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$9,900,000
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

$8,900,000
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

$7,950,000
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 (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: chevychase@ttrsir.com

$5,900,000
5 Beds 5 Baths
Make an appointment now to see "Shamrock Shores," Talbot County's newest waterfront listing. Sited on a premier 7.5-acre parcel, providing commanding SW views across the confluence of Glebe Creek and the beautiful Miles River, a multi-year, multi-million dollar renovation of the main house and dependencies has just been completed, incorporating the latest and greatest state-of-the-art systems, electronics and materials. The first word visitors often say when they walk in the front door, is "Wow!" The design, craftsmanship, quality of materials and attention to detail is apparent throughout. Standing in the entry, you will admire the wide-plank wood floors, vaulted ceilings and walls of glass along the waterside. Late in the evening, you will enjoy beautiful sunsets over the Miles River, looking out those windows. This is a very bright, open and spacious home. The scale of the house is just right, not too big and not too small, with approximately 4,200 sq. ft. of geothermal-heated living area...all on one level! At one end of the house is a luxurious primary suite, which includes a private, wood-paneled office and one of the finest bathrooms we have seen. At the opposite end of the house, you will find two comfortable guest bedrooms, both providing views of the water. In between, there is a spacious dining area and two comfortable living areas, separated by a stunning kitchen. This amazing kitchen, located at the center of the house, is a chef's dream kitchen with a huge center island and top-of-the-line cabinetry and appliances. Spacious waterside screened porch, plus an open blue-stone patio, near the water. Several hundred feet from the main house, you will find an exceptional 2-bedroom guest house. It's so nice and so comfortable, you might have trouble persuading your guests to ever leave! Just beyond the guest house, there is a vernacular "Barn," with room to house a car collection, a large motorhome, or perhaps the 22' x 44' space could serve as a perfect "Party Barn." For boaters, there is a substantial deep-water dock to accommodate motorboats and/or sailboats, large or small. A heavy duty boat lift will support boats up to 50,000 pounds. The location is ideal, easily accessed from Route 50 and Easton Airport. Historic Easton, MD is just a 10 minute drive away. The Town of St. Michaels is just a 20-minute drive by car, or you can hop in your boat and take a short, scenic cruise down the Miles River to St. Michaels Harbor.

27669 Villa Rd, Easton

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

$4,995,000
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

$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

$3,750,000
5 Beds 8 Baths
Due to personal circumstances this property now includes new enhancements and a drastic price reduction to the previous listing. The listing now includes the adjacent waterfront parcel of 8.5 acres making for a total of 17 acres. The additional parcel is complete with a pier, barn with a 2 bedroom apartment as well as a fenced pasture. 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.

10205 Kintore Dr, Easton

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

$3,495,000
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: (410) 822-6272

$3,400,000
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

$2,200,000
3 Beds 3 Baths
Whitehall Building's single story 3 bedroom and 2.5 bathroom TO BE BUILT NEW CONSTRUCTION presentation includes vaulted ceilings in the family room that are visible from the foyer. Step into the room and you'll find a fireplace on the right wall flanked by built-ins and views that extend across the rear porch with fireplace and to the kitchen. The gourmet kitchen features a walk-in pantry, large prep island with seating for four, and a nearby formal dining room, gourmet appliances and more. For warmer months, enjoy the grilling porch just outside the kitchen. The primary bedroom is quietly situated on the left side of the home, and boasts vaulted ceilings, a spacious bathroom with a large walk-in closet, and a separate tub and shower. Two secondary bedrooms are located on the opposite side of the home and share a Jack and Jill bath. Stairs take you to a bonus room with bath and can be used as a fourth bedroom, home office or play room. Behind the home, a garage has room for two vehicles. A separate storage area gives you space for yard equipment and other gear. Exposed brick, wooden beams and other decorator finishes are NOT standard and will not be included in offering. 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.

28752 Jennings Rd Unit #LOT 4, Easton

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

$1,595,000
4 Beds 4 Baths
Nestled in the highly sought-after Cookes Hope community, this waterfront retreat built by Willow Construction redefines upscale living. The main house, featuring 3 bedrooms and 2.5 bathrooms, includes a desirable main-level primary suite with a custom walk-in closet, double vanity, soaking tub, and tiled steam shower—all with enchanting water views. The welcoming den, adorned with a gas fireplace, serves as a perfect escape or home office space. The birds-eye lookout loft room bathes in ambient light, and the kitchen boasts a breakfast bar, warming drawer, and beverage refrigerator. Enjoy hosting gatherings on the screened-in porch or waterside deck with a natural gas hook-up for grilling. A detached guest apartment, complete with 1 bedroom and 1 bathroom, provides additional flexibility and comfort. Additional amenities include a detached 2-car garage, built-in bookcases, cathedral and vaulted ceilings, and a covered front porch. Situated on 1.9+/- acre property and also includes a 2024 slip rental at the community pier.

6780 Cookes Hope Rd, Easton

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

$775,000
3 Beds 2 Baths
Great opportunity to enjoy your private 1.72 acre oasis in the highly desirable Waverly community located off the Oxford road, minutes from downtown Easton. This 3 bedroom/2 bath single level home offers charm and character in a park-like setting. Special features include 2 wood-burning fireplaces; hardwood and tile flooring; spacious family room with custom built-ins and dual heating system (radiant heated floor and forced air heat);radiant heated floor also in remodeled hall bathroom; rear patio and pool deck; salt-water concrete pool. 38'x 36" detached garage/barn/ carriage house fully drywalled and heated, with a 5-car capacity and a 10' high RV accessible entrance. The property is around the block from the community deeded dock . A new BAT (Best Available Technology ) septic system was installed in October. Previous contract has been mutually terminated as buyer could not wait for septic system to be completed. Seller has estimates for work on crawl space and roof.

7630 Tred Avon Cir, Easton

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

$619,900
4 Beds 3 Baths
Built in 2019, this well-maintained 4-bedroom, 3-bathroom Cape Cod situated on a 1+/- acre lot is waiting for you. As you arrive, the inviting covered front porch welcomes you into the home. As you step inside to discover an open floor plan on the main level, seamlessly connecting the living, dining, and kitchen areas. The main floor also features 2 bedrooms, including the primary suite complete with 2 closets and a bath. The kitchen is complete with stainless steel appliances, beautiful granite countertops, and a spacious island with seating for 4, perfect for casual dining and entertaining guests. On the 2nd floor, you'll find 2 additional bedrooms and a full bath, as well as the expansive unfinished attic space with spray foam insulation, which presents endless possibilities for customization, whether it be as a recreational area, home office, or additional storage. Beyond the aesthetic appeal, this home has additional conveniences such as the attached 2-car garage, the UV light on the HVAC system, an encapsulated crawlspace, and gutter guards providing added peace of mind and ease of maintenance.

6998 Hopkins Neck Rd, Easton

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

$599,990
3 Beds 2 Baths
ANOTHER BIG PRICE REDUCTION! ! 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 lots of space for your design ideas. 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: