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Homes for Sale near St. Michaels Middle/High School

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  • /10

    $729,000

    • Land
    • 5.48 Acres
    • $133,029 per Acre

    9361 Woodstock Ln, Easton, MD 21601

    GORGEOUS WATERFRONT LOT, PRIME LOCATION IN EASTONLook no further....this is the perfect spot on Maryland's beautiful Eastern Shore on which to build your dream home. This 5.5+/- acre, cleared lot enjoys a high elevation, offers lovely water views of Goldsborough Creek, and has been perc approved for 6 bedrooms! Envision living in a quiet, country setting in the Woodstock Farm

    Peter Frevel Benson & Mangold, LLC

    9361 Woodstock Ln, 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
  • /40

    $649,000

    • 3 Beds
    • 1.5 Baths
    • 2,316 Sq Ft

    27843 Saint Michaels Rd, Easton, MD 21601

    Secluded Eastern Shore farmhouse. Just over a mile outside Easton, this rare unknown property has been home to an artist couple for nearly 25 years. Its long tree lined drive opens into an authentic and romantic retreat. Set on 2+/- acres, it is surrounded by mature Willow Oaks, English boxwoods, heirloom plantings and a huge Magnolia tree. Inside, it features original oak floors and whitewashed

    Denis Gasper Benson & Mangold, LLC

    27843 Saint Michaels Rd, Easton, MD 21601
  • /3

    $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
  • /2

    $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
  • /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
  • /109

    $2,650,000

    • 4 Beds
    • 5 Baths
    • 5,207 Sq Ft

    26090 Royal Oak Rd, Easton, MD 21601

    This house is a showstopper! A work of art that feels part castle, part cathedral! Pictures don't do it justice! It's a unique, historic, waterfront estate that combines privacy & nature & excellent location on Oak Creek between St. Michaels & Easton. The treelined drive welcomes you to this one of a kind home built in 1890 and situated on 11.59 acres. Featuring stained glass transoms, the

    Kate Koeppen Chesapeake Bay Real Estate Plus, LLC

    26090 Royal Oak Rd, Easton, MD 21601
  • /31

    $469,500 Open Sun 11AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,834 Sq Ft

    6403 Bozman Neavitt Rd, Neavitt, MD 21652

    Located in the historic village of Neavitt, this charming house was built in 1890. It was thoroughly renovated in 2011 and the layout adapted for modern living, with light-filled rooms and a cleverly updated floor plan. The first-floor public spaces include a sitting room/office/entry, a generous living/dining room combination, and a handsome kitchen with water views, terrific storage, and

    Joan Wetmore TTR Sotheby's International Realty

    6403 Bozman Neavitt Rd, Neavitt, MD 21652
  • /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
  • /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
  • /52

    $2,700,000

    • 3 Beds
    • 3 Baths
    • 7,949 Sq Ft

    6976 Travelers Rest Cir, Easton, MD 21601

    Welcome to Soleil on the Bay! Nestled on nearly 7 acres along the scenic Maxmore Creek—just off the Tred Avon River—this exceptional west-facing waterfront property offers the most gorgeous sunsets providing the perfect blend of privacy, natural beauty, and endless potential. Ideally located between Easton and St. Michaels, it provides easy access to the best of Maryland’s Eastern Shore.Enter

    Clifford Meredith Meredith Fine Properties

    6976 Travelers Rest Cir, Easton, MD 21601
  • /18

    $350,000

    • Land
    • 0.55 Acre
    • $636,364 per Acre

    108 Miles, Saint Michaels, MD 21663

    Price Improved! Build your dream home on this one-of-a- kind, half+ acre (24,082 sf) wooded lot in the heart ofSaint Michaels. Offering a tranquil, park-like setting, this rare property provides both privacy andconvenience, a five-minute walk to the town’s charming restaurants, coffeeshops, events and shopping. Located just outside the historic district line, this unusuallylarge

    Jana Meredith Meredith Fine Properties

    108 Miles, Saint Michaels, MD 21663
  • /62

    $600,000

    • 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
  • /45

    $3,500,000

    • 3 Beds
    • 5 Baths
    • 4,305 Sq Ft

    6906 Travelers Rest Cir, Easton, MD 21601

    This expansive 3-bedroom, 5-bathroom contemporary home is nestled on over 4 acres along the picturesque Tred Avon River. Ideally situated between Easton and St. Michaels, this property offers the perfect blend of privacy and convenience. Featuring an open floorplan with soaring cathedral ceilings, it’s designed for both comfort and style. Additional features include a spacious primary suite

    Clifford Meredith Meredith Fine Properties

    6906 Travelers Rest Cir, Easton, MD 21601
  • /32

    $745,000

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft

    27232 Hayward Trail, Easton, MD 21601

    First time offered in 50 years! Discover this hidden gem nestled along 200' of waterfrontage on Hayward Cove, opening onto the scenic Miles River. Located on at the end of the street, between Easton and St. Michaels this colonial style home is situated on a 1+ acre lot with mature trees, offering three bedrooms, two bathrooms, beautiful wood flooring, a cozy dining area accentuated by a free

    Barbara Watkins Benson & Mangold, LLC

    27232 Hayward Trail, Easton, MD 21601
  • /47

    $2,495,000

    • 3 Beds
    • 3.5 Baths
    • 3,847 Sq Ft

    21825 Langdon Farm Rd, Sherwood, MD 21665

    It doesn't get any better than this ! Stunning brand-new ,one-story coastal residence with a contemporary flair! As soon as you enter this magnificent home, you will be captivated by 20'+ ceilings, superb craftsmanship , an extremely well-designed open floor-plan; breathtaking water-views on Dun Cove and a luxurious yet inviting kitchen. There are a total of 3 en-suite bedrooms as well as an

    Robert Lacaze TTR Sotheby's International Realty

    21825 Langdon Farm Rd, Sherwood, MD 21665
  • /40

    $615,000

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    204 E Marengo St, Saint Michaels, MD 21663

    Coastal charm meets small-town living in this beautifully updated cottage, just one block from the Historic District and 1.5 blocks from water access, including a marina and boat ramp, and downtown Saint Michaels! This home exudes a true vacation vibe, offering main-level living with sun-filled spaces designed for relaxation. The completely remodeled full bathroom adds modern comfort, while the

    Jennifer Chino Compass

    204 E Marengo St, Saint Michaels, MD 21663
  • /42

    $4,249,900

    • 4 Beds
    • 5.5 Baths
    • 5,062 Sq Ft

    27029 Miles River Rd, Easton, MD 21601

    Irish Tides offers a quintessential Eastern Shore retreat with luxury and style. This beautifully crafted4-bedroom, 5.5-bath main house provides captivating views of the Miles River from almost every room. The main level has been enhanced with a new HVAC system and ductwork, ensuring comfort andefficiency throughout. Exquisite crown moldings, hardwood floors, and custom built-ins add an

    Chuck Mangold Benson & Mangold, LLC

    27029 Miles River Rd, Easton, MD 21601
  • /33

    $550,000 Open Sun 11AM - 1PM

    • 2 Beds
    • 2 Baths
    • 1,570 Sq Ft

    6394 Bozman Neavitt Rd, Neavitt, MD 21652

    Wow- price reduced! This lovely primary/second home in a charming waterfront community just got better!!!! 12 miles from St Michaels, the house was built by the Neavitt family c. 1870. The light-filled first floor boasts a living room with built-ins, spacious dining room, sunny bedroom/office, full bath, and cathedral-ceilinged kitchen opening to a patio. Two bedrooms and a full bath are

    Joan Wetmore TTR Sotheby's International Realty

    6394 Bozman Neavitt Rd, Neavitt, MD 21652
  • /58

    $554,999

    • 3 Beds
    • 2.5 Baths
    • 2,110 Sq Ft

    5582 Trafalgar Cir, Tilghman, MD 21671

    This has an assumable VA loan! The Nottingham, (elevation Z) is a modern ranch-style home with 3 bedrooms, 2.5 baths, and a 2-car garage with entry through a mudroom that leads to an expansive Great Room area that opens to the Kitchen. The Kitchen is ready for entertaining and cooking comforting meals for family and friends. An open dinette and large kitchen island offer a plethora of space for

    Stacie Luhrman Benson & Mangold, LLC

    5582 Trafalgar Cir, Tilghman, MD 21671
  • /22

    $189,900

    • 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
  • /17

    $550,000

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft

    6343 Bozman Neavitt Rd, Neavitt, MD 21652

    Rustic Charm on Balls Creek - Wake up to sunrise views over Balls Creek from this charming 2-bedroom waterfront cottage. With nearly 200 feet of water frontage and a private pier, this serene retreat is perfect for weekend escapes filled with fishing, kayaking, or simply unwinding by the water’s edge. The cozy, nostalgic layout features a living room with wood floors, a dining area, and an

    Kathy Christensen TTR Sotheby's International Realty

    6343 Bozman Neavitt Rd, Neavitt, MD 21652
  • /47

    $449,000

    • 3 Beds
    • 3.5 Baths
    • 1,504 Sq Ft

    8013 Ruby Harrison Rd, Bozman, MD 21612

    What a transformation this Victorian beauty has undergone! With high ceilings, new windows, and gorgeous engineered wide plank wood floors, the downstairs is open and light. A stylish kitchen with island overlooks the dining area and large sliders open to a private side yard, where glimpses of nearby Harris Creek may be seen. The front room provides a comfortable seating area. Upstairs are

    Debra Crouch Benson & Mangold, LLC

    8013 Ruby Harrison Rd, Bozman, MD 21612
  • /91

    $4,395,000

    • 4 Beds
    • 4 Baths
    • 7,903 Sq Ft

    5084 Ferry Neck Rd, Royal Oak, MD 21662

    Secured driveway entry, appointment only. State of the art composition of nature and architecture. Set on the banks of the Choptank River this extremely private, 6000+ square foot, contemporary home on 80+/- acres offers expansive southwest views of the Chesapeake Bay. Personal beach, protected shoreline, 1800 feet of waterfrontage and room for waterfront pool. INCLUDED IN THE SALE is a 33.6+/-

    Brian Petzold Benson & Mangold, LLC

    5084 Ferry Neck Rd, Royal Oak, MD 21662
  • /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
  • /57

    $349,000

    • 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
  • /38

    $400,000

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

    7683 Tilghman Island Rd, Sherwood, MD 21665

    This Sherwood home truly has it all—history, charm, and modern updates. Included is the Historic Sherwood Store, which served the community for more than 160 years. A detached two-bay garage adds even more room for parking, storage, or workshop space. Just around the corner, you’ll also find a public dock and kayak launch on Harris Creek, Where you can moor your boat or jump in for a swim. It

    Katie Mister Keller Williams Select Realtors of Cambridge

    7683 Tilghman Island Rd, Sherwood, MD 21665
  • /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
  • /25

    $550,000

    • Land
    • 2.44 Acres
    • $225,410 per Acre

    7649 Cooper Point Rd, Bozman, MD 21612

    Just 7 miles (10 -12 minute drive) outside historic St. Michaels, MD: Rare 2.44-acre waterfront parcel of land with 488' of stable shoreline along the waters of Grace Creek, a scenic tributary of Broad Creek. Outstanding sunrise views looking directly down the creek! Actually, this offering includes 2 separate lots of record....a 2-acre lot and a .4-acre lot. The larger parcel features higher

    Tom Crouch Benson & Mangold, LLC

    7649 Cooper Point Rd, Bozman, MD 21612
  • /29

    $8,000,000

    • Land
    • 56.62 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
  • /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
  • /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

    Coard Benson Benson & Mangold, LLC

    24390 Ln, Royal Oak, MD 21662
  • /5

    $589,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,865 Sq Ft

    26972 Tunis Mills Rd, Easton, MD 21601

    Home is currently under construction with an completion date of Feb 2026. This 3BR, 2.5BA open concept rancher sits on a 0.4 acre lot and will include high end finishes throughout. The spacious kitchen will feature stylish thin shaker white and timber cabinetry with satin bronze hardware, quartz countertops, subway tile backsplash, and stainless steels appliances including a double oven, gas

    Adam Ellison Long & Foster Real Estate, Inc.

    26972 Tunis Mills Rd, Easton, MD 21601
  • /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
  • /15

    $499,888 New Construction

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

    5654 Trafalgar Cir, Tilghman, MD 21671

    The New Castle is a modern ranch-style home with 3 bedrooms, 2.5 baths, and a 2 car garage with drop zone entry, attached to a laundry room, that leads through to the Kitchen. The Kitchen has a large amount of space, plenty of cabinets, and a pantry, making storage and organization plentiful and manageable. The well-equipped kitchen is ready for entertaining and with family and friends. The open

    Mary Ann Hammel Mary Ann Hammel

    5654 Trafalgar Cir, Tilghman, MD 21671
  • /6

    $2,075,000 New Construction

    • 3 Beds
    • 3.5 Baths
    • 3,300 Sq Ft

    9361 Woodstock Ln Unit 7, Easton, MD 21601

    Welcome to your future waterfront home in Easton! This 'to-be-built' contemporary, coastal-style home will offer 3,300 square feet on an elevated 5.5+/- acre lot with water views of Goldsborough Creek and 3 bedrooms, 3.5 bathrooms, and spacious 2-car garage. Buyer will have the option to finish approx. 600 sqft above the garage as a one-bedroom unit with kitchenette for a total square footage of

    Peter Frevel Benson & Mangold, LLC

    9361 Woodstock Ln Unit 7, Easton, MD 21601
  • /25

    $544,888 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
  • /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
  • /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
  • /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

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