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St Michaels Homes with Virtual Tours

Scroll down to browse homes in St. Micheals, MD featuring virtual tours. Select the "Virtual Tour" button below a listing to view the tour. Please note that some of these listings may have virtual tours coming soon.  

St. Michaels Maryland Homes for Sale with Virtual Tours

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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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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

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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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24699 Deepwater Point Dr Saint Michaels MD 21663
Pending

MLS Number MDTA2002504

  • Single Family
  • Subdivision Martingham
  • Square Feet 3925
  • Bathroom 4
  • Bedrooms 4

This is the one you have been waiting for! Attractive custom built Cape Cod on 2 + Acres capturing the incredible views of Long Haul Creek to the Miles River and beyond. First time being offered since built; you will rarely get this kind of opportunity to own home that truly has it all. Deep Water (6 MLW) in protected cove with private pier for the avid boater, waterside heated gunite pool with spa, unusually elevated lot, public Water/Sewer, and located just about a mile from all the amenities of historic downtown St. Michaels! Inside you will find a home that possesses a feel of casual elegance and the Eastern Shore Lifestyle. There are 4 bedrooms including a primary suite that features a fireplace, waterside balcony, and large walk-in closet. The overall layout is very open and offers a formal living room, dining room, and great room with fireplace. The Waterside kitchen has an open flow to the screened in porch and two outdoor patio areas where you can entertain your guests while looking out over the water. Other notable features of the house include cavernous amounts of storage space, freshly painted wood siding, and a two-car garage. Located in the highly sought-after private community of Martingham that borders the award-winning Pete Dye golf course known as The Links at Perry Cabin. Don't miss your chance to own a house that is ideally located by land and sea to enjoy the very best of the Eastern Shore Lifestyle.

Listed by C Edwin W Mangold 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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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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24382 Oakwood Park Rd Saint Michaels MD 21663
Pending

MLS Number MDTA2002834

  • Single Family
  • LocationType Creek/Stream
  • Subdivision Oakwood Park
  • Square Feet 2732
  • Bathroom 4

"Under the Oaks "- rare waterfront find, completely renovated with meticulously appointed luxury! From the gated entrance of flowering camellias in a parklike setting, this property is stunning! Upon entering enjoy expansive waterfront views throughout the entire back of the house. Exquisite interior design in every room integrating light, space and water. New floors, ceilings, ship lap, custom designed gourmet kitchen complete with Wolf cooktop and double oven. Large living room with walls of glass and stone fireplace that flows into the dining area with amazing views; all custom renovated with precise attention to detail. Every room including the two water view primary suites has been thoughtfully renovated. First floor primary bath boasts radiant heated tile floor, walk in shower, custom vanity, each bath features designer lighting and lovely quartz countertops. Designed to enjoy the warmth and comfort of waterfront living “Under the Oaks” easily accommodates many family and friends, configured with four bedrooms (septic is sized for a 3 bedroom) and four full baths. Plus bonus room/ office. Highest end custom fit and finish throughout. Newly rebuilt shared dock with private slip, 10+ MLW and historic pavilion. New metal roof, solar lighted cupola, underground sprinkler system and remarkable flower gardens. Too many upgrades to list. Detached one car garage with workshop, potting room, carport and small courtyard End your days relaxing on one of the two back porches or in your Adirondack around the fire pit at water's edge. Minutes to St. Michael's. 5 homes share community pier & pavilion . Sold furnished except for artwork, personal items and minor exclusions. Seller prefers post settlement occupancy through the end of July.

Listed by Katherine M Christensen 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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968 San Domingo Ct Saint Michaels MD 21663
Pending

MLS Number MDTA2000025

  • Land
  • Acreage 1.15
  • LocationType Bayfront
  • Zoning RESIDENTIAL

Price Repositioned - Spectacular Waterfront Lot - Last available lot in Hatton's Garden/ San Domingo Cove. Pier already in place and boat lift approved. Bring your own builder. Full set of custom builders plans available with accepted offer. St Michael's premier waterfront subdivision. This waterfront community features amazing waterfront views and is in walking distance to downtown St Michael's.

Listed by Chevelle M Welsh and Adam E Light of Monument Sotheby's International Realty

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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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7968 Pond Haven Ct Saint Michaels MD 21663
Pending

MLS Number MDTA2002612

  • Single Family
  • Address 7968 Pond Haven Ct
  • Subdivision Back Creek Landing
  • Square Feet 2921
  • Bathroom 3

Rare offering with beautiful views of the pond and nature preserve in the Back Creek Landing community in St. Michaels. This spacious attractive colonial with covered front porch features an open floor plan with a large primary bedroom suite on the first floor. The open kitchen concept flows seamlessly into living and formal dining rooms and has easy access to the screened in porch overlooking the pond. A den provides space for a home office, TV room or library. Two additional bedrooms with a full bath plus a large family room can be found on the second floor. With 3,300 sq. ft. of living space not including the garage, this is the largest of the floor plans that were offered in the community. With 9 ft. ceilings on the first floor, gleaming wood floors, lots of windows to let in light, a beautiful staircase and curved rail on the second floor landing overlooking the two story living room, this home offers many exceptional features. In 2021, substantial improvements were made including a new roof, new 2nd floor HVAC, new water heater and in the years before the 1st HVAC was replaced and the crawlspace encapsulated. This house also has a plug in for an electric car. Back Creek Landing is a few minutes away from the Historic District of St. Michaels. The community has its own kayak dock on San Domingo Creek, and nature trail system to enjoy wildlife and water views.

Listed by Carolina Barksdale and 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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1023 Monroe Ave Saint Michaels MD 21663

Saint Michaels, MD1023 Monroe Ave

Price$649,000

Est. Mortgage: $/month

Pending

MLS Number MDTA2002470

  • Single Family
  • LocationType River
  • Address 1023 Monroe Ave
  • Subdivision Rio Vista
  • Year Built 2004

Enjoy all the amenities of Eastern Shore living in this spacious, modern, move-in ready, water-access home with several dramatic design features and great open entertainment space. Substantial upgrades have been made to this house over the last couple of years, including a new roof and HVAC. This versatile, custom-built home has a first-floor primary bedroom suite with a large walk-in closet, twin-sinks and an oversized shower with bench. The high-ceilinged great room is accented with an efficient gas fireplace. A chef's kitchen, with gas cooking and two ovens, connects the formal dining room with the everyday dinette that overlooks a private paver patio, and fenced and landscaped grounds. The airy and bright garden-view sunroom as a separate entrance to the patio. A front sitting room, tucked behind French doors, serves as a quiet place to read or could be an ideal home office. A large pantry, powder room and laundry complete the first floor. The open, wooden staircase in the great room leads to a second-floor balcony and three bedrooms, or two bedrooms and a media room, with full bath. An unexpected and large walk-in storage room completes the second floor. The home has an extended, attached two-stall garage beautifully finished with storage cabinets. A large garden shed is equipped with electrical service. The home is served by public water and sewer and is close to a fire hydrant, a rare, but important safety feature. It is shaded by mature trees and is minutes from the shops, restaurants and the harbor of Historic St. Michaels. The St. Michaels Nature Trail is a short distance away. Community residents also enjoy access to a private picnic park on the Miles River and a marina with a kayak launch and seasonal small-boat slips for rent. All this, and no expensive town taxes.

Listed by Carolina Barksdale 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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9273 Martingham Dr Saint Michaels MD 21663
Active With Contract

MLS Number MDTA2002570

  • Single Family
  • LocationType Adjoins Golf Course
  • Address 9273 Martingham Dr
  • Subdivision Martingham Inn
  • Bathroom 4

Does being close to golfing, boating, boutique shopping, bistros, parks & schools appeal to you? This meticulously maintained 3 bedroom, 2 and a half bath Cape Cod is truly made for both entertaining and everyday living, with plenty of space and fabulous views.. You can call it home on the 10th tee of the Pete Dye designed private golf course, The Links at Perry Cabin. So it has you on location. Inside, it features a traditional floor plan with lots of natural light, oak wood flooring, and a statement wood burning fireplace. The L-shaped kitchen is modest with custom cabinetry, granite countertops, and stainless steel appliances. A beautiful brick decorative arch adorns the cooking range and refrigerator. You will definitely enjoy the park like views and relaxing in the four season sunroom. Additionally, a spacious rear deck expands the length of the home for endless outdoor entertaining.

Listed by Julie A. Stevenson of Shore Living Real Estate

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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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9521 Quail Hollow Dr #602 Saint Michaels MD 21663
Active With Contract

MLS Number MDTA2002690

  • Condo
  • LocationType Adjoins Golf Course
  • Subdivision Martingham
  • Year Built 1997
  • Bedrooms 3

Fabulous Martingham Condo, located adjacent to the "Links at Perry Cabin Golf Course." This home has been lovingly maintained and is a wonderful spot to relax and enjoy life on the Eastern Shore. A few of the amenities include: main level bedroom ( current owners use as a den/office), 2 spacious upper bedrooms each with en suite bathrooms, balcony off the primary bedroom, new glass sliders, new carpet. Main level features an open living/dining room with fireplace, built in cabinets, crown molding, wood flooring, and new glass doors leading to a backyard patio. Martingham offers a waterfront park to their residents. Come see for yourself all this home offers

Listed by Deborah W Meredith 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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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