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Eastern Shore Luxury Homes for Sale

View all luxury homes for sale on the Eastern Shore of Maryland. These properties are priced at $1M and higher. You'll find a variety of beautiful high end homes on the Eastern Shore.

Maryland Luxury Real Estate Listings

If you have any questions or would like to schedule a private viewing, contact Chuck Mangold. Get ready to find your dream home in Maryland! 

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27189 Island Creek Rd Trappe MD 21673

Trappe, MD27189 Island Creek Rd

Price$19,950,000

Est. Mortgage: $/month

MLS Number MDTA2003356

  • Single Family
  • Subdivision None Available
  • Bathroom 8
  • Bedrooms 4
  • Year Built 2009

Cecilia's Point - First-time offered...Spectacular...Nothing like it! 4 BR/4 BA/4 HB main house, 5BR/5BA guest house, detached garage with 2 BR/2 BA guest apartment, exquisite finishes and craftsmanship throughout, elevator, heated, saltwater pool, spa, cabana with bath, pickle ball courts, fairway with putting green, bocce ball court, broad westerly views of Choptank River, sandy beach, riprapped shoreline, deep water dock, 2 boatlifts, 4 jet ski lifts, tidal pond, kayak launch, fire pit, built-in grills with direct propane, hardwired internet, raised bed gardens, fountains, balconies, porches, paved driveway, brick and slate walkways and parking pad, mature trees, garage space for 10 cars, 2-bay pole barn. Conveniently located near country club, Downtown Easton, shops, restaurants, healthcare, and jet airport.

Listed by Clifford E Meredith of Meredith Fine Properties

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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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7751 Rollyston Dr Saint Michaels MD 21663

Saint Michaels, MD7751 Rollyston Dr

Price$15,000,000

Est. Mortgage: $/month

MLS Number MDTA2002950

  • Single Family
  • Address 7751 Rollyston Dr
  • Subdivision None Available
  • Bathroom 13
  • Bedrooms 9

2 parcels totaling 91 acres on the Miles River. 4-level, main house with elevator, full basement, 9 bedrooms, 9 full baths, 4 half baths, media room, main level bedroom. 4-car garage with rec room, bedroom, full bath and half bath. Heated, waterside pool, pool house with 2 full baths/changing area, covered outdoor kitchen. Pond with fountains, dock, 2 gazebos. Partially riprapped shoreline, sandy beach, dock with water and electric. Guest house with 3 bedrooms, 3 full baths, 1 half bath, barn. Property is priced at $15,000,000 unfurnished. Some furnishings could be included at a price to be determined prior to closing. Or, property can be bought furnished for $16,000,000 with the exception of artwork, personal items, and certain pieces of furniture, etc. that will not convey. Such items will be disclosed to the Buyer within 10 days of a satisfactory contract.

Listed by Clifford E Meredith of Meredith Fine Properties

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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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9750 Marthas Landing Rd Ocean City MD 21842

Ocean City, MD9750 Marthas Landing Rd

Price$12,900,000

Est. Mortgage: $/month

MLS Number MDWO115444

  • Single Family
  • LocationType Bayfront
  • Subdivision Martha's Landing
  • Bathroom 9
  • Bedrooms 6

Welcome to the White Marlin Manor Estate. This property exceeds expectations!! This is one of the most stunning properties you will find on the East Coast. The location is unique with both Bay and Oceanfront access. This amazing custom build Southern Living Style Coastal home, features: 6 bedrooms, 7 Full Baths, 2 Half Baths, 2 Gas Fireplaces, 12 seat luxury theater, custom cabinetry, Wine Cellar, Granite Countertops, Tray Ceilings in every bedroom, Custom Tile Showers in each bathroom, Etched Glass Elevator with custom painted underwater scene, Designer Lighting, California Closets, Rod Iron Railings, Gourmet Kitchen with heated tile floor, 7 Sub Zeros, Commercial Ice Machine, Teak flooring throughout, 12,000 lb boat lift,7 Ft. MLW at Dock, so many ornate details reminiscent of the Eastern Shore of Maryland. This property is a Fisherman's paradise. All Buyers must be qualified with all documentation presented to listing agent prior to any showings.

Listed by Jana Meredith of Meredith Fine Properties

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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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24629 Beverly Rd Saint Michaels MD 21663

Saint Michaels, MD24629 Beverly Rd

Price$12,750,000

Est. Mortgage: $/month

MLS Number MDTA2002924

  • Single Family
  • Subdivision Saint Michaels
  • Address 24629 Beverly Rd
  • Bedrooms 5
  • Bathroom 7

Travel down a mature, holly tree-lined drive and One Beverly reveals itself with understated Eastern Shore elegance. Situated on the 9 acre original farmstead of the 1867 Beverly Manor, this Georgian home provides a southwestern view overlooking San Domingo and Broad Creeks. The 5-bedroom main house, first occupied in 2003, is a traditional Georgian design meticulously built according to exacting standards to include handmade brick applications, historical window selections, exotic hardwood flooring, limestone fireplaces, custom architectural elements, and an elevator. Craft woodworking is displayed throughout the home's spiral staircase, large kitchen, pantry, and morning room, bathrooms, powder rooms, library, sunset room, fireplace mantles, snooker room, mudroom, map room, ceiling and baseboard trims, and exterior cornices. The central River Room 19ft ceiling provides expansive views of the creek waters and overlooks the terrace which is accessible through triple hung windows. The kitchen and pantry are outfitted with high-end Viking, Miele and Sub-Zero appliances. The large mudroom includes a laundry station, shower, sauna, powder room, refrigerator drawers, a custom farm sink, and an abundance of storage. This homesite includes a guest cottage nestled close to the water, the original carriage house now converted into an office with direct high-speed broadband service, a large pool, an outdoor Viking grill, a Morton barn, a freshwater pond, a greenhouse, and raised brick cutting garden. Established landscaping and majestic trees provide a lush environment to enjoy your Eastern Shore lifestyle.

Listed by Clifford E Meredith of Meredith Fine Properties

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$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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2924 Ocean Gtwy Trappe MD 21673

Trappe, MD2924 Ocean Gtwy

Price$10,950,000

Est. Mortgage: $/month

MLS Number MDTA2002774

  • Single Family
  • Subdivision None Available
  • Address 2924 Ocean Gtwy
  • Bedrooms 7
  • Square Feet 9833

658 +/- Acres of waterfront farmland in Talbot County, "Middleville" circa 1880 Tidewater Colonial, provides a mature charm and country living on the Eastern Shore. The main house has been kept as a comfortable country residence with subtle charm and recent improvements and upgrades. Enormous effort has been directed toward wildlife habitat improvement with an emphasis on waterfowl. Guest accommodations, a caretaker's house, housekeeper's house, numerous storage and outbuildings, eight waterfowl impoundments, a pier, shoreline revetment, and a living shoreline provide for a 'turn-key' farm on Maryland's Eastern Shore. The listing includes five parcels.

Listed by Schuyler G Benson and Coard A Benson of Benson & Mangold,LLC

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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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28343 Mallard Dr Easton MD 21601

Easton, MD28343 Mallard Dr

Price$7,300,000

Est. Mortgage: $/month

MLS Number MDTA139536

  • Single Family
  • LocationType River
  • Address 28343 Mallard Dr
  • Subdivision None Available
  • Bathroom 13

Mallard Drive is an extraordinary waterfront estate between Easton and Oxford on Peachblossom Creek. This breathtaking property provides a commanding presence with southern exposure, high elevation, mature trees, and a private setting. Built in 2004, the residence and improvements bespeak quality, and it shows with attention to detail in every facet. From the manicured grounds to the immaculate systems and infrastructure of the residence, this offering is sure to please the most discerning buyer. The property boasts a stately gated entry setting the pace upon arrival with manicured grounds and a gravel drive leading to a stone bridge. The driveway winds, meandering through a canopy of mature hardwoods and pine. Custom hardscape features throughout the property. A grand entry in the two-story foyer and gallery sets the tone upon entering this magnificent home. The trim work, joinery, and finishes are immaculate, and spaces within the residence are proportionally balanced, creating a comfortable and inviting atmosphere. The transverse hall leads to the main living areas with spectacular water views and natural light. To the east, the formal dining room leads to the spacious gourmet kitchen and casual dining. The conservatory provides a delightful and casual living space, augmented by an indoor natural stone koi pond. Here, residents benefit from convenient access to the elevator and the oversized three-car garage for daily entry. Heading west down the traverse hall leads to a screened-in porch with brick flooring and opens to a gorgeous patio under a pergola. The first-floor primary bedroom suite features a waterfront seating area, a luxurious bath with a clawfoot tub, a dressing room, and two spacious custom-built walk-in closets. An elegant office with stained glass doors opens to the library above and is connected by a winding staircase. The second floor features a unique library connecting to the second-floor study, two exquisite waterfront guest suites, one inland guest suite, an additional laundry room, an elevator, and third-floor access. The third floor offers a recreation and billiards room with a wet bar, a king guest suite, and a twin guest suite. The 6,000' basement is easily accessible by elevator and stairwells. In addition to two storage rooms, the basement includes an exercise room, wine cellar, and ample storage. The Au Pair Suite is located above the garage of the primary residence with a separate entrance and offers fantastic waterfront views. This apartment is completely separate and offers a generous living space with a full bath, a living room, dining room, and kitchen. The Caretaker's Cottage is a short remove from the main residence. It also has a full basement, two bedrooms upstairs, an open kitchen, living and dining room. A two-car detached garage is adjacent to the cottage. The shoreline in front of the house is secured with a timber bulkhead along Peachblossom Creek. The pier in front of the house is 100' long with 5' of water at mean low tide controlling depth. 7' of water at the dock. There is an 8,000 lb boat lift, a personal watercraft lift and float along with a concrete ramp. The additional pier is found in the basin, yielding 5' at mean low tide with another boat lift and multiple personal watercraft lifts. Both piers have 50 amp service, lighting, and water. Proximity to Easton - 6 miles, Oxford- 7.5 miles, Philadelphia - 116 miles, and Washington D.C. - 75 miles puts this offering in a very desirable location enjoying a rural, small-town setting with a vibrant arts community, competitive medical services, and everything appreciated by those familiar with the Eastern Shore of Maryland.

Listed by Coard A Benson of Benson & Mangold,LLC

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$
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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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32180 Wilson Point Rd Galena MD 21635

Galena, MD32180 Wilson Point Rd

Price$6,900,000

Est. Mortgage: $/month

MLS Number MDKE2001420

  • Single Family
  • LocationType River
  • Subdivision Sassafras Cove
  • Bathroom 9
  • Bedrooms 6

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. Find your favorite resting spot on the dock, the Manor house the Cottage, Pool house, Guest house or in the Barn tavern. 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.

Listed by John J Burke of Gunther-McClary Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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4190 Evergreen Rd Oxford MD 21654

Oxford, MD4190 Evergreen Rd

Price$5,495,000

Est. Mortgage: $/month

MLS Number MDTA2003456

  • Single Family
  • Address 4190 Evergreen Rd
  • Subdivision Oxford Road
  • Bathroom 5
  • Square Feet 3696

Welcome to "Evergreen", truly one of the most beautiful waterfront farms in Talbot County. Sited on 121 acres in Oxford Md, this property has over 2000' of shoreline (most rip-rapped) bordering the Choptank River and Island Creek, and a large tidal pond which offers incredible views and is an extraordinary habitat for wildlife. Spectacular sunrises and sunsets can be seen from this property, which is one of the few remaining large parcels offering complete privacy yet just minutes to Oxford. The meandering lane leads through the fields and up to the gorgeous point with panoramic vistas. The 6BR/5BA house was built in 1962, remodeled in the mid 1980's, and boasts amazing water views from nearly every room. In addition, there are 2 living areas and wonderful 1st and 2nd floor waterside screened-in porches. Adjacent is the large gunite pool and the protected pier is located in the cove and offers 3.5'MLW. Preliminary work from Lane Engineering indicates potential development rights, and soil testing in 2019 showed acceptable percs though no further site work has been completed. 80 acres are currently being farmed (and have been for decades) and hunting rights have been given to the same hunters for many years. No formal written leases are in place. The house is currently being rented on a short-term basis for a few weeks this summer so please contact the listing agent for showing dates, more information and also property exclusions. The pier and barns are being sold in as-is condition. A right-of-way is in place for the property located at #4184 Evergreen. This is a very unique and rare opportunity to own an outstanding property on the Eastern Shore!

Listed by Laura H Carney of TTR Sotheby's International Realty

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$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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435 Cinnamon Teal Dr Centreville MD 21617

Centreville, MD435 Cinnamon Teal Dr

Price$5,250,000

Est. Mortgage: $/month

Pending

MLS Number MDQA2002662

  • Single Family
  • LocationType River
  • Address 435 Cinnamon Teal Dr
  • Square Feet 8953
  • Bedrooms 5

Situated on over 50 beautiful acres overlooking the mouth of the Corsica River, 435 Cinnamon Teal Drive in Centreville, Maryland is an exquisite custom home. No expense was spared during the design and construction of this nearly 5,700 sqft home with an additional 3,700 sqft of finished living space on the lower level. The home features fine trim and finish work throughout, amazing views of the Corsica and Chester Rivers, a studio apartment above the detached garage, and one of the finest 2-story barns in the area. Located just 30 miles from Annapolis, the property sits on what was once the 1,600-acre summer estate of John Jakob Raskob, builder of the Empire State Building, in the early 1900s. Raskob's estate homes, located on what is known as Pioneer Point, were most recently owned and used by the Russian Federation as an Embassy retreat until they were kicked out by the US Government in 2016. *Listing includes an additional 25.43ac lot.

Listed by Travis O Gray of Engel & Volkers Annapolis

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$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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10205 Kintore Easton MD 21601

Easton, MD10205 Kintore

Price$4,995,000

Est. Mortgage: $/month

MLS Number MDTA2000049

  • Single Family
  • Subdivision Kintore Lake
  • Address 10205 Kintore
  • Year Built 2000
  • Square Feet 10302

This offering is a once in a lifetime opportunity! The 8,000 square foot (160,000 cubic feet volume) contemporary masterpiece is a magnificent collaboration between a prominent structural engineer, whose works include the world's tallest building Partronas Towers in Malaysia and a renowned New York architect, whose works include Filene Center at Wolf Trap Farm Park, in McLean Virginia and Mann Music Center in Fairmont Park, Philadelphia. The 18 acre parcel is comprised of 2 separately deeded waterfront lots, each with their own septic, well and dock. The main house with 300 windows, bi-level in-ground pool and spa sit majestically on the 8.5 lot with 8 feet MLW water depth at the dock. The second 8.5 acre lot hosts the 2 story barn styled after the main house. It includes 3 parking spaces with operable doors, three stalls, a wash stall, and a feed stall. On the second floor is a 2 bedroom, 1 bath apartment. In addition to the barn, there is a large paddock with two separate areas separated by a fence and a turnout shed that can be entered from either side of the paddock. This lot has 4 feet MLW at the end of the dock.

Listed by Robert D Lacaze of Long & Foster Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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3526 Hampden Dr Trappe MD 21673

Trappe, MD3526 Hampden Dr

Price$4,675,000

Est. Mortgage: $/month

MLS Number MDTA2002524

  • Single Family
  • LocationType Creek/Stream
  • Address 3526 Hampden Dr
  • Subdivision Hampden
  • Bathroom 8

HAMPDEN Circa 1663 Trappe, Maryland located between Easton and Oxford, Hampden is reported to be the oldest surviving brick residence in Talbot County. On the still waters of Sawmill Cove, Hampden is comprised of two parcels totaling 24 acres. With West/Southwest exposure on the creek and a mature canopy of trees around the house, the setting is bucolic and steeped in time. The main residence is a one- and one-half-story, l-shaped brick dwelling with a five-bay façade. There are four bedrooms with a first-floor primary suite. Quietly removed from the rest of the house, the primary provides a study/library with exemplary millwork, fireplace, and gracious views of Sawmill Cove along with separate ensuite baths. Formal living and dining appointments blend with casual spaces including a remarkable sunroom, open kitchen and family rooms, quintessential Eastern Shore Mud Room, second-floor guest suites, studio, and office join in a remarkable assembly of form, function, and historic significance. Additional improvements complement the setting including an original smokehouse, pool with changing rooms/summer kitchen, a two-bedroom guest accessory, farm office, workshop, greenhouse, and dock with five feet at mean low tide. The grounds of Hampden are complemented by a mature canopy of trees along with open space for agriculture, livestock, or habitat restoration. The location on La Trappe Creek is a proven waterfowl staging area on the sheltered waters of the cove.

Listed by Coard A Benson and Schuyler G Benson of Benson & Mangold,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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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5911 Elston Shore Rd Neavitt MD 21652

Neavitt, MD5911 Elston Shore Rd

Price$4,500,000

Est. Mortgage: $/month

MLS Number MDTA140742

  • Single Family
  • LocationType River
  • Address 5911 Elston Shore Rd
  • Subdivision None Available
  • Bathroom 6

BREATHTAKING PRIVATE WATERFRONT ESTATE Turnkey 10-acre family Compound 1.5 hours from Washington DC and Baltimore, 2.5 hours from Philadelphia, and minutes from the nautical charm of St. Michaels. The recently constructed Main House and Carriage House, and the renovated Guest House invite numerous configurations to accommodate 14 guests. Every room affords gorgeous sunrises and spectacular water views at the confluence of the Tred Avon and the Choptank Rivers and the Broad Creek. Experience southerly breezes in a park-like setting at the Pool and 125' Dock with seating area, 2 power lifts, a swim/kayak platform and 4' MLW. Exceptional craftsmanship and finishes provide the ultimate in Chesapeake living. "Windsong"

Listed by Clifford E Meredith of Meredith Fine Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 2022
* 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 2022 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 July 2, 2022. 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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