private family retreat, Jenny Island Hunt Club is a truly unique Eastern Shore property. Two Argos, a lawn mower, center console boat, several other pieces of equipment and home furnishings may convey with the property depending on an acceptable offer.

1510 Crocheron Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact:

$499,000

Nestled in the charming West End neighborhood, this stunning Victorian home, originally built in 1920 and beautifully renovated over time, this lovely home offers a perfect blend of historic elegance and modern convenience. With 1,418 square feet of meticulously maintained living space, this detached residence is a true gem. Step inside to discover a warm and inviting interior featuring traditional floor plans that seamlessly connect the living and dining areas. The formal dining room is perfect for hosting gatherings, while the eat-in kitchen boasts upgraded countertops, an island for additional prep space, and recessed lighting that creates a bright and airy atmosphere. The wood flooring throughout adds a touch of sophistication, making every room feel cozy and welcoming. This home features three spacious bedrooms and two full bathrooms, ensuring ample space for relaxation and privacy. The main floor laundry, complete with washer and dryer, adds to the convenience of daily living. Outside, the property shines with its delightful wrap-around porch open to views of the river, as well as the municipal marina. The home also has a rear screened porch, perfect for enjoying morning coffee or evening gatherings. The exterior is enhanced by thoughtful features such as exterior lighting and low maintenance yard fencing. A garage provide additional storage and utility, while the gravel driveway offers off-street parking for two vehicles. One of the standout features of this property is its proximity to the serene Choptank River and Cambridge Creek, just a short walk away the downtown and restaurants. Imagine spending weekends exploring the nearby waterways or enjoying leisurely strolls into town. The neighborhood is rich with local amenities, including parks, shops, and dining options, making it an ideal location for those who appreciate a vibrant community atmosphere. With its captivating views of the creek and river, this home is not just a place to live; it's a lifestyle. Experience the perfect blend of historic charm and modern living in a neighborhood that offers both tranquility and convenience. Don't miss the opportunity to make this exquisite property your own! Some of the exterior photos were AI improved.

3 Beds ⋅ 2 Baths

Nestled in the charming West End neighborhood, this stunning Victorian home, originally built in 1920 and beautifully renovated over time, this lovely home offers a perfect blend of historic elegance and modern convenience. With 1,418 square feet of meticulously maintained living space, this detached residence is a true gem. Step inside to discover a warm and inviting interior featuring traditional floor plans that seamlessly connect the living and dining areas. The formal dining room is perfect for hosting gatherings, while the eat-in kitchen boasts upgraded countertops, an island for additional prep space, and recessed lighting that creates a bright and airy atmosphere. The wood flooring throughout adds a touch of sophistication, making every room feel cozy and welcoming. This home features three spacious bedrooms and two full bathrooms, ensuring ample space for relaxation and privacy. The main floor laundry, complete with washer and dryer, adds to the convenience of daily living. Outside, the property shines with its delightful wrap-around porch open to views of the river, as well as the municipal marina. The home also has a rear screened porch, perfect for enjoying morning coffee or evening gatherings. The exterior is enhanced by thoughtful features such as exterior lighting and low maintenance yard fencing. A garage provide additional storage and utility, while the gravel driveway offers off-street parking for two vehicles. One of the standout features of this property is its proximity to the serene Choptank River and Cambridge Creek, just a short walk away the downtown and restaurants. Imagine spending weekends exploring the nearby waterways or enjoying leisurely strolls into town. The neighborhood is rich with local amenities, including parks, shops, and dining options, making it an ideal location for those who appreciate a vibrant community atmosphere. With its captivating views of the creek and river, this home is not just a place to live; it's a lifestyle. Experience the perfect blend of historic charm and modern living in a neighborhood that offers both tranquility and convenience. Don't miss the opportunity to make this exquisite property your own! Some of the exterior photos were AI improved.

102 Vue De Leau St, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact:

$1,495,000

McNeil Pointe is a unique, coveted, 2-mile long peninsula of luxury homes. Nestled within the serene enclave of McKeil Pointe, this exquisite 7-bedroom, 5.5-bathroom farmhouse-style residence offers an unparalleled blend of luxury and comfort, set against a backdrop of lush landscapes and tranquil water features. Spanning approximately 5000+/- square feet, this home is a true sanctuary, designed for both relaxation and entertaining. Step inside to discover a warm and inviting interior, where you will find custom, hand-cut walnut floors throughout the open first floor and 2nd floor common areas. The heart of the home is the gourmet kitchen, featuring upgraded countertops, a large island, and top-of-the-line stainless steel appliances, including a six-burner stove and double ovens. The adjoining great room, complete with a cozy gas fireplace, creates an ideal space for gatherings, while the breakfast area invites leisurely mornings with views of the beautifully landscaped surroundings and water. Retreat to the primary suite, a luxurious haven with a bay front window that floods the space with natural light. The en-suite bathroom boasts a jetted tub, walk-in shower, and dual vanities, providing a spa-like experience at home. Each additional bedroom is generously sized, ensuring comfort for all. The exterior consists of 120' of deep, wraparound covered porches, with exposed rafters, beaded ceilings, a standing seam metal roof and stamped stone floors for all-season enjoyment. The remaining exterior of the property is equally impressive, featuring extensive hardscaping, multiple outdoor living spaces including a waterside deck, perfect for alfresco dining or simply soaking in the serene views. The heated in-ground pool offers a refreshing escape on warm days, while the private dock on Fishing Creek provides direct access to water activities such as kayaking, fishing, and swimming. Set on a sprawling 5.7-acre lot, the property is partly wooded and beautifully landscaped, offering privacy and tranquility. The gentle sounds of the nearby pond and the picturesque river views enhance the peaceful ambiance, making this home a true retreat from the hustle and bustle of everyday life. With ample parking, including a gravel driveway accommodating up to four vehicles, and security features, this residence combines luxury with practicality. Experience the exclusive lifestyle that this remarkable property offers, where every detail has been thoughtfully curated for your enjoyment and comfort. Additional features include, but are not limited to 3 zone central air. colonial and solid louvered doors throughout, 6 bedrooms with direct water views, and the 3rd Floor boasts a large Rec room, full bath and two bedrooms with four wide dormers.

7 Beds ⋅ 5 Baths

McNeil Pointe is a unique, coveted, 2-mile long peninsula of luxury homes. Nestled within the serene enclave of McKeil Pointe, this exquisite 7-bedroom, 5.5-bathroom farmhouse-style residence offers an unparalleled blend of luxury and comfort, set against a backdrop of lush landscapes and tranquil water features. Spanning approximately 5000+/- square feet, this home is a true sanctuary, designed for both relaxation and entertaining. Step inside to discover a warm and inviting interior, where you will find custom, hand-cut walnut floors throughout the open first floor and 2nd floor common areas. The heart of the home is the gourmet kitchen, featuring upgraded countertops, a large island, and top-of-the-line stainless steel appliances, including a six-burner stove and double ovens. The adjoining great room, complete with a cozy gas fireplace, creates an ideal space for gatherings, while the breakfast area invites leisurely mornings with views of the beautifully landscaped surroundings and water. Retreat to the primary suite, a luxurious haven with a bay front window that floods the space with natural light. The en-suite bathroom boasts a jetted tub, walk-in shower, and dual vanities, providing a spa-like experience at home. Each additional bedroom is generously sized, ensuring comfort for all. The exterior consists of 120' of deep, wraparound covered porches, with exposed rafters, beaded ceilings, a standing seam metal roof and stamped stone floors for all-season enjoyment. The remaining exterior of the property is equally impressive, featuring extensive hardscaping, multiple outdoor living spaces including a waterside deck, perfect for alfresco dining or simply soaking in the serene views. The heated in-ground pool offers a refreshing escape on warm days, while the private dock on Fishing Creek provides direct access to water activities such as kayaking, fishing, and swimming. Set on a sprawling 5.7-acre lot, the property is partly wooded and beautifully landscaped, offering privacy and tranquility. The gentle sounds of the nearby pond and the picturesque river views enhance the peaceful ambiance, making this home a true retreat from the hustle and bustle of everyday life. With ample parking, including a gravel driveway accommodating up to four vehicles, and security features, this residence combines luxury with practicality. Experience the exclusive lifestyle that this remarkable property offers, where every detail has been thoughtfully curated for your enjoyment and comfort. Additional features include, but are not limited to 3 zone central air. colonial and solid louvered doors throughout, 6 bedrooms with direct water views, and the 3rd Floor boasts a large Rec room, full bath and two bedrooms with four wide dormers.

5207 Brooks Rd, Woolford

Listing courtesy of Benson & Mangold, LLC. Contact:

$189,900

Rare land offering on Horns Point Road! One of Dorchester County's most sought after neighborhoods - just outside town limits. Tranquil views over fields to the Choptank River. Partially wooded. Health Dept. approved and ready to go! Plans subject to review by the sellers. Lot #5 can be purchased separately for $98,750.

Horns Point Road, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact:

$98,750

Rare land offering on Horns Point Road! Build on this individual parcel or purchase it together with neighboring Lot #4 (Tax ID# 07-239823 - 2.04+/- acres) for $189,900. Perfect setting for your custom home design. Inquire today for more details!

Horns Point Road, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact:

$665,000

Welcome to Fishing Creek, where Chesapeake Bay waterfront living takes center stage. This beautifully renovated coastal retreat offers approximately 138 feet of water frontage, extensive riprap shoreline protection and incredible views in nearly every direction. Step outside and enjoy an impressive 155-foot private pier with boat lift, jet ski lift, electric, lighting and plumbing, creating the perfect setup for boating, fishing, crabbing and everything the Eastern Shore lifestyle has to offer. Inside, the home has been thoughtfully transformed with an updated kitchen and appliances, renovated tile bathroom, updated flooring, recessed lighting, a gorgeous 200+ sq. ft. sunroom surrounded by windows and water views. Wake up to sunrise over the harbor, unwind with sunsets over the Chesapeake, and enjoy the water from nearly every room. The investment into this property goes far beyond what you can see. Major improvements include a new septic field, extensive riprap shoreline stabilization, upgraded pier infrastructure with boat lift, jet ski lift, updated dock, electric on dock and plumbing, a custom Amish built two-story bunkhouse with insulation, flooring and electric, a 200-amp electrical upgrade, renovated bathroom, new kitchen appliances, waterfront hardscape patio, exterior improvements and a new well pump and many more. These are the big-ticket improvements that deliver true peace of mind. Peaceful, private and built to enjoy the Chesapeake, this is more than a waterfront home. It’s your own Eastern Shore escape.

2 Beds ⋅ 1 Baths

Welcome to Fishing Creek, where Chesapeake Bay waterfront living takes center stage. This beautifully renovated coastal retreat offers approximately 138 feet of water frontage, extensive riprap shoreline protection and incredible views in nearly every direction. Step outside and enjoy an impressive 155-foot private pier with boat lift, jet ski lift, electric, lighting and plumbing, creating the perfect setup for boating, fishing, crabbing and everything the Eastern Shore lifestyle has to offer. Inside, the home has been thoughtfully transformed with an updated kitchen and appliances, renovated tile bathroom, updated flooring, recessed lighting, a gorgeous 200+ sq. ft. sunroom surrounded by windows and water views. Wake up to sunrise over the harbor, unwind with sunsets over the Chesapeake, and enjoy the water from nearly every room. The investment into this property goes far beyond what you can see. Major improvements include a new septic field, extensive riprap shoreline stabilization, upgraded pier infrastructure with boat lift, jet ski lift, updated dock, electric on dock and plumbing, a custom Amish built two-story bunkhouse with insulation, flooring and electric, a 200-amp electrical upgrade, renovated bathroom, new kitchen appliances, waterfront hardscape patio, exterior improvements and a new well pump and many more. These are the big-ticket improvements that deliver true peace of mind. Peaceful, private and built to enjoy the Chesapeake, this is more than a waterfront home. It’s your own Eastern Shore escape.

2530 Hoopers Island Rd, Fishing Creek

Listing courtesy of Keller Williams Flagship. Contact:

$1,800,000

Eastern Shore Waterfront Building Lot. Discover a rare opportunity to own one of the Eastern Shore’s beautiful waterfront lots. Located in the small subdivision of Camelot, this 3.5-acre building lot offers breathtaking sunset views and an exceptional setting to create your dream home. Tucked along Fishing Creek just off the Little Choptank River, the property provides peaceful water views, privacy, and natural beauty. As shown in the photographs, the adjoining property has recently been improved with a newly built home and pier, further enhancing the appeal and potential of this location. Despite its tranquil setting, the lot is conveniently located just a few miles from downtown Cambridge, offering easy access to shopping, dining, entertainment, and local attractions. Whether you envision a primary residence or a weekend retreat, this property offers an unparalleled canvas for your vision and the opportunity to fully embrace the Eastern Shore and Bay lifestyle. Due diligence is recommended for any building lot. Buyers are encouraged to contact the Dorchester County office for information regarding new construction requirements. Permit approved to: Construct a 140-foot long by 6-foot-wide timber pier, a boatlift with associated piles, and two mooring piles extending a maximum of 140 feet channel ward of the mean high-water line. Schedule a tour today - do not enter the property with an appointment or a representative.

5200 Travelers Rest Rd, Cambridge

Listing courtesy of Taylor Properties. Contact:

$369,900

Waterfront living at its best! This home features 3 bedrooms and 3.5 bathrooms which includes 2 primary suites allowing your guests to have an in-suite bathroom. The property also has 2 private decks overlooking the Warwick River and a pier with a recently installed boat lift. This unit was built in 2001 and has a sprinkler system, a large family room with a gas fireplace, new roof and a new boardwalk is being installed soon. The home is in very good condition and ready to move into. Enjoy beautiful sunsets and quick access to the Choptank River and Chesapeake Bay. There are many nearby beaches, restaurants and shopping. This is a must see!!

3 Beds ⋅ 4 Baths

Waterfront living at its best! This home features 3 bedrooms and 3.5 bathrooms which includes 2 primary suites allowing your guests to have an in-suite bathroom. The property also has 2 private decks overlooking the Warwick River and a pier with a recently installed boat lift. This unit was built in 2001 and has a sprinkler system, a large family room with a gas fireplace, new roof and a new boardwalk is being installed soon. The home is in very good condition and ready to move into. Enjoy beautiful sunsets and quick access to the Choptank River and Chesapeake Bay. There are many nearby beaches, restaurants and shopping. This is a must see!!

101 Main, Secretary

Listing courtesy of The Glocker Group Realty Results. Contact:

$2,950,000

Looking for a business opportunity, want to expand your business? This exceptional property offers outstanding income and business potential, including opportunities for a private retreat, vacation rental, event or wedding venue, guided hunting and fishing, sporting clay, kayak, water sports experiences and other outdoor recreational offerings. Introducing Riverside Lodge, a one-of-a-kind private waterfront sporting estate on Maryland's Eastern Shore. Spanning 386+/- acres overlooking the Honga River and the Chesapeake Bay, this extraordinary retreat is anchored by a beautifully appointed 5 bedroom, 5.5 bath waterfront lodge designed for both entertaining and comfortable extended stays or full time residence. Surrounded by exceptional wildlife habitat, Riverside Lodge blends timeless Eastern Shore tradition with premier waterfowl hunting, Sika deer hunting, world-class fishing, boating, crabbing and breathtaking sunrises and sunsets on Hoopers Island. Along with several established blind sites, an offshore blind, inlets and ponds, the property also features a managed waterfowl impoundment with a dedicated well. Located in the heart of the Atlantic Flyway, Riverside Lodge offers exceptional opportunities to hunt a variety of migrating waterfowl including canvasbacks, bluebills, redheads, black ducks, mallards, teal, wood ducks, buffleheads and Canada geese. The surrounding waters of the Honga River and Chesapeake Bay offer world class fishing for striped bass (rockfish), red and black drum, cobia, speckled trout, bluefish, flounder, perch, spanish mackerel along with outstanding crabbing and oystering from your own shoreline.

1713 Doeller Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact:

$2,950,000

Introducing Riverside Lodge, a one-of-a-kind private waterfront sporting estate on Maryland's Eastern Shore. Spanning 386+/- acres overlooking the Honga River and the Chesapeake Bay, this extraordinary retreat is anchored by a beautifully appointed 5 bedroom, 5.5 bath waterfront lodge designed for both entertaining and comfortable extended stays or full time residence. Surrounded by exceptional wildlife habitat, Riverside Lodge blends timeless Eastern Shore tradition with premier waterfowl hunting, Sika deer hunting, world-class fishing, boating, crabbing and breathtaking sunrises and sunsets on Hoopers Island. Along with several established blind sites, an offshore blind, inlets and ponds, the property also features a managed waterfowl impoundment with a dedicated well. Located in the heart of the Atlantic Flyway, Riverside Lodge offers exceptional opportunities to hunt a variety of migrating waterfowl including canvasbacks, bluebills, redheads, black ducks, mallards, teal, wood ducks, buffleheads and Canada geese. The surrounding waters of the Honga River and Chesapeake Bay offer world class fishing for striped bass (rockfish), red and black drum, cobia, speckled trout, bluefish, flounder, perch, spanish mackerel along with outstanding crabbing and oystering from your own shoreline. This exceptional residence is designed for entertaining family and friends and offers business and income potential. Ideal as a private retreat, luxury vacation rental, event or wedding venue or destination for guided hunting, fishing, sporting clays, kayaking and other outdoor recreation, the possibilities are endless.

1713 Doeller Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact:

$2,950,000

Introducing Riverside Lodge, a one-of-a-kind private waterfront sporting estate on Maryland's Eastern Shore. Spanning 386+/- acres overlooking the Honga River and the Chesapeake Bay, this extraordinary retreat is anchored by a beautifully appointed 5 bedroom, 5.5 bath waterfront lodge designed for both entertaining and comfortable extended stays or full time residence. Surrounded by exceptional wildlife habitat, Riverside Lodge blends timeless Eastern Shore tradition with premier waterfowl hunting, Sika deer hunting, world-class fishing, boating, crabbing and breathtaking sunrises and sunsets on Hoopers Island. Along with several established blind sites, an offshore blind, inlets and ponds, the property also features a managed waterfowl impoundment with a dedicated well. Located in the heart of the Atlantic Flyway, Riverside Lodge offers exceptional opportunities to hunt a variety of migrating waterfowl including canvasbacks, bluebills, redheads, black ducks, mallards, teal, wood ducks, buffleheads and Canada geese. The surrounding waters of the Honga River and Chesapeake Bay offer world class fishing for striped bass (rockfish), red and black drum, cobia, speckled trout, bluefish, flounder, perch, spanish mackerel along with outstanding crabbing and oystering from your own shoreline. This exceptional residence is designed for entertaining family and friends and offers business and income potential. Ideal as a private retreat, luxury vacation rental, event or wedding venue or destination for guided hunting, fishing, sporting clays, kayaking and other outdoor recreation, the possibilities are endless.

5 Beds ⋅ 6 Baths

Introducing Riverside Lodge, a one-of-a-kind private waterfront sporting estate on Maryland's Eastern Shore. Spanning 386+/- acres overlooking the Honga River and the Chesapeake Bay, this extraordinary retreat is anchored by a beautifully appointed 5 bedroom, 5.5 bath waterfront lodge designed for both entertaining and comfortable extended stays or full time residence. Surrounded by exceptional wildlife habitat, Riverside Lodge blends timeless Eastern Shore tradition with premier waterfowl hunting, Sika deer hunting, world-class fishing, boating, crabbing and breathtaking sunrises and sunsets on Hoopers Island. Along with several established blind sites, an offshore blind, inlets and ponds, the property also features a managed waterfowl impoundment with a dedicated well. Located in the heart of the Atlantic Flyway, Riverside Lodge offers exceptional opportunities to hunt a variety of migrating waterfowl including canvasbacks, bluebills, redheads, black ducks, mallards, teal, wood ducks, buffleheads and Canada geese. The surrounding waters of the Honga River and Chesapeake Bay offer world class fishing for striped bass (rockfish), red and black drum, cobia, speckled trout, bluefish, flounder, perch, spanish mackerel along with outstanding crabbing and oystering from your own shoreline. This exceptional residence is designed for entertaining family and friends and offers business and income potential. Ideal as a private retreat, luxury vacation rental, event or wedding venue or destination for guided hunting, fishing, sporting clays, kayaking and other outdoor recreation, the possibilities are endless.

1713 Doeller Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact:

2404 And 2407 Hoopers Island Rd, Fishing Creek

$575,000

Escape to the unspoiled beauty of Hoopers Island, where peaceful waterfront living and world-class fishing, crabbing, and boating are part of everyday life. Situated on a beautifully landscaped 1.06-acre corner lot, this charming 3-bedroom, 2-bath home offers the ideal Eastern Shore retreat with generous indoor and outdoor spaces designed for gathering with family and friends. The heart of the home is a beautifully appointed kitchen featuring granite countertops, abundant cabinetry with under-cabinet lighting, a center island, double wall ovens, gas cooktop, wet bar, and custom wood ceilings. Original pocket doors, warm wood accents, and pellet stoves add timeless character throughout, while the spacious sunroom with skylights and a stone hearth creates a cozy place to unwind year-round. Upstairs offers three bedrooms, a full bath, and a loft that comfortably accommodates additional guests, making this an ideal full-time residence or weekend getaway. Two storage sheds provide ample space for boating and outdoor equipment. Included in the sale is a rare additional 0.13-acre Commercial Maritime waterfront parcel featuring a 100-foot pier with approximately 5 feet of water depth, multiple boat slips, and endless opportunities to enjoy the Chesapeake Bay lifestyle. Whether your passion is offshore fishing, crabbing, kayaking, or simply watching the sunset over the water, this property is ready for your next adventure. Owners also have a duck blind permit with site right off the property for hunter enthusiasts. What more could you ask for? Located just minutes from local favorites including Old Salty's Restaurant, Hoopers Island General Store, and Madhouse Oysters, this exceptional offering combines authentic Eastern Shore charm with the waterfront lifestyle so many dream of—but few ever find.

3 Beds ⋅ 2 Baths

Escape to the unspoiled beauty of Hoopers Island, where peaceful waterfront living and world-class fishing, crabbing, and boating are part of everyday life. Situated on a beautifully landscaped 1.06-acre corner lot, this charming 3-bedroom, 2-bath home offers the ideal Eastern Shore retreat with generous indoor and outdoor spaces designed for gathering with family and friends. The heart of the home is a beautifully appointed kitchen featuring granite countertops, abundant cabinetry with under-cabinet lighting, a center island, double wall ovens, gas cooktop, wet bar, and custom wood ceilings. Original pocket doors, warm wood accents, and pellet stoves add timeless character throughout, while the spacious sunroom with skylights and a stone hearth creates a cozy place to unwind year-round. Upstairs offers three bedrooms, a full bath, and a loft that comfortably accommodates additional guests, making this an ideal full-time residence or weekend getaway. Two storage sheds provide ample space for boating and outdoor equipment. Included in the sale is a rare additional 0.13-acre Commercial Maritime waterfront parcel featuring a 100-foot pier with approximately 5 feet of water depth, multiple boat slips, and endless opportunities to enjoy the Chesapeake Bay lifestyle. Whether your passion is offshore fishing, crabbing, kayaking, or simply watching the sunset over the water, this property is ready for your next adventure. Owners also have a duck blind permit with site right off the property for hunter enthusiasts. What more could you ask for? Located just minutes from local favorites including Old Salty's Restaurant, Hoopers Island General Store, and Madhouse Oysters, this exceptional offering combines authentic Eastern Shore charm with the waterfront lifestyle so many dream of—but few ever find.

2404 And 2407 Hoopers Island Rd, Fishing Creek

Listing courtesy of Sharon Real Estate P.C.. Contact:

$299,000

Welcome to 2517 Old House Point Rd, one of the cutest homes in Fishing Creek. Sitting on elevated ground this three bedroom, one bathroom home has water views from the front and back yard. Large garage you could keep a boat or kayaks and bikes with loft and lean to. Quiet area with relaxing feeling.

3 Beds ⋅ 1 Baths

Welcome to 2517 Old House Point Rd, one of the cutest homes in Fishing Creek. Sitting on elevated ground this three bedroom, one bathroom home has water views from the front and back yard. Large garage you could keep a boat or kayaks and bikes with loft and lean to. Quiet area with relaxing feeling.

2517 Old House Point Rd, Fishing Creek

Listing courtesy of Coldwell Banker Realty. Contact:

$8,950,000

Parsons Creek Farm - A 255+/- Acre, Multi-Residence, Deep-Water, Waterfowl & Wildlife Estate at the Confluence of Parsons Creek and the Little Choptank River This once-in-a-lifetime Chesapeake Bay legacy holding is set upon 255.47 extraordinary acres of waterfront, wetlands, upland forest, and meticulously curated wildlife habitat making Parsons Creek Farm one of the most sophisticated private estates on Maryland's Eastern Shore. Masterfully blending historic charm, modern craftsmanship, high-performance land management, and recreational luxury, this turnkey, multi-residence compound stands unrivaled in scale, ecological design, and architectural execution. Positioned at the union of Parsons Creek and the Little Choptank River, the property enjoys nearly a mile of sandy, private shoreline, deep-water access, expansive water vistas, and complete seclusion - yet remains within a short drive to Cambridge, Annapolis, Baltimore, Washington, and the greater Mid-Atlantic corridor. A series of thoughtfully positioned structures - each with its own architectural identity - combine to create a private compound capable of sleeping more than 24 guests in total comfort. Elegantly sited to capture uninterrupted views across impoundments, woodlands, and water, the primary residence blends historic Maryland character with refined luxury. This meticulously designed, 9,583 sq. ft. luxury residence boasts an impressive array of distinct living areas, creating a home of both grand scale and exceptional comfort for family living and entertaining. The expansive property also features a charming, fully renovated, private 1,500 sq. ft. Cape Cod–style guest house that extends a warm welcome to visitors, and a third two-story residence complete with a full bedroom suite, full bathroom, laundry, and sweeping picture windows overlooking one of the ponds. Part of the estate's recreational opportunities is an over-the-water bar and game room, a gathering place where family and friends can cast a line into the pond while enjoying the comforts of a private lounge. Equestrian enthusiasts and entertainers alike will appreciate the impressive stable complex, complete with second-floor luxurious living quarters, a spacious game room, and full bar. Balconies at each end capture sweeping views of the surrounding woodland and water, creating an atmosphere of timeless elegance. Whether envisioned as a generational family compound, a private sporting estate, a conservation-forward investment property, or an exclusive corporate/hospitality retreat, Parsons Creek Farm offers a combination of luxury, ecological engineering, and rural waterfront beauty unmatched anywhere in the Mid-Atlantic. This remarkable waterfront estate is a unique opportunity that unites world-class waterfowl and upland hunting, meticulous wildlife management, and refined living—enhanced by impressive income potential. Having identified his replacement property, the seller is prepared to move forward and welcomes qualified offers.

24 Beds ⋅ 13 Baths

Parsons Creek Farm - A 255+/- Acre, Multi-Residence, Deep-Water, Waterfowl & Wildlife Estate at the Confluence of Parsons Creek and the Little Choptank River This once-in-a-lifetime Chesapeake Bay legacy holding is set upon 255.47 extraordinary acres of waterfront, wetlands, upland forest, and meticulously curated wildlife habitat making Parsons Creek Farm one of the most sophisticated private estates on Maryland's Eastern Shore. Masterfully blending historic charm, modern craftsmanship, high-performance land management, and recreational luxury, this turnkey, multi-residence compound stands unrivaled in scale, ecological design, and architectural execution. Positioned at the union of Parsons Creek and the Little Choptank River, the property enjoys nearly a mile of sandy, private shoreline, deep-water access, expansive water vistas, and complete seclusion - yet remains within a short drive to Cambridge, Annapolis, Baltimore, Washington, and the greater Mid-Atlantic corridor. A series of thoughtfully positioned structures - each with its own architectural identity - combine to create a private compound capable of sleeping more than 24 guests in total comfort. Elegantly sited to capture uninterrupted views across impoundments, woodlands, and water, the primary residence blends historic Maryland character with refined luxury. This meticulously designed, 9,583 sq. ft. luxury residence boasts an impressive array of distinct living areas, creating a home of both grand scale and exceptional comfort for family living and entertaining. The expansive property also features a charming, fully renovated, private 1,500 sq. ft. Cape Cod–style guest house that extends a warm welcome to visitors, and a third two-story residence complete with a full bedroom suite, full bathroom, laundry, and sweeping picture windows overlooking one of the ponds. Part of the estate's recreational opportunities is an over-the-water bar and game room, a gathering place where family and friends can cast a line into the pond while enjoying the comforts of a private lounge. Equestrian enthusiasts and entertainers alike will appreciate the impressive stable complex, complete with second-floor luxurious living quarters, a spacious game room, and full bar. Balconies at each end capture sweeping views of the surrounding woodland and water, creating an atmosphere of timeless elegance. Whether envisioned as a generational family compound, a private sporting estate, a conservation-forward investment property, or an exclusive corporate/hospitality retreat, Parsons Creek Farm offers a combination of luxury, ecological engineering, and rural waterfront beauty unmatched anywhere in the Mid-Atlantic. This remarkable waterfront estate is a unique opportunity that unites world-class waterfowl and upland hunting, meticulous wildlife management, and refined living—enhanced by impressive income potential. Having identified his replacement property, the seller is prepared to move forward and welcomes qualified offers.

964 Taylors Island Rd, Madison

Listing courtesy of National Land Realty, LLC. Contact:

$297,000

Build your dream home or invest. This is the only one of kind. 1.8 acres on two combined deeded parcels on the quiet and serine Church Creek in Woolford MD, 1609 Heliport Rd has a current tidewater buffer setback variance (BOA Case #2109), allowing for the construction of a dwelling inside the typical 100-foot setback. Most importantly, this variance does not expire and transfers directly to the new owner, providing a unique opportunity that is nearly impossible to find with waterfront development. The most significant hurdle to building on waterfront is permitting for permit septic. This property has PUBLIC SEWER. Please call to learn more.Thank you for visiting my listing.

1609 Heliport Rd, Woolford

Listing courtesy of Keller Williams Realty Delmarva. Contact:

$284,999

Historic District charm meets everyday convenience at 113 Willis Street. This adorable circa-1916 Victorian sits just down the street from the Choptank River and close to the heart of downtown Cambridge, where you can enjoy local restaurants, shops, parks, marinas, waterfront events, and the character that makes this Eastern Shore town so special. Inside, this three-bedroom home blends classic early 20th-century charm with practical updates, including newer windows, roof, siding, drywall, electrical wiring, and central air, an uncommon and valuable bonus in many historic homes. The welcoming wraparound porch gives the home instant curb appeal, while the fully fenced yard, alley access, off-street parking, and garage/workshop add everyday functionality that is hard to find in this setting. Whether you need storage, hobby space, tools, bikes, or a spot for weekend projects, the garage/workshop gives you flexibility beyond the main house. Cute, comfortable, updated, and full of Cambridge character, this home offers historic charm, modern comfort, and downtown convenience all in one very lovable package.

3 Beds ⋅ 2 Baths

Historic District charm meets everyday convenience at 113 Willis Street. This adorable circa-1916 Victorian sits just down the street from the Choptank River and close to the heart of downtown Cambridge, where you can enjoy local restaurants, shops, parks, marinas, waterfront events, and the character that makes this Eastern Shore town so special. Inside, this three-bedroom home blends classic early 20th-century charm with practical updates, including newer windows, roof, siding, drywall, electrical wiring, and central air, an uncommon and valuable bonus in many historic homes. The welcoming wraparound porch gives the home instant curb appeal, while the fully fenced yard, alley access, off-street parking, and garage/workshop add everyday functionality that is hard to find in this setting. Whether you need storage, hobby space, tools, bikes, or a spot for weekend projects, the garage/workshop gives you flexibility beyond the main house. Cute, comfortable, updated, and full of Cambridge character, this home offers historic charm, modern comfort, and downtown convenience all in one very lovable package.

113 Willis St, Cambridge

Listing courtesy of Keller Williams Flagship. Contact:

$450,000

Exceptional opportunity to create your own Eastern Shore waterfront retreat with approximately 6' MLW—a standout feature for sailing enthusiasts and boaters seeking dependable deep-water access. Set in a welcoming waterfront community with a relaxed, laid-back atmosphere, this property offers beautiful water views and an impressive collection of boating amenities, making it an ideal home base for exploring the Chesapeake Bay and surrounding waterways. The private pier is the centerpiece of the property, offering approximately 6 feet of mean low water, a lookout platform, and four boat lifts—including two 1,500-lb jet ski lifts, an 8,000-lb lift, and a 20,000-lb lift installed in 2022. Whether your passion is sailing, power boating, fishing, crabbing, kayaking, or simply spending your days by the water, the infrastructure is already in place to embrace the waterfront lifestyle. The 1-bedroom home is fully ADA-compliant and offers an enclosed waterside porch perfect for relaxing and taking in the view. The renovated full bath features a roll-in tiled shower, quartz vanity, tile flooring, and barn doors designed for accessibility and ease of use. A wheelchair ramp and lift also convey. Recent improvements include a 50-year architectural shingle roof installed in 2023 with transferable warranty and a new well installed in 2024, along with the convenience of public sewer service. A detached garage/workshop with concrete floors and a newer electrical panel provides excellent space for storage, hobbies, or boating equipment. Plumbing in the workshop is currently disconnected but could be reconnected by the new owner. An additional waterside storage shed near the pier is ideal for kayaks, fishing gear, and outdoor equipment. Bring your vision and make this waterfront property your own. With deep water, substantial boating infrastructure, and beautiful views, this is a unique opportunity to establish a Chesapeake Bay getaway tailored to the way you want to enjoy the water. Property is being sold as-is. Appointment required for all showings.

1 Beds ⋅ 1 Baths

Exceptional opportunity to create your own Eastern Shore waterfront retreat with approximately 6' MLW—a standout feature for sailing enthusiasts and boaters seeking dependable deep-water access. Set in a welcoming waterfront community with a relaxed, laid-back atmosphere, this property offers beautiful water views and an impressive collection of boating amenities, making it an ideal home base for exploring the Chesapeake Bay and surrounding waterways. The private pier is the centerpiece of the property, offering approximately 6 feet of mean low water, a lookout platform, and four boat lifts—including two 1,500-lb jet ski lifts, an 8,000-lb lift, and a 20,000-lb lift installed in 2022. Whether your passion is sailing, power boating, fishing, crabbing, kayaking, or simply spending your days by the water, the infrastructure is already in place to embrace the waterfront lifestyle. The 1-bedroom home is fully ADA-compliant and offers an enclosed waterside porch perfect for relaxing and taking in the view. The renovated full bath features a roll-in tiled shower, quartz vanity, tile flooring, and barn doors designed for accessibility and ease of use. A wheelchair ramp and lift also convey. Recent improvements include a 50-year architectural shingle roof installed in 2023 with transferable warranty and a new well installed in 2024, along with the convenience of public sewer service. A detached garage/workshop with concrete floors and a newer electrical panel provides excellent space for storage, hobbies, or boating equipment. Plumbing in the workshop is currently disconnected but could be reconnected by the new owner. An additional waterside storage shed near the pier is ideal for kayaks, fishing gear, and outdoor equipment. Bring your vision and make this waterfront property your own. With deep water, substantial boating infrastructure, and beautiful views, this is a unique opportunity to establish a Chesapeake Bay getaway tailored to the way you want to enjoy the water. Property is being sold as-is. Appointment required for all showings.

5023 Russell Rd, Woolford

Listing courtesy of Sharon Real Estate P.C.. Contact:

$599,000

Welcome to your waterfront paradise! Home boasts nice open living room /dining room area with gorgeous views of the water from the large bay window, and a food bar dividing the rooms. The primary suite allows access to the enclosed year- round sunroom with expansive views of the water. The home features secondary bedroom with water view, a second full bath, a kitchen with a double wall oven, separate cooktop, a bistro area, and a large pantry. Laundry room. Natural hardwood floors throughout. Insulated attic. Encapsulated crawlspace with new sump pump and dehumidifier. And a welcoming 26' x 6' front porch. Property includes a 2 room and bath cottage. The home is situated on +/- .50 acre. Pier has a 9,000 lb boatlift, swim ladder, water and electric. Beautiful pier lights. This home is a Must-See to truly appreciate all it has to offer. Sellers are offering an assumable FHA mortgage at 5.25% to qualified buyers. Buyer will be responsible to pay sellers the difference between the assumable mortgage amount and the contracted sale price of the home. Sitting on Fishing Creek and runs into the Little Choptank, which runs into the Chesapeake Bay. This home has endless possibilities from Airbnb rental income to a wedding venue; living in the house and renting out the cottage... This property has the potential to create revenue and give you a great return on your investment. Imagine......

2 Beds ⋅ 2 Baths

Welcome to your waterfront paradise! Home boasts nice open living room /dining room area with gorgeous views of the water from the large bay window, and a food bar dividing the rooms. The primary suite allows access to the enclosed year- round sunroom with expansive views of the water. The home features secondary bedroom with water view, a second full bath, a kitchen with a double wall oven, separate cooktop, a bistro area, and a large pantry. Laundry room. Natural hardwood floors throughout. Insulated attic. Encapsulated crawlspace with new sump pump and dehumidifier. And a welcoming 26' x 6' front porch. Property includes a 2 room and bath cottage. The home is situated on +/- .50 acre. Pier has a 9,000 lb boatlift, swim ladder, water and electric. Beautiful pier lights. This home is a Must-See to truly appreciate all it has to offer. Sellers are offering an assumable FHA mortgage at 5.25% to qualified buyers. Buyer will be responsible to pay sellers the difference between the assumable mortgage amount and the contracted sale price of the home. Sitting on Fishing Creek and runs into the Little Choptank, which runs into the Chesapeake Bay. This home has endless possibilities from Airbnb rental income to a wedding venue; living in the house and renting out the cottage... This property has the potential to create revenue and give you a great return on your investment. Imagine......

1514 Deep Point Rd, Woolford

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

$249,900

PRICE IMPROVEMENT! Charming brick end-unit townhome in Riverview Townhouse Condominiums, ideally located just two blocks from downtown Cambridge! Enjoy distant views of the Choptank River, Cambridge Yacht Basin, and iconic Choptank Lighthouse from this beautifully updated home offering the perfect blend of Colonial charm and modern convenience. Recent improvements include new HVAC (2025), windows (2023), water heater, fresh paint, luxury vinyl plank flooring, updated lighting, ceiling fans, and new granite kitchen countertops. The inviting open floor plan seamlessly connects the living and dining areas, making entertaining effortless. The bright kitchen features double windows, recent appliances, freshly painted cabinetry, granite countertops, and updated lighting. Upstairs, both spacious bedrooms feature private en-suite baths with tub/shower combinations and updated vanities, mirrors, and lighting. A convenient stacked washer and dryer complete the second level. Enjoy maintenance-free living with lawn care and trash service included, plus easy access to all that downtown Cambridge has to offer—restaurants, shops, galleries, the art center, marina, waterfront, and the Ironman finish line are all just a short stroll away. Whether you're looking for a full-time residence, weekend retreat, or investment/Airbnb opportunity, this property offers an exceptional combination of location, updates, water views, and convenience. Come see why you may never want to leave!

2 Beds ⋅ 3 Baths

PRICE IMPROVEMENT! Charming brick end-unit townhome in Riverview Townhouse Condominiums, ideally located just two blocks from downtown Cambridge! Enjoy distant views of the Choptank River, Cambridge Yacht Basin, and iconic Choptank Lighthouse from this beautifully updated home offering the perfect blend of Colonial charm and modern convenience. Recent improvements include new HVAC (2025), windows (2023), water heater, fresh paint, luxury vinyl plank flooring, updated lighting, ceiling fans, and new granite kitchen countertops. The inviting open floor plan seamlessly connects the living and dining areas, making entertaining effortless. The bright kitchen features double windows, recent appliances, freshly painted cabinetry, granite countertops, and updated lighting. Upstairs, both spacious bedrooms feature private en-suite baths with tub/shower combinations and updated vanities, mirrors, and lighting. A convenient stacked washer and dryer complete the second level. Enjoy maintenance-free living with lawn care and trash service included, plus easy access to all that downtown Cambridge has to offer—restaurants, shops, galleries, the art center, marina, waterfront, and the Ironman finish line are all just a short stroll away. Whether you're looking for a full-time residence, weekend retreat, or investment/Airbnb opportunity, this property offers an exceptional combination of location, updates, water views, and convenience. Come see why you may never want to leave!

600-3 Water St, Cambridge

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

How much is your home worth?

How much is your home worth?