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Well Maintained Rancher offers 3 bedrooms and 2 full baths with a spacious, well-designed layout. The Kitchen is a standout, featuring granite countertops, abundant cabinetry, a walk-in pantry, center island, and a bar area with seating for six—perfect for entertaining. The cozy living room is filled with natural light and features a warm gas fireplace for relaxing evenings at home. Beautiful wood flooring and an additional flexible room ideal for a home office, den, or relaxation space, complete with sliding doors leading to the rear yard. The primary suite provides a private retreat with a large walk-in closet, double sink vanity, soaking tub, and a separate shower with barn-style door entrance. Relax outdoors on the covered porch, perfect for morning coffee or unwinding at the end of the day. Additional highlights include a separate laundry room, a 2-car garage with epoxy flooring, and a blacktop driveway, all located within an established subdivision. Close to Fine Dining, Grocery, Shopping, Deli's. This is a must see!

29770 Captain Adamouski St, Easton

Listing courtesy of Keller Williams Select Realtors of Cambridge. Contact: 4102711265

$4,395,000

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: 4108226665

$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: 4108226665

$2,495,000

Incredibly rare Cooke’s Hope at Llandaff opportunity featuring nearly 39+/- acres, a 3,800 +/- custom home all 5 minutes of Easton. As you enter “38 Special Acres” you are greeted with views of the farm and pond and you can see why this property is different from all the others. As the driveway curves around you can see the beautiful Abel built home 3 bay detached garage, and pool house. Upon parking you realize that you can not see another house. As you enter the house the quality of construction is evident with high ceilings, wood floors, and view of the incredible pool area and views of Peachblossom Creek. The open floor plan is comfortable and well suited for entertaining, also offering a cozy den and an office that over look the acreage. The primary suite is stunning with an incredible bath with jetted tub and walk-in shower. The custom closet is enormous with built in drawers and automatic lights. Exploring the first floor even more you will find a gracious laundry room that features the coolest dog washing station that you have ever seen with hot and cold water and tile floors this feature alone sets off the house. The entire house is CAT6 wired with a water filtration system and a whole house reverse osmosis system with holding tanks that hold 150 gallons of treated water. Outside the star of the show is the deck and pool area. The concrete pool and separate hot tub that over look the creek are incredible with a pool house that has a changing area and full bath. There is a 2 car attached garage with a 3 bay detached garage with one bay that is fully insulated for that special car you want to keep out of the weather. There are not many places to hunt this close to Easton but with the pond and 20 acre additional wooded parcel there are waterfowl, deer and turkey opportunities right out your back door. The home also features a first floor and pool generator, and RV plug. There are so many unique things about this property it has to be seen to be believed.

4 Beds ⋅ 4 Baths

Incredibly rare Cooke’s Hope at Llandaff opportunity featuring nearly 39+/- acres, a 3,800 +/- custom home all 5 minutes of Easton. As you enter “38 Special Acres” you are greeted with views of the farm and pond and you can see why this property is different from all the others. As the driveway curves around you can see the beautiful Abel built home 3 bay detached garage, and pool house. Upon parking you realize that you can not see another house. As you enter the house the quality of construction is evident with high ceilings, wood floors, and view of the incredible pool area and views of Peachblossom Creek. The open floor plan is comfortable and well suited for entertaining, also offering a cozy den and an office that over look the acreage. The primary suite is stunning with an incredible bath with jetted tub and walk-in shower. The custom closet is enormous with built in drawers and automatic lights. Exploring the first floor even more you will find a gracious laundry room that features the coolest dog washing station that you have ever seen with hot and cold water and tile floors this feature alone sets off the house. The entire house is CAT6 wired with a water filtration system and a whole house reverse osmosis system with holding tanks that hold 150 gallons of treated water. Outside the star of the show is the deck and pool area. The concrete pool and separate hot tub that over look the creek are incredible with a pool house that has a changing area and full bath. There is a 2 car attached garage with a 3 bay detached garage with one bay that is fully insulated for that special car you want to keep out of the weather. There are not many places to hunt this close to Easton but with the pond and 20 acre additional wooded parcel there are waterfowl, deer and turkey opportunities right out your back door. The home also features a first floor and pool generator, and RV plug. There are so many unique things about this property it has to be seen to be believed.

28910 Jennings Rd, Easton

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

$509,990

**Red Tag Sales Event through August 2, 2026! Was $519,990 Now: $509,990!** Come and see 29885 Londyn Lane in Easton, MD, a new two-story home in Gannon Range. This Azalea home offers four bedrooms, three bathrooms, 9' ceilings, a loft, and a two-car garage. The welcoming foyer has two coat closets and separates to afford privacy to the two spacious guest bedrooms with closets and the secondary bathroom. The open floorplan features a well-designed kitchen complete with beautiful white cabinets, an oversized island with granite countertops, a pantry closet, and stainless-steel appliances. The kitchen is open to the breakfast nook, dining area, and great room making it easy to spend time with friends and family. The large laundry room, tucked between the kitchen and the two-car garage, also features an additional coat closet. The private owner’s suite is a retreat in the back of the home with a spacious bathroom with a luxury shower and a large walk-in closet. This home also offers an expansive second-floor addition, with an open loft, full bathroom, and a fourth bedroom. Enjoy the private covered porch overlooking the back of the home and the fully sodded and irrigated lawn. This home includes white window treatments and the exclusive Smart Home® package. Pictures, artist renderings, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Image representative of plan only and may vary as built. Images are of model home and include custom design features that may not be available in other homes. Furnishings and decorative items not included with home purchase.

**Red Tag Sales Event through August 2, 2026! Was $519,990 Now: $509,990!** Come and see 29885 Londyn Lane in Easton, MD, a new two-story home in Gannon Range. This Azalea home offers four bedrooms, three bathrooms, 9' ceilings, a loft, and a two-car garage. The welcoming foyer has two coat closets and separates to afford privacy to the two spacious guest bedrooms with closets and the secondary bathroom. The open floorplan features a well-designed kitchen complete with beautiful white cabinets, an oversized island with granite countertops, a pantry closet, and stainless-steel appliances. The kitchen is open to the breakfast nook, dining area, and great room making it easy to spend time with friends and family. The large laundry room, tucked between the kitchen and the two-car garage, also features an additional coat closet. The private owner’s suite is a retreat in the back of the home with a spacious bathroom with a luxury shower and a large walk-in closet. This home also offers an expansive second-floor addition, with an open loft, full bathroom, and a fourth bedroom. Enjoy the private covered porch overlooking the back of the home and the fully sodded and irrigated lawn. This home includes white window treatments and the exclusive Smart Home® package. Pictures, artist renderings, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Image representative of plan only and may vary as built. Images are of model home and include custom design features that may not be available in other homes. Furnishings and decorative items not included with home purchase.

29885 Londyn Ln, Easton

Listing courtesy of D.R. Horton Realty of Virginia, LLC. Contact: 3017013700

$559,000

Discover this inviting home in The Easton Club along the desirable Oxford Corridor. Photos coming soon. Welcome to a beautifully designed two‑level residence in the sought‑after Easton Club community. Built in 1995, this home blends timeless style with an open, light‑filled layout that offers both comfort and flexibility. The main level features a spacious primary suite with a luxury en suite bath, creating a private retreat. A separate guest wing includes a second bedroom and full bath—ideal for visitors. The living room, home office, and primary suite all open onto a full‑width deck overlooking the property and community grounds, providing a perfect setting for entertaining or quiet outdoor relaxation. Upstairs, a skylit TV room expands your living space, accompanied by a third bedroom, full bath, and climate‑controlled storage. An attached side‑load two‑car garage adds everyday convenience. The Easton Club is a picturesque neighborhood originally designed around a golf course and now reimagined as open green space with cart paths, abundant wildlife, and scenic views along the Tred Avon River. Residents enjoy outstanding amenities including a swimming pool, tennis and pickleball courts, sidewalks, and public water and sewer. This home offers a rare opportunity to enjoy resort‑style living in one of Easton’s most desirable communities, all just minutes from town conveniences.

Discover this inviting home in The Easton Club along the desirable Oxford Corridor. Photos coming soon. Welcome to a beautifully designed two‑level residence in the sought‑after Easton Club community. Built in 1995, this home blends timeless style with an open, light‑filled layout that offers both comfort and flexibility. The main level features a spacious primary suite with a luxury en suite bath, creating a private retreat. A separate guest wing includes a second bedroom and full bath—ideal for visitors. The living room, home office, and primary suite all open onto a full‑width deck overlooking the property and community grounds, providing a perfect setting for entertaining or quiet outdoor relaxation. Upstairs, a skylit TV room expands your living space, accompanied by a third bedroom, full bath, and climate‑controlled storage. An attached side‑load two‑car garage adds everyday convenience. The Easton Club is a picturesque neighborhood originally designed around a golf course and now reimagined as open green space with cart paths, abundant wildlife, and scenic views along the Tred Avon River. Residents enjoy outstanding amenities including a swimming pool, tennis and pickleball courts, sidewalks, and public water and sewer. This home offers a rare opportunity to enjoy resort‑style living in one of Easton’s most desirable communities, all just minutes from town conveniences.

28642 Clubhouse Dr, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$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: (410) 486-5478

$480,000

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, picnic areas, putting green. 55+ age restricted section. Convenient location to downtown Easton, St. Michaels and Oxford, MD/DE beaches and metropolitan areas. NOTE: Coastal Pools is in the process of completing extensive renovation of the pool

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, picnic areas, putting green. 55+ age restricted section. Convenient location to downtown Easton, St. Michaels and Oxford, MD/DE beaches and metropolitan areas. NOTE: Coastal Pools is in the process of completing extensive renovation of the pool

29638 Janets Way, Easton

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 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

$1,250,000

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 Pier St, Oxford

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

$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.

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" First time offered in decades! 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. There is the potential for subdivision of 4 lots outside the of the critical area. (buyer to verify) 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.

"New Scotland Farm" First time offered in decades! 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. There is the potential for subdivision of 4 lots outside the of the critical area. (buyer to verify) 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.

28923 Island Creek Rd, Trappe

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

$1,379,800

Under construction by Laine Street Homes, this exceptional property offers over 3,300 sq ft of finished living space plus an additional 480 sq ft of covered outdoor living. Set on approximately 2 acres with mature trees and located just minutes from the heart of historic St. Michaels, the home blends privacy, luxury, and convenience. Designed with a main-level primary suite, the floor plan delivers comfort and ease. High‑end finishes include Shaw luxury vinyl plank flooring, a gourmet kitchen with a 48" dual‑fuel range, custom tile backsplash, quartz countertops, stainless steel appliances, and a spacious walk‑in pantry. The inviting living area features a fireplace and seamless access to the covered front and rear porches. The primary suite offers a true retreat with a spa‑inspired ensuite bathroom, soaking tub, walk‑in shower, sitting area, and a large custom closet. Additional highlights include a dedicated laundry room, public sewer, and thoughtful craftsmanship throughout. This beautifully designed home is a must‑see for anyone seeking luxury living in one of Maryland’s most charming waterfront towns.

4 Beds ⋅ 4 Baths

Under construction by Laine Street Homes, this exceptional property offers over 3,300 sq ft of finished living space plus an additional 480 sq ft of covered outdoor living. Set on approximately 2 acres with mature trees and located just minutes from the heart of historic St. Michaels, the home blends privacy, luxury, and convenience. Designed with a main-level primary suite, the floor plan delivers comfort and ease. High‑end finishes include Shaw luxury vinyl plank flooring, a gourmet kitchen with a 48" dual‑fuel range, custom tile backsplash, quartz countertops, stainless steel appliances, and a spacious walk‑in pantry. The inviting living area features a fireplace and seamless access to the covered front and rear porches. The primary suite offers a true retreat with a spa‑inspired ensuite bathroom, soaking tub, walk‑in shower, sitting area, and a large custom closet. Additional highlights include a dedicated laundry room, public sewer, and thoughtful craftsmanship throughout. This beautifully designed home is a must‑see for anyone seeking luxury living in one of Maryland’s most charming waterfront towns.

7865 Pea Neck, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$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

$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.

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: (410) 745-0415

$655,000

Improved Pricing ! Make this Charming Oxford Gem your new home. This well-maintained 4-bedroom, 2.5-bath home offers a comfortable blend of classic style and Eastern Shore charm in a prime Oxford location. Whether you're looking for a first home, a retirement retreat, a weekend escape, or an investment property, this inviting residence is designed to fit a variety of lifestyles. Tucked away on a quiet cul-de-sac, it features welcoming indoor and outdoor spaces ideal for year-round living, with plenty of room to transform/grow and make it your own. Inside, the foyer opens to spacious living and dining areas featuring Brazilian cherry hardwood floors, vaulted ceilings, and abundant natural light. French doors lead to a flexible room that can serve as a first floor guest room or home office. The living room flows into a large kitchen with a bright breakfast room and an adjacent dining area, making it ideal for casual mornings and gatherings with family and friends. Just off the kitchen, a half bath and a large family room provide added convenience and direct access to a spacious backyard. Upstairs, the primary suite offers a peaceful retreat with a large walk-in closet and an en-suite bath featuring double sinks, a Jacuzzi tub, and a walk-in shower. Two additional bedrooms share a generous hall bath with double sinks and a tub-shower combination. A second-floor bonus room adds even more flexibility and can be used as a playroom, home gym, game room, or private retreat. Outdoor living is equally appealing, with a front and back decks, patio with fire pit and a fully fenced backyard. One of the largest yards in the neighborhood, with plenty of room for a pool. Located just a short walk from downtown Oxford, the home offers easy access to local shops, restaurants, the waterfront park, Oxford Market, and Scottish Highland Creamery. Move-in ready and full of character, this Eastern Shore gem delivers exceptional value. Move-in ready and full of character, this Eastern Shore gem offers the best of Oxford living at an exceptional value. Recent Upgrades include: A new roof installed in August 2025, Stainless-steel appliances less than two years old, encapsulated crawlspace.

Improved Pricing ! Make this Charming Oxford Gem your new home. This well-maintained 4-bedroom, 2.5-bath home offers a comfortable blend of classic style and Eastern Shore charm in a prime Oxford location. Whether you're looking for a first home, a retirement retreat, a weekend escape, or an investment property, this inviting residence is designed to fit a variety of lifestyles. Tucked away on a quiet cul-de-sac, it features welcoming indoor and outdoor spaces ideal for year-round living, with plenty of room to transform/grow and make it your own. Inside, the foyer opens to spacious living and dining areas featuring Brazilian cherry hardwood floors, vaulted ceilings, and abundant natural light. French doors lead to a flexible room that can serve as a first floor guest room or home office. The living room flows into a large kitchen with a bright breakfast room and an adjacent dining area, making it ideal for casual mornings and gatherings with family and friends. Just off the kitchen, a half bath and a large family room provide added convenience and direct access to a spacious backyard. Upstairs, the primary suite offers a peaceful retreat with a large walk-in closet and an en-suite bath featuring double sinks, a Jacuzzi tub, and a walk-in shower. Two additional bedrooms share a generous hall bath with double sinks and a tub-shower combination. A second-floor bonus room adds even more flexibility and can be used as a playroom, home gym, game room, or private retreat. Outdoor living is equally appealing, with a front and back decks, patio with fire pit and a fully fenced backyard. One of the largest yards in the neighborhood, with plenty of room for a pool. Located just a short walk from downtown Oxford, the home offers easy access to local shops, restaurants, the waterfront park, Oxford Market, and Scottish Highland Creamery. Move-in ready and full of character, this Eastern Shore gem delivers exceptional value. Move-in ready and full of character, this Eastern Shore gem offers the best of Oxford living at an exceptional value. Recent Upgrades include: A new roof installed in August 2025, Stainless-steel appliances less than two years old, encapsulated crawlspace.

209 Third St, Oxford

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

$360,000

Welcome to 402 Cherry Street, a beautifully, renovated three or four bedroom, two-full bath, light-filled home located in the charming historic district of Easton. The residence combines modern updates with prime location and offers a low-maintenance lifestyle in the heart of this captivating town. Renovated in 2023 and thoughtfully designed to maximize space and functionality. The attention to detail is evident throughout, with stylish finishes and fixtures that perfectly complement the cozy interior. The floor plan allows for comfortable, everyday living. One of the standout features of this property is the small, private courtyard. This intimate outdoor space provides a private sanctuary where you can relax, unwind, and enjoy the outdoors. With minimal yard maintenance required, you'll have more time to savor the wonderful amenities Easton has to offer. Walking distance to an array of cultural attractions, galleries, boutique shops, and dining establishments. Schedule a private showing today. Off street parking located on N Higgins Street.

Welcome to 402 Cherry Street, a beautifully, renovated three or four bedroom, two-full bath, light-filled home located in the charming historic district of Easton. The residence combines modern updates with prime location and offers a low-maintenance lifestyle in the heart of this captivating town. Renovated in 2023 and thoughtfully designed to maximize space and functionality. The attention to detail is evident throughout, with stylish finishes and fixtures that perfectly complement the cozy interior. The floor plan allows for comfortable, everyday living. One of the standout features of this property is the small, private courtyard. This intimate outdoor space provides a private sanctuary where you can relax, unwind, and enjoy the outdoors. With minimal yard maintenance required, you'll have more time to savor the wonderful amenities Easton has to offer. Walking distance to an array of cultural attractions, galleries, boutique shops, and dining establishments. Schedule a private showing today. Off street parking located on N Higgins Street.

402 Cherry St, Easton

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

$479,000

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.

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: (410) 745-0415

$1,985,000

Welcome to "Mostly Porches" an exceptional coastal retreat with captivating views of the harbor, perfectly situated on a spacious .41 acre corner lot just around the corner from the shops and restaurants of St. Michaels. Built in 2018 with virtually maintenance-free construction, this beautifully designed home offers the ideal blend of comfort, style, and convenience in a rare St. Michaels setting. Inside the floor plan is filled with an abundance of natural light and enhanced by soaring cathedral ceilings, creating an airy and inviting atmosphere ideal for both every day living and perfect for entertaining. The main living area incorporates the living, dining and kitchen and offers easy access to the extensive porches the home features, including the screened-in porch with a gas fireplace and views of the harbor. In the great room there is also a "hidden" pantry along the dining area wall with plenty of shelving and storage. Custom built-in bookcases line the living area wall to the left of the propane fireplace which incorporates a built-in 90 lb per day nugget ice-maker. The gourmet kitchen is centered around a large island and features SS Thermador appliances including a duel fuel range with a six burner gas cooktop and electric oven, and an under counter wine fridge and under counter beverage fridge in the island. The contemporary design features the primary suite, 2nd bedroom, office/den, full bath and utility closet all on the main level. A standout out feature of this property is the 2nd level private guest suite, which is a licensed income-producing vacation rental, offering flexibility for guest or the opportunity for supplemental income. This private enclave includes a small sitting area, private bath and kitchenette with under counter refrigerator drawer, under counter freezer drawer, Keurig coffee maker, counter top microwave, and free standing shelves. The property also includes an attached 2 car garage, fire pit, raised garden beds with drip irrigation, and full irrigation system in the yard plus an oversized attached 2 car garage. With its desirable location close to all St. Michaels has to offer, exceptional amenities, and low-maintenance design, this is a rare opportunity to own one of the town's newer build homes with water views and income producing opportunity.

Welcome to "Mostly Porches" an exceptional coastal retreat with captivating views of the harbor, perfectly situated on a spacious .41 acre corner lot just around the corner from the shops and restaurants of St. Michaels. Built in 2018 with virtually maintenance-free construction, this beautifully designed home offers the ideal blend of comfort, style, and convenience in a rare St. Michaels setting. Inside the floor plan is filled with an abundance of natural light and enhanced by soaring cathedral ceilings, creating an airy and inviting atmosphere ideal for both every day living and perfect for entertaining. The main living area incorporates the living, dining and kitchen and offers easy access to the extensive porches the home features, including the screened-in porch with a gas fireplace and views of the harbor. In the great room there is also a "hidden" pantry along the dining area wall with plenty of shelving and storage. Custom built-in bookcases line the living area wall to the left of the propane fireplace which incorporates a built-in 90 lb per day nugget ice-maker. The gourmet kitchen is centered around a large island and features SS Thermador appliances including a duel fuel range with a six burner gas cooktop and electric oven, and an under counter wine fridge and under counter beverage fridge in the island. The contemporary design features the primary suite, 2nd bedroom, office/den, full bath and utility closet all on the main level. A standout out feature of this property is the 2nd level private guest suite, which is a licensed income-producing vacation rental, offering flexibility for guest or the opportunity for supplemental income. This private enclave includes a small sitting area, private bath and kitchenette with under counter refrigerator drawer, under counter freezer drawer, Keurig coffee maker, counter top microwave, and free standing shelves. The property also includes an attached 2 car garage, fire pit, raised garden beds with drip irrigation, and full irrigation system in the yard plus an oversized attached 2 car garage. With its desirable location close to all St. Michaels has to offer, exceptional amenities, and low-maintenance design, this is a rare opportunity to own one of the town's newer build homes with water views and income producing opportunity.

303 Manor, Saint Michaels

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

$511,550

Beautiful home offering 4 generous bedrooms with 2 baths featuring new commercial grade LVP flooring throughout the main floor, custom kitchen cabinets with pantry, automatic under counter lighting, slow close cabinets, luxury tile in bathroom and laundry room, all new stainless steel appliances, custom walk-in shower with bench, new vanity, and multiple shower heads. Second bathroom has been renovated completely to feature a deep soaking tub, with new upgraded hot water tank to soak for hours. Additionally all new upgraded HVAC ductwork and with an additional dampening system which allows your garage to have AC/heat. Freshly painted interior tops it off. Outside there is a fenced yard with an extended patio with a 10 x 13 hard topped gazebo, raised garden beds, fire pit, and a large shed to give you the perfect outdoor oasis with outdoor lighting so the celebrations can continue into the night.This is a must see home on a quiet street in a well desired school district. Square footage is larger than tax record and Seller to find home of choice

4 Beds ⋅ 2 Baths

Beautiful home offering 4 generous bedrooms with 2 baths featuring new commercial grade LVP flooring throughout the main floor, custom kitchen cabinets with pantry, automatic under counter lighting, slow close cabinets, luxury tile in bathroom and laundry room, all new stainless steel appliances, custom walk-in shower with bench, new vanity, and multiple shower heads. Second bathroom has been renovated completely to feature a deep soaking tub, with new upgraded hot water tank to soak for hours. Additionally all new upgraded HVAC ductwork and with an additional dampening system which allows your garage to have AC/heat. Freshly painted interior tops it off. Outside there is a fenced yard with an extended patio with a 10 x 13 hard topped gazebo, raised garden beds, fire pit, and a large shed to give you the perfect outdoor oasis with outdoor lighting so the celebrations can continue into the night.This is a must see home on a quiet street in a well desired school district. Square footage is larger than tax record and Seller to find home of choice

3853 Rumsey Dr, Trappe

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

$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.

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 Neck, Saint Michaels

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

$276,995

Conveniently located between Route 50 and historic downtown Easton, this charming 1950s cottage is being sold as and presents a fantastic opportunity for homeowners and investors alike. Set back from the street with a large, private backyard, the home offers timeless character and original details throughout. The first floor features a welcoming living room with hardwood floors and arched doorways, adding warmth and classic appeal. A nicely sized kitchen opens to the dining room, where sliding glass doors lead to the porch for easy indoor-outdoor living. Two spacious bedrooms and a full bath complete the main level. Upstairs, the second floor offers a generous primary bedroom with a full bath, creating a private retreat. This property is also an investor’s dream, having served as a profitable rental for many years with the potential to continue as such. With its flexible layout, it may also offer the possibility of conversion into a two-family property, with the second-floor functioning as a studio and the first floor as a two-bedroom unit. Owner will offer settlement assistance.

Conveniently located between Route 50 and historic downtown Easton, this charming 1950s cottage is being sold as and presents a fantastic opportunity for homeowners and investors alike. Set back from the street with a large, private backyard, the home offers timeless character and original details throughout. The first floor features a welcoming living room with hardwood floors and arched doorways, adding warmth and classic appeal. A nicely sized kitchen opens to the dining room, where sliding glass doors lead to the porch for easy indoor-outdoor living. Two spacious bedrooms and a full bath complete the main level. Upstairs, the second floor offers a generous primary bedroom with a full bath, creating a private retreat. This property is also an investor’s dream, having served as a profitable rental for many years with the potential to continue as such. With its flexible layout, it may also offer the possibility of conversion into a two-family property, with the second-floor functioning as a studio and the first floor as a two-bedroom unit. Owner will offer settlement assistance.

7 Judas St, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$519,000

Barely lived in totally maintenance free rancher on a 3+/- acre lot with broad water views. Freshly painted with new landscaping it is vacant and available for immediate occupancy! Main area has beautiful wood laminate flooring with carpet in all bedrooms. Bonus room to be used as an office/family room, granite counters with wine refrigerator and all nearly new appliances with utility room and washer and dryer. Located at the end of a cul de sac with mature trees and a great water view of Harris Creek and Sherwood landing. A truly unique opportunity!

Barely lived in totally maintenance free rancher on a 3+/- acre lot with broad water views. Freshly painted with new landscaping it is vacant and available for immediate occupancy! Main area has beautiful wood laminate flooring with carpet in all bedrooms. Bonus room to be used as an office/family room, granite counters with wine refrigerator and all nearly new appliances with utility room and washer and dryer. Located at the end of a cul de sac with mature trees and a great water view of Harris Creek and Sherwood landing. A truly unique opportunity!

21869 Albie Rd, Sherwood

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

$719,500

Wake up to peaceful views of Peachblossom Creek and enjoy the best of Eastern Shore living from this well-maintained 3-bedroom home in the highly sought-after Oxford Road corridor. Included is access to a private waterfront lot, providing the perfect spot to launch a kayak, fish, watch wildlife, or simply take in the beauty of the water. Designed for easy one-level living, the home offers a bright and welcoming floor plan with an open kitchen featuring a marble island, spacious walk-in pantry, and adjoining living room with a gas fireplace. A heated semi-enclosed porch creates an inviting space to enjoy creek views and outdoor living throughout the seasons. The primary suite features a large walk-in closet with custom built-ins and a well-appointed bath with a no-threshold tile shower and double-sink vanity. Additional amenities include a dedicated laundry room, partially floored attic storage, updated metal roof sections installed in 2025, and a fenced rear yard with storage shed. Just minutes from downtown Easton, shopping, the YMCA, parks, and miles of bike trails, this property offers a rare opportunity to enjoy a relaxed waterfront lifestyle without the maintenance and expense of a traditional waterfront home. Excluded : One peony plants and 2 lilies.

Wake up to peaceful views of Peachblossom Creek and enjoy the best of Eastern Shore living from this well-maintained 3-bedroom home in the highly sought-after Oxford Road corridor. Included is access to a private waterfront lot, providing the perfect spot to launch a kayak, fish, watch wildlife, or simply take in the beauty of the water. Designed for easy one-level living, the home offers a bright and welcoming floor plan with an open kitchen featuring a marble island, spacious walk-in pantry, and adjoining living room with a gas fireplace. A heated semi-enclosed porch creates an inviting space to enjoy creek views and outdoor living throughout the seasons. The primary suite features a large walk-in closet with custom built-ins and a well-appointed bath with a no-threshold tile shower and double-sink vanity. Additional amenities include a dedicated laundry room, partially floored attic storage, updated metal roof sections installed in 2025, and a fenced rear yard with storage shed. Just minutes from downtown Easton, shopping, the YMCA, parks, and miles of bike trails, this property offers a rare opportunity to enjoy a relaxed waterfront lifestyle without the maintenance and expense of a traditional waterfront home. Excluded : One peony plants and 2 lilies.

28567 Holden Rd, Easton

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

$2,149,000

NEW PRICE DO NOT MISS THIS ONE Nestled in the highly desirable Drum Point neighborhood of St. Michaels, this exceptional waterfront property offers the perfect blend of privacy, comfort, and Eastern Shore charm. Just minutes from the vibrant heart of town, you'll enjoy easy access to renowned restaurants, boutique shopping, cozy cafés, the Classic Motor Museum, and the Chesapeake Bay Maritime Museum. A former successful vacation rental, this beautifully maintained three-bedroom brick home is designed for effortless living and year-round enjoyment. The open floor plan features rich wood flooring, a striking double-sided fireplace, a renovated kitchen, updated bathrooms, and energy-efficient geothermal HVAC. Water views surround you at every turn. Relax in the shade of mature trees by the shoreline, sway in a hammock with refreshing bay breezes, or spend the day enjoying the property's outstanding outdoor amenities. Entertain guests on the spacious deck complete with an outdoor kitchen and hot tub, gather on the charming stone-walled patio, rinse off in the outdoor shower, and cool off with a swim in the pool. Boaters will appreciate the private dock offering approximately 3 feet MLW, a boat lift, and a boat launch for easy access to the water. A detached two-room studio with a covered porch provides additional flexible space for guests, hobbies, or a private retreat while enjoying spectacular water views. Additional highlights include an encapsulated crawl space and numerous upgrades throughout. This is Eastern Shore living at its finest—a rare opportunity to own a waterfront sanctuary in one of St. Michaels' most sought-after locations.T MICHAELS TUCKED AWAY ON DESIRABLE DRUM POINT NEIGHBORHOOD, MINUTES FROM THE

NEW PRICE DO NOT MISS THIS ONE Nestled in the highly desirable Drum Point neighborhood of St. Michaels, this exceptional waterfront property offers the perfect blend of privacy, comfort, and Eastern Shore charm. Just minutes from the vibrant heart of town, you'll enjoy easy access to renowned restaurants, boutique shopping, cozy cafés, the Classic Motor Museum, and the Chesapeake Bay Maritime Museum. A former successful vacation rental, this beautifully maintained three-bedroom brick home is designed for effortless living and year-round enjoyment. The open floor plan features rich wood flooring, a striking double-sided fireplace, a renovated kitchen, updated bathrooms, and energy-efficient geothermal HVAC. Water views surround you at every turn. Relax in the shade of mature trees by the shoreline, sway in a hammock with refreshing bay breezes, or spend the day enjoying the property's outstanding outdoor amenities. Entertain guests on the spacious deck complete with an outdoor kitchen and hot tub, gather on the charming stone-walled patio, rinse off in the outdoor shower, and cool off with a swim in the pool. Boaters will appreciate the private dock offering approximately 3 feet MLW, a boat lift, and a boat launch for easy access to the water. A detached two-room studio with a covered porch provides additional flexible space for guests, hobbies, or a private retreat while enjoying spectacular water views. Additional highlights include an encapsulated crawl space and numerous upgrades throughout. This is Eastern Shore living at its finest—a rare opportunity to own a waterfront sanctuary in one of St. Michaels' most sought-after locations.T MICHAELS TUCKED AWAY ON DESIRABLE DRUM POINT NEIGHBORHOOD, MINUTES FROM THE

7149 Drum Point, Saint Michaels

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

$1,195,000

Enjoy historic in-town living in the heart of St. Michaels, where this beautifully maintained residence offers a rare combination of timeless architecture, a sought-after waterfront-adjacent location, and convenient access to the harbor, parks, trails, shops, and restaurants. Ideally located near the waterfront, scenic trails, park, kayak launch, and the town’s many amenities, the home provides easy access to the best of Eastern Shore living. Inside, warm and inviting interiors feature hardwood floors throughout, multiple living areas, and four wood-burning fireplaces that enhance the home’s historic character. The flexible floor plan includes four bedrooms, four and one-half baths, a dedicated office, custom built-ins, and generous storage, well-suited for a variety of living arrangements and lifestyle needs. Thoughtfully designed spaces offer both comfortable everyday living and additional room for guests, creative pursuits, work-from-home flexibility, or future customization. Outdoor features include a landscaped fenced yard designed for privacy and low-maintenance enjoyment, along with a spacious patio ideal for outdoor entertaining and relaxation. A detached cottage provides added versatility for use as a studio, workshop, or storage space. Off-street parking is an added convenience within the Historic District. Blending historic charm, adaptable living spaces, and an exceptional in-town location, this distinctive residence offers a unique opportunity to experience life in one of Maryland’s most desirable waterfront communities.

4 Beds ⋅ 5 Baths

Enjoy historic in-town living in the heart of St. Michaels, where this beautifully maintained residence offers a rare combination of timeless architecture, a sought-after waterfront-adjacent location, and convenient access to the harbor, parks, trails, shops, and restaurants. Ideally located near the waterfront, scenic trails, park, kayak launch, and the town’s many amenities, the home provides easy access to the best of Eastern Shore living. Inside, warm and inviting interiors feature hardwood floors throughout, multiple living areas, and four wood-burning fireplaces that enhance the home’s historic character. The flexible floor plan includes four bedrooms, four and one-half baths, a dedicated office, custom built-ins, and generous storage, well-suited for a variety of living arrangements and lifestyle needs. Thoughtfully designed spaces offer both comfortable everyday living and additional room for guests, creative pursuits, work-from-home flexibility, or future customization. Outdoor features include a landscaped fenced yard designed for privacy and low-maintenance enjoyment, along with a spacious patio ideal for outdoor entertaining and relaxation. A detached cottage provides added versatility for use as a studio, workshop, or storage space. Off-street parking is an added convenience within the Historic District. Blending historic charm, adaptable living spaces, and an exceptional in-town location, this distinctive residence offers a unique opportunity to experience life in one of Maryland’s most desirable waterfront communities.

114 W Chestnut St, Saint Michaels

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

$475,000

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.