107

Homes for Sale near St. Michaels Middle/High School

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  • 21732 Cabin Ln, Sherwood, MD 21665
    21732 Cabin Ln, Sherwood, MD 21665
    21732 Cabin Ln, Sherwood, MD 21665
    /5

    $25,000

    • Land
    • 0.13 Acre
    • $192,308 per Acre

    21732 Cabin Ln, Sherwood, MD 21665

    .2 +/- acres located off of Cabin Ln in Sherwood, Md. Located 10 minutes from St. Michaels, MD and 5 minutes from Tilghman, MD.BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

    Shawn Moore Meredith Fine Properties

    21732 Cabin Ln, Sherwood, MD 21665
  • 21748 Cabin Ln, Sherwood, MD 21665
    21748 Cabin Ln, Sherwood, MD 21665
    21748 Cabin Ln, Sherwood, MD 21665
    /5

    $25,000

    • Land
    • 0.80 Acre
    • $31,250 per Acre

    21748 Cabin Ln, Sherwood, MD 21665

    .8 +/- acres located off of Punch Point Rd. Approximately 2.5 miles from Tilghman, Md.BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

    Shawn Moore Meredith Fine Properties

    21748 Cabin Ln, Sherwood, MD 21665
  • 216 E Chew Ave, Saint Michaels, MD 21663
    216 E Chew Ave, Saint Michaels, MD 21663
    216 E Chew Ave, Saint Michaels, MD 21663
    /56

    $1,899,000

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

    216 E Chew Ave, Saint Michaels, MD 21663

    Experience and enjoy captivating views of the St Michaels Harbor from every room in the house. Conveniently situated in the heart of downtown St Michaels within walking distance to casual and fine dining. The floorplan includes 4 bedrooms, 3 full baths and 1 half bath. Total bedroom and bath count includes a separate guest suite with full kitchen. The newer addition is an octagon great room with

    Daphne Cawley TTR Sotheby's International Realty

    216 E Chew Ave, Saint Michaels, MD 21663
  • 24560 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663
    24560 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663
    24560 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663
    /48

    $369,000

    • 2 Beds
    • 2 Baths
    • 1,296 Sq Ft

    24560 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663

    Two bedroom, two bath home overlooking the Links at Perry Cabin. The spacious unit offers a living room with brick hearth fireplace, kitchen with table space and separate dining area. Relax on the rear patio overlooking a scenic community area and golf course. Minutes from downtown St. Michaels with boutique shops and restaurants.

    Jane Baker Benson & Mangold, LLC

    24560 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663
  • 7683 Tilghman Island Rd, Sherwood, MD 21665
    7683 Tilghman Island Rd, Sherwood, MD 21665
    7683 Tilghman Island Rd, Sherwood, MD 21665
    /41

    $499,000

    • 3 Beds
    • 1.5 Baths
    • 5,344 Sq Ft

    7683 Tilghman Island Rd, Sherwood, MD 21665

    BACK ON MARKET-by no fault of Seller. Welcome to this beautifully updated 3-bedroom, 1.5-bath home, offering both charm and versatility. The home features three spacious bedrooms, including one with an attached area that can serve as a walk-in closet, nursery, or home office—perfect for adapting to your needs. With 1.5 bathrooms, you'll enjoy the convenience of a full bath and an additional half

    Katie Mister Keller Williams Select Realtors of Cambridge

    7683 Tilghman Island Rd, Sherwood, MD 21665
  • 8898 New Rd, Wittman, MD 21676
    8898 New Rd, Wittman, MD 21676
    8898 New Rd, Wittman, MD 21676
    /26

    $289,000

    • 3 Beds
    • 2 Baths
    • 1,280 Sq Ft

    8898 New Rd, Wittman, MD 21676

    Discover peaceful country living at 8898 New Rd. This thoughtfully refreshed 3‑bed, 2‑bath ranch boasts a modern kitchen, an open floor plan, and natural light throughout. The primary suite offers comfort and privacy, while two extra bedrooms are perfect for family, guests, or a home office. Situated on a nearly half‑acre lot, the private backyard offers a relaxing escape or entertaining space.

    BJ Kilby EXIT On The Bay

    8898 New Rd, Wittman, MD 21676
  • 6253 Middle Point Rd, Neavitt, MD 21652
    6253 Middle Point Rd, Neavitt, MD 21652
    6253 Middle Point Rd, Neavitt, MD 21652
    /27

    $749,000

    • 4 Beds
    • 3 Baths
    • 4,164 Sq Ft

    6253 Middle Point Rd, Neavitt, MD 21652

    A myriad of possibilties come with this unique property. Two homes for the price of one. The main house has 3 BR’s and 2 full baths, and the attached smaller home has two BR’s and one full bath. Both have fireplaces and light filled rooms. Located on about 2.1 +/_ acres in a quiet country setting and just minutes to a Talbot County boat ramp.

    Jane Baker Benson & Mangold, LLC

    6253 Middle Point Rd, Neavitt, MD 21652
  • 21486 Mission Rd, Tilghman, MD 21671
    21486 Mission Rd, Tilghman, MD 21671
    21486 Mission Rd, Tilghman, MD 21671
    /35

    $699,000

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

    21486 Mission Rd, Tilghman, MD 21671

    History:"The Elms" is located on the Northeast corner of Mission Road and Route 33 in the village of Tilghman on Tilghman Island, Talbot County, MD. The house faces west, with the gable oriented on a north/south axis. Built around 1893. The Elms is clad in weatherboard and supported by a brick pier foundation. The roof of this two story frame home is covered in asphalt shingles. The five bay

    Daphne Cawley TTR Sotheby's International Realty

    21486 Mission Rd, Tilghman, MD 21671
  • 10425 Aberdeen Ln, Easton, MD 21601
    10425 Aberdeen Ln, Easton, MD 21601
    10425 Aberdeen Ln, Easton, MD 21601
    /81

    $1,695,000

    • 3 Beds
    • 2.5 Baths
    • 2,951 Sq Ft

    10425 Aberdeen Ln, Easton, MD 21601

    Conveniently located North of Easton with easy Rt 50 access, 9.8+/- acres on the upper Miles River, Southern exposure, dock with lift and electric, exceptional privacy with panoramic natural non developed land water views, with pool and gazebo, 3 car attached garage, exceptionally large trees and mature landscaping. Split floorplan offering 3,000+/- sf with primary bedroom on one side and other

    Bill Wieland Benson & Mangold, LLC

    10425 Aberdeen Ln, Easton, MD 21601
  • 0 Unionville Rd Unit MDTA2008824, Easton, MD 21601
    0 Unionville Rd Unit MDTA2008824, Easton, MD 21601
    0 Unionville Rd Unit MDTA2008824, Easton, MD 21601
    /5

    $1,250,000

    • Land
    • 48 Acres
    • $26,305 per Acre

    0 Unionville Rd Unit MDTA2008824, Easton, MD 21601

    Presenting 47+ acres of stunning land just minutes from Easton, perfectly positioned at the intersectionof Unionville Road and Miles River Road, extending along Anchorage Road. This expansive property iscurrently leased for farming and hunting, offering both income potential and recreational opportunities.While it has not been perc tested, the property holds potential for multiple

    Tracy Higgs-Wagner Meredith Fine Properties

    0 Unionville Rd Unit MDTA2008824, Easton, MD 21601
  • 25070 Hurley Ln, Saint Michaels, MD 21663
    25070 Hurley Ln, Saint Michaels, MD 21663
    25070 Hurley Ln, Saint Michaels, MD 21663
    /28

    $475,000

    • 3 Beds
    • 2.5 Baths
    • 1,505 Sq Ft

    25070 Hurley Ln, Saint Michaels, MD 21663

    Welcome to this stunning 3-Bedroom, 2.5 Bath home nestled in a tranquil, private cul-de-sac in a charming St. Michaels neighborhood. Be dazzled by the 30 foot vaulted ceiling, loft overlook and wood burning Fireplace. This beautifully maintained residence boasts an inviting open floor plan, the perfect ambiance for relaxation. The modern kitchen has been expertly remodeled with upgrades and

    Stephany Barrett Long & Foster Real Estate, Inc.

    25070 Hurley Ln, Saint Michaels, MD 21663
  • 0 Ocean Gateway Unit MDTA2008568, Easton, MD 21601
    0 Ocean Gateway Unit MDTA2008568, Easton, MD 21601
    0 Ocean Gateway Unit MDTA2008568, Easton, MD 21601
    /29

    $8,000,000

    • Land
    • 57 Acres
    • $141,293 per Acre

    0 Ocean Gateway Unit MDTA2008568, Easton, MD 21601

    Don’t miss out on this rare opportunity to transform this 56+/ -acre parcel into a premier development project This expansive property offers a blend of zoning options and fantastic exposure on Route 50, making it an ideal investment for developers. The property is well-suited for high-visibility projects including home improvement stores, pad sites, restaurants, and so much more. All utilities

    Barbara Watkins Benson & Mangold, LLC

    0 Ocean Gateway Unit MDTA2008568, Easton, MD 21601
  • 10376 Claiborne Rd, Claiborne, MD 21624
    10376 Claiborne Rd, Claiborne, MD 21624
    10376 Claiborne Rd, Claiborne, MD 21624
    /57

    $264,900

    • 3 Beds
    • 1 Bath
    • 1,282 Sq Ft

    10376 Claiborne Rd, Claiborne, MD 21624

    Looking for a sweet little cottage in a waterfront town minutes from Saint Michaels? The cottage has a brand-new septic system, just installed new toilet, vanity, stove, and refrigerator, hardwood floors, fireplace, large porch off the back, and short walk to Eastern Bay or Tilghman Creek. This home is ready to be loved by its next owner. This property is being sold "as is." Call today for

    Jana Meredith Meredith Fine Properties

    10376 Claiborne Rd, Claiborne, MD 21624
  • 6694 Hopkins Neck Rd, Easton, MD 21601
    6694 Hopkins Neck Rd, Easton, MD 21601
    6694 Hopkins Neck Rd, Easton, MD 21601
    /50

    $2,950,000

    • 4 Beds
    • 4 Baths
    • 5,690 Sq Ft

    6694 Hopkins Neck Rd, Easton, MD 21601

    This beautiful waterfront estate with broad views of Plaindealing Creek is being sold furnished (except for owners personal belongings and some artwork) and was tastefully decorated by Come by Chance out of St Michaels. Sited on 21 acres (zoned agricultural) the property provides the utmost in privacy, and features a waterside pool, hot tub, and pier with lift and 3+ MLW. The main house offers

    Laura Carney TTR Sotheby's International Realty

    6694 Hopkins Neck Rd, Easton, MD 21601
  • 00 New Rd, McDaniel, MD 21647
    00 New Rd, McDaniel, MD 21647
    00 New Rd, McDaniel, MD 21647
    /9

    $200,000

    • Land
    • 8 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
  • 9681 Macks Ln, McDaniel, MD 21647
    9681 Macks Ln, McDaniel, MD 21647
    /2

    $102,000

    • 2 Beds
    • 1 Bath
    • 920 Sq Ft

    9681 Macks Ln, McDaniel, MD 21647

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

    Lesley Jackson EXIT Sunshine Realty

    9681 Macks Ln, McDaniel, MD 21647
  • 402 N Talbot St, Saint Michaels, MD 21663
    402 N Talbot St, Saint Michaels, MD 21663
    /2

    $140,000

    • Land
    • 0.05 Acre
    • $2,800,000 per Acre

    402 N Talbot St, Saint Michaels, MD 21663

    A rare opportunity to own a residential lot in the heart of St. Michaels! Located at 402 Talbot St, this prime homesite offers the perfect blend of small-town charm and modern convenience. Just steps from shops, restaurants, and the waterfront, this property provides the ideal setting to build your dream home in one of Maryland’s most sought-after coastal communities.

    Catina Fair Northrop Realty

    402 N Talbot St, Saint Michaels, MD 21663
  • 5648 Trafalgar Cir, Tilghman, MD 21671
    5648 Trafalgar Cir, Tilghman, MD 21671
    5648 Trafalgar Cir, Tilghman, MD 21671
    /11

    $556,990 New Construction

    • 3 Beds
    • 2 Baths
    • 2,068 Sq Ft

    5648 Trafalgar Cir, Tilghman, MD 21671

    THIS HOME IS UNDER CONSTRUCTION!Welcome to Sussex, the epitome of modern rancher living! This single-level floor plan has captured the hearts of many, and it's not hard to see why. With stunning curb appeal and thoughtfully designed features and finishes, the Sussex offers versatility to suit any modern lifestyle. Step into an open-concept floor plan that seamlessly connects the Kitchen,

    Mary Ann Hammel Mary Ann Hammel

    5648 Trafalgar Cir, Tilghman, MD 21671
  • 25826 Orchard Terrace, Royal Oak, MD 21662
    25826 Orchard Terrace, Royal Oak, MD 21662
    25826 Orchard Terrace, Royal Oak, MD 21662
    /20

    $3,495,000 New Construction

    • 4 Beds
    • 4.5 Baths

    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
  • 110 Lee St, Saint Michaels, MD 21663
    110 Lee St, Saint Michaels, MD 21663
    110 Lee St, Saint Michaels, MD 21663
    /49

    $495,000 New Construction

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

    110 Lee St, Saint Michaels, MD 21663

    Welcome to 110 Lee Street, a brand-new single-level home tucked away in the heart of charming St. Michaels, Maryland. Thoughtfully designed and just completed in 2024, this home captures the perfect balance of modern elegance and small-town warmth, offering a lifestyle that’s as relaxed as it is refined.Step inside and experience an open-concept floor plan that effortlessly connects the living,

    Chance Stem LPT Realty, LLC

    110 Lee St, Saint Michaels, MD 21663
  • 25833 Turner Ave, Royal Oak, MD 21662
    25833 Turner Ave, Royal Oak, MD 21662
    25833 Turner Ave, Royal Oak, MD 21662
    /5

    $799,000 New Construction

    • 3 Beds
    • 2.5 Baths

    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
  • 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
  • 26698 Arcadia Shores Rd, Easton, MD 21601
    26698 Arcadia Shores Rd, Easton, MD 21601
    /2

    $775,000 Coming Soon

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

    26698 Arcadia Shores Rd, Easton, MD 21601

    Charming 4-Bedroom Cape Cod on 4 Private Acres with Pool & Sunroom!Welcome to your dream retreat! This beautifully maintained Cape Cod offers 4 spacious bedrooms and 3.5 baths, set on a serene 4-acre lot. Enjoy summer days by the in-ground pool, or unwind in the sunny, four-season sunroom. The inviting living room features a cozy wood stove—perfect for cool evenings. The expansive primary suite

    Becky Wibberley Coldwell Banker Realty

    26698 Arcadia Shores Rd, Easton, MD 21601
  • 0 Pot Pie Rd, Wittman, MD 21676
    0 Pot Pie Rd, Wittman, MD 21676
    0 Pot Pie Rd, Wittman, MD 21676
    /3

    $35,000

    • Land
    • 2.86 Acres
    • $12,238 per Acre

    0 Pot Pie Rd, Wittman, MD 21676

    ONLINE AUCTION: Bidding begins 06/18/2025 @ 10:00 AM. Bidding ends 06/20/2025 @ 11:30 AM. List Price is Suggested Opening Bid. Lot of Land located in Wittman, Maryland within Talbot County. Property is in close proximity to the many attractions in St. Michaels, Maryland. Easy Access to Major Traffic Artery Tilghman Island Road. Deposit: $7,500.

    Adam Shpritz Ashland Auction Group LLC

    0 Pot Pie Rd, Wittman, MD 21676
  • 6369 Neavitt Manor Rd, Neavitt, MD 21652
    6369 Neavitt Manor Rd, Neavitt, MD 21652
    6369 Neavitt Manor Rd, Neavitt, MD 21652
    /15

    $165,000

    • 2 Beds
    • 1 Bath
    • 832 Sq Ft

    6369 Neavitt Manor Rd, Neavitt, MD 21652

    Price adjustment! Opportunity abounds in this lovely 2 Bedroom 1 Bath detached home located in the picturesque waterfront town of Neavitt. This home boasts central air, attic space, a large yard, a shed and much more. Close to St. Michales and Tilghman Island this is a boaters and bird lovers paradise with a public boat ramp about a 1/2 mile away plus stores, shops , dining and

    Richard Perrera Century 21 Downtown

    6369 Neavitt Manor Rd, Neavitt, MD 21652
  • 21738 Cabin Ln, Sherwood, MD 21665
    21738 Cabin Ln, Sherwood, MD 21665
    21738 Cabin Ln, Sherwood, MD 21665
    /6

    $39,000

    • Land
    • 0.83 Acre
    • $46,988 per Acre

    21738 Cabin Ln, Sherwood, MD 21665

    .8 +/- private acres located in Sherwood, MD. Located 10 minutes from St. Michaels, MD and 5 minutes from Tilghman, MD.BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

    Shawn Moore Meredith Fine Properties

    21738 Cabin Ln, Sherwood, MD 21665
  • 21747 Cabin Ln, Sherwood, MD 21665
    21747 Cabin Ln, Sherwood, MD 21665
    21747 Cabin Ln, Sherwood, MD 21665
    /6

    $25,000

    • Land
    • 0.23 Acre
    • $108,696 per Acre

    21747 Cabin Ln, Sherwood, MD 21665

    .2 +/- private acres located in Sherwood, MD. Located 10 minutes from St. Michaels, MD and 5 minutes from Tilghman, MD.BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

    Shawn Moore Meredith Fine Properties

    21747 Cabin Ln, Sherwood, MD 21665

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