easternshoremdfineproperties.com Search Results

$5,995,000

See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. "Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 76+-acre waterfront estate has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8 Beds ⋅ 6 Baths

See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. "Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 76+-acre waterfront estate has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$7,900,000

"Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 114+-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. An adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8 Beds ⋅ 6 Baths

"Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 114+-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. An adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$5,995,000

See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. "Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 76+-acre waterfront estate has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8 Beds ⋅ 6 Baths

See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. "Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 76+-acre waterfront estate has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$1,100,000

Built in 2006 and meticulously maintained, this exceptional home offers 6,553 square feet of living space, including 4,463 square feet above grade and an additional 2,090 square feet in the finished walk-out basement with both interior and exterior access. Inside, a dramatic two-story foyer and soaring family room create an impressive sense of openness, while oversized windows fill the home with abundant natural light. The thoughtfully designed floor plan includes formal living and dining rooms, as well as inviting spaces for everyday living and entertainment. A private first-floor office offers flexibility to serve as a main-level bedroom if desired. Dual staircases provide convenient access to the second level. The gourmet kitchen features beautiful 42-inch cabinetry, Corian countertops, a center island, and a sunny breakfast room with a door leading to the backyard, making indoor-outdoor entertainment effortless. The spacious primary suite is a true retreat, highlighted by a coffered ceiling, a generous walk-in closet, and a luxurious en-suite bath. The second floor offers four bedrooms and three baths. The finished basement expands the living space with a full bathroom and endless possibilities for recreation, entertaining, or multi-generational living. Situated on a private lot backing to open space, the property extends beyond the wrought iron fenced around the gunite pool, into a serene stand of mature pine trees, creating a peaceful and picturesque setting. The professionally landscaped grounds feature lush flower beds with an irrigation system, extensive hardscaping surrounding the gunite pool, patio, and a wraparound porch on the front, catches all the curb appeal you want, paved driveway leading to the side-entry garage. Additional highlights include an epoxy-coated garage floor with an organized wall storage system, professional-grade landscaping, and exceptional pride of ownership throughout. This home shows like a new offering the quality and feel of new construction without the wait. Despite its remarkably quiet and private setting, the home is conveniently located just minutes from shopping, dining, community events, water access, major commuter routes, offering the perfect balance of tranquility and accessibility. So, if you are ready to design your new life style or have a second home, come see this beautiful home.

4 Beds ⋅ 5 Baths

Built in 2006 and meticulously maintained, this exceptional home offers 6,553 square feet of living space, including 4,463 square feet above grade and an additional 2,090 square feet in the finished walk-out basement with both interior and exterior access. Inside, a dramatic two-story foyer and soaring family room create an impressive sense of openness, while oversized windows fill the home with abundant natural light. The thoughtfully designed floor plan includes formal living and dining rooms, as well as inviting spaces for everyday living and entertainment. A private first-floor office offers flexibility to serve as a main-level bedroom if desired. Dual staircases provide convenient access to the second level. The gourmet kitchen features beautiful 42-inch cabinetry, Corian countertops, a center island, and a sunny breakfast room with a door leading to the backyard, making indoor-outdoor entertainment effortless. The spacious primary suite is a true retreat, highlighted by a coffered ceiling, a generous walk-in closet, and a luxurious en-suite bath. The second floor offers four bedrooms and three baths. The finished basement expands the living space with a full bathroom and endless possibilities for recreation, entertaining, or multi-generational living. Situated on a private lot backing to open space, the property extends beyond the wrought iron fenced around the gunite pool, into a serene stand of mature pine trees, creating a peaceful and picturesque setting. The professionally landscaped grounds feature lush flower beds with an irrigation system, extensive hardscaping surrounding the gunite pool, patio, and a wraparound porch on the front, catches all the curb appeal you want, paved driveway leading to the side-entry garage. Additional highlights include an epoxy-coated garage floor with an organized wall storage system, professional-grade landscaping, and exceptional pride of ownership throughout. This home shows like a new offering the quality and feel of new construction without the wait. Despite its remarkably quiet and private setting, the home is conveniently located just minutes from shopping, dining, community events, water access, major commuter routes, offering the perfect balance of tranquility and accessibility. So, if you are ready to design your new life style or have a second home, come see this beautiful home.

13446 Blackberry Ln, Wye Mills

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

$369,000

Welcome to 5116 Ocean Gateway, a thoughtfully updated rancher in Trappe offering Eastern Shore charm, comfortable one-level living, 1.5 acres, and an exceptional detached workshop and four-car garage. Conveniently located along Route 50, the property provides easy access to Easton, Cambridge, Oxford, St. Michaels, shopping, dining, waterfront destinations, and everyday conveniences, with Ocean City approximately one hour away. From the moment you arrive, the property makes a memorable impression with its established perennial gardens, expansive landscape, flagpole, security doors, new windows installed in 2022, and a brand-new roof completed in 2026. A 12-by-24 hobby shed with an upper storage level provides even more room for lawn equipment, seasonal items, projects, or recreational gear. Inside, a brand-new, fully insulated 225-square-foot sunroom completed in 2026 expands the home’s living space and creates a bright, inviting place to relax, entertain, or enjoy views of the surrounding property throughout the year. A new whole-house split system installed in 2026 provides energy-efficient heating and air conditioning in addition to the home’s existing baseboard heat. The renovated kitchen combines style, character, and everyday functionality with new cabinetry, granite countertops, a farmhouse sink, recessed lighting, a large island with a Boos Block butcher-block countertop, built-in pot filler, range hood, and a brand-new 36-inch Cosmo gas range. A mudroom, pantry, and butler’s pantry add valuable storage and help keep the home organized. The updated bathroom offers a spa-inspired retreat with a soaking tub, dual-sink vanity, built-in shelving, and a spacious walk-in shower with a built-in bench. The standout feature of this property is the hand-built 24-by-36 heated workshop, barn, and four-car garage. Designed for vehicle access, equipment, hobbies, and serious project space, the building features handcrafted 10-by-10 Ipe wood carriage doors, a rear 8-by-7 roll-up garage door, concrete flooring, a water hookup, high-intensity lighting, 120- and 230-volt receptacles, and 120/230-volt electrical service supported by a 60-amp subpanel. The generous layout provides space for multiple vehicles, boat or RV storage, woodworking equipment, tools, recreational gear, or a dedicated creative workspace. With major improvements, flexible storage, an updated one-level home, a beautiful new sunroom, and a substantial four-car garage and workshop, this unique Trappe property offers a rare combination of comfort, land, character, and utility. Schedule your private tour and experience everything 5116 Ocean Gateway has to offer.

2 Beds ⋅ 1 Baths

Welcome to 5116 Ocean Gateway, a thoughtfully updated rancher in Trappe offering Eastern Shore charm, comfortable one-level living, 1.5 acres, and an exceptional detached workshop and four-car garage. Conveniently located along Route 50, the property provides easy access to Easton, Cambridge, Oxford, St. Michaels, shopping, dining, waterfront destinations, and everyday conveniences, with Ocean City approximately one hour away. From the moment you arrive, the property makes a memorable impression with its established perennial gardens, expansive landscape, flagpole, security doors, new windows installed in 2022, and a brand-new roof completed in 2026. A 12-by-24 hobby shed with an upper storage level provides even more room for lawn equipment, seasonal items, projects, or recreational gear. Inside, a brand-new, fully insulated 225-square-foot sunroom completed in 2026 expands the home’s living space and creates a bright, inviting place to relax, entertain, or enjoy views of the surrounding property throughout the year. A new whole-house split system installed in 2026 provides energy-efficient heating and air conditioning in addition to the home’s existing baseboard heat. The renovated kitchen combines style, character, and everyday functionality with new cabinetry, granite countertops, a farmhouse sink, recessed lighting, a large island with a Boos Block butcher-block countertop, built-in pot filler, range hood, and a brand-new 36-inch Cosmo gas range. A mudroom, pantry, and butler’s pantry add valuable storage and help keep the home organized. The updated bathroom offers a spa-inspired retreat with a soaking tub, dual-sink vanity, built-in shelving, and a spacious walk-in shower with a built-in bench. The standout feature of this property is the hand-built 24-by-36 heated workshop, barn, and four-car garage. Designed for vehicle access, equipment, hobbies, and serious project space, the building features handcrafted 10-by-10 Ipe wood carriage doors, a rear 8-by-7 roll-up garage door, concrete flooring, a water hookup, high-intensity lighting, 120- and 230-volt receptacles, and 120/230-volt electrical service supported by a 60-amp subpanel. The generous layout provides space for multiple vehicles, boat or RV storage, woodworking equipment, tools, recreational gear, or a dedicated creative workspace. With major improvements, flexible storage, an updated one-level home, a beautiful new sunroom, and a substantial four-car garage and workshop, this unique Trappe property offers a rare combination of comfort, land, character, and utility. Schedule your private tour and experience everything 5116 Ocean Gateway has to offer.

5116 Ocean Gateway, Trappe

Listing courtesy of Keller Williams Flagship. Contact:

$1,795,000

A wonderful opportunity to purchase an amazing one story waterfront home on an expansive 2.5 acre lot with western exposure on Broad Creek. Many upgrades have been done to make this a special home to enjoy your life of relaxation and pure enjoyment on the Eastern Shore of Maryland! Mount Pleasant is a very sought after St Michaels neighborhood with close proximity to the downtown historic area of great restaurants, museums and boutiques but no town taxes! You will love the upgraded gourmet kitchen with granite countertops, large center island, soft close cabinetry, broad water views with Samsung stainless steel appliances where you can make your favorite dishes to enjoy. Besides the kitchen, the large Sunroom is my other favorite room of the home with large windows on three sides for panoramic water views to enjoy nature, sunsets and waterfowl along with great access to the wrap around waterside deck through sliding glass doors. I think you will agree when you see it! You will find a bonus of lovely hardwood floors throughout the home and 2 full upgraded bathrooms as well as a double sided wood burning fireplace for the cooler nights on the Shore and we all know that last winter was colder than most so it was very much enjoyed! The property includes a heated workshop for hobbies as well as 2 other sheds for extra storage should you need it but also a screened waterside Gazebo for entertainment, wraparound deck, partially covered front porch and a deeded private dock on Broad Creek with 3+ MLW with multiple slips, a boat lift and a great place to catch some fresh crabs for dinner! What are you waiting for? This could be the one you have been waiting to come on the market!

3 Beds ⋅ 2 Baths

A wonderful opportunity to purchase an amazing one story waterfront home on an expansive 2.5 acre lot with western exposure on Broad Creek. Many upgrades have been done to make this a special home to enjoy your life of relaxation and pure enjoyment on the Eastern Shore of Maryland! Mount Pleasant is a very sought after St Michaels neighborhood with close proximity to the downtown historic area of great restaurants, museums and boutiques but no town taxes! You will love the upgraded gourmet kitchen with granite countertops, large center island, soft close cabinetry, broad water views with Samsung stainless steel appliances where you can make your favorite dishes to enjoy. Besides the kitchen, the large Sunroom is my other favorite room of the home with large windows on three sides for panoramic water views to enjoy nature, sunsets and waterfowl along with great access to the wrap around waterside deck through sliding glass doors. I think you will agree when you see it! You will find a bonus of lovely hardwood floors throughout the home and 2 full upgraded bathrooms as well as a double sided wood burning fireplace for the cooler nights on the Shore and we all know that last winter was colder than most so it was very much enjoyed! The property includes a heated workshop for hobbies as well as 2 other sheds for extra storage should you need it but also a screened waterside Gazebo for entertainment, wraparound deck, partially covered front porch and a deeded private dock on Broad Creek with 3+ MLW with multiple slips, a boat lift and a great place to catch some fresh crabs for dinner! What are you waiting for? This could be the one you have been waiting to come on the market!

23776 Mount Pleasant Landing, Saint Michaels

Listing courtesy of Shore Living Real Estate. Contact: 4102515291

$370,000

Welcome to 408 Crowberry Circle, where convenience, comfort, and exceptional value come together in one of Easton's most desirable communities. Offering nearly 1,900 square feet of living space, this beautifully maintained end-unit townhome delivers outstanding value with the space and features today's buyers are searching for. Featuring 3 bedrooms, 2.5 bathrooms, a two-car garage, and a versatile bonus room that offers potential for a fourth bedroom, home office, gym, playroom, or guest space, this home provides flexibility for a variety of lifestyles. Inside, you'll find an open and inviting floor plan with luxury vinyl plank flooring throughout the main living areas, creating a warm and cohesive feel. The spacious kitchen is designed for both everyday living and entertaining, complete with granite countertops, stainless steel appliances, abundant cabinetry, a large center island, and direct access to the rear deck. Whether you're hosting family and friends, grilling on summer evenings, or enjoying your morning coffee, the deck provides the perfect extension of your living space while overlooking the added benefit of a side yard unique to this end-unit location. Upstairs, the spacious primary suite offers a large walk-in closet and an upgraded en-suite bathroom featuring a beautifully tiled walk-in shower, creating a private retreat at the end of the day. As an end unit, the home benefits from additional windows, abundant natural light, and more outdoor space than many neighboring properties. The two-car garage offers plenty of room for parking, storage, and recreational gear. Location is one of this home's greatest assets. Situated directly across from the community playground and mailboxes, everyday conveniences are just steps away. You'll also enjoy being minutes from historic downtown Easton, where locally owned restaurants, coffee shops, boutiques, galleries, parks, and year-round events create the vibrant Eastern Shore lifestyle residents love. With easy access to shopping, healthcare, schools, and commuter routes, this location offers the perfect balance of convenience and community. Combining low-maintenance living, modern finishes, flexible space, and an unbeatable location, 408 Crowberry Circle presents an exceptional opportunity to enjoy all that Easton has to offer.

3 Beds ⋅ 3 Baths

Welcome to 408 Crowberry Circle, where convenience, comfort, and exceptional value come together in one of Easton's most desirable communities. Offering nearly 1,900 square feet of living space, this beautifully maintained end-unit townhome delivers outstanding value with the space and features today's buyers are searching for. Featuring 3 bedrooms, 2.5 bathrooms, a two-car garage, and a versatile bonus room that offers potential for a fourth bedroom, home office, gym, playroom, or guest space, this home provides flexibility for a variety of lifestyles. Inside, you'll find an open and inviting floor plan with luxury vinyl plank flooring throughout the main living areas, creating a warm and cohesive feel. The spacious kitchen is designed for both everyday living and entertaining, complete with granite countertops, stainless steel appliances, abundant cabinetry, a large center island, and direct access to the rear deck. Whether you're hosting family and friends, grilling on summer evenings, or enjoying your morning coffee, the deck provides the perfect extension of your living space while overlooking the added benefit of a side yard unique to this end-unit location. Upstairs, the spacious primary suite offers a large walk-in closet and an upgraded en-suite bathroom featuring a beautifully tiled walk-in shower, creating a private retreat at the end of the day. As an end unit, the home benefits from additional windows, abundant natural light, and more outdoor space than many neighboring properties. The two-car garage offers plenty of room for parking, storage, and recreational gear. Location is one of this home's greatest assets. Situated directly across from the community playground and mailboxes, everyday conveniences are just steps away. You'll also enjoy being minutes from historic downtown Easton, where locally owned restaurants, coffee shops, boutiques, galleries, parks, and year-round events create the vibrant Eastern Shore lifestyle residents love. With easy access to shopping, healthcare, schools, and commuter routes, this location offers the perfect balance of convenience and community. Combining low-maintenance living, modern finishes, flexible space, and an unbeatable location, 408 Crowberry Circle presents an exceptional opportunity to enjoy all that Easton has to offer.

408 Crowberry Cir, Easton

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

$695,000

Discover the perfect blend of privacy in this spacious three bedroom, 3 full bath , Colonial located in the sought-after High Banks community. Set on over 4 acres in the water-privileged section with access to the Choptank River, this home offers a bright open floor plan, durable LVP flooring, wood stove insert with marble hearth, crown molding, and a nice open kitchen with a center island ideal for everyday living and entertaining. The second floor offers a nice loft / bonus area with fireplace, spacious owners suite with WIC and attached bath, plus a walk-in attic with potential for additional living space. Step outside to your own private retreat featuring a fenced rear yard, in-ground swimming pool, full pool bath with exterior access, and an expansive composite deck with vinyl railing—perfect for summer gatherings. Additional highlights include a new roof in 2025, new water heater April 2026, Polaris pool pimp replaced Fall 2025. attached 2-car garage with workbench. New shower in primary bathroom 2025, Chesapeake Crawl space Nov 2024,. Enjoy peaceful country living while remaining close to downtown amenities. Less than a mile to Kingston Landing – a public boat ramp for easy access to the water.

3 Beds ⋅ 3 Baths

Discover the perfect blend of privacy in this spacious three bedroom, 3 full bath , Colonial located in the sought-after High Banks community. Set on over 4 acres in the water-privileged section with access to the Choptank River, this home offers a bright open floor plan, durable LVP flooring, wood stove insert with marble hearth, crown molding, and a nice open kitchen with a center island ideal for everyday living and entertaining. The second floor offers a nice loft / bonus area with fireplace, spacious owners suite with WIC and attached bath, plus a walk-in attic with potential for additional living space. Step outside to your own private retreat featuring a fenced rear yard, in-ground swimming pool, full pool bath with exterior access, and an expansive composite deck with vinyl railing—perfect for summer gatherings. Additional highlights include a new roof in 2025, new water heater April 2026, Polaris pool pimp replaced Fall 2025. attached 2-car garage with workbench. New shower in primary bathroom 2025, Chesapeake Crawl space Nov 2024,. Enjoy peaceful country living while remaining close to downtown amenities. Less than a mile to Kingston Landing – a public boat ramp for easy access to the water.

32930 Oyster Bank Ter, Easton

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

$99,000

Come see this charming home located in the sought after 55+ community of Hyde Park a Sun Community in Easton. This home offers lots of updates throughout. Major improvements: new roof (2017), Heat pump (2023) A/C unit (2017) Beautiful Laminate flooring (2017) New deck and sliding door (2017) Some new vinyl windows (2022) New Shed (2017), All newer appliances within 5 yrs to include washer and dryer. Additional upgrades include: Resurfaced Driveway (2020) Upgraded interior lighting (2017) Repainted interior & exterior (2018) New exterior shutters (2022) Upgraded landscaping & exterior lighting (2017). You will find the location in the park unbeatable as it backs up to beautiful trees and views of open farm field beyond! A large rear deck offering a private, functional, and inviting retreat for relaxing and entertainment or just enjoying your morning coffee! A wonderful sunroom offers added living space and with a little heater can be used year round. The ample kitchen boasts plenty of cabinets and work space along with a breakfast bar. Some community amenities include: Club House with exercise room; inground pool; covered pavilion; gazebo; disc golf course; dog park; walking paths; fishing pond and rv & boat storage. Just minutes to local shops, stores, restaurants and all Easton has to offer!

2 Beds ⋅ 1 Baths

Come see this charming home located in the sought after 55+ community of Hyde Park a Sun Community in Easton. This home offers lots of updates throughout. Major improvements: new roof (2017), Heat pump (2023) A/C unit (2017) Beautiful Laminate flooring (2017) New deck and sliding door (2017) Some new vinyl windows (2022) New Shed (2017), All newer appliances within 5 yrs to include washer and dryer. Additional upgrades include: Resurfaced Driveway (2020) Upgraded interior lighting (2017) Repainted interior & exterior (2018) New exterior shutters (2022) Upgraded landscaping & exterior lighting (2017). You will find the location in the park unbeatable as it backs up to beautiful trees and views of open farm field beyond! A large rear deck offering a private, functional, and inviting retreat for relaxing and entertainment or just enjoying your morning coffee! A wonderful sunroom offers added living space and with a little heater can be used year round. The ample kitchen boasts plenty of cabinets and work space along with a breakfast bar. Some community amenities include: Club House with exercise room; inground pool; covered pavilion; gazebo; disc golf course; dog park; walking paths; fishing pond and rv & boat storage. Just minutes to local shops, stores, restaurants and all Easton has to offer!

47 Park Ln, Easton

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

$598,000

Rio Vista Community – No Town Taxes! Enjoy life in the desirable Rio Vista community, featuring exclusive resident access to a waterfront park on the Miles River. Located just outside historic St. Michaels, this home offers exceptional convenience with a grocery store, hardware store, restaurants, beauty salon, Pilates studio, YMCA, and garden center all just minutes away. This solid ranch-style home is currently tenant-occupied; a minimum of 24 hours' notice is required for showings. Home Features: Hardwood floors throughout Wood cabinetry kitchen with quartz countertops Bright tiled sunroom with a cozy wood stove Attached 2-car garage Comfortable single-level living Whether you're looking for a weekend retreat or a year-round residence, this property offers both comfort and convenience in a sought-after location. Priced below appraised value—an outstanding opportunity!

3 Beds ⋅ 2 Baths

Rio Vista Community – No Town Taxes! Enjoy life in the desirable Rio Vista community, featuring exclusive resident access to a waterfront park on the Miles River. Located just outside historic St. Michaels, this home offers exceptional convenience with a grocery store, hardware store, restaurants, beauty salon, Pilates studio, YMCA, and garden center all just minutes away. This solid ranch-style home is currently tenant-occupied; a minimum of 24 hours' notice is required for showings. Home Features: Hardwood floors throughout Wood cabinetry kitchen with quartz countertops Bright tiled sunroom with a cozy wood stove Attached 2-car garage Comfortable single-level living Whether you're looking for a weekend retreat or a year-round residence, this property offers both comfort and convenience in a sought-after location. Priced below appraised value—an outstanding opportunity!

204 Lincoln, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283

$6,250,000

Set on 31 private acres along the peaceful waters of Hunting Creek, this exceptional Eastern Shore estate combines timeless architecture with modern sophistication. With over 1,000 feet of waterfront and approximately 6 feet of mean low water, the property offers deep-water access, stunning views, and an unmatched sense of privacy. The five-bedroom, five-and-a-half-bath residence has been completely renovated from top to bottom, showcasing impeccable finishes, custom millwork, and thoughtfully designed spaces throughout. Sunlight pours through large windows that frame panoramic views of the creek and surrounding landscape. The home features two luxurious primary suites, each offering a private retreat with refined finishes, spa-inspired baths, and generous closets. Two additional bedrooms share a beautifully designed ensuite bathroom, while a first-floor bunk room with its own bath provides the perfect space for guests. Outside, the saltwater pool overlooks the water, surrounded by manicured lawns and mature trees that extend to the shoreline. A long, tree-lined driveway creates an impressive approach to the home, setting the tone for the peaceful retreat that awaits. Located just minutes by car to Easton and St. Michaels—and even closer by boat—this Hunting Creek estate captures the very best of the Chesapeake Bay lifestyle: elegance, tranquility, and effortless connection to the water.

5 Beds ⋅ 6 Baths

Set on 31 private acres along the peaceful waters of Hunting Creek, this exceptional Eastern Shore estate combines timeless architecture with modern sophistication. With over 1,000 feet of waterfront and approximately 6 feet of mean low water, the property offers deep-water access, stunning views, and an unmatched sense of privacy. The five-bedroom, five-and-a-half-bath residence has been completely renovated from top to bottom, showcasing impeccable finishes, custom millwork, and thoughtfully designed spaces throughout. Sunlight pours through large windows that frame panoramic views of the creek and surrounding landscape. The home features two luxurious primary suites, each offering a private retreat with refined finishes, spa-inspired baths, and generous closets. Two additional bedrooms share a beautifully designed ensuite bathroom, while a first-floor bunk room with its own bath provides the perfect space for guests. Outside, the saltwater pool overlooks the water, surrounded by manicured lawns and mature trees that extend to the shoreline. A long, tree-lined driveway creates an impressive approach to the home, setting the tone for the peaceful retreat that awaits. Located just minutes by car to Easton and St. Michaels—and even closer by boat—this Hunting Creek estate captures the very best of the Chesapeake Bay lifestyle: elegance, tranquility, and effortless connection to the water.

9170 Hunting Creek Ln, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$2,395,000

Due to personal reasons, BUYER had to withdraw offer--Inspections were "better than good" according to inspector. LOCATION, CHARM, and beautifully RENOVATED!!!Set on 2.32 glorious acres overlooking Dixon Creek, this beautifully and lovingly maintained 1915 residence offers timeless character, refined comfort, and exceptional waterfront living. Original hardwood floors run throughout much of the home, while expansive windows bathe the traditional floor plan in natural light and frame expansive water views from nearly every room. The main level features gracious formal living and dining rooms, a gourmet kitchen with a beautiful center island and top-tier stainless appliances, and a welcoming family room with wood-burning fireplace. Custom built-ins are thoughtfully integrated throughout the home, reflecting quality craftsmanship and attention to detail. Upstairs, the waterside primary suite offers a fireplace, dual walk-in closets and a luxurious ensuite bath with soaking tub and glass-enclosed shower. Two additional guest bedrooms include one with an ensuite bath and another with access to the hall bath. The third level provides a small loft style BR /flexible bonus room, ideal for an office or studio. Outdoor living is equally inviting, with a waterside screened porch, a poolside screened patio with wet bar, and an additional open deck off the dining room—perfect for enjoying the tranquil setting. The beautifully landscaped grounds feature mature trees, lush plantings, and extensive hardscaping, anchored by a gunite pool with expansive deck and surrounding gardens. Additional structures include a charming former icehouse (currently used as a storage shed) and a larger outbuilding once used as tenant quarters. An attached 2-car garage and a full encapsulated basement offer excellent functionality and versatility. With 280 feet of natural shoreline, a private pier with two slips, boat lift, and 3.5–4' MLW, this property captures the essence of Eastern Shore waterfront living. *Roof- 2011, new siding, new boiler, renovated kitchen and baths, redecked pier. -Septic replaced in 2020 and is for 4 bedrooms-owners have plans for proposed first floor primary suite where existing south side porch currently is.

4 Beds ⋅ 4 Baths

Due to personal reasons, BUYER had to withdraw offer--Inspections were "better than good" according to inspector. LOCATION, CHARM, and beautifully RENOVATED!!!Set on 2.32 glorious acres overlooking Dixon Creek, this beautifully and lovingly maintained 1915 residence offers timeless character, refined comfort, and exceptional waterfront living. Original hardwood floors run throughout much of the home, while expansive windows bathe the traditional floor plan in natural light and frame expansive water views from nearly every room. The main level features gracious formal living and dining rooms, a gourmet kitchen with a beautiful center island and top-tier stainless appliances, and a welcoming family room with wood-burning fireplace. Custom built-ins are thoughtfully integrated throughout the home, reflecting quality craftsmanship and attention to detail. Upstairs, the waterside primary suite offers a fireplace, dual walk-in closets and a luxurious ensuite bath with soaking tub and glass-enclosed shower. Two additional guest bedrooms include one with an ensuite bath and another with access to the hall bath. The third level provides a small loft style BR /flexible bonus room, ideal for an office or studio. Outdoor living is equally inviting, with a waterside screened porch, a poolside screened patio with wet bar, and an additional open deck off the dining room—perfect for enjoying the tranquil setting. The beautifully landscaped grounds feature mature trees, lush plantings, and extensive hardscaping, anchored by a gunite pool with expansive deck and surrounding gardens. Additional structures include a charming former icehouse (currently used as a storage shed) and a larger outbuilding once used as tenant quarters. An attached 2-car garage and a full encapsulated basement offer excellent functionality and versatility. With 280 feet of natural shoreline, a private pier with two slips, boat lift, and 3.5–4' MLW, this property captures the essence of Eastern Shore waterfront living. *Roof- 2011, new siding, new boiler, renovated kitchen and baths, redecked pier. -Septic replaced in 2020 and is for 4 bedrooms-owners have plans for proposed first floor primary suite where existing south side porch currently is.

8075 Leehaven Rd, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$1,195,000

Incredible opportunity to own a circa 1875 home in Oxford's Historic District that has been renovated with a separate 2 bedroom apartment with views of Town Creek. Formerly a Bed and Breakfast, it features 2 first floor bedrooms with 1 and 1/2 baths and 3 second floor bedrooms each with its own full bath. Entire exterior has been newly painted and most of the windows have been replaced. A lovely side garden with a fountain, front porch close to Town Park, and a one and one half car garage with room for a workshop compliment the home. The bright, newly renovated kitchen is the center of the house featuring an alcove with a large kitchen table. It overlooks the side garden. Owner prefers 24 hour notice if possible

5 Beds ⋅ 6 Baths

Incredible opportunity to own a circa 1875 home in Oxford's Historic District that has been renovated with a separate 2 bedroom apartment with views of Town Creek. Formerly a Bed and Breakfast, it features 2 first floor bedrooms with 1 and 1/2 baths and 3 second floor bedrooms each with its own full bath. Entire exterior has been newly painted and most of the windows have been replaced. A lovely side garden with a fountain, front porch close to Town Park, and a one and one half car garage with room for a workshop compliment the home. The bright, newly renovated kitchen is the center of the house featuring an alcove with a large kitchen table. It overlooks the side garden. Owner prefers 24 hour notice if possible

110 N Morris St, Oxford

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

$1,195,000

Incredible opportunity to own a circa 1875 home in Oxford's Historic District that has been renovated with a separate 2 bedroom apartment with views of Town Creek. Formerly a Bed and Breakfast, it features 2 first floor bedrooms with 1 and 1/2 baths and 3 second floor bedrooms each with its own full bath. Entire exterior has been newly painted and most of the windows have been replaced. A lovely side garden with a fountain, front porch close to Town Park, and a one and one half car garage with room for a workshop compliment the home. The bright, newly renovated kitchen is the center of the house featuring an alcove with a large kitchen table. It overlooks the side garden. Owner prefers weekend showings. If weekday is only possibility, please allow 24 hours. Thank you

110 N Morris St, Oxford

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

$7,900,000

"Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 114+-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. The adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8 Beds ⋅ 6 Baths

"Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 114+-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. The adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$845,000

Renovated waterfront living with room for your fleet! Extensively renovated Cape Cod on Tilghman Island offering exceptional boating access and refined coastal living. This beautifully reimagined 3 BR, 2 BA home features 1,314 sq ft of thoughtfully designed space including two full kitchens with high-end finishes, providing outstanding flexibility for guests or extended living. Bright, upscale interiors blend modern comfort with classic Eastern Shore charm, complemented by a distinctive Standing Seam metal roof and owned solar energy system. Situated along protected waterfront with long water views and four boat slips, offering rare boating convenience and potential income opportunity. A turnkey coastal retreat ideal for full-time living weekend escape.

3 Beds ⋅ 2 Baths

Renovated waterfront living with room for your fleet! Extensively renovated Cape Cod on Tilghman Island offering exceptional boating access and refined coastal living. This beautifully reimagined 3 BR, 2 BA home features 1,314 sq ft of thoughtfully designed space including two full kitchens with high-end finishes, providing outstanding flexibility for guests or extended living. Bright, upscale interiors blend modern comfort with classic Eastern Shore charm, complemented by a distinctive Standing Seam metal roof and owned solar energy system. Situated along protected waterfront with long water views and four boat slips, offering rare boating convenience and potential income opportunity. A turnkey coastal retreat ideal for full-time living weekend escape.

21560 Chicken Point Rd, Tilghman

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

$599,000

Currently offered as a large open area in the center with 2 handicap rest rooms, and a large waiting area with 8 private offices on the exterior perimeter. All utilities are metered separately. In move in condition with tile and carpet. Owner will also consider a lease. Plenty of parking. Was previously a physicians office with a large open bullpen in the center. No stairs to access. Plans available. Sale will include prorate share of CAM. Located in Easton's prime medical community with easy Route 50 access.

508 Idlewild Ave Unit #3, Easton

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

$5,000,000

Now offered at an improved price of $5,000,000. Excellent opportunity to own your own private Eastern Shore estate in Royal Oak. Anderby Hall, part of an original 1680 land grant, spans a breathtaking 12+/- acre parcel featuring 3,260’+/- of rip-rapped shoreline. This exceptional property includes a tidal pond, a private cove, and an exclusive island peninsula accessed by bridge. Pass through the gated driveway to discover the main residence: a 3,000+/- sq. ft. Colonial showcasing a great room with a fireplace, charming old pine floors, hand-hewn ceiling beams, and a granite island kitchen. The luxury primary suite features his-and-her closets alongside a second-floor office/den. Nearly every room frames gorgeous, unobstructed views of Irish Creek. Outside, brick walkways lead to a spectacular waterside pool. Boaters will love the private dock offering 5' MLW, located just minutes from the Choptank River. Additional amenities include a 2,600 sq. ft. guest house, tennis courts (easily convertible to pickleball) with a gazebo, a 30x50 detached 3-car garage, an additional 1-car garage with a workshop, new well, and a service shed. Complete with a licensed shoreline and abundant local wildlife (geese, ducks, deer, and turkey), this estate is convenient to Easton and St. Michaels. Experience an unmatched lifestyle of luxury, privacy, and waterfront beauty at an incredible new value.

3 Beds ⋅ 4 Baths

Now offered at an improved price of $5,000,000. Excellent opportunity to own your own private Eastern Shore estate in Royal Oak. Anderby Hall, part of an original 1680 land grant, spans a breathtaking 12+/- acre parcel featuring 3,260’+/- of rip-rapped shoreline. This exceptional property includes a tidal pond, a private cove, and an exclusive island peninsula accessed by bridge. Pass through the gated driveway to discover the main residence: a 3,000+/- sq. ft. Colonial showcasing a great room with a fireplace, charming old pine floors, hand-hewn ceiling beams, and a granite island kitchen. The luxury primary suite features his-and-her closets alongside a second-floor office/den. Nearly every room frames gorgeous, unobstructed views of Irish Creek. Outside, brick walkways lead to a spectacular waterside pool. Boaters will love the private dock offering 5' MLW, located just minutes from the Choptank River. Additional amenities include a 2,600 sq. ft. guest house, tennis courts (easily convertible to pickleball) with a gazebo, a 30x50 detached 3-car garage, an additional 1-car garage with a workshop, new well, and a service shed. Complete with a licensed shoreline and abundant local wildlife (geese, ducks, deer, and turkey), this estate is convenient to Easton and St. Michaels. Experience an unmatched lifestyle of luxury, privacy, and waterfront beauty at an incredible new value.

5499 Anderby Hall Rd, Royal Oak

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

$659,000

The one-of-a-kind Ryan model is set to be the largest one-story home constructed on Sandy Lane, brought to life by Developer Sandy Lane, LLC and renowned local builders Stansbury and Sons. Like all ten homes in this thoughtfully designed new downtown Easton community, the Ryan will be a custom, stick-built residence backed by a one-year builder’s warranty and outfitted with brand-new appliances and systems—allowing homeowners to enjoy their new space without the constant burden of "old house" maintenance. The Ryan's convenient single-level layout includes three bedrooms, two full baths, and a spacious living room with vaulted ceilings that flows seamlessly into the dining area and a beautifully appointed kitchen. A cook's dream, the kitchen features custom cabinetry, including a large pantry cabinet, solid surface countertops, and stainless-steel appliances. The luxurious primary suite offers a private bath with a tiled shower, double sink vanity and a generous walk-in closet. The two additional bedrooms on the opposite side of the floorplan share a stylish hall bath with tub/shower. There is also a dedicated laundry area—strategically placed between the kitchen, primary suite and garage entrance—which completes the interior. Outside, the home boasts a one-car attached garage with an electric car charger, a concrete driveway with parking for two, custom front foundation landscaping, a fully sodded yard, and a rear patio. Sandy Lane homes are built with premium features such as encapsulated, climate-controlled crawl spaces suitable for storage, superior framing and finish work, certified IECC Energy Efficient insulation (R-49 ceiling, R-21 walls), luxury vinyl flooring throughout, ample closet space, and multiple contemporary ceiling fans and fixtures. The Ryan’s flexible design makes it ideal for retirees, remote workers, singles and families alike. All infrastructure costs—including surveys, permits, site work, utilities, and street improvements—have been prepaid by the developer, eliminating typical new construction extended yearly front foot fees for buyers. Located off N Washington Street in Easton, Sandy Lane offers easy access to downtown amenities such as Easton Utilities (electric, water, sewer, cable, and high-speed internet), weekly trash and recycling pickup, and a wealth of recreational options including parks, sports fields, trails, playgrounds, tennis and pickleball courts, a community pool, and a dog park. Easton and Talbot County provide abundant waterfront access, fire and police services, medical facilities, cultural attractions such as the Avalon Theater, The Academy Art Museum, and Maritime Museum, premium shopping, and some of the best dining on the East Coast. The community is subject to Covenants and Restrictions but carries no HOA or associated fees. Developer: Sandy Lane, LLC (MHBR 9512). Builder: Stansbury and Sons Home Improvement Inc. (MHBR 8351). Builder Contract required.

3 Beds ⋅ 2 Baths

The one-of-a-kind Ryan model is set to be the largest one-story home constructed on Sandy Lane, brought to life by Developer Sandy Lane, LLC and renowned local builders Stansbury and Sons. Like all ten homes in this thoughtfully designed new downtown Easton community, the Ryan will be a custom, stick-built residence backed by a one-year builder’s warranty and outfitted with brand-new appliances and systems—allowing homeowners to enjoy their new space without the constant burden of "old house" maintenance. The Ryan's convenient single-level layout includes three bedrooms, two full baths, and a spacious living room with vaulted ceilings that flows seamlessly into the dining area and a beautifully appointed kitchen. A cook's dream, the kitchen features custom cabinetry, including a large pantry cabinet, solid surface countertops, and stainless-steel appliances. The luxurious primary suite offers a private bath with a tiled shower, double sink vanity and a generous walk-in closet. The two additional bedrooms on the opposite side of the floorplan share a stylish hall bath with tub/shower. There is also a dedicated laundry area—strategically placed between the kitchen, primary suite and garage entrance—which completes the interior. Outside, the home boasts a one-car attached garage with an electric car charger, a concrete driveway with parking for two, custom front foundation landscaping, a fully sodded yard, and a rear patio. Sandy Lane homes are built with premium features such as encapsulated, climate-controlled crawl spaces suitable for storage, superior framing and finish work, certified IECC Energy Efficient insulation (R-49 ceiling, R-21 walls), luxury vinyl flooring throughout, ample closet space, and multiple contemporary ceiling fans and fixtures. The Ryan’s flexible design makes it ideal for retirees, remote workers, singles and families alike. All infrastructure costs—including surveys, permits, site work, utilities, and street improvements—have been prepaid by the developer, eliminating typical new construction extended yearly front foot fees for buyers. Located off N Washington Street in Easton, Sandy Lane offers easy access to downtown amenities such as Easton Utilities (electric, water, sewer, cable, and high-speed internet), weekly trash and recycling pickup, and a wealth of recreational options including parks, sports fields, trails, playgrounds, tennis and pickleball courts, a community pool, and a dog park. Easton and Talbot County provide abundant waterfront access, fire and police services, medical facilities, cultural attractions such as the Avalon Theater, The Academy Art Museum, and Maritime Museum, premium shopping, and some of the best dining on the East Coast. The community is subject to Covenants and Restrictions but carries no HOA or associated fees. Developer: Sandy Lane, LLC (MHBR 9512). Builder: Stansbury and Sons Home Improvement Inc. (MHBR 8351). Builder Contract required.

13 Sandy Ln, Easton

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

$745,000

Back on market due to BUYER not being able to sell their house! Clean inspections so READY for YOU! This beautifully sited end-unit townhouse has serene field views, and offers 2,433 sq. ft. of elegant living with 4 bedrooms, 3 full baths, and 1 half bath. Designed with an open concept, the living room, dining room, and kitchen flow seamlessly together, creating a warm and inviting space for entertaining or everyday living. Soaring two-story ceilings, skylights, and expansive windows flood the home with natural light, while a gas-burning fireplace is the focal point of this inviting space. The main-level primary suite serves as a private retreat with an ensuite bath, complemented by two walk-in closets. A cozy den and convenient powder room complete the main level. An upper-level loft overlook adds architectural charm and provides additional space for relaxation. Upstairs, one guest bedroom enjoys its own ensuite bath, and two additional bedrooms share a connecting full bath. Outdoors, a beautifully landscaped backyard framed by mature trees provides a tranquil setting, while the attached 2-car garage offers convenience. Cooke’s Hope residents enjoy an unmatched lifestyle with ponds, tennis courts, walking trails, a dog park, fitness center, picnic pavilion, and a community dock—making this one of Easton’s most desirable communities.

4 Beds ⋅ 4 Baths

Back on market due to BUYER not being able to sell their house! Clean inspections so READY for YOU! This beautifully sited end-unit townhouse has serene field views, and offers 2,433 sq. ft. of elegant living with 4 bedrooms, 3 full baths, and 1 half bath. Designed with an open concept, the living room, dining room, and kitchen flow seamlessly together, creating a warm and inviting space for entertaining or everyday living. Soaring two-story ceilings, skylights, and expansive windows flood the home with natural light, while a gas-burning fireplace is the focal point of this inviting space. The main-level primary suite serves as a private retreat with an ensuite bath, complemented by two walk-in closets. A cozy den and convenient powder room complete the main level. An upper-level loft overlook adds architectural charm and provides additional space for relaxation. Upstairs, one guest bedroom enjoys its own ensuite bath, and two additional bedrooms share a connecting full bath. Outdoors, a beautifully landscaped backyard framed by mature trees provides a tranquil setting, while the attached 2-car garage offers convenience. Cooke’s Hope residents enjoy an unmatched lifestyle with ponds, tennis courts, walking trails, a dog park, fitness center, picnic pavilion, and a community dock—making this one of Easton’s most desirable communities.

28933 Jasper Ln, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$6,800,000

Welcome to this extraordinary waterfront estate, gracefully sited on 6.92 lush, landscaped acres with sweeping views of Leadenham Creek. Designed by architect Alan Meyers, constructed by Ilex Construction, and masterfully styled by interior designer Skip Sroka, this 10,000+/-sq. ft. residence is a showcase of timeless craftsmanship and elevated design. The custom brick exterior is crowned by a new cedar shake roof with copper caps and bands, creating a refined profile that blends seamlessly into the natural surroundings. Double mahogany doors with full-view, artistically designed leaded glass open to a luminous foyer with immediate, breathtaking views of the water. Inside, riff-sawn red oak floors flow through expansive formal and informal living areas. Vaulted ceilings add architectural drama, while curated lighting provides warmth and sophistication throughout. The main level features formal living and dining rooms, a stunning gourmet kitchen, and multiple spaces designed for both relaxation and entertaining. The kitchen is a chef’s dream—equipped with top-tier appliances, a large center island, sitting area with fireplace, and an eat-in dining space. Just off the kitchen, a beautifully crafted screened porch with an octagonal ceiling offers a peaceful, year-round retreat. A walk-in pantry and custom-designed bar enhance both function and hospitality. Also on the main level is a striking private office wrapped in Anigre wood paneling, featuring custom built-ins and a circular backlit ceiling. A separate guest wing includes a spacious family/recreation room with spectacular river views and two guest suites with ensuite baths. The primary suite enjoys its own private wing, with serene water views, a cozy sitting area and fireplace, dual walk-in closets, and an elegant dressing hall. The luxurious, spa-inspired bath includes a soaking tub and glass-enclosed shower, creating a true sanctuary of comfort and privacy. Upstairs, dual wings on opposite sides of the home offer two additional guest suites with ensuite baths, a bonus/music room, and a dedicated fitness room. Five fireplaces handcrafted by Collecio Brothers Stone Masons bring warmth and timeless character throughout the home. Modern systems include geothermal heating and cooling, a new Honeywell HVAC control system, Vantage lighting automation, a fully encapsulated crawlspace, and a Generac generator. In addition to the oversized 3+ car attached garage, a separate detached two-bay garage offers equipment storage, a workshop, and a half bath. Outdoors, the estate is designed for both grand entertaining and quiet waterfront living. Features include an extended waterside patio, beautiful pool house with a fully equipped outdoor kitchen, two dressing rooms, an outdoor shower, and an in-ground pool with heated spa. Over 1,000 feet of riprapped shoreline and a 210-foot private dock with two slips, a floating dock, and 7-foot MLW offer direct access to the Chesapeake Bay. This remarkable estate was built for luxurious living, effortless entertaining, and a deep connection to the natural beauty of Maryland’s Eastern Shore. *Current taxes are based on homestead credit.

5 Beds ⋅ 6 Baths

Welcome to this extraordinary waterfront estate, gracefully sited on 6.92 lush, landscaped acres with sweeping views of Leadenham Creek. Designed by architect Alan Meyers, constructed by Ilex Construction, and masterfully styled by interior designer Skip Sroka, this 10,000+/-sq. ft. residence is a showcase of timeless craftsmanship and elevated design. The custom brick exterior is crowned by a new cedar shake roof with copper caps and bands, creating a refined profile that blends seamlessly into the natural surroundings. Double mahogany doors with full-view, artistically designed leaded glass open to a luminous foyer with immediate, breathtaking views of the water. Inside, riff-sawn red oak floors flow through expansive formal and informal living areas. Vaulted ceilings add architectural drama, while curated lighting provides warmth and sophistication throughout. The main level features formal living and dining rooms, a stunning gourmet kitchen, and multiple spaces designed for both relaxation and entertaining. The kitchen is a chef’s dream—equipped with top-tier appliances, a large center island, sitting area with fireplace, and an eat-in dining space. Just off the kitchen, a beautifully crafted screened porch with an octagonal ceiling offers a peaceful, year-round retreat. A walk-in pantry and custom-designed bar enhance both function and hospitality. Also on the main level is a striking private office wrapped in Anigre wood paneling, featuring custom built-ins and a circular backlit ceiling. A separate guest wing includes a spacious family/recreation room with spectacular river views and two guest suites with ensuite baths. The primary suite enjoys its own private wing, with serene water views, a cozy sitting area and fireplace, dual walk-in closets, and an elegant dressing hall. The luxurious, spa-inspired bath includes a soaking tub and glass-enclosed shower, creating a true sanctuary of comfort and privacy. Upstairs, dual wings on opposite sides of the home offer two additional guest suites with ensuite baths, a bonus/music room, and a dedicated fitness room. Five fireplaces handcrafted by Collecio Brothers Stone Masons bring warmth and timeless character throughout the home. Modern systems include geothermal heating and cooling, a new Honeywell HVAC control system, Vantage lighting automation, a fully encapsulated crawlspace, and a Generac generator. In addition to the oversized 3+ car attached garage, a separate detached two-bay garage offers equipment storage, a workshop, and a half bath. Outdoors, the estate is designed for both grand entertaining and quiet waterfront living. Features include an extended waterside patio, beautiful pool house with a fully equipped outdoor kitchen, two dressing rooms, an outdoor shower, and an in-ground pool with heated spa. Over 1,000 feet of riprapped shoreline and a 210-foot private dock with two slips, a floating dock, and 7-foot MLW offer direct access to the Chesapeake Bay. This remarkable estate was built for luxurious living, effortless entertaining, and a deep connection to the natural beauty of Maryland’s Eastern Shore. *Current taxes are based on homestead credit.

7090 Cooper Point Rd, Bozman

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344