5 Signature Maryland Estates from Annapolis to Ocean City Views

On one of Annapolis’s most desirable streets in Murray Hill, this 1913 residence pairs formal sophistication with a complete custom renovation from just a few years ago—thoughtfully updated with modern luxuries, including an elevator. Set on a double lot, the home offers a rare private driveway, a two-car garage, and a separate storage room. Indoors, high ceilings, crown and dental molding, custom cabinetry, and two fireplaces bring a sense of tradition, while a state-of-the-art kitchen with two dishwashers and first- and second-floor laundry rooms supports everyday ease. Electric window blinds, two HVAC zones, and a full-service security system with cameras add quiet practicality. A screened-in porch looks out to a fully fenced yard with irrigation and mature landscaping, creating a calm backdrop for daily life.

Surrounded by 42 acres adjacent to the historic Wye Heights Plantation, this stately Easton estate pairs a grand sense of scale with an unmistakably tranquil setting. Inside, soaring ceilings and meticulous detailing set a refined tone, while an elevator offers easy movement across multiple levels. Designed for both quiet weekends and larger gatherings, the residence includes a fully finished basement with a cozy pub and kitchenette—an inviting backdrop for evenings in. A guest apartment over the garage provides private quarters for family or friends. Outdoors, a picturesque pond and charming bridge anchor the landscape, with garden views enjoyed from an enclosed garden sunroom and an additional sunroom off the breakfast area. Screened-in porches on both main and upper levels extend living space through the seasons, framing a daily rhythm of nature and history.

Along the water’s edge on the Wye River, this Norman Jaffe–designed estate unfolds across 5+ private acres on the river’s widest stretch. Floor-to-ceiling glass reinforces a seamless indoor-outdoor rhythm, drawing panoramic water views into nearly every room. Inside, Tennessee Quarry Flagstone, rich hardwoods, and wood-clad ceilings set a grounded, tactile tone across expansive living areas, with an office, elevator, and a screened porch for long river-facing evenings. The 2017-renovated gourmet kitchen centers on an oversized island and premium finishes, while upstairs the primary suite pairs a dramatic wall of glass with a fireplace, dual walk-in closets, and a spa bath. A fully reimagined 4BR/4BA guest house (2017) adds a full kitchen and sweeping views. Outside: a 22’x44’ heated PebbleTec pool, pool house, Bradford hot tub, and a 340’ pier with lift and deep-water access—an Eastern Shore day, perfectly composed.

On a residential street in Bethesda’s beloved Greenwich Forest, this offering centers on possibility: a lot where you can build a dream home in collaboration with award-winning Mid-Atlantic Custom Builders. With construction not yet commenced, the experience begins at the design table—working alongside Mid-Atlantic’s designers and architects to shape a home that reflects how you want to live, room by room and detail by detail. The listing imagery is illustrative only, showing an example of a home to be constructed, and Option 1 of the floor plan appears among the photos. Three total floor plan options are available in the documents section, giving a clear starting point for tailoring the final vision. It’s a rare chance to create something personal in an established Bethesda neighborhood.

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Along the water’s edge in Berlin, this custom-built three-story residence is paired with the next-door lot, creating an expansive, private setting surrounded by wetlands and panoramic water views toward the Ocean City, Maryland skyline. Inside, an open floor plan unfolds across three levels with six spacious bedrooms and 4.5 elegantly appointed bathrooms, balancing everyday ease with room to gather. A gourmet kitchen anchors the main living spaces, while several cozy dens and multiple living areas offer quiet corners for reading, conversation, or hosting. Five fireplaces add warmth and rhythm throughout the home, and a dedicated office supports work-from-home days without compromise. Private balconies extend the experience outdoors, framing serene waterfront sunrises and sunsets that make each day feel intentionally paced.