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$2,995,000
3 Beds 5 Baths
"Cypress Lodge" - Tucked away on a private waterfront lot along the Tred Avon River, this striking contemporary-style residence offers expansive water views, exceptional privacy, and thoughtfully designed indoor-outdoor living. The 3-bedroom, 5-bath home features an open floorplan filled with natural light, highlighted by soaring vaulted cathedral ceilings and clean architectural lines that create a bright, airy feel throughout. Designed to embrace its waterfront setting, the home seamlessly connects spacious living areas with multiple outdoor entertaining spaces overlooking the river. The well-thought-out outdoor living space was designed to fully maximize the property’s incredible waterfront setting, complete with a pool, outdoor fireplace, and covered pavilion overlooking both the pool and the water. Whether hosting guests or enjoying a quiet evening at home, the outdoor spaces offer a seamless extension of the home’s contemporary design and relaxed Eastern Shore lifestyle. Additional exterior amenities include a private dock, private tennis court, and hot tub, all surrounded by mature landscaping and a peaceful setting that enhances the property’s sense of seclusion. Ideally located just outside of Easton, the property provides convenient access to Washington, D.C., Baltimore, and Philadelphia, making it an exceptional full-time residence or weekend getaway within reach of several major metropolitan areas.

6906 Travelers Rest Cir, Easton

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

$2,395,000
4 Beds 4 Baths
Due to personal reasons, BUYER had to withdraw offer--Inspections were "better than good" according to inspector. LOCATION, CHARM, and beautifully RENOVATED!!!Set on 2.32 glorious acres overlooking Dixon Creek, this beautifully and lovingly maintained 1915 residence offers timeless character, refined comfort, and exceptional waterfront living. Original hardwood floors run throughout much of the home, while expansive windows bathe the traditional floor plan in natural light and frame expansive water views from nearly every room. The main level features gracious formal living and dining rooms, a gourmet kitchen with a beautiful center island and top-tier stainless appliances, and a welcoming family room with wood-burning fireplace. Custom built-ins are thoughtfully integrated throughout the home, reflecting quality craftsmanship and attention to detail. Upstairs, the waterside primary suite offers a fireplace, dual walk-in closets and a luxurious ensuite bath with soaking tub and glass-enclosed shower. Two additional guest bedrooms include one with an ensuite bath and another with access to the hall bath. The third level provides a small loft style BR /flexible bonus room, ideal for an office or studio. Outdoor living is equally inviting, with a waterside screened porch, a poolside screened patio with wet bar, and an additional open deck off the dining room—perfect for enjoying the tranquil setting. The beautifully landscaped grounds feature mature trees, lush plantings, and extensive hardscaping, anchored by a gunite pool with expansive deck and surrounding gardens. Additional structures include a charming former icehouse (currently used as a storage shed) and a larger outbuilding once used as tenant quarters. An attached 2-car garage and a full encapsulated basement offer excellent functionality and versatility. With 280 feet of natural shoreline, a private pier with two slips, boat lift, and 3.5–4' MLW, this property captures the essence of Eastern Shore waterfront living. *Roof- 2011, new siding, new boiler, renovated kitchen and baths, redecked pier. -Septic replaced in 2020 and is for 4 bedrooms-owners have plans for proposed first floor primary suite where existing south side porch currently is.

8075 Leehaven Rd, Easton

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

$4,395,000
4 Beds 6 Baths
Irish Tides offers a quintessential Eastern Shore retreat with luxury and style. This beautifully crafted 4-bedroom, 5.5-bath main house provides captivating views of the Miles River from almost every room. The main level has been enhanced with a new HVAC system and ductwork, ensuring comfort and efficiency throughout. Exquisite crown moldings, hardwood floors, and custom built-ins add an inviting elegance. Enjoy formal living and dining areas, chef’s kitchen with an island, quartz countertops, and a scenic waterside dining nook for informal meals. The family room, with its soaring cathedral ceilings and gas fireplace, flows through a light-filled hallway with cozy seating, offering direct views of the river. New roof installed in 2026. The main-level primary suite features a cathedral ceiling, built-ins, and a private patio, while its spa-like en-suite includes abundant natural light, a jetted soaking tub, marble accents, and two generous walk-in closets. The home also features a newly encapsulated basement and crawlspace, ensuring a well- maintained environment year-round. The professionally landscaped grounds set the stage for a well-equipped pool house complete with a guest room, kitchenette, sitting area, and bathroom. The outdoor space also boasts an in-ground pool with a spacious patio, outdoor shower, and grill area. A private pier with a boat lift offers approximately 4' +/- MLW, a 300' +/- shoreline, and a private beach. For added convenience, the main house includes attic storage and a storage shed, while the 3-car detached garage features a bonus room—perfect for an office or rec room—with kitchenette. All of this is just a short drive from Easton’s dining, shopping, and airport access.

27029 Miles River Rd, Easton

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

$3,999,900
4 Beds 7 Baths
Swan Point is an exquisite waterfront estate set on approximately 4.5 acres, offering sweeping westerly views across the Tred Avon River. A gated, paved driveway with cobblestone curbs welcomes you to this private retreat. This stately Colonial features 4 bedrooms, 4 full baths, and 3 half baths, thoughtfully designed for both intimate living and grand entertaining. The formal living room, complete with a wood-burning fireplace, opens to a charming three-season porch. A separate formal dining room provides an elegant setting for gatherings. The gourmet kitchen includes a breakfast area and adjoining den with a wood-burning fireplace and 600-year-old heart pine floors that are radiant-heated. A spacious sunroom extends from the kitchen and flows seamlessly onto a brick patio with a built-in grill and is just steps from an inground, heated pool with spa and brick surround. A separate laundry room with powder room, and an attached two-car garage finish off the main level. The partially finished basement offers additional living space with a wood-burning fireplace, full kitchen, and powder room. A private staircase leads to the primary suite, located in its own secluded wing, featuring two walk-in cedar closets and a luxurious bath with soaking tub and separate shower. The main staircase leads to additional bedrooms, including a second primary suite, a third bedroom with hall bath, and a fourth bedroom with a sitting room and en suite bath. Outdoors, a large dock with seating area offers approximately 4’ MLW, water, electric, and two boat lifts. The partially rip-rapped shoreline enhances both beauty and stability. The spacious carriage house includes room for collector cars, an office with gas fireplace and wet bar, a conference room or flex space, and a powder room. A three-car detached garage offers additional storage with a guest apartment above. Equestrian enthusiasts will appreciate the barn with four stalls, office, tack room, and abundant loft storage, along with three paddocks for horses. A workshop with wood stove and powder room provides the perfect space for woodworking or creative pursuits. A second entrance offers convenient access for horse trailers or boats. Swan Point combines timeless elegance, comfort, and versatility—all set against one of the Eastern Shore’s most captivating waterfront backdrops. 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.

27473 Westpoint Rd, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272