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$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:

$39,995
2 Beds 1 Baths
Boaters Dream, You Have Your Own Year Round Boat Storage! Open Access To The Community Boat Launch And A Cottage With Open Floor Plan; 2 Bedrooms, 1 Bath, With Large Kitchen, Dining Room, Den And Very Large Living Room That Allows For Additional Sleeping Area, With Central Air Conditioning, Large Deck, Several Outbuildings And Plenty Of Parking On The Spacious Double Lot That Backs To Wooded Area With Beautiful Shade Trees. Located In The Indian Acres Gated Community. It’s a Great Vacation Get Away With So Much To Do Or Just Relax. The Golf Cart Friendly Community Makes For Getting To The Pools And Waterfront a Breeze! Plus, Boat Ramp, Lake, Two Ponds, Convenience Store (With Great Food), Arcade And So Much More. Come See All That This Community Has To Offer. This Purchase Includes Two Lots. (Golf Cart Is For Sale Separately) This Is A Campground Where YOU OWN YOUR OWN LOT, But Not A Full Time Residence, It Is Limited To 150 Days A Year, No More Than 100 Consecutive Days. You Will Never Need To Spend Another Vacation in Someone Else's Home - VACATION IN YOUR OWN HOME ALL SUMMER LONG!!! And You Can Even Come For A Winter Retreat, As The Park Is Open Year Round!!! Call Today For An Appointment!!!

50-55 Pequot-Sauk Ln Unit #GLEN 8, Earleville

Listing courtesy of Key Realty, Incorporated. Contact:

$39,950
2 Beds 1 Baths
Boaters Dream, You Have Your Own Year Round Boat Storage! Open Access To The Community Boat Launch And A 2 Bedrooms, 1 Bath, 1991 Single Wide Mobile With CAC, Large Deck, Two Outbuildings And Plenty Of Parking On The Spacious Concrete Driveway. Located In The Indian Acres Gated Community. It’s a Great Weekend/Vacation Get Away With So Much To Do Or Just Relax. Golf Cart Friendly Community Makes For Getting To The Pools And Waterfront a Breeze! Plus, Boat Ramp, Lake, Two Ponds, Convenience Store (With Great Food), Arcade And So Much More. Come See All This Community Has To Offer. This Purchase Includes Two Lots. Boat and Golf Cart Are Negotiable. This Is A Campground Where YOU OWN YOUR OWN LOT, But Not A Full Time Residence, It Is Limited To 150 Days A Year, No More Than 100 Consecutive Days. You Will Never Need To Spend Another Vacation in Someone Else's Home - VACATION IN YOUR OWN HOME ALL SUMMER LONG!!! And You Can Even Come For A Winter Retreat, As The Park Is Open Year Round!!! Call Today For An Appointment!!!

230 & 231 Arapho Ln Unit #GLEN 8, Earleville

Listing courtesy of Key Realty, Incorporated. 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:

$2,200,000
5 Beds 6 Baths
Welcome to where dreams come true in an exclusive Waterfront neighborhood located in Sunset Pointe, Earleville MD....This stunning 2 story Sprawling Ranch is on 19.32 acres of breathtaking views of fields, wildlife and the open waters of Pond Creek. This meticulously renovated property featuring a beautifully redesigned family room with a wood-burning fireplace that has been tiled from floor to ceiling with custom tile, also featuring electric blinds just added to the specular windows that take all the views in.... The kitchen boasts new Bosch appliances, granite counter tops, wine refrigerator, counters galore, sub zero refrigerator, new above lighting cabinets, instant hot water at the sink, new sink and so much space... The Large dining area leads to an expanded deck with composite flooring and stone pillars. The office/sunroom which is located off the kitchen area has beautiful full glass etched french doors fireplace that compliments the family rooms...The solid door off this room that has a designer staircase down to the lower level patio ....As you walk through the kitchen there is a half bath that is located next to the large mudroom with another door that exists to another new deck expanded also with composite floors and an overhang.....This mudroom has space for everyone .... separate locker area and a dogs haven with a doggie water bowl filler....Now lets head back to the other side of the family room ....Welcome to the primary suite that has it's own gazebo deck private to you with sliding glass doors that also exit from this suite....This newly renovated primary bathroom has heated floors, custom cabinets, large Jacuzzi tub including an oil diffuser and automatic dryer ....marble shelve with a TV .... the shower will WOW you with a shaving station with it's own faucet and mirror....and custom tiling like no other.... The laundry room is outside of the the primary bedroom with all custom closets and is conveniently within access of the other first floor bedrooms .....Bedroom 2 and 3 on the first floor have custom closets and share a jack and jill bathroom with stunning updates....also another Jacuzzi and walk-in shower. Now lets head back to the foyer and down to the lower level .....First you are greeted with a large game room that has beautiful sliding doors out to the new salt water pool ....This lower level has 2 full bathrooms one that is handicap-accessible and connects to a beautiful 4th bedroom with it's own set of sliding glass doors leading out to a lovely patio....Wait!!! there is more.... a theater room features great a 100 inch screen, movie lights, platform seating with counter top seating to eat your popcorn... decorated with great design and to top it off a kitchenette completes this impressive space..... Are you ready to step outside and see this impressive yard.....again the New salt water pool, the dyed concrete decking around the pool, the hardscaping, landscaping, and a wood trellis with planting features..... Additional highlights include a full house generator, invisible dog fence, and outdoor lighting. This property is a truly a one-of-a-kind gem! Just in case that was not enough to impress here are 2 more features....The large 3 car garage has new door openers, and above it is an efficiency apartment has been fully renovated with high ceilings and small kitchenette, new small deck, new large full bathroom ...did I mention this studio has wood walls that are from ........This is also a hunters enclosed 2 person deer blind, great fishing and crabbing a great outdoors persons dream.....10 acres are currently being farmed agriculturally..

248 Pond Creek Ln, Earleville

Listing courtesy of Patterson-Schwartz-Middletown. Contact: 3022855100