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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

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24629 Beverly Rd Saint Michaels MD 21663

Saint Michaels, MD24629 Beverly Rd

Price$12,750,000

Est. Mortgage: $/month

MLS Number MDTA140044

  • Single Family
  • Address 24629 Beverly Rd
  • Bathroom 7
  • Bedrooms 5
  • Square Feet 10309

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, and custom architectural elements. 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

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$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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24724 New Post Rd Saint Michaels MD 21663

Saint Michaels, MD24724 New Post Rd

Price$3,495,000

Est. Mortgage: $/month

MLS Number MDTA140354

  • Single Family
  • Address 24724 New Post Rd
  • Bathroom 6
  • Bedrooms 3
  • Square Feet 8833

Welcome to St. Michaels! This spectacular site on the Miles River has 180 degree unobstructed water views. This French country style house maximizes water views with a rear elevation full of doors and windows from all of the main rooms. Enjoy the waterside terraces at the main and upper floors as you relax and watch the promenade of sailboats during the summer season and the migratory birds in the fall. Spend weekends exploring the river from your pier with its 4 ft MLW. Pick your spot on the river to watch the St. Michaels July 4th Fireworks with your boating party. All this in a small neighborhood of double cul-de-sacs with the The Links at Perry Cabin golf course and the attractions of St. Michaels nearby. The house was solidly built of extra heavy steel and wood framing finished in stucco above the exposed foundation wall of stone veneer with a decorative water table, rounded copper covered dormers for a low maintenance facade. The house is L shaped with the side wing containing the three-car garage with its doors facing away from the street. The motor court's surface of cobbled stone pavers leads up to bluestone steps at the front entrance with a porch framing the view of the stunning dual Art Nouveau styled mahogany doors with inlaid vertical panels below round glazed panels. The front doors open onto a vista through the spacious two-level foyer and living room to the water views. Each level of the foyer is detailed with inlaid hardwood floors and coffered ceilings uplit to feature their copper faux finish. The cross vista from the upper entry ends at the sumptuous master suite and the open plan kitchen - breakfast area - family room at the other end. The kitchen has all the features prized by gourmet cooks-beautiful cabinetry, granite countertops, large island with a Gaggenau range across from the upper counter for bar stools and water views from both the island and kitchen sink at the side wall. The corner two-story family room has a fireplace at one interior corner freeing up the two exterior walls for diagonal water views from its walls of windows and doors. Rear tall transoms of the two story space provide additional sunlight. The side exterior French door leads to an elevated lawn area with a perimeter wall of stone that could be excavated for a pool or large hot tub and the exterior door that faces the pool has a full bath/changing space. One-third of the main floor plan contains the sumptuous master suite with the waterside bedroom, fireplace, his and her baths, including a jacuzzi tub and steam shower and two walk-in closets. The other bedrooms are located on the second floor and at the top of the stairs is a library-TV area. Between two bedrooms is a cozy space that could be a sitting area with its French door to a terrace. The corner third bedroom is opposite a space that is currently outfitted as a home gym. At the opposite corner is another open plan space that would be a great playroom. The upper level of the garage wing was originally designed as a bedroom-living suite with its own stairs down to its own exterior door. Two additional bedrooms could be added in these spaces with ease as well as an elevator. Unbelievable water views, low maintenance exteriors, high ceilings and unique details-a must see!

Listed by Fred I Rider III of TTR Sotheby's International Realty

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$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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24718 Beverly Rd Saint Michaels MD 21663

Saint Michaels, MD24718 Beverly Rd

Price$3,000,000

Est. Mortgage: $/month

Pending

MLS Number MDTA2000282

  • Single Family
  • Address 24718 Beverly Rd
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 5319

Wonderful 51.5 acre waterfront estate in prime location between Easton and St. Michaels. Just 75 minutes from BWI airport ,1 1/2 hr from D.C. and Baltimore, and 3 hr from NY. Property offers complete privacy and extends from Pea Neck Rd to Folly's Cove Rd. Roughly 35 acres are currently tilled and the remaining are in pasture and around the house. Beautiful entrance with circular drive leads you to the French/federal style brick home whose interior boasts 4 BR/4.5 BA. Great views of Folly's Cove and the property can be seen from all rooms including the renovated kitchen and comfortable family room. The master bedroom with it's high ceilings, sumptuous bath, and large deck were added by the current owners and has it's own private stairs. A gorgeous brick breezeway with pretty formal garden connects the 3 car garage with full 2 BR guest apartment above. Multiple rooms attached to the garage include large workshop, office space, possible art studio, and more. The protected pier has been re-decked with new stringers in 2021 and has an electric lift and 3'MLW. The shoreline is rip-rapped and the cove offers sanctuary to many species of wildlife. In addition there are 2 large ponds which make this a hunter's/wildlife enthusiast's paradise. The large Morton barn includes 5 stalls, feed room, wash stall, tack room, and large hay loft. 5 fenced pastures (1 with a turn out shed) are conveniently accessible. Adjacent are 2 sheds offering equipment storage plus a large greenhouse. There is also room for a waterside pool. No further sub-division of parcel is possible.

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

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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7238 Drum Point Rd Saint Michaels MD 21663

Saint Michaels, MD7238 Drum Point Rd

Price$2,995,000

Est. Mortgage: $/month

Pending

MLS Number MDTA141422

  • Single Family
  • Address 7238 Drum Point Rd
  • Bathroom 5
  • Bedrooms 4
  • Square Feet 5895

Far Horizons is where the very best of privacy, location, views, and convenience all come together in this amazing, and architecturally significant St Michaels estate. Enjoy massive southwestern floor to ceiling views from this meticulously renovated Broad Creek estate. Designed by pioneering DC architect Chloethiel Woodard Smith, this one-of-a-kind, one-level home showcases unparalleled mid-century modern charm with rich wood tones and colorful accents that complement the breathtaking views from every room. Be amazed by the view from multiple terraces, both the kitchen and bedroom courtyard and large garden to be enjoyed from the bedroom and family room. Enjoy energy efficient, multi-zoned geo-thermal HVAC in the main house. Well-planned professionally landscaped grounds with colorful flowers and plantings at every turn on the 8.85 park-like acres with 550' +/- rip-rapped shoreline, private pier with 10,000 lb boat lift, 2 jet ski lifts and kayak lift. Fabulous modern pool with proper pool house built in 2011 with full kitchen, bath, outdoor shower. All located just two miles from historic downtown St. Michaels and less than ten miles from historic downtown Easton.

Listed by Chuck Mangold of Benson & Mangold,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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24490 New Post Saint Michaels MD 21663

Saint Michaels, MD24490 New Post

Price$2,750,000

Est. Mortgage: $/month

Pending

MLS Number MDTA2000922

  • Single Family
  • LocationType River
  • Address 24490 New Post
  • Bathroom 6
  • Bedrooms 4

Listed by Dawn A Lednum and Maureen M McHugh of Chesapeake Bay Real Estate Plus,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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24580 New Post Rd Saint Michaels MD 21663

Saint Michaels, MD24580 New Post Rd

Price$2,495,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDTA141302

  • Single Family
  • Address 24580 New Post Rd
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 4956

Matterport 3D Walkthrough Aerial Video First time offered! Enjoy panoramic views over the Miles River to Eastern Bay and beyond in the custom built retreat in the sought after community of Chance Hope Farm. Located just two miles from downtown St Michaels, a quick boat ride to the St Michaels marina for dinner, a short bike ride to town for ice cream and a stone's throw from the Links at Perry Cabin. This lovingly cared for and well-appointed home with 4 bedrooms and 3.5 baths has the room you need for entertaining and hosting friends and family for memory making long weekends and vacations. First floor primary suite is complete with walk-in closet and luxurious bath with water views. Hardwood floors throughout, cathedral and vaulted ceilings, built-ins, and Palladian and bay windows providing abundant natural light and broad water views. The grounds are complete with covered front porch, professional landscaping, waterside patio and pier with boat lift. Approximately 264' of rip rapped shoreline and 3+ feet of MLW. Some furniture and furnishings available.

Listed by Chuck Mangold of Benson & Mangold,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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934 Riverview Terrace Saint Michaels MD 21663
Active With Contract

MLS Number MDTA2000546

  • Single Family
  • LocationType Bayfront
  • Bathroom 6
  • Bedrooms 6
  • Square Feet 3735

Incredible waterfront property in St. Michaels with commanding views overlooking the Miles River. Completely renovated home with stunning upgrades and finishes throughout. The entire home was renovated in 2014 and added an upper level with 3 additional bedrooms, 2.5 bathrooms, sitting room, and an additional laundry room, no expense was spared. Main level features the Gourmet kitchen with marble countertops and a 6 burner stove with water views overlooking the dining area, living room, and sunroom. Enjoy the upgraded custom enclosed porch, perfect for year around use. 3 main level bedrooms including a handicap friendly Primary Bedroom with an ensuite bathroom featuring a roll-in shower. Upper level features a sitting room overlooking the water, and an incredible bunk room with 5 built-in beds. The backyard on the Bay is picturesque from the 500 sqft deck, surrounded by lovely landscaping. The large lawn brings you down to the dock with a 16k pound boat lift and jet ski lift, complete with lighting. Walking or biking distance to downtown St. Michaels and all of it's charms, this location and property are an amazing opportunity!

Listed by Conor Sullivan and David A Moya of KW Metro Center

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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205 Cherry St Saint Michaels MD 21663

Saint Michaels, MD205 Cherry St

Price$2,075,000

Est. Mortgage: $/month

MLS Number MDTA2000072

  • Single Family
  • LocationType River
  • Address 205 Cherry St
  • Bathroom 9
  • Bedrooms 7

Once in a lifetime opportunity to own a St. Michaels iconic landmark waterfront property in a premier in-town location! This grand historic home is on the biggest waterfront lot overlooking the St Michaels harbor. Breathtaking views of the "Honeymoon" footbridge, Hollis Park, the Patriot Tour Boat, marinas & Navy Point, the home of Chesapeake Bay Maritime Museum. The main building is distinguished by it's elaborate 2nd Empire Mansard slate roof and Colonial Revival columned porches. Zoned R2 residential with a current home based business run as Aida's Victoriana Inn Bed and Breakfast. It's the only B&B in St. Michaels with a full, separate two bedroom, two bath Innkeepers house which would make a beautiful guest house. The property can be subdivided into two waterfront houses. There are seven bedrooms with four waterside bedrooms including a main level primary suite with a large private deck and sweeping views of the harbor. All rooms have separate controlled cooling. Three rooms have fireplaces. Plenty of access to the water via a public kayak launch, free Town day boat parking, overnight boat slips at the Museum and year round slip rentals next door at Higgins Yacht yard. Full basement in the main house provides ample storage. There is onsite parking for 10 cars. Commercial sprinklers throughout. Fully furnished with old world charm. Price is the same with or without furniture. Purchase price includes everything needed to start your own B&B business plus access to reservation and accounting system. Service for 120 person events is included. Town of St. Michaels B&B Inn license is good for unlimited events including weddings. Buyer must apply for license before settlement. Excellent high elevation with no current flood insurance. Financials only available after an in-person showing & a signed non-compete. This is a residential purchase with the ability for a buyer to start their own business. Current business is not for sale. Please do not go on the property without an appointment. Listing agent must accompany any showings. Showings must be scheduled around occupancy with at least 24 hours notice. Access to all rooms may need several showing appointments. History, plat and Features Sheet in MLS documents.

Listed by Kate Koeppen of Chesapeake Bay Real Estate Plus,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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200 Cherry St Saint Michaels MD 21663

Saint Michaels, MD200 Cherry St

Price$1,975,000

Est. Mortgage: $/month

Pending

MLS Number MDTA141288

  • Single Family
  • LocationType Downtown
  • Address 200 Cherry St
  • Year Built 1799
  • Bedrooms 5

Built in 1799 and expanded in 1872, the prestigious Dr. Dodson House is a luxurious gem situated on a tranquil street in the heart of St. Michaels' Historic District which marries two hundred plus years of charm with modern amenities and conveniences. This stately Federal style brick colonial boasts a rich eastern shore history, including the location of a private residence, tavern, the town's first post office, a medical office and even a top-ranked bed and breakfast. It offers five bedrooms including four en suite bedrooms and a luxurious, private primary suite. The property can be used as either a private residence or for commercial purposes. While an historic home, it offers many exceptional, state-of-the-art features, including central air and a large eat-in commercial kitchen with a six-burner Vulcan stove and dual ovens. Expansive windows allow light to flood into its many high-ceilinged rooms. You can cuddle up during the winter near any one of the property's five handsome wood burning fireplaces. You may enjoy its carriage house complete with a parking garage. Adding to this property's extraordinary features are a wine cellar, award-winning gardens, and a premiere location a mere walking distance to St. Michael's vibrant downtown with its specialty shops and upscale restaurants. As you relax on the property's elegant two-tiered sawn baluster porch, you can imagine seeing Maryland-born abolitionist Frederick Douglass speak to crowds and reporters from its second level, as he did following a reconciliation meeting with his former slave master on the property shortly after the Civil War. This one-of-a-kind, exceptional residence offers a rare opportunity to own a significant piece of St. Michaels' noble, proud history. **Showings by appointment only**

Listed by Tracy Higgs Wagner of Meredith Fine Properties

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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24490 Tricefield Saint Michaels MD 21663

Saint Michaels, MD24490 Tricefield

Price$1,795,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDTA2000808

  • Single Family
  • Address 24490 Tricefield
  • Bedrooms 3
  • Square Feet 2826
  • Bathroom 3

It's always about location, location, location!!! This meticulously maintained waterfront home on San Domingo Creek in Tricefield boasts 5' mlw in St Michaels with no town taxes! Enjoy almost 4.5 acres of privacy with beautifully landscaped grounds and room for a pool. The home consists of 3 bedrooms, 2.5 baths with a spacious waterside Great Room, Dining Area & Kitchen with vaulted ceilings, a wood burning fireplace as well as a gas corner fireplace for ambience! Or you can relax in the cozy Den watching a movie or reading your favorite book - you will have built-ins & a wood stove on chilly days with an adjoining powder room. The first floor primary bedroom has lovely water views and opens to a roomy waterside screened porch for complete enjoyment! Beautiful hardwood floors are throughout the first floor! You'll also enjoy a very spacious pantry as well as a designated Laundry Room. Upstairs are two bedrooms & a second full bath with separately zoned heating and air. There is room for expansion as well as a waterside pool! There are so many amenities to list that you just need to come see this one! You won't be disappointed!

Listed by Leslie J Stevenson of Long & Foster Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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974 San Domingo Ct Saint Michaels MD 21663

Saint Michaels, MD974 San Domingo Ct

Price$1,685,000

Est. Mortgage: $/month

Pending

MLS Number MDTA2000174

  • Single Family
  • Address 974 San Domingo Ct
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 3548

Spectacular sunsets on San Domino Creek w/6'MLW, boat house, dock. Renovation project or concept drawings available. Walk of ride a bike to St. MIchaels from this unique location.

Listed by Raymond R Staats of Benson & Mangold,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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23824 Mount Misery Rd Saint Michaels MD 21663
Pending

MLS Number MDTA2000738

  • Single Family
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2520
  • Year Built 1984

St. Michaels Waterfront. Comfortable, well-built 3 bedroom, 2 bath cottage sited on a premier 2.44 acre waterfront lot overlooking Broad Creek, 2-miles outside St. Michaels. The sunset views are extraordinary! Vaulted ceilings, ceramic tile floors, family room with wood burning fireplace, office, LR, nice MBR, 2 guest BR's, waterside deck and 100' dock w/boat lift. Very private, peaceful location. Walking and biking distance to downtown St. Michaels. 200' of protected shoreline with high elevation. Elevation certificate and survey are both recent. Home is out of the flood zone. Crawl space was recently encapsulated.

Listed by Edwin M Matthews of Benson & Mangold,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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Copyright 2021 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 September 27, 2021. 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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