Benson & Mangold Real Estate, 31 Goldsborough St, Easton, MD 21601 410.822.6665 | Office

Search Homes:

St. Michaels MD Homes for Sale

Some of the homes in St. Michaels MD date back to the 1600s. You’ll also find custom builds, contemporary homes, waterfront estates, and everything in between. The picturesque harbor on Maryland's Eastern Shore boasts exceptional seafood restaurants and plenty of outdoor activities. Browse current single family homes for sale in St. Michaels MD below.

St. Michaels MD Real Estate Listings

Call Chuck Mangold at 410-924-8832 with any questions or to schedule a private tour.

Save time! Create a free account to save your favorite listings and get notified when similar properties become available. You can view all homes in Talbot County here.

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

$
$
%
$/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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

10295 Sherwood Manor Saint Michaels MD 21663

Saint Michaels, MD10295 Sherwood Manor

Price$3,295,000

Est. Mortgage: $/month

Pending

MLS Number MDTA2002994

  • Single Family
  • Address 10295 Sherwood Manor
  • Subdivision Claiborne
  • Year Built 1996
  • Bathroom 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: 5.7% 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

7214 Solitude Rd Saint Michaels MD 21663

Saint Michaels, MD7214 Solitude Rd

Price$2,695,000

Est. Mortgage: $/month

MLS Number MDTA2003058

  • Single Family
  • LocationType River
  • Address 7214 Solitude Rd
  • Subdivision St. Michaels
  • Bathroom 4

Welcome to this beautifully maintained waterfront home on Solitude Creek which lies just minutes between beautiful St. Michaels and Easton. This home has panoramic views over Solitude Creek offering sunsets nearly year round. The far shore of the creek is wooded and undeveloped. There is a waterside firepit, and an in-ground swimming pool. The approach to the home is along a driveway that is lined with huge Oak trees, both beautiful and shade producing. The main residence is loaded with impeccable, high end, custom finishes, moldings, high ceilings and an open floor plan that is great for entertaining in one of the two rooms that opens to the "perfect" gourmet kitchen. There is a private pier and protected shoreline. Located only minutes to the Historic town of St. Michaels with its restaurants, lodging and museum or to Easton or to the Oxford Bellevue Ferry which takes you across the Tred Avon River to Oxford. The location and quality of this home can't be beat.

Listed by Ray R Stevens 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

8377 Bozman Neavitt Rd Saint Michaels MD 21663
Pending

MLS Number MDTA141200

  • Single Family
  • LocationType Creek/Stream
  • Subdivision None Available
  • Bathroom 5
  • Year Built 1977

Welcome to "Heron Cove", the ultimate property offering complete PRIVACY, yet only minutes to St. Michaels! Sited on two parcels totaling 30.16 acres (all in conservation), this incredible point of land offers 180 degrees of water views over Broad Creek with 1900' of water frontage (much is rip-rapped). The wooded lane is stunning as it meanders to the house, and, on arrival the setting is truly picturesque. The house, built by Harry Ball, is actually two structures connected by a glassed breezeway, has hardwood floors throughout, and was designed at the time for the expanding family. The original house was an Acorn design built in 1977. It includes a spacious kitchen, large great room with cathedral ceilings and fireplace, mudroom and laundry on the first floor. Upstairs are two bedrooms with ensuite baths and a loft. In 1984, the second structure was added and includes a first-floor bedroom and bath, lovely living room with fireplace (never used) and a wonderful waterside all season sunroom, which has been a favorite gathering place. Upstairs are two additional bedrooms with spacious closets, and a hall bath. A composite deck (a few years old) is accessed by both sides providing wonderful entertaining space for all. To the east side of the home is a large gunite pool with creek views, updated systems and a new polaris. To the west is the protected pier which has 4'MLW (buyer to verify). Additionally, there is a large shed along the drive with lots of storage for boats, etc. and has electric. A hunting blind is located on the shoreline as well. This wonderfully maintained home is being sold by the estate and their preferred closing is 6/30 or after. All information on the conservation easement and right-of-way from Bozman-Neavitt Rd. will be provided upon request. PLEASE do NOT drive down the lane without permission!

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

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

24047 N Porters Creek Ln Saint Michaels MD 21663
Pending

MLS Number MDTA2002944

  • Single Family
  • LocationType River
  • Subdivision Porters Pride
  • Year Built 1985
  • Bathroom 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.

$
$
%
$/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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Lot 1 Meadow St Saint Michaels MD 21663

Saint Michaels, MDLot 1 Meadow St

Price$799,880

Est. Mortgage: $/month

MLS Number MDTA2003270

  • Single Family
  • Address Lot 1 Meadow St
  • Subdivision Bentley Hay
  • Bedrooms 4
  • Bathroom 3

Custom 2 story just released. Open floor plan with 2 story foyer. Have a similar home under construction for you to tour. All the bells and whistles included. Upgrades include fireplace, LVP luxury floors,upgraded tile, quartz countertops in kitchen. Luxury superbath and more.

Listed by George M Bailey of Keller Williams Flagship of Maryland

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

107 E Chestnut St Saint Michaels MD 21663

Saint Michaels, MD107 E Chestnut St

Price$719,000

Est. Mortgage: $/month

Pending

MLS Number MDTA2002896

  • Single Family
  • Address 107 E Chestnut St
  • Subdivision St Michaels
  • Bathroom 2
  • Bedrooms 2

Character and charm abound in this beautifully restored Historic home in the heart of St Michaels! Circa 1820 although history suggests construction began between 1805-1820. There have been numerous significant improvements over the years with removal of the asbestos siding and the 2-story addition in 2003 to mention just a few. Plumbing & Wiring have been updated as well. Current Owners totally renovated the Kitchen and encapsulated the crawl space as well as added many architectural details to the home since they took ownership. You will not be disappointed with this meticulously & lovingly maintained home! A perfect blend of old and new! Enjoy the home, the gardens, the spacious insulated & heated outbuilding offering many possibilities and of course the close proximity to the Harbor, the Museum and all the wonderful boutiques and restaurants that St Michaels has to offer! Don't wait for an opportunity to view this lovely home on the best street in St. Michaels! All offers to be submitted no later than Monday, May 9, 2022 at 5 pm.

Listed by Leslie J Stevenson 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

7968 Pond Haven Ct Saint Michaels MD 21663

MLS Number MDTA2003462

  • Single Family
  • Subdivision Back Creek Landing
  • Address 7968 Pond Haven Ct
  • Year Built 2004
  • Bathroom 3

"Back Creek Landing" a Water privileged community just outside of Historic 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 into living and formal dining rooms and has easy access to the screened in porch overlooking the pond. A separate area 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, wood floors, lots of windows to brighten the home. 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 the crawlspace was 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 Edwin M Matthews 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

310 N Talbot Saint Michaels MD 21663

Saint Michaels, MD310 N Talbot

Price$695,000

Est. Mortgage: $/month

Pending

MLS Number MDTA2002036

  • Single Family
  • Subdivision St. Michaels Pointe
  • Address 310 N Talbot
  • Bedrooms 3
  • Square Feet 2200

Custom built home in desirable St. Michaels Pointe Community. Open floor plan with gas fireplace and gourmet kitchen outfitted with stainless steel appliances, granite countertops and island with breakfast bar. This home's layout is ideal for entertainment and a first floor den provides room for an office, library or den. Spacious layout on second floor with large family room, huge primary suite with oversized walk in closet and primary bath with soaking tub and custom walk in shower, and two additional bedrooms. There is only one more lot left in the community to built this house again. Don't miss your opportunity to be part of this community.

Listed by Carolina Barksdale 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

410 Bentley Ave Saint Michaels MD 21663

Saint Michaels, MD410 Bentley Ave

Price$685,000

Est. Mortgage: $/month

Pending

MLS Number MDTA2002942

  • Single Family
  • Subdivision Bentley Hay
  • Address 410 Bentley Ave
  • Square Feet 2386
  • Bedrooms 3

Fabulous location, Bentley Hay offers in town living without town taxes . Located on a cul de sac with water views from porch, living room , sun room and one bedroom. Extremely well maintained house with many upgrades.

Listed by Cornelia C Heckenbach 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

9199 Martingham Dr Saint Michaels MD 21663

MLS Number MDTA2003504

  • Single Family
  • Subdivision Martingham
  • Address 9199 Martingham Dr
  • Year Built 1988
  • Bathroom 3

This light filled contemporary with dramatic glass wall opening to a large deck overlooking the park and the famous Links at Perry Cabin has been revitalized by a wonderful renovation. This truly move in ready comfortable sized three bedroom home features all new floors, new bathrooms, new walk in closet, new lightening, new kitchen with gleaming granite counter, stainless steel under warranty appliances. Open the sliding doors and enjoy your morning coffee or lunch al fresco on the flag stoned patio in a park like setting, add a fire pit and life is good. From the living room step out on the spacious deck and sip your ice tea or cocktail . This home is just less than 5 min to historic St Michaels with all the famous restaurants and shops. Link at Perry Cabin memberships are available for the avid golfers. The Martingham homeowner waterfront park is in short proximity to sit and watch the boats go or drop a kayak in the river and go explore.

Listed by Cornelia C Heckenbach 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.

Save 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 July 6, 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.

Get In Touch Today

Contact Chuck