Homes for Sale near St. Michaels Middle/High School

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  /108

  $8,250,000

  • 7 Beds
  • 5.5 Baths
  • 8,478 Sq Ft

  24390 Ln, Royal Oak, MD 21662

  Welcome to Deep Neck Farm Lane, a stately waterfront farm overlooking Broad Creek with sweeping west and southwest views that stretch over the Choptank River to the Western Shore. This extraordinary estate captures dramatic sunsets, summer breezes, and shelter from northern winds, all from an unrivaled vantage point. Built in 2006 by a builder for their family, the 8,500± square foot residence

  Coard Benson Benson & Mangold, LLC

  24390 Ln, Royal Oak, MD 21662
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  /49

  $499,888 New Construction

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

  5654 Trafalgar Cir, Tilghman, MD 21671

  Kim Crouch Ozman Benson & Mangold, LLC

  5654 Trafalgar Cir, Tilghman, MD 21671
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  /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 walkability with

  Tammy Durbin Long & Foster Real Estate, Inc.

  300 Perry St, Saint Michaels, MD 21663
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  /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
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  /69

  $3,000,000

  • 5 Beds
  • 5.5 Baths
  • 4,602 Sq Ft

  5440 Ferry Neck Rd, Royal Oak, MD 21662

  Welcome to ‘Drake’s Landing’! Beautifully sited on 20 picturesque acres on the shores of Irish Creek, this 4,602 sq. ft .completely renovated (2021) waterfront estate offers the perfect blend of casual elegance and thoughtful design. The main level welcomes with expansive water views and features a guest bedroom with ensuite bath, a cozy family room (or den/office), and a gracious living room

  Laura Carney TTR Sotheby's International Realty

  5440 Ferry Neck Rd, Royal Oak, MD 21662
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  $554,990 New Construction

  • 3 - 4 Beds
  • 2 - 3 Baths
  • 1,795+ Sq Ft

  Sussex Plan at Tilghman on Chesapeake, Tilghman Island, MD 21671

  Gemcraft Homes Builder

  21600 Island Club Rd Unit 36449305, Tilghman Island, MD 21671
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  /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
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  /47

  $1,745,000

  • 6 Beds
  • 6 Baths
  • 4,397 Sq Ft

  6020 Sunset Ln, Tilghman, MD 21671

  Welcome to Tilghman Landing on the Chesapeake Bay! This unique waterview property offers an incredible opportunity, featuring two separate homes with garages with unbelievable views of the Bay!Home #1: 6020 Sunset LaneThis spacious residence offers breathtaking, unobstructed views of the Bay. It includes 3 bedrooms and 2.5 bathrooms, and showcases an open-concept main level with a living

  Melissa Tippett TTR Sotheby's International Realty

  6020 Sunset Ln, Tilghman, MD 21671
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  /23

  $495,500

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  6343 Bozman Neavitt Rd, Neavitt, MD 21652

  UNIQUE COTTAGE IN A GREAT VILLAGE SETING WITH A DOCK PROVIDING ACCESS TO BALL CREEK AND QUICK ACCES TO THE CHESAPEAKE WITH GREAT FISHING AND SAILING! Ready for an updating with good bones this would be a wonderful weekender or short term rental. Typical Eastern Shore rural village with great folks it can even be replaced with the home of your dreams.Dock offers a 3 foot channel and has

  Bill Wieland Benson & Mangold, LLC

  6343 Bozman Neavitt Rd, Neavitt, MD 21652
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  /46

  $4,750,000

  • 5 Beds
  • 7 Baths
  • 5,554 Sq Ft

  21721 Heavenly Haven Rd, Sherwood, MD 21665

  This remarkable property has it all. Private 15 plus acres. Beautiful views overlooking Dunn's Cove sunrises. A shore sportsman's dream. Partially wooded, fields of crops, hunting blind and a pier for your fishing vessel. This was a large compound with the Main house, in-law wing and a separate 2 BR guest house w/fireplace and large screened porch. Waterside in-ground pool and children's play

  Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

  21721 Heavenly Haven Rd, Sherwood, MD 21665
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  /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
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  /18

  $835,000 Open Sat 11AM - 1PM

  • 4 Beds
  • 3.5 Baths
  • 4,201 Sq Ft

  8095 N Fork Blvd, Easton, MD 21601

  Expected date for available showings 12/26/25 - Easton Village - Custom built in 2007 featuring an ipe front porch and rear patio with hot tub, fenced yard, formal living/dining areas, first-floor primary suite with large closets, and high-end bath features. The kitchen has a center island joining a two-story family room with a gas fireplace. The second floor includes a landing overlooking the

  Coard Benson Benson & Mangold, LLC

  8095 N Fork Blvd, Easton, MD 21601
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  /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
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  /14

  $325,000

  • 3 Beds
  • 2 Baths
  • 3,924 Sq Ft

  22314 Pot Pie Rd, Wittman, MD 21676

  Rental Opportunity in Wittman, MD Positioned in the desirable community of Wittman, this 3 bedroom, 2 bath home situated on 0.84± commercially zoned acreage and premier road frontage presents a compelling opportunity for investors seeking potential rental income in Talbot County. The property offers comfortable living space, a rural Eastern Shore setting, and proximity to key employment,

  Shawn Moore Meredith Fine Properties

  22314 Pot Pie Rd, Wittman, MD 21676

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