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Saint Michaels Real Estate, Homes and Condos for sale

All Saint Michaels homes currently listed for sale in Saint Michaels as of 10/15/2019 are shown below.  You can change the search criteria at any time by pressing the 'Change Search' button below.

If you have any questions or you would like more information about any Saint Michaels homes for sale or other Saint Michaels real estate, please contact us and one of our knowledgeable Saint Michaels REALTORS® would be pleased to assist you.


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30
$4,200,000
24671 BEVERLY RD, Saint Michaels MD 21663
5
BEDS
9
BATHS
8,416
SQFT
$499
$/SQFT
8.95
ACRES
1963
BUILT
"Second Tree--beautiful house on 34+ acres (6 parcels, Tax Map 32, Parcel 103, Parcel 150, Lots 2 thru 6) with extensive landscaping, pool, tennis court, pond, pier with 20,000 lb. lift and deep water, western exposure with gorgeous sunsets. 9,000+ sq. ft. house has 5 bedrooms, 6 full bath, 3 half baths with multiple casual and formal rooms--river room, library, office, many more!"
* PRICE LOWERED - $4,950,000 TO $4,200,000 
32
$4,150,000
24528 BEVERLY RD, Saint Michaels MD 21663
5
BEDS
6
BATHS
9,210
SQFT
$451
$/SQFT
10.14
ACRES
1859
BUILT
"Wake up to the sights and sounds of tranquil San Domingo Creek on this historic waterfront estate. Relax with your morning coffee in the rose garden or on the extended dock enjoying the privacy Beverly Manor offers. Spend the day walking around St. Michaels exploring the Chesapeake Bay Maritime Museum and boutique shops that dot the main strip. Kick back at a brewery, distillery, or winery if you~re looking to lighten things up. Retreat back to Beverly for lunch on the back porch, watching the boats cruising by, or hop on your own boat from your deep water dock. Welcome visitors to their well-appointed guest house. As dinner is prepared in the gourmet chef~s kitchen, relax in the adjacent family room with family and friends. When it is time to sit, choose from the elegant dining room or the enclosed rear porch. As the evening winds down, take in the sunset sitting on the patio or around a fire pit while enjoying the breeze off the water. Retire back to the sitting room for a few laughs before heading to bed. Then rise and repeat..."
* PRICE LOWERED - $4,900,000 TO $4,150,000 
30
$3,950,000
209 TALBOT ST, Saint Michaels MD 21663
20
BEDS
20
BATHS
20,000
SQFT
$198
$/SQFT
0.70
ACRES
1900
BUILT
"Five Gables Inn & Spa - Lovely Expandable Commercial Hotel (currently 20 rooms) Nestled in St Michaels, Maryland - Talbot County - 45 minutes Bay Bridge, 1 1/2 hr Baltimore, Washington, Philadelphia - 4 hrs driving distance from largest population base in America. OPPORTUNITY to acquire a well-performing Inn in an upscale prospering market - Extremely high barriers to entry - Ownership downsizing"
82
$3,795,000
24710 NEW POST RD, Saint Michaels MD 21663
4
BEDS
6
BATHS
9,132
SQFT
$416
$/SQFT
2.35
ACRES
2005
BUILT
"Custom-built waterfront estate located within 2 miles of historic St Michaels situated on 2+/- acres brings together the needs of the most discerning of buyers. The house enjoys an unusually generous elevation that gives way to breathtaking vistas over Miles River to the Eastern bay & beyond. Well-manicured, lush grounds, custom millwork, separate guest quarters above garage."
46
$2,999,999
24062 N PORTERS CREEK LN, Saint Michaels MD 21663
4
BEDS
7
BATHS
9,698
SQFT
$309
$/SQFT
1.93
ACRES
2008
BUILT
"Beautiful waterfront estate on almost 2 +/- acres with broad water views of Porter's Creek with dock and heated pool. Stone house consisting of four bedrooms each with their own baths, a huge lower level recreation room with bath and storage area and a three car garage. Butler's pantry, sunroom and bathroom downstairs. Many amenities with plenty of storage space."
69
$2,975,000
8824 BOZMAN NEAVITT RD, Saint Michaels MD 21663
4
BEDS
5
BATHS
5,227
SQFT
$569
$/SQFT
12.30
ACRES
1800
BUILT
"Experience this wonderful St Michaels waterfront home accessed by a long tree lined driveway situated in a peaceful setting on Harris Creek. First floor open layout, eat in kitchen, formal dining room, family room and living room. The master bedroom is on the first floor with two bathrooms, sitting area and bar with gorgeous water views and a private patio. There are 2 guest suites upstairs with private bathrooms. One of the suites has a 2nd bedroom. There is a guest house overlooking the pool and water with living room , eat in kitchen, powder room on the 1st floor and two bedrooms that share a bathroom on the 2nd floor. This historic home has been stunningly restored and expanded to take advantage of the beautiful wide water views."
92
$2,590,000
7116 PEA NECK RD, Saint Michaels MD 21663
3
BEDS
3
BATHS
2,863
SQFT
$905
$/SQFT
20.30
ACRES
1993
BUILT
"Spectacular 20 Acre St Michaels Waterfront Retreat!! Privacy and nature abound in this beautifully expanded 3 bedroom home with additional 1 bedroom guest apartment over the detached garage. Major renovation and expansion in 2006 include expanding main house with new 1st floor master bedroom and bath, new dining room, sun room, three fireplaces, decks, finished 3rd floor with balconies, new pool, new dock, new detached garage with workshop and 1 bedroom guest apartment above. Enjoy breathtaking sunsets every night with expansive views of Edge Creek. This is truly a nature lover~s paradise less than 4 miles from the shops and restaurants of St Michaels. It must be seen to be appreciated. Please contact listing agent for more information or a private tour."
65
$2,500,000
25192 WATCH GOOSE FARM RD, Saint Michaels MD 21663
4
BEDS
5
BATHS
3,926
SQFT
$637
$/SQFT
6.19
ACRES
2017
BUILT
"Brand new, absolutely gorgeous St. Michaels home on the deep waters of Solitude Creek. Bright open floor plan with hickory floors, beautiful windows, top of the line gourmet kitchen with large island, family room with stone fireplace, built-ins with copper wood storage, fabulous first floor master suite with luxurious bath and walk-in closet. Private office with custom mosaic.Waterside deck, screened porch, private pier with 5.5' +/- MLW and room for pool!"
88
$2,450,000
23946 MOUNT MISERY RD, Saint Michaels MD 21663
4
BEDS
5
BATHS
4,052
SQFT
$605
$/SQFT
4.42
ACRES
1805
BUILT
"Click video camera to view drone tour!Classic Eastern Shore residence offering charm and comfort, in a private 4 acre country setting only two miles from St. Michaels (17th Century port town, with shops and restaurants, and home of the Chesapeake Bay Maritime Museum). Mount Misery is an historic brick residence built in 1805/1806 on land granted by Lord Baltimore in 1667. Original doors, floors, mantels in early section. 5 fireplaces. Cedar shingle roof. Residence restored in 1954 by Pittsburgh industrialist Ralph Tennant using plans drawn by H. Chandlee Forman, Ph. D, A.I.A. Residence expanded and greatly ungraded by current owner in 2004, plans by Paul Richard, A.I.A., with large modern bathrooms and closets. Landscape design by Barbara Paca, Ph. D., O.B.E. of Preservation Green, with flowering shrubs, patios, garden rooms. Trails to explore, small woodland park, stream. Pool, sauna, tennis court. 135 ft pier with 5 ft MLW, water and electric, and two power boat hoists. Plenty of crabs, fish and oysters! 700 ft of stable shoreline on Rolle's Creek/San Domingo Creek, with easy access to the Chesapeake Bay. Beautiful water views with sunsets over the water. Easton, Baltimore and Wilmington each about 1 hr 45 min. Easton Airport, and Memorial Hospital ."
* PRICE LOWERED - $2,900,000 TO $2,450,000 
96
$2,195,000
8195 CHURCH NECK RD, Saint Michaels MD 21663
4
BEDS
4
BATHS
6,692
SQFT
$328
$/SQFT
35.48
ACRES
1825
BUILT
"Baybury Bank Farm first time listed for sale in over 34 years. This 35+ acre farm is sited on the beautiful waters of San Domingo creek. Offering 4 tillable fields, pastures and outbuildings for livestock. The barn offers stables, tack room and running water outside. Pastures have automatic waterers. The brick federal style home was built in 1825 and offers 4-bedrooms, 3.5-baths, 4-wood burning fireplaces, original hardwood floors, exposed wood beams, screened waterside porch with a second floor balcony above.Dock with electric, 10,000lb boat lift, large slip previously housed a 40~+ boat. The home overlooks the water and well manicured lawn, pastures and fields. The detached 2-car garage includes a uniquely designed 2-bedroom carriage home bringing a bit of natureindoors. The spacious 3-bedroom, 2.5-bath guest/caretakers home offers original hardwood floors, upgraded kitchen, multiple living spaces, master bedroom & family room addition and a screened waterside porch. Located less then 2 miles from historic St. Michaels."
96
$2,195,000
8195 CHURCH NECK RD, Saint Michaels MD 21663
4
BEDS
4
BATHS
6,692
SQFT
$328
$/SQFT
35.48
ACRES
1825
BUILT
"Baybury Bank Farm first time listed for sale in over 34 years. This 35+ acre farm is sitedon the beautiful waters of San Domingo creek. The brick federal style home was built in 1825 and offers 4-bedrooms, 3.5-baths, 4-wood burning fireplaces, original hardwood floors, exposed wood beams, screened waterside porch with a second floor balcony above.Dock with electric, 10,000lb boat lift, large slip previously housed a 40~+ boat. The home overlooks the water and well manicured lawn, pastures and fields. The detached 2-car garage includes a uniquely designed 2-bedroom carriage home bringing a bit of natureindoors. The spacious 3-bedroom, 2.5-bath guest/caretakers home offers original hardwood floors, upgraded kitchen, multiple living spaces, master bedroom & family room addition and a screened waterside porch. The property is a great place for horses or livestock,improved w a barn including stables and tack room, run in shed and fenced pastures. 4-tillable fields. Located less then 2 miles from historic St. Michaels."
48
$1,975,000
9241 DEEPWATER POINT RD, Saint Michaels MD 21663
4
BEDS
4
BATHS
6,200
SQFT
$319
$/SQFT
13.90
ACRES
1974
BUILT
"Unique 14 ac on Long Haul Creek close to Miles River Yacht Club, Pete Dye Links Perry Cabin Golf Course & St Michaels. Three building compound has 14 rentable boat slips, legally rentable guest cottage off dock, 2 story bonus building w 4 car garage, dramatic 30x44 second floor with large windows on all 4 sides. Main house has 2 bedrooms, study, living rm, 2 dining areas, large sunroom & spacious kitchen w fireplace. This property is a MUST SEE!!"
29
$1,880,000
24640 YACHT CLUB RD, Saint Michaels MD 21663
6
BEDS
5
BATHS
2,968
SQFT
$633
$/SQFT
3.10
ACRES
1910
BUILT
"Bay Cottage Waterfront home is a rare find as it holds a dual license as a Bed and Breakfast or short term vacation rental. The property includes the Main House, A Caretaker cottage, A Carriage house with 2 master suites on second floor. Large cottage/pool house. A Fantastic property within walking distance to Town of St Michaels. This home offers a private dock with 5 boat slips steps away from main house."
54
$1,439,000
7261 SOLITUDE RD, Saint Michaels MD 21663
3
BEDS
3
BATHS
2,716
SQFT
$530
$/SQFT
4.22
ACRES
1890
BUILT
"St Michaels waterfront, the Steamboat House, had a total 2018-2019 renovation to perfection while preserving the historic ambiance of this 1890 gem. Private, tranquil location yet five minutes to St Michaels. NEW: in-ground pool, kitchen, bathrooms, roof, septic, HVAC, plumbing, electrical, etc. All new from chimney caps to encapsulated crawlspace! Generous patio, huge screened porch, 2019 Weems dock. Can be purchased turnkey."
48
$1,389,900
960 MAREA TER, Saint Michaels MD 21663
4
BEDS
4
BATHS
3,300
SQFT
$421
$/SQFT
1.52
ACRES
2019
BUILT
"OPEN HOUSE Saturday from 1-3pm. Last chance to own waterfront home in this brand new construction subdivision in St Michael's will be completed soon! LAST LOT AVAILABLE-subdivision is sold out! Direct waterfront lot, with shared dock/piers included in the price. High end construction and finishes throughout, Two master suites, one on the first floor, Andersen windows, inground pool, large back deck over looking the water. You have to see this home to appreciate the quality. Designer kitchen, exotic wood flooring, quartz counter tops, waterfront master suite and so much more! Walking distance to downtown St. Michael's."
* PRICE INCREASED - $1,379,900 TO $1,389,900 
66
$1,295,000
107 W CHEW AVE, Saint Michaels MD 21663
4
BEDS
4
BATHS
2,798
SQFT
$463
$/SQFT
0.17
ACRES
2017
BUILT
"Built in 2017 with an historic aesthetic, up to date detail, and high-end finishes and fixtures, this is a rare opportunity to live in a new construction home in the heart of St. Michaels. This charming Colonial Revival with inviting covered front porch and tall 1st floor windows fits seamlessly in the Historic District.The interior was designed with today's lifestyle in mind. Living area, dining and deluxe kitchen flow from one to another and spill into a beautiful enchanting garden with charming separate summer house for outdoor dining and lounging. The kitchen invites chefs to create for friends and family and includes a Wolf gas range and large walk in pantry as well as ample storage and counter space. The first floor is completed with a sought after bedroom suite with luxurious en-suite bath and walk in closet. The second floor features a generous master suite and additional guest suite. Hickory floors, Quartz counter tops, a true masonry fireplace with marble hearth surround and cast-iron sinks and tubs blend today~s desired finishes with yesterday~s charm. Put your cars away in the detached cottage style, two-car garage and walk to the shops, restaurants, museums and services in the Historic District, and to the public dock, park, walking trail access and kayak launch at the end of the street.One-of-kind St. Michaels opportunity in turn key condition. Vacation now and retire later!"
55
$1,250,000
24830 DEEPWATER POINT DR, Saint Michaels MD 21663
3
BEDS
3
BATHS
2,875
SQFT
$435
$/SQFT
2.32
ACRES
1978
BUILT
"Fantastic waterfront martingham home offering broad views with 5 to 6 feet MLW and a sandy beach. Contemporary home with tall ceilings to take advantage of the views, Formal DR, family room with screened porch and first floor MBR and bath. Oversized 2 car garage, additional 2 BR on the 2nd floor. Enjoy a daily boat parade and ride your bike to downtown Saint Michaels or a round of golf at Harbourtown."
43
$1,250,000
7461 SOLITUDE RD, Saint Michaels MD 21663
3
BEDS
2
BATHS
3,542
SQFT
$353
$/SQFT
20.00
ACRES
1920
BUILT
"A Bit of Solitude St. Michaels- Mini Farm First time offered in 45 years! Unique property including 20 acres, Low Taxes / zoned Agricultural. Potential for multiple uses- Mini Farm, Horses, Home Contractors Business, Family Compound, Hunting Retreat, etc. Charming 3500 sq. ft. Farm House w/ Georgia Pine Floors and first floor master bedroom -Barn w/ Banquet Room & Bar, plus Large Office & Two 2 BR Apts., 8 Bay Pole Barn Mechanic garage, Workshop, Pond & Rifle Range **Possible owner financing"
66
$1,195,000
7130 PEA NECK RD, Saint Michaels MD 21663
5
BEDS
3
BATHS
5,068
SQFT
$236
$/SQFT
17.64
ACRES
1760
BUILT
"Traditional 18th century Tidewater Colonial sited on 17.63 picturesque acres. This home boasts 4 bedrooms, 3 baths, a large loft overlooking Edge Creek, and a waterside great room with other additions added from 1950 to 1980. Waterside inground pool makes it the perfect entertaining home and is currently being used as a sought after Vacation Rental By Owner. 2 car detached garage with workshop and studio. Additional improvements include: One bedroom Guest House with Living, Kitchen, Bath, sunroom, and laundry room. 350 feet of rip rap shoreline. 110 foot pier with boat shed. Attached greenhouse.This property is an historic waterfowl staging area. With a southern shore, nearby woods, hedgerows and wetlands, it is sure to please the nature enthusiasts."
* PRICE LOWERED - $1,295,000 TO $1,195,000 
60
$949,900
328 PERRY CABIN DR, Saint Michaels MD 21663
4
BEDS
5
BATHS
3,015
SQFT
$315
$/SQFT
0.14
ACRES
1984
BUILT
"PRICE REDUCTION -- UNDER APPRAISED VALUE - RARELY - AVAILABLE 4 bedroom, 4.5 bath end unit offers first floor master suite with stunning upgraded bath, DEEP WATER BOAT SLIP w/electric/water and amazing panoramic views of the Miles River and Fogg Cove Harbor. Walk to town/Inn at Perry Cabin. This home is move-in ready, HOA takes care of the property so you can relax and enjoy...boating, community beach & tennis/pickle ball courts. For more information check out: https://www.thehomesatperrycabin.com/"
* PRICE LOWERED - $989,000 TO $949,900 
65
$943,500
340 PERRY CABIN DR, Saint Michaels MD 21663
4
BEDS
5
BATHS
2,748
SQFT
$343
$/SQFT
0.15
ACRES
1987
BUILT
"JUST REDUCED - With its entertaining views of the Miles River, boat traffic, sail boat races, and log canoe regattas, this unit offer the best of St. Michaels. Elegant end unit features entertview so fthe Miles River, four en-suite bedrooms and this is the only unit that offers a 1st floor master with wood burning fire place (currently used as family room), sunroom, and waterside deck, perfect for entertaining or private dinners. First level offers formal living room with gas fireplace and built-in book cases, formal dining room, gourmet kitchen with granite counter tops, butlers pantry with granite counter tops, wine fridge, sink, powder room and laundry. Water views from foyer, living room, family room sunroom, 2nd level master and en-suite waterside bedroom. 2nd level features three additional en-suite bedrooms including 2nd master with walk-in closet, den/office with built-in bookcases, additional storage/closets and pull down attic access. Attic is floored and offers additional storage. This waterfront townhome includes a deeded boat slip with water and electric, 6 ft. MLW and can accommodate up to 40 ft. boat. The community also offers access to a private beach, tennis courts, pickle ball courts, and private footbridge to neighboring Inn at Perry Cabin with easy access to the town of St. Michaels, resturants and shops. Please visit www.thehomesatperrycabin.com to learn more about the community. You can also download brochures for the home and community from documents."
* PRICE LOWERED - $995,000 TO $943,500 
30
$899,000
24181 OLD HOUSE COVE RD, Saint Michaels MD 21663
3
BEDS
2
BATHS
1,792
SQFT
$502
$/SQFT
3.83
ACRES
1984
BUILT
"Reminiscent of the charming cottages the owner remembers from childhood summers on Cape Cod, this cedar sided home has been updated with style, New kitchen and baths, encapsulated crawlspace, new windows.. Just 3 miles into Historic St Michaels and sited on a quiet cove off San Domingo Creek. The large waterside porches (one screened, one open) make a perfect place to relax. New sewerage disposal area approved 7/9/19 so waterside pool can be installed."
40
$899,000
207 E CHESTNUT ST, Saint Michaels MD 21663
5
BEDS
4
BATHS
2,728
SQFT
$330
$/SQFT
0.06
ACRES
2002
BUILT
"A unique opportunity to own a new home in the heart of the Historic District. Built in 2002 on the site of an 1850 home, this 3 story, 5 BR home combines the charm of the old with modern amenities. Reclaimed beams from the original structure can be found in the kitchen and den/office. A great room combining living and dining has wood floors and a beautiful PA field stone fireplace flanked by built in cabinetry. Owner's suite has private bath, dressing area w/ 2 walk-in closets. 4 additional BRs plus a loft/office/multi-purpose room. Private, fenced backyard, nicely landscaped with stone patio. Close to the water and many amenities of this charming Eastern Shore town."
56
$830,000
105 CHERRY ST, Saint Michaels MD 21663
5
BEDS
4
BATHS
2,799
SQFT
$297
$/SQFT
0.37
ACRES
1860
BUILT
"Location, location, location! Steeped in history back to when Frederick Douglas lived on Cherry Street & worked the farms of Perry Cabin & Martingham. This stunning, prominent home is located on a full block of property only steps to the waterfront & many of the best attractions in St. Michaels. One of the only properties in St. Michaels that have a full rentable guesthouse. Valuable rear lot has subdivision potential. Plenty of green, open space & room for pool. Main house is beautifully renovated adding modern amenities while retaining it's historic integrity. Walk to the harbor, restaurants, shops & museums. Watch the people go by on your screened in front porch. High ceilings, 4 fireplaces, Gorgeous updated kitchen & baths. 1st flr master or family room, butlers pantry, nannys quarters. Guesthouse can be used as a home business. Plenty of offstreet parking for 4+ cars plus a detached garage off the guesthouse. Finished attic good for extra bedroom or studio. First time on market in 70 years. Nothing else like it at this price in St. Michaels! Owner has found new home of choice. Make offer!"
* PRICE LOWERED - $840,000 TO $830,000 
 
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