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5084 Ferry Neck Rd, Royal Oak
$3,950,000
4 Beds ⋅ 4 Baths
Tucked within a canopy of trees along Maryland’s Eastern Shore, this remarkable home rests quietly beside the Choptank River. The setting feels worlds away, eighty acres of meadows and woodland that open gently to more than 1,800 feet of private shoreline, where a western exposure captures breathtaking sunsets reflected across the water. The residence at 5084 Ferry Neck Road was shaped by owners whose careers in fine contemporary art inspired a deeply thoughtful approach to design, one that explored geometry, light, and proportion with an almost abstract eye. The resulting octagonal plan draws the landscape into every room, creating a calm rhythm of space and view. A low, horizontal brick façade settles the home into its surroundings, while a lifted roofline and generous overhangs give shelter and balance. Inside, a sweeping staircase curves upward through the central volume, a graceful gesture that anchors the home with quiet strength. In 2024, the property underwent a comprehensive renewal. Porcelain countertops, new glazing, and refined lighting bring a fresh modern sensibility while honoring the original architecture. Approached by a long, tree-lined drive, the home reveals itself gradually, first a glimmer through the woods, then an opening to water and sky. Beyond its immediate beauty, the land itself offers a rare opportunity, with the potential to create a divisible waterfront homesite should the next owner wish to explore it. What remains most striking, however, is its sense of comfort, a home that is inviting, shaped by art, nature, and time.

5084 Ferry Neck Rd, Royal Oak

Listing courtesy of TTR Sothebys International Realty. Contact:

Selling Office: Non Subscribing Office.

25610 Chance Farm Ct, Royal Oak
$3,350,000
5 Beds ⋅ 6 Baths
Perfectly nestled on 4.96± private waterfront acres between Easton and St. Michaels, this extraordinary estate embodies the very best of Eastern Shore living, anchored by rare deep water dockage (6’+ MLW) for the ultimate Chesapeake boating lifestyle. This Royal Oak home’s western exposure offers amazing sunset views across Solitude Creek.This listing also includes a fully prepaid 96-year recorded ground lease on an adjoining 5.48± acre parcel of land -- featuring a picturesque wildflower pasture, a mature 4± acre maple orchard, and charming outbuildings (detached garage and red barn) -- creating unparalleled privacy, beauty, and tranquility. A winding, tree-lined private drive sets the tone for the peaceful retreat that awaits. Inside, panoramic water views fill nearly every room, while the recently updated home blends timeless elegance with warm, inviting comfort. Soaring ceilings, rich hardwood floors, exquisite custom moldings, and expansive living spaces create an atmosphere that is both refined and welcoming. The formal living and dining rooms, each centered around a cozy fireplace, offer inviting spaces for memorable gatherings and celebrations. The light-filled family room features dramatic volume ceilings, oversized windows, a fireplace, and stunning waterfront views that bring the outdoors in. Designed for both everyday living and effortless entertaining, the gourmet kitchen features slate flooring, stainless steel appliances, a walk-in pantry, and a waterside breakfast area where every meal is paired with breathtaking scenery. The luxurious main-level owner’s suite is a private sanctuary with its own fireplace, spectacular water views, dual walk-in closets with custom built-ins, and a spa-inspired bath designed for relaxation. Upstairs, guests and family are comfortably accommodated with a spacious bedroom suite, two additional guest bedrooms, and a versatile bonus room ideal for a home theater, fitness studio, or playroom. Above the oversized, air-conditioned three-car garage, a separate guest retreat with a kitchenette, full bath, and private balcony with beautiful waterfront views offers the perfect space for visiting friends and family. Outdoor living is equally exceptional. A sprawling slate patio, recently added waterside pool, and enclosed porch with vaulted ceilings and flagstone flooring create inviting spaces to relax, entertain, and take in the serene surroundings. Set on a peninsula with more than 1,000 feet of shoreline, the property offers remarkable privacy and endless water views in seemingly every direction. A private deep water pier on Solitude Creek makes boating effortless and permits a memorable arrival by water for your guests. Enoy fishing and crabbing and direct water access to the Choptank River and Chesapeake Bay. Rarely does a property so gracefully combine timeless architecture, resort-style amenities, and one of Talbot County’s most coveted waterfront settings into a place that truly feels like home.

25610 Chance Farm Ct, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Century 21 Redwood Realty.

25320 White Hall Rd, Royal Oak
$2,850,000
4 Beds ⋅ 3 Baths
"WHITEHALL FARM" 99 +/- exclusive Talbot County waterfront acres. Property consists of four parcels including three platted SDA's and over 2000 ft of shoreline bordering Irish Creek. MLW water depth average 2-3 ft. Parcels 1 and 3 percs are currently in re-evaluation process with the county. Parcel 2 improvements include a 2784 sq ft 4 bd 3 bath farmhouse and an updated BAT septic along with two 40 x 35 storage barns. 37 +/- tillable ag acres make up the interior of the farm. Timberland acres span 38 +/- acres upon the entryway with a mix of loblolly pine and hardwood. A 2 acre freshwater pond and a 5 acre plant and flood impoundment serve as crucial habitat for wintering waterfowl. This property is well suited for a large family compound in a highly desirable area of Talbot County and offers unlimited amenities. Conveniently located 10 minutes from St. Michaels, 15 minutes from Easton, and a short drive to the Oxford/ Bellevue Ferry, you will find several restaurants, shops, and activities nearby.

25320 White Hall Rd, Royal Oak

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Anne Arundel Properties, Inc..

5837 Irish Creek Rd, Royal Oak
$2,750,000
4 Beds ⋅ 4 Baths
Absolutely stunning mid-century contemporary estate offering a private , park-like setting, with heated swimming pool, pavilion, luxurious fully equipped outdoor- kitchen, outdoor shower, in -ground hot tub ,tennis court, and maintenance -free Azek pier with new 30K lb. boat lift. Meticulously maintained inside and out! Professionally landscaped with WiFi controlled front/rear irrigation system.The superbly designed and crafted home offers an open floor-plan with 4 bedrooms and an office, 3.5 designer baths with heated floors,, a magnificent gourmet kitchen, upper and lower level living areas providing outstanding functionality. Breathtaking water- views and protected shoreline! This is an outstanding turn-key property that comes beautifully furnished !

5837 Irish Creek Rd, Royal Oak

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

Selling Office: TTR Sotheby's International Realty.

5440 Ferry Neck Rd, Royal Oak
$2,500,000
5 Beds ⋅ 6 Baths
Welcome to ‘Drake’s Landing’! Beautifully sited on 20 picturesque acres on the shores of Irish Creek, this 4,602 sq. ft .completely renovated (2021) waterfront estate offers the perfect blend of casual elegance and thoughtful design. The main level welcomes with expansive water views and features a guest bedroom with ensuite bath, a cozy family room (or den/office), and a gracious living room anchored by a large brick hearth and woodburning fireplace. The gourmet kitchen is the center of the home - outfitted with upgraded appliances, a center island with breakfast bar, and additional dining space. Adjacent is a second kitchen - ideal for effortless indoor/outdoor entertaining. A formal dining room and large waterside sunroom complete the main living spaces. Upstairs, two spacious primary suites anchor each end of the home, offering privacy and comfort, with two additional guest bedrooms (one with ensuite bath) and a hall bath in between. Step outside to enjoy westerly water views from the elevated deck, or gather on the enclosed screened porch, perfect for crab feasts and sunset dining. Outdoor amenities include a charming 2BR/1.5BA guest cottage (540 sq. ft.), a new dock with two slips, stunning waterside pool, waterside firepit, and barrel sauna. A 3-bay equipment garage is connected to an enclosed game room and workshop - creating a complete retreat for relaxation, recreation, and unforgettable waterfront living. The property with its acreage is also great for hunting. This is Eastern Shore living at its best – spacious, serene, and set up for year-round enjoyment. *Furnishings may be available for sale.

5440 Ferry Neck Rd, Royal Oak

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

Selling Office: Benson & Mangold, LLC.

24878 W Ferry Neck Rd, Royal Oak
$2,495,000
3 Beds ⋅ 3 Baths
This exceptional waterfront cottage is set on two private acres and offers sweeping sunset views over the Choptank River to the Chesapeake Bay. Completely renovated from crawl space to roof, the home features over 2,600 square feet of beautifully finished living space with three bedrooms and three full baths. The interior showcases renovated kitchen and baths, complemented by extensive custom finish-work throughout. There is a detached garage with metal roof and second floor storage and gravel circular driveway with ample parking. Improvements on this home include an encapsulated crawl space, new roof, siding, multiple premium sliding glass doors and windows, all valuable upgrades that enhance both style and energy efficiency. The grounds have been thoughtfully transformed with curated shrubs, trees, and perennials that highlight the existing landscape, concrete pool, and pergola, creating an ideal setting for outdoor relaxation and entertaining. Enjoy easy boating access just 10 minutes to Oxford and 15 minutes to Tilghman, while by land the property is ideally situated between Easton and St. Michaels. Enjoy the protection of high property elevation (no flood insurance required) with a sturdy rip-rapped shoreline, beautiful sandy bottom, and a private L pier with two new boat lifts. 24878 W. Ferry Neck Road offers the perfect blend of privacy, comfort, and Eastern Shore waterfront living on the Choptank River. List of the many recent improvements in document section of this listing.

24878 W Ferry Neck Rd, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

26090 Royal Oak Rd, Royal Oak
$2,000,000
4 Beds ⋅ 5 Baths
Welcome to Terrapin Point, an extraordinary waterfront estate nestled in the heart of Royal Oak, Maryland—one of Talbot County’s most coveted and picturesque settings. Built in 1890, this timeless Victorian residence evokes the charm of a bygone era, blending old-world elegance with the serene beauty of Maryland’s Eastern Shore. Set gracefully on a private point along the tranquil waters of Oak Creek, the property offers sweeping, uninterrupted waterfront views and a rare sense of peace and seclusion. With minimal boat traffic and protected waters just off the Miles River, Terrapin Point is a true sanctuary for those seeking quiet coastal living and the wonders of nature. A long, tree-lined driveway creates a grand and memorable approach, opening to a storybook setting reminiscent of a Norman Rockwell painting. The home itself is filled with natural light and architectural character, including soaring ceilings, elegant archways, and a stunning dining room with exposed beams that overlooks the water—perfectly framing the estate’s breathtaking surroundings. Designed for both relaxation and entertaining, the home features a spacious kitchen and dining area ideal for hosting, along with an oversize screened porch that invites you to unwind while enjoying gentle breezes off the creek. Outdoors, a beautifully positioned in-ground pool sits just at the water’s edge, offering a resort-like vacation experience. On the edge of the trees sits a beautifully designed potential "glamping" cabin, art or music studio where you can enjoy the birds singing and watch the light through the trees. Perfectly located, the property sits equidistant between the charming towns of Easton and St. Michaels, allowing effortless access to renowned dining, shopping, and cultural attractions while maintaining a peaceful, tucked-away feel. The 12 acre point of land and home embodies the quintessential Eastern Shore lifestyle—refined yet relaxed, elegant yet inviting. A rare offering where timeless architecture, premier waterfront, and an exceptional location come together to create a truly unforgettable property. *Seller currently resides at the property in the main floor primary suite. Several pictures have been visually enhanced with virtual staging.

26090 Royal Oak Rd, Royal Oak

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

Selling Office: TTR Sotheby's International Realty.

25714 Edgeview Rd, Royal Oak
$616,000
4 Beds ⋅ 2 Baths
Looking for space, privacy, and a backyard made for easy living? This property delivers! Located in the highly desirable Royal Oak area, this private 2.4± acre retreat offers the perfect balance of peaceful living and convenience to Easton and St. Michaels. Enjoy a fenced in-ground swimming pool and surrounding patio. The interior was freshly painted and has new carpet throughout. There is a cozy living room with fireplace, separate dining room, sunroom and an large kitchen with breakfast area & island. Featuring four bedrooms and two baths, including a spacious primary suite with two walk-in closets and updated bath, this one level home is designed for comfort. Separate laundry room with utility sink, washer, dryer, built in ironing board and plenty of cabinetry A detached two-car garage with loads of storage space, enclosed area for lawn gear, and separate changing area with access from the pool completes the package. Close to county boat ramp, park, beach and Oxford/Bellevue Ferry. On public sewer!

25714 Edgeview Rd, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

6980 Hopkins Neck Rd, Royal Oak
$560,000
4 Beds ⋅ 3 Baths
Welcome to the charming village of Royal Oak where this beautifully crafted Cape cod style home - just 5 years young- offers the perfect blend of modern comfort and timeless design. Featuring a desirable first floor primary suite, this home includes 4 bedrooms and 3 full baths providing flexibility for family and guests alike. It sits on a large 1 acre lot and backs to woods for privacy. Just minutes from historic Easton or St. Michaels. The large 2 car garage is heated and cooled making it ideal for a workshop, hobby area or just a fun hang out spot. Garage also has a TV in it. The kitchen has granite counters and upgraded appliances and is open to the living room. There is also a covered front porch for an additional place to relax and enjoy the slower pace of life on the Eastern Shore. Additional highlights include low maintenance vinyl siding and an encapsulated crawlspace for enhanced efficiency and peace of mind. .

6980 Hopkins Neck Rd, Royal Oak

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

Selling Office: Benson & Mangold, LLC.

6745 Edge Rd, Royal Oak
$525,000
3 Beds ⋅ 2 Baths
Water Access • Ideal Location • Assumable Loan at 2.375%! Welcome to 6745 Edge Road, a well-maintained 3-bedroom, 2-bath home nestled in the quiet waterfront community of Royal Acres. Located at the end of a cul-de-sac and directly across from the community dock, this property makes it easy to enjoy the Chesapeake lifestyle with convenient access to the water. Fully renovated and thoughtfully expanded, the home provides additional living space while maintaining the convenience of one-level living. Ideally situated near St. Michaels, Easton, and Oxford, you’ll have easy access to local shops, restaurants, galleries, marinas, and waterfront attractions. Inside, the home features beautiful hardwood floors, a spacious kitchen with ample cabinetry, granite countertops, stainless steel appliances, and a large island. The living room includes a gas fireplace and built-in shelving, while the screened porch provides a comfortable place to relax and enjoy the outdoors. The large backyard offers plenty of room for entertaining, gardening, recreation, or simply enjoying the peaceful surroundings. Royal Acres is a voluntary HOA with a community boat ramp and boat slips, providing convenient access for boating, fishing, and enjoying time on the water. Downtown St. Michaels is less than 5 miles away, and the Bay Bridge is approximately 35 miles away. Whether you’re looking for a full-time residence, weekend retreat, or a place to enjoy the Chesapeake lifestyle, this property offers the best of Eastern Shore living, with comfortable one-level living, water access, a convenient location, and the peace and quiet of a small waterfront community.

6745 Edge Rd, Royal Oak

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

Selling Office: Redfin Corp.

7033 Thorneton Rd, Royal Oak
$375,000
Two dwellings on one property. 7031, 7033 Thorneton Road- Freshly painted with new LVT flooring upstairs. The dwellings share a well and have county sewer hookup- 7033 is the front building and has 3 bedrooms and 2.5 baths upstairs and a great room with handsome kitchen, powder room , screened porch and deck. There is also a roof deck off the primary bedroom and the property overlooks a preserved farm field in front. 7031, is entered by walking around to the back door off the deck overlooking a nice stand of woods and offers privacy. Inside you will find a great room and first floor bedroom and bath. There is a large attic area that could be developed into additional living space. In between the dwellings there is a covered run in shed with parking for three cars and an additional storage shed for storage. The property has been successfully rented for many years with satisfied long term tenants. Tenants have moved and property is ready for move in.

7033 Thorneton Rd, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Meredith Fine Properties.

5658 Gates St, Royal Oak
$365,000
3 Beds ⋅ 2 Baths
Nestled in the heart of the charming waterfront village of Bellevue, 5658 Gates Street presents a rare opportunity to own a classic home rich in historic charm. This thoughtfully maintained residence blends timeless character with everyday comfort, offering approximately 1,480 square feet, 3 bedrooms, and 2 bathrooms. Inside, you’ll find beautifully preserved hardwood floors and the peace of mind of a recently updated roof. The true highlight, however, is the setting. Located in the quaint Bellevue community, this home is surrounded by the natural beauty and unhurried pace that define Maryland’s Eastern Shore. Just moments away, enjoy access to the scenic Tred Avon River, nearby public landings, parks, and the iconic Oxford-Bellevue Ferry. Whether you’re savoring peaceful evenings, biking to the water, or taking a short drive to Saint Michaels or Easton for dining, shopping, and local events, this location offers an ideal blend of tranquility and convenience. Perfect as a full-time residence or weekend retreat, 5658 Gates Street captures the true essence of Eastern Shore living.

5658 Gates St, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

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