2,828

Saint Michaels, MD Homes

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  • /24

    $679,000

    $90K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,072 Sq Ft

    24555 Deepwater Point Dr, Saint Michaels, MD 21663

    This sturdy brick ranch sits on a premium lot backing up to The Links at Perry Cabin Golf Course in St. Michaels, MD. A park like setting with mature specimen trees and shrubs. It's a 4 BR, 3 full bath, one level for easy living. New updated flooring. The Martingham Subdivision provides a waterfront community lot to enjoy the Miles River constant boat shows. Wednesday night sailboat races, fourth

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    24555 Deepwater Point Dr, Saint Michaels, MD 21663
  • /16

    $1,000,000

    Sold Oct 08, 2025

    320 Perry Cabin Dr, Saint Michaels, MD 21663

    • 2 Beds
    • 2.5 Baths
    • 1,557 Sq Ft
    • Built 1988

    Last Sold Summary

    • $642/SF
    • 1 Day On Market

    Current Estimated Value $1,066,643

    Last Listing Agent Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    320 Perry Cabin Dr, Saint Michaels, MD 21663
    • /49

      Est $2,215,033

      Not Listed For Sale

      7920 Church Neck Rd, Saint Michaels, MD 21663

      • 3 Beds
      • 3.5 Baths
      • 4,825 Sq Ft
      • Built 1997
      7920 Church Neck Rd, Saint Michaels, MD 21663

      Last Sold Summary

  • /46

    $1,595,000

    Under Contract
    • 4 Beds
    • 2.5 Baths
    • 1,983 Sq Ft

    6905 Pea Neck Rd, Saint Michaels, MD 21663

    Nestled beneath a canopy of mature pines along the protected waters of Solitude Creek, this beautifully renovated waterfront retreat captures the timeless appeal of Maryland's Eastern Shore. Occupying approximately 2.745 private acres with nearly 200 feet of shoreline, the property offers an exceptional blend of privacy, boating, and relaxed luxury—just minutes from the historic waterfront town

    Eddie Mangold Benson & Mangold, LLC

    6905 Pea Neck Rd, Saint Michaels, MD 21663
  • /38

    $800,000

    Sold Nov 17, 2025

    207 Seymour Ave, Saint Michaels, MD 21663

    • 4 Beds
    • 3.5 Baths
    • 1,983 Sq Ft
    • Built 1949

    Last Sold Summary

    • $403/SF
    • 17 Days On Market

    Current Estimated Value $761,936

    Last Listing Agent Larry Brennan TTR Sotheby's International Realty

    207 Seymour Ave, Saint Michaels, MD 21663
    • /3

      Est $2,014,518

      Not Listed For Sale

      24519 New Post Rd, Saint Michaels, MD 21663

      • 4 Beds
      • 3.5 Baths
      • 2,881 Sq Ft
      • Built 2001
      24519 New Post Rd, Saint Michaels, MD 21663

      Last Sold Summary

      • 0 Days On Market

  • /28

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    101 Brooks Ln, Saint Michaels, MD 21663

    Welcome to this beautifully updated cottage in the heart of St. Michaels—where modern comfort meets Eastern Shore charm. Perfectly situated within walking distance to the town’s shops, restaurants, Rails to Trails, and the renowned Maritime Museum, this single‐level home offers both convenience and a peaceful, private setting. Sitting on nearly a quarter acre, the property features a fully fenced

    Stacie Luhrman Benson & Mangold, LLC

    101 Brooks Ln, Saint Michaels, MD 21663
  • /54

    $825,000

    Sold Oct 28, 2025

    24312 Oakwood Park Rd, Saint Michaels, MD 21663

    • 2 Beds
    • 1 Bath
    • 836 Sq Ft
    • Built 1952

    Last Sold Summary

    • $987/SF
    • 25 Days On Market

    Current Estimated Value $814,050

    Last Listing Agent Cornelia Heckenbach Long & Foster Real Estate, Inc.

    24312 Oakwood Park Rd, Saint Michaels, MD 21663
    • /70

      Est $1,699,633

      Not Listed For Sale

      7171 Drum Point Rd, Saint Michaels, MD 21663

      • 4 Beds
      • 3 Baths
      • 3,000 Sq Ft
      • Built 1969
      7171 Drum Point Rd, Saint Michaels, MD 21663

      Last Sold Summary

      • 11 Days On Market

  • /112

    $2,275,000

    $625K PRICE DROP Under Contract
    • 4 Beds
    • 4.5 Baths
    • 3,677 Sq Ft

    24645 Long Haul Rd, Saint Michaels, MD 21663

    Experience waterfront living at its finest in this remarkable St. Michaels retreat, where breathtaking water views define every moment. The beautifully remodeled main level was designed to maximize the scenery, seamlessly blending indoor comfort with the natural beauty beyond. A chef-inspired kitchen with Monogram stainless steel appliances anchors the open-concept living space, perfect for

    Donna Dickinson Coldwell Banker Realty

    24645 Long Haul Rd, Saint Michaels, MD 21663
  • /89

    $360,000

    Sold Dec 05, 2025

    9539 Quail Hollow Dr Unit 303, Saint Michaels, MD 21663

    • 2 Beds
    • 2.5 Baths
    • 1,800 Sq Ft
    • Built 1973

    Last Sold Summary

    • $200/SF
    • 52 Days On Market

    Current Estimated Value $357,631

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    9539 Quail Hollow Dr Unit 303, Saint Michaels, MD 21663
    • /35

      Est $507,057

      Not Listed For Sale

      400 Railroad Ave, Saint Michaels, MD 21663

      • 3 Beds
      • 2 Baths
      • 1,674 Sq Ft
      • Built 1930
      400 Railroad Ave, Saint Michaels, MD 21663

      Last Sold Summary

      • 62 Days On Market

  • /33

    $993,000

    • 3 Beds
    • 2 Baths
    • 1,362 Sq Ft

    8090 Bozman Neavitt Rd, Bozman, MD 21612

    Nestled in the serene enclave of Bozman, this exquisite 1940s bungalow seamlessly blends coastal charm with modern luxury, offering an unparalleled lifestyle for discerning buyers. Spanning 1,362+/- square feet, this detached residence boasts three spacious bedrooms and two elegantly appointed bathrooms, each designed with high-end finishes that elevate everyday living. The country-style kitchen

    Bill Wieland Benson & Mangold, LLC

    8090 Bozman Neavitt Rd, Bozman, MD 21612
  • /59

    $1,950,000

    Sold Jul 17, 2026

    8670 Bozman Neavitt Rd, Saint Michaels, MD 21663

    • 3 Beds
    • 3 Baths
    • 2,365 Sq Ft
    • Built 1956

    Last Sold Summary

    • 2% Below List Price
    • $825/SF
    • 10 Days On Market

    Current Estimated Value $1,356,903

    Last Listing Agent Cornelia Heckenbach Long & Foster Real Estate, Inc.

    8670 Bozman Neavitt Rd, Saint Michaels, MD 21663
    • /50

      Est $884,799

      Not Listed For Sale

      402 Railroad Ave, Saint Michaels, MD 21663

      • 3 Beds
      • 3 Baths
      • 2,450 Sq Ft
      • Built 1900
      402 Railroad Ave, Saint Michaels, MD 21663

      Last Sold Summary

  • /38

    $1,179,000

    $105K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    101 Mulberry St, Saint Michaels, MD 21663

    Beautifully restored Historic Victorian in the heart of Saint Michaels. This charming home has a strong rental history, last tenant was paying $4,500 a month. From the wide, welcoming front porch to the gated, manicured yard—complete with a hammock ideal for long afternoon naps—every space is designed for comfort and relaxation. A brick walkway leads to the custom beveled‐glass entry door and

    Jana Meredith Meredith Fine Properties

    101 Mulberry St, Saint Michaels, MD 21663
  • /13

    $99,500

    Sold Feb 20, 2026

    102 Gloria Ave, Saint Michaels, MD 21663

    • Land
    • 6,534 Sq Ft
    • $663,333 per Acre

    Last Sold Summary

    • 19 Days On Market

    Current Estimated Value $188,456

    Last Listing Agent Monica Penwell TTR Sotheby's International Realty

    102 Gloria Ave, Saint Michaels, MD 21663
    • /43

      Est $1,879,219

      Not Listed For Sale

      1015 Riverview Terrace, Saint Michaels, MD 21663

      • 5 Beds
      • 4 Baths
      • 3,301 Sq Ft
      • Built 1958
      1015 Riverview Terrace, Saint Michaels, MD 21663

      Last Sold Summary

      • 24 Days On Market

  • /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
  • /47

    $350,000

    Sold Jun 26, 2026

    24700 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663

    • 2 Beds
    • 2.5 Baths
    • 1,486 Sq Ft
    • Built 1979

    Last Sold Summary

    • 10% Below List Price
    • $236/SF
    • 132 Days On Market

    Last Listing Agent Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    24700 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663
    • /64

      Est $1,655,578

      Not Listed For Sale

      8288 Bozman Neavitt Rd, Saint Michaels, MD 21663

      • 3 Beds
      • 2.5 Baths
      • 3,282 Sq Ft
      • Built 1998
      8288 Bozman Neavitt Rd, Saint Michaels, MD 21663

      Last Sold Summary

      • 189 Days On Market

  • /119

    $1,945,000

    $50K PRICE DROP
    • 6 Beds
    • 6 Baths
    • 4,089 Sq Ft

    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663

    Check out the NEW aerial photos! An exceptional opportunity in The Homes at Perry Cabin -- a rare double residence offering approximately 4,000 square feet, six bedrooms, and six full baths in a premier Saint Michaels waterfront community. adjacent to the renowned Inn at Perry Cabin and overlooking Fogg Cove just off the Miles River. This turnkey home features expansive living areas and a

    Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
  • /2

    $1,840,000

    Sold Jul 30, 2026

    9788 Pintail Place, Saint Michaels, MD 21663

    • 4 Beds
    • 2.5 Baths
    • 2,320 Sq Ft
    • Built 1998

    Last Sold Summary

    • 3% Below List Price
    • $793/SF
    • 3 Days On Market

    Current Estimated Value $1,882,747

    Last Listing Agent Barbara Watkins Benson & Mangold, LLC

    9788 Pintail Place, Saint Michaels, MD 21663
    • /58

      Est $557,612

      Not Listed For Sale

      106 Boundary Ln, Saint Michaels, MD 21663

      • 3 Beds
      • 2 Baths
      • 1,490 Sq Ft
      • Built 1997
      106 Boundary Ln, Saint Michaels, MD 21663

      Last Sold Summary

      • 32 Days On Market

  • /61

    $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
  • /48

    $1,400,000

    Sold Nov 21, 2025

    8095 Church Neck Rd, Saint Michaels, MD 21663

    • 4 Beds
    • 2.5 Baths
    • 3,340 Sq Ft
    • Built 1991

    Last Sold Summary

    • $419/SF
    • 26 Days On Market

    Current Estimated Value $1,421,765

    Last Listing Agent Laura Carney TTR Sotheby's International Realty

    8095 Church Neck Rd, Saint Michaels, MD 21663
    • /14

      Est $93,565

      Not Listed For Sale

      313 Dodson Ave, Saint Michaels, MD 21663

      • 3 Beds
      • 1 Bath
      • 1,056 Sq Ft
      • Built 1981
      313 Dodson Ave, Saint Michaels, MD 21663

      Last Sold Summary

      • 84 Days On Market

  • /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
  • /43

    $610,000

    Sold Apr 10, 2026

    24749 Swan Rd, Saint Michaels, MD 21663

    • 3 Beds
    • 2.5 Baths
    • 2,496 Sq Ft
    • Built 1989

    Last Sold Summary

    • $244/SF
    • 264 Days On Market

    Current Estimated Value $682,442

    Last Listing Agent Steve Bealefeld Benson & Mangold, LLC

    24749 Swan Rd, Saint Michaels, MD 21663
    • /57

      Est $758,177

      Not Listed For Sale

      909 Riverview Terrace, Saint Michaels, MD 21663

      • 3 Beds
      • 2.5 Baths
      • 2,069 Sq Ft
      • Built 1956
      909 Riverview Terrace, Saint Michaels, MD 21663

      Last Sold Summary

      • 68 Days On Market

  • /10

    $309,000

    $41K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,364 Sq Ft

    203 Canton St, Saint Michaels, MD 21663

    Discover this ranch-style home located 1 block to the center of downtown, perfect for those seeking convenience to everything St Michaels has to offer. This 3-bedroom, 2-bathroom residence offers 1,364 sq. ft. of potential, set on a generous 0.17-acre lot. The rails to trails is located right at the end of the street. With a little creativity and vision, this property can be transformed into your

    Melanie Hopkins Coldwell Banker Chesapeake Real Estate Company

    203 Canton St, Saint Michaels, MD 21663
  • /36

    $926,000

    Sold Jan 15, 2026

    203 Mulberry St, Saint Michaels, MD 21663

    • 3 Beds
    • 2 Baths
    • 1,740 Sq Ft
    • Built 1970

    Last Sold Summary

    • 3% Above List Price
    • $532/SF
    • 0 Days On Market

    Current Estimated Value $909,111

    Last Listing Agent Brian Gearhart Benson & Mangold, LLC

    203 Mulberry St, Saint Michaels, MD 21663
    • /80

      Est $1,067,746

      Not Listed For Sale

      8080 Bozman Neavitt Rd, Saint Michaels, MD 21663

      • 3 Beds
      • 3 Baths
      • 5,869 Sq Ft
      • Built 1960
      8080 Bozman Neavitt Rd, Saint Michaels, MD 21663

      Last Sold Summary

      • 9 Days On Market

  • /103

    $2,349,000

    $100K PRICE DROP Under Contract
    • 4 Beds
    • 4.5 Baths
    • 3,300 Sq Ft

    962 San Domingo Ct, Saint Michaels, MD 21663

    This exquisite in-town St. Michaels coastal-style waterfront is a designer’s dream home. The 3,300 sq, ft. residence shows like a new model home with an unparalleled quality of finishes and level of design. Located in desirable San Domingo Cove, the community enjoys protected natural open space, beautiful water features and immediate access to the ever-popular St. Michaels Nature Trail offering

    Eugene Smith TTR Sotheby's International Realty

    962 San Domingo Ct, Saint Michaels, MD 21663
  • /57

    $345,000

    Sold May 29, 2026

    24354 Widgeon Place Unit 20, Saint Michaels, MD 21663

    • 2 Beds
    • 2.5 Baths
    • 1,800 Sq Ft
    • Built 1986

    Last Sold Summary

    • 1% Below List Price
    • $192/SF
    • 27 Days On Market

    Current Estimated Value $355,636

    Last Listing Agent Monica Penwell TTR Sotheby's International Realty

    24354 Widgeon Place Unit 20, Saint Michaels, MD 21663
    • /64

      Est $483,016

      Not Listed For Sale

      1110 Jefferson Ave, Saint Michaels, MD 21663

      • 4 Beds
      • 3 Baths
      • 1,600 Sq Ft
      • Built 1984
      1110 Jefferson Ave, Saint Michaels, MD 21663

      Last Sold Summary

      • 175 Days On Market

  • /2

    $3,200,000

    Pending
    • 4 Beds
    • 6 Baths
    • 3,100 Sq Ft

    703 Riverview Terrace, Saint Michaels, MD 21663

    Henry Gibbons-Neff Meredith Fine Properties

    703 Riverview Terrace, Saint Michaels, MD 21663
  • /28

    $1,175,000

    Sold Nov 14, 2025

    205 E Chew Ave, Saint Michaels, MD 21663

    • 2 Beds
    • 1.5 Baths
    • 1,780 Sq Ft
    • Built 1889

    Last Sold Summary

    • $660/SF
    • 153 Days On Market

    Current Estimated Value $1,140,376

    Last Listing Agent Brian Gearhart Benson & Mangold, LLC

    205 E Chew Ave, Saint Michaels, MD 21663
    • /70

      Est $766,084

      Not Listed For Sale

      7896 Hart Glen Ct, Saint Michaels, MD 21663

      • 4 Beds
      • 2.5 Baths
      • 3,038 Sq Ft
      • Built 2005
      7896 Hart Glen Ct, Saint Michaels, MD 21663

      Last Sold Summary

      • 14 Days On Market

  • /85

    $1,795,000

    $200K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,160 Sq Ft

    23776 Mount Pleasant Landing Cir, Saint Michaels, MD 21663

    A wonderful opportunity to purchase an amazing one story waterfront home on an expansive 2.5 acre lot with western exposure on Broad Creek. Many upgrades have been done to make this a special home to enjoy your life of relaxation and pure enjoyment on the Eastern Shore of Maryland! Mount Pleasant is a very sought after St Michaels neighborhood with close proximity to the downtown historic area of

    Leslie Stevenson Shore Living Real Estate

    23776 Mount Pleasant Landing Cir, Saint Michaels, MD 21663

Showing Results 121 - 160, Page 4 of 18

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