2,677

Homes in ZIP Code 21663

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  • /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
  • /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 $777,623

    Last Listing Agent Larry Brennan TTR Sotheby's International Realty

    207 Seymour Ave, Saint Michaels, MD 21663
    • /70

      Est $1,671,505

      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

      Last Listing Agent Larry Brennan TTR Sotheby's International Realty

  • /31

    $799,950

    • 4 Beds
    • 3.5 Baths
    • 2,154 Sq Ft

    407 Seymour Ave, Saint Michaels, MD 21663

    Enjoy the best of St. Michaels with convenient access to recreation, waterfront activities, schools and downtown. The newly renovated split-foyer home is truly move-in ready. The nicely landscaped grounds feature a fenced rear yard with mature trees, large patio and an in-ground swimming pool, creating a wonderful setting for outdoor enjoyment. Inside, the main level is filled with natural light

    Barbara Watkins Benson & Mangold, LLC

    407 Seymour Ave, 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 $841,389

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

    24312 Oakwood Park Rd, Saint Michaels, MD 21663
    • /35

      Est $509,267

      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

      Last Listing Agent Monica Penwell TTR Sotheby's International Realty

  • /38

    $1,129,000

    $155K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    101 Mulberry St, Saint Michaels, MD 21663

    Dramatic Price Drop!!! Seller ready to sell this 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

    Jana Meredith Meredith Fine Properties

    101 Mulberry St, Saint Michaels, MD 21663
  • /135

    $1,522,000

    Sold Aug 28, 2026

    216 E Chew Ave, Saint Michaels, MD 21663

    • 4 Beds
    • 3.5 Baths
    • 3,575 Sq Ft
    • Built 1997

    Last Sold Summary

    • 15% Below List Price
    • $426/SF
    • 221 Days On Market

    Current Estimated Value $1,752,258

    Last Listing Agent Christopher Clinton Coldwell Banker Chesapeake Real Estate Company

    216 E Chew Ave, Saint Michaels, MD 21663
    • /50

      Est $868,452

      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

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

  • /16

    $474,900

    Open House 10/03 Coming Soon Oct 3
    • 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
  • /22

    $2,975,000

    Sold Sep 03, 2026

    23961 Lynnewood Dr, Saint Michaels, MD 21663

    • 4 Beds
    • 3.5 Baths
    • 4,035 Sq Ft
    • Built 1994

    Last Sold Summary

    • $737/SF
    • 261 Days On Market

    Current Estimated Value $2,974,407

    Last Listing Agent Barbara Watkins Benson & Mangold, LLC

    23961 Lynnewood Dr, Saint Michaels, MD 21663
    • /43

      Est $1,821,337

      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

      Last Listing Agent Laura Carney TTR Sotheby's International Realty

  • /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
  • /88

    $1,780,000

    Sold May 28, 2026

    23857 Ebb Point Rd, Bozman, MD 21612

    • 4 Beds
    • 3.5 Baths
    • 2,250 Sq Ft
    • Built 1986

    Last Sold Summary

    • $791/SF
    • 294 Days On Market

    Current Estimated Value $1,719,292

    Last Listing Agent Tiffany Cloud Meredith Fine Properties

    23857 Ebb Point Rd, Bozman, MD 21612
    • /64

      Est $1,467,487

      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

      Last Listing Agent Debra Crouch Benson & Mangold, LLC

  • /68

    $2,395,000

    Pending
    • 4 Beds
    • 4.5 Baths
    • 4,116 Sq Ft

    965 San Domingo Ct, Saint Michaels, MD 21663

    Waterfront Living Reimagined in San Domingo Cove! Coastal influences, exceptional craftsmanship and meticulous attention to detail define this immaculate custom waterfront home. Dramatic two-story family room, soaring ceilings, walls of windows and an open staircase with stainless steel cable railings create a striking architectural statement. The second-story catwalk and loft overlook the main

    Kathy Christensen TTR Sotheby's International Realty

    965 San Domingo Ct, 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 $360,899

    Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

    9539 Quail Hollow Dr Unit 303, Saint Michaels, MD 21663
    • /63

      Est $603,695

      Not Listed For Sale

      9217 Martingham Dr, Saint Michaels, MD 21663

      • 3 Beds
      • 2.5 Baths
      • 1,945 Sq Ft
      • Built 1988
      9217 Martingham Dr, Saint Michaels, MD 21663

      Last Sold Summary

      • 3 Days On Market

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

  • /2

    $795,000

    $200K PRICE DROP Pending
    • 4 Beds
    • 3 Baths
    • 2,718 Sq Ft

    104 Cherry St, Saint Michaels, MD 21663

    AUCTION POSTPONED! Historic St. Michaels Opportunity! Priced to Sell Quickly! Property sold strictly "as-is", inspections for informational purposes only. Built circa 1860, this spacious 4-bedroom, 3-full-bath historic home offers 2,718 square feet and an exceptional in-town location just half a block from the harbor, restaurants, shops, the Chesapeake Bay Maritime Museum, and all that makes St.

    Jennifer Pogoda Redfin Corp

    104 Cherry St, Saint Michaels, MD 21663
  • /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 $1,928,179

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

    8670 Bozman Neavitt Rd, Saint Michaels, MD 21663
    • /58

      Est $545,406

      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

      Last Listing Agent Kim Crouch Ozman Benson & Mangold, LLC

  • /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
  • /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 $194,230

    Last Listing Agent Monica Penwell TTR Sotheby's International Realty

    102 Gloria Ave, Saint Michaels, MD 21663
    • /41

      Est $933,685

      Not Listed For Sale

      7841 Pea Neck Rd, Saint Michaels, MD 21663

      • 3 Beds
      • 3.5 Baths
      • 3,069 Sq Ft
      • Built 2008
      7841 Pea Neck Rd, Saint Michaels, MD 21663

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Dennis Covey Meredith Fine Properties

  • /23

    $795,000

    Open Sat 10AM - 12PM Coming Soon Sep 18
    • 4 Beds
    • 3.5 Baths
    • 2,955 Sq Ft

    7964 Pond Haven Ct, Saint Michaels, MD 21663

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    7964 Pond Haven Ct, 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
    • /14

      Est $93,087

      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

      Last Listing Agent Chuck Mangold Benson & Mangold, LLC

  • /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
  • /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
    • /57

      Est $736,958

      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

      Last Listing Agent Kathleen Coale Benson & Mangold, LLC

  • /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
  • /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 $1,429,050

    Last Listing Agent Laura Carney TTR Sotheby's International Realty

    8095 Church Neck Rd, Saint Michaels, MD 21663
    • /80

      Est $1,066,357

      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

      Last Listing Agent Mary Lapides Cummings & Co. Realtors

  • /36

    $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

    Barbara Watkins Benson & Mangold, LLC

    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
  • /3

    $877,000

    Sold Sep 08, 2026

    24896 Back Creek Dr, Saint Michaels, MD 21663

    • 5 Beds
    • 4.5 Baths
    • 3,452 Sq Ft
    • Built 2004

    Last Sold Summary

    • 3% Above List Price
    • $254/SF
    • 0 Days On Market

    Current Estimated Value $847,116

    Last Listing Agent Tiffany Cloud Meredith Fine Properties

    24896 Back Creek Dr, Saint Michaels, MD 21663
    • /64

      Est $473,414

      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

      Last Listing Agent Christie Bishop Northrop Realty

  • /41

    $249,000

    Pending
    • Land
    • 1.12 Acres
    • $222,321 per Acre

    0 Deepwater Point Dr, Saint Michaels, MD 21663

    ONE OF THE LAST LOTS IN MARTINGHAM ON DEEP WATER POINT DRIVE. LOCATED VERY CLOSE TO THE COMMUNITY WATERFRONT PARK WITH GAZEBO AND CHAIRS FOR PICKNICKS OR JUST RELAXING IN THE BREEZE WATCHING THE BOATS GO BY ; DROP YOUR KAYAK OR ENJOY THE SUNSETS, WALK OR BIKE THERE.THIS LOT IS CLEANED, HAS A BEAUTIFUL ENTRANCE , WATER METER, AND IS READY FOR YOU TO BUILT YOUR MAIN RESIDENCE OR WEEKEND GET

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    0 Deepwater Point Dr, 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 $676,075

    Last Listing Agent Steve Bealefeld Benson & Mangold, LLC

    24749 Swan Rd, Saint Michaels, MD 21663
    • /70

      Est $756,714

      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

      Last Listing Agent Kathleen Coale Benson & Mangold, LLC

  • /50

    $1,950,000

    $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

Showing Results 121 - 160, Page 4 of 18

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