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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:

3 Beds 2 Baths

27429 Rest Cir, Easton

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

4 Beds 3 Baths
Well-maintained Craftsman style home located in the heart of Easton's Historic district. This beautiful home features a rocking chair style front porch, rear deck, stunning original pine flooring recently refinished throughout, a large dining room with a built-in corner cabinet, and French doors that open into a cozy family room with wood stove insert. The second floor offers a large primary bedroom suite with private bath and WIC, two additional guest bedrooms, hall bath and extra room great for office or another bedroom. Additional features include: a large basement with inside and outside access, large attic space partially finished, recently replaced gas furnace, three-zoned HVAC, all knob and tube wiring removed, and a outdoor storage shed with electric. Just a few short blocks away from hospital, downtown shopping, restaurants, parks, and walking trails, this home combines historic charm with modern convenience.

300 S Aurora St, Easton

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

3 Beds 1 Baths
This two story 3-bedroom, 1 bath home in Easton, Md offers a fantastic opportunity for buyers looking for a cozy and conveniently located property. Situated within walking distance of downtown Easton, residents can enjoy easy access to shops, restaurants, and local attractions. The home has an open concept layout, providing a spacious and inviting atmosphere for both living and entertaining. The property also features a decent driveway, providing ample parking space for residents. With a ample sized backyard including a large shed, there's plenty of room for outdoor entertaining. This home is an excellent opportunity for buyers looking to invest in a property with loads of potential. While the home may require some tender loving care, it presents a perfect canvas for buyers to make it their own. Being sold As-Is. Home is contingent upon sellers home of choice.

105 Glenwood Ave, Easton

Listing courtesy of EXIT Sunshine Realty. Contact:

4 Beds 4 Baths
Located on a serene side road, only minutes from both downtown Easton and Oxford, this bright and tranquil home features 3600+ sqft and 2+ beautifully landscaped acres overlooking the 15th fairway of the Talbot County Country Club.  At the heart of the home, the spacious kitchen includes vaulted ceilings, high-end stainless steel appliances (Blue Star 6-burner gas stove, GE Monogram refrigerator/freezer), soapstone counter tops, ceramic flooring, a large center island with a butcher block counter top, and a breakfast nook with new custom built in seating. A nearby butler’s pantry provides additional dishwasher, utility sink, and washer dryer. The main floor also features the family room with a wall of windows and wood-burning fireplace, the living room with custom built-in bookshelves and 2nd wood-burning fireplace, a formal dining room with French doors leading out to the back patio, a light-filled corner office with French doors, and an enormous screened front porch with peaceful views. An in-law suite also overlooks the backyard, including a large living room with beamed vaulted ceiling and luxury vinyl plank flooring (2024), large guest bedroom, kitchen, private bathroom with walk-in shower, and separate entrances from both a private porch and the garage. Upstairs features a sunlight-flooded primary bedroom with a large walk-in closet and an entirely remodeled, enormous bathroom (2022), featuring walk-in shower and stand alone soaking tub. Down the hall are two additional large bedrooms and another full bathroom. The sun-filled backyard features large mature trees offering plentiful spots of shade, a custom made walk-in raised bed garden, and the perfect gentle breeze, which, according to the homeowners, seems always to carry from the many surrounding waterways. Recent upgrades include a fully encapsulated crawlspace by Total Home Performance, new BAT septic system, ChargePoint EV charging station (in garage), new windows, 6.9kw solar array, and new water Dealkalizer System (in garage).

6343 Canterbury Dr, Easton

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

3 Beds 2 Baths
Occupancy Permit in hand--move in ready! Welcome to the very first beautiful custom home in Easton’s hottest new ten lot downtown subdivision of Sandy Lane. This brand new elegant and convenient one-story home is an original, one-of-a-kind design by architect Darren Johnson, painstakingly constructed by the renowned local custom builders Stansbury and Sons. This custom one-story home known as the “Wylie” features a fresh, contemporary floor plan with open living, dining and kitchen area; vaulted 16-foot ceilings in the living room, three bedrooms, two full baths, laundry, an attached garage and breezy large 240+/- sf deck off the kitchen/dining area which is perfect for entertaining. Take note of all the extras you cannot see--superior framing and finish construction, state of the art insulation, encapsulated crawl space with dehumidifier (great space for storage), and so much more. Whether you work from home or have a growing family, the flexible floorplan of the Wylie will suit your needs. Interior finishes and features include high quality luxury vinyl flooring throughout, large windows bringing in tons of natural light, ample closet space, contemporary ceiling fans in all the bedrooms, a custom kitchen and two full baths with high-end cabinetry, quartz countertops, tiled showers, gorgeous fixtures and premium stainless appliances in the kitchen. The Wylie, which sits on over a quarter acre, is surrounded by lovely premium landscaping and the entire yard is completely sodded and ready to go! There is nothing like the quality and charm of the custom home construction on Sandy Lane in all of Easton—aptly voted one of the top ten small towns in the entire U.S.! The new Sandy Lane neighborhood is conveniently located off N Washington Street in the town of Easton proper thus you can enjoy all the perks of downtown living including Easton Utilities all-encompassing electric, water & sewer, cable & high-speed internet service; weekly town trash pickup; beautiful downtown parks with ball fields, hiking paths, cinder track, playgrounds, tennis and pickleball courts, community pool and fenced dog space; beautiful waterfront access; Easton fire and police services; medical, cultural, shopping, incredible dining experiences and so very much more! Not to mention all the additional opportunities found throughout the rest of Talbot County. Developer paid all infrastructure costs up front (permits, site work, water, sewer, electric, cable, street, sidewalks, streetlights, etc) so no extended yearly front foot fee to Buyer! Room measurements and all other information provided believed to be accurate but not guaranteed.

6 Sandy Ln, Easton

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

3 Beds 3 Baths
Well maintained Treehaven town home just steps away from Rail-to -Trails and short walk to downtown Easton and all of its amenities. Offering open 1st floor plan with wood laminate flooring, spacious kitchen with all access, dining area, half bath, laundry, pantry and double closets. 2nd floor offers Brand New Carpet and generous primary bedroom with attached private bathroom and large wall closet and double windows. There are also 2 additional bedrooms and another full bath and linen closet. Upgraded blinds installed throughout. This is a low maintenance unit with 2 assigned parking spaces and small rear patio area. Trash removal, landscaping and snow removal included in HOA. . Seller will provide 1 year HOME WARRANTY with acceptable offer.

510 Brookletts Ave Unit #603, Easton

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

5 Beds 6 Baths
Welcome to "Wheatlands", one of Talbot County’s most significant and spectacular estates overlooking the Miles River. Sited on 40+ acres (including a separate16-acre parcel, currently farmed), this iconic property is pristine in every way, and offers unparalleled privacy and beauty. After passing through the entrance pillars, one is mesmerized by the long tree-lined drive, an extraordinary English garden, incredible mature trees and landscaping, and breathtaking views from every vantage point. A sweeping circular drive leads to the 5BR/5.5BA main house while a separate lane accesses the 2BR/2.5BA guesthouse, stunning barn with owners’ office and lounge, separate recreation house, and charming chicken coop. The large boathouse with its upper sun deck is perhaps the most coveted in Talbot County and has 2 boatlifts (one covered), 7’MLW, a floating dock, and shower. In addition, there is a delightful bath house with wine cellar below, a waterside heated saltwater pool, shuffleboard court, and potting shed. The iconic Federal-style manor house has been exquisitely renovated by the current owners who have seamlessly combined the comfort of everyday living with the timeless elegance of the past. Built circa 1750 by General Perry Benson, a Captain in the Revolutionary War and Major General in the War of 1812, all rooms have stunning river vistas and extraordinary details such as high ceilings, floor-to-ceiling windows, elaborate moldings, original oak and refurbished pine flooring, bespoke finishes, and masterful craftsmanship. A welcoming grand foyer, elegant living room with fireplace, dining room with fireplace and paneled murals, and a fabulous family room with its massive fireplace and beamed ceilings, provide great entertaining spaces and comfortable family retreats. Beautiful brick patios and terraces extend the length of the rear of the home offering riveting water views. Modern luxuries are found throughout the home and include a fabulous chef’s kitchen with an enormous hand-crafted mahogany center island, honed marble countertops, and top-of-the line appliances. The first-floor primary suite offers a private library/sitting room, fireplace, French doors opening to a patio with hot tub, 3 walk-in closets, and an automatic drop-down stair to a private yoga area. The luxurious bath features a marble tiled steam shower, hewn copper soaking tub, double vanities, and refurbished yellow heart pine floors with radiant heat. The grand staircase leads to the second floor which showcases three large bedrooms (two with ensuite baths and water views), and a charming fifth bedroom and a hobby room are found on the third floor. The lower level includes a media room, laundry room, exercise area and spa, complete with steam shower and sauna. All systems have been updated including electrical and plumbing, geothermal HVAC, encapsulated crawlspace under the rear patio, and conditioned side crawlspaces. Located 1.5 hours from D.C. and Baltimore, 2 hours from Philadelphia, and 3.5 from New York, “Wheatlands” presents a rare opportunity for the most discerning buyer. Minutes to Easton (noted for its fine dining, shopping, theatre, art galleries, jet-airport, and year round enjoyment) by car and St Michaels by boat, this beautiful property has it all! Additional photos and video of the property are also available upon request. Exclusions and a right-of-way do apply.

8588 Wheatlands Rd, Easton

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

3 Beds 2 Baths
Top location off Bailey's Neck, Road about three miles from Easton and seven miles from Oxford. Fabulous water views. Year-round sunsets. Setback line shown on old plat was changed to accommodate existing residence; new plat included in documents. New Baily Marine dock is included in the sale (waiting on State permit since February). Do not go out on the existing dock; danger of falling through. Cove is kept dredged to 3 to 4 ft MLW. Dredged depth continues to dock. Buyer may test depth to Buyer's satisfaction. Shoreline is fully rip-rapped. Seller had the well capped off and had Delmarva disconnect the electric service. By deeded covenant no short-term rentals are allowed at Peachblossom Point. House needs a major renovation but was well built in 1977. Needs new kitchen, windows, bathrooms, flooring, probably remove the wall between kitchen and family room. But the house has an excellent floorplan. All carpet has been removed. High land, sandy soil. 2024 perk for 5 bedrooms is awaiting review and approval by TCDeptEH.. All appliances are included but offered in AS IS CONDITION, probably not working. Seller is tagging some heirloom shrubs that are excluded from the sale, to be moved in the Fall.

6648 Peachblossom Point Rd, Easton

Listing courtesy of Shoreline Realty. Contact: 410-822-7556

3 Beds 2 Baths
This coastal-style 2-bedroom, 1-bathroom home is thoughtfully adorned with a "Beach Theme" to create a tranquil ambiance, perfect for relaxation. Additionally, the property includes a charming 1-bedroom, 1-bathroom cottage, offering extra space for guests or rental opportunities. For a total of 3 Bedrooms, 2 Full bathrooms. The updated kitchen features stainless steel appliances, a full-size fridge, hardwood floors, and a breakfast bar. Through-out you will see the attention to detail. Hardwood floors through-out the entire home, ceiling fans, and updated A/C. Outside, a spacious backyard provides ample room for outdoor enjoyment. This property has too many updates to list. Convenient driveway parking for two cars is available on the right side of the shared driveway and street parking is in front of the home. A spacious fenced in backyard completes the property and all new siding. For water enthusiasts, the Chesapeake Bay and its tributaries are just a short drive away, providing opportunities for kayaking, crabbing, and sailing. Nearby, explore the charming and historical towns of Easton, Oxford, St. Michaels, and Cambridge. The location is also proximate to Annapolis and local beaches, including Rehoboth Beach in Delaware and Ocean City in Maryland. Additionally, public golf courses are available in the vicinity. This delightful property blends coastal charm with modern conveniences and is ideal for those seeking a serene coastal lifestyle.

215 Tred Avon Ave, Easton

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

3 Beds 3 Baths
Welcome to this mid-century waterfront home, nestled on a high elevation along the serene Miles River. This charming property boasts three bedrooms and three full bathrooms, providing ample space and comfort for you and your family. The home features a timeless mid-century design, blending classic architecture with the potential for modern updates. Recently, new roof, siding and windows have been added, enhancing the home's durability and aesthetic appeal. One of the standout features of this property is the private dock, ideal for boating enthusiasts or simply enjoying the scenic waterfront. Whether you’re looking to relax by the water, entertain guests, or embark on river adventures, this home offers it all. Situated between the charming towns of Easton and Saint Michaels, this location offers the perfect balance of tranquility and accessibility. Enjoy the convenience of nearby shops, dining, and recreational activities while relishing the peace and privacy of waterfront living. Don't miss the opportunity to own this exceptional waterfront home on the Miles River. With some updates, it can become your dream retreat. Schedule a viewing today and experience the unique blend of mid-century charm and waterfront living for yourself.

27261 Arrowhead Trl, Easton

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

3 Beds 2 Baths
150 Feet of WATERFRONT PROPERTY to Enjoy the beautiful Sunrises and the most Amazing SUNSETS right from your very own PIER! Nestled along the tranquil waterfront of this Miles River tributary, this Charming 3 Bedroom, 2 Bath, 1 level Cottage offers an idyllic retreat on a sprawling 1 Acre level lot! The timeless allure of the all Brick exterior, seamlessly blends with the natural surroundings, enhancing the picturesque setting here on Glebe Creek. As you approach the property, you are greeted with a beautiful decorative fenced entrance and a manicured lawn. Get ready for the Fantastic and unobstructed Water Views as you enter inside! Enjoy the comforts of this cozy home with real Hardwood floors throughout, fresh Professional Paint, a Gas Fireplace and a Sunroom which is complemented by new windows that invite abundant natural light! The 2 bedrooms are generously sized with ample closet space and the Primary Bedroom boasts an Ensuite with dual sinks, a walk-in closet, a shoe closet and great Views to wake up to every morning! Outside, the expansive backyard extends to the Waterfront, providing a serene Oasis for outdoor activities, entertaining, and enjoying the beauty of nature like watching Blue Herons, Osprey, Bald Eagles, Geese, Ducks and more! The Newer extended 6-foot-wide Pier is complete with a boat lift and jet ski lift along with a very desired floating dock perfect for fishing and crabbing, a swimming platform, SUP, Kayak and canoe launch... all on 3 Feet MLW! Whether relaxing or grilling on the Deck, gardening in the spacious yard, or embarking on water adventures, the possibilities for leisure and recreation are endless! The one car Garage and the Shed are perfect for storing all your "toys" and the extensive Driveway will host many Cars. Conveniently located yet secluded enough to enjoy privacy, this Home is a nice blend of a Peaceful Retreat and an Entertainers delight! Perfectly placed in between Downtown Easton and the famous small Town of Saint Michaels, both just minutes away for all of your shopping and dining needs!

8997 Glebe Creek Rd, Easton

Listing courtesy of RE/MAX Executive. Contact: (443) 274-1900

3 Beds 3 Baths
Welcome to your home with exceptional views of the Choptank River. Nestled on 3.36+/- acres, this property offers a waterfront lifestyle with shoreline access, perfect for launching your kayak and exploring the waters. This spacious home features 3 bedrooms and 2.5 bathrooms, providing ample space for comfort and hosting family or friends. The primary suite includes en-suite bathroom with soaking tub, separate shower, an access to private balcony with water views, ideal for relaxation. Living room with fireplace and formal dining room with views of the river. The den off the kitchen, complete with a built-in bookcase, offers a cozy nook for reading or work while also taking advantage of the beautiful water views. The versatile upper-level bonus room can serve as a recreation room or office. Outdoor living is easy with a screened-in porch off the kitchen and a patio, ideal for entertaining or unwinding as you take in the scenery. The 2-car garage provides convenient parking and storage. Fiber optic internet available through Easton Velocity.

9199 High Banks Dr, Easton

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

2 Beds 2 Baths
Discover unparalleled charm and modern comfort at 31 S Aurora St., located in the heart of Easton’s Historic District. This beautifully renovated home offers a blend of historical elegance and contemporary upgrades. Renovations include a new roof, insulation, and foundation, along with an encapsulated crawl space and mini-split systems. The kitchen boasts new stainless-steel appliances, a gas stove, custom black walnut countertops, and new cabinets, creating a culinary haven. Enjoy the convenience of a new washer/dryer combo and the luxury of two new bathrooms. The two spacious bedrooms feature ample closet space and vaulted ceilings. Throughout the home, exposed beams add a touch of rustic charm. Outside, a well-maintained yard with a rear entrance and a new fire suppression system ensures safety. This exceptional residence is perfect for those seeking an in-town lifestyle in Easton, MD. Please note that some photos are virtually staged for illustration purposes.

31 S Aurora St, Easton

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

3 Beds 4 Baths
Immaculately Renovated, Beautiful Historic Home enhanced with Many Modern Features and Amenities! Located in Easton's Historic District, steps from Downtown and across the street from The Country School Private Academy. NEW Roof and Shingles, Restored Original Cedar Lap Siding and Fish-Scale Accent Siding. New Solid Mahogany Front entrance. NEW Mahogany Stained Wrap-around Front Porch Deck. New Heart Pine Floors throughout. 3 1/2 All NEW Bathrooms. Master en suite with Separate Soaking Tub and Shower. NEW Kitchen with Large Center Island, Shaker Style Cabinets, Quartz Countertops, Cast Iron Porcelain Sink, Brass Faucet, Stainless Appliances including: French Door Refrigerator with Ice & Chilled Water, and Gas Range, Microwave & Dishwasher. Dedicated Laundry Room off the kitchen. Historically Accurate Trim throughout, New Jen Wen Wood Clad Windows, NEW Electrical from the street/POLE and throughout the house. NEW Plumbing throughout the house. Tankless Water Heater. NEW HVAC w/ Dual Zone Climate Control System on all three levels. NEW Driveway connecting from the front street to the access road in the back. Carriage House with restored exterior.

641 Goldsborough St, Easton

Listing courtesy of Keller Williams Realty Centre. Contact: 4103120000