Earleville Homes with Pool

Earleville Homes with Pool

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Newest Earleville Homes with Pool

$445,000
3 Beds 2 Baths
Professional photos coming 7/25! Experience the charm of Chesapeake Haven with this beautifully renovated 3-bedroom, 2-bath home offering 2,576 square feet of flexible living space and breathtaking Chesapeake Bay views. With extensive renovations completed in 2024 and brand-new bedroom windows installed in 2025. This home seamlessly blends modern updates with timeless coastal charm. One of the home’s most unique features is its versatile floor plan. The first level offers two bedrooms, a full bath, a spacious great room, and a convenient laundry area, while the second level features the main bedroom with an en-suite bath, along with the kitchen, dining area, and living room. This thoughtfully designed layout provides incredible flexibility for multigenerational living or simply creating separate living spaces to fit your lifestyle. The moment you step inside, you’ll be captivated by the abundance of front-facing windows that frame stunning Chesapeake Bay views throughout the main living areas, filling the home with natural light and allowing you to enjoy the water from the comfort of your own home. Whether you’re enjoying your morning coffee or unwinding at sunset, the ever-changing views create a truly peaceful setting. Situated on a generous 0.58-acre lot, the property also features an oversized detached garage with electric; a spacious driveway with ample parking, a fenced yard perfect for pets and FOUR decks (one on each side of the home, one in the front - ground level, and one in the rear) offering multiple outdoor spaces to relax, entertain, soak in the scenery, or enjoy the refreshing bay breeze. A cozy fireplace in the main living adds warmth and character indoors, while the outdoor shower can currently be connected via an exterior hose or it could also be permanently plumbed if desired. Living in Chesapeake Haven means embracing the best of waterfront living, with easy access to boating, fishing, parks, local dining, and shopping…all while enjoying the tranquility of this sought-after water-oriented community. This beautifully updated home offers the perfect combination of comfort, flexibility, thoughtful updates, exceptional outdoor living, and spectacular Chesapeake Bay views. Don’t miss your opportunity to make it yours!

16 Kent Ave, Earleville

Listing courtesy of Gregg Team Realty. Contact:

$8,995,000
6 Beds 5 Baths
Set on 93 private acres with 6,100 feet of shoreline along the picturesque Sassafras River and Cox Creek. The estate includes a main house, guest house, pool house and riverside pavilion, offering ample delightful space for large groups to gather, unwind and experience the activities and natural beauty of the upper Chesapeake. Showcasing exceptional design, materials, craftsmanship, the living spaces are framed by expansive views of the Sassafras River. The main residence includes six spacious bedrooms and four and a half baths. The heart of the home is a gourmet kitchen and adjacent generous breakfast room wrapped in 180-degree river views, a setting that enhances every meal. The home flows naturally into multiple large gathering spaces built for entertaining, and into quieter, more intimate rooms designed for reflection and rest. The guest house ensures that you can accommodate family and friends. With three generously sized bedrooms and one and a half baths, full kitchen, fireplace and brick patio, it offers a self-contained retreat that gives guests their own space while keeping everyone together on the estate. The pool complex redefines what a backyard amenity can be. At its center is a 52,000-gallon swimming pool with a retractable electric cover, positioned to frame sweeping panoramic river views. An adjoining heated spa and a oversized pool deck complete a setting that invites long, unhurried afternoons in the sun. Elevating the experience further, it offers a full bath, generous living and dining areas, and amenities more commonly found at a high-end resort - a large, well-equipped gym and an eight-person steam room -providing the perfect end to an active day. Perched at the water's edge, the recently constructed two-story pavilion is the social and recreational heart of the estate's waterfront. It's a front-row seat to everything that makes the Sassafras River so beloved: working crab boats in the early morning, sailboats gliding past at midday, and the sky turning gold over the water at dusk. Spend a lazy afternoon on the pavilion's upper level as the river life unfolds below, then head down to launch your own boat from the private boat lift or boat ramp. The Sassafras and Cox Creek offer boundless activities including boating, water skiing, tubing, wakeboarding, sailing, paddleboarding, and kayaking, all awaiting just steps away. After fun on the water, return to the pavilion for lunch, dinner, or simply a seat with one of the best views on the upper Bay. Adjacent to the grassy wharf, the nearly 1,000-foot private sandy beach is a rare and remarkable amenity ideal for an afternoon stroll with friends or a quiet moment watching the sunset or moon rise over the river. Other improvements along the waterfront include a 1000+ stone revetment protecting the shoreline, a 13,000lb boat lift, and a boat ramp. The grounds reflect a thoughtful balance of beauty, privacy, and long-term stewardship, with carefully planned enhancements designed to complement the natural setting while supporting comfortable estate living. Mature trees and established landscaping create a sense of arrival and continuity across the property, while curated sightlines and open lawn areas transition naturally into wooded edges and surrounding countryside. A network of trails invites exploration through the woods, offering quiet vantage points and seasonal changes that reinforce the property’s connection to the Eastern Shore landscape. The property's blend of fields, woods and waterfront habitats, complemented by offshore hunting rights offers productive hunting. The land supports healthy populations of deer, wild turkey, ducks & geese, creating a sportsman's haven throughout the seasons. Enjoy fishing and crabbing from the dock ideally located on the edge of the deep water channel. Major mid-Atlantic cities, international airports & train stations are within easy reach, making the estate accessible for full-time residents and weekend escapes.

750 Cassidy Wharf Rd, Earleville

Listing courtesy of Gunther-McClary Real Estate. Contact:

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