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Talbot County Luxury Homes

Find all luxury homes for sale in Talbot County, Maryland including Easton, Oxford, Saint Michaels, and other towns. The properties shown below are priced at $1M and higher. You may also be interested in viewing all Eastern Shore luxury homes or Talbot County waterfront homes.

Talbot County Luxury Real Estate for Sale

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

21700 Camper Cir Tilghman MD 21671

Tilghman, MD21700 Camper Cir

Price$1,199,500

Est. Mortgage: $/month

MLS Number MDTA2002874

  • Single Family
  • Address 21700 Camper Cir
  • Subdivision None Available
  • Bathroom 5
  • Bedrooms 4

Enjoy unmatched views of the Choptank River, Harris Creek and Knapps Narrows with dramatic sunrises. Watch the crabbers, sailboats and wildlife . Room for the entire family with four large bedrooms and four and a half baths - Open floorplan with fireplace, double decker porches and room for the entire family. Private pier with boatlift and 4 FT MLW. In tax records, address is 21700 Choptank Circle - For GPS input Camper Circle.

Listed by Dawn A Lednum of Chesapeake Bay Real Estate Plus,LLC

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$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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$16,000,000

Est. Mortgage: $/month

MLS Number MDTA2002950

  • Single Family
  • Address 7751 Rollyston Dr
  • Subdivision None Available
  • Year Built 2016
  • Bedrooms 9

2 parcels totaling 91 acres on the Miles River. 4-level, furnished, 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.

Listed by Clifford E Meredith of Meredith Fine Properties

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$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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9400 Tilghman Island Rd Wittman MD 21676

Wittman, MD9400 Tilghman Island Rd

Price$3,500,000

Est. Mortgage: $/month

MLS Number MDTA2002476

  • Single Family
  • Subdivision Wittman
  • Bathroom 5
  • Bedrooms 5
  • Square Feet 5051

ONLY 7 MINUTES FROM ST. MICHAELS! A meticulously maintained home sitting on 13 acres of prime Chesapeake waterfront. The wooded acres of the property offer privacy and beautiful indigenous landscape. Heading toward the home a mile long tree lined will drive lead you past a clearing of fruit trees. Situated at the end of the drive will be the "Bay House". A stunning deck home architecturally designed to highlight open space and create massive amounts of natural light with expansive windows and soaring beamed ceilings. Wide water views of the Eastern Bay will meet you as you enter the home. One can see from Poplar Island to Kent Island in a glance. The open floor plan is perfect for entertaining family and friends or just sitting peacefully by a fire. A gourmet kitchen is perfectly situated between 2 dining areas. The home has 5 bedrooms and 4.5 baths. A first floor primary suite is a true retreat. Incredible views of the bay, fireplace, soaking tub and walk in shower all add to its solitude. The second floor opens to the great room and has 3 additional guest rooms and 2 baths. Each room with its own unique view of the property. Nature is abound in a home that brings the outside in. Osprey and Bald Eagles are regular passers by. An expansive 4th bedroom suite located on opposite side of home has its own private staircase. The first floor laundry area connects to a 4 car garage and has access to the outdoor BBQ area with underground gas hook up. The screened in porch with vaulted ceiling is the perfect spot to enjoy a crab feast. Just through the porches exterior door is a hot tub and all the wonders of owning your home on the water. This property also has an all season 2000 square foot pole barn on the property. Currently a great entertaining space and work shop with room for 2 additional vehicles. Seller recognizes need for pool and will offer a $75,000 credit for pool at settlement.

Listed by Jennifer Brown of Meredith Fine Properties

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$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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24047 N Porters Creek Ln Saint Michaels MD 21663
Active With Contract

MLS Number MDTA2002944

  • Single Family
  • LocationType River
  • Subdivision Porters Pride
  • Bathroom 3
  • Bedrooms 3

Gorgeous with coastal elegance and peaceful rural living, this idyllic Shingle home charms under the trees, surrounded by beautifully fragrant landscaping and relaxed greenspace. With cul de sac privacy and Eastern Shore views, the original 1985 single-level build has been transformed with inspired design and craftsmanship adding extraordinary light and thoughtful loft space. Greet guests from under the wood-clad portico then step inside where hardwoods, trimmed transitions, bright white hues, and endless windows line spaces for gathering, closing deals, creativity, and dinners with friends. While three restful bedrooms and two and a half baths soothe, the chef will enjoy an open kitchen of granite and high-end appliances. Complete holiday brunch for guests, or pack picnics for adventure exploring Porter Creek and Miles River. Just beyond the sunlit greatroom, look forward to morning coffee on the patio sheltered by an ivory-hued pergola, spend summers floating in the pool, and catch fire flies with little loved ones and a four-legged friend. At the nearly two acre property's end, unwind with a glass of cheer where evening wildlife views compete only with the house itself - lit with lightscaping, sunset reflection, and an emerald jacuzzi. While on tour, note the mudroom, airy loft, and high elevation, and visit the private dock where your watercraft awaits to drift into wildlife sanctuaries and Eastern Bay. Just three miles away, enjoy proximity to golf at the prestigious Links at Perry Cabin, and spend weekends in scenic Saint Michaels where antique shops and favorite seafood restaurants await.

Listed by Cornelia C Heckenbach of Long & Foster Real Estate,Inc.

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$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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28554 Ninth Dr Easton MD 21601

Easton, MD28554 Ninth Dr

Price$1,095,000

Est. Mortgage: $/month

Open House

MLS Number MDTA2003010

  • Single Family
  • Next Open House: Sat 05/21 1:00 pm. to 3:00 pm.
  • LocationType River
  • Address 28554 Ninth Dr
  • Subdivision Easton Club

Easton Club Waterfront! Much larger than the exterior suggests, this quality constructed home has over 4,000 square feet of living space, including a fantastic River Room that was added by the current owners. Sited on a double lot with over an acre to provide a private, parklike setting, yet centrally located in Talbot County and minutes to Easton, Oxford, and St. Michaels. Generous decking to take advantage of the water views with an outdoor kitchen and gas firepit. Fenced, private gunite swimming pool. There is a pier with two slips, and the water is navigable (Tred Avon River), however, it is shallow and tide dependent, but perfect for kayaking and paddleboarding. Main level primary bed/bath, separate main level office ideal for working from home, attached two-car garage. Three additional rooms and two full baths on the second level. A very open floor plan that lends itself to entertaining, gorgeous hardwood floors throughout most of the main level.

Listed by Deborah Mangold Lipscomb of Benson & Mangold,LLC

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$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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33488 Tuckahoe River Rd Easton MD 21601

Easton, MD33488 Tuckahoe River Rd

Price$1,248,000

Est. Mortgage: $/month

Pending

MLS Number MDTA2002008

  • Single Family
  • Subdivision Easton
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 4862

Welcome to Twin Peaks, situated high on the banks of the Tuckahoe River on over 2 acres,, this mid century modern home has been beautifully and meticulously renovated to take advantage of the sweeping water views. With over 4800 sq ft of space, this 3 level home has all the bells and whistles of the finest homes on the market today. The kitchen is a chef's delight, each bedroom has its private glorious bathroom Multiple living areas take advantage of the water view from each. The lower level is perfect with game and media rooms Perfect kids get away Best waterfront value in Talbot County

Listed by Maya D Hyman and Thomas C Williams Jr. of Compass

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$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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9380 Pennywhistle Dr Mcdaniel MD 21647

Mcdaniel, MD9380 Pennywhistle Dr

Price$1,960,000

Est. Mortgage: $/month

MLS Number MDTA2002828

  • Single Family
  • Address 9380 Pennywhistle Dr
  • Subdivision Nutcracker Point
  • Bathroom 5
  • Bedrooms 4

Meticulously maintained since it was built in 2003, this 5000 square foot residence has recently undergone a major update. Located just minutes from historic St. Michaels, this gracious home nestles among towering pines and overlooks the scenic Northwest Branch of Harris Creek. Enter the spacious foyer and admire the sunny living room with fireplace and a huge bay window with waterviews. To the left, an elegant primary suite with massive walk-in closet overlooks the same tranquil view. The primary bath includes a jetted tub, double vanity, bidet and walk-in shower. Walking past the formal dining room, an arched brick entry leads to the handsome kitchen with Amish built custom cabinets, large island, granite counters and pantry. The kitchen opens to the great room with warm American cherry floors and a soaring ceiling overlooking the water. A brick-floored screened porch leads to the newly-installed dock with 5' MLW and a 10' x 20' platform. Upstairs, which may be accessed by stairs or elevator, are two bedrooms that share a bath and a bedroom with en suite bath. A separate staircase in the mudroom (which has a full bath), leads to a bonus room.

Listed by Debra S Crouch of Benson & Mangold,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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7653 Tred Avon Cir Easton MD 21601

Easton, MD7653 Tred Avon Cir

Price$2,650,000

Est. Mortgage: $/month

MLS Number MDTA2003046

  • Single Family
  • Address 7653 Tred Avon Cir
  • Subdivision Waverly
  • Bathroom 5
  • Bedrooms 3

1.5-acre property on Jack's Cove off of the Tred Avon River. This house provides many spaces for entertaining inside and out. Spacious home with 3 bedrooms, 4 full baths, and 1 powder room. Expansive gourmet kitchen, dining area, family room with wood-burning fireplace, and sunroom. Living room with built-ins and wood-burning fireplace. Main level ensuites and upper-level primary suite with balcony overlooking picturesque backyard. Outdoor kitchen, shower, and family room with TV and wood-burning fireplace. Heated, inground, saltwater pool with automatic cover. Hot tub. Dock with water, electric, firepit, and boat lift. Detached 2-car garage with walk-in wine cooler and 1 bedroom, 1 full bath apartment above. Mature trees, a circular driveway, lawn irrigation, and riprapped shoreline complete the property. Conveniently located just minutes from Talbot Country Club, Downtown Easton, and a jet airport. Exclusions.

Listed by Clifford E Meredith of Meredith Fine Properties

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$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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24283 Deep Neck Rd Royal Oak MD 21662

Royal Oak, MD24283 Deep Neck Rd

Price$2,885,000

Est. Mortgage: $/month

MLS Number MDTA2002922

  • Single Family
  • LocationType River
  • Address 24283 Deep Neck Rd
  • Subdivision Royal Oak
  • Bathroom 5

This hidden gem with 1400' +/- on Irish Creek and 34 acres of beautiful woods is accessed by a private drive. The compound is the perfect retreat, offering privacy and incredible natural beauty, while only minutes from St. Michael's and Easton. The property offers a beautifully designed contemporary home, guest apartment, two-car garage, workshop, green house, sports court, sandy beach, pool, hot tub and screened gazebo that all take advantage of the serene views. The 3 bedroom, 2 bath, 2 half bath main home offers an open floor plan with large windows, sliding doors and skylights that seamlessly combine the beauty of the outdoor spaces with the interior. The spacious living room has vaulted ceilings and a wood burning fireplace, which connects with the kitchen, dining room and sunroom. Those spaces and the primary bedroom all have sliding doors that open to the waterfront and flagstone patio. The kitchen breezeway and pantry lead to the separate studio/office (unfinished, but great potential). The second-floor space has a half bath would be perfect for an office/studio or child's play room. Oak floors, vaulted ceilings, cedar paneling and ceilings, built-in bookcases compliment the home. A separate structure offers a two car garage, workshop and a gardeners delight green house on the ground level. The second floor is a cozy and fully equipped guest apartment with one bedroom, one bath, spacious kitchen/living room with French doors that open to balcony. Washer dryer, vaulted ceilings built in bookcases, views of the water compliment the apartment. Situated next to the house and along the water is a beautiful and recently refinished 40' x 18' Gunite pool with generous flagstone patio, separate above ground hot tub, screened gazebo and lush woodland gardens. There is a concrete basketball court that could also be equipped for pickleball. The dock has 4+ MLW depth.

Listed by Cynthia C Browne of Benson & Mangold,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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10295 Sherwood Manor Saint Michaels MD 21663

Saint Michaels, MD10295 Sherwood Manor

Price$3,795,000

Est. Mortgage: $/month

MLS Number MDTA2002994

  • Single Family
  • Address 10295 Sherwood Manor
  • Subdivision Claiborne
  • Bathroom 6
  • Bedrooms 6

Welcome to “Wing and Wing”, an exceptional 8.9 acre waterfront property located in one of the most sought after areas in Talbot County and just minutes from historic St Michaels. Charm abounds at every turn in this 6 BR/ 5.5 BA home and the seamless transitions between indoor and outdoor living spaces are unmatched. The picturesque drive takes in the peaceful pastures and leads to a landscaped circular drive. With spectacular water views and surrounded by stunning gardens and flowering trees/ shrubs, one can't help but feel a sense of privacy in this oasis. The interior offers a wonderful flow and provides a glimpse into the thoughtfulness taken when designing the home. The front slate porch, 2 story foyer, cathedral ceilinged library, first-floor primary suite, open kitchen, and wonderful large guest apartment with its separate entrance, all provide room for comfortable entertaining and easy living. Perhaps the most coveted spot is the waterside covered patio with its slate flooring, skylights, and treasured stone fireplace, enjoyed year-round by the current owners. Steps away is the beautiful gunite saltwater pool with waterfall and numerous seating areas and gazebo. Other special additions are an enclosed porch/sunroom, fabulous studio/workshop, large 3- car garage, and a most unique full height dry basement which provides endless storage. Interior features also include hardwood floors, 4 inside fireplaces, radiant heat, retractable awnings, and a deck off one of the upstairs bedrooms. 600' of mostly rip-rapped shoreline, a protected pier with lift and 4-5'MLW, 5-zone irrigation system, and multiple sheds on the property are just a few of the amenities. There is a controlling depth at the mouth of the cove but navigable for most boaters. Please contact listing agent for further information on this very special property.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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309 Bonfield Ave Oxford MD 21654

Oxford, MD309 Bonfield Ave

Price$2,495,000

Est. Mortgage: $/month

Pending

MLS Number MDTA2002544

  • Single Family
  • LocationType River
  • Subdivision Jacks Point
  • Address 309 Bonfield Ave
  • Square Feet 3661

It's all about the view! This unique waterfront compound, nestled on a quiet street just outside of historic Oxford, offers two charming homes with a pool and courtyard connecting the two. Just steps away from the shoreline, the main house offers broad waterfront vistas of Town Creek and further to the Tred Avon River. You can enjoy the best of both worlds of overlooking a quiet creek, with more active water in the backdrop and easy access to the Tred Avon, Choptank, and beyond for boating. Multiple porches and balconies offer endless opportunities to enjoy the views. The main house features a first-floor en suite bedroom/office, and two other bedrooms on the second floor, including the Primary bedroom. The primary bedroom has a gas fireplace, and a wrap-around balcony to take in your morning coffee or evening cocktail. The main level was designed with input from highly regarded architect Dr. Charles Burnette to take advantage of the water views from the dining, living, and sunrooms. The guest cottage will not disappoint your weekend company, with a white cheery kitchen, porch overlooking the private swimming pool, four bedrooms, and an office/family room with an adjoining full bath. There are 4 full baths in the guest cottage! The entire compound features 7 bedrooms and 7 baths split between the two homes. Outdoor features include a private dock with 4'MLW (buyer to verify), two slips for larger boats, kayak launch and floating dock at the bulkhead, a beautiful courtyard with a saltwater gunite pool as the centerpiece, an outdoor laundry facility for pool towels and recreation equipment, with an attached garage, recreation room, and garden shed. Extensive landscaping and fencing. This home exudes the charm of a Martha's Vineyard bungalow and is the perfect weekend retreat to share with friends and family. This property has a history of being a successful vacation rental, please inquire about previous income reports. Other features of note: Available high-speed internet access, town water, and sewer, in flood zone 'X', so no flood insurance is required.

Listed by Deborah Mangold Lipscomb of Benson & Mangold,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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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25610 Chance Farm Ct Royal Oak MD 21662

Royal Oak, MD25610 Chance Farm Ct

Price$2,750,000

Est. Mortgage: $/month

MLS Number MDTA2002560

  • Single Family
  • LocationType River
  • Address 25610 Chance Farm Ct
  • Subdivision Royal Oak
  • Bathroom 6

Property being sold "as is" to settle an estate. This 4 bedroom, 5 1/2 bath home has a bit of a European feel to it. When you first walk in there is a large open entryway. Beautiful wood floors upstairs and down, Spacious rooms, nice moldings, first floor owners suite with custom built-ins, wet bar, 2 walk in closets, bathroom suite, fireplace, and comfy waterside window seat. Kitchen with slate floors, walk-in pantry, gas cooking, warming drawer, tile counters, butlers pantry, and built-in toaster. Family room with volume ceilings, huge windows, fireplace and custom design wood floors. Cozy library/office with wood floors, formal living room with fireplace Second floor has 3 bedrooms and 2 full baths, one of which is ensuite. The unfinished bonus room would be great for exercise room, playroom, home theatre, etc. Separate first floor laundry room , large sun porch with flagstone floors and cathedral ceiling. The rear slate patio is huge and would be great for entertaining. Oversized 3 car attached garage that is heated and air-conditioned. & insulated doors, Automatic propane fired generator. Crawlspace appears to be conditioned and dry. Concrete shingle roof, Paver circular drive in front with tree-lined winding paved drive. Pier with lifts and deep water. Waterdepth measured 6 ft at low tide 4/5/22. Appears to be plenty of room for a waterside pool. An additional 90 + acres has a conservation easement and waterfront homesite, being offered separately MDTA2002562. Please do not drive on property without notifying agent.

Listed by Barbara C Watkins of Benson & Mangold,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 5.25% last updated on May 19, 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 May 20, 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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