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$19,995,000
6 Beds ⋅ 12 Baths
Nestled along the picturesque Tred Avon River, this extraordinary estate comprises two expansive waterfront parcels totaling 11 acres. A masterpiece of luxury living, the centerpiece is a magnificent 3-level palatial brick home with 6 bedrooms, 7 full baths, 5 half baths, and 7 gas fireplaces set on nearly 7 acres, complemented by an adjoining 4-acre vacant lot. Enjoy the private dock boasting approximately 3 feet of mean low water (MLW), complete with 2 boat lifts, 4 jet ski lifts, and a floating pier to launch your kayaks. The residence is a grand architectural marvel featuring a 2,300+ square foot primary suite with sitting room, breakfast bar, two bathrooms, two walk-in closets, and a spacious, private terrace. Revel in the epitome of entertainment with tons of outdoor terrace space, a built-in barbecue, an indoor pool, spa, and sauna, and a finished, daylight lower level equipped with a wine cellar, second kitchen, and built-in bar. The property is adorned with a pavered driveway, offering a stately approach to this waterfront oasis. Conveniently located between Easton and Oxford and just minutes from a country club, jet airport, theatres, fine dining, shopping, and healthcare, this property is approximately 2 hours from Philadelphia and 1.5 hours from DC and Baltimore. **Click on the Movie Camera for Video Tour**

5369 Morgans Point Dr, Oxford

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$17,900,000
5 Beds ⋅ 9 Baths
Stock Range Farm offers a once-in-a-lifetime opportunity to experience the best the Eastern Shore has to offer. With vast working farmland and resort-style amenities, this rare gem truly combines luxury and sophistication with seclusion and tranquility. Sited on 350 acres of prime waterfront, the 12,698 sq. ft. primary residence showcases the breathtaking stylings of acclaimed architect Peter Jay Zweig and exemplifies the pinnacle of luxury living. Built by Ilex Construction, striking architectural details and unparalleled craftsmanship are demonstrated throughout, seamlessly integrating with the breathtaking beauty of the landscape. This magnificent home is filled with an abundance of natural light and boasts panoramic views, thanks to soaring glass walls that overlook the tranquil waters of Pickering Creek, expansive fields, and picturesque vineyards. The thoughtfully curated interior includes spacious living areas, a stunning owner's wing that offers privacy and comfort, and a separate guest wing that features a full kitchen, providing ideal accommodations for family and visitors. High-end features abound, including a gourmet kitchen, recreation room complete with kitchen and bar for entertaining, full exercise room, 5 car garages, elevator, heated limestone floors, Venetian plaster walls, and multiple outdoor decks. At every turn, this property exudes the loving care it has received. Outside, the resort-style amenities include a large, heated infinity pool, complete with waterfall and hot tub, stunning pool pavilion with full outdoor kitchen, stone fireplace, and two TV’s and AV system. Along with the waterside tennis/pickleball court, tranquil koi pond, and private pier with 4-5’MLW, the opportunities for outdoor fun and relaxation are boundless. In addition is the beautifully renovated 4-bedroom guesthouse with views of the vineyards, providing comfortable accommodations for family and friends. A well-equipped 9-stall barn includes a tack room/office, kitchenette, and a riding ring, complemented by 20 acres of fenced pastures. There is also a 3-4 BR caretaker's cottage, a fully outfitted greenhouse, large equipment barn complete with an office and full workshop, and hay barn for storage. The property also offers excellent hunting opportunities, making it a versatile retreat for outdoor enthusiasts. The highlights of this extraordinary property continue through every acre, including sweeping landscapes and hardscapes, 200 acres of working farmland, 5 acres of vineyards, and a 6-acre stocked pond with private island. Unparalleled in its mix of tranquility and luxury, the opportunity to experience the very best of the Eastern Shore’s refined lifestyle and natural beauty is only possible at Stock Range Farm. Additional information and details are available upon request.

27772 Sharp Rd, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 673-3344
$13,500,000
5 Beds ⋅ 6 Baths
Situated on one of the finest residential parcels in the country, Ship’s Point, is an estate with few rivals anywhere, at any price. The completely private 13+/- acre estate includes a deep water pier, and 270-degree views at the confluence of Trippe’s Creek and the Tred Avon River. The south-west facing manor house has been meticulously renovated by renowned builder Winchester Construction. A visit is necessary to understand the rarity of the views provided by the nearly one-half mile of shoreline that surrounds this home.

6010 Shipyard Ln, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665
$9,950,000
5 Beds ⋅ 7 Baths
Travel down a mature, holly tree-lined drive and One Beverly reveals itself with understated Eastern Shore elegance. Situated on the 9 acre original farmstead of the 1867 Beverly Manor, this Georgian home provides a southwestern view overlooking San Domingo and Broad Creeks. The 5-bedroom main house, first occupied in 2003, is a traditional Georgian design meticulously built according to exacting standards to include handmade brick applications, historical window selections, exotic hardwood flooring, limestone fireplaces, custom architectural elements, and an elevator. Craft woodworking is displayed throughout the home's spiral staircase, large kitchen, pantry, and morning room, bathrooms, powder rooms, library, sunset room, fireplace mantles, snooker room, mudroom, map room, ceiling and baseboard trims, and exterior cornices. The central River Room 19ft ceiling provides expansive views of the creek waters and overlooks the terrace which is accessible through triple hung windows. The kitchen and pantry are outfitted with high-end Viking, Miele and Sub-Zero appliances. The large mudroom includes a laundry station, shower, sauna, powder room, refrigerator drawers, a custom farm sink, and an abundance of storage. This homesite includes a guest cottage nestled close to the water, the original carriage house now converted into an office with direct high-speed broadband service, a large pool, an outdoor Viking grill, a Morton barn, a freshwater pond, a greenhouse, and raised brick cutting garden. Established landscaping and majestic trees provide a lush environment to enjoy your Eastern Shore lifestyle.

24629 Beverly Rd, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$9,950,000
6 Beds ⋅ 11 Baths
NEW PRICE! Located minutes from downtown St. Michaels, “Aqua Vitae” the waters of life, sits on 8.6 private acres on Harris Creek, a Chesapeake Bay tributary. This custom-built offering w/ over 400’ of direct water frontage is comprised of 3 magnificent structures: a grand main residence, guest cottage, & “party barn” all highlighted by a waterside pool, pier w/ 4’ MLW, pine grove, putting green, extensive landscaping & incomparable craftmanship. The 12,000 SF main residence, positioned to prioritize water views, welcomes you via prominent double lead-glass doors & a grand 3-story foyer w/ dual-staircase. The “river room” w/ 2-story octagon copula offers 270◦ views of the property & creek. The TV room w/ 3 exposures & gas-burning fireplace offers double French doors on two sides leading to the wrap-around flagstone patio. The stunning gourmet kitchen is a true chefs dream. Offering oversized island, built-in media/storage cabinet, coffered ceiling, fireplace, 3 sinks, double Subzero fridges w/ freezer drawers, 2 beverage drawers, 3 dishwashers, Wolf microwave & a stainless-steel Lacanche range with 6-burners, pot warmer, warming oven, & 2 ovens. Complimenting the kitchen is a large walk-in pantry w/ dishwasher, sink & extra freezer in hall. Off the kitchen is a covered porch w/ gas fireplace & “ghost’ screens, a perfect spot to enjoy evenings. A large open dining room has 2 custom built-in display cases. The grand salon w/ bay window, gas-fireplace & intricate mantel is reminiscent of Paris. Adjoining the salon is the handsome 2-story curly cherrywood library w/ custom display cases & leaded-glass pocket doors. The adjoining climate-controlled wine room has a wet bar & storage for 750+ bottles. Wood floors flow throughout the entire main level. The main level is completed by an office, powder room & laundry to service the pool, 2 additional powder rooms, elevator to all 4 levels, mud/dog room, rear spiral staircase, guest suite w/ ensuite bathroom, & 2-car attached garage. The 2nd level offers a generous primary suite w/ fireplace & full length terrace overlooking the water. Her wing features dressing room w/ custom built-ins, separate sitting room, & a luxurious bathroom w/ marble tile, separate shower, jetted tub, & vanity. His wing offers an office w/ fireplace, paneled closet leading to separate bathroom w/ shower, travertine stone, & vanity. From his office access the 2nd level of library, open to below. Just off of the primary suite is a bar area/kitchen. 3 additional bedrooms, each w/ ensuite bathroom, and a laundry room complete the 2nd level. The 3rd level offers theater/rec room, play area, bedroom w/ ensuite bathroom, powder room, & ample storage. The lower-level houses utilities, storage, & enough room for an exercise area. The charming guest cottage sits amongst extensive landscaping. The main level offers a full kitchen, dining area, living room, sunroom, large family room, 2 bedrooms w/ shared bathroom, additional guest bathroom, & large entertaining room. Upstairs is a full bedroom w/ ensuite bathroom. The unfinished lower level offers storage. The party barn originally built for boat storage was designed to look like an old Pennsylvania barn w/ 4’ of stone around the base. Flanked by 2 garage wings allowing for 4+ cars & capped w/ a cupola, the shingled-style barn has two large doors on either side of the building that allow for a trailered boat or 4+ more cars. The 2nd level is a loft w/ sleeping/living area w/ full bathroom, plumbed for potential kitchenette, front & rear terraces, & a spiral staircase to a crow’s nest w/ amazing views. There is a full property generator & a dog run w/ kennel just off the rear. Outside enjoy the benefits of beautiful shore living amongst the verdant grounds, mature landscaping & exceptional views. The pier offers 4’ MLW & the shoreline is fully rip-rapped w/ natural plantings.

8620 Bozman Neavitt Rd, Saint Michaels

Listing courtesy of Washington Fine Properties, LLC. Contact: info@wfp.com
$8,800,000
6 Beds ⋅ 6 Baths
Wilderness Estate- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 47 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.

27295 Southside Island Creek Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255
$6,450,000
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 (approx. 6 ft 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: chevychase@ttrsir.com
$4,750,000
4 Beds ⋅ 5 Baths
This beautifully refined stone and brick French country home crafted by Ilex Construction, is ideally situated between Easton and St. Michaels and rests on over 4 acres along the scenic Tred Avon River. Spanning approximately 4,500 square feet, this meticulously maintained residence features 4 bedrooms and 4.5 baths. The gourmet kitchen is a chef's dream, equipped with high-end appliances, gas cooking, a spacious island with seating, and an expansive walk-in pantry. The kitchen seamlessly flows into the large family room, which boasts a vaulted, beamed ceiling and a cozy gas fireplace. The separate dining room, also with a beamed ceiling, offers convenient access to a wet bar, making it perfect for entertaining. The main level is home to a luxurious primary suite complete with a beamed ceiling, gas fireplace, and French doors that open to a poolside patio. The spa-inspired bathroom features a spacious walk-in shower, a separate soaking tub, double vanities, and a generous walk-in closet complete with a central storage island. Additionally, this level includes a formal living room, a home office, a laundry room, and an ensuite guest bedroom. Upstairs, you'll find two additional ensuite guest bedrooms and a spacious bonus room, offering ample space for family and guests. Outdoor entertaining is elevated to new heights on the expansive covered terrace, featuring a vaulted, beamed ceiling, gas fireplace, fans, and heaters. The property’s heated saltwater pool, complete with an attached spa, invites relaxation. Other noteworthy features include an attached 3-car garage, a 30x15 shed, an encapsulated crawl space, a fenced backyard, a dock with water and electric, boat and jet ski lifts with approximately 5 ft MLW, a 40-zone irrigation system with remote control, and approximately 300 feet of waterfront with a natural shoreline. 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. Fort Stokes Lane is just minutes from fine dining, shopping, healthcare, theatres, galleries, museums, golf courses, a country club, a yacht club, and a jet airport.

7891 Fort Stokes Ln, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$4,500,000
5 Beds ⋅ 6 Baths
Inspired by the architecture of the French West Indies, this unique 9,334 +/- square foot waterfront retreat features five octagonal wings linked together, offering stunning panoramic views of the Miles River from nearly every room. Step into the luxurious interiors of Rivermark and you'll find yourself immersed in a world of exquisite craftsmanship and timeless elegance. Every detail has been meticulously crafted, from the hand-carved cabinets to the gleaming cherry hardwood floors. The focal point of this magnificent home is the distinguished living room, boasting soaring ceilings that create an atmosphere of grandeur. From the living room, step into the sunroom, where travertine floors and walls of windows wrap around the interconnected spaces of the sunroom, dining room, and kitchen, providing panoramic views of the serene Miles River. Entertaining guests is effortless in the well-appointed kitchen, featuring an Aga stove, granite countertops, and floor-to-ceiling cabinets. Off of the kitchen, the primary suite welcomes you with 18 ft ceilings and en-suite bathroom. For production, Rivermark offers two office spaces with floor to ceiling built-ins and hardwood flooring. On the opposite wing of the home, you'll discover two additional bedrooms adorned with intricate finishes and a shared bathroom. One of the unique features of Rivermark is the octagonal wing housing a hotel-style swimming pool, complete with a sauna room, full bath, and adjacent greenhouse. A separate guest wing provides privacy with its own entrance, offering two bedrooms, two bathrooms, a kitchen, and a comfortable living space. The grounds lends itself to a new level of respite that entails a serene koi pond with a fountain and extensive landscaping. Savor days on the Eastern Shore’s waterways with your private 150 ft dock and boat lift for ease of access to local restaurants or relaxing boat rides. With all of these amenities in mind, plus much more, Rivermark is the perfect home for public entertaining and private relaxation alike. Settlement not to occur before 9/30/2024.

9791 Pintail Pl, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665
$4,499,000
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
$4,495,000
6 Beds ⋅ 10 Baths
Discover a haven of exquisite living with this magnificent property set over 5 acres of prime waterfront, just 15 minutes from St. Michaels. Designed for multi-generational families, large families, or entertaining, the property includes a main residence and a recently renovated guest house, both featuring ground-floor primary suites. The main residence offers breathtaking water vistas, spacious en-suite bedrooms, a versatile third-floor space, an extra-large pantry, and an extra-large laundry room. The guest house includes a modern kitchen, dining and lounging space, a ground-level master suite, a screened porch, and a separate laundry room. Six bathrooms are modern, tiled, and feature quartz finishes, adding to the home's elegant and contemporary design. The property also boasts over 300 feet of pristine shoreline, beautiful views of the bay, a deep-water dock that can host multiple boats and jet skis with its own ramp, an outdoor saltwater pool with an inbuilt jacuzzi, and an indoor Endless Pool Swim/Spa with 3 hydromassage seats. Sustainable amenities include geothermal heating, cooling, and a solar energy system. The second floor of the main residence features an additional primary suite plus another bedroom, both with renovated bathrooms and large walk-in closets. A versatile third-floor space is ideal for a home office or creative studio. An interior corridor past the 3-car garage leads to a dedicated indoor pool zone, fitness area, and cozy family lounge with fireplace and media abilities. The guest house's second floor has two bedrooms, a common area, and a renovated bathroom. With ample space to host family and friends for long periods of time, this property offers both comfort and sustainability in a picturesque setting near St. Michaels and Easton.

6153 Long Point Rd, Neavitt

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

$4,400,000
5 Beds ⋅ 8 Baths
Welcome to Idylwood, an exquisite waterfront estate located in Easton, MD. Ideally situated between Easton and St. Michaels ( and only a quick boat ride to Oxford) this exceptional property offers unparalleled luxury, privacy, and convenience, to those seeking a serene and refined lifestyle. Idylwood showcases architectural Excellence with all brick construction, 10' ceilings, wide antique pine floors, and high-quality Eagle/Anderson windows and doors. The home is incredibly quiet and well insulated, providing a peaceful and energy efficient living environment. The interiors are spacious and elegant, featuring three 3 wood-burning fireplaces that add a cozy ambiance for year round enjoyment. The primary suite on the first floor opens to a blue stone waterside covered porch, where you can enjoy breathtaking sunset views. The second floor boasts a large family/game room, four guest bedrooms with en-suite bathrooms, while the finished third floor, complete with a full bath, can serve as additional living space or storage. The multi-zone HVAC system enhances comfort and efficiency. A charming guest cottage on the property features one bedroom with a brick-floored kitchen /family room and a large wood-burning fireplace. Designed for low maintenance, the estate includes a private waterside pool and pool house, and a sandy beach shoreline perfect for kayaks, paddle boards, and fishing. The 158' x 6' dock with multiple slips, a boat and jet ski lift, and 6' MLW depth accommodates large yachts or sailboats. Modern conveniences including fiber high-speed internet, whole house and yard mesh Wi-Fi, a security system, a Sonos music system, and an Invisible Fence elevate the property's function. Located in Flood Zone X, the property requires no flood insurance. Ideal for gatherings of all sizes, Idylwood combines architectural excellence with a refined. serene lifestyle, making it the ultimate home or retreat. Sold furnished, with a few exceptions, Idylwood is turnkey and ready to enjoy!

6398 Hopkins Neck Rd, Easton

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

$3,995,000
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
$3,875,000
4 Beds ⋅ 4 Baths
Court Road Farm – Twenty Acre Waterfront Homestead improved by a tastefully renovated single-floor residence, nicely appointed guest house and caretaker cottage, pier with boat lift, secured shoreline with riprap and bulkheading, greenhouse with workshop, and a substantial pole barn with 3-phase electric service and HVAC combine to create a marvelous waterfront retreat just nine miles to downtown Easton. The approach to the property off Presquile Road provides a rural setting with abundant open space and natural features. The paved driveway is flanked by mature Willow Oaks and large canopy trees providing a lovely setting along Gross Creek. The property's elevation puts the house and improvements outside the flood plain. With twenty acres there is adequate space for two pastures of three and a half acres each for livestock or habitat restoration and the location, just off the Wye River, is a historic waterfowl staging area and sure to please the nature lover and outdoors enthusiast. The residence was originally constructed in 1970 with major renovations to the house and accessory residences in 2018 providing modern conveniences and efficiency. The primary residence enjoys an open-concept kitchen and living room with casual dining around the kitchen and breakfast table. A double-sided wood-burning fireplace separates the living area from formal dining with all the rooms in the house featuring water views of Gross Creek. The primary bedroom suite and two guest rooms, each with baths en-suite, are located off a transverse hallway with an additional bedroom suite adjacent to the kitchen. The primary suite has a large walk-in closet with a sauna and laundry located on the bedroom wing. Abundant storage and gracious room sizes complement the residence with easy access to mechanical systems in the walk-up attic and a dry crawl space with a concrete slab underneath. A utility room/workshop is located within the oversized two-car garage. The two accessory dwellings are located at an appropriate distance from the residence. Noted as the Caretaker Cottage, this three-bedroom, two-bath, single-floor residence provides a great opportunity for extended family, guests, or a caretaker. Similarly, the Guest House is located beyond the primary residence and provides three bedrooms with one and a half baths, a farmhouse-style kitchen, and a waterside living room with a fireplace. Both accessory dwellings have been updated with modern HVAC and finishes. Additional improvements to the property include a 120 X 60 Pole barn with heating and cooling, a greenhouse and workshop with mini-split heating and cooling, a tractor shed/utility shop with a single bay garage, and a boat equipment shed near the dock. The dock has an 8,000lb boat lift and the shoreline is intact with rip-rap, bulkheading. Within seven miles of Easton Airport (ESN), nine miles to downtown Easton, and seven miles to St. Michaels by water, Court Farm provides a unique opportunity to own a substantial waterfront property in a mature setting on Maryland’s Eastern Shore.

27047 Presquile Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255
$3,800,000
5 Beds ⋅ 5 Baths
Osprey Point is a one-of-a kind, highly crafted composition of nature, architecture and art. A private, serene Eastern Shore retreat or family compound with spectacular sunsets, deep-water pier and approximately 1500 feet of shoreline. The manageable 6.69+/-acre park-like setting features west and southwest exposure of Island Creek with prevailing, cooling summer breeze, exceptional panoramic water views, a multitude of beautiful, specimen trees and gardens, sweeping lawns, protective living-shoreline, and small, stone revetment jetties. An additional adjacent , 2.32+/-acre waterfront lot with high elevation and deep water is listed separately and can not be sold prior to sale of house . Designed by Pamela Gardner and built by Peter Hanlon in 1996, this architecturally distinctive yet elegant and classic 5,828 square foot home with two turrets, 10 foot ceilings, gorgeous exposed-beams, stunning woodwork and ten foot ceilings offers light-filled, water views from every room. The warm, open and inviting interior spaces lend to relaxation and enjoyment of the outdoors from within. The waterside pool, patios and porches are wonderful for entertaining guests and the stately entrance and vast, manicured lawns are welcoming. Grand entry within the front turret showcases its beauty with up-lighting. Rear turret includes a scenic third floor overlook with kitchenette for an additional private space to unwind. The first floor includes a large open kitchen featuring hand-painted, ceramic tiles depicting the wonderful wildlife of Chesapeake Bay, a walk-in wine cellar or larder and a separate pantry, the primary bedroom suite with two walk-in closets, a very large office or additional 5th bedroom, great room with wood burning fireplace, cathedral ceiling and large bar area, the family room with gas fireplace and dining area. The formal dining room is located across the hall from the kitchen. There are many hand-crafted built-ins throughout and additional attic storage on the second floor and above garage. Oversized three car garage has fourth bay for boat and outdoor toy storage. Four-zoned heat pumps with gas back up cool and heat the residence and there is also a back-up generator. Osprey Point is situated perfectly between Oxford and Easton. By water, this address also provides quick access to some nearby, locally known beaches, restaurant and ice cream establishments of Oxford as well as the Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina.

28080 Brick Row Dr, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665
$3,395,000
5 Beds ⋅ 6 Baths
This beautiful waterfront estate with broad views of Plaindealing Creek is being sold furnished (except for owners personal belongings and some artwork) and was tastefully decorated by Come by Chance out of St Michaels. Sited on 21 acres (zoned agricultural) the property provides the utmost in privacy, and features a waterside pool, hot tub, and pier with lift and 3+ MLW. The main house offers spacious living areas boasting elegance and charm, high ceilings, gleaming hardwood floors, and bespoke finishes. The open floor plan on the main level features a gourmet kitchen with stainless appliances and center island, a large family room with cathedral ceiling and wood-burning fireplace, an expansive enclosed sunroom overlooking the pool and creek, and formal living room and dining room. In addition, there is a guest bedroom (could be used as an office too) and full bath. On the second floor, the primary suite is a rare treat featuring an ensuite sitting/reading room with panoramic water views, luxurious primary bath with soaking tub, separate shower, double vanities, and his/hers walk-in closets. Two additional bedrooms, a large hall full bath, laundry facilities, private nook (currently used for additional bed space), and open landing overlooking the family room complete the second level. The third floor is completely renovated, has shiplapped walls, and includes a full bath. Finished with multiple bunk areas, this incredible space provides great fun for kids and guests. An attached 2-car garage and small dog run complete the main residence. Adjacent is a 2-car detached garage with a charming studio apartment above, boasting hardwood floors, bedroom, kitchen and living areas, full bath, and outdoor deck. An additional 1-bay garage/shed is also onsite providing ample storage for boat, tractors, etc. Whether you're enjoying the tranquility of outdoor living or hosting lively gatherings with friends and family, this property offers the ultimate of being on the Eastern Shore. Note: The lane is owned by this property though the two neighbors on the left have 'right of way'.

6694 Hopkins Neck Rd, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 673-3344
$3,350,000
3 Beds ⋅ 5 Baths
Welcome to this serene oasis nestled on the coveted Miles River, where tranquility meets luxury in this Japanese-inspired waterfront property. The meticulously crafted home has been curated to offer the ultimate in comfort, style, and refined elegance. The exterior of the home is a masterpiece of design, featuring lush gardens with native plants and flowers, trickling fountains, attractive foot bridges, and a Koi pond, creating a sense of peace, serenity, and privacy. A swimming pool, private pier with 3'+/- MLW, designated barbecue area, extensive patio, storage shed, and 2-car attached garage complete the exterior amenities. Inside, admire gleaming hardwood floors, custom cabinetry, and designer finishes throughout. The gourmet kitchen, featuring upgraded appliances, provides ample space for preparing culinary creations. Entertain guests in the luxurious living room, featuring a wet bar with wine storage, or enjoy a formal meal in the dining room, while enjoying views of the river, pool, and gorgeous grounds. The primary suite is conveniently located on the main level, offering a sumptuous ensuite bath with glass-enclosed shower and soaking tub, walk-in closet, and private waterside deck. Two additional bedrooms upstairs, each with their own private balcony and ensuite bath, and a bonus room, offer plenty of space for guests and storage.

27168 Anchorage Rd, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 673-3344
$3,250,000
4 Beds ⋅ 4 Baths
**Luxurious Waterfront Modern Farmhouse in Easton, Maryland** PLEASE VIEW THE VIDEO TOUR OF THIS BEAUTIFUL HOME! Situated 12 feet above mean high water, discover serenity and luxury with this 2022-built modern farmhouse on Dixon Creek. Elevated for breathtaking southwest views, it features a 20-foot-high ceiling in the main room, modern finishes, and a vibrant tapestry of nature. Enjoy a 50-foot covered pool and a 12-person in-ground hot tub, along with an outdoor entertainment pavilion for unforgettable experiences. The open-concept design includes a gourmet kitchen with top-tier appliances, flowing into spacious living areas. It boasts four bedrooms, three and a half baths, large windows, and French doors leading to a beautiful outdoor Travertine patio. Situated in a quiet, rural setting, it's minutes from Easton, St. Michaels, and Oxford. The property features a dock with custom lifts, professional landscaping, a concrete fire pit, and an outdoor cedar wood shower. Enhancing this home's charm is the 2.9-acre grounds with a fenced cedar raised bed garden. The first-floor primary suite offers luxury with two walk-in closets and a standalone soaking bathtub. One bedroom ensuite, two additional bedrooms and a first-floor office provide comfort and utility. The home is built with integrated concrete form (ICF) construction, making it strong and energy-efficient. Systems include a geothermal heat pump, a Rinnai tankless water heater, a whole-house backup generator, and reverse osmosis drinking water. This waterfront modern farmhouse is a blend of luxury, resilience, and sustainability. Experience the beauty of Maryland's waterfront living with easy access to urban amenities. Schedule your exclusive showing today! (Please note that most GPS applications will take you to the wrong address. Take St. Michaels Rd to Leehaven Rd to left on Jarboe and house is first on right).

27919 Jarboe Dr, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$3,200,000
6 Beds ⋅ 5 Baths
Welcome to paradise, 8 acres of waterfront property on Cedar Point just minutes from St Michaels. The main house sits just off of the water on the point with magnificent water front views. This house has been completely remodeled with 3 bedrooms, and 2.5 baths. It has main floor living with a tremendous owners suite that looks out over the water. The floorpan is open with custom trim and finishes, high quality wood flooring and high ceilings throughout, dual living areas with their own fireplaces, a gourmet kitchen with wolf appliances, a massive quartz island and dining area that looks out over the water. There is a large screened in deck, for enjoying your piece of paradise 3 seasons fo the year. The second floor hosts two more bedrooms each with their own balcony, as well as a full bath, as well as tons of storage and the potential for more finished space. The large yard that leads to the point ends in thousands of feet of shoreline and a pier for fishing or docking your boat, the water fluctuates from 3-7ft according to the tide. Off of the main house is a detached two car garage with the potential for a second floor apartment. The second house on this property is a 3 bedroom, 2 bath rancher with a detached garage, and workshop. This house is also move in ready and fully livable. Across from this house is a water front kennel building that has its own bathroom, as well as a pole barn. There is tons of potential here for all kinds of visions you may have. This property is wonderful for fishing, boating, farming, waterfowl hunting and much much more! Be sure to check out the neighboring listing at 6589 Cedar Cove Rd that is a 3 bedroom, 2 bath rancher on over 17 acres of waterfront. Can be purchased as a package deal!

6591 Cedar Cove Rd, Royal Oak

Listing courtesy of Homeowners Real Estate. Contact: (410) 967-5995
$2,950,000
4 Beds ⋅ 5 Baths
This exceptional waterfront estate, nestled on approximately 4.25 private acres with sunset views of Plaindealing Creek, features a custom pier equipped with electric, water, along with a rip-rapped shoreline. Positioned just off the Tred Avon River, the property includes a fully irrigated lawn, a year round porch with brick flooring and separate HVAC. There is also a waterside composite deck. The meticulously maintained four-bedroom residence boasts antique wood flooring throughout, a stunning gourmet kitchen, waterside great room with fireplace and custom built-ins, and separate den/family room with beautiful built-ins. The main-level owner's suite offers custom closets and a luxurious bathroom with a freestanding soaking tub and a separate tiled shower. Upstairs, you'll find a cozy loft ideal for a library or sitting area, custom skylights with power shades, and a rooftop balcony that connects to a finished bedroom/craft room over the attached two car garage. Additional amenities include a detached two-car garage with a bonus area above, a detached RV garage, and a boat shed. Conveniently located just minutes from Historic Easton and St. Michaels.

26362 Westerly Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$2,875,000
4 Beds ⋅ 5 Baths
Location, Westerly Views, Sailboat Depth Water, Privacy! Welcome to this stunning waterfront home, a true sanctuary overlooking Plaindealing Creek. Spanning 4074 square feet, this residence includes 4 spacious bedrooms, 3 full baths, and 2 half baths, providing ample space and comfort for family and guests. Sited on 5.06 acres of beautifully manicured grounds and stunning mature trees, the property has 327' +/- of natural shoreline and 6-7' MLW, ideal for boating enthusiasts. The private pier features two boat lifts, three deep-water slips, and a large floating dock. Enjoy breathtaking 180-degree views of the water from much of the house, or from the in-ground heated saltwater pool. Inside, you will find beautiful hardwood flooring throughout and an abundance of natural light. The living room and sunroom showcase big views of the pool, back yard, and creek from multiple sliding glass doors leading to an expansive wrap-around waterside deck. The large family room w/ cathedral ceiling has French doors to the deck, and a wonderful wood-burning fireplace. The main level primary bedroom with ensuite bath and large walk-in cedar closet are private and overlook the back yard and creek. Adjacent is the separate office with great built-ins and desk. The light-filled eat-in kitchen with center island is convenient to the formal dining room, a pantry/mudroom area, and wonderful breezeway with brick flooring serving as a screened porch/additional sunroom. On the second level, enjoy three well-appointed guest bedrooms, a full hall bath, and a second access point to the walk-in attic space over the garage. The home's thoughtful design includes extensive storage space & cedar closets, an enormous walk-in attic, bonus area accessed by a spiral staircase, and a dedicated fitness room complete with an adjacent steam shower/steam room. An attached 2-car garage with access to the walk-in attic overhead, workshop, and wonderful built-ins, and storage shed complete the property.

26326 Heronwood Rd, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 673-3344
$2,625,000
4 Beds ⋅ 4 Baths
Privately located between Easton and St. Michaels this beautiful Southern Living Eastern Shore Cape Cod style home sits on the sought after Tred Avon River offering 400'+ of water frontage, pier with boat lift, newly protected shoreline, gorgeous water views, and waterside swimming pool .Water views from most every room, this home offers a beautiful rocking chair style front porch, great room with vaulted ceiling, fireplace, gourmet kitchen with high end appliances, granite counters, and walk in pantry. Fabulous conditioned sunroom with ceramic tile flooring, full of natural light. The first floor owner's suite has a recently remodeled by Lundberg builders a luxurious tile bathroom with heated floors, heated towel rack, & zero threshold shower. The second floor offers three bedrooms, 2 full baths, plus a huge bonus room offering ample space for guests or recreational activities. Perfect location by water to Historic Oxford and the Choptank river. The owner prefers to sell the property furnished, ensuring a seamless transition into your new waterfront retreat. Don't miss the opportunity to make this waterfront oasis your own. Hot tub and boat lift go in "as is" condition.

5993 Hopkins Neck Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$2,395,000
6 Beds ⋅ 4 Baths
Perfectly sited on the shores of Dixon Creek, this charming home offers timeless elegance and modern amenities across three expansive levels. Sited on 1.437 acres, the property boasts an impressive 618’ of waterfront, offering panoramic views across Dixon Creek and up the Tred Avon River. Inside, the home features gleaming hardwood floors, high ceilings, and four wood burning fireplaces, creating a cozy and welcoming ambiance. The spacious gourmet kitchen offers high-end appliances, coffered ceilings, an excellent center island with 5-burner gas stovetop, breakfast bar, dining area, and sitting area with views to the water. The large family room and paneled library are designed for comfort and relaxation, featuring two of four fireplaces, custom built-ins, and ample room for family living. On the second floor, the grand primary suite presents a generously sized primary bedroom with private balcony, deluxe ensuite bath with glass-enclosed shower and jetted tub, and an ensuite bonus room (could be office; currently a billiard room). Two additional bedrooms, a full hall bath, and laundry facilities complete the second floor. On the third level, discover three additional bedrooms, a full hall bath, walk-in storage room, and an enormous walk-in attic. Outside, the screened waterside porch is ideal for entertaining/dining, and the cozy fire pit provides the perfect setting for evening gatherings. A private dock with 5'MLW, boat lift and three slips is well-suited for water enthusiasts, while the natural shoreline, framed by mature trees and vibrant landscaping, creates privacy. Additional features include two outbuildings, an outdoor shower, and a 1-car attached garage. This idyllic retreat is perfect for water lovers and those seeking privacy, while being conveniently located between Easton and St Michaels (by car) and Oxford (by water).

7701 Bloomfield Rd, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 673-3344
$2,350,000
4 Beds ⋅ 5 Baths
Almost Complete! 4 bedroom, 4.5 bath Coastal style home with in-ground pool and pier! Just 60' from the water, this is the epitome of waterfront living. Large second floor balcony, wrap-around porch, and open floor plan with wide banks of windows provide ample opportunity to enjoy the gorgeous water views. Main-level primary suite with dramatic cathedral ceiling and luxurious spa-like bath. Attached 2-car garage, approximately 325’ of shoreline with newly planted living shoreline. Easy year round living or second home on the Eastern Shore as the association handles lawn maintenance and snow removal. Centrally located between Easton and St Michaels and just a stone's throw from the Oxford Bellevue Ferry on the Tred Avon, Bellevue on the Tred Avon is just a short boat or ferry ride to Oxford’s restaurants, ice cream shop and waterfront park.

25839 Turner Ave, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665
$2,249,900
3 Beds ⋅ 4 Baths
Nestled among the serene loblolly pines, this exquisite 4+/- acre waterfront lot offers an unparalleled retreat overlooking the tranquil waters of Broad Creek. Take a front row seat to colorful sunsets year-round thanks to the south-westerly views. Former Church Neck Road adjacent neighbor, James Michener, undoubtedly drew inspiration from similar water views for his novel ‘Chesapeake’, enriching the legacy of this storied locale. Step inside to discover a sanctuary of serenity, where water views greet you from nearly every room on the main level. From the comfort of the primary suite to the warmth of the living room, complete with a wood-burning fireplace, and the inviting ambiance of the dining room, and the sun-drenched charm of the kitchen's sunroom, each space invites you to unwind and soak in the natural beauty that surrounds you. The living room boasts vaulted ceilings, drawing your gaze upward to accentuate the sense of space and airiness. Upstairs, two bedrooms and a library office offer a bird's-eye view of the main living area below. Meanwhile, above the garage, an additional bonus two room office/study space await, complete with a full bathroom, ready to adapt to your every need. Outside, a 2-car garage stands ready to accommodate your vehicles or storage, while a waterside stone patio provides the perfect spot to bask in the gentle rhythms of the rip-rapped shoreline. Experience the magic of waterfront living and prevailing southwesterly breeze in this idyllic retreat, where every moment is infused with the timeless beauty of the Chesapeake Bay.

7930 Church Neck Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665
$1,895,000
3 Beds ⋅ 3 Baths
Conveniently North of Easton with easy Rt 50 access,9.8 acres on the Miles River, Southern exposure, dock, exceptional privacy with panoramic water views. 3,00sq.ft. +-, with pool and gazebo, 3 car garage, exceptional trees and mature landscaping. Split floorplan with MBR on one side and other BR on other side, family room, breakfast nook and kitchen , large office with built ins. and huge game room with expandable 2nd floor and built in stairs. Unique large property with great water for fishing and crabbing.

10425 Aberdeen Ln, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665
$1,795,000
5 Beds ⋅ 6 Baths
This stunning waterfront property offers a serene lifestyle with a spacious 3-bedroom main house, each bedroom featuring its own en-suite bathroom, including a convenient main-level suite. Enjoy breathtaking water views from most rooms, whether relaxing in the formal or casual living and dining areas. The home features hardwood floors in many rooms including a few under the carpets. The grounds are green and lush and include a waterside concrete, in-ground pool perfect for entertaining. The property also includes a bulkheaded waterfront and a boathouse on Shipshead Creek. Attached 2-car garage and a garden shed provide for abundant storage. Situated on 3.3 acres off St. Michaels Road near Easton, it also features a charming two-bedroom guest house, making this a perfect retreat for family and friends.

7968 Bloomfield Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665
$1,699,500
5 Beds ⋅ 4 Baths
Nestled along the quiet waters of Boone Creek, this 5 bedroom, 3.5 bath home has beautiful water views, incredible custom woodwork and is in impeccable condition. Nice paver patio overlooking the Creek. Dock with boat lift and access to Tred Avon and Choptank Rivers. Close to Oxford activities, restaurants, and marinas. Various types of hardwood wide plank floors, living room has custom fireplace surround with enclosure above. Sliding doors to patio, screen porch off of breakfast room, large primary suite on first floor. On the second floor, one bedroom is an en-suite plus large additional bath to serve the other two bedrooms. The 5th bedroom upstairs is currently set up as an office. Lots of storage space. Two car attached garage w/built in stairway to large storage attic. Large garden shed. Bilco door access to concrete floored crawl space.

26226 Langs Landing Rd, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$1,695,000
3 Beds ⋅ 3 Baths
This substantial brick home with gorgeous sunset views across Harris Creek is a private retreat just five miles from St. Michaels' shops and restaurants. Sited on 4.7 mostly-wooded acres, the home features a first floor primary suite with waterside sitting area, a family room with woodburning fireplace and a striking stone accent wall, dining room, spacious eat-in kitchen, den and screened porch. Upstairs are two bedrooms with a Jack and Jill bath. There is an attached, oversized two-car garage and a detached heated and air conditioned office with built-in bookshelves - the perfect office or studio. Built in 1998 with steel framing and oversized brick, this house feels solid. It is well elevated, in the preferred low flood risk "X-Zone." The panoramic views are exceptional! Substantial 5' x 150' dock. Over 200' of protected shoreline. Just-completed boundary survey suggests there is room for a waterside pool. Buyer to confirm.

8288 Bozman Neavitt Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$1,545,000
3 Beds ⋅ 3 Baths
Three bedroom home on Tred Avon River features a six foot deep water private dock with boat lift, water and electric on dock. Beautifully landscaped. Pool, patio and nice outdoor living area. Solar array for power - EV charging station. Oversized two car garage and attached workshop. This house is all about the property and the fabulous unobstructed river view. Rear view is south facing. Rear yard is fully fenced with split rail and wire. The is an extension on the side yard driveway for RV storage with electric service in place. Driveway is stone/gravel in keeping with the rural attractiveness of the property. Currently two bedrooms used - third is an office. Both guest and office have walk-in closets and access to shared bathroom. Main bedroom at the end of the house has rear yard and south facing water view. Bath has vanities on both side, shower , separate toilet, two large closets. Kitchen and family room bar have oak cabinets and granite countertops. Vermont castings gas stove in main living room for cooler nights. Laundry room with upright freezer as first room entry from garage. All current appliances stay with the house.

26675 N Point Rd, Easton

Listing courtesy of Continental Real Estate Group. Contact: 8779965728