28

Saint Michaels, MD Homes for Sale with Garage

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  • /72

    $525,000

    $50K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    204 E Marengo St, Saint Michaels, MD 21663

    Priced to Sell - Huge Price Improvement! Your St. Michaels weekend escape may be more attainable than you think.Trade the traffic and weekly routine for weekends in one of the Eastern Shore’s most beloved waterfront towns. 204 E Marengo Street offers the perfect combination of location, low-maintenance living, and your own private backyard oasis—ideal as a weekend retreat or primary

    Agent Photo

    Gretchen Wichlinski

    Compass

    204 E Marengo St, Saint Michaels, MD 21663
  • /36

    $359,000

    $16K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,800 Sq Ft

    24362 Widgeon Place Unit 5, Saint Michaels, MD 21663

    All resonable offers considered! Move in ready! Meticulously maintained 2 bedroom, 2.5 bath townhome offers comfort, privacy, and inviting living spaces throughout. The galley kitchen features a charming breakfast nook and flows into the dining and living area, highlighted by a wood-burning fireplace. Just beyond, a cozy sitting area opens to a brick patio overlooking a lovely backyard bordered

    Agent Photo

    Tracy Higgs-Wagner

    Meredith Fine Properties

    24362 Widgeon Place Unit 5, Saint Michaels, MD 21663
  • /20

    $339,900

    $20K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    9531 Quail Hollow Dr Unit 402, Saint Michaels, MD 21663

    Located in the desirable Martingham community, this two-bedroom, two-and-a-half-bath condominium offers comfortable living just minutes from historic downtown St. Michaels. The main level features a spacious living room with hardwood flooring and a wood-burning fireplace, a convenient half bath, and a full-season sunroom overlooking the backyard with direct access to the outdoor space. A detached

    Chuck Mangold Benson & Mangold, LLC

    9531 Quail Hollow Dr Unit 402, Saint Michaels, MD 21663
  • /32

    $995,000

    $54K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,250 Sq Ft

    109 W Marengo St, Saint Michaels, MD 21663

    This thoughtfully designed 4-bedroom, 3-bathroom home features an open-concept floor plan ideal for both everyday living and entertaining. The main-level primary suite provides a private retreat with a spacious walk-in closet and an en-suite bath complete with a double vanity and glass-enclosed shower. The living room is anchored by a cozy gas fireplace and flows seamlessly into the dining area

    Chuck Mangold Benson & Mangold, LLC

    109 W Marengo St, Saint Michaels, MD 21663
  • /27

    $598,000

    • 3 Beds
    • 2 Baths
    • 2,348 Sq Ft

    204 Lincoln Ave, Saint Michaels, MD 21663

    Rio Vista Community – No Town Taxes! Enjoy life in the desirable Rio Vista community, featuring exclusive resident access to a waterfront park on the Miles River. Located just outside historic St. Michaels, this home offers exceptional convenience with a grocery store, hardware store, restaurants, beauty salon, Pilates studio, YMCA, and garden center all just minutes away. This solid ranch-style

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    204 Lincoln Ave, Saint Michaels, MD 21663
  • /64

    $3,000,000

    • 4 Beds
    • 3 Baths
    • 2,815 Sq Ft

    23820 Mount Pleasant Landing Cir, Saint Michaels, MD 21663

    FALL IN LOVE WITH LIFE IN ST. MICHAELS!As summer fades, the Eastern Shore becomes even more captivating. Just one mile from vibrant downtown St. Michaels, this meticulously renovated waterfront residence offers easy access to seasonal festivals, exceptional dining, charming boutiques and year-round waterfront activities.Designed for effortless one-level living, the home combines

    Carrie Mock Engel & Völkers Annapolis

    23820 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
  • /34

    $490,000

    Open Sat 12PM - 2PM
    • 3 Beds
    • 3 Baths
    • 1,752 Sq Ft

    9521 Quail Hollow Dr Unit 605, Saint Michaels, MD 21663

    With extensive updating done less than three years ago, this home in the popular Martingham community shows beautifully! The spacious, open living room with hardwood floors and fireplace overlooks a pavered patio and lots of greenspace beyond. The kitchen is up to date and well designed, and a pocket door separates it from the first floor bedroom suite, which could also be a den or office.

    Debra Crouch Benson & Mangold, LLC

    9521 Quail Hollow Dr Unit 605, Saint Michaels, MD 21663
  • /23

    $375,000

    $24K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,743 Sq Ft

    214 Madison Ave, Saint Michaels, MD 21663

    Opportunity awaits! This 4-bedroom, 2-bathroom, two-level home offers a functional layout and plenty of potential for its next owner. The main level features beautiful hardwood floors, a galley kitchen, a separate dining room, and comfortable living spaces. Outside, you'll find a spacious yard with a storage shed, providing plenty of room for outdoor activities, gardening, or future

    Shelley Baden Berkshire Hathaway HomeServices PenFed Realty

    214 Madison Ave, Saint Michaels, MD 21663
  • /66

    $1,685,000

    • 5 Beds
    • 5 Baths
    • 4,728 Sq Ft

    9180 Saint Michaels Rd, Saint Michaels, MD 21663

    UNIQUE PROPERTY RIGHT OUTSIDE OF HISTORIC ST MICHAELS TOWN LIMITS ACROSS THE LINK AT PERRY CABIN. THIS FABULOUS HOME OFFERS SPACE FOR GATHERINGS WITH FAMILY OR FRIENDS BUT ALSO FEELS COZY FOR EMPTY NESTERS THAT LOVE TO ENTERTAIN. THERE ARE NO RESTRICTIONS THAT PROHIBIT VACATION RENTAL, THERE SHOULD BE SPACE FOR AN INGROUND POOL .ORIGINALLY BUILD IN 1973 THE CURRENT OWNER GUTTED THE HOME, ALL

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    9180 Saint Michaels Rd, Saint Michaels, MD 21663
  • /40

    $949,000

    Open Sat 12:30PM - 2:30PM
    • 4 Beds
    • 2.5 Baths
    • 2,168 Sq Ft

    111 Chesapeake Ave, Saint Michaels, MD 21663

    Beautifully upgraded and thoughtfully designed, custom finishes, and every modern convenience. The gourmet kitchen features dual fuel gas cook top and electric oven in professional grade stove, quartz countertops, professional grade appliances, and premium appointments, flowing seamlessly into warm hardwood floors and a cozy gas fireplace beneath a striking coffered ceiling. Beautifully curated

    Jana Meredith Meredith Fine Properties

    111 Chesapeake Ave, Saint Michaels, MD 21663
  • /25

    $799,000

    New Construction
    • 4 Beds
    • 2.5 Baths

    Lot 16A Meadow St, Saint Michaels, MD 21163

    Welcome to the quaint town of St. Michaels. Waterfront dining, history and small town feel are combined to give you a perfect home for full time or vacation home.Lacrosse homes is proud to present The Pointe.Time to make your personal selections. Make this home your personal statement.Pick the exterior colors, interior feature such as flooring, cabinets, countertops and more.Make this

    George Bailey Keller Williams Flagship

    Lot 16A Meadow St, Saint Michaels, MD 21163
  • /55

    $385,000

    $14K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,477 Sq Ft

    24700 Deepwater Unit 20, Saint Michaels, MD 21663

    Whether you are looking for a full-time residence, weekend retreat, or investment property, this unit is truly move-in ready. Situated in Martingham community just minutes from St. Michaels, shops, restaurants and surrounded by the Links at Perry Cabin golf course, this beautifully updated 2-bedroom, 2.5 bath townhome has been thoughtfully renovated with an emphasis on quality craftsmanship,

    Monica Penwell TTR Sotheby's International Realty

    24700 Deepwater Unit 20, Saint Michaels, MD 21663
  • /90

    $2,995,000

    • 6 Beds
    • 6.5 Baths
    • 4,656 Sq Ft

    1002 Wades Farm Ln, McDaniel, MD 21647

    With huge sunset views across Eastern Bay, this stylishly-updated property is the perfect retreat! The main house with three en-suite bedrooms overlooks a large waterside deck, saltwater pool and screened pool house. A wisteria-covered pergola leads the the 1920's two-bedroom guest house with wrap-around porch at the water's edge. The one-bedroom carriage house completes the compound. Great

    Debra Crouch Benson & Mangold, LLC

    1002 Wades Farm Ln, McDaniel, MD 21647
  • /42

    $775,000

    $85K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,027 Sq Ft

    807 Radcliff Ave, Saint Michaels, MD 21663

    ***BRAND NEW & MOVE-IN READY*** this Arts & Crafts home sits on a quaint corner lot in picturesque Saint Michaels, MD and is clad with high end finishes throughout. Step from the covered front porch into the luxurious kitchen which features stylish pistachio and linen cabinetry with satin bronze hardware, Z-Line appliances including a 36" dual fuel 6 burner range with champagne bronze

    Adam Ellison Long & Foster Real Estate, Inc.

    807 Radcliff Ave, Saint Michaels, MD 21663
  • /32

    $1,995,000

    • 4 Beds
    • 2.5 Baths
    • 3,028 Sq Ft

    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663

    Just 4 miles (five minutes) outside the historic town of St. Michaels, MD, this 15-acre property is located in an area of large, private waterfront estates. Over 400 ft. of protected shoreline. Westerly exposure provides Exceptional Sunset Views across the sparkling waters of Harris Creek! 120' x 6' pile-driven pier provides approximately 4' MLW. Sited near the water at the end of a long,

    Tom Crouch Benson & Mangold, LLC

    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
  • /53

    $2,149,000

    $100K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 3,017 Sq Ft

    7149 Drum Point Rd, Saint Michaels, MD 21663

    BACK ON THE MARKET WITH A NEW PRICE — DON’T MISS THIS EXCEPTIONAL WATERFRONT OPPORTUNITY!Tucked away in the highly desirable Drum Point neighborhood of St. Michaels, this exceptional waterfront retreat offers a rare combination of privacy, comfort, and quintessential Eastern Shore charm—all just minutes from the heart of town.Formerly a successful vacation rental, this beautifully

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    7149 Drum Point Rd, Saint Michaels, MD 21663
  • /3

    $435,000

    • 3 Beds
    • 2 Baths
    • 1,752 Sq Ft

    9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663

    Enjoy the charm of St. Michaels from this end-unit townhome in Martingham. Offering three bedrooms and two full baths, the home features a flexible layout with a first-floor bedroom and full bath—well suited for guests, a home office, or convenient main-level living. The renovated kitchen has white cabinetry and stone countertops, with a glass door opening to a bright, tile-floored sunroom. A

    Kaitlyn Collins Benson & Mangold, LLC

    9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663
  • /73

    $939,000

    $54K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,362 Sq Ft

    8090 Bozman Neavitt Rd, Bozman, MD 21612

    Nestled in the serene enclave of Bozman, on Harris Creek this exquisite 1940s style bungalow seamlessly blends coastal charm with modern luxury, offering an unparalleled lifestyle for discerning buyers along with fantastic sunset views and a sheltered cove. Spanning 1,362+/- square feet, this detached residence boasts three spacious bedrooms and two elegantly appointed bathrooms, each designed

    Bill Wieland Benson & Mangold, LLC

    8090 Bozman Neavitt Rd, Bozman, MD 21612
  • /65

    $655,000

    • 3 Beds
    • 2.5 Baths
    • 3,010 Sq Ft

    7963 Pond Haven Ct, Saint Michaels, MD 21663

    Charming Coastal Retreat with Endless Potential in Backcreek LandingWelcome to this beautiful two-story home in the highly sought-after Backcreek Landing neighborhood, just minutes from historic St. Michaels. Blending coastal elegance with incredible value, this property features a brand-new roof with lifetime shingles and is attractively priced, leaving you budget flexibility to update the

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    7963 Pond Haven Ct, Saint Michaels, MD 21663
  • /16

    $474,900

    Open House 10/10 Coming Soon Oct 9
    • 3 Beds
    • 2 Baths
    • 1,472 Sq Ft

    301 Lincoln Ave, Saint Michaels, MD 21663

    Coming soon in St. Michaels! **OPEN HOUSE Saturday October 3rd 11AM-1PM** This charming cottage-styled home is beautifully maintained and truly pristine inside and out. Hardwood floors, a cozy wood-burning fireplace, spacious bedrooms, updated bathrooms and a bright and airy sunroom create a home that feels warm and inviting from the moment you step inside. Outside, enjoy a large private backyard

    Crystal Smith RE/MAX Executive

    301 Lincoln Ave, Saint Michaels, MD 21663
  • /25

    $779,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,710 Sq Ft

    108 Miles, Saint Michaels, MD 21663

    A rare opportunity to pair a half-acre+ wooded in-town parcel with a thoughtfully designed single-level home concept in the heart of St. Michaels. This Concept A plan illustrates a 3-bedroom, 2-bath residence totaling approximately 1,710 square feet, featuring one-level living and an attached one-car garage. Designed to maximize functionality and flow, the concept offers flexible living spaces

    Chuck Mangold Benson & Mangold, LLC

    108 Miles, Saint Michaels, MD 21663
  • /30

    $660,000

    • 3 Beds
    • 2.5 Baths
    • 2,796 Sq Ft

    24575 Deepwater Point Dr, Saint Michaels, MD 21663

    Sprawling, 3 bedroom, 2 full bath, 1 half bath contemporary ranch home with an oversized 2-car attached garage, rear sunroom overlooking a rear patio, fish pond and gazebo. All of this on a 1.28 +/- acre parcel that backs to a pond/green of the Links at Perry Cabin Golf Course. This home has access to said golf club (membership required), scenic walking and biking trails, a nearby waterfront

    John Fifer Brokers Realty Group, LLC

    24575 Deepwater Point Dr, Saint Michaels, MD 21663
  • /63

    $1,379,800

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,332 Sq Ft

    7865 Pea Neck Rd, Saint Michaels, MD 21663

    Under construction by Laine Street Homes, this exceptional property offers over 3,300 sq ft of finished living space plus an additional 480 sq ft of covered outdoor living. Set on approximately 2 acres with mature trees and located just minutes from the heart of historic St. Michaels, the home blends privacy, luxury, and convenience.Designed with a main-level primary suite, the floor plan

    Jana Meredith Meredith Fine Properties

    7865 Pea Neck Rd, Saint Michaels, MD 21663
  • /60

    $8,495,000

    • 6 Beds
    • 11 Baths
    • 17,402 Sq Ft

    8620 Bozman Neavitt Rd, Saint Michaels, MD 21663

    NEW PRICE! Located minutes from downtown St. Michaels, “Aqua Vitae” the waters of life, sits on 8.6 private acres on Harris Creek, a Chesapeake Bay tributary. This custom-built offering w/ over 400’ of direct water frontage is comprised of 3 magnificent structures: a grand main residence, guest cottage, & “party barn” all highlighted by a waterside pool, pier w/ 4’ MLW, pine grove, putting green,

    Doc Keane Washington Fine Properties, LLC

    8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
  • /30

    $455,000

    $25K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft

    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663

    Set within the sought-after Martingham community of Quail Hollow, backing to the top rated golf course The Links at Perry Cabin, this fully updated 3-bedroom, 3-bath townhome offers stylish, low-maintenance living just minutes from downtown St. Michaels. Extensive renovations completed between 2022 and 2024 make this home truly turnkey. The main level welcomes you with beautiful wood floors, a

    Barbara Watkins Benson & Mangold, LLC

    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
  • /50

    $1,950,000

    Open Sat 1PM - 3PM $35K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,622 Sq Ft

    303 Manor St, Saint Michaels, MD 21663

    Welcome to "Mostly Porches" an exceptional coastal retreat with captivating views of the harbor, perfectly situated on a spacious .41 acre corner lot just around the corner from the shops and restaurants of St. Michaels. Built in 2018 with virtually maintenance-free construction, this beautifully designed home offers the ideal blend of comfort, style, and convenience in a rare St. Michaels

    Monica Penwell TTR Sotheby's International Realty

    303 Manor St, Saint Michaels, MD 21663
  • /50

    $2,000,000

    Open Sun 11AM - 1PM $600K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 4,492 Sq Ft

    7909 Church Neck Rd, Saint Michaels, MD 21663

    PRICE IMPROVEMENT.... PRIVATE Estate Living Minutes from Historic St. Michaels... Escape to nearly twenty acres of unspoiled countryside just moments from the charm and waterfront allure of historic St. Michaels. This 4,492-square-foot home offers refined comfort with four bedrooms, two and a half baths, and a gourmet kitchen designed for both everyday living and effortless entertaining. A

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    7909 Church Neck Rd, Saint Michaels, MD 21663
  • /25

    $999,000

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    108 Miles, Saint Michaels, MD 21663

    A rare opportunity to combine a half-acre+ wooded in-town setting with a classic Cape Cod–style home concept in the heart of St. Michaels. Concept B illustrates a two-story design featuring 3 bedrooms, 2 full baths, and 1 half bath, along with an attached two-car garage. The proposed layout offers a timeless architectural style with flexible living spaces that can be customized to suit individual

    Chuck Mangold Benson & Mangold, LLC

    108 Miles, Saint Michaels, MD 21663

Home Price Trends

Median Sale Price
$786,250
Median Single Family Sale Price
$937,500
Median Townhouse Sale Price
$435,000
Median 2 Bedroom Sale Price
$399,000
Average Price Per Sq Ft
$420
Number of Homes for Sale
28
Last 12 months Home Sales
86
Months of Supply
5.40
Median List Price
$799,475
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-1%
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