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Saint Michaels, MD Homes for Sale

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  • 222 E Chestnut St, Saint Michaels, MD 21663
    222 E Chestnut St, Saint Michaels, MD 21663
    222 E Chestnut St, Saint Michaels, MD 21663
    /38

    $2,250,000

    • 3 Beds
    • 2.5 Baths
    • 2,284 Sq Ft

    222 E Chestnut St, Saint Michaels, MD 21663

    A unique opportunity to own a completely renovated home in the heart of town featuring four deep-water, dedicated boat slips. Located at the end of one of the most coveted, tree-lined streets in St. Michaels, this home is surrounded by beautifully restored historic properties and offers incredible views of St. Michaels Harbor. The current owners have thoughtfully renovated this 3-bedroom,

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (844) 651-2546

    222 E Chestnut St, Saint Michaels, MD 21663
  • 408 Spinnaker Ln, Saint Michaels, MD 21663
    408 Spinnaker Ln, Saint Michaels, MD 21663
    408 Spinnaker Ln, Saint Michaels, MD 21663
    /82

    $775,000

    • 4 Beds
    • 2.5 Baths
    • 1,957 Sq Ft

    408 Spinnaker Ln, Saint Michaels, MD 21663

    This immaculate 4 bedroom, 2.5 bath home was built in 2022 and has been thoughtfully enhanced with numerous upgrades. The owners added luxury vinyl plank flooring to the second level, Hunter Douglas plantation shutters with independent top and bottom operation, recessed lighting upstairs, and a high-end full-size Electrolux washer and dryer. Additional features include a smart home system with

    Christie Bishop Northrop Realty

    408 Spinnaker Ln, Saint Michaels, MD 21663
  • 24318 Oakwood Park Rd, Saint Michaels, MD 21663
    24318 Oakwood Park Rd, Saint Michaels, MD 21663
    24318 Oakwood Park Rd, Saint Michaels, MD 21663
    /44

    $1,238,000

    • 3 Beds
    • 3 Baths
    • 1,612 Sq Ft

    24318 Oakwood Park Rd, Saint Michaels, MD 21663

    Welcome to Old House Cove Waterfront Retreat in St. Michaels, MDNestled on nearly half an acre with scenic frontage along Old House Cove, this quintessential Eastern Shore property offers a rare combination of waterfront serenity, literary history, and timeless design. The expansive parcel provides privacy in a highly desirable location, just minutes from the heart of St. Michael’s—one of

    Kathleen Eder Compass

    24318 Oakwood Park Rd, Saint Michaels, MD 21663
  • 107 E Chestnut St, Saint Michaels, MD 21663
    107 E Chestnut St, Saint Michaels, MD 21663
    107 E Chestnut St, Saint Michaels, MD 21663
    /65

    $1,195,000

    • 2 Beds
    • 2 Baths
    • 2,024 Sq Ft

    107 E Chestnut St, Saint Michaels, MD 21663

    St. Michaels charm in this Circa 1870 Certified Plaque home, although historical data reflects original construction between 1805-1820.Updates include plumbing ,wiring, New upstairs HVAC, encapsulated crawl space, kitchen ,upgraded light fixtures, motorized window shades and many architectural details, freshly painted in 2024 . Recently upgraded Primary bedroom window seats with cushions,

    Robert Fitton Meredith Fine Properties

    107 E Chestnut St, Saint Michaels, MD 21663
  • 25500 Chance Farm Rd, Royal Oak, MD 21662
    25500 Chance Farm Rd, Royal Oak, MD 21662
    25500 Chance Farm Rd, Royal Oak, MD 21662
    /43

    $2,295,000

    • 4 Beds
    • 3.5 Baths
    • 3,248 Sq Ft

    25500 Chance Farm Rd, Royal Oak, MD 21662

    Significant Price Reduction! Welcome to this exceptional waterfront retreat on 3.5 acres overlooking Solitude Creek in Royal Oak. From the moment you enter, expansive water views set the tone for gracious living. Renovated in 2023 and thoughtfully decorated by Bountiful Home in Easton, this 3,248 sq. ft. residence offers 4 bedrooms and 3.5 baths, including a main-level waterside primary suite

    Laura Carney TTR Sotheby's International Realty

    25500 Chance Farm Rd, Royal Oak, MD 21662
  • 9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
    /32

    $385,000

    • 2 Beds
    • 3 Baths
    • 1,800 Sq Ft

    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663

    Desirable Martingham Community is the location of this fabulous Quail Hollow unit nestled within the famous "links at Perry Cabin " , one of the few units with a screened porch . Enjoy the beautiful golf course views from the second floor, the first floor is private with its landscaping. Bathroom and kitchen countertops are granite, the kitchen has a space for a breakfast table, Living and

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
  • 207 Dodson Ave, Saint Michaels, MD 21663
    207 Dodson Ave, Saint Michaels, MD 21663
    207 Dodson Ave, Saint Michaels, MD 21663
    /44

    $524,900

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    207 Dodson Ave, Saint Michaels, MD 21663

    Fabulous 1910 Bungalow with welcoming front porch that has been renovated throughout. All main level living with beautiful primary suite offers room for king bed and ample closet space. Primary tiled bath offers luxury walk-in shower with sliding glass doors. Corner guest room with pocket door leading into guest bathroom. Living room has vaulted ceiling with skylight and opens to spacious

    Debra Crouch Benson & Mangold, LLC

    207 Dodson Ave, Saint Michaels, MD 21663
  • 0 Bozman Neavitt Rd Unit MDTA2011976, Saint Michaels, MD 21663
    0 Bozman Neavitt Rd Unit MDTA2011976, Saint Michaels, MD 21663
    0 Bozman Neavitt Rd Unit MDTA2011976, Saint Michaels, MD 21663
    /4

    $895,000

    • Land
    • 2.73 Acres
    • $327,839 per Acre

    0 Bozman Neavitt Rd Unit MDTA2011976, Saint Michaels, MD 21663

    Discover the perfect blend of privacy and waterfront living on this exceptional 2.73-acre wooded lot along scenic Broad Creek. With approximately 219 feet of shoreline, this property offers endless opportunities to build your dream home or weekend retreat, complete with stunning water views and direct access for boating, fishing, or kayaking. Surrounded by mature trees, the setting provides both

    Chuck Mangold Benson & Mangold, LLC

    0 Bozman Neavitt Rd Unit MDTA2011976, Saint Michaels, MD 21663
  • 228 Tyler Ave, Saint Michaels, MD 21663
    228 Tyler Ave, Saint Michaels, MD 21663
    228 Tyler Ave, Saint Michaels, MD 21663
    /44

    $565,000

    • 3 Beds
    • 2.5 Baths
    • 1,922 Sq Ft

    228 Tyler Ave, Saint Michaels, MD 21663

    This handsome home is nestled in the trees on a quiet cul de sac in Rio Vista. This popular neighborhood is five minutes from historic St. Michaels and offers public sewer and water with no town taxes. Rio Vista has a waterfront picnic area and boat slips for rent to residents for $225 per slip.This home has been very nicely maintained by the original owner. It offers one-level living, with a

    Debra Crouch Benson & Mangold, LLC

    228 Tyler Ave, Saint Michaels, MD 21663
  • 912 Calvert Ave, Saint Michaels, MD 21663
    912 Calvert Ave, Saint Michaels, MD 21663
    912 Calvert Ave, Saint Michaels, MD 21663
    /11

    $229,000

    • Land
    • 0.25 Acre
    • $916,000 per Acre

    912 Calvert Ave, Saint Michaels, MD 21663

    One of the few remaining building lots in the St. Michaels area. This is a prime building lot, 75' x 150', ready for someone to design and construct a new home. Public water/sewer and high-speed internet available for hookup. Calvert Avenue is a convenient address, near schools, banks, grocery stores, boat ramps and St. Michaels' many fine shops, museums and restaurants. A public waterfront park

    Tom Crouch Benson & Mangold, LLC

    912 Calvert Ave, Saint Michaels, MD 21663
  • 9262 Macks Ln, McDaniel, MD 21647
    9262 Macks Ln, McDaniel, MD 21647
    9262 Macks Ln, McDaniel, MD 21647
    /89

    $3,250,000

    • 4 Beds
    • 6 Baths
    • 5,400 Sq Ft

    9262 Macks Ln, McDaniel, MD 21647

    Just 4.9-miles outside historic St. Michaels, MD...Classic "Eastern Shore Waterfront Retreat," featuring a substantial 5,400+ sq. ft. home, thoughtfully designed to capture cooling SW summer breezes and spectacular sunset views across the sparkling waters of Harris Creek. Sited on 8.26 private acres w/over 300' of natural "living Shoreline," features of the brick home include high ceilings

    Tom Crouch Benson & Mangold, LLC

    9262 Macks Ln, McDaniel, MD 21647
  • 24362 Widgeon Place Unit 4, Saint Michaels, MD 21663
    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663
    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663
    /41

    $349,000

    • 2 Beds
    • 3 Baths
    • 1,800 Sq Ft

    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663

    Welcome to Martingham, a premier golf course and waterfront community located just a mile from historic St. Michaels. This Widgeon Place condo offers two en-suite bedrooms and a half bath, with a thoughtful two-level layout designed for comfort and convenience. The main level features a kitchen with a charming breakfast nook, hardwood floors, a gas fireplace, and an open-concept living area. A

    Amy Berry Meredith Fine Properties

    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663
  • 300 Perry St, Saint Michaels, MD 21663
    300 Perry St, Saint Michaels, MD 21663
    300 Perry St, Saint Michaels, MD 21663
    /10

    $149,999

    • Land
    • 0.14 Acre
    • $1,071,421 per Acre

    300 Perry St, Saint Michaels, MD 21663

    New price!...Great opportunity to own a buildable lot in one of Maryland's most charming waterfront towns. This spacious and level parcel offers the perfect canvas for your Eastern shore home. Nestled just blocks from the harbor, shops, restaurants, parks, marinas, and the Chesapeake Bay Maritime Museum. Walk to downtown restaurants and shops! The property combines small-town

    Tammy Durbin Long & Foster Real Estate, Inc.

    300 Perry St, Saint Michaels, MD 21663
  • 24420 Mallard Place, Saint Michaels, MD 21663
    24420 Mallard Place, Saint Michaels, MD 21663
    24420 Mallard Place, Saint Michaels, MD 21663
    /33

    $825,000

    • 4 Beds
    • 2.5 Baths
    • 2,493 Sq Ft

    24420 Mallard Place, Saint Michaels, MD 21663

    This stately and well-constructed brick/wood cape cod majestically sits on a prime corner lot in the extremely desirable community of Martingham. The ideal floor-plan features a main floor primary bedroom and 3 second floor guest bedrooms. Beautiful hardwood flooring, custom built-ins, fireplace, 2 story foyer, screened porch , deck, covered front porch, circular driveway with extra parking

    Robert Lacaze TTR Sotheby's International Realty

    24420 Mallard Place, Saint Michaels, MD 21663
  • 10770 Rich Neck Rd, Claiborne, MD 21624
    10770 Rich Neck Rd, Claiborne, MD 21624
    10770 Rich Neck Rd, Claiborne, MD 21624
    /89

    $8,875,000

    • 7 Beds
    • 7.5 Baths
    • 10,240 Sq Ft

    10770 Rich Neck Rd, Claiborne, MD 21624

    Incredible 300+ acre landmark estate located 5 miles beyond St. Michaels. Over FOUR MILES OF SHORELINE on Eastern Bay, the Miles River and Tilghman Creek. Deep protected anchorage. High land. Sandy beaches. Very livable 10,000+ sq ft home that underwent two-year renovation 2005/2006. 13 ft ceilings on first story and almost10 ft on second story. Formal and informal living areas. Chef's kitchen

    Robert G. Shannahan Shoreline Realty

    10770 Rich Neck Rd, Claiborne, MD 21624
  • 24749 Swan Rd, Saint Michaels, MD 21663
    24749 Swan Rd, Saint Michaels, MD 21663
    24749 Swan Rd, Saint Michaels, MD 21663
    /43

    $650,000

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

    24749 Swan Rd, Saint Michaels, MD 21663

    Located in Martingham, home of the newly redesigned Pete Dye golf course, The Links at Perry Cabin. This 3BR/2.5BA Colonial style home is situated on an open 1.13ac lot with a tree lined backyard for privacy. Inside you will enjoy a spacious floor plan, and updated island kitchen, and a large family room highlighted by a wood burning fireplace and a beam ceiling. Upstairs you will find the

    Steve Bealefeld Benson & Mangold, LLC

    24749 Swan Rd, Saint Michaels, MD 21663
  • 8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
    8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
    8620 Bozman Neavitt 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
  • 00 New Rd, McDaniel, MD 21647
    00 New Rd, McDaniel, MD 21647
    00 New Rd, McDaniel, MD 21647
    /9

    $200,000

    • Land
    • 8.03 Acres
    • $24,907 per Acre

    00 New Rd, McDaniel, MD 21647

    8.037 Acres located just west of St. Michaels, MD. All wooded and has been used primarily for hunting and fire wood. There is one and possibly two approved perc sites though they may need to be updated. Access off of New Road and Walkers Turn road, there may be an opportunity to subdivide but would need to be discussed with County Planning and Zoning. Opportunity to build your home with a lot of

    James Bent Benson & Mangold, LLC

    00 New Rd, McDaniel, MD 21647
  • 807 Radcliff Ave, Saint Michaels, MD 21663
    807 Radcliff Ave, Saint Michaels, MD 21663
    807 Radcliff Ave, Saint Michaels, MD 21663
    /33

    $859,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,027 Sq Ft

    807 Radcliff Ave, Saint Michaels, MD 21663

    Home is currently under construction with an estimated completion date of Feb-March 2026. Photos are of a similar home with comparable finishes by the same builder. This 3BR, 2.5BA Arts & Crafts home sits on a quaint lot in beautiful Saint Michaels and will be clad with high end finishes throughout. The luxurious kitchen will feature stylish pistachio and linen shaker cabinetry with satin bronze

    Adam Ellison Long & Foster Real Estate, Inc.

    807 Radcliff Ave, Saint Michaels, MD 21663
  • 216 Brooks Ln, Saint Michaels, MD 21663
    216 Brooks Ln, Saint Michaels, MD 21663
    216 Brooks Ln, Saint Michaels, MD 21663
    /37

    $479,999 New Construction

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    216 Brooks Ln, Saint Michaels, MD 21663

    Welcome to your future home in the heart of St. Michaels! Currently under construction, this brand-new rancher will showcase modern design and quality craftsmanship throughout. Featuring 3 spacious bedrooms and 2 full bathrooms, this single-level home is designed for comfort and convenience.Step inside to find beautiful LVP flooring, a large trim package, and a bright open layout. The

    Chance Stem LPT Realty, LLC

    216 Brooks Ln, Saint Michaels, MD 21663
  • Lot 2 Meadow St, Saint Michaels, MD 21663
    Lot 2 Meadow St, Saint Michaels, MD 21663
    Lot 2 Meadow St, Saint Michaels, MD 21663
    /16

    $889,800 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,100 Sq Ft

    Lot 2 Meadow St, Saint Michaels, MD 21663

    Welcome to Saint Michaels. Located near the historic district, close to the harbor and 2 waterfront parks,and the numerous quaint shops and eating establishments as well as the museums. Lacrosse homes is proud to present The Midshore. This 4 bedroom 4.5 bath home with open floor plan is designed for everyday enjoyment or the perfect second home. Every bedroom has its own private bathroom. The

    George Bailey Keller Williams Flagship

    Lot 2 Meadow St, Saint Michaels, MD 21663
  • Lot 16A Meadow St, Saint Michaels, MD 21163
    Lot 16A Meadow St, Saint Michaels, MD 21163
    Lot 16A Meadow St, Saint Michaels, MD 21163
    /24

    $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 staement.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
Maryland Talbot County Saint Michaels

Real Estate & Homes for Sale in Saint Michaels, MD

Why Live in Saint Michaels

Saint Michaels retains much of its historic charm from its origins as a 17th-century Eastern Shore seaport and still draws visitors from around the region to its landmarks and cruises on Miles River. Buyers can search for historic homes that are ...

Learn more about living in Saint Michaels

Frequently Asked Questions

What is the average home price in Saint Michaels, MD?
Homes for sale in Saint Michaels, MD have an average home price of $1,194,499.
How many homes have sold over the last 12 months in Saint Michaels, MD?
71 homes have sold in Saint Michaels, MD over the last 12 months.
What are the most popular zip codes in Saint Michaels, MD?
The most popular zip codes in Saint Michaels, MD include 21663, 21662, 21612, 21647 and 21601.
How much do you need to make to afford a house in Saint Michaels?
The median home price in Saint Michaels is $799,500. If you put a 20% down payment of $159,900 and had a 30-year fixed mortgage with an interest rate of 6.17%, your estimated principal and interest payment would be $3,900 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $167K a year to afford the median home price in Saint Michaels.
How are the schools in Saint Michaels, MD?
Saint Michaels, MD has highly rated public and private schools. Some of the best schools in Saint Michaels based on Niche Grades are Easton High School, St. Michaels Middle/High School and St. Michaels Elementary School. Browse all the schools in Saint Michaels, MD to learn more.

Home Trends in Saint Michaels, MD

On average, homes in Saint Michaels, MD sell after 62 days on the market compared to the national average of 53 days. The median sale price for homes in Saint Michaels, MD over the last 12 months is $795,000, up 19% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$795,000
Median Single Family Sale Price
$825,000
Median Townhouse Sale Price
$435,000
Median 2 Bedroom Sale Price
$365,000
Average Price Per Sq Ft
$422
Number of Homes for Sale
15
Last 12 months Home Sales
71
Months of Supply
2.50
Median List Price
$799,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
19%
How to Buy a Home How to Finance a Home How to Sell a Home

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