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Newest Homes for Sale in Saint Michaels, MD

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  • 105 Seymour Ave, Saint Michaels, MD 21663
    105 Seymour Ave, Saint Michaels, MD 21663
    105 Seymour Ave, Saint Michaels, MD 21663
    /27

    $499,000 Open Sat 11AM - 1PM

    • 2 Beds
    • 1 Bath
    • 1,080 Sq Ft

    105 Seymour Ave, Saint Michaels, MD 21663

    St. Michaels Charmer! Welcome Home to this Cozy Cottage perfectly situated in the desirable, walkable Historic Town of St. Michaels! Full of natural light and warmth, this inviting home offers comfortable living spaces and thoughtful updates. Spacious .25 acre lot with mature trees and flower gardens. Step inside to find a welcoming living room with real hardwood floors and a wood-burning brick

    Pamela Ackermann-Doll RE/MAX Executive

    105 Seymour Ave, Saint Michaels, MD 21663
  • 108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    /6

    $779,000 New Construction

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

    108 Miles, Saint Michaels, MD 21663

    A rare opportunity in the heart of St. Michaels: this half-acre+ wooded parcel offers the privacy of a tucked-away retreat with the everyday convenience of an in-town location. Restaurants, shops, seasonal events, waterfront parks, and the character of the historic district are all close at hand, yet the setting feels quiet and natural. Approximately three times the size of a typical in-town lot,

    Chuck Mangold Benson & Mangold, LLC

    108 Miles, Saint Michaels, MD 21663
  • 108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    /6

    $999,000 New Construction

    • 3 Beds
    • 2.5 Baths

    108 Miles, Saint Michaels, MD 21663

    A rare opportunity in the heart of St. Michaels: this half-acre+ wooded parcel offers the privacy of a tucked-away retreat with the everyday convenience of an in-town location. Restaurants, shops, seasonal events, waterfront parks, and the character of the historic district are all close at hand, yet the setting feels quiet and natural. Approximately three times the size of a typical in-town lot,

    Chuck Mangold Benson & Mangold, LLC

    108 Miles, Saint Michaels, MD 21663
  • 108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    /3

    $295,000

    • Land
    • 0.55 Acre
    • $536,364 per Acre

    108 Miles, Saint Michaels, MD 21663

    A rare opportunity in the heart of St. Michaels: this half-acre+ wooded parcel offers the privacy of a tucked-away retreat with the everyday convenience of an in-town location. Restaurants, shops, seasonal events, waterfront parks, and the character of the historic district are all close at hand, yet the setting feels quiet and natural. Approximately three times the size of a typical in-town lot,

    Chuck Mangold Benson & Mangold, LLC

    108 Miles, Saint Michaels, MD 21663
  • 0 Grace St Unit MDTA2012346, Saint Michaels, MD 21663
    0 Grace St Unit MDTA2012346, Saint Michaels, MD 21663
    0 Grace St Unit MDTA2012346, Saint Michaels, MD 21663
    /10

    $265,000

    • Land
    • 0.17 Acre
    • $1,558,824 per Acre

    0 Grace St Unit MDTA2012346, Saint Michaels, MD 21663

    This is one of the loveliest lots in St. Michaels on a gorgeous residential street surrounded by charming homes. It is conveniently located in the heart of town just one block from restaurants and shopping on S Talbot Street, along with a wonderful trail and waterfront park.

    Connor LeMire Benson & Mangold, LLC

    0 Grace St Unit MDTA2012346, Saint Michaels, MD 21663
  • 23961 Lynnewood Dr, Saint Michaels, MD 21663
    23961 Lynnewood Dr, Saint Michaels, MD 21663
    23961 Lynnewood Dr, Saint Michaels, MD 21663
    /81

    $3,100,000

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

    23961 Lynnewood Dr, Saint Michaels, MD 21663

    Located within 2 miles of historic St. Michaels this exceptional waterfront estate blends timeless elegance with a resort-style setting. This 4,200± sq. ft. custom, single-level all brick residence showcases soaring ceilings, an abundance of natural light, and panoramic views of Broad Creek from almost every room. A huge great room featuring a large brick fireplace and open living / dining

    Barbara Watkins Benson & Mangold, LLC

    23961 Lynnewood Dr, Saint Michaels, MD 21663
  • 24390 Oakwood Park Rd, Saint Michaels, MD 21663
    24390 Oakwood Park Rd, Saint Michaels, MD 21663
    24390 Oakwood Park Rd, Saint Michaels, MD 21663
    /68

    $1,900,000 Open Sun 12PM - 2PM

    • 4 Beds
    • 3.5 Baths
    • 2,839 Sq Ft

    24390 Oakwood Park Rd, Saint Michaels, MD 21663

    Welcome to your private waterfront retreat just minutes from the charming, historic town of St. Michaels, Maryland. Tucked away on a quiet cul-de-sac in the serene Oakwood Park community along San Domingo Creek, this one-story residence offers four bedrooms, three and a half baths, and a harmonious blend of space and comfort. With approximately 2,839 finished square feet, all on the main level,

    Janet Larson Benson & Mangold, LLC

    24390 Oakwood Park Rd, Saint Michaels, MD 21663
  • 24912 Back Creek Dr, Saint Michaels, MD 21663
    24912 Back Creek Dr, Saint Michaels, MD 21663
    24912 Back Creek Dr, Saint Michaels, MD 21663
    /63

    $795,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 3,166 Sq Ft

    24912 Back Creek Dr, Saint Michaels, MD 21663

    Welcome to **Back Creek Landing** — one of Saint Michaels’ most desirable neighborhoods, known for its peaceful setting, friendly community, and easy access to town. Just a few minutes by bike or golf cart from downtown, this neighborhood offers the best of both worlds: close to everything, yet surrounded by nature. This beautifully maintained home invites you in with a wide front porch — perfect

    Kathleen Coale Benson & Mangold, LLC

    24912 Back Creek Dr, 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

    $1,195,000

    • 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
  • 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
  • 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
  • 9171 Deepwater Point Rd, Saint Michaels, MD 21663
    9171 Deepwater Point Rd, Saint Michaels, MD 21663
    9171 Deepwater Point Rd, Saint Michaels, MD 21663
    /40

    $1,635,000

    • 4 Beds
    • 3.5 Baths
    • 4,102 Sq Ft

    9171 Deepwater Point Rd, Saint Michaels, MD 21663

    Welcome to Saint Michaels Retreat—an extraordinary 6-acre property overlooking the Links at Perry Cabin Golf Course with direct water access to Long Haul Creek and the Miles River. Just minutes from downtown Saint Michaels, this stunningly renovated residence offers over 4,100 sq. ft. of one-level living, thoughtfully designed for effortless indoor and outdoor entertaining. Inside, expansive

    Laura Carney TTR Sotheby's International Realty

    9171 Deepwater Point Rd, 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

    $499,900

    • 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 dining

    Debra Crouch Benson & Mangold, LLC

    207 Dodson Ave, 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

    $725,000 Open Sat 10AM - 3PM

    • 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
  • 228 Tyler Ave, Saint Michaels, MD 21663
    228 Tyler Ave, Saint Michaels, MD 21663
    228 Tyler Ave, Saint Michaels, MD 21663
    /44

    $549,900 Open Sat 1PM - 3PM

    • 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
  • 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
  • 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
  • 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 Open Sat 10AM - 12PM

    • 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
  • 10770 Rich Neck Rd, Claiborne, MD 21624
    10770 Rich Neck Rd, Claiborne, MD 21624
    10770 Rich Neck Rd, Claiborne, MD 21624
    /89

    $8,475,000

    • 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
  • 704 Meadow St, Saint Michaels, MD 21663
    704 Meadow St, Saint Michaels, MD 21663
    704 Meadow St, Saint Michaels, MD 21663
    /16

    $889,800 New Construction

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

    704 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

    704 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
  • 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
Maryland Talbot County Saint Michaels

Newest Listings for Sale in Saint Michaels, MD

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 $1,154,931.
Are home prices dropping in Saint Michaels?
Yes, home prices in Saint Michaels are down 6% in the last 12 months.
How many homes have sold over the last 12 months in Saint Michaels, MD?
69 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 $799,000. If you put a 20% down payment of $159,800 and had a 30-year fixed mortgage with an interest rate of 6.24%, your estimated principal and interest payment would be $3,930 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $168K a year to afford the median home price in Saint Michaels. Learn how much home you can afford with our Home Affordability Calculator.
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 74 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 18% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$795,000
Median Single Family Sale Price
$820,000
Median Townhouse Sale Price
$415,000
Median 2 Bedroom Sale Price
$339,000
Average Price Per Sq Ft
$417
Number of Homes for Sale
18
Last 12 months Home Sales
69
Months of Supply
3.10
Median List Price
$799,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
18%
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