94

Homes for Sale near St. Michaels Middle/High School

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  • 100 Grace St, St. Michaels, MD 21663
    100 Grace St, St. Michaels, MD 21663
    100 Grace St, St. Michaels, MD 21663
    /46

    $1,099,000

    • 2 Beds
    • 2.5 Baths
    • 1,445 Sq Ft

    100 Grace St, St. Michaels, MD 21663

    Located in the heart of St. Michaels' historic district, this adorable cottage has a rare zoning that allows for short term vacation rental, and it has been a very successful one. The current owner has great reviews and reports revenues of $65,000 in 2025. There is excellent bedroom separation, with one bedroom on the first floor in the back, the other on the second floor in the front. The

    Debra Crouch Benson & Mangold, LLC

    100 Grace St, St. Michaels, MD 21663
  • 5559 Trafalgar Cir, Tilghman, MD 21671
    5559 Trafalgar Cir, Tilghman, MD 21671
    5559 Trafalgar Cir, Tilghman, MD 21671
    /62

    $575,000

    • 5 Beds
    • 3.5 Baths
    • 3,404 Sq Ft

    5559 Trafalgar Cir, Tilghman, MD 21671

    Welcome to this beautiful, spacious 5-bedroom, 3 1/2-bathroom single-family home located in the sought-after Tilghman on Chesapeake community. This property offers the perfect blend of modern comfort and serene island living, featuring an open-concept floor plan with plenty of natural light and elegant finishes. Each bedroom offers ample space and comfort with the Primary Suite offering 2

    Becky Wibberley Coldwell Banker Realty

    5559 Trafalgar Cir, Tilghman, MD 21671
  • 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
  • 25832 Turner Ave, Royal Oak, MD 21662
    25832 Turner Ave, Royal Oak, MD 21662
    25832 Turner Ave, Royal Oak, MD 21662
    /6

    $859,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,200 Sq Ft

    25832 Turner Ave, Royal Oak, MD 21662

    Centrally located between Easton and St Michaels and just a stone’s throw from the Oxford Bellevue Ferry on the Tred Avon, one of Talbot County’s premier waterfront communities with 13 half acre to 1.5 acre home sites. The community features its own private beach and kayak launch with nearby public park with playground and marina. Just minutes to Talbot County's favorite waterfront towns by car,

    Chuck Mangold Benson & Mangold, LLC

    25832 Turner Ave, Royal Oak, MD 21662
  • 5520 Leeward Ln, Tilghman, MD 21671
    5520 Leeward Ln, Tilghman, MD 21671
    5520 Leeward Ln, Tilghman, MD 21671
    /83

    $1,200,000

    • 5 Beds
    • 2.5 Baths
    • 4,214 Sq Ft

    5520 Leeward Ln, Tilghman, MD 21671

    Welcome to 5520 Leeward Lane, a private waterfront estate tucked away at the end of a quiet, tree-lined drive on Tilghman Island—a rare opportunity to own a stunning piece of Maryland’s Eastern Shore. This expansive home features panoramic water views from almost every room and delivers the ultimate blend of luxury, comfort, and natural beauty. The grand foyer sets a graceful tone, leading into a

    Samantha Jackson Keller Williams Realty

    5520 Leeward Ln, Tilghman, MD 21671
  • 6050 Sunset Ln, Tilghman, MD 21671
    6050 Sunset Ln, Tilghman, MD 21671
    6050 Sunset Ln, Tilghman, MD 21671
    /74

    $1,250,000

    • 3 Beds
    • 3 Baths
    • 3,232 Sq Ft

    6050 Sunset Ln, Tilghman, MD 21671

    Exquisitely designed renovation incorporating high end finishes makes this waterfront 3BR, 3B cottage the perfect retreat! Large great room w/dining area, fireplace & multiple seating areas gives you ample spaces to enjoy the broad, westerly views of the bay. The gourmet kitchen & pantry is a chef's dream. Screen room, private pier, separate garage w/ guest house.

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    6050 Sunset Ln, Tilghman, MD 21671
  • 27772 Sharp Rd, Easton, MD 21601
    27772 Sharp Rd, Easton, MD 21601
    27772 Sharp Rd, Easton, MD 21601
    /85

    $13,750,000

    • 5 Beds
    • 9 Baths
    • 13,228 Sq Ft

    27772 Sharp Rd, Easton, MD 21601

    Stock Range Farm spans 350 acres of prime waterfront and is available for purchase in its entirety OR with reduced acreage including the main residence, if the buyer so chooses. Options include selling main residence with 20+ acres, 40+ acres, and 100+ acres. **CALL listing agent for more information!The property is free of easements and includes development rights, subject to all applicable

    Laura Carney TTR Sotheby's International Realty

    27772 Sharp Rd, Easton, MD 21601
  • 9262 Macks Ln, McDaniel, MD 21647
    9262 Macks Ln, McDaniel, MD 21647
    9262 Macks Ln, McDaniel, MD 21647
    /89

    $2,998,000

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

    9262 Macks Ln, McDaniel, MD 21647

    Just 5-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
  • 11470 Wye Heights Rd, Easton, MD 21601
    11470 Wye Heights Rd, Easton, MD 21601
    11470 Wye Heights Rd, Easton, MD 21601
    /55

    $3,495,000

    • 8 Beds
    • 9 Baths
    • 10,533 Sq Ft

    11470 Wye Heights Rd, Easton, MD 21601

    Nestled on a sprawling 42-acre estate adjacent to the historic Wye Heights Plantation, this stately 8-bedroom mansion offers an unparalleled blend of elegance, comfort, and tranquility. The grand interior is marked by soaring ceilings and meticulous detailing, with an elevator providing convenient access across multiple levels. The heart of the home is designed for both relaxation and

    Chuck Mangold Benson & Mangold, LLC

    11470 Wye Heights Rd, Easton, MD 21601
  • 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 Open Sun 12PM - 2PM

    • 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
  • 23857 Ebb Point Rd, Bozman, MD 21612
    23857 Ebb Point Rd, Bozman, MD 21612
    23857 Ebb Point Rd, Bozman, MD 21612
    /93

    $1,995,000

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

    23857 Ebb Point Rd, Bozman, MD 21612

    *Furniture and decor included in sale*Experience elevated coastal living in this impeccably renovated 2,250 sq ft post-and-beam home, reimagined as a coastal modern contemporary masterpiece by interior designer Hollace Kutay. Known as Oyster Cove for its picturesque 2.5 acre location on Broad Creek, this home is perfectly situated for boaters and kayakers seeking both adventure and

    Hollace Kutay Meredith Fine Properties

    23857 Ebb Point Rd, Bozman, MD 21612
  • 26546 Presquile Dr N, Easton, MD 21601
    26546 Presquile Dr N, Easton, MD 21601
    26546 Presquile Dr N, Easton, MD 21601
    /138

    $8,400,000

    • 7 Beds
    • 8 Baths
    • 8,001 Sq Ft

    26546 Presquile Dr N, Easton, MD 21601

    Presquile Manor House, originally built by the Lloyd Family circa 1800 as one of their three Plantation Houses, sits up high on the Wye River with due West Exposure. The Main House has recently gone through a two-year renovation process from top to bottom by West & Callahan Construction and Peter Zimmerman Architects Inc, with much thought and care to keep all of the historic attributes that

    Henry Gibbons-Neff Meredith Fine Properties

    26546 Presquile Dr N, Easton, MD 21601
  • 25831 Turner Ave, Royal Oak, MD 21662
    25831 Turner Ave, Royal Oak, MD 21662
    25831 Turner Ave, Royal Oak, MD 21662
    /7

    $799,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,200 Sq Ft

    25831 Turner Ave, Royal Oak, MD 21662

    Designed to optimize water views of the Tred Avon and access to the community kayak launch and beach area is this to be built home. features an open floor plan with luxury vinyl plank on the main level. Kitchen features an island, granite countertops and GE Profile appliance. The exterior features Hardie plank siding, Andersen Windows and a covered porch. Centrally located between Easton and St

    Chuck Mangold Benson & Mangold, LLC

    25831 Turner Ave, Royal Oak, MD 21662
  • 25833 Turner Ave, Royal Oak, MD 21662
    25833 Turner Ave, Royal Oak, MD 21662
    25833 Turner Ave, Royal Oak, MD 21662
    /8

    $865,500 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,200 Sq Ft

    25833 Turner Ave, Royal Oak, MD 21662

    Centrally located between Easton and St Michaels and just a stone’s throw from the Oxford Bellevue Ferry on the Tred Avon, one of Talbot County’s premier waterfront communities with 13 half acre to 1.5 acre home sites. The community features its own private beach and kayak launch with nearby public park with playground and marina. Just minutes to Talbot County's favorite waterfront towns by car,

    Chuck Mangold Benson & Mangold, LLC

    25833 Turner Ave, Royal Oak, MD 21662
  • 21485 Island Club Rd, Tilghman, MD 21671
    21485 Island Club Rd, Tilghman, MD 21671
    21485 Island Club Rd, Tilghman, MD 21671
    /83

    $2,499,000

    • 5 Beds
    • 4.5 Baths
    • 4,303 Sq Ft

    21485 Island Club Rd, Tilghman, MD 21671

    Discover the essence of refined Eastern Shore living in this meticulously renovated contemporary waterfront retreat, gracefully set along the tranquil shores of Harris Creek and looking out to the Choptank River. Every detail of this remarkable home exemplifies elegance. Step inside to a breathtaking panorama of water views framed by expansive windows that fill the home with ethereal lighting.

    Alicia Gannon Dulin Benson & Mangold, LLC

    21485 Island Club Rd, Tilghman, MD 21671
  • 25835 Turner Ave, Royal Oak, MD 21662
    25835 Turner Ave, Royal Oak, MD 21662
    25835 Turner Ave, Royal Oak, MD 21662
    /7

    $942,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,200 Sq Ft

    25835 Turner Ave, Royal Oak, MD 21662

    Designed to optimize water views of the Tred Avon and access to the community kayak launch and beach area is this to be built home. features an open floor plan with luxury vinyl plank on the main level. Kitchen features an island, granite countertops and GE Profile appliance. The exterior features Hardie plank siding, Andersen Windows and a covered porch. Centrally located between Easton and St

    Chuck Mangold Benson & Mangold, LLC

    25835 Turner Ave, Royal Oak, MD 21662
  • 4957 Bar Neck Rd, Tilghman, MD 21671
    4957 Bar Neck Rd, Tilghman, MD 21671
    4957 Bar Neck Rd, Tilghman, MD 21671
    /45

    $699,900

    • 3 Beds
    • 3 Baths
    • 2,660 Sq Ft

    4957 Bar Neck Rd, Tilghman, MD 21671

    Secure and Secluded Luxury Living with Bay Views & Resort-Style BackyardProperty is located in FEMA Zone X, has never had water on the property and seller is not required to have flood insuranceTucked away at the end of a private Crepe Myrtle-lined drive, this well-maintained luxury retreat offers the perfect blend of tranquility, style, and function—without the constraints of an HOA.

    Danny Martin Keller Williams Flagship

    4957 Bar Neck Rd, Tilghman, MD 21671
  • 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

    • 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
  • 7651 Main St, Sherwood, MD 21665
    7651 Main St, Sherwood, MD 21665
    7651 Main St, Sherwood, MD 21665
    /35

    $425,000

    • 2 Beds
    • 2 Baths
    • 1,776 Sq Ft

    7651 Main St, Sherwood, MD 21665

    CHARMING SHERWOOD VILLAGE WITH ITS RICH HISTORY. ONE OF THE BEST KEPT SECRETS.STEP BACK IN TIME, WONDER PAST BEAUTIFUL GARDENS UNDER SHADE TREES, GET GREETED BY THE PEACEFUL SETTING . THE COMMUNITY DOCK WITH MULTIPLE SLIPS AND FLOATING DOCK , THE KAYAK LANDING, IS A NEIGHBORHOOD HANG OUT, VERY POPULAR AT SUNSET TIME TO ENJOY GLORIOUS SUNSETS WITH WIDE OPEN VIEWS OVER HARRIS

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    7651 Main St, Sherwood, MD 21665
  • 5837 Irish Creek Rd, Royal Oak, MD 21662
    5837 Irish Creek Rd, Royal Oak, MD 21662
    5837 Irish Creek Rd, Royal Oak, MD 21662
    /70

    $3,095,000

    • 4 Beds
    • 3.5 Baths
    • 3,088 Sq Ft

    5837 Irish Creek Rd, Royal Oak, MD 21662

    Absolutely stunning mid-century contemporary estate offering a private , park-like setting, with heated swimming pool, pavilion, luxurious fully equipped outdoor- kitchen, outdoor shower, in -ground hot tub ,tennis court, and maintenance -free Azek pier with new 30K lb. boat lift. Meticulously maintained inside and out! Professionally landscaped with WiFi controlled front/rear irrigation

    Robert Lacaze TTR Sotheby's International Realty

    5837 Irish Creek Rd, Royal Oak, MD 21662
  • 26698 Arcadia Shores Rd, Easton, MD 21601
    26698 Arcadia Shores Rd, Easton, MD 21601
    26698 Arcadia Shores Rd, Easton, MD 21601
    /71

    $700,000

    • 5 Beds
    • 3.5 Baths
    • 2,306 Sq Ft

    26698 Arcadia Shores Rd, Easton, MD 21601

    Charming 5-Bedroom Cape Cod on 4 Private Acres with Pool, Sunroom & Endless Outdoor BeautyWelcome to your dream retreat! Tucked away on 4 private, park-like acres, this beautifully maintained 5-bedroom, 3.5-bath Cape Cod blends timeless charm with thoughtful modern updates. Relax or entertain with ease—whether you're enjoying summer afternoons by the in-ground pool (with a 20-year liner, only

    Becky Wibberley Coldwell Banker Realty

    26698 Arcadia Shores Rd, Easton, MD 21601
  • 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
  • 24749 Swan Rd, Saint Michaels, MD 21663
    24749 Swan Rd, Saint Michaels, MD 21663
    24749 Swan Rd, Saint Michaels, MD 21663
    /43

    $630,000

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

    24749 Swan Rd, Saint Michaels, MD 21663

    Special Year-End Incentive! Seller is offering a Buyer Credit at settlement toward closing costs or repairs with a ratified contract by 12/31/25.This is a rare chance to secure meaningful savings and a beautiful home in one of the Eastern Shore’s most desirable communities.Welcome to Martingham—home to the newly redesigned Pete Dye course, The Links at Perry Cabin, and just minutes from

    Steve Bealefeld Benson & Mangold, LLC

    24749 Swan Rd, Saint Michaels, MD 21663
  • 22349 Cooper Ln, Wittman, MD 21676
    22349 Cooper Ln, Wittman, MD 21676
    22349 Cooper Ln, Wittman, MD 21676
    /22

    $245,000

    • 2 Beds
    • 1 Bath
    • 1,270 Sq Ft

    22349 Cooper Ln, Wittman, MD 21676

    Charming farmhouse with approximately 1300 sq feet of living space on a large, picturesque lot. Perfect weekend retreat close to St. Michaels, investment property or full time residence. The second level has two bedrooms, walk-in closet, a cozy nook ideal for a home office and a recently fully renovated bathroom. First floor includes a front room suited for an office or additional full bathroom.

    Brian Petzold Benson & Mangold, LLC

    22349 Cooper Ln, Wittman, MD 21676
  • 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
  • 5489 Rude Ave, Tilghman, MD 21671
    5489 Rude Ave, Tilghman, MD 21671
    5489 Rude Ave, Tilghman, MD 21671
    /65

    $850,000

    • 4 Beds
    • 2.5 Baths
    • 2,286 Sq Ft

    5489 Rude Ave, Tilghman, MD 21671

    Spacious 3,000 sqft two-story waterfront home on 3/4 acre parcel on Harris Creek where it joins the Choptank River for an 11-mile view to Cambridge. House is brick and block on the first level with redwood siding on the second level in board and batten style. 150ft heavily built and reinforced bulkhead waterfront with recently renovated 75ft long dock. Second floor includes four bedrooms with

    Leo Kuneman Meredith Fine Properties

    5489 Rude Ave, Tilghman, MD 21671
  • 8014 Easton Village Dr, Easton, MD 21601
    8014 Easton Village Dr, Easton, MD 21601
    8014 Easton Village Dr, Easton, MD 21601
    /28

    $674,000

    • 3 Beds
    • 2.5 Baths
    • 1,861 Sq Ft

    8014 Easton Village Dr, Easton, MD 21601

    Rarely available offering in Easton Village, one of Easton's finest waterfront communities...and under $700,000! This fine home features lower and upper-level open front porches, side deck, rear entry 2-car garage with a concrete driveway, and a poured-concrete crawl space. Kitchen features stainless steel appliances, generous cabinet space and granite countertops. Gas fireplace and vaulted

    John Fifer Brokers Realty Group, LLC

    8014 Easton Village Dr, Easton, MD 21601
  • 25826 Orchard Terrace, Royal Oak, MD 21662
    25826 Orchard Terrace, Royal Oak, MD 21662
    25826 Orchard Terrace, Royal Oak, MD 21662
    /3

    $950,000

    • Land
    • 1.6 Acres
    • $593,750 per Acre

    25826 Orchard Terrace, Royal Oak, MD 21662

    Buildable 1.6 +/- acre lot ready for your vision and a builder ready to help you make it a reality! Over 500 ft of shoreline on the Tred Avon River. Close to the public park/playground and just a short boat ride or ferry ride to Oxford. Centrally located between Easton and St Michaels. Just minutes to Talbot County's favorite waterfront towns by car, bike, or boat.

    Chuck Mangold Benson & Mangold, LLC

    25826 Orchard Terrace, Royal Oak, MD 21662
  • 8034 Bozman Neavitt Rd, Bozman, MD 21612
    8034 Bozman Neavitt Rd, Bozman, MD 21612
    8034 Bozman Neavitt Rd, Bozman, MD 21612
    /22

    $179,900

    • 2 Beds
    • 1 Bath
    • 1,160 Sq Ft

    8034 Bozman Neavitt Rd, Bozman, MD 21612

    Great opportunity to buy below market value. House needs work, but opportunity is endless. Sold strictly AS IS. Seller and listing agent do not guarantee accuracy in this listing. Buyer must do their own due diligence before submitting an offer. Cash or Hard Money only. Seller prefers New World Title Company.

    Alex Fox Allfirst Realty, Inc.

    8034 Bozman Neavitt Rd, Bozman, MD 21612
  • 27240 Hayward Trail, Easton, MD 21601
    27240 Hayward Trail, Easton, MD 21601
    27240 Hayward Trail, Easton, MD 21601
    /37

    $515,000

    • 3 Beds
    • 2 Baths
    • 1,704 Sq Ft

    27240 Hayward Trail, Easton, MD 21601

    Exceptionally well-maintained rancher located on a quiet residential street (Hayward Trail) in the Doncaster community between Easton and St. Michaels. The 3-bedroom, 2-bath home features a spacious dining/family room addition w/fireplace and cathedral ceiling. A breezeway connects the house to a 2-car garage. The back yard is special, with a beautiful swimming pool and covered Tiki Bar/sitting

    Tom Crouch Benson & Mangold, LLC

    27240 Hayward Trail, Easton, MD 21601
  • 8781 Tilghman Island Rd, Wittman, MD 21676
    8781 Tilghman Island Rd, Wittman, MD 21676
    8781 Tilghman Island Rd, Wittman, MD 21676
    /60

    $3,795,000

    • 5 Beds
    • 5.5 Baths
    • 6,487 Sq Ft

    8781 Tilghman Island Rd, Wittman, MD 21676

    A magnificent, stately, Daffin-built, Chesapeake Bay Brick Estate exudes excellent design and craftsmanship in this 5 bedroom (suites) , 5.5 bath 6,500 sq. ft brick home that majestically sits on 21.7 acres facing the Chesapeake Bay. Excellent construction quality and design are evident throughout this magnificent estate. Geothermal system on 1st and 2nd floors; Heat Pump for the 3rd floor;

    Robert Lacaze TTR Sotheby's International Realty

    8781 Tilghman Island Rd, Wittman, MD 21676
  • 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
  • 21477 Island Club Rd, Tilghman, MD 21671
    21477 Island Club Rd, Tilghman, MD 21671
    21477 Island Club Rd, Tilghman, MD 21671
    /50

    $1,200,000

    • 4 Beds
    • 2.5 Baths
    • 3,040 Sq Ft

    21477 Island Club Rd, Tilghman, MD 21671

    Welcome to waterfront living at its finest on picturesque Tilghman Island! This beautifully maintained 3,040 sq ft Colonial offers stunning open water views and a lifestyle of comfort, elegance, and ease. Boasting four spacious bedrooms and two and a half baths, this home features a flowing floor plan with natural light, generous living spaces, and a perfect blend of indoor and outdoor

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    21477 Island Club Rd, Tilghman, MD 21671
  • 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

    Fabulous St. Michaels location near Miles River, St. Michaels Marina, Inn & Spa, St, Michael’s Winery, area schools and so much more! Enjoy all the benefits of a coastal lifestyle in this charming & scenic historic town. Build your dream home on a attractive homesite minutes from everything and everywhere you want to be.The Pointe offers an impressive open kitchen with island, pantry and

    George Bailey Keller Williams Flagship

    704 Meadow St, Saint Michaels, MD 21663
  • 0 Lot 16 N Unit MDTA2012070, Easton, MD 21601
    0 Lot 16 N Unit MDTA2012070, Easton, MD 21601
    0 Lot 16 N Unit MDTA2012070, Easton, MD 21601
    /44

    $780,000

    • 3 Beds
    • 2.5 Baths
    • 2,065 Sq Ft

    0 Lot 16 N Unit MDTA2012070, Easton, MD 21601

    Discover the charm of historic Easton in this thoughtfully designed new construction home, perfectly situated within walking distance to the heart of town. This custom-built residence blends modern living with timeless appeal, featuring a desirable main-level primary bedroom, spacious two-car garage, inviting backyard, and the opportunity to personalize finishes to your taste. Enjoy the

    Jana Meredith Meredith Fine Properties

    0 Lot 16 N Unit MDTA2012070, Easton, MD 21601
  • 21486 Mission Rd, Tilghman, MD 21671
    21486 Mission Rd, Tilghman, MD 21671
    21486 Mission Rd, Tilghman, MD 21671
    /32

    $549,000

    • 9 Beds
    • 2.5 Baths
    • 5,389 Sq Ft

    21486 Mission Rd, Tilghman, MD 21671

    This historic property known as "The Elms" was built in 1900 and used as a fishing lodge for many years. The property sits on 2 acres, has public sewer and well water. The buildings hold virtually no value unless and extensive historic renovation were completed. Tilghman is an historic waterfront town that features a waterman's museum, marina, many restaurants, established

    Monica Penwell TTR Sotheby's International Realty

    21486 Mission Rd, Tilghman, MD 21671
  • 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
  • 228 Tyler Ave, Saint Michaels, MD 21663
    228 Tyler Ave, Saint Michaels, MD 21663
    228 Tyler Ave, Saint Michaels, MD 21663
    /44

    $549,900

    • 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
  • 9681 Macks Ln, McDaniel, MD 21647
    9681 Macks Ln, McDaniel, MD 21647
    9681 Macks Ln, McDaniel, MD 21647
    /3

    $92,000

    • 2 Beds
    • 1 Bath
    • 920 Sq Ft

    9681 Macks Ln, McDaniel, MD 21647

    Price Improvement!!! Please don’t enter the home. The value is in the land.

    Lesley Jackson EXIT Sunshine Realty

    9681 Macks Ln, McDaniel, MD 21647

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