Property Listings - Waterfront Homes

Set on 2.48 scenic acres along the Elk River, this well-maintained brick waterfront home offers the perfect blend of comfort, privacy, and outdoor living. With three bedrooms and two additional included lots, the property provides a rare opportunity for expanded space and serene surroundings. Enjoy direct water access with a 100-foot dock featuring two boat lifts, a floating jet ski dock, water, electric (220V and 110V), and a convenient sink—ideal for boating enthusiasts. Inside, the home welcomes you with a cozy living room with a fireplace, while the kitchen showcases tall cherry cabinetry offering abundant storage. Radiant heating throughout most of the home ensures year-round comfort. The spacious great room flows seamlessly into a screened porch and out onto the deck, creating the perfect setting to relax and take in the peaceful waterfront views. The lower level features an Endless Pool, providing a private space for exercise and recreation. Whether enjoying quiet mornings or breathtaking sunsets over the river, this property offers exceptional waterfront living in every season.

Price: $1,290,000

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Coming Soon! Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with a deeded boat slip.  3.55 acres, partly wooded, exceptionally landscaped, and perfectly framed water views. Walk down to the water to enjoy the views or launch a kayak.  The deeded deep-water boat slip, outfitted with a boat lift, is just a short distance away. The home features 4 bedrooms and 4 full bathrooms, plus a large loft that could be an additional bedroom. The large eat-in kitchen has expansive windows that perfectly frame the water view. A great spot for entertaining! Doors in the kitchen lead to the waterfront deck, spanning the front of the home.  In both sitting rooms, you’ll find fireplaces that have been conveniently updated to propane. The first-floor primary bedroom opens up to the waterfront deck and offers a fantastic water view, as well as a large bathroom that was recently updated.  Upstairs you’ll find two waterfront bedrooms, one with its own attached bath and ample closet space.  Downstairs, there are two additional full bathrooms and a bedroom. Above the kitchen sits the light-filled loft, a great office, studio, or extra bedroom.  The exterior has a generous front porch, outdoor shower, circular drive, 2-car garage, fenced dog run, and additional garage space connected to the basement.  This light-filled waterfront property is located 15 minutes away from the waterfront community of Rock Hall and historic Chestertown.

Price: $1,450,000

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Completely renovated four-bedroom home offering an ideal Upper Eastern Shore location where Swantown Creek meets the Sassafras River. This private retreat features convenient first-floor living, with water views from the living room, dining area, kitchen, and two primary bedrooms. The home is enhanced by a spacious deck overlooking the water, a finished basement, outdoor shower, hot tub, fire pit and a detached storage shed. Set in a park-like setting, the property is just minutes from Middletown, DE and the bypass, providing easy access to northern destinations while still enjoying the charm of of nearby Georgetown and Chesapeake City.

Price: $918,000

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Well - maintained colonial home situated on over 12 + private acres along Piney Creek, complete with your own pier - perfect for canoeing, fishing or kayaking. This 3 bedroom homes features an eat-in kitchen with marble countertops, opening to a spacious deck where you can relax and take in the peaceful wooded surroundings. The main level also offers a cozy den with fireplace, a separate dining room, and a family room just off the the kitchen - ideal for everyday living and entertaining. The unfinished walk - out basement provides endless potential for additional living space, a workshop or recreation area. The property is beautifully landscaped with mature trees, creating a secluded setting. A short walk or a fun gator ride takes you down a cleared path to the water's edge. Located on a quiet street with only four homes, this is a rare opportunity to enjoy privacy, nature, and waterfront living all in one.

Price: $969,000

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www.cassidywharffarm.com Cassidy Wharf Farm Sassafras River Estate Extended Cassidy Wharf Farm Video 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, a large pool house 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.

Price: $8,995,000

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Experience riverfront living on the Sassafras River with this exceptional home on just over 13 acres. There’s room for everyone with 5/6 bedrooms, 3 full baths, and two kitchens. Enjoy sunrise over the river through the primary bedroom’s expansive window, then watch the eagles and osprey while sipping coffee on the dock. This home boasts a jet ski dock, and both fixed and floating docks with 3 feet mlw. Take the boat to dinner at any of the five riverfront restaurant options, or catch your own dinner on the Chesapeake Bay. There’s plenty of off river activities as well, with 20x40 in-ground saltwater pool, pickleball court, spacious yard, outdoor shower, firepit, and woods. In summer, the 5 acre wildflower field bursts into color, inviting quail, butterflies and songbirds of every sort. With very easy access to points north and south, you can easily spend a day in Annapolis or zip less than 60 miles to the Philadelphia airport. The booming community of Middletown is 15 minutes away, with unlimited restaurant and shopping options. This stunning residence provides an ideal retreat for nature lovers and outdoor enthusiasts alike. Store all your toys in the attached garage and the large outbuilding. Imagine unwinding on your private dock as you enjoy friends and family playing/boating on the river. Launch your kayak or standup paddleboard directly from the property's floating dock. Relax and cool off in the pool after a great day on the river or an invigorating pickleball game. Inside, spacious living areas feature expansive windows that take full advantage of breathtaking water views, creating a light-filled and welcoming atmosphere throughout the home. Every detail has been designed for comfort, convenience, and fun, making this riverfront oasis a truly special place to call home.

Price: $1,975,000

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Welcome to Silly Manor, a Chesapeake Bay-front property with an abundance of coastal charm and panoramic views. This home is perfectly situated on the coveted Lawton Avenue, one of Kent County's most sought-after neighborhoods. Enjoy stunning sunsets all year-round and direct access to the dynamic waters of the Chesapeake Bay. The open living and dining space offer spectacular views of the Chesapeake. The kitchen opens up to the patio and garden, and has a spacious island for entertaining. The home was designed with a first-floor primary suite, offering convenient (and hard-to-find) one-floor living. There are two additional bedrooms and a full bath on the second floor. Watch the boats glide in and out of Swan Creek all day long, or enjoy the cozy fireplace during the colder months, with the Bay sparkling just outside. This is one of the larger parcels on Lawton, and it boasts a detached, oversized one-car garage, along with a separate workshop. The hardscape patio and stone walkways are perfect for al fresco dining or simply soaking in the surrounding beauty. The home feels very private, yet is located just minutes from many marinas, restaurants, shops and the Rock Hall Beach. This is the perfect weekend retreat or full-time home!

Price: $1,100,000

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**To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or evening cocktails. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

Price: $849,900

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Experience the allure of waterfront living with this stunning condominium, perfectly situated to offer breathtaking views of the Chesapeake Bay and the Rock Hall Harbor. Inside, you are greeted by an inviting ambiance, accentuated by updated kitchen and flooring that seamlessly blend style and functionality. Whether you’re an aspiring chef or simply enjoy the art of entertaining, the modern kitchen is designed to inspire culinary creativity, boasting stainless steel appliances and ample storage space. Just up the stairs you will find two large guest bedrooms, washer and dryer, and a full bathroom. The primary bedroom is located on the third level with a view of the Bay. You'll love the large private balcony overlooking the Chesapeake. The primary bathroom has a soaking tub as well as a shower, and a walk-in closet with ample space for storage. This residence is located a short stroll from marinas, a vibrant array of restaurants, and downtown shops. Easy access to festivals throughout the summer and fall, enjoy a delightful day out or a cozy evening at your favorite eatery. The charm of this location is not just limited to daytime adventures; it transforms into a magical setting at night! The best part is the unobstructed views of spectacular 4th of July fireworks, all from the comfort of your own home. This condominium offers relaxation and convenience while taking in all the charms of Rock Hall. With a focus on comfort, every corner is thoughtfully designed to cater to your needs, blending modern amenities with the natural beauty of its surroundings. Don’t miss the opportunity to make this beautiful condominium your own! Embrace the coastal lifestyle and let the Chesapeake Bay become your new escape.

Price: $545,000

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Virtual Waterfront Home on the Upper Chesapeake Bay/Elk River! Enjoy breathtaking sunsets! Experience expansive water views from nearly every room in this exceptional 5 bedroom, 4 1/2 bath contemporary home situated on the banks of the Elk River. Designed for comfort and style, the open floor plan is filled with natural light and features a striking floor-to-ceiling stone gas fireplace in the great room - perfect for cozy gatherings. The main level offers a spacious master suite with its own fireplace, a sliding door to the back deck, and serene water views. The kitchen is outfitted with granite countertops and flows into the dining area and sunroom, both with easy access to the deck. Upstairs, a loft overlooks the water and separates two generously sized bedrooms, each with its own full bath - ideal for guests or family privacy. The finished lower level is an entertainer's dream, complete with a full kitchen, media/theater room, and two additional bedrooms with walk - out access to the covered patio. Additional features include a two - car garage with an upper storage area, plus a separate rear garage for water toys and equipment. A deeded boat slip with lift at the community beach is included - perfect for enjoying all the river has to offer.

Price: $1,700,000

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Discover the luxury of coastal living with this masterpiece waterfront property located in a much sought-after location on the Chester River. When entering the home, you’re immediately greeted in the elegant foyer that opens to a formal dining room to the right, and an office to the left that could easily be converted to a first floor bedroom. The fully renovated chef’s kitchen features state-of-the-art appliances, a spacious island, and ample cabinetry, making it perfect for hosting both large parties and intimate gatherings. The expansive living room features a fireplace and full views of the sparkling waterfront. This meticulously renovated home features 3 bedrooms, each with an en suite bath. The second floor boasts a relaxing combination of a screened porch and an open deck spanning the full front of the house and overlooking the river. The very large primary suite, with it's pampering bath, also has an entrance to the inviting screened porch. When stepping outside, the gracious landscaping calls for you to unwind on the open deck and work on your tan, or step onto your own private dock and explore the river a bit. There is also a covered brick patio, perfect for firing up the grill and eating al-fresco. Located just minutes from local shopping and schools, this paradise offers you a life of convenience, without compromising privacy and luxury.

Price: $1,495,000

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Waterfront Home on the Elk River!
Enjoy breathtaking views as ships from around the world pass by. This spacious home offers 4+ bedrooms and 3 full baths, with incredible potential to make it your own. Main Level: 2 bedrooms, a great room with a fireplace, a dining area, and an eat in kitchen. Upper Level has 2 additional bedrooms with a full bath. Walk-Out Lower Level has plenty of extra room for storage, entertainment, or additional living space. The community's active engagement is evident through events like the annual 4th of July celebrations at the beach, fostering a close-knit and vibrant neighborhood atmosphere. Don’t miss this rare opportunity to own a waterfront property with stunning views and endless possibilities!

Price: $920,000

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Step into this nearly new, impeccably maintained two-bedroom townhouse located in the highly desirable Chester River Landing community. Recent upgrades make this home truly turn-key, perfect for those seeking comfort and style. Relax and entertain all summer long on the beautifully designed screened-in porch, ideal for enjoying warm evenings and gentle breezes. On the second floor, the spacious primary deck boasts expansive views of the Chestertown skyline and treats you to breathtaking summer sunsets—your personal oasis in this vibrant community. Just a short stroll away, you'll find the charm of Historic Downtown Chestertown and the scenic Wilmer Park, offering the perfect blend of convenience and lifestyle. Chester River Landing is a coveted water-access community offering a host of amenities, including an in-ground pool, two grilling and dining areas, and ample community space. Enjoy the large community dock with boat slips available for sale or lease—a dream for boating enthusiasts. Don't miss this opportunity to own a piece of Chester River Landing paradise!

Price: $579,000

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A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own ground level storage. This is a unique setting offering waterfront living in downtown historic Chestertown and includes off street parking. Walk to downtown restaurants and shops. Beautiful southeast views of the Chester River with spectacular sunrises and plenty of year-round sunshine. Take in the all of the nearly year-round waterfront activities from your own back yard, including Chestertown Tea Party, 4th of July fireworks and Sultana down rigging weekend. Located on Maryland’s scenic eastern shore less than 85 miles from Washington DC to the south or Philadelphia to the north, this home is the perfect meeting spot for those living in the Mid-Atlantic region. 5 Units ranging from 1-2 bedrooms

Price: Starting @ $385,000

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Four parcels totaling 52 acres. Introducing Holly Point - an incredible private waterfront estate on a point of land with over 2800 feet of waterfront, comprised of five parcels and improved by a spectacular custom designed 5 bedroom main residence built with the finest materials and an impressive attention to detail as well as a charming 3 bedroom guest house with excellent waterviews of its own. A large detached garage/shop, additional detached workshop/gaming building with a bath room, and green house add to the first rate amenities. Every aspect of this property was meticulously planned and is beautifully oriented. From the stunning drive in through a park-like setting to the mature landscaping throughout the property, the expansive water views, easy access to the water, trails throughout the woods, prime hunting habitat, privacy but not isolation all make this a truly one of a kind offering. You can also purchase this property with a perc approved 38 acre lot for $5,600,000. Check out the property video below: https://vimeo.com/834171714

Price: $4,995,000

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A rare offering of an in-town waterfront parcel offering incomparable views from a point of land on the Chesapeake Bay. The house is valuable for the large footprint it provides (would not be able to build at this size on this lot otherwise. ). Town water and sewer, the public beach just steps away, sunsets and the sparkling Bay at your door. House needs extensive renovation and you will be required to build first level to higher flood code regulations. renovation permits/regulations need to be verified with the Town of Rock Hall by the Buyer

Price: $750,000

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Stately waterfront Victorian home rich in history with endless possibilities depending on your needs or desires. Original home built in the late 1800’s could be redesigned to its original grandeur. Currently the building is a six-unit multifamily property offering plenty of potential. The entire first floor and part of the lower level is a large approximately 2,700 square feet “owners’ home” that was recently renovated with top quality materials and redesigned to take advantage of the waterfront living this building offers. There are also five other units providing income and cost sharing, including a one-bedroom garden apartment on the lower level and two additional one bedroom units on both the 2nd and 3rd floors. The five apartments have separate entrances from the first-floor apartment and provide a gross monthly income of $5000. Investors will appreciate the 6-unit rental with an approximate cap rate of 5.75%. This is a unique setting offering waterfront living in downtown historic Chestertown and includes off street parking. Located on Maryland’s scenic eastern shore less than 85 miles from Washington DC to the south or Philadelphia to the north, this home is the perfect meeting spot for those living in the Mid-Atlantic region. Beautiful southeast views of the Chester River with spectacular sunrises and plenty of year-round sunshine. There is a recently installed deep water fixed/floating dock with two new boat lifts.

Price: $1,295,000

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Can your investments pay these dividends. Sassafras River Compound uniquely centered in between New York City, Philadelphia, Baltimore and Washington DC. Less than one hour from Philadelphia International Airport. 17 bedrooms 16.5 baths, 1900's renovated Manor house with spectacular down river views and summer sunsets. Perfect location for plenty of water sports, Water skiing, Wakeboarding, Sailing, Paddle boarding and fishing. Just minutes by boat to Georgetown Harbor, with 5 restaurants. Must see to appreciate, but make sure you block out enough time to see all this Upper Eastern Shore gem has to offer.

Price: JUST REDUCED! $5,200,000

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Completely renovated 4 bedroom waterfront condominium located in the heart of historic Chestertown. 2 boat slips, adjacent to Wilmer Park and a few block from the main commerce area of the town including shopping and restaurants. Condominium renovations include but not limited to new kitchen, new baths, hardwood floors throughout, new dock, recently replaced roof, new HVAC systems just to name a few.

Price: REDUCED! $1,398,000

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Beautiful home private home situated on Still Pond creek, with 20 acres of land to spread out on and 550 feet of waterfrontage. Recently renovated kitchen with Viking appliances. Great for large family gatherings and cooking. Wrap around deck and back yard, wonderful for entertaining family, friends, and extended family. Two large out buildings for waterfront toys and any other projects.
Come see this great property!
OPEN HOUSE 12/4/2021 NOON-2

Price: $1,498,000

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THE COVE - 385 feet of waterfront shoreline, wrapping around two sides of this property, located in a premier boating destination. Large rancher, one-floor living on Long Cove. Very easy access from here to the Chester River and the Chesapeake Bay. The property has a rare offering of it's own wide boat ramp, along with bulkheading and dockage. Protected waters - your boat will be safe here during heavy weather. There is an adorable "boat-house" at the water's edge, perfect for storing all your water toys, decoys, or use as an art studio. The combination of an ample screened porch leading to a large deck, overlooking a beautiful lawn and water views, makes this the perfect location for fun parties or just quiet relaxing, and of course boating excursions. The house is surrounded by waterviews from the porch, the kitchen, the family room, into the primary bedroom. There is a cozy wood stove in the large den which has a cool retro "hunter's lodge" vibe. Serviced with public sewer, no septic to worry about. Would make a fantastic vacay rental. Exceptional opportunity for an active waterfront lifestyle just five minutes from downtown Rock Hall and 15 minutes to Chestertown. Just under two hours in either direction to Baltimore, Philadelphia, DC, Wilmington, South Jersey.

Price: $825,000

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Enjoy endless water views, breathtaking sunsets and easy access to the water from this four bedroom home that provides many of the highly sought after features of an Easter Shore waterfront property. This property also has a bulkheaded and rip-rapped shoreline, a blend of open lawn and mature shade trees and is in a great location by water.  Easy boating access on the Chester River with close proximity to the Corsica River, Langford Creek, or even Kent Island and just a short drive from Chestertown and Rock Hall.

Price: $945,000

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Welcome to North Point Marina. This well-established marina and motel is ideally located behind the jetty wall at the entrance to popular Rock Hall Harbor from the Chesapeake Bay. There are 138 total slips, including 26 covered slips, with room for large yachts on the T heads. All of the slips are equipped with water and electric--30, 50, or double 30 AMP. Nearly 80% of the slip occupancy is comprised of seasonal rentals, leaving plenty of room for transients. Robust Wi-Fi network extends throughout the facility making working from your boat a breeze. North Point Marina features the only fuel dock on Rock Hall Harbor. Five room motel offers amazing views of the Bay. The motel books throughout the year with a waiting list during the Summer. Adjacent to the motel is a two bedroom, 1 bath apartment with private porch. Live where you work. Numerous amenities—bay front pool, large pavilion for events, ample parking, slip holder/guest bathrooms, pump out, ship’s store, storage space, office/flex space, slip holder lounge. Many additional opportunities for revenue. North Point Marina is an immaculate, impeccably maintained facility.

Price: $3,995,000

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Spacious and meticulously maintained in water access community of Elk Forest. This home offers 4 bedrooms with plenty of recent upgrades. Large great room off of the kitchen with attached deck, perfect for everyday living and great entertainment space. Flag lot location gives a very private location, but still part of a community, walkout basement with superior wall construction and great game room that includes a pool table. Two car garage and bonus storage space below offers plenty room for all of your waterfront toys. Community offers several waterfront access points with a transient dock and a marina with slips available on a annual lottery basis. Very easy access to point north less than 1 hour to the Philadelphia Airport, just minutes from Middletown, DE.

Price: $671,000

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Enjoy panoramic, Chesapeake Bay views from nearly every room in this renovated 4 bedroom, 3 1/2 bath home sitting on .8 waterfront acres in Huntingfield Estates, just outside of Rock Hall. Main level with open floor plan makes entertaining a breeze. Large deck and balcony are the perfect spots to take in amazing sunsets. Master bedroom features include bathroom, large walk-in closet, and balcony access. Flex room is perfect for home office or craft room. Downstairs you will find three additional bedrooms with slider access to backyard, two full baths, laundry and mudroom. There is plenty of storage in the two-car garage. Bonus space under deck for kayaks and paddleboards. Only a few minutes to Eastern Neck Island, marinas, Rock Hall Harbor, and Main Street. Make this place your home!

Price: $650,000

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Check Out the Property Video Below:
https://vimeo.com/465055907

Price: $1,500,000

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Enjoy sweeping water views from three sides of this spectacular property.  The custom built sprawling ranch home offers first floor living, is ideally situated on a point of land that provides broad water views, a private dock with protected water and easy access to the Chesapeake Bay, mature shade trees and gardens, a large deck overlooking the water, a guest house that is located close to the main house but can not be seen from the main house and has a separate driveway. Guest house can be sold fully furnished. This is a rare offering that one must see to truly appreciate all that it has to offer.<br />View Property Video Below:<br /><a href="https://vimeo.com/353792186">https://vimeo.com/353792186</a><br />This House was also featured on The Chestertown Spy's House of the week for 10/29/19. Check out the article below.<br /><a href="http://chestertownspy.org/2019/10/29/house-of-the-week-all-decked-out-by-jenn-martella">http://chestertownspy.org/2019/10/29/house-of-the-week-all-decked-out-by-jenn-martella</a>

Price: $999,000

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A diamond in the rough with nearly all the desired features for waterfront property. Broad expansive 180 degree southwesterly views of Langford creek, four season sunsets, protected dock and slip. Crabbing, fishing, wake boarding, water skiing, paddle boarding, sailing all in your back yard. Just a few minutes from historic downtown Chestertown and very easy access to points north, Philadelphia and Wilmington or south, Washington DC and Northern Virginia.

Price: $749,000

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Panoramic views abound from this lovely home in Huntigfield Estates just 2 mi outside of Rock Hall. This gorgeous 3 bed/2.5 bath home is situated on a peninsula with the Chesapeake Bay on one side and the Huntingfield Creek on the other. Sip a cocktail on one of the screened porches or the water's edge and watch the magnificent Rock Hall sunsets. Dock site with a sandy beach and gradual slope perfect for kayaking and smaller watercraft. Rip rap shorelines and sheltered beach area. Lovely gardens and plantings. A rare property and a definite must see. <br />View Property Video Below: <br /><a href="https://vimeo.com/339138544">https://vimeo.com/339138544</a>

Price: $795,000

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Best of all worlds for this 4 bedroom completely renovated home (2017 New kitchen, bathrooms, dock and steps just to name a few) located on Mill Creek/Sassafras River. Less that one hour from Philadelphia airport with easy access to route 213 for points north, Wilmington and Philadelphia, or south to Annapolis and DC. Walking and boating distance to all five of the restaurants located on the Sassafras River.

Price: $898,000

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A beautiful residence on the Bay. Exquisite sunsets, in-ground pool, a grand upper-floor great room with a large deck offering expansive views. Also an elegant first floor master suite with it's own spacious porch facing the bay side. Kitchen is designed for serious entertaining. Historic charm blended with a modern sensibility.<br />View Property Video Below:<br /><a href="https://vimeo.com/339134539">https://vimeo.com/339134539</a>

Price: $895,000

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<span>Very private 3 bedroom home in park like settling located on the upper reaches of Morgnec Creek with water access to the Chester River. Bring your boat to explore all nature has to offer, commune with eagles, herons, terns, deer, turtles and other wildlife on this lovely creek. This home offers waterfront views from nearly every room, numerous upgrades over the past few years, perfect for a weekend get away or a fulltime resident. Just minutes from historic Chestertown and with the new Middletown by-pass less than 1 hour from Wilmington and points north.</span>

Price: $589,000

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Blessed with the most perfect setting on the upper Bay, this beautifully built home offers waterviews from three levels. Bonus to this southwest view are the passing ships and a deep water pier. Sun filled rooms, first floor master and family room in the lower level with a walk out access to a brick patio make for delightful accomodations. Only minutes into Elkton and I 95.<br />View Property Video Below:<br /><p>https://vimeo.com/339144079</p>

Price: $949,000

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One of a kind private oasis on Cabin John Creek. Dock with lift, 75' of new bulkhead, custom landscaping and outdoor kitchen to enjoy three seasons. Beautifully maintained with custom wood work and attention to detail with views of the water throughout house. Water view office with roof top balcony. This home is designed for indoor and outdoor entertainment with each bedroom offering private bath.

Price: $990,000

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Cozy 3 bdr waterfront home with all the natural, private surroundings the eastern shore has to offer. Very easy access to more than 300 feet of bulkheaded shoreline. 2 large detached garages to store all the waterfront toys you will need to take advantage of all Langford Creek has to provide, fishing, crabbing, year round hunting or whatever you waterfront dreams desire.<br />View Property Video Below:<br /><a href="https://vimeo.com/300826586">https://vimeo.com/300826586</a>

Price: $538,000

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Beautiful flood constructed contemporary with 3/4 bedrooms, 41/2 baths located on the Elk River. Screened porch, decks, and deck by the water to enjoy the great summer breezes while sheltered by mature trees. Dock with 2 boat lifts and 2 jet ski lifts. Large walkout basement. Only minutes to I 95 corrider.

Price: $775,000

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Your home is your castle, literally. Unique construction from 1900. Colorful history of this magnificent home. Main floor bedrooms and bath. River stone fireplace in great room. Grand master bedroom with view of the Elk river. Fabulous master bath. an additional bedroom and a bath complete the second floor. Bulkhead, pier and boat ramp. Exceptional landscaping, even a secret garden.<br />View Property Video Below:  <br /><a href="https://vimeo.com/339153917">https://vimeo.com/339153917</a>

Price: $925,000

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Spectacular views of the Chesapeake Bay from nearly every room along with four seasons of sunsets nearly every night are included in this well meticulously maintained home. Fabulous kitchen for entertaining and a Master Bedroom suite perfect for relaxing. All just minutes from historic Chestertown.

Price: $798,000

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Privately located in a natural wonderland and close to Chestertown!  Relax and savor the water views from your deck, living room kitchen, bedroom, or from the separate cozy guest cottage filled with character and charm.  Deer, eagles, waterfowl can been seen from many places on this 7 acre property. The main residence and guest cottage have been recently updated and are very well maintained.  A private pier, canoe and kayak rack at water's edge and acres of mature woods just add to the value.<br />Highlights of this property: separate guest home with vaulted ceilings and waterview deck, natural, wooded, private lot, deck overlooking the water, all new windows in both homes, private dock plus canoe and kayak rack<br />View Property Video Here <br /><a href="https://player.vimeo.com/video/192006295">https://player.vimeo.com/video/192006295</a>

Price: $675,000

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A spectacular waterfront location just outside of historic Chestertown providing privacy but not isolation, a blend of lawn and mature shade trees, over 200 feet of waterfrontage, private dock with a boat lift, beach, sunsets and is improved by a three bedroom home with a screened porch overlooking the water, hardwood floors, views of the river from almost every room and is situated to offer easy access from the house to the water's edge.<br />Click the Link below to View the Property Video<br /><a href="https://player.vimeo.com/video/226756065">https://player.vimeo.com/video/226756065</a>

Price: $645,000

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Experience the fantastic sunset from the riverside of this adorable cottage. Enter the foyer and capture the essence of Eastern Shore living. A country kitchen opens to the living and dining area. The sunroom is the place to be to watch all sorts of water craft from kayaks to mega yachts. Never a dull moment. Convene on the deck for refreshments or a superb crab feast. Detached guest quarters add to this special property. Call it home or call it a haven. Exceptional community spirit welcomes all.

Price: $749,900

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Waterfront home on Turners Creek with year round sunsets located in the private waterfront community of Kentmore Park. Five bedrooms and three full baths. Room to entertain friends and family.  Low maintenance brick exterior allows owners time to enjoy outdoor activities on the water or in the yard. Private pier for watercraft and crab traps. Relax on the deck and experience an awesome sunset along with very easy water access.

Price: $598,000

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This pristine contemporary is nestled on a partially wooded 3 plus acre lot with over 200’ of shoreline. Located in Fairgale, an upscale waterfront community just minutes from Chestertown, this property gives the feeling of a very special place. The home offers great space inside and out to entertain or to enjoy all the seasons of the year. Bristling with special features as beautiful wood throughout the house to exude warmth to a spacious deck to enjoy the wonderful setting. There is walk way to the water and a boat slip with lift at the community pier, which is only minutes to the Bay. Separate building to house all the toys for boating and other activity.<br /> View Property Video Below:<br /><a href="https://player.vimeo.com/video/194690009">https://player.vimeo.com/video/194690009</a>

Price: $795,000

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<b>Two slips and deeper water at the dock<span> </span></b><span>of this quality-built treasure on a very special parcel on Grays Inn Creek, perfect for a second home or retirement retreat. Situated to maximize the panoramic views. Pella windows, hardi-plank siding. Just a few minutes to downtown Rock Hall or historic Chestertown. Luxury master bath has radiant tile heating. Charming, and will steal your heart.</span>

Price: $449,900

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<p>Wonderful, private retreat with plenty of room inside and out for the whole family and situated on a beautiful Bayfront lot.  Unobstructed views of sunsets, rip rap shoreline with over 200' along the bay.</p>

Price: $ 620,000

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Endless views on 3 sides highlight this light filled home. A “must see” master bedroom with a wall of glass and balcony makes for unforgettable water vistas. Deep water, a bulkheaded shoreline, pristine lawn and landscaping add to the special quality of this offering.

Highlights of this Home:
Elevated deck with endless water views
Privacy at the end of the road
Located on a point of land with water on three sides
New deck overlooks the water
Lawn to the bulkheaded waterfront
Deep water dock potential
Rural, yet close to urban areas
Screened porch overlooks the water
Easy walk to the water

Price: $ 675,000

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A beautifully presented home on 5 plus acres of wooded waterfront, private yet not isolated, and close to Rock Hall and historic Chestertown. This superbly appointed home is a true labor of love. Consider: a foyer with an inlaid hardwood compass, a huge deck overlooking the water, a grand master suite that pampers you with size and luxury, an elegant, "state of the art" kitchen, two family rooms, a library, additional bedrooms with private baths, a 47' x 31' outbuilding, a splendid stone fireplace, and very much more, all in "like new" condition and set on 400' of waterfront protected by hand laid field stone.

Additional Highlights:

Australian Cypress flooring
Iron Wood decking
Black Locust mantle
Granite counter tops
Cedar cathedral ceiling in living room
Cherry cabinets at wet bar
Built-in sound system
Attached 2-car, oversized garage
70' dock with water and electric
10,000 lb. boatlift, 3' MLW
Conveniently located close to Rock Hall and Chestertown

Price: $ 998,000

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Spectacular secluded 4 bedroom Bayfront home overlooking the mouth of the four rivers making up the Chesapeake Bay.  A perfect place to relax and get away from all the hustle of life and watch ships and boats make passage through the upper bay.  Rip rapped shoreline with beach access for fishing and floating on a summer day.  Not far from the town of Betterton.

Price: $ 625,000

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Bring your sailboat!  Deep, protected water close to the Chesapeake Bay.  Light-filled rooms offer unforgettable water views.  Detached garage has apartment above.  Located in the much sought after community of Kentmore Park.  Beautifully landscaped with huge deck overlooking the water.

Price: $ 998,500

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Relax and take in panoramic sunsets from your private pier, lawn or porch.  Bayfront home with fireplace and views from kitchen, family room and living room.  Rip rapped shoreline and easy access to the water.

Price: $498,000

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Great Oak Landing- voted Best of the Bay- This waterfront property perches on the shores of the creek.  It has a commanding view of the water and has been lovingly cared for.  It offers large and comfortable rooms, roof top sunroom, and front and back outdoor living spaces.  Tastefully landscaped property providing space and privacy.  Wonderful primary home or delightful getaway.  Ownership includes the amenities of Great Oak Landing such as golf, tennis, restaurant, pool, and Kids Club.

Price: $ 736,000

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This home is an extraordinary testament to quality, attention to detail, comfort, and function. There are very few homes in the Perryville area that even come close to matching the level of abundant features and solid, sound construction on display here. If you want to take advantage of all that the Chesapeake can offer and enjoy it without compromise, this is the ideal location for you and your family.

Price: $ 980,000

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Elegant home fronting protected Swan Creek. Fabulous water views and 4+ MLW for your boat. Open, airy floor plan with fireplace. 1st floor master suite, deck, separate 3-car garage with storage space above.

Price: $ 749,000

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Cherish your own private beach and picnic area, savor the heavenly sunsets and water views and relax in this spacious home that is a true labor of love. In like new condition, this home occupies a most prominent site. Its huge decks and patio, along with almost every room, present commanding views.

Price: $998,000

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Enjoy sweeping panoramic water views and watch ships from around the world from this custom built four bedroom home that provides privacy, yet not isolation, a partly wooded location, a detached garage, a private pier with deep protected water and a boat house and is located close to Historic Chestertown.

Price: $845,000

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Lovely classic Eastern Shore cottage on Freeman Creek looking out to the Sassafras River. Rolling acreage. Original charming one room cottage is preserved on the property. Enjoy the sunroom in the warmer weather and the fireplace in cooler times. Easy stroll to the pier and water or try the stairs if you prefer. Short distance to the private Kentmore Park Community and Beach.

Price: $ 650,000

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Surrounded by mature trees and landscaping, this custom built home offers quality materials throughout, a large updated kitchen, spacious rooms, most of which over look the water, wood burning fireplaces, built in book shelves and window seats, a walk-out lower level, a deck, a lawn gently sloping to the water's edge, a dock and is located close to Historic Chestertown. One must tour this home to truly appreciate all that is has to offer.

Price: $875,000

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Just under two acres at Little Welsh Point. Expansive view of the Elk River from this one story home. Watch the activity on the water every day of the year. Cruise the river to the Bay or travel the Canal to Chesapeake City and points east.

Price: $649,000

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