Property Listings - Waterfront Homes

Private 3.65 acre waterfront home with architectural design for plenty of light with immense potential waiting for you input. Detached 2 car garage with 2nd floor game room plenty of space for all your water toys. Partially finished basement and plenty of storage room.

Price: $798,000

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Spectacular Bayfront with clear, uncompromising views. Hard to find one-floor-design, and completely out of the flood zone. Wake up to the sparkling bay views every day in the beautiful primary bedroom. Views from all rooms. There is a family room with a rustic lodge feel, incorporating the charm of the original cottage, and spacious decking surrounding the house. The perfect place for coffee, a cocktail, catching bay breezes and watching the sunset. Only minutes into downtown Rock Hall with it's charming Main Street, coffee shop, jazz and blues venue, restaurants, and many marinas. Just under two hours to Philadelphia, Baltimore, DC, Wilmington and South Jersey. Make an appointment soon to see this one.

Price: $1,300,000

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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: $800,000

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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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Like new waterfront 3/4 bedroom home located on the Elk River with water views from nearly every room. Sandy Beach, perfect location for all the desired water activities including relaxing and watch the ships pass by heading to and from the C & D Canal. Very easy access to points north and less than 35 miles from Wilmington DE and 60 miles from downtown Philadelphia

Price: $1,285,000

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What a sensational view of the Bohemia River and across to the historical brick house and vineyard from this renovated ranch home. There are newly updated bath & kitchen, new UV windows installed on sun porch, 3 yr old roof, leased solar panels. Newly painted outdoor patio, new garage door to be installed. So come and enjoy the great boating, your own 135 ' dock with 10K lb boat lift. The waterfront is owned by the community for access along the water. For the amenities in this community, the real estate taxes are lower than other communities. Located near the point, the community comes together to watch either the sail boat races or beautiful sunsets, also wake up with the sunrise over the river. The community swimming beach is just a short ride on a golf cart. With private roads, no through traffic.

Price: $799,000

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This fabulous craftsman style 3 bedroom home, is perfectly situated to enjoy the beauty and tranquility of the East fork of Langford Creek/Bay with approximately 150' of shoreline and sandy beach. The subject property is one of 5 waterfront properties that belong in the Cacaway Farm Cooperative Housing Corporation, an exclusive farm housing community. Experience the same benefits of a fee simple ownership but share the cost of expenses. Enjoy privacy and the use of your own waterfront with sandy beach by way of a gentle slope to the water, launching kayaks or canoes while deep water slip at the community dock is also included. It is improved by 2 car heated garage plus a smaller area for storage with a bonus area above. New BAT septic was installed in last two years, with the county becoming the operator of the new sewage treatment area. Please do not drive down Cacaway Farm Lane without an appointment. This is a private lane. Check out the Property Video Below: [embed]http://vimeo.com/440002581[/embed]

Price: $1,295,000

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Beautiful 4 Bedrooom home on the the Sassasfras River with plenty of space to spread out. Broad southern exposure views, deep water, 7ft mlw on the dock, Sandy Beach, boat ride to restaurants less than 10 minutes away, Chesapeake Bay less than 4 miles Very easy access to points north and south, completely renovated and meticulously maintained home. Need anything else? Just 69 miles from Center City Philadelphia and 88 miles from Washington, DC.

Price: $1,425,000

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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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Spectacular farm overlooking the entrance of Lankford Bay into Davis Creek. A sportsman's dream and a wonderful family compound. This modern colonial farmhouse takes in the views from just about every room. The kitchen and dining area is oriented for waterfront entertaining, and flows onto the enclosed Florida room as well as the large, spacious decks facing the Lankford. There is also a large traditional, formal dining area for cozy winter celebrations. Everything you need is on one floor, including first-floor mini master-suite, perfect for an in-law suite. The second floor is comprised of the larger master bedroom and 3 guest rooms and baths upstairs, along with an office/study. A total of five bedrooms and baths. All floors finished beautifully with wood flooring or ceramic tile. There is a dock that can accommodate a large party of boats, and the water depth is an impressive 5+ mlw. The parcel with the residence is 72.605 acres; it is flanked by two buildable separate parcels, one at 57.971 acres and the other at 82.311 acres. They are tilled and also used for hunting. The house has county sewer; the two parcels both have public sewer allotments. One of them also has a dock already installed, and a cleared buildable area with water views. No septic to worry about. The main property also has the addition of barns and farm buildings. There is a fantastic studio space on top of the main barn - so many possibilities for this space. Save plenty of time for a tour.
Check Out the Property Video Below:
https://vimeo.com/436150989

Price: $3,875,000

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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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Please call 410-275-2118 to speak with a representative about this property or fill out the form on the contact page.