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Eastern Shore Homes with Privacy

View listings for homes with privacy on the Eastern Shore of Maryland. You may also be interested in browsing homes with land.

Eastern Shore MD Homes for Sale with Privacy

Call Chuck Mangold at 410-924-8832 with any questions or to see any of these properties in person.

Easton MD 21601

Easton, MD

Price$5,075,000

Est. Mortgage: $/month

MLS Number MDTA137518

  • Single Family
  • LocationType River
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 6815

Located on the Tred Avon River this magnificent home offers incredible panoramic water views, the town of Oxford and glimpses of St. Michaels! The wide-open water views are stunning and can be enjoyed from almost every room of this nearly 7,000 square foot Waterfront Estate which experienced a major remodel in 2016/2017. This home is designed with an attention to detail and a focus on providing a lifestyle of simple and approachable elegance while offering opportunities for intimate moments in the perfectly curated spaces or entertaining on a grand scale. Nothing has been ignored in the creation of this spectacular home!The stunning home features a grand foyer with circular staircase leading to the second floor, with the main floor opening to the dramatic formal living room. The 30-foot cathedral ceilings, wall of glass overlooking the river and the massive natural stone fireplace all unite to offer a sensation of grandeur, reminiscent of historic country estates yet casually comfortable inviting you to be drawn in to sit, read, converse or relax.To the right of the foyer with its stunning and architectural hand painted Heart Pine Floors is the elegant and formal dining room which flows into the Great Room which is open to the kitchen and casual breakfast room. The Great Room is clearly the heart of this home. With its gas burning fireplace, light streaming in from the expanse of windows and the gorgeous water views it is the perfect backdrop for gatherings, game nights or causal meals. Beyond the breakfast room is the sunroom, with the two walls of windows and intimately arranged furniture, you develop a sense that this is the place for coffee and connecting.On the other wing of the main floor is the stunning master bedroom and the en-suite spa like bath. Serene, beautifully appointed and spacious, this personal space invites you to retreat, relax, or escape.Up the grand staircase and onto the second story foyer you have two bedrooms and a bath on one side, two more bedrooms (or an office), a second bath, and the media/game room on the other. All bedrooms and media room have access to either a private or a shared deck overlooking the manicured and expansive lawn with sweeping views out across the water; the vistas are incredible, the interiors sublime. The media room, while providing state of the art technology carries on the feeling of old world charm. Plaster walls with sixteen coats of plaster, hand painted by artisans brought in specifically to create this masterpiece, generate awe yet imbue the room with strength, solidness and warmth. Multiple closets, storage areas, ~secret~ spaces and a seamless integration of space and design continue the feeling of peace and tranquility which this home provides.Opposite the main home is a charming building housing a 3-car garage with a loft style guest space on the second floor. The loft can easily be finished as an au pair suite, guest house or caretaker~s cottage! While its unique location on the Tred Avon provides total privacy, the proximity to dining and entertainment in Easton, St. Michaels or Oxford is just minutes away by car or yacht which could be docked at your private 240-foot dock with water, electric, two boat lifts and a 4 foot MLWD. While you may never want to leave this esate, the Easton Newman County airport is just ten miles away and the Nation~s Capitol, Baltimore, Philadelphia or New York City are all commutable and easy travel options. By yacht, car or plane the options to arrive are limitless. The breathtaking beauty of nature that resonates with both peace and splendor is extraordinary to experience~come and feel what this home offers.

Listed by Joseph A Petrone of Monument Sotheby's International Realty

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$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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6201 Swan Creek Rd Rock Hall MD 21661

Rock Hall, MD6201 Swan Creek Rd

Price$4,490,000

Est. Mortgage: $/month

MLS Number 1000487872

  • Single Family
  • LocationType Bayside
  • Address 6201 Swan Creek Rd
  • Bathroom 8
  • Bedrooms 8

Live your dream and enjoy an elegant and serene waterfront estate nestled on 177+ acres of a private and secluded peninsula along Maryland's Eastern Shore. Delight in the commanding and expansive views of the surrounding farmland and the picturesque Chesapeake Bay. The views are rivaled only by the impressive and completely renovated 5,500+ square foot classic 19th-century farmhouse. This majestic property features beautiful 100-year-old reclaimed heart pine flooring, an open floor plan with an abundance of natural light, four master suites, two additional guest bedrooms, a powder room, and a home office with custom bookshelves. Enjoy many options for casual or formal entertaining inside the house, outside on the sprawling lawn or around the relaxing pool and hot tub. You or your guests can also retreat to the one bedroom cottage situated along the shoreline. Its oversized windows provide captivating panoramic views of the bay. No matter what you feel like doing, there is something for everyone. You might take a refreshing dip in the pool, barbecue with guests on the large side deck, play a few rounds of tennis on the fenced-in hardtop court, enjoy the sunset from a rocking chair on the front porch or stargaze from the widow's walk. The estate is also the ultimate retreat for outdoor sportsmen & enthusiasts. Boaters will appreciate the private pier tucked in a protective cove on Tavern Creek. It is the perfect place to fish and crab for the evening's meal. You may also launch boats from the property's boat lift, floating dock or cement boat ramp. Grab your kayak from the boathouse and spend the day watching ospreys and blue herons while exploring the bay and the surrounding waterways. With its ideal location, you are just minutes away from some of the Chesapeake Bay's finest marinas and authentic waterside restaurants. Private and remote while being close to major Mid-Atlantic metropolitan areas, this Eastern Shore jewel is sure to give you and your family a lifetime of memories. The Main House: This 1870s farmhouse had a complete renovation from the foundation up along with a major addition in 1998. 5,500+ sq. ft. - 6 bedrooms/5.5 bath home. 3 full levels w/ partly finished basement. 3 woodburning fireplaces / 2 propane. Widow's walk / sundeck with 360 degree views. Large, covered front porch. Designed for both formal entertaining and causal living. Reclaimed heart pine flooring throughout. Original staircase and mouldings. The Cottage on the water's edge: 1 bed/1 bath with expansive waterviews. Situated along the Chesapeake Bay and protected Tavern Creek. Large, waterside deck. Waterside patio. Wood flooring throughout. Open floorplan designed for every room to have a view of the water. The Accessory Structures: Garage with 1 bed/1 bath above, attached fenced in dog pen. Converted dairy barn with two levels of storage. Storage shed for fuel & decoys. Dry boat house with a cement ramp for ease of launching small boats and running water. Pier with electric boatlift, floating dock, power and running water located on Tavern Creek with easy access to the Chesapeake Bay. Heated inground pool with built-in hot tub. Tennis court - fenced-in hardtop. The Grounds & Property Features: Ultimate privacy on 177+ acre waterfront peninsula. Gated entrance providing additional privacy. Two waterfowl ponds & 3 duck blinds. More than 1.5 miles of waterfront shoreline. All 4 contiguous lots are waterfront and each have separate tax ID's. Lot 2 / 36.74 acres - Lot 3 / 22.28 acres - Lot 4 / 78.18 acres - Lot 5 - / 40.63 acres- Agricultural conservation easements are available for review by request.

Listed by Brent J Allen of Long & Foster Real Estate, Inc.

$
$
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$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5780 Shipyard Point Rd Royal Oak MD 21662

Royal Oak, MD5780 Shipyard Point Rd

Price$3,999,999

Est. Mortgage: $/month

MLS Number MDTA135338

  • Single Family
  • LocationType Bayfront
  • Bathroom 8
  • Bedrooms 5
  • Square Feet 9740

The gorgeous, private 9740+ square feet colonial nested on 22+ acre waterfront estate offering 6+ feet of water on Haskins Cove/Irish Creek. The 4100'+/- of shoreline allows water view from most all rooms. The main house offers 4 bedroom suites plus large, maids quarters which has its own entrance over one of the garages. You will enjoy the large great room with two fireplaces and the library with 9 foot+ ceilings is you own little getaway. The kitchen offers top of the line appliances with huge granite island, (new refrigerator 2018 sub-zero). Casual entertaining in the media room. Formal dining room offers elegant in style. Two attached garages. The 3 bedroom, 2 bath waterfront guest house allows privacy for your guest, they can enjoy your waterfront. Two extra-large barns with offices & wash stations, fully fenced for your horses. Get your exercise on the fully fenced Tennis Courts, then a swim in the diving pool and enjoy your special refreshing drink at the pool house. If you are still ready for more fun, power up you boat at the dock, which has 6+/- feet water depth at MLW, and sail the waters of Irish Creek and Haskins cove. For the nature lovers, you have your pond with all types of wild life. This estate meets most all lifestyles giving you privacy and seclusion yet only 10 minutes to Easton or ST Michael that offers the arts, shopping, and restaurants of all flavors. This home is considered be one of the finest estates in Talbot County, due to the waterfront and location The exterior is brick with sprawling lawn and mature plantings. The interior offers chair railing, crown molding and lovely stairway when entering the large open foyer. The kitchen offers a view of the waterfront (as do all rooms) the current owner has owned the property since 1993.Currently some updating in process.

Listed by Glory Bee B Costa of Keller Williams Select Realtors

$
$
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$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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6010 Shipyard Ln Easton MD 21601

Easton, MD6010 Shipyard Ln

Price$3,500,000

Est. Mortgage: $/month

Pending

MLS Number 1003265471

  • Single Family
  • LocationType River
  • Address 6010 Shipyard Ln
  • Bathroom 7
  • Bedrooms 6

"Ship's Point" Private point overlooking the Tred Avon and Trippe Creek. 13+ acres, 2,300+/- ft of waterfrontage, bulkheaded shoreline, deep water dock with 4 slips, custom pool/spa, brick/stone patios. Main house features 3 fireplaces, 6 bedrooms, 6.5 baths, formal living & dining, sitting & family rooms, large kitchen, maids quarters. Also includes a detached garage and huge guest house! Water on three sides. Protected views. Complete privacy. Broad waterviews. Breathtaking Sunrises/Sunsets and Southerly Breezes.

Listed by Clifford E Meredith of Meredith Fine Properties

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$
%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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26108 Bachelors Harbor Dr Oxford MD 21654

Oxford, MD26108 Bachelors Harbor Dr

Price$3,495,000

Est. Mortgage: $/month

MLS Number 1001491018

  • Single Family
  • LocationType River
  • Bathroom 6
  • Bedrooms 4
  • Square Feet 5251

Practically an island located where Choptank and Tred Avon Rivers enter Chesapeake Bay. Big 180 degree water views with 660 ft. of riverfront and tidal sandy beach. Great terraces, rolling lawn, private dock, and above rip-rap sandy beach with firepit for entertaining and enjoying gorgeous year-round sunsets and summer sail races. Big sky and adjacent open land maximize space and privacy. PRICED BELOW ASSESSED VALUE!!

Listed by Clifford E Meredith of Meredith Fine Properties

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$
%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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4746 Cliffs City Rd Chestertown MD 21620

Chestertown, MD4746 Cliffs City Rd

Price$3,400,000

Est. Mortgage: $/month

MLS Number 1000084191

  • Single Family
  • LocationType River
  • Address 4746 Cliffs City Rd
  • Bathroom 5
  • Bedrooms 5

An elegant new offering located on the Chester River in Quaker Neck, just south of Historic Chestertown. This magnificent family residence has it all: ideal waterfront & wildlife habitat, a private pier w/ 3ft MLW, marvelous panoramic southern water views, a blend of open & wooded land, privacy, extensive gardens and is located in the premier estate area of Kent County.

Listed by Christopher D McClary of Gunther-McClary Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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27188 Baileys Neck Rd Easton MD 21601

Easton, MD27188 Baileys Neck Rd

Price$2,950,000

Est. Mortgage: $/month

Pending

MLS Number MDTA137604

  • Single Family
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 7907
  • Year Built 1920

An exceptional address with a seamless blend of privacy and outstanding amenities on 9+ acres. The tree-lined lane brings you to the impressive brick main house where the entrance hall provides instant views of the Tred Avon River and Trippe's Creek. Gracious living room, incredible formal dining room with service area, stately paneled library/study, large family room with fireplace, beautifully appointed kitchen, butler's pantry, large laundry room, first-floor master suite with lounge area and office, large master bath, two walk-in closets. Second floor: reached by grand circular staircase has three bedrooms all with waterfront balconies, large bathrooms and enormous storage rooms. Second House/ Guesthouse is a separate residence with full kitchen, living room, dining area, first-floor bedroom, full bath, laundry room. The second floor has 2/ 3 bedrooms, Balconies, full bath. There is a complete Exercise Room as well as professional-grade Sauna. Exterior: Large Swimming Pool, Gazebo with refrigerator sink granite countertop and large outdoor Flat Screen TV, first-rate Tennis Court with backboard and basketball. Enclosed Outdoor Shower with Bath, Sports Equipment room, brick surround Hot Tub, raised Garden Beds, Mature Trees. Dock with 3 Boat Lifts, Water, Electricity, and floating dock. Secure rip wrapped shoreline. Click on Property Tour. By Appointment Only.

Listed by Chata R Smith of Coldwell Banker Chesapeake Real Estate Company

$
$
%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3015 Bennett Point Rd Queenstown MD 21658

Queenstown, MD3015 Bennett Point Rd

Price$2,875,000

Est. Mortgage: $/month

MLS Number MDQA142142

  • Single Family
  • LocationType River
  • Bathroom 8
  • Bedrooms 4
  • Square Feet 6140

Tranquility, privacy and luxury living abound at this stunning home situated beautifully on the Wye River. With deep water slips and a 200-ft custom-built pier, this home redefines waterfront living and offers endless possibilities for convenient boating and outdoor activities at your leisure. A grand entry framed with meticulously landscaped grounds and a circular drive sets the stage for the elegance that lies inside this magnificent 6,000+ square foot estate nestled perfectly on 6 acres. Soaring ceilings greet you in the foyer and offer water views, enticing exploration into the library, sitting room and wet bar with custom built-ins and a fireplace. Gorgeous American Cherry floors on the main level add a warmth and uniqueness to the home, complimented by the beamed ceiling and stone fireplace that make the large open living room the ideal place for taking in the breathtaking views of the river. A gourmet kitchen and breakfast area provide the perfect setting for starting your day and continue the theme of enjoying the water from every room in this residence. They also offer wonderful entertaining possibilities with open and easy access, a grand island, and luxury finishes. The main-level master suite amazes, from the custom dressing room to the spa-like bath, all complete with unobstructed water views. His and her water closets add a level of convenient luxury that is indicative of this thoughtfully designed masterpiece. On the upper-level, bedroom suites provide attached baths, sitting rooms and walk-in closets for convenience; each with water views to ensure the one-of-a-kind setting is enjoyed throughout every room of the estate. An attached garage includes parking for 3 cars, while a detached garage provides additional space for 4 cars and includes a luxurious guest apartment for hosting. From the grounds to the interior finishes, no stone was left unturned on this magical waterfront property.

Listed by Jimmy J White Jr. and Mary E Casson of Long & Foster Real Estate, Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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7116 Pea Neck Rd Saint Michaels MD 21663

Saint Michaels, MD7116 Pea Neck Rd

Price$2,590,000

Est. Mortgage: $/month

MLS Number MDTA137296

  • Single Family
  • LocationType Bayfront
  • Address 7116 Pea Neck Rd
  • Bathroom 3
  • Bedrooms 3

Privacy and nature abound in this beautifully expanded 3 bedroom home with additional 1 bedroom guest apartment over the detached garage. 20 acre property includes farm, orchard, gardens and beautiful landscaping. Agreement with local farmer provides nominal income and keeps taxes low as a farm. Major renovation and expansion in 2006 include expanding main house with new 1st floor master bedroom and bath, new dining room, sun room, three fireplaces, decks, finished 3rd floor with balconies, new pool, new dock, new detached garage with workshop and 1 bedroom guest apartment above. Enjoy breathtaking sunsets every night with expansive views of Edge Creek. This is truly a nature lover~s paradise less than 4 miles from the shops and restaurants of St Michaels. It must be seen to be appreciated.

Listed by Laurence F Brennan of Benson & Mangold LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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12938 Sunset Ave Ocean City MD 21842

Ocean City, MD12938 Sunset Ave

Price$2,150,000

Est. Mortgage: $/month

MLS Number MDWO112062

  • Single Family
  • LocationType Bayfront
  • Address 12938 Sunset Ave
  • Bathroom 6
  • Bedrooms 6

Rare Opportunity to Own one of the Finest Southern Bay and Ocean Views Homes available in West Ocean City. This Spectacular 6 Bedroom, 6300 Square Foot Coastal Waterfront Masterpiece is Situated on a Deep Water Bulkhead within eyesight of the Atlantic Ocean and Inlet and Will Accommodate Deepwater Dockage for up to an 80' Sport Fishing Yacht. Grand Open Vistas of the Bay, Ocean and Assategue are Truly Stunning and Available from All 3 Levels of this Magnificent Coastal Home. This Wonderful Home Boosts a 4 Car Garage and an Elevator to Service All 3 Levels. The Second Floor is the Main Living Area Offering Commanding Waterfront Views of the Bay, Ocean, Assateague and Commercial Harbor, The Spacious Kitchen has New Stainless Steel Appliances, Butlers Pantry, Abundant Cabinets, Granite Counter Tops, Island and Eat-in Area facing the Open Bay and is a Great Gathering area that Leads out to the Southern Exposed Waterfront Decks, There is also a Formal Dinning Room, Great Room with Vaulted Ceilings, Billiard & Game Room and Super Bay Front Master Suite & Bath as well. Third Floor has another Master Suite With Southern Coastal Views from the rear Large Deck. Additionally, there are 2 more Bedrooms on the 3rd Floor that are serviced by a Jack & Jill Bath. This First Floor has 2 More Bedrooms, a second Kitchen and Living Area and access to Multiple Garages and Rear Covered Waterfront Patio, This Waterfront Home has many unique Features including 2 Huge Laundry Rooms on separate levels, Plenty of Storage Closets, Workshop, 3 Natural Gas Furnaces and One Heat Pump, Gated Driveway for the Ultimate Privacy & Security, There is also a Sound Speaker System throughout Home, Fencing on 3 Sides of the Property with Mature Landscaping and Situated on a Double Lot offering 100 Feet on the Water. A New Vinyl Bulkhead to be installed in March 2020 and New Ground level Vinyl Deck Also to be installed, This Property is Directly Located Across from Sunset Marina the Play Ground for the World Sports Fishing Anglers! The Large Covered Patio is an Amazing Place to Hangout, Watch the Boats Go By, Entertain and View the Sunsets. This One of Kind Property has to be Seen to be Truly Appreciated. Come Down to the Land of Pleasant Living and Enjoy Coastal Living at its Finest.

Listed by Anthony E Balcerzak Jr. of Berkshire Hathaway HomeService PenFed Realty - WOC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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27465 Southside Island Creek Rd Trappe MD 21673

MLS Number 1003265427

  • Single Family
  • LocationType River
  • Bathroom 9
  • Bedrooms 10
  • Square Feet 7898

Beauvoir is an historically significant waterfront estate beautifully situated on 6+ acres on the north bank of La Trappe Creek with 1,489+/- of shoreline. Classic long tree-lined driveway, stunning broad water views and southern exposure. Elegantly casual period home with 2 wings and a separate guest house, ensuring entertaining space or privacy for all. The ultimate in Eastern Shore living!

Listed by Chuck Mangold of Benson & Mangold, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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27575 Wakefield Ln Easton MD 21601

Easton, MD27575 Wakefield Ln

Price$1,995,000

Est. Mortgage: $/month

Pending

MLS Number MDTA135042

  • Single Family
  • LocationType River
  • Address 27575 Wakefield Ln
  • Bathroom 5
  • Bedrooms 4

This custom crafted traditional home on 5.84+ acres boasts a gourmet kitchen and expansive family room with fireplace, as well as a winterized glassed-in porch. From the foyer entrance you will view a spacious dining room and living room with fireplace all with the finest of luxurious finishes. A magnificent custom-built study that follows offers a wet bar, icemaker, fireplace and custom cabinetry. The main level also offers an ensuite master bedroom, two half baths, a laundry/utility area with pantry and separate propane furnace room. The second level encompasses an enormous master suite with a walkout porch and fireplace accented by a large bath and generous closeting and storage, as well as two additional sizeable bedrooms with bath. A separate guest apartment consists of 1 bedroom with bath, family room, full kitchen and is found over the 4-bay garage with workshop. Heated pool, propane BBQ and many outdoor areas for waterfront entertaining, automatic 22 kW generator, rip rapped shoreline, Bailey-dock with 8,000 lb. boat lift and 4 ft. mlw. This tranquil Dixon Creek waterfront retreat is within minutes of Easton and St. Michaels and the property offers outstanding sights and sounds of nature along with supreme privacy with open waterfront views from every room.

Listed by Faye D Roser of Benson & Mangold, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.18% last updated on Jun 4, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Copyright 2020 BRIGHT, All Rights Reserved.  Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Chuck Mangold participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Data last updated June 5, 2020. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.

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