Crystalscotthomes.com Search Results

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

4 Beds ⋅ 5 Baths

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

24679 Deep Neck Rd, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

$3,995,000

Irish Tides offers a quintessential Eastern Shore retreat with luxury and style. This beautifully crafted 4-bedroom, 5.5-bath main house provides captivating views of the Miles River from almost every room. The main level has been enhanced with a new HVAC system and ductwork, ensuring comfort and efficiency throughout. Exquisite crown moldings, hardwood floors, and custom built-ins add an inviting elegance. Enjoy formal living and dining areas, chef’s kitchen with an island, quartz countertops, and a scenic waterside dining nook for informal meals. The family room, with its soaring cathedral ceilings and gas fireplace, flows through a light-filled hallway with cozy seating, offering direct views of the river. New roof installed in 2026. The main-level primary suite features a cathedral ceiling, built-ins, and a private patio, while its spa-like en-suite includes abundant natural light, a jetted soaking tub, marble accents, and two generous walk-in closets. The home also features a newly encapsulated basement and crawlspace, ensuring a well- maintained environment year-round. The professionally landscaped grounds set the stage for a well-equipped pool house complete with a guest room, kitchenette, sitting area, and bathroom. The outdoor space also boasts an in-ground pool with a spacious patio, outdoor shower, and grill area. A private pier with a boat lift offers approximately 4' +/- MLW, a 300' +/- shoreline, and a private beach. For added convenience, the main house includes attic storage and a storage shed, while the 3-car detached garage features a bonus room—perfect for an office or rec room—with kitchenette. All of this is just a short drive from Easton’s dining, shopping, and airport access.

4 Beds ⋅ 6 Baths

Irish Tides offers a quintessential Eastern Shore retreat with luxury and style. This beautifully crafted 4-bedroom, 5.5-bath main house provides captivating views of the Miles River from almost every room. The main level has been enhanced with a new HVAC system and ductwork, ensuring comfort and efficiency throughout. Exquisite crown moldings, hardwood floors, and custom built-ins add an inviting elegance. Enjoy formal living and dining areas, chef’s kitchen with an island, quartz countertops, and a scenic waterside dining nook for informal meals. The family room, with its soaring cathedral ceilings and gas fireplace, flows through a light-filled hallway with cozy seating, offering direct views of the river. New roof installed in 2026. The main-level primary suite features a cathedral ceiling, built-ins, and a private patio, while its spa-like en-suite includes abundant natural light, a jetted soaking tub, marble accents, and two generous walk-in closets. The home also features a newly encapsulated basement and crawlspace, ensuring a well- maintained environment year-round. The professionally landscaped grounds set the stage for a well-equipped pool house complete with a guest room, kitchenette, sitting area, and bathroom. The outdoor space also boasts an in-ground pool with a spacious patio, outdoor shower, and grill area. A private pier with a boat lift offers approximately 4' +/- MLW, a 300' +/- shoreline, and a private beach. For added convenience, the main house includes attic storage and a storage shed, while the 3-car detached garage features a bonus room—perfect for an office or rec room—with kitchenette. All of this is just a short drive from Easton’s dining, shopping, and airport access.

27029 Miles River Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$3,249,000

Island Creek Estate — rare total privacy, deep water dockage, meaningful architecture, and superb build quality all intersect at this remarkable, truly one-of-a-kind waterfront offering. Set on approximately 6 acres of park-like grounds with 500± feet of shoreline and 6’± MLW, the property offers exceptional water access along the peaceful expanse of Island Creek. The setting is serene and private, with a gracious approach that complements the estate’s architectural presence. Impeccably built with careful attention to detail, the residence offers 4 bedrooms and 3.5 baths within a thoughtfully designed floor plan that maximizes natural light and water views. The living room, kitchen, and dining area flow comfortably together, creating a spacious central gathering area framed by expansive windows overlooking the creek and anchored by a fireplace. The kitchen is generously sized, featuring a substantial island, quality finishes, and an inviting eat-in area suited for both everyday living and entertaining. Outdoor living is equally compelling, with a screened porch overlooking the water and an in-ground pool set against sweeping creek views. The private pier provides deep water dockage, ideal for boating enthusiasts seeking immediate access to the Chesapeake Bay watershed. A finished rec room above the attached garage offers flexible use as a media room, office, or fitness space. In addition to the attached two-car garage, the property features a substantial detached multi-bay garage equipped with a hydraulic vehicle lift, air compressor, and rough-in for a future bath — an exceptional amenity for car collectors, hobbyists, or workshop space. This exceptional Island Creek estate combines craftsmanship, privacy, and premier waterfront living in a setting that is both refined and enduring.

4 Beds ⋅ 4 Baths

Island Creek Estate — rare total privacy, deep water dockage, meaningful architecture, and superb build quality all intersect at this remarkable, truly one-of-a-kind waterfront offering. Set on approximately 6 acres of park-like grounds with 500± feet of shoreline and 6’± MLW, the property offers exceptional water access along the peaceful expanse of Island Creek. The setting is serene and private, with a gracious approach that complements the estate’s architectural presence. Impeccably built with careful attention to detail, the residence offers 4 bedrooms and 3.5 baths within a thoughtfully designed floor plan that maximizes natural light and water views. The living room, kitchen, and dining area flow comfortably together, creating a spacious central gathering area framed by expansive windows overlooking the creek and anchored by a fireplace. The kitchen is generously sized, featuring a substantial island, quality finishes, and an inviting eat-in area suited for both everyday living and entertaining. Outdoor living is equally compelling, with a screened porch overlooking the water and an in-ground pool set against sweeping creek views. The private pier provides deep water dockage, ideal for boating enthusiasts seeking immediate access to the Chesapeake Bay watershed. A finished rec room above the attached garage offers flexible use as a media room, office, or fitness space. In addition to the attached two-car garage, the property features a substantial detached multi-bay garage equipped with a hydraulic vehicle lift, air compressor, and rough-in for a future bath — an exceptional amenity for car collectors, hobbyists, or workshop space. This exceptional Island Creek estate combines craftsmanship, privacy, and premier waterfront living in a setting that is both refined and enduring.

4346 Southside Ln, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact:

$189,000

Rare Easton Building Lot with Creek, Woods & Endless Possibilities Discover one of Easton's hidden gems! This beautiful, one-of-a-kind lot offers a private backyard sanctuary featuring a picturesque creek flowing through the property and peaceful wooded views. Nestled in a desirable family-friendly neighborhood, the lot is within walking distance of schools, ball fields, and community amenities. Whether you're planning to build your dream family home or a duplex investment property, this parcel is ready for development with essential utilities available, including broadband internet, public water, and public sewer. Opportunities like this are hard to find—enjoy the perfect blend of natural beauty, convenience, and development potential in a truly unique Easton location. Don't miss your chance to own this exceptional property!

Mecklenburg Avenue, Easton

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

$329,000

This easy one level living rancher is located in a quiet neighborhood between Easton and Cambridge on the scenic eastern shore of Maryland. There is a pond and playground within the community for residents use. You will enjoy relaxing on the rear screened in deck that overlooks a generous backyard. Appliances, window treatments, and 2 outdoor storage sheds convey with sale. This would make a wonderful starter or retirement home.

3 Beds ⋅ 1 Baths

This easy one level living rancher is located in a quiet neighborhood between Easton and Cambridge on the scenic eastern shore of Maryland. There is a pond and playground within the community for residents use. You will enjoy relaxing on the rear screened in deck that overlooks a generous backyard. Appliances, window treatments, and 2 outdoor storage sheds convey with sale. This would make a wonderful starter or retirement home.

3900 Harrison Cir, Trappe

Listing courtesy of Mr. Lister Realty. Contact:

$445,000

Chesapeake by Del Webb. Popular 2-story Wittman model. Spacious 3 bedroom, 3 bath home. Great room with gas fireplace, office, large kitchen with center island, granite countertops and breakfast nook. Primary bedroom suite with walk-in closet, bath with separate vanities, separate shower and soaking tub. Guest bedroom, hall bath with walk-in tub and laundry room. Sunroom, enclosed porch overlooking your own private fenced in-ground pool. 2nd floor features large loft, guest bedroom and bath perfect for visitors or separate living area. newer roof (approx. 7 years old). Economical gas heat. Recent interior painting of some rooms. Attached 2-car garage, patio and irrigation system. Sited on a corner lot close to the community amenities which include a Clubhouse, tennis/pickleball courts, exercise trails, community pool, bocce ball and picnic areas. 55+ age restricted section. Convenient location to downtown Easton, St. Michaels and Oxford, MD/DE beaches and metropolitan areas. Note: Seller will credit $5K at closing to open and maintain pool for next season with an acceptable offer.

3 Beds ⋅ 3 Baths

Chesapeake by Del Webb. Popular 2-story Wittman model. Spacious 3 bedroom, 3 bath home. Great room with gas fireplace, office, large kitchen with center island, granite countertops and breakfast nook. Primary bedroom suite with walk-in closet, bath with separate vanities, separate shower and soaking tub. Guest bedroom, hall bath with walk-in tub and laundry room. Sunroom, enclosed porch overlooking your own private fenced in-ground pool. 2nd floor features large loft, guest bedroom and bath perfect for visitors or separate living area. newer roof (approx. 7 years old). Economical gas heat. Recent interior painting of some rooms. Attached 2-car garage, patio and irrigation system. Sited on a corner lot close to the community amenities which include a Clubhouse, tennis/pickleball courts, exercise trails, community pool, bocce ball and picnic areas. 55+ age restricted section. Convenient location to downtown Easton, St. Michaels and Oxford, MD/DE beaches and metropolitan areas. Note: Seller will credit $5K at closing to open and maintain pool for next season with an acceptable offer.

29638 Janets Way, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

$1,250,000

A very exciting, well-built (stick built by Mister Construction-1996), open floor plan waterfront home in Oxford. Amazing broad South facing with river views. Three bedrooms on second floor, each with private bath, elevator to 3rd floor, full attic storage, 2 car garage, new roof in 2022, waterside deck, 2 enclosed waterfront sitting rooms, spacious first floor rooms for entertaining! First floor sitting room is large enough to use as 4th bedroom with full bath on first floor.

3 Beds ⋅ 4 Baths

A very exciting, well-built (stick built by Mister Construction-1996), open floor plan waterfront home in Oxford. Amazing broad South facing with river views. Three bedrooms on second floor, each with private bath, elevator to 3rd floor, full attic storage, 2 car garage, new roof in 2022, waterside deck, 2 enclosed waterfront sitting rooms, spacious first floor rooms for entertaining! First floor sitting room is large enough to use as 4th bedroom with full bath on first floor.

115 W, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

$399,000

Nestled on a desirable corner lot in Easton, this charming 3-bedroom, 2.5-bath home offers the perfect blend of comfort, convenience, and location. Just a short distance from a scenic walking trail, it’s ideal for those who enjoy outdoor strolls, morning jogs, or peaceful evenings surrounded by nature. Inside, the home features a functional and inviting layout with spacious living areas, perfect for both everyday living and entertaining. The kitchen flows seamlessly into the dining and living spaces, creating a warm and connected atmosphere. Central heating and air conditioning ensure year-round comfort no matter the season. Upstairs, you’ll find three well-sized bedrooms, including a primary suite with a private full bath. An additional full bathroom and a convenient half bath provide ample space for family and guests. Step outside to enjoy the rear deck, perfect for grilling, relaxing, or hosting gatherings. The attached garage adds convenience and extra storage. Located just minutes from downtown, you’ll have easy access to local shops, dining, and community events, making this home a wonderful opportunity to enjoy all that Easton has to offer.

3 Beds ⋅ 3 Baths

Nestled on a desirable corner lot in Easton, this charming 3-bedroom, 2.5-bath home offers the perfect blend of comfort, convenience, and location. Just a short distance from a scenic walking trail, it’s ideal for those who enjoy outdoor strolls, morning jogs, or peaceful evenings surrounded by nature. Inside, the home features a functional and inviting layout with spacious living areas, perfect for both everyday living and entertaining. The kitchen flows seamlessly into the dining and living spaces, creating a warm and connected atmosphere. Central heating and air conditioning ensure year-round comfort no matter the season. Upstairs, you’ll find three well-sized bedrooms, including a primary suite with a private full bath. An additional full bathroom and a convenient half bath provide ample space for family and guests. Step outside to enjoy the rear deck, perfect for grilling, relaxing, or hosting gatherings. The attached garage adds convenience and extra storage. Located just minutes from downtown, you’ll have easy access to local shops, dining, and community events, making this home a wonderful opportunity to enjoy all that Easton has to offer.

331 Hollis Cir, Easton

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$2,300,000

"New Scotland Farm" This special and unique offering includes 100 +/- acres of prime farm and hunting land, encompassing a spacious farmhouse and three additional income producing properties, two ponds, and deeded water access with a dock and slip on LaTrappe Creek. This offering consists of three parcels: Parcel #1 Main House with Rental Properties 21.34 +/- acres improved by a 5BR farmhouse (which includes a separately rented apartment above the garage), two guest cottages that are income producing, and two scenic ponds, one that can be hunted year round. A newly refurbished tennis court and pavilion overlook the second pond. The main house, a Victorian style farmhouse, has a brand new roof , geothermal units and outdoor deck. There is a historic section of the home and an addition built in the 1990’s. The main house also features a separate apartment above the garage for income potential, or ideal for a caretaker. Beautiful setting with mature trees, complete privacy and lovely vistas from several vantage points. Parcel #2 Land 83+/- acres (65 in till) in agriculture. Farm tenant in place. Community Boat Slip (25% interest) 1.424 +/- acres Deeded boat slip and water access on LaTrappe Creek via shared pier with 3 other homes. This is a unique property with an endless potential of uses, from a hunting retreat, private getaway, investment or combination of all.**Please do not drive onto the property without an appointment. The property has a hunting lease place.**

4 Beds ⋅ 3 Baths

"New Scotland Farm" This special and unique offering includes 100 +/- acres of prime farm and hunting land, encompassing a spacious farmhouse and three additional income producing properties, two ponds, and deeded water access with a dock and slip on LaTrappe Creek. This offering consists of three parcels: Parcel #1 Main House with Rental Properties 21.34 +/- acres improved by a 5BR farmhouse (which includes a separately rented apartment above the garage), two guest cottages that are income producing, and two scenic ponds, one that can be hunted year round. A newly refurbished tennis court and pavilion overlook the second pond. The main house, a Victorian style farmhouse, has a brand new roof , geothermal units and outdoor deck. There is a historic section of the home and an addition built in the 1990’s. The main house also features a separate apartment above the garage for income potential, or ideal for a caretaker. Beautiful setting with mature trees, complete privacy and lovely vistas from several vantage points. Parcel #2 Land 83+/- acres (65 in till) in agriculture. Farm tenant in place. Community Boat Slip (25% interest) 1.424 +/- acres Deeded boat slip and water access on LaTrappe Creek via shared pier with 3 other homes. This is a unique property with an endless potential of uses, from a hunting retreat, private getaway, investment or combination of all.**Please do not drive onto the property without an appointment. The property has a hunting lease place.**

28923 Island Creek Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact:

$2,300,000

"New Scotland Farm" This special and unique offering includes 100 +/- acres of prime farm and hunting land, encompassing a spacious farmhouse and three additional income producing properties, two ponds, and deeded water access with a dock and slip on LaTrappe Creek. This offering consists of three parcels: Parcel #1 Main House with Rental Properties 21.34 +/- acres improved by a 5BR farmhouse (which includes a separately rented apartment above the garage), two guest cottages that are income producing, and two scenic ponds, one that can be hunted year round. A newly refurbished tennis court and pavilion overlook the second pond. The main house, a Victorian style farmhouse, has a brand new roof , geothermal units and outdoor deck. There is a historic section of the home and an addition built in the 1990’s. The main house also features a separate apartment above the garage for income potential, or ideal for a caretaker. Beautiful setting with mature trees, complete privacy and lovely vistas from several vantage points. Parcel #2 Land 83+/- acres (65 in till) in agriculture. Farm tenant in place. Community Boat Slip (25% interest) 1.424 +/- acres Deeded boat slip and water access on LaTrappe Creek via shared pier with 3 other homes. This is a unique property with an endless potential of uses, from a hunting retreat, private getaway, investment or combination of all.**Please do not drive onto the property without an appointment. The property has a hunting lease place.**

4 Beds ⋅ 3 Baths

"New Scotland Farm" This special and unique offering includes 100 +/- acres of prime farm and hunting land, encompassing a spacious farmhouse and three additional income producing properties, two ponds, and deeded water access with a dock and slip on LaTrappe Creek. This offering consists of three parcels: Parcel #1 Main House with Rental Properties 21.34 +/- acres improved by a 5BR farmhouse (which includes a separately rented apartment above the garage), two guest cottages that are income producing, and two scenic ponds, one that can be hunted year round. A newly refurbished tennis court and pavilion overlook the second pond. The main house, a Victorian style farmhouse, has a brand new roof , geothermal units and outdoor deck. There is a historic section of the home and an addition built in the 1990’s. The main house also features a separate apartment above the garage for income potential, or ideal for a caretaker. Beautiful setting with mature trees, complete privacy and lovely vistas from several vantage points. Parcel #2 Land 83+/- acres (65 in till) in agriculture. Farm tenant in place. Community Boat Slip (25% interest) 1.424 +/- acres Deeded boat slip and water access on LaTrappe Creek via shared pier with 3 other homes. This is a unique property with an endless potential of uses, from a hunting retreat, private getaway, investment or combination of all.**Please do not drive onto the property without an appointment. The property has a hunting lease place.**

28923 Island Creek Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact:

$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:

$900,000

A prime commercial opportunity awaits at Easton Technology Park. This fully cleared 2.185-acre lot comes with all utilities — water, sewer, electric, and gas — already brought to the curb, making it truly move-in ready for your business. Zoned BC (Business Commercial), the property offers exceptional visibility and accessibility with direct access from Route 50. Situated directly across from Easton Airport and just minutes from the new University of Maryland Medical System Shore Regional Health Hospital, set to open in 2028, this location places your business at the heart of a rapidly growing corridor.

I-Way Ct, Easton

Listing courtesy of Meredith Fine Properties. Contact:

$800,000

A prime commercial opportunity awaits at Easton Technology Park. This fully cleared 2-acre lot comes with all utilities — water, sewer, electric, and gas — already brought to the curb, making it truly move-in ready for your business. Zoned BC (Business Commercial), the property offers exceptional visibility and accessibility with direct access from Route 50. Situated directly across from Easton Airport and just minutes from the new University of Maryland Medical System Shore Regional Health Hospital, set to open in 2028, this location places your business at the heart of a rapidly growing corridor.

I-Way Ct, Easton

Listing courtesy of Meredith Fine Properties. Contact:

$575,000

Nestled on over 2 acres in the desirable water access community of Deep Harbor Farm, this beautiful Cape Cod beams with natural light. The home features over 2,400 sqft with 4 bedrooms and 2.5 baths. The welcoming foyer overlooks a spacious dining room and leads to an open kitchen complete with white cabinetry, stainless steel appliances, breakfast bar and a large table space. Just off the kitchen, the expansive family room serves as the heart of the home with a stunning whitewashed fireplace. The first-floor primary bedroom provides convenience, while an additional main-level bedroom, currently used as an office, offers flexibility and the potential to create a larger primary suite. Upstairs, you’ll find two generously sized bedrooms, a full bath and abundant storage including eve storage and walk-in attic space. An attached 2-car garage and large detached shed add even more functionality. Enjoy the private 2-acre setting, ideal for outdoor living, gardening, or play, along with community water access, including a dock for boating, kayaking, and paddleboarding with direct access to the Chesapeake Bay, waterfront dining and some of the area’s best fishing and crabbing around.

4 Beds ⋅ 3 Baths

Nestled on over 2 acres in the desirable water access community of Deep Harbor Farm, this beautiful Cape Cod beams with natural light. The home features over 2,400 sqft with 4 bedrooms and 2.5 baths. The welcoming foyer overlooks a spacious dining room and leads to an open kitchen complete with white cabinetry, stainless steel appliances, breakfast bar and a large table space. Just off the kitchen, the expansive family room serves as the heart of the home with a stunning whitewashed fireplace. The first-floor primary bedroom provides convenience, while an additional main-level bedroom, currently used as an office, offers flexibility and the potential to create a larger primary suite. Upstairs, you’ll find two generously sized bedrooms, a full bath and abundant storage including eve storage and walk-in attic space. An attached 2-car garage and large detached shed add even more functionality. Enjoy the private 2-acre setting, ideal for outdoor living, gardening, or play, along with community water access, including a dock for boating, kayaking, and paddleboarding with direct access to the Chesapeake Bay, waterfront dining and some of the area’s best fishing and crabbing around.

6705 Tilghman Island Rd, Sherwood

Listing courtesy of Benson & Mangold, LLC. Contact:

$599,999

Motivated Seller and Improved Pricing! Whether seeking a year-round residence or a peaceful Eastern Shore getaway, Oxford offers a truly special place to call home. Discover this home and the exceptional opportunity to enjoy life in historic Oxford, Maryland. This inviting three- to four-bedroom home is located on a quiet cul-de-sac in the Jacks Point neighborhood, just a short distance from the waterfront. Vaulted ceilings and an open-concept layout create a bright, airy feel, while continuous Brazilian cherry hardwood floors add warmth and character throughout. The first-floor living space offers a generous foyer, flexible office or guest space, a separate dining room, a living room, a half bath, and an eat-in kitchen. The main second floor includes three bedrooms and two full baths, while a separate staircase provides access to a bonus room that can serve as a playroom, entertainment space, or private retreat. Beyond these rooms, a garage conversion completed before the current owner’s 2007 purchase expands the home with a large, light-filled family room and a separate storage area with interior and exterior access, providing ample room for lawn, garden, athletic, and marine equipment. The well maintained 28-year-old home has received steady updates, including a new roof in 2025, new appliances in 2024, first-floor HVAC system replacement in 2022, an encapsulated crawlspace, and more. It is move-in ready and priced to give the next owner flexibility to personalize the finishes and pursue future updates. Set on a quarter-acre lot with a fully fenced yard, the property offers ample space for outdoor living, a swimming pool, a shed, or an expanded garden. Endless possiblities! Just steps from the Oxford Community Center, Jacks Point Marina, Play Ball Dog Park, and the town center, the home also places shops, cafés, the museum, library, ice cream shop, yacht club and ferry within easy reach. The relaxed rhythm of Oxford life begins just beyond your front door.

4 Beds ⋅ 3 Baths

Motivated Seller and Improved Pricing! Whether seeking a year-round residence or a peaceful Eastern Shore getaway, Oxford offers a truly special place to call home. Discover this home and the exceptional opportunity to enjoy life in historic Oxford, Maryland. This inviting three- to four-bedroom home is located on a quiet cul-de-sac in the Jacks Point neighborhood, just a short distance from the waterfront. Vaulted ceilings and an open-concept layout create a bright, airy feel, while continuous Brazilian cherry hardwood floors add warmth and character throughout. The first-floor living space offers a generous foyer, flexible office or guest space, a separate dining room, a living room, a half bath, and an eat-in kitchen. The main second floor includes three bedrooms and two full baths, while a separate staircase provides access to a bonus room that can serve as a playroom, entertainment space, or private retreat. Beyond these rooms, a garage conversion completed before the current owner’s 2007 purchase expands the home with a large, light-filled family room and a separate storage area with interior and exterior access, providing ample room for lawn, garden, athletic, and marine equipment. The well maintained 28-year-old home has received steady updates, including a new roof in 2025, new appliances in 2024, first-floor HVAC system replacement in 2022, an encapsulated crawlspace, and more. It is move-in ready and priced to give the next owner flexibility to personalize the finishes and pursue future updates. Set on a quarter-acre lot with a fully fenced yard, the property offers ample space for outdoor living, a swimming pool, a shed, or an expanded garden. Endless possiblities! Just steps from the Oxford Community Center, Jacks Point Marina, Play Ball Dog Park, and the town center, the home also places shops, cafés, the museum, library, ice cream shop, yacht club and ferry within easy reach. The relaxed rhythm of Oxford life begins just beyond your front door.

209 Third St, Oxford

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

$420,000

Nestled along the peaceful waters of Swan Cove with access to Harris Creek, this circa 1890 farmhouse is full of Eastern Shore character and charm. Set on 1.38 private acres, the property offers the peace and serenity you’re seeking. The spacious enclosed front porch is accented with wood floors and a wood ceiling setting the tone of this charming home. The inviting foyer features original Crescent Moon shutters and leads into a bright open living room with hardwood floors and exposed wood beams ceilings. A cozy waterside den with a double-sided wood-burning fireplace is the perfect place to unwind. The kitchen offers tile floors and white cabinetry and leads to the dining room—complete with hardwood floors and a built-in barn wood bar overlooking the backyard and the cove beyond. The first-floor primary suite features hardwood floors, a double sided fireplace and a unique en-suite bath with a tub/shower combo. A second full bath and laundry room complete the main level, while two spacious guest bedrooms are located upstairs. Outside, the backyard patio is an ideal spot to relax or entertain. Launch a kayak, paddle board, canoe, or small flat-bottom boat and explore the surrounding creeks and rivers. Enjoy crabbing, fishing, and sunset cruises across Harris Creek. Multiple boat landings nearby offer easy access for avid boaters looking to enjoy, fishing, crabbing, water sports and all that the surrounding waterways have to offer. Located just 5 miles from historic St. Michaels, this home is just minutes from charming boutiques, renowned restaurants, and scenic waterfront attractions. Known for its vibrant maritime heritage and welcoming small-town feel, St. Michaels offers endless opportunities for boating, dining, and exploring.

3 Beds ⋅ 2 Baths

Nestled along the peaceful waters of Swan Cove with access to Harris Creek, this circa 1890 farmhouse is full of Eastern Shore character and charm. Set on 1.38 private acres, the property offers the peace and serenity you’re seeking. The spacious enclosed front porch is accented with wood floors and a wood ceiling setting the tone of this charming home. The inviting foyer features original Crescent Moon shutters and leads into a bright open living room with hardwood floors and exposed wood beams ceilings. A cozy waterside den with a double-sided wood-burning fireplace is the perfect place to unwind. The kitchen offers tile floors and white cabinetry and leads to the dining room—complete with hardwood floors and a built-in barn wood bar overlooking the backyard and the cove beyond. The first-floor primary suite features hardwood floors, a double sided fireplace and a unique en-suite bath with a tub/shower combo. A second full bath and laundry room complete the main level, while two spacious guest bedrooms are located upstairs. Outside, the backyard patio is an ideal spot to relax or entertain. Launch a kayak, paddle board, canoe, or small flat-bottom boat and explore the surrounding creeks and rivers. Enjoy crabbing, fishing, and sunset cruises across Harris Creek. Multiple boat landings nearby offer easy access for avid boaters looking to enjoy, fishing, crabbing, water sports and all that the surrounding waterways have to offer. Located just 5 miles from historic St. Michaels, this home is just minutes from charming boutiques, renowned restaurants, and scenic waterfront attractions. Known for its vibrant maritime heritage and welcoming small-town feel, St. Michaels offers endless opportunities for boating, dining, and exploring.

8000 Bozman Neavitt Rd, Bozman

Listing courtesy of Benson & Mangold, LLC. Contact:

$147,200

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

25832 Turner Ave, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

$126,400

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

25833 Turner Ave, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

$100,800

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

25831 Turner Ave, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

$549,000

Build your dream home on this exceptional 4.26-acre waterfront lot in the prestigious Llandaff at Cookes Hope community. Perc approved for a 7-bedroom home with the rare option for a basement, this property offers approximately 361 feet of frontage on Peachblossom Creek with the ability to build a dock—perfect for enjoying serene views and waterfront living. Ideally located just minutes from Easton and the Oxford corridor, this peaceful setting combines privacy with convenience. A rare opportunity to create your own Eastern Shore retreat. With an acceptable offer, seller to include bid drawings worth $45,000. Home rendering photos are for reference only, no construction has begun.

28850 Jennings Rd, Easton

Listing courtesy of ERA Martin Associates. Contact:

$2,000,000

PRICE IMPROVEMENT.... PRIVATE Estate Living Minutes from Historic St. Michaels... Escape to nearly twenty acres of unspoiled countryside just moments from the charm and waterfront allure of historic St. Michaels. This 4,492-square-foot home offers refined comfort with four bedrooms, two and a half baths, and a gourmet kitchen designed for both everyday living and effortless entertaining. A dedicated space for a future elevator adds thoughtful flexibility for years to come. Outside, the possibilities are as expansive as the land itself- 19.5 private acres with pastures suited for up to eleven Horses, plus a car barn for storage, hobbies, or collections. Agricultural and livestock production also permitted (buyers should confirm specifics with Easton P&Z). Notably, 5.75 wooded acres are enrolled in the DNR's Forest Stewardship Plan, preserving the agricultural tax discount without the requirement to grow crops or house livestock.

4 Beds ⋅ 3 Baths

PRICE IMPROVEMENT.... PRIVATE Estate Living Minutes from Historic St. Michaels... Escape to nearly twenty acres of unspoiled countryside just moments from the charm and waterfront allure of historic St. Michaels. This 4,492-square-foot home offers refined comfort with four bedrooms, two and a half baths, and a gourmet kitchen designed for both everyday living and effortless entertaining. A dedicated space for a future elevator adds thoughtful flexibility for years to come. Outside, the possibilities are as expansive as the land itself- 19.5 private acres with pastures suited for up to eleven Horses, plus a car barn for storage, hobbies, or collections. Agricultural and livestock production also permitted (buyers should confirm specifics with Easton P&Z). Notably, 5.75 wooded acres are enrolled in the DNR's Forest Stewardship Plan, preserving the agricultural tax discount without the requirement to grow crops or house livestock.

7909 Church Nck, Saint Michaels

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

$2,149,000

BACK ON THE MARKET WITH A NEW PRICE — DON’T MISS THIS EXCEPTIONAL WATERFRONT OPPORTUNITY! Tucked away in the highly desirable Drum Point neighborhood of St. Michaels, this exceptional waterfront retreat offers a rare combination of privacy, comfort, and quintessential Eastern Shore charm—all just minutes from the heart of town. Formerly a successful vacation rental, this beautifully maintained three-bedroom brick home is designed for relaxed year-round living and effortless entertaining. The inviting open floor plan features rich wood flooring, double-sided fireplace, a renovated kitchen, updated bathrooms, and energy-efficient geothermal HVAC. Water views are part of everyday life here. Spend quiet mornings beneath the shade of mature trees along the shoreline, unwind in the hammock as the Chesapeake breezes drift by, or gather with friends and family for unforgettable outdoor entertaining. The expansive deck features a built-in outdoor kitchen and hot tub, while a charming stone-walled patio offers another inviting space to relax. An outdoor shower makes post-swim cleanup easy, and the private pool provides the perfect place to cool off on warm summer days. For boating enthusiasts, the property delivers exceptional waterfront amenities with a private dock offering approximately 3 feet MLW, a boat lift, and a boat launch, providing convenient access to the water. A separate two-room detached studio with a covered porch adds even more versatility—perfect for visiting guests, a home office, creative pursuits, or a private getaway—all while taking in beautiful water views. Additional features include an encapsulated crawl space and numerous thoughtful updates throughout the property. And when you're ready to explore beyond your own waterfront haven, you're just minutes from the best of St. Michaels, including acclaimed restaurants, boutique shopping, charming cafés, the Classic Motor Museum, and the Chesapeake Bay Maritime Museum. Private, picturesque, and perfectly positioned—this is a rare opportunity to experience the very best of Eastern Shore waterfront living in one of St. Michaels' most sought-after neighborhoods.

3 Beds ⋅ 3 Baths

BACK ON THE MARKET WITH A NEW PRICE — DON’T MISS THIS EXCEPTIONAL WATERFRONT OPPORTUNITY! Tucked away in the highly desirable Drum Point neighborhood of St. Michaels, this exceptional waterfront retreat offers a rare combination of privacy, comfort, and quintessential Eastern Shore charm—all just minutes from the heart of town. Formerly a successful vacation rental, this beautifully maintained three-bedroom brick home is designed for relaxed year-round living and effortless entertaining. The inviting open floor plan features rich wood flooring, double-sided fireplace, a renovated kitchen, updated bathrooms, and energy-efficient geothermal HVAC. Water views are part of everyday life here. Spend quiet mornings beneath the shade of mature trees along the shoreline, unwind in the hammock as the Chesapeake breezes drift by, or gather with friends and family for unforgettable outdoor entertaining. The expansive deck features a built-in outdoor kitchen and hot tub, while a charming stone-walled patio offers another inviting space to relax. An outdoor shower makes post-swim cleanup easy, and the private pool provides the perfect place to cool off on warm summer days. For boating enthusiasts, the property delivers exceptional waterfront amenities with a private dock offering approximately 3 feet MLW, a boat lift, and a boat launch, providing convenient access to the water. A separate two-room detached studio with a covered porch adds even more versatility—perfect for visiting guests, a home office, creative pursuits, or a private getaway—all while taking in beautiful water views. Additional features include an encapsulated crawl space and numerous thoughtful updates throughout the property. And when you're ready to explore beyond your own waterfront haven, you're just minutes from the best of St. Michaels, including acclaimed restaurants, boutique shopping, charming cafés, the Classic Motor Museum, and the Chesapeake Bay Maritime Museum. Private, picturesque, and perfectly positioned—this is a rare opportunity to experience the very best of Eastern Shore waterfront living in one of St. Michaels' most sought-after neighborhoods.

7149 Drum Pt, Saint Michaels

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

$6,890,000

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

4 Beds ⋅ 5 Baths

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

5289 Ferry Neck Rd, Royal Oak

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

$175,000

Real Estate not included A full-featured screen printing and embroidery business is available for sale, including all essential equipment, accessories, and an established customer base, making it a turnkey opportunity for entrepreneurs. Business Overview This type of business typically combines screen printing and embroidery services, catering to both individuals and organizations seeking branded apparel, uniforms, promotional items, and custom merchandise The business can operate full or part-time , offering personalized services ranging from monogramming and logo embroidery to multicolor screen printing for shirts, hoodies, hats, and even towels or canvas products. Embroidery is ideal for textured and thicker fabrics, while screen printing works best on smooth fabrics like cotton or blends. Equipment Included Equipment for sale encompasses everything needed to produce high-quality customized garments: Embroidery machines: Multi-head industrial Brother machines capable of handling multiple projects efficiently. 1. Screen printing presses: units provide precise, high-volume production 2. Drying and curing systems: Conveyor dryers, flash units, and heat presses for curing inks Brother embroidery machines are renowned for combining durability, advanced technology, and ease of use, offering a wide range of models suitable for beginners to professional crafters. General Features Brother embroidery machines are designed to handle various projects, from personalizing apparel to home décor embellishments. Key features include: Built-in designs and fonts: Most Brother machines come with hundreds of built-in embroidery designs, frame patterns, and lettering fonts, allowing monogramming and creative projects.

4929 Ocean Gtwy, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact:

$449,900

Unique, one-of-a-kind property located in the heart of Tilghman Island, offering unparalleled tranquility and breathtaking water views overlooking Dogwood Harbor. Welcome to your private Eastern Shore retreat! This beautifully updated water-view home captures the essence of coastal living with sweeping views of the harbor and surrounding wildlife. Enjoy stunning sunsets and peaceful mornings from the expansive screened porch or spacious deck—perfect for relaxing or entertaining while taking in the natural beauty of the island. Inside, the home has been thoughtfully updated and features a bright, open living area and a beautifully renovated kitchen designed for both everyday living and gatherings with family and friends. The spacious primary suite offers a private bath and walk-in closet, along with panoramic water views and direct access to the second-story porch/deck with a retractable awning—an ideal place to unwind and enjoy the serene surroundings. Two additional guest bedrooms and a full bath complete the home’s comfortable and functional layout. Additional highlights include a charming screened porch, generous outdoor living spaces, a storage shed, and beautifully landscaped patios and walkways that enhance the home’s inviting coastal atmosphere. Located in the heart of Tilghman Island, this exceptional property offers the perfect opportunity to relax, boat, fish, and explore everything the Eastern Shore lifestyle has to offer.

3 Beds ⋅ 3 Baths

Unique, one-of-a-kind property located in the heart of Tilghman Island, offering unparalleled tranquility and breathtaking water views overlooking Dogwood Harbor. Welcome to your private Eastern Shore retreat! This beautifully updated water-view home captures the essence of coastal living with sweeping views of the harbor and surrounding wildlife. Enjoy stunning sunsets and peaceful mornings from the expansive screened porch or spacious deck—perfect for relaxing or entertaining while taking in the natural beauty of the island. Inside, the home has been thoughtfully updated and features a bright, open living area and a beautifully renovated kitchen designed for both everyday living and gatherings with family and friends. The spacious primary suite offers a private bath and walk-in closet, along with panoramic water views and direct access to the second-story porch/deck with a retractable awning—an ideal place to unwind and enjoy the serene surroundings. Two additional guest bedrooms and a full bath complete the home’s comfortable and functional layout. Additional highlights include a charming screened porch, generous outdoor living spaces, a storage shed, and beautifully landscaped patios and walkways that enhance the home’s inviting coastal atmosphere. Located in the heart of Tilghman Island, this exceptional property offers the perfect opportunity to relax, boat, fish, and explore everything the Eastern Shore lifestyle has to offer.

5933 Tilghman Island Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact:

$997,000

Price Improvement!!! Looking for the ideal downtown Easton location? This beautifully renovated Colonial offers a rare opportunity—perfect as a high‑end investment property or as your personal residence with an income‑producing second unit. This stunning building features two fully updated 1,000 sq. ft. units, each finished with high‑quality materials and thoughtful design. ✦ First‑Floor Unit 2 bedrooms, 2 baths Gourmet kitchen with premium finishes In‑unit washer/dryer Fireplace and hardwood floors Relaxing front porch and covered rear deck with landlord‑provided furniture Large private parking lot behind the building Easy walking distance to Easton’s restaurants, shops, and entertainment ✦ Second‑Floor Unit Offered fully furnished Mirrors the first‑floor layout and upgrades Primary bedroom with access to a second‑story balcony Turnkey and ready for immediate occupancy Together, the two units generate $5,670 per month, making this an exceptional opportunity for investors, entrepreneurs, or owner‑occupants seeking both comfort and cash flow. With its prime location and high‑end renovation, this exquisite property won’t last. Call today to schedule your private showing.

140 S Washington St, Easton

Listing courtesy of Meredith Fine Properties. Contact:

$997,000

Just Reduced!!!! Looking for the ideal downtown Easton location? This beautifully renovated Colonial offers a rare opportunity—perfect as a high‑end investment property or as your personal residence with an income‑producing second unit. This stunning building features two fully updated 1,000 sq. ft. units, each finished with high‑quality materials and thoughtful design. ✦ First‑Floor Unit 2 bedrooms, 2 baths Gourmet kitchen with premium finishes In‑unit washer/dryer Fireplace and hardwood floors Relaxing front porch and covered rear deck with landlord‑provided furniture Large private parking lot behind the building Easy walking distance to Easton’s restaurants, shops, and entertainment ✦ Second‑Floor Unit Offered fully furnished Mirrors the first‑floor layout and upgrades Primary bedroom with access to a second‑story balcony Turnkey and ready for immediate occupancy Together, the two units generate $5670 per month, making this an exceptional opportunity for investors, entrepreneurs, or owner‑occupants seeking both comfort and cash flow. With its prime location and high‑end renovation, this exquisite property won’t last. Call today to schedule your private showing.

4 Beds ⋅ 4 Baths

Just Reduced!!!! Looking for the ideal downtown Easton location? This beautifully renovated Colonial offers a rare opportunity—perfect as a high‑end investment property or as your personal residence with an income‑producing second unit. This stunning building features two fully updated 1,000 sq. ft. units, each finished with high‑quality materials and thoughtful design. ✦ First‑Floor Unit 2 bedrooms, 2 baths Gourmet kitchen with premium finishes In‑unit washer/dryer Fireplace and hardwood floors Relaxing front porch and covered rear deck with landlord‑provided furniture Large private parking lot behind the building Easy walking distance to Easton’s restaurants, shops, and entertainment ✦ Second‑Floor Unit Offered fully furnished Mirrors the first‑floor layout and upgrades Primary bedroom with access to a second‑story balcony Turnkey and ready for immediate occupancy Together, the two units generate $5670 per month, making this an exceptional opportunity for investors, entrepreneurs, or owner‑occupants seeking both comfort and cash flow. With its prime location and high‑end renovation, this exquisite property won’t last. Call today to schedule your private showing.

140 S Washington St, Easton

Listing courtesy of Meredith Fine Properties. Contact:

$997,000

Beautifully restored Historic Victorian in the heart of Saint Michaels. From the wide, welcoming front porch to the gated, manicured yard—complete with a hammock ideal for long afternoon naps—every space is designed for comfort and relaxation. A brick walkway leads to the custom beveled‑glass entry door and into the warm, inviting family room. Inside, the home features rich pine floors throughout, a cherry kitchen with stainless steel appliances, granite countertops, and an open flow into the charming dining room. The spacious family room includes a propane stove for cozy winter days. The first floor also offers a full laundry room and an ornate powder room. The original staircase leads to the second floor, which includes three bedrooms and a renovated marble‑tile full bath. The private third‑floor primary suite offers a peaceful retreat with its own en‑suite bath. Seller raised the home 3 feet and the lot 2 feet to help will water run-off and has a dry encapsulated crawl space with cement floor. Just one block from the water—with water views from the street—this home captures the best of small‑town living. Enjoy walking access to Saint Michaels’ restaurants, quaint shops, kayaking, swimming, boating, and biking. It’s a special property ready for unforgettable memories with family and friends. Whether you're looking for a proven investment property or a beautiful home for your family, this one stands out.

4 Beds ⋅ 3 Baths

Beautifully restored Historic Victorian in the heart of Saint Michaels. From the wide, welcoming front porch to the gated, manicured yard—complete with a hammock ideal for long afternoon naps—every space is designed for comfort and relaxation. A brick walkway leads to the custom beveled‑glass entry door and into the warm, inviting family room. Inside, the home features rich pine floors throughout, a cherry kitchen with stainless steel appliances, granite countertops, and an open flow into the charming dining room. The spacious family room includes a propane stove for cozy winter days. The first floor also offers a full laundry room and an ornate powder room. The original staircase leads to the second floor, which includes three bedrooms and a renovated marble‑tile full bath. The private third‑floor primary suite offers a peaceful retreat with its own en‑suite bath. Seller raised the home 3 feet and the lot 2 feet to help will water run-off and has a dry encapsulated crawl space with cement floor. Just one block from the water—with water views from the street—this home captures the best of small‑town living. Enjoy walking access to Saint Michaels’ restaurants, quaint shops, kayaking, swimming, boating, and biking. It’s a special property ready for unforgettable memories with family and friends. Whether you're looking for a proven investment property or a beautiful home for your family, this one stands out.

101 Mulberry St, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact:

$899,000

Located minutes from St. Michaels this waterfront property is a boater's dream. Tilghman, is a small island big on history, nature and local lore. Situated just over the Knapps Narrows Bridge this home offers a main house with first floor primary suite. The first floor is open with custom details and just perfect for hosting friends and family. A custom spiral staircase leads to a second floor with 4 additional guest bedrooms and bath. This renovated home also has a separate 3 bay garage with a 2-bedroom 2-bath water view apartment with a nice open living and dining area and total square footage of 768. The main house has an attached 1 bedroom 1 bath in-law suite. Great space for your guests or potential for a vacation rental. A nice wide-open lawn leads you to the dock with 7 boat slips. Right on the Knapps Narrows. Tilghman is the perfect place to start making your Eastern Shore Memories. New pictures to come...

5 Beds ⋅ 2 Baths

Located minutes from St. Michaels this waterfront property is a boater's dream. Tilghman, is a small island big on history, nature and local lore. Situated just over the Knapps Narrows Bridge this home offers a main house with first floor primary suite. The first floor is open with custom details and just perfect for hosting friends and family. A custom spiral staircase leads to a second floor with 4 additional guest bedrooms and bath. This renovated home also has a separate 3 bay garage with a 2-bedroom 2-bath water view apartment with a nice open living and dining area and total square footage of 768. The main house has an attached 1 bedroom 1 bath in-law suite. Great space for your guests or potential for a vacation rental. A nice wide-open lawn leads you to the dock with 7 boat slips. Right on the Knapps Narrows. Tilghman is the perfect place to start making your Eastern Shore Memories. New pictures to come...

21552 Chicken Point Rd, Tilghman

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

$799,000

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:

How much is your home worth?

How much is your home worth?