Royal Oak Homes with Pool

Royal Oak Homes with Pool

Welcome to Royal Oak, Maryland, a hidden gem nestled in Talbot County that offers a perfect blend of serene living and vibrant community spirit. This picturesque town is surrounded by the stunning landscapes of the Eastern Shore, where the Chesapeake Bay meets charming rural settings. With its rich history, friendly neighborhoods, and a plethora of outdoor activities, Royal Oak is an ideal place for families and individuals seeking a tranquil yet engaging lifestyle.

One of the standout features of homes in Royal Oak is the availability of properties with pools. Imagine basking in the sun by your own private oasis during warm summer days, or hosting memorable gatherings with friends and family around a sparkling pool. These homes offer not only a refreshing escape but also an opportunity to create lasting memories in the comfort of your own backyard.

Royal Oak's real estate market showcases a diverse range of homes, from quaint cottages to expansive estates, many of which are designed to complement the area's natural beauty. Whether you’re a first-time homebuyer or looking to invest in a vacation retreat, you’ll find properties that cater to your unique preferences and lifestyle.

In addition to the allure of homes with pools, Royal Oak boasts proximity to the stunning waterways of the Chesapeake Bay, where boating, fishing, and kayaking are just a stone's throw away. With its charming atmosphere, welcoming community, and beautiful homes, Royal Oak is not just a place to live; it’s a place to thrive. Come explore the possibilities and discover your dream home in this enchanting town!

Newest Royal Oak Homes with Pool

$6,995,000
7 Beds 6 Baths
Introducing White Swan Point, an exceptional Chesapeake waterfront estate offering one of the Eastern Shore's most commanding settings. Positioned at the confluence of Broad Creek and the Choptank River, the property enjoys nearly 5,000 feet of shoreline with sweeping western and southwestern vistas that capture spectacular sunsets, cooling summer breezes, and an ever-changing panorama of sailboats, yachts, and waterfowl. Less than two hours from Washington, D.C., this private waterfront retreat offers a rare combination of architectural quality, recreational opportunity, and lasting investment. Whether envisioned as a family compound, executive retreat, or waterfront residence for entertaining on a grand scale, the setting delivers an experience that is increasingly difficult to replicate along the Chesapeake Bay. Constructed in 2006 by its builder as their personal residence, the approximately 8,500 square foot home reflects enduring craftsmanship and design throughout. Seven ensuite bedrooms provide generous accommodations for family and guests, while soaring ceilings, three fireplaces, richly appointed living spaces, and a sunlit morning room create an atmosphere that is both elegant and welcoming. A distinctive turret crowns the residence, providing a remarkable vantage point from which to enjoy the sunset as it settles across Broad Creek. Outdoor living is at the heart of the estate. Expansive terraces, waterside porches, and beautifully landscaped gathering spaces transition naturally toward the shoreline, where the pool, pool house, outdoor kitchen, and riverfront fire pit become the backdrop for unforgettable evenings overlooking the water. Nearly every outdoor amenity has been carefully positioned to take advantage of the property's extraordinary western exposure and uninterrupted water views. For the boating enthusiast, the estate offers exceptional privacy and water access along Broad Creek, providing an ideal setting for cruising to St. Michaels, Oxford, Tilghman Island, and destinations throughout the Chesapeake Bay. Approximately 1,900+/- feet of stone revetment protects the prominent shoreline, while an additional 2,500+/- feet along the quiet waters of Bridge Creek remains preserved in its natural state, creating a diverse waterfront environment rich with wildlife and native vegetation. Beyond the residence, the property continues to offer remarkable flexibility. Approximately 13 acres are under cultivation with an additional 3.5 acres in pasture, presenting opportunities for equestrian pursuits, hobby farming, or simply preserving the estate's open landscape. A substantial 40-foot by 60-foot barn includes workshop space, equipment storage, and a second-floor caretaker or guest apartment, providing exceptional utility for managing the property or accommodating extended stays. White Swan Point represents far more than an extraordinary waterfront home. It is an opportunity to own one of Maryland's signature Chesapeake estates, where privacy, recreation, architectural quality, and timeless waterfront living come together in one exceptional offering.

24390 Deep Neck Farm Ln, Royal Oak

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

$6,495,000
4 Beds 5 Baths
Irish Creek Waterfront Estate Set along more than 1,000 +/- feet of pristine, navigable waterfront on Irish Creek, this remarkable 22.14 +/- acre waterfront estate captures the very essence of luxury living on Maryland’s Eastern Shore. Surrounded by sweeping southwest-facing water views and unspoiled natural beauty, the property offers exceptional privacy and scale just minutes from the charming towns of Easton and St. Michaels. Approached by a long, private paved drive, the stately Colonial residence blends timeless architecture with comfortable sophistication, designed for both elegant entertaining and relaxed waterfront living. Inside, refined interiors feature rich hardwood flooring, extensive crown molding, custom built-ins, and four wood-burning fireplaces, creating warm gathering spaces throughout the home. The main level is thoughtfully designed for hosting and everyday living, with gracious formal and informal spaces that flow effortlessly together. A formal dining room, expansive living and family rooms, and a well-appointed kitchen with island and pantry create the perfect setting for gatherings with family and friends. The main-level primary suite offers a peaceful retreat with its own fireplace, walk-in closet, and spa-inspired bath. Upstairs, three additional bedrooms and two full baths comfortably accommodate guests for extended weekends on the Shore. Outdoors, the estate unfolds as a private waterfront retreat designed for unforgettable weekends and celebrations. Spend warm summer days by the Gunite pool and outdoor spa, gather around the built-in fire pit at sunset, or enjoy a friendly match on the bocce court. A tranquil pond and expansive grounds enhance the sense of serenity, while the vaulted three-season porch provides the perfect vantage point for watching boats drift by and taking in the breathtaking evening sunsets over Irish Creek. The property is exceptionally well-suited for hosting, with a charming pool house and a separate two-bedroom guest apartment above the detached four-car side-entry garage—ideal for visiting family, weekend guests, or extended stays. Located in the coveted Royal Oak waterfront community, and within easy reach of Easton, St. Michaels, and the Chesapeake Bay, this extraordinary offering is less than two hours from Washington, D.C., Baltimore, and Philadelphia, making it the perfect luxury retreat for weekend escapes or year-round living on the Eastern Shore. Here, life slows down—boating at sunset, long summer weekends with family and friends, and the timeless beauty of Chesapeake Bay living.

24679 Deep Neck Rd, Royal Oak

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

$2,095,000
6 Beds 4 Baths
**Discover Your Waterfront Oasis in Royal Oak** Nestled in the charming town of Royal Oak, these exceptional waterfront properties present breathtaking views of Oak Creek, conveniently located near the Miles River and the renowned Chesapeake Bay. Positioned between the picturesque communities of Saint Michael’s and Easton, this rare gem boasts approximately 541 feet of pristine water frontage, enhanced by a newly installed bulkhead as of summer 2025. Comprising two distinct parcels, both properties offer expansive water vistas that are truly captivating. Imagine enjoying serene afternoons by one of the two existing pools, each perfectly situated to overlook the tranquil waters. Each home is equipped with its own dedicated well and is connected to public sewer, ensuring convenience and reliability. Elevated above flood risks, this property requires no flood insurance, providing peace of mind for future owners. The first residence, a charming brick rancher at 7049 Acorn Alley, features single-story living with three bedrooms and 1.5 baths, set on a generous .81 acres. Built in 1963, it offers 1,454 square feet of cozy, inviting space. Across the way, the colonial-style home at 7047 Acorn Alley boasts four bedrooms and two full baths, nestled on .73 acres. Constructed in 1975, this expansive 1,920-square-foot residence provides ample room for family gatherings and entertaining. Ideal for outdoor enthusiasts, this location is a paradise for boating, fishing, kayaking, and paddle boarding, with calm waterways that invite exploration. The property is also perfect for bird watching and cycling, making it an ideal haven for nature lovers. Whether you envision a lucrative investment, a serene vacation retreat, or the canvas for your dream home, the endless possibilities await. Centrally located in Talbot County, with easy access to Easton, Baltimore, and the DC metro area, as well as a short ferry ride to Oxford, this property is a unique opportunity not to be missed. Embrace the lifestyle you've always desired and make this waterfront paradise your own.

7049 & 7047 Acorn Aly, Royal Oak

Listing courtesy of McClain-Williamson Realty, LLC. Contact:

$5,000,000
3 Beds 4 Baths
Now offered at an improved price of $5,000,000. Excellent opportunity to own your own private Eastern Shore estate in Royal Oak. Anderby Hall, part of an original 1680 land grant, spans a breathtaking 12+/- acre parcel featuring 3,260’+/- of rip-rapped shoreline. This exceptional property includes a tidal pond, a private cove, and an exclusive island peninsula accessed by bridge. Pass through the gated driveway to discover the main residence: a 3,000+/- sq. ft. Colonial showcasing a great room with a fireplace, charming old pine floors, hand-hewn ceiling beams, and a granite island kitchen. The luxury primary suite features his-and-her closets alongside a second-floor office/den. Nearly every room frames gorgeous, unobstructed views of Irish Creek. Outside, brick walkways lead to a spectacular waterside pool. Boaters will love the private dock offering 5' MLW, located just minutes from the Choptank River. Additional amenities include a 2,600 sq. ft. guest house, tennis courts (easily convertible to pickleball) with a gazebo, a 30x50 detached 3-car garage, an additional 1-car garage with a workshop, new well, and a service shed. Complete with a licensed shoreline and abundant local wildlife (geese, ducks, deer, and turkey), this estate is convenient to Easton and St. Michaels. Experience an unmatched lifestyle of luxury, privacy, and waterfront beauty at an incredible new value.

5499 Anderby Hall Rd, Royal Oak

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

Start Your Search