410-822-1415 | Benson & Mangold Real Estate

Barb Watkins | 410-310-2021 | bwatkins@easternshorehomes.com

Eastern Shore Homes Real Estate by Barbara Watkins

St. Michaels, MD

A Great Place to Visit, an Even Better Place to Call Home

Are you dreaming of finding a community to call home that offers a bounty of outdoor activities, boutique shops, and exceptional eateries? If so, you’ve been searching for the rich cultural scene of St. Michaels.

St, Michaels, Maryland is one of those places that has something for everyone – fantastic real estate, history, art, adventure, and beautiful natural attractions. While the local charm is hard to beat, all of your basics are covered too – from grocery stores to convenience shops. You can reach this small, picturesque, well-preserved, waterfront village by boat, a short drive from Annapolis, Baltimore, Washington D.C., or Philadelphia, or fly into our municipal Easton Airport.

Real Estate Offerings

Whether you have a young family and are looking for a home near the water, or are retired and looking for a golfing community to enjoy, St. Michael’s historical and contemporary real estate offerings have everything from luxury estates to cottages.

Waterfront: If you have always dreamed of waking up with a breathtaking view of the sunrise over a serene body of water, St. Michaels may be your dream come true. The immaculate waterfront properties vary from deep water protected homes to residences with broad water, wildlife, and tranquil views. Love boating? Your next home could have harborfront access or a view of one of the many local marinas! No matter your budget or style preference, there is a home along the Miles River perfect for you.

In Town: Given St. Michael’s welcoming and beautifully developed downtown, in town living is very popular. If you are looking for new construction or a more historic home, you will find what you’ve been dreaming of in one of St. Michael’s welcoming neighborhoods. Do you want your home to have a lot of character and be recognized as part of the town’s history? Pick from one of the unique Colonial and Victorian period style homes available. Prefer new construction? There is a variety of Craftsman and contemporary style homes in the area, as well. By living in town, you will have premium access to all of the attractions of St. Michael’s – restaurants, museums, and shops!

Communities: No matter if you’re looking for a golfing or a water access community, St. Michaels offers some of the most pristine and inclusive communities in the Eastern Shore area. There is Chance Hope Farm, a small waterfront community with 50 luxury single family homes or Martingham, a golf course neighborhood with single family homes, townhomes, villas, and condos. There is also Back Creek Landing, a small, single family home community or Rio Vista, a small waterfront community that offers more modest in land homes and waterfront homes. The communities and neighborhoods in St. Michaels are inviting, beautiful, and peaceful.

Community Attractions

Things to Do & See

If you decide to call St. Michaels home, you will never have a shortage of things to do! This waterfront village offers an array of festivals, art galleries, museums, and historical walking tours you can enjoy with friends and family. If you love the outdoors, there are championship golf courses, river cruises, fishing excursions, and sailboat charters. For thrill and adventure seekers, you can kayak, bike, or sail the historic Skipjacks.

Looking for the best shopping in the area? St. Michaels will keep you satisfied with its variety of locally owned jewelry, clothing, specialty food, and home decor shops. Visit regularly to make sure you don’t miss out on a special find! Hoping to discover one of a kind art pieces to decorate your new home? Enjoy the impressive and perfectly curated local art galleries.


One of St. Michael’s claims to fame is their decadent offering of Chesapeake Bay cuisine. Local seafood restaurants offer the freshest fish, crabs, and oysters you have ever tasted. A few of our restaurants include:

  • Awful Arthur’s Seafood Company
  • Chesapeake Landing
  • St. Michaels Crab & Steak House
  • Theo’s Steaks, Sides & Spirits
  • Crab Claw

Beyond the phenomenal seafood, St. Michael’s offers an eclectic array of local eateries, including Italian, contemporary French, Irish, and even an old-fashioned soda fountain! Locals and visitors alike can’t get enough of:

  • Ava’s Pizzeria & Wine Bar
  • Carpenter Street Saloon
  • Blackthorn Irish Pub
  • Limoncello Italian Restaurant & Wine Bar
  • Foxy’s Harbor Grille

The area is also known for its high-end wineries and breweries which offer frequent tasting events. If you want a full tasting experience, we give the following establishments our highest recommendation:

  • Eastern Shore Brewery
  • Lyons Distilling Company
  • St. Michaels Winery

Whether you want a waterfront dining experience or a casual, relaxing bistro lunch, you will find it in St. Michaels!

Ready to find your “forever” home in St. Michaels? Contact Barbara today!



























If you are looking for a fun, exhilarating, all embracing town that offers an array of unusual boutique shops, exceptional eateries, an old fashion soda fountain, wineries, a brewery, scenic river cruises, and educational museums St. Michaels, Maryland is the perfect place to live.

The St. Michaels Real Estate community offers a multitude of housing choices from historic “in town” houses, waterfront cottages, luxury waterfront estates, golf community homes, water access community homes, to condominiums, townhouses, and interior home sites. St. Michaels, Maryland Waterfront properties vary from deep water protected homes, broad water view, wildlife and tranquil views to harbor front and marina view homes. In town you will find colonial period homes, new homes, craftsman, Victorian and contemporary style homes.

St. Michaels, Maryland is  an area of diverse activities, and accommodations of all kinds  including, short term rentals, year round rentals, overnight boat  dockage, hotel, or upscale lodging at The Inn at Perry Cabin. You can enjoy festivals, art gallery tours, wine and beer tastings, championship golfing, river cruises, fishing excursions, or sailboat charters and of course the best crabs, and oysters on the east coast.

You can reach St. Michaels, Maryland by boat, a short drive from Annapolis, Baltimore, Washington DC or Philadelphia, or fly into our municipal Easton airport. This small well- preserved, waterfront village is a great place to visit and an even better place to call home.

Just outside of Historic St. Michaels, Maryland is a small waterfront community called Chance Hope Farm, consisting of 50 luxury single family homes. These St. Michaels MD homes range from 3,000 to 8,000 square feet, and all are waterfront, along the Miles River. Chance Hope Farm is within walking distance of the Harbortowne Golf Course and marinas. Prices range from $1 million to $4 million.

A mile past St. Michaels is the golf course neighborhood of Martingham, with about 150 single family homes and 200 townhomes, villas and condos, surrounding the Harbortowne Golf and Conference Center. This waterfront community features an 18-hole championship course designed by the legendary Pete Dye, and is within a short distance of Historic St. Michaels, The Miles River Yacht Club, marinas, and eclectic and diverse shopping. Prices start at about $275 thousand for condos and can range up to $2.5 million for luxury waterfront estates.

Back Creek Landing is a small community of 60+ single family homes. The community includes walking trails, ponds, a pier and water access to San Domingo Creek, and is within walking distance of shopping and Historic St. Michaels. This is one of the newest St. Michaels Maryland homes neighborhood. Prices range from $450,000 to $800,000.

The Community of Rio Vista is a small St. Michaels MD waterfront community just outside of Historic St. Michaels in Talbot County. Rio Visa is a more modest community consisting of several styles and ages of homes.  These St. Michaels MD homes range from 1,000 to 5,000 square feet.  Situated on The Miles River, offering broad water views, water access, picnic area and community boat dock. Rio Vista is close to schools and other attractions the Village of St. Michaels has to offer. Prices range from $150,000 for inland homes to $2,500,000 for waterfront homes.

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The data relating to real estate for sale on this web site comes in part from the Metropolitan Regional Information Systems, Inc . Last Updated 06/22/2017. Portions Copyright © 2017 Metropolitan Regional Information Systems, Inc All rights reserved.