Saint Michaels Real Estate, Homes and Condos for sale

All Saint Michaels homes currently listed for sale in Saint Michaels as of 02/20/2020 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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$5,200,000
8941 BOZMAN NEAVITT ROAD (RT. 579) RD, Saint Michaels MD 21663
3
BEDS
3
BATHS
4,459
SQFT
$1,166
$/SQFT
7.69
ACRES
2001
BUILT
"Just 4 miles outside historic St. Michaels, MD - Sited on 7.7 private, partially wooded acres, w/ 670' of protected shoreline at the confluence of Broad Creek and Sadler's Cove, the 4,500 sq. ft. main house was designed by Atelier 11. It is an impressive French Country-style home, constructed with stone, brick, antique wood beams and copper...built to last for centuries! This is a Wow house! The hanging stairs, custom 2 inch thick mahogany doors, 5 fireplaces (one on the waterside screened porch), beamed cathedral ceilings...Nothing compares. The quality, craftsmanship and finishes are amazing! Heated floors throughout, possible additional bedroom on the first floor. Over $3 million of recent upgrades and improvements, including: New garage/carriage house with finished game/media room above; New waterside swimming pool (heated) and outdoor kitchen; New pool house/guest cottage (very charming!); Extensive plantings designed and maintained by a professional landscape architect; New heavy duty boat lift (6' MLW) at the end of the private pier; New $150,000 generator (Powers the entire property). By car, St. Michaels is just a 5 minute drive and the town of Easton and Easton Airport are approx. 20 minutes away. By boat, some of the best fishing grounds and the open waters of Chesapeake bay are just a short, scenic boat ride away. The private dock on Broad Creek provides approx. 6 ft. of water depth at low tide."
$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 
$3,800,000
24528 BEVERLY RD, Saint Michaels MD 21663
5
BEDS
6
BATHS
9,210
SQFT
$413
$/SQFT
10.14
ACRES
1859
BUILT
"Over 8 acres of pristine waterfront land. The home was built in 1859 with an addition put on in 2009. Boasting 5 bedrooms, 4 full baths, and 2 half baths, the home is over 9000 sq. ft. with an attached 3 car garage. The 2 bedroom guest house has a 3 car garage and is at the entrance to the property. Over 1200 ft. of waterline includes a 100 ft deep water dock with boat lift. There is room to put in a pool in the back of the home as well."
* PRICE LOWERED - $4,150,000 TO $3,800,000 
$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."
$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
"Privacy and nature abound in this beautifully expanded 3 bedroom home with additional 1 bedroom guest apartment over the detached garage. 20 acre property includes farm, orchard, gardens and beautiful landscaping. Agreement with local farmer provides nominal income and keeps taxes low as a farm. 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."
$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
"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. 30' x 24' outbuilding."
$2,195,000
23946 MOUNT MISERY RD, Saint Michaels MD 21663
5
BEDS
5
BATHS
4,052
SQFT
$542
$/SQFT
4.42
ACRES
1805
BUILT
"Mount Misery circa 1805 is a classic eastern shore estate situated on 4 acres overlooking Rolles Creek to Broad Creek and beyond, with approximately 750 feet of shoreline. The exterior of the property has been professionally landscaped to taking full advantage of this private and serene property. Patios and gardens feature flowering shrubs throughout the seasons, and a walking trail and stream. Other exterior features included an in-ground waterside pool, pier with boat lift and 5'+/- MLW. The residence is the perfect balance between old and new with original elements such as doors, mantels and hardwood flooring yet offering a modern amenities and updated baths with the 2004 expansion. Water views from most rooms and sunroom with westerly vistas. Five period fireplaces are show pieces of the home. Enjoy all that the eastern shore has to offer including crabbing, fishing and fresh from the bay oysters! Just a few short minutes to historic downtown St Michaels for shopping, restaurants and marina. Convenient to Easton's jetport, and amenities and a perfect weekend getaway from Baltimore, Annapolis, Washington, D.C., or Philadelphia."
$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."
$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."
$1,590,000
603 MEADOW ST, Saint Michaels MD 21663
7
BEDS
7
BATHS
7,852
SQFT
$202
$/SQFT
0.37
ACRES
2005
BUILT
"This masterfully crafted, light filled, harbor side home is truly one of a kind. Within walking distance to the quaint downtown area, this incredible home offers luxurious living with enviable views of bustling St. Michaels Harbor. Dock your boat at the nearby marina, invite family & friends over for a weekend and entertain with ease. Enjoy a rainy day movie in the comfort of your own home theatre. Practice yoga, exercise or throw a dance party in the spacious, inviting studio space. Gourmet kitchen, great room, separate dining room, multiple wood-burning fireplaces, 7 bedrooms and 6.5 bathrooms, grand curving custom wood staircase, geo-thermal energy efficiency. Call today for your showing. So much to offer!"
$1,499,000
24564 NEW POST RD, Saint Michaels MD 21663
3
BEDS
4
BATHS
3,600
SQFT
$416
$/SQFT
2.24
ACRES
2002
BUILT
"Architect-designed 3,600 sq ft home sited on a premier 2.5 acre waterfront lot near St. Michaels. High elevation. Fabulous views across the Miles River. High ceilings. Bright, spacious rooms. Lots of waterside glass. Efficient radiant heated floors. Downstairs MBR. Fabulous kitchen. Nautical Room upstairs w/fireplace & mahogany/maple floors. Attached 3-car garage. Large waterside patio."
* PRICE LOWERED - $1,595,000 TO $1,499,000 
$1,380,000
7261 SOLITUDE RD, Saint Michaels MD 21663
3
BEDS
3
BATHS
2,716
SQFT
$508
$/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."
* PRICE LOWERED - $1,439,000 TO $1,380,000 
$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!"
$1,095,000
7171 DRUM POINT RD, Saint Michaels MD 21663
4
BEDS
3
BATHS
1,953
SQFT
$561
$/SQFT
3.09
ACRES
1969
BUILT
"Private and serene, this amazing Barrett Cove waterfront retreat is the perfect place to call home. Interior of this four bedroom home features hardwood floors, first floor waterfront master suite that walks out to deck, sunroom, and large kitchen with breakfast bar and dining area. Plenty of outdoor entertainment awaits you! Boating, fishing, crabbing, swimming in the in-ground pool or playing a round of tennis on your private tennis court. Backup generator. Convenient kayak launch, and a pier with boat lift and plenty of room to store all of your pool toys and kayaks in one of the outbuildings."
$950,000
7461 SOLITUDE RD, Saint Michaels MD 21663
3
BEDS
2
BATHS
3,542
SQFT
$268
$/SQFT
20.00
ACRES
1920
BUILT
"SIGNIFICANT PRICE IMPROVEMENT! 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"
* PRICE LOWERED - $1,100,000 TO $950,000 
$939,000
328 PERRY CABIN DR, Saint Michaels MD 21663
4
BEDS
5
BATHS
3,015
SQFT
$311
$/SQFT
0.14
ACRES
1984
BUILT
"PRICE REDUCTION -- JUST RECEIVED TOWN APPROVAL TO CONSTRUCT A NEW 14 x 16 DECK --This 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 - $949,900 TO $939,000 
$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."
$795,000
24181 OLD HOUSE COVE RD, Saint Michaels MD 21663
3
BEDS
2
BATHS
1,792
SQFT
$444
$/SQFT
3.83
ACRES
1984
BUILT
"Charming cedar shingled cottage just 3 miles to historic St Michaels, situated on private lot. Water views from the covered porch, the screened porch and almost all rooms. Light filled open floor plan, new bathrooms, new kitchen, new windows, encapsulated crawlspace. Fabulous outdoor spaces create summer living areas . There is a canoe landing next to the dock, perfect to enjoy summer nights by a fire pit.There is room for a waterside pool , the new SDA was established to secure a pool permit approval.The perfect Eastern Shore cottage to make lasting memories."
* NEW LISTING 
$710,000
114 W CHESTNUT ST, Saint Michaels MD 21663
4
BEDS
5
BATHS
3,276
SQFT
$217
$/SQFT
0.17
ACRES
1850
BUILT
"Located in the historic district, the Gingerbread House was built in 1850. This charming house has a lovely front porch & five working fireplaces. There is a full bath with a jet tub off of the breakfast room; which gives the option of converting the breakfast room into a downstairs master. There is a galley kitchen with stainless steel appliances, gas stove , Silestone counter top & exposed beams. The current owners have added french doors, carpeted both staircases, added fresh paint and wainscotting, and lighted wall sconces. The Dry Bar has a copper counter top and a stained glass window. There is access via the alley and two private parking places, a small garden shed as well as a heated workshop with fitted cabinets and attic storage. Tree lined street with brick sidewalks. View of covered bridge over the St Michaels walking trail. Next to lovely public park with kayak storage & kayak launch. Access to public waterman's dock. Prettiest house in town! Please schedule all previews & showing appointments through ShowingTime. Do not call office. One seller is a licensed realtor."
* PRICE LOWERED - $718,000 TO $710,000 
$699,000
124 GRACE ST, Saint Michaels MD 21663
4
BEDS
3
BATHS
1,538
SQFT
$454
$/SQFT
0.43
ACRES
1984
BUILT
"In town location, waterfront, just reduced $50,000... Let us show you this unique St Michaels home. Once inside this English Cottage with panoramic views of Back Creek you will find wide plank wood floors, vaulted ceilings with wood beams, custom wood fireplace surround and built ins are some the custom details making this home so special. First floor master suite with an additional master suite and 2bdr/ 2 full bath on 2nd floor. There is a wrap around screened in porch and private 2nd floor deck facing a generous back yard with beautiful tress , wildflower gardens and water view. JUST REDUCED $50,000"
* PRICE LOWERED - $750,000 TO $699,000 
$635,000
9001 N SAINT MICHAELS RD, Saint Michaels MD 21663
3
BEDS
2
BATHS
1,928
SQFT
$329
$/SQFT
5.45
ACRES
1890
BUILT
"A charming home, The Cottage on Long Haul sits on 5+ acres in beautiful St Michaels, This lovingly maintained waterfront home is surrounded by mature landscaping and sits on the Long Haul Creek. This great family home has 3 bdrm 1.5 bath and in ground pool,dock and all within walking distance of downtown St Michaels."
* PRICE LOWERED - $660,000 TO $635,000 
$595,000
304 PERRY CABIN DR #20, Saint Michaels MD 21663
3
BEDS
3
BATHS
1,836
SQFT
$324
$/SQFT
0.07
ACRES
1984
BUILT
"Overlooking St. Michaels' historic harbor, this bright, comfortable 3 bedroom, 2.5 bath townhouse would make an excellent summer/weekend get-away or full time home. As you can see, looking at the photos, the 1,836 sq. ft. townhouse is well maintained and it has surprisingly large rooms. The living/dining room measures, 14' x 33' and features a wood-burning fireplace and 12' wide triple sliding glass doors on the waterside. That door opens to a spacious, private deck, where you can sit back, relax and watch the boats entering and leaving the harbor. This Perry Cabin townhouse #304 (one of a total of 50 town homes) conveys with a premier deep-water boat slip with 50 amp electric, which will accommodate power or sailboats up to 40' in length. There are floating docks and canoe/kayak/paddle board storage racks, too. Amenities on the beautifully manicured 27-acre grounds also include two regulation synthetic tennis courts and two pickle ball courts. There is a hiking trail trough a natural wetlands, which leads to a picturesque island, where you will find a small sandy beach and lots of wildlife, including a variety of migratory birds; Ospreys; Bald Eagles; Ducks, Muskrats and Horseshoe Crabs. Another trail features a wooden bridge, leading to the Inn at Perry Cabin and downtown St. Michaels. If you love history, nature, picturesque harbor views, water sports and the relaxed Eastern Shore Lifestyle, then you should consider this affordable waterfront townhouse in St. Michaels, MD."
$549,000
9359 MARTINGHAM CIR, Saint Michaels MD 21663
4
BEDS
3
BATHS
2,100
SQFT
$261
$/SQFT
1.14
ACRES
1988
BUILT
"Comfortable one story home with views of pond and the Links at Perry Cabin golf course. Great open floor plan with new kitchen opens to family rm, dining and living. Huge screened porch and bluestone patio. Generous owner's suite has walk-in closet and full bath. Laundry room and separate mudroom. Lg. attached 2 car garage."
* PRICE LOWERED - $579,900 TO $549,000 
$549,000
108 N HARBOR RD, Saint Michaels MD 21663
4
BEDS
2
BATHS
1,410
SQFT
$389
$/SQFT
0.47
ACRES
1950
BUILT
"Location, Location. One of the best locations in St. Michaels with a partial view of the harbor. Lovely custom built home situated on two corner lots with a in-ground pool. Gorgeous 17 x 23 Sun room with water view."
* PRICE LOWERED - $590,000 TO $549,000 
 
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