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3 Beds 4 Baths
This Cooke's Hope gem in the Springfield section truly sounds like a haven of luxury and tranquility. The generous Primary bedroom and bath, complete with a walkout to a large deck, offer a private retreat with those breathtaking Peachblossom Creek views. The spa-like setting in the primary bath, featuring an open shower and volcanic ash soaking tub, adds a touch of indulgence to everyday life. The other bedrooms, spacious and thoughtfully designed, provide comfort and convenience. The kitchen, a culinary haven equipped with top-notch appliances like Wolf, Sub Zero and Cove transforms cooking into a joyous experience, making every meal a delight. The upstairs office, with its separate entrance and expansive deck, is more than a workspace—it's a personal sanctuary overlooking the serene waters. The offer of a boat slip at the community pier opens up a world of aquatic adventures, and the prospect of a waterside pool with permits in hand promises relaxation and enjoyment under the sun. This home seems to effortlessly blend comfort and elegance, creating a dreamy retreat where every detail is a testament to a life well-lived. If homes could write poetry, this one would be a sonnet to Southern living. The list of recent improvements are too many to list, but they are available upon request. Waterside pool permit in hand. Boat slip for 2024 season is #15

6830 Cookes Hope Rd, Easton

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

7 Beds 6 Baths
Welcome to your dream waterfront retreat! ​This custom-built masterpiece is a true gem, ​boasting unparalleled elegance and ​luxurious features. With 7 bedrooms and 5.5 ​bathrooms, this residence offers the perfect ​blend of comfort and sophistication. As you step inside, you'll be greeted by ​ample natural light that floods through the ​large windows, creating a warm and inviting ​atmosphere throughout the home. The ​cathedral-ceiling dining and living rooms add ​an extra touch of grandeur, providing a ​spacious and airy feel that is perfect for ​both entertaining and everyday living. First floor primary suite with water views, custom walk-in closet, and a luxurious bath with heated floors, ​double vanities, relaxing jetted tub and beautifully tiled steam shower. The hardwood flooring adds a ​timeless and classic touch to the interior, complementing the high-end finishes and attention to detail that ​is evident in every corner of the home. The gourmet kitchen is a chef's delight, featuring stainless steel ​appliances and custom cabinetry. For those who appreciate the finer things in life, this property also includes a detached 3-car garage with ​a 2-bedroom guest apartment, offering versatility and additional space for hosting friends and family. ​Imagine the convenience and luxury of having a separate space for guests to enjoy their privacy. Step ​outside, and you'll discover the guest cottage, a charming retreat overlooking the serene waterfront. ​With its own unique character, this cottage provides an ideal spot for guests or even a private home ​office. The waterfront experience is taken to the next level with 250'+/- of rip-rapped shoreline, a private pier ​and boat lift. Whether you're an avid boater or simply enjoy the tranquil views of the water, this property ​offers the perfect setting to savor the beauty of waterfront living. Spend your days basking in the sun on ​your waterside deck, relaxing in your Swimspa, fishing off the pier, or taking a boat ride to explore the ​nearby waterways. Immerse yourself in the beauty of nature and create lasting memories in a home that ​truly reflects your discerning taste. Don't miss the opportunity to make this gorgeous waterfront property ​your own!

24756 Rays Point Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665

5 Beds 8 Baths
This offering is a once in a lifetime opportunity! The 8,000 square foot (160,000 cubic feet volume) contemporary masterpiece is a magnificent collaboration between a prominent structural engineer, whose works include the world's tallest building Partronas Towers in Malaysia and a renowned New York architect, whose works include Filene Center at Wolf Trap Farm Park, in McLean Virginia and Mann Music Center in Fairmont Park, Philadelphia. The house with 300 windows, bi-level in-ground pool and spa sit majestically on the 8.5 lot with 8 feet MLW water depth at the dock. Solar panels in the field contribute to making this property's operating expenses incredibly affordable. There is room and already designated space for an elevator if so desired. Primary bedroom suite is on the main level. This spectacular Miles River waterfront oasis is minutes to both Easton and St. Michaels. This offering does not include the adjacent lot.

10205 Kintore Dr, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 673-3344

3 Beds 2 Baths
This beautiful rancher is located in the serene Royal Oak community of Talbot County, Maryland. The house is situated on a spacious 2-acre lot, providing ample space for outdoor activities and relaxation. The property is surrounded by lush greenery, which provides a sense of privacy and seclusion. The house itself is a roomy 3-bedroom rancher, perfect for families or those who enjoy having extra space. The interior is bright and airy, with plenty of natural light streaming in through the windows. The Great room is spacious and inviting, with a cozy fireplace that’s perfect for chilly evenings. The kitchen is modern and well-equipped, with plenty of counter space and storage. The house has 3 bedrooms, each of which is comfortable and well-appointed. The master bedroom is particularly spacious, with plenty of room for a king-sized bed and additional furniture. The bathrooms are modern and well-maintained, with all the amenities you need to feel comfortable and relaxed. The house is located on a cleared part of the lot, which is obscured from the road. This provides a sense of privacy and seclusion, making it the perfect place to relax and unwind. The Royal Oak community is known for its peaceful and tranquil atmosphere, making it the perfect place to call home.

6893 Hopkins Neck Rd, Easton

Listing courtesy of Real Estate Professionals, Inc.. Contact:

5 Beds 3 Baths
Welcome to this spacious 5-bedroom, 3-full bath Cape Cod home, boasting over 3,000 square feet of living space. Conveniently located to downtown Easton and Rte 50, this property sits on a generous two-acre lot, providing ample space and privacy. This well-maintained home has seen many updates, ensuring modern comfort and style. The family room features a cozy gas fireplace and built-ins, perfect for those chilly evenings. The spacious eat-in kitchen is an entertainer's dream, offering a great space for hosting gatherings. Step outside, and you'll discover a deck that offers a tranquil space for relaxation. Beyond the deck lies an inviting inground pool, creating the ideal setting for enjoying hot summer nights and outdoor activities. The expansive backyard, spanning two acres, is perfect for entertaining, and there's also a fenced-in area, providing a safe space for your four-legged companions. With its generous living space, modern amenities, and convenient location, this Cape Cod home is a true gem that combines comfort, functionality, and outdoor enjoyment. Don't miss the opportunity to make this property your own.

29880 Milby Dr, Easton

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

2 Beds 2 Baths
WYE CLIFF : Sited on 13.5 spectacular and elevated acres overlooking the Wye River, this iconic property boasts commanding and breathtaking views of Wye Island, and is truly one of the best points of land in Talbot County! Magnificent trees and a beautiful drive-in add to the beauty of this extraordinary estate . Included is a stunning (completely renovated)2 BR guest cottage with screened porch and deck, large resurfaced gunite pool with travertine decking (and existing pool house structure),and expansive new composite dock, 24,000 lb lift, MLW 6'. The center -aisle stable has 5-8 stalls with the caretaker's apartment above, a wash stall, tack room, and several pastures all with river views. The 2nd barn has a well-equipped workshop, 3 garage bays, and large storage area. In addition, the current owner put in geothermal, a new well, new cedar shake roofs on both barns, and a living shoreline by the pier. A chipping/putting area and base for Har-Tru tennis court is also on property. Two additional waterfront lots which are adjacent to the main drive can also be purchased for an additional $1,800,000. Lot 1 consists of 47+/- acres and Lot 2 is 58+/- acres and both are currently farmed. Buyer to confirm water depth and pay any fees related to agriculture tax and forest conservation/management program. SDA's were established in 2010 so buyer would need to go through county to reassess and permit. Call listing agent for more information. Driveway is owned and right-of way granted to neighbor (there is a road maintenance agreement). PLEASE DO NOT DRIVE DOWN THE DRIVEWAY WITHOUT AN APPOINTMENT as there are security cameras. All showings must go through listing agent.

26992 Presquile Rd, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 673-3344

4 Beds 5 Baths
Rare opportunity to acquire a well-appointed home with immense views and convenient proximity to St Michaels. Ideally located by land and sea in Chance Hope Farm on the Miles River at the confluence of Eastern Bay, this stunning, classic eastern shore brick colonial has everything the most decerning buyer needs. This Daffin custom-built home features a generous, main-level primary suite featuring a spa-like bath with heated floors, a large soaking tub and separate shower, and two walk-in closets. The kitchen is a chef’s dream, featuring high-end stainless-steel appliances, a wine cooler, a warming drawer, and a massive island. There are also formal living and dining rooms, two office spaces, a recreation room, and a river room that enjoys views of Eastern Bay and beyond. The park-like lot has 220+/- feet of rip-rapped shoreline, a private pier with 3’ of MLW, lush landscaping, and a waterside deck with an outdoor kitchen.

24678 New Post Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665

3 Beds 4 Baths
Turn Key and Move in Ready with a Price IMPROVEMENT! Inspired by the architecture of Colonial Williamsburg, this custom-built home has classic features with modern amenities. This home is traditional and timeless, with large six by six windows, and wide planked pine flooring, recycled from old beams. In the family room, you can center your entertaining around the custom 48" wide Rumford fireplace, adorned with hand made brick and a heavy Walnut mantle. Guest will appreciate the appointed center front portico and lighted brick walkway. Dormer windows on the upper floors not only add character but also bring in lots of natural light. The peninsula styled kitchen has ample storage with Hickory cabinets, granite countertops, luxury tile and new appliances, including a gas Viking Range, Bosch dishwasher and 36" Kitchen Aid Refrigerator. The primary bedroom has one walk in closet, and one oversized closet, both with custom closet design. The primary bathroom has double sinks, granite countertops, a separate "make up" vanity, a large custom tiled walk-in shower. Second bedroom and full hallway bathroom on the main floor. Large foyer with 48" wide staircase leads to upstairs third bedroom and full bath. And an open large, finished studio which can be used for a home office, game or craft room or can be converted to other bedrooms. Large walk-in storage over the garage is easily accessible as well as ample attic storage. You have two private acres to enjoy, surrounded by mature trees and lots of wildlife; turkeys, deer fox and more. A large, raised vegetable garden plot is ready for your green thumb. If you have a home business or hobby requiring storage and workspace for your equipment; historic vehicles, boats, restoration of any have a large pole building with lean-to. The location of this home is ideal for commuters, 30 miles to Annapolis and 6 miles to Easton. This home has a list of recent upgrades including a new roof in Sept 2023, new Bryant HVAC in 2023 and 2014 (upstairs and downstairs), Rinnai tankless water heater 2015, fresh interior and exterior paint. Photos, videos, floor plan and 3D Tour is available.

29119 Rabbit Hill Rd, Easton

Listing courtesy of . Contact: (410) 251-5291

3 Beds 2 Baths
PRICE ADJUSTMENT Looking for a peaceful getaway to escape the hustle and bustle? This is it. Almost 5 private acres with deep water on Bolingbroke Creek facing a pristine conservation area. Ideal for stargazing. The peaceful surroundings and tranquil sounds of the water create a serene atmosphere. Enjoy the breathtaking views from the dock with boat lift and from the many outdoor entertaining spaces. The beautiful waterside deck with hot tub is the perfect setting for relaxation and enjoying the beauty of nature and surrounding waterviews. This lovely property sits up on high ground so no need to worry about flood insurance. Spend your days fishing, crabbing, kayaking, boating or simply taking in the scenic views. Plenty of yard space for pets and family gatherings. This Acorn contemporary home has lots of natural light and hardwood floors. The large windows and sliding glass doors not only bring in ample light but also provide stunning views of the water. There are 2 gas fireplaces,and the primary bedroom has its own deck facing the water. Much of the shoreline is protected. Easy boating to the the Hyatt and restaurants in Cambridge, great fishing in the Choptank River. Upgrades include a new dock decking, newer heat pump, newer Anderson energy efficient windows, on demand Rennai hot water heater, encapsulated crawlspace, vinyl siding over cedar siding for easy maintenance, new washer and dryer. This home has been extremely well maintained and ensures a high level of quality and care ! This is the eastern shore of Maryland at its finest. One year home warranty included. High speed fiber optic cable for internet.

30448 Belmont Dr, Trappe

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

5 Beds 9 Baths
Welcome to Sunnyside, an exceptional and rare waterfront estate situated on a spectacular 16-acre point along the majestic Miles River. A picturesque, winding driveway leads to the one-of-a-kind contemporary home, built by A. James Clark for his family. Completed in 1978, Sunnyside was the culmination of a 3-year collaboration between the legendary builder and philanthropist, his son, architect Paul Clark, and prominent DC architect, John Henry Sullivan. Mr. Clark hand-picked every remarkable detail on the property, from the materials to the craftsmen, many of whom would later join him to form the iconic Clark Construction. Meticulously maintained over the years, the main house features floor-to-ceiling windows throughout offering stunning water views from every room. The thoughtfully designed layout of the main level easily accommodates both large and intimate gatherings. Highlights include a striking 24ft x 24ft sun-drenched atrium, an expansive main level primary bedroom suite complete with its own fitness room and sauna, 4 fireplaces, a living room with 20ft+ tall ceilings, a greenhouse, and a temperature-controlled wine room. The Great Room, the perfect spot for a casual gathering with friends and family, boasts striking custom woodwork throughout and incredible expansive western views of the property. The second-floor features three bright and sunny bedrooms, each with their own private bathroom, balcony, fireplace, heating systems, and distinctive views of the Miles River. The portico along the front of the home leads to an easily accessible, but completely private guest house with its own cozy living room, bedroom, full bath, fireplace, and kitchenette. Just outside the main house with idyllic garden and river views is the pool with its own full bath. The tennis court, livestock barn, and equipment barn are just a short stroll through the carefully designed and bucolic landscape. Resting on a point on the Miles River, Sunnyside boasts approximately 2000ft of waterfrontage, of which approximately 1550ft is riprapped. A 135ft deep-water pier (3ft MLW) offers 2 boat lifts. Less than 10 minutes to Downtown Easton and just a short boat ride (or less than 15 minutes by car) to St. Michaels, legendary Sunnyside proudly sits at the heart of Maryland’s Eastern Shore.

26919 Miles River Rd, Easton

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

3 Beds 2 Baths
8478 Jane Lowe Road, Wittman MD 21676 Located just 9 miles to St. Michaels and 8 miles to Tilghman, this three-acre waterfront retreat is improved by a renovated barn/residence and detached garage workshop. The residence has a waterside front porch opening to an open-concept kitchen and living room with a wood stove and water views. A utility/mud room with closet, formal dining, full bath, and two bedrooms compliment the first floor while the second floor provides an open family-great room with a waterside side balcony, deck, full bath, laundry, large bedroom #3, and a loft on the third floor. Mini-split heating and cooling throughout the second and third floors with HVAC on the first floor and updated three-bedroom septic system from 2017. Currently licensed with the County as a vacation rental, the property has a productive rental history.

8478 Jane Lowe Rd, Wittman

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

3 Beds 3 Baths
Looking for a waterfront lifestyle without the waterfront price...look no further. This stunning home is nestled on 2+/- acres within the waterfront community of Deep Harbour Farm with a multi-slip boat dock for community members (slips subject to availability each year) and kayak/SUP launch and storage racks. This residence offers the perfect blend of country living and modern comfort. Built in 2005, this inviting home boasts an open floor plan creating a sense of space and flow that welcomes you the moment you step inside. As you enter, the rich hardwood floors and crown molding throughout the first floor immediately catch your eye adding an elegant touch to the living spaces. The large updated kitchen boasts granite countertops, a substantial island and stainless steel appliances, creating a culinary haven for both everyday meals and entertaining. Adjacent to the kitchen, a separate dining room provides an elegant setting for formal gatherings in addition to the open everyday dining space between the kitchen and living room. Convenience meets practicality with a laundry/mudroom located off of the attached 2-car garage, complete with built-in cabinets and a pantry. The second floor presents the primary suite, offering two walk-in closets and a primary bath with an oversized soaking tub and a separate shower. Two additional bedrooms each thoughtfully designed with a walk-in closet, providing ample storage. For those seeking versatility in their space, there's a bonus/game room with an adjoining separate office, perfect for work, play, or relaxation. Outdoor living is a delight with an impressive 18'x36' in-ground saltwater pool with diving board, surrounded by a meticulously crafted hard scraped patio that features a built-in fire pit and seating and lovely landscaping—an ideal spot for summer gatherings and relaxation. Additional highlights of this property include solar panels which keep electric costs at a minimum, a detached 24'x48' insulated garage with 200-amp electric service, offering ample space for hobbies and storage. It's a place where coastal charm and modern amenities come together, making it a true gem for those seeking a water oriented lifestyle. Located within minutes to numerous public boat ramps offering access to the Chesapeake Bay and the surrounding tributaries where you can enjoy fishing, crabbing and all the Bay has to offer.

6660 Reeses Pride Rd, Sherwood

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

4 Beds 4 Baths
Prime Oxford location! Custom built four-bedroom home sited on 2.59+/- acres with water access to Boone Creek. Full of natural light, this open floor plan home has a gorgeous rocking chair style front porch and large conditioned enclosed porch, great room with gas fireplace and cathedral ceiling, gourmet style kitchen with center island and breakfast nook, formal dining room, first and second floor owner’s suites and office with French doors. Spacious walk-in pantry. Spacious laundry room with washer, dryer and utility sink on main level. Large custom designed rear patio overlooking lush grounds. Attached two car garage with bonus room above. Workshop and equipment garage. 12’ right of way to Boone Creek. New roof within the last 5 years. Room for a pool. Minutes to downtown Oxford’s restaurants and shopping.

26604 E Bonfield Rd, Oxford

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

11 Beds 17 Baths
Magnificently resplendent, captivating, and wholly irreplaceable, Cecilia’s Point is an offering unlike any other. Situated on the Chlora's Point peninsula along Maryland’s glamorous Eastern Shore, the estate boasts 3000 feet of protected shoreline and spans 117 acres. It serves as a serene contrast to urban living, affording an authentic getaway to a place of sculpted grounds and open expanses, permeated only by the gentle sounds of the Choptank River. A long, meandering driveway winds through a verdant canopy of trees, a bubbling pond and white picket fences before skimming alongside the shoreline and concluding. The motor court, with its lighted entry pillars, comprises herringbone brick pavers and presents a regal introduction to the majestic estate. Distinctly coastal yet ornate in detail, slate shingles and striped awnings meet Corinthian columns in an old-world fashion reminiscent of the most exclusive private clubs and finest inns. An upper-level terrace spans the main residence’s entire width, creating an intimate loggia underneath, bathed in the glow of the sun, old-world lanterns and magnificent sunsets. Through arched glass and mahogany double doors, the greeting hall is artfully luxurious with its checkered marble floor, sweeping wrought iron staircase, and intricate millwork. A groin vault ceilinged gallery immediately ahead extends the depth of the home. The paneled game room is a byword for quiet sophistication, warmly lit, and composed of multiple intimate game and seating areas. The kitchen, with its wooden beam ceiling, blends such traditional touches with exacting craftsmanship and more modern conveniences such as a full suite of SubZero, Wolf, and Miele appliances. At the end of the main gallery and centered on the main level is the spectacular great room. Ceiling trusses gracefully merge into the coffered ceiling above the double-height space, an etherealness accentuated by stained glass windows and panoramic water views. The four bedrooms are each up to par with the world’s leading hotel suites and finished with a distinct old-world theme. Chief amongst them is the upper-level primary suite. Uninterrupted views over the rear lawns and water from the private terrace couple with twin dressing rooms, spa bathrooms, and a massage room to constitute a hidden home within a home. A sumptuous media room, home office, fitness center, and private elevator complete the main home. An airy breezeway connects to the self-sufficient guest house. A large SubZero-Wolf kitchen, full laundry facilities, and five additional bedroom suites offer ample accommodation. A carriage house includes two additional bedroom suites. The garages can accommodate 10 vehicles. Yet, the amenities against this stunning natural backdrop are what truly sets Cecilia’s Point apart. Pickleball courts, a heated saltwater pool and hot tub with accompanying cabana, outdoor kitchen, fire pit, miles of trails, a deepwater dock with both boat and jet ski lifts, putting green, and a sandy beach all alongside glorious westerly sunset views of the Choptank River will likely never be replicated. The feel of the cabana is total relaxation with boat bar, two TV's and a full bathroom surrounded by magnificent water views that is spectacular. The estate is located near charming Downtown Easton and all of its entertainment, but feels like an entirely separate world. Unquestionably one of Maryland’s most hidden gems, Cecilia’s Point is an estate to last generations.

27189 Island Creek Rd, Trappe

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

3 Beds 3 Baths
Set on the natural bank of the Tred Avon River, this modern home utilizes white polished concrete supporting a Douglas Fir butterfly roof that celebrates the interplay of light and industrial craft. It is the first of its kind on the Chesapeake Bay and established an unprecedented environmental approach for Talbot County due to its habitat restoration and sensitivity to the site. Designed and completed with uncompromising engineering and architecture while respecting and improving the waterfront site. The brilliance in the home's presence and life is light and passive, yet its structure and materials are robust; it will outlive generations. Details include geothermal systems, radiant heated and cooled floors zoned throughout, a premium professional kitchen, and an ultra-high performance concrete rain screen. The house and amenities sit at about an 18 ft elevation above the mean high water level and offer unattainable proximity to the shore, within 100ft. A long pier with two power lifts and MLW 6+ deep water can accommodate large sailboats. The beautiful exposures from the 450ft of shoreline enjoy views of the protected conservation land of Ratcliff Manor. One may complete the cottage and pool as they wish and add another guest suite or a modern cabana. By every measure of material, exposure, amenities, elevation, nature, ecology, low-e, and robust strength, it is an incomparable home. All of this, while it lives gently, conceding to the site and surroundings, elevating the qualities of life on this protected shore.

27950 Tred Avon Dr, Easton

Listing courtesy of TTR Sothebys International Realty. Contact: (703) 714-9030

5 Beds 5 Baths
Welcome to Tilghman and come explore a place that captures all of your dreams. A place where you can take the time to walk to restaurants, fish from the back yard or sit on your porch and watch the boats parade by as the sun sets. A place where you will always come back to and your children will never want to leave. Simply put this place will feel like home....And to make this all perfect we have designed the ultimate home complete with all the modern day luxuries. Whitehall Building's 5 bedrooms and 4.5 baths TO BE BUILT NEW CONSTRUCTION presentation includes a primary suite and family room area on both first and second floor. Walls of glass and an open floor plan will allow you to flow from room to room, while providing jaw dropping views with private spaces to get away. A Chef's kitchen with a HUGE island, gourmet appliance and coffee bar leads to a large covered porch and family room. Please take note, the fireplace with beamed ceilings, quartz counters, wine fridge, spa like bathrooms, outdoor showers and too many other additional luxuries to list are all standard features. We have purposely designed the perfect home complete with all the BEST finishes and touches. Lastly, by developing a seamless process, Whitehall Building allows you to customize and incorporate all of your ideas; making this home especially yours in just minutes....and then just 12 months later this new Luxury dream home is all yours. Whether you are looking for fresh new start, second home or vacation rental, this offering will satisfy your every desire. Contact listing agent for details. Construction pictures are of the builder's previous work. Professional photos of lot to be uploaded.

Bar Neck Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact: (410) 822-6272

4 Beds 2 Baths
Located on a scenic Creek of the Gross Coate Farm just minutes to Easton. A long private driveway leads to the fifteen plus acre site with wonderful elevation and amazing views. A nature lover's paradise. This home was built and designed by Deltec Homes. Every detail of every Deltec home is intentionally designed to create a Real Connection for people and the planet. That means they engineer homes that are able to withstand even the worst of weather conditions. They create homes that exist in harmony with the natural world. The flooring on the main level is Bamboo and the upper level Brazilian Walnut. The spacious home with first floor primary bedroom suite and two additional bedrooms upstairs has an open kitchen with Hickory cabinets and a family room with gas burning fireplace, private library/offices and waterside views of Gross Creek just off of the Wye East River. There are plenty of native plantings and great opportunities for wildlife sightings. The floating dock offers a great way for launching kayaks and canoes. The home sits on a high elevation, therefore no flood insurance required. Part of the acreage is farmed by a local farmer with a contract that ends on December 31, 2023. Looking to work from home, recently equipped with fiberoptic for fast speed internet through Easton Utilities. More photos to come.

11239 Gross Coate Rd, Easton

Listing courtesy of Coldwell Banker Realty. Contact: (410) 263-8686

6 Beds 6 Baths
The Wilderness - This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 8 parcels totaling 380 acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. Surrounded by open space and preserved farmland with proximity to Oxford, Easton, Cambridge, and St. Michaels, The Wilderness is sure to please the discerning buyer. Sited among large waterfront estates, The Wilderness enjoys privacy and a commanding presence with old-growth trees, broad southerly views, and deep water. The scope of improvements includes the primary residence, waterside guest cottage, beach house, pool, pier, tennis court, early 20th-century barn, and a host of accessory structures for life on the farm. Visit the virtual tour for an inside look and appreciation for the scope of this offering. The main house has great historical significance not only for the original owner’s grandson who lived there and served two terms as the Governor of Maryland but also for its place in the development of Maryland’s domestic architecture, as noted on two markers from the Maryland Bicentennial Commission and the Maryland Historical Society. The smaller and original of the two brick wings dates from the late 18th century and the larger wing from the early 19th century. The house’s architecture is unusual in that the 19th-century wings telescope up, instead of down, from the original wing. The white brick, black shutters, and historical olive green trim color are a serene palette against the house’s majestic specimen trees around the property, including a gigantic Sycamore that is the largest of its species in Maryland. The long white gravel drive under the sheltering canopy of mature trees passes by the barn and other outbuildings then curves around the front of the house. Brick steps lead up to the front porch of the early 19th century wing opening into a gracious foyer and stair hall with an elegant elliptical arch that rests on pilasters at the side walls to separate the public from private areas of the house. A French door at the rear of the foyer frames a vista of the lawn and Choptank River. To the side of the foyer are two identical parlors at the front and rear corners of the house. Both rooms have magnificent fireplace mantles and surround; one is a 1740 hand-carved mantel by noted English artisan woodcarver Grinnling Gibbons and the other is a 1780 mantel surrounded by the famous English architect and artisan, Robert Adam. The main floor of the 18th-century wing contains a spacious living room, dining room, original kitchen, and larger kitchen, pantry, two powder rooms, and a stunning sunroom connecting to a terrace along the rear of the house overlooking the Choptank River. Part of this wing was the final addition to the original home. The second floor of the 19th-century wing contains two bedrooms over the two parlors below with fireplaces and walk-in closets and two baths. The 18th-century wing and later addition contain an artist’s studio with cabinetry and sink that has a myriad uses-family TV room, arts and crafts room. The primary suite is located at the rear corner of this wing. It has a fireplace flanked by single windows and another window on the rear wall for panoramic views of the mature landscape and the Choptank River. Two baths complete the suite, with one bath off a hall for access from the art studio. Two stairs access the attic level; one in the 18th-century wing leads to two bedrooms and one bath. The main stair in the 19th-century wing leads to a large game room and another cozy bedroom ensuite..... please see the property website for the complete description, additional virtual tours, and resources.

27293 Southside Island Creek Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

4 Beds 4 Baths
Experience luxury living on this picturesque 2-acre estate nestled along the tranquil shores of Irish Creek, a tributary of the Choptank River. Pride of ownership is evident in this meticulously maintained Colonial with exquisite fixtures and finishes found throughout the house. Prepare culinary delights in the Chef’s kitchen, where functionality meets style, catering to even the most discerning foodie. The large island with seating for 7, and the separate dining room, family room, and formal living room offer options for entertaining guests. On the main level, you will also find a bedroom with direct access to a full bathroom. Retreat upstairs to the opulent primary suite, featuring a spa-inspired bathroom complete with a generously sized separate shower, luxurious soaking tub, and elegant dual vanity. Upstairs, you will also find two guest bedrooms, a hall bathroom, and a conveniently located laundry closet. The conditioned 2-car garage offers ample space to create a waterside fitness room or office to suit your lifestyle. Above the garage, you will find a versatile finished space that can be tailored to your specific needs. Enjoy the outdoors by relaxing on the covered front porch, the screened-in back porch, or by taking a dip in the pool. The private dock is equipped with a boat lift, water, and electric, and offers approximately 3.5 feet MLW. Other features of the property include 300 feet of riprapped shoreline, brick walkways, waterside lawn irrigation, and landscape lighting. Royal Oak is located between Easton and St. Michaels and is just 1.5 hours from D.C. and Baltimore, 2 hours from Philadelphia, and just minutes from fine dining, shopping, healthcare, theatres, galleries, museums, golf courses, a country club, a yacht club, and a jet airport.

5503 Gunners Range Rd, Royal Oak

Listing courtesy of Meredith Fine Properties. Contact: (410) 822-6272

4 Beds 4 Baths
Welcome to Irish exquisite waterfront retreat nestled on Irish Creek off of the Choptank River and the Chesapeake Bay. This stunning one-level home boasts 4,000+ square feet of luxurious living space, designed to offer the ultimate in comfort and grace. Upon entering the home, you will be greeted by the grandeur of the water views that offer a serene oasis away from the maddening crowds. There is something to be said about the mesmerizing beauty that the Chesapeake Bay has to offer and the indisputable fact that this Talbot County waterfront home is simply sublime. The heart of this home lies within its expansive kitchen, family room and river room, where memories are made and stories are shared. The warmth of a wood-burning fireplace adds an inviting touch, creating the perfect ambiance for intimate gatherings. Adjacent to the kitchen, you will find a formal dining room, ideal for hosting elegant dinner parties, as well as the river room, perfect for casual meals with loved ones. Multiple gathering spaces and perfect flow between them provide space to entertain large gatherings of family and friends. Some of the highlights of this remarkable property are the magnificent waterside living rooms, which are spacious, yet cozy and light filled. Whether used as a private retreat or a place to entertain guests, these rooms offer a serene atmosphere and stunning views of the surrounding waterfront and landscape. The home has two large primary owner suites with water views and ample closet space. Sunsets here are surreal as the waterside faces due west. Step outside onto the waterside deck, where you can bask in the tranquility of nature and relish in the awe-inspiring sunset views over the water. The 2.78-acre lot is adorned with mature perennial gardens, adding a burst of vibrant colors and fragrances to the already breathtaking scenery. A private dock extends from the property, allowing you to embark on boating adventures or simply enjoy the calming presence of the water. For those with a passion for cars, hobbies or craftsmanship, the home features an extra-large garage and workshop, providing ample space for projects and storage. A large shed and a beautiful fenced garden complete the yard. This private and serene waterfront property is truly a haven for those seeking respite from the hustle and bustle of everyday life. Whether you are hosting lively gatherings or simply enjoying the peace and solitude with loved ones, this home offers the perfect setting. Immerse yourself in the beauty of the Chesapeake Bay and create memories that will last a lifetime in this remarkable Irish Creek retreat.

5560 Heron Point Rd, Royal Oak

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

6 Beds 9 Baths
Offered for the first time in nearly forty years, Swan Point is the quintessential Eastern Shore estate. Situated on 4.5 +/- acres, with westerly exposure on the Tred Avon River this estate has it all. Private pier with 4’+/- MLW and 400 +/- of waterfrontage. The main house is classically charming and takes full advantage of the sunset water views. Spacious kitchen is complete with high-end appliances and large center island making it perfect for large scale entertaining. Fully finished basement. Primary suite is separate and private with water views and a luxurious, spa-like bath complete with jetted tub, separate shower and marble touches. The park-like grounds include a paddock for horses and mature landscaping throughout. The estate is further improved by fabulous accessory structures including an equestrian facility, proper well-appointed guest quarters with en-suite bedroom, kitchen, living room with views over the property to the Tred Avon River and garage. There is also a one of a kind automobile museum located in the exquisite "carriage house" offering a 50x36 showroom, half bath, office and conference rooms. The four-stall stable includes, a tack room, office and abundant storage.

27473 Westpoint Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665

3 Beds 5 Baths
Stunning Waterfront Estate on the Miles River. This property has been immaculately maintained. The original home was built in 1927 but was completely renovated in 1999 and has since gone through many updates. The 3-bedroom, 3 full bath, 2 half bath, main house has beautiful hardwood floors throughout, crown moldings, exposed beams, and wood-burning fireplaces. The most discerning chef will find everything they need in the gourmet kitchen including a huge island that seats 7, a Wolf 4-burner gas cooktop with French burner, a Wolf double wall oven, a Miele French door refrigerator/freezer, two dishwashers, 2 farm sinks, and a prep sink. Enjoy meals in your casual dining area with wood-burning fireplace or formal dining room, both with easy access to wet bars, great for entertaining. A sunk-in seating area with brick floors provides French door access to a patio with a spa. The formal living room includes a wood-burning fireplace with sliders to a covered brick patio. The main house is equipped with geothermal HVAC and a whole-house reverse osmosis system, an unfinished basement, and a new roof was installed in 2023. Upstairs you will find a loft that provides the perfect spot for an office nook, a laundry room, 3 ensuite bedrooms, and a den. The primary suite includes a wood-burning fireplace, sitting area with built-ins, and sliders to a private balcony. The primary bath includes 2 walk-in closets, one with a vanity, 2 showers, 2 water closets, a double sink, and a soaking jet tub. The second guest bedroom is large enough to be another primary suite and includes built-ins, a wood-burning fireplace, a walk-in closet, a slider to a roof-top deck, and a private bath. The third guest bedroom is off a large den and has built-ins, a walk-in closet, private bathroom, and a ladder to a loft area. This second level can be accessed from two separate staircases. Another set of stairs leads to a third-level observation tower. Outside you will find extensive landscaping and hardscaping including beautiful slate walkways and mature trees with uplighting. The property boasts a dock equipped with a boat lift, as well as access to water and electricity, and a riprapped shoreline. A small cottage on the edge of the point provides stunning views, a living room with a gas fireplace, a mini kitchen, and a full bath. The one-car detached garage has a large bonus room above and tons of storage. There is also a 2-bay detached machine garage with storage on the property. The barn, which was converted to a caretaker’s cottage in 2007, has an inverted layout that has 2 ensuite bedrooms on the main level, and a living room with a slider to a balcony, kitchen, and powder room on the second level. The guest house, brand new in 2022, features a large living room, dining area, kitchen, office, laundry room, and 2 ensuite bedrooms. An in-ground pool and a gazebo with a wood-burning fireplace provide the perfect spots to entertain guests. This property has it all! Easton, Maryland, known as the New Hamptons of the Chesapeake Bay by Forbes Magazine, is conveniently located 1.5 hours from D.C. and Baltimore, and 2 hours from Philadelphia. Just minutes from fine dining, shopping, healthcare, theatres, galleries, museums, golf courses, a country club, a yacht club, and a jet airport.

27640 Villa Rd, Easton

Listing courtesy of Meredith Fine Properties. Contact: (410) 822-6272

5 Beds 6 Baths
Birthplace and home of General Perry Benson, a Captain in the Revolutionary War, and Major General in the War of 1812, Wheatlands is a significant, Historic estate on the Miles River of Talbot County. The primary structure, a stately 5 bedroom, 5.5 bath, Colonial, is sited on almost 25 acres along with an Historic barn with office, powder room, and den, a 2 bedroom, 2.5 bath guest house, a heated, waterside pool, a 1 bath pool house with temperature and humidity-controlled wine cellar, a 1 bath recreation house, a potting shed, and a hen house. A separate parcel of almost 16 acres provides additional privacy and agricultural land. The property has been substantially renovated and boasts fine craftsmanship, finishes, and fixtures. Outside you will find over 800 feet of riprapped shoreline, formal gardens, a deep-water dock with boat lift, an outdoor shower, a floating dock, and a highly coveted boat house with boat lift and second-level deck, a prime spot for entertaining. Other property features include a generator, hardwood floors, beamed ceilings, a sauna, steam showers, theatre room, an abundance of fireplaces, lawn irrigation, a paved, circular driveway, and brick and slate patios and walkways. Easton, Maryland, known as the New Hamptons of the Chesapeake Bay by Forbes Magazine, is conveniently located 1.5 hours from D.C. and Baltimore, and 2 hours from Philadelphia. Wheatlands is 5 miles from Downtown Easton and just minutes from fine dining, shopping, healthcare, theatres, galleries, museums, golf courses, a country club, a yacht club, and a jet airport. Exclusions and a right-of-way apply.

8588 Wheatlands Rd, Easton

Listing courtesy of Meredith Fine Properties. Contact: (410) 822-6272

5 Beds 6 Baths
Major reduction ! Discover this Oxford jewel where refined luxury blends effortlessly with laid-back coastal charm. Accessible from beyond twenty high-elevation acres and a stately gas-lamp flanked gate, be transported as covered walkways, cobblestone paths, ornamental trees, scenic gardens, and panoramic point of land views enchant. Here, Widgeon Point's original 1938 construction has been beautifully reimagined by skilled artisans and a talented architects designing a warmly-hued residence echoing a River House of timeless elegance. In the home’s heart, sun-filled ceilings highlight intricate millwork, artfully laid hardwoods, heated Tennessee stone floors, built-in cabinetry, and fireplaces of fine craftsmanship where you’ll work, unwind, and dine. In the provincial kitchen, professional-grade appliances, farmhouse sink, and granite-topped counters assist with best-loved meals, while adjacent firelight warms cheerful late night moments with friends. While the dining room’s wet bar serves holiday celebrations, the bar-hosted enclosed gazebo and endless outdoor patios allow for large parties and simple summer pleasures overlooking yachts and memorable sunsets. Picnic or take morning strolls to either of your private ponds, float the summer away in the saltwater pool, tend to chores from within the solar paneled barn, or launch cruises from the deep water lift-fitted dock. After a day of cruising or antiquing in town, retreat to four bedrooms; each guest-perfect with access to the grounds, privacy, and bathrooms of hand selected stone. While the primary refuge boasts one of many serene custom closets, your guests will appreciate the two bedroom guest house, and fully independent over-garage apartment. While on tour, visit the pool house’s kitchen plus bath, caretaker cottage, boathouse, three car garage, and two barns with varying fittings including geothermal HVAC and insulation. Minutes away, historic townships - including Oxford and Easton - offer friendly eateries, romantic restaurants, golf clubs, artful shops, and annual festivals, while coves, rivers, and sanctuaries inspire your inner fisherman, sportsman, or athlete with endless watershed adventure. The detailed list with all amenities uploaded in documents.

5808 Widgeon Point Ln, Oxford

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

8 Beds 6 Baths
The perfect Eastern Shore escape from the rest of the world. Situated on Glebe Creek with 12.7 acres of well-planned outdoor amenities including approximately 1,300' bulk-headed shoreline, private pier with electricity, hot & cold water, two 10,000 lb boat lifts, 2 jet ski lifts, and floating docks. Upon arrival to the gated entry, your stresses of the day melt away as you drive across the wisteria bridge over the 2 acre pond to this stately brick home. Entering the home you will notice the extensive heart pine wood floors and custom millwork. Expansive kitchen with wide water view perfect for large scale entertaining, a massive island, 2 G.E. Monogram refrigerators, 2 Wolf microwaves, 2 Wolf ovens, 2 Wolf warming drawers, a Wolf six-burner range/oven with French cooktop, 2 cooper farmhouse sinks and Brazilian Quartzite countertops. Five gas-controlled fireplaces can be found throughout the home. The elevator gets you from the first to the third floor with ease and is custom painted by renowned Smithsonian artist. The property boasts many places to relax including brick patios and paths, 2 Vicenza stone gazebos and 3 cast iron gazebos throughout property. Family and friends will enjoy the many places to play including the sports court, and the 75 yard, par 3 artificial green with sand trap, the football/lacrosse field, 50'x20' heated in-ground pool with diving board, 40' x 60' playground with playhouse, Large raised-bed colonial vegetable garden with irrigation, numerous outbuildings and 3-car garage leading to a conditioned wine room.

8831 Quailsar Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665