43

Homes for Sale in 21663

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  • 24830 Deepwater Point Dr, Saint Michaels, MD 21663
    24830 Deepwater Point Dr, Saint Michaels, MD 21663
    24830 Deepwater Point Dr, Saint Michaels, MD 21663
    /75

    $2,425,000 Open Fri 10:30AM - 12:30PM

    • 3 Beds
    • 2.5 Baths
    • 2,875 Sq Ft

    24830 Deepwater Point Dr, Saint Michaels, MD 21663

    DREAMING OF A BEACH HOUSE ? STUNNING LOCATION , ENDLESS BREEZES AND SUNSETS.....A treasure of vantage points and chic contemporary beauty, this Martingham waterfront retreat offers rare front-row views of Miles River happenings - including the historic Log Canoe Races, Fourth of July fireworks, daily passages of billowing sails,and, on crisp days, sightlines stretching to Kent Island Bridge.

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    24830 Deepwater Point Dr, Saint Michaels, MD 21663
  • 504 Seymour Ave, Saint Michaels, MD 21663
    504 Seymour Ave, Saint Michaels, MD 21663
    504 Seymour Ave, Saint Michaels, MD 21663
    /85

    $1,200,000 Open Sat 12PM - 2PM

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

    504 Seymour Ave, Saint Michaels, MD 21663

    Charming yet completely reimagined, this beautifully remodeled home offers refined Eastern Shore living at its best. Set on beautifully landscaped grounds featuring lovely water views and a partially fenced rear yard with paver patio. Thoughtfully designed and updated the main level features a modern kitchen with newer appliances, cozy breakfast room, living room with fireplace, formal dining

    Barbara Watkins Benson & Mangold, LLC

    504 Seymour Ave, Saint Michaels, MD 21663
  • 9206 Martingham Dr, Saint Michaels, MD 21663
    9206 Martingham Dr, Saint Michaels, MD 21663
    9206 Martingham Dr, Saint Michaels, MD 21663
    /69

    $749,000

    • 4 Beds
    • 2.5 Baths
    • 2,841 Sq Ft

    9206 Martingham Dr, Saint Michaels, MD 21663

    Beautiful four-bedroom contemporary home on a private one + acre lot overlooking the 12th fairway of the Links at Perry Cabin golf course. Light-filled interior features a vaulted living room with fireplace, spacious family room and dining room and a bright sunroom that opens to a relaxing private deck. The main-level primary suite includes two walk-in closets and a comfortable layout for

    Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    9206 Martingham Dr, Saint Michaels, MD 21663
  • 203 E Chew Ave, Saint Michaels, MD 21663
    203 E Chew Ave, Saint Michaels, MD 21663
    203 E Chew Ave, Saint Michaels, MD 21663
    /93

    $2,538,000

    • 4 Beds
    • 5 Baths
    • 4,673 Sq Ft

    203 E Chew Ave, Saint Michaels, MD 21663

    Welcome to 203 E Chew Avenue, a residence of exceptional craftsmanship and refined luxury, originally constructed in 2008 and thoughtfully reimagined through comprehensive renovations completed in 2023 and 2024. Encompassing more than 4,700 +/- square feet of finished living space, with 5 bedrooms, this home offers an elevated blend of sophistication, comfort, and timeless Eastern Shore charm—

    Richard Minchik Benson & Mangold, LLC

    203 E Chew Ave, Saint Michaels, MD 21663
  • 7149 Drum Point Rd, Saint Michaels, MD 21663
    7149 Drum Point Rd, Saint Michaels, MD 21663
    7149 Drum Point Rd, Saint Michaels, MD 21663
    /73

    $2,249,000

    • 3 Beds
    • 3 Baths
    • 3,017 Sq Ft

    7149 Drum Point Rd, Saint Michaels, MD 21663

    ST MICHAELS TUCKED AWAY ON DESIRABLE DRUM POINT NEIGHBORHOOD, MINUTES FROM THE BUZZLING TOWN OF ST MICHAELS AND ITS MANY RESTAURANTS, SHOPS , CAFES, THE MOTOR MUSEUM AND THE CHESAPEAKE BAY MARITIME MUSEUM. WHERE EVER YOU TURN YOU SEE WATER. FEEL THE BREEZES , LOUNGE BY THE POOL OR NAP IN YOUR HAMMOCK UNDER THE SHADY TREES BY THE SHORELINE. THIS THREE BEDROOM SOLID BRICK HOME WITH OPEN FLOORPLAN ,

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    7149 Drum Point Rd, Saint Michaels, MD 21663
  • 7909 Church Neck Rd, Saint Michaels, MD 21663
    7909 Church Neck Rd, Saint Michaels, MD 21663
    7909 Church Neck Rd, Saint Michaels, MD 21663
    /50

    $2,300,000

    • 4 Beds
    • 2.5 Baths
    • 4,492 Sq Ft

    7909 Church Neck Rd, Saint Michaels, MD 21663

    Pictures coming 4/11.Set on 19.5 private acres just minutes from historic waterfront Saint Michaels, this exceptional 4,492 sq ft residence offers the perfect blend of space, privacy, and convenience. The home features four bedrooms and two and a half baths, with expansive living areas ideal for both everyday living and entertaining, including a well-appointed chef's kitchen. The thoughtfully

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    7909 Church Neck Rd, Saint Michaels, MD 21663
  • 204 E Marengo St, Saint Michaels, MD 21663
    204 E Marengo St, Saint Michaels, MD 21663
    204 E Marengo St, Saint Michaels, MD 21663
    /72

    $599,000

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

    204 E Marengo St, Saint Michaels, MD 21663

    The perfect weekend getaway does exist — and it’s affordable. Escape the city / suburbs and spend your weekends in the quintessential Eastern Shore town of St. Michaels, known for its picturesque streets, quaint shops, vibrant dining scene, wineries, and distilleries. This charming waterfront community has everything you need to relax, recharge, and truly enjoy life on Maryland’s Eastern Shore -

    Agent Photo

    Gretchen Wichlinski

    Compass

    (844) 461-3815

    204 E Marengo St, Saint Michaels, MD 21663
  • 7865 Pea Neck Rd, Saint Michaels, MD 21663
    7865 Pea Neck Rd, Saint Michaels, MD 21663
    7865 Pea Neck Rd, Saint Michaels, MD 21663
    /60

    $1,379,800 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,332 Sq Ft

    7865 Pea Neck Rd, Saint Michaels, MD 21663

    Under construction by Laine Street Homes, this exceptional property offers over 3,300 sq ft of finished living space plus an additional 480 sq ft of covered outdoor living. Set on approximately 2 acres with mature trees and located just minutes from the heart of historic St. Michaels, the home blends privacy, luxury, and convenience. Designed with a main-level primary suite, the floor plan

    Jana Meredith Meredith Fine Properties

    7865 Pea Neck Rd, Saint Michaels, MD 21663
  • 0 Deepwater Point Dr, Saint Michaels, MD 21663
    0 Deepwater Point Dr, Saint Michaels, MD 21663
    0 Deepwater Point Dr, Saint Michaels, MD 21663
    /41

    $249,000

    • Land
    • 1.12 Acres
    • $222,321 per Acre

    0 Deepwater Point Dr, Saint Michaels, MD 21663

    ONE OF THE LAST LOTS IN MARTINGHAM ON DEEP WATER POINT DRIVE. LOCATED VERY CLOSE TO THE COMMUNITY WATERFRONT PARK WITH GAZEBO AND CHAIRS FOR PICKNICKS OR JUST RELAXING IN THE BREEZE WATCHING THE BOATS GO BY ; DROP YOUR KAYAK OR ENJOY THE SUNSETS, WALK OR BIKE THERE. THIS LOT IS CLEANED, HAS A BEAUTIFUL ENTRANCE , WATER METER, AND IS READY FOR YOU TO BUILT YOUR MAIN RESIDENCE OR WEEKEND GET AWAY.

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    0 Deepwater Point Dr, Saint Michaels, MD 21663
  • 24965 Back Creek Dr, Saint Michaels, MD 21663
    24965 Back Creek Dr, Saint Michaels, MD 21663
    24965 Back Creek Dr, Saint Michaels, MD 21663
    /64

    $739,000

    • 4 Beds
    • 2.5 Baths
    • 2,798 Sq Ft

    24965 Back Creek Dr, Saint Michaels, MD 21663

    Tucked into the heart of Back Creek Landing, this home offers the kind of layout and setting that just works—comfortable, well thought out, and connected to both nature and town. The main living space is designed around how people actually live. The kitchen is open and inviting, with a bright eat-in area and an elevated counter with seating—perfect for morning coffee, casual meals, or simply

    Kathleen Coale Benson & Mangold, LLC

    24965 Back Creek Dr, Saint Michaels, MD 21663
  • 113 Gloria Ave, Saint Michaels, MD 21663
    113 Gloria Ave, Saint Michaels, MD 21663
    113 Gloria Ave, Saint Michaels, MD 21663
    /36

    $595,000 Open Sat 2PM - 4PM

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft

    113 Gloria Ave, Saint Michaels, MD 21663

    Situated on a corner lot just minutes from downtown St. Michaels, this 3-bedroom, 2-bath home offers easy access to local shops, restaurants, and the Maritime Museum. Inside, the living room is filled with natural light from a large bay window and features LVP flooring, recessed lighting, and updated fixtures throughout. The kitchen and dining area provide an open, functional layout with direct

    Peter Stark Benson & Mangold, LLC

    113 Gloria Ave, Saint Michaels, MD 21663
  • 303 Manor St, Saint Michaels, MD 21663
    303 Manor St, Saint Michaels, MD 21663
    303 Manor St, Saint Michaels, MD 21663
    /105

    $1,985,000 Open Sat 1PM - 3PM

    • 3 Beds
    • 3 Baths
    • 2,622 Sq Ft

    303 Manor St, Saint Michaels, MD 21663

    Welcome to "Mostly Porches" an exceptional coastal retreat with captivating views of the harbor, perfectly situated on a spacious .41 acre corner lot just around the corner from the shops and restaurants of St. Michaels. Built in 2018 with virtually maintenance-free construction, this beautifully designed home offers the ideal blend of comfort, style, and convenience in a rare St. Michaels

    Monica Penwell TTR Sotheby's International Realty

    303 Manor 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
    /59

    $1,885,000

    • 3 Beds
    • 2.5 Baths
    • 2,284 Sq Ft

    222 E Chestnut St, Saint Michaels, MD 21663

    Where the harbor meanders to a close and drifting ducks replace the bustle of boats, this 2,284 square foot colonial captivates as serene dockside stillness gives way to elevated coastal personality. Whether welcoming guests from its end-of-lane circular drive or stepping ashore from one of your four boat slips, your restful retreat pampers with beautifully renovated interiors by local shop, Come

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    222 E Chestnut St, Saint Michaels, MD 21663
  • 114 W Chestnut St, St. Michaels, MD 21663
    114 W Chestnut St, St. Michaels, MD 21663
    114 W Chestnut St, St. Michaels, MD 21663
    /73

    $1,350,000

    • 4 Beds
    • 4.5 Baths
    • 3,528 Sq Ft

    114 W Chestnut St, St. Michaels, MD 21663

    Ideally located in the heart of the St. Michaels Historic District, this beautifully maintained three-story home offers exceptional walkability just a half block from the waterfront, scenic walking trail, public park and kayak launch, as well as the shops, restaurants, and other amenities that make St. Michaels such a sought-after place to live. A welcoming front porch introduces an inviting

    Wink Cowee Benson & Mangold, LLC

    114 W Chestnut St, St. Michaels, MD 21663
  • 106 E Chestnut St, Saint Michaels, MD 21663
    106 E Chestnut St, Saint Michaels, MD 21663
    106 E Chestnut St, Saint Michaels, MD 21663
    /39

    $1,325,000

    • 2 Beds
    • 2.5 Baths
    • 2,282 Sq Ft

    106 E Chestnut St, Saint Michaels, MD 21663

    Luxury Restoration in the Heart of Historic St. Michaels Welcome to 106 E. Chestnut Street, where historic charm and modern luxury come together in one of the Eastern Shore’s most beloved waterfront towns. Completely renovated down to the studs, this exceptional home has been thoughtfully reimagined to preserve its classic character while introducing high-end systems, refined finishes, and modern

    Justin Pokrywka Taylor Properties

    106 E Chestnut St, Saint Michaels, MD 21663
  • 24645 Long Haul Rd, Saint Michaels, MD 21663
    24645 Long Haul Rd, Saint Michaels, MD 21663
    24645 Long Haul Rd, Saint Michaels, MD 21663
    /112

    $2,750,000 Open Sun 12PM - 2PM

    • 3,677 Sq Ft

    24645 Long Haul Rd, Saint Michaels, MD 21663

    Experience waterfront living at its finest in this remarkable St. Michaels retreat, where breathtaking water views define every moment. The beautifully remodeled main level was designed to maximize the scenery, seamlessly blending indoor comfort with the natural beauty beyond. A chef-inspired kitchen with Monogram stainless steel appliances anchors the open-concept living space, perfect for

    Donna Dickinson Coldwell Banker Realty

    24645 Long Haul Rd, Saint Michaels, MD 21663
  • 938 Marea Terrace, Saint Michaels, MD 21663
    938 Marea Terrace, Saint Michaels, MD 21663
    938 Marea Terrace, Saint Michaels, MD 21663
    /63

    $2,390,000

    • 4 Beds
    • 5.5 Baths
    • 3,000 Sq Ft

    938 Marea Terrace, Saint Michaels, MD 21663

    Fabulous in-town St. Michaels waterfront property – This coastal style waterfront residence, built in 2020, offers approximately 3,000 square feet of thoughtfully designed, sophisticated yet relaxed waterfront living space on San Domingo Creek. Located within town limits, the property enjoys direct access to the St. Michaels Nature Trail, allowing effortless walkability to shops, dining, and

    Carolina Barksdale Benson & Mangold, LLC

    938 Marea Terrace, Saint Michaels, MD 21663
  • 100 Bush Terrace, Saint Michaels, MD 21663
    100 Bush Terrace, Saint Michaels, MD 21663
    100 Bush Terrace, Saint Michaels, MD 21663
    /40

    $480,000

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    100 Bush Terrace, Saint Michaels, MD 21663

    This home allows for a 3.12% FHA Assumable Loan! Welcome to easy Eastern Shore living in the charming waterfront town of St. Michaels! This 3-bedroom, 2 bath, 1,232 sq. ft. home is located in the desirable community of Rio Vista offering direct access to the Miles River, complete with a community dock, boat slips, and boat ramp — perfect for boating, crabbing, paddleboarding, or sunset cruises.

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    100 Bush Terrace, Saint Michaels, MD 21663
  • 9180 Saint Michaels Rd, Saint Michaels, MD 21663
    9180 Saint Michaels Rd, Saint Michaels, MD 21663
    9180 Saint Michaels Rd, Saint Michaels, MD 21663
    /66

    $1,685,000

    • 5 Beds
    • 5 Baths
    • 4,728 Sq Ft

    9180 Saint Michaels Rd, Saint Michaels, MD 21663

    UNIQUE PROPERTY RIGHT OUTSIDE OF HISTORIC ST MICHAELS TOWN LIMITS ACROSS THE LINK AT PERRY CABIN. THIS FABULOUS HOME OFFERS SPACE FOR GATHERINGS WITH FAMILY OR FRIENDS BUT ALSO FEELS COZY FOR EMPTY NESTERS THAT LOVE TO ENTERTAIN. THERE ARE NO RESTRICTIONS THAT PROHIBIT VACATION RENTAL, THERE SHOULD BE SPACE FOR AN INGROUND POOL .ORIGINALLY BUILD IN 1973 THE CURRENT OWNER GUTTED THE HOME, ALL

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    9180 Saint Michaels Rd, Saint Michaels, MD 21663
  • 9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
    /36

    $480,000

    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft

    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663

    Set within the sought-after Martingham community of Quail Hollow, backing to the top rated golf course The Links at Perry Cabin, this fully updated 3-bedroom, 3-bath townhome offers stylish, low-maintenance living just minutes from downtown St. Michaels. Extensive renovations completed between 2022 and 2024 make this home truly turnkey. The main level welcomes you with beautiful wood floors, a

    Barbara Watkins Benson & Mangold, LLC

    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
  • 101 Mulberry St, Saint Michaels, MD 21663
    101 Mulberry St, Saint Michaels, MD 21663
    101 Mulberry St, Saint Michaels, MD 21663
    /38

    $1,194,000 Open Sat 1PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    101 Mulberry St, Saint Michaels, MD 21663

    Beautifully restored Historic Victorian in the heart of Saint Michaels. This charming home has a strong rental history, last tenant was paying $4,500 a month. From the wide, welcoming front porch to the gated, manicured yard—complete with a hammock ideal for long afternoon naps—every space is designed for comfort and relaxation. A brick walkway leads to the custom beveled‐glass entry door and

    Jana Meredith Meredith Fine Properties

    101 Mulberry St, Saint Michaels, MD 21663
  • 228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
    /119

    $1,995,000

    • 6 Beds
    • 6 Baths
    • 4,089 Sq Ft

    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663

    Check out the NEW aerial photos! An exceptional opportunity in The Homes at Perry Cabin -- a rare double residence offering approximately 4,000 square feet, six bedrooms, and six full baths in a premier Saint Michaels waterfront community. adjacent to the renowned Inn at Perry Cabin and overlooking Fogg Cove just off the Miles River. This turnkey home features expansive living areas and a

    Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
  • 205 Cherry St, St. Michaels, MD 21663
    205 Cherry St, St. Michaels, MD 21663
    205 Cherry St, St. Michaels, MD 21663
    /64

    $2,575,000

    • 5 Beds
    • 8.5 Baths
    • 4,394 Sq Ft

    205 Cherry St, St. Michaels, MD 21663

    205 Cherry Street is one of the most prestigious addresses in historic St. Michaels. Originally built as a single-family residence, it currently operates as an Inn. It is being marketed both as a 7 bedroom inn and also as a single family residence, offering 5 bedrooms (including the first floor primary bedroom suite). The original living room/office with fireplaces on the first floor are

    Robert Lacaze TTR Sotheby's International Realty

    205 Cherry St, St. Michaels, MD 21663
  • 114 E Chew Ave, Saint Michaels, MD 21663
    114 E Chew Ave, Saint Michaels, MD 21663
    114 E Chew Ave, Saint Michaels, MD 21663
    /57

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 2,336 Sq Ft

    114 E Chew Ave, Saint Michaels, MD 21663

    The George E. Shockley House (c. 1890) is a rare historic gem in the heart of St. Michaels, just moments from the harbor, fine dining, unique shops, walking trails, and the renowned Chesapeake Bay Maritime Museum. Beautifully preserved and enhanced with significant structural improvements by Victor MacSorley, this distinguished residence blends period charm with modern comfort and is notably not

    Wink Cowee Benson & Mangold, LLC

    114 E Chew Ave, Saint Michaels, MD 21663
  • 1211 Washington Dr, Saint Michaels, MD 21663
    1211 Washington Dr, Saint Michaels, MD 21663
    1211 Washington Dr, Saint Michaels, MD 21663
    /14

    $525,000

    • 4 Beds
    • 4 Baths
    • 2,420 Sq Ft

    1211 Washington Dr, Saint Michaels, MD 21663

    DESIREABLE RIO VISTA LIVING -MOVE IN ONE SIDE OF THIS DUPLEX AND RENT THE OTHER ONE TO HELP PAYING FOR YOUR MORTGAGE. THESE DUPLEXES RARELY BECOME AVAILABLE.The duplex is located in a water access community with dock access through the owner's approved application and payment.The building consists of two units with mirrored floor plans. They offer a kitchen with small eating area, an open

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    1211 Washington Dr, Saint Michaels, MD 21663
  • 1215 Washington Dr, Saint Michaels, MD 21663
    1215 Washington Dr, Saint Michaels, MD 21663
    1215 Washington Dr, Saint Michaels, MD 21663
    /30

    $525,000

    • 4 Beds
    • 4 Baths
    • 2,420 Sq Ft

    1215 Washington Dr, Saint Michaels, MD 21663

    DESIREABLE RIO VISTA LIVING -MOVE IN ONE SIDE OF THIS DUPLEX AND RENT THE OTHER ONE TO HELP PAYING FOR YOUR MORTGAGE. THESE DUPLEXES RARELY BECOME AVAILABLE. The duplex is located in a water access community with dock access through the owner's approved application and payment. The building consists of two units with mirrored floor plans. They offer a kitchen with small eating area, an open

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    1215 Washington Dr, Saint Michaels, MD 21663
  • 101 Brooks Ln, Saint Michaels, MD 21663
    101 Brooks Ln, Saint Michaels, MD 21663
    101 Brooks Ln, Saint Michaels, MD 21663
    /19

    $425,000 Open Sat 11AM - 12:30PM

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    101 Brooks Ln, Saint Michaels, MD 21663

    Welcome to this beautifully updated cottage in the heart of St. Michaels—where modern comfort meets Eastern Shore charm. Perfectly situated within walking distance to the town’s shops, restaurants, Rails to Trails, and the renowned Maritime Museum, this single‐level home offers both convenience and a peaceful, private setting. Sitting on nearly a quarter acre, the property features a fully fenced

    Stacie Luhrman Benson & Mangold, LLC

    101 Brooks Ln, Saint Michaels, MD 21663
  • 111 Gloria Ave, Saint Michaels, MD 21663
    111 Gloria Ave, Saint Michaels, MD 21663
    111 Gloria Ave, Saint Michaels, MD 21663
    /33

    $435,000 Open Sat 2PM - 4PM

    • 2 Beds
    • 1.5 Baths
    • 1,125 Sq Ft

    111 Gloria Ave, Saint Michaels, MD 21663

    Essentially a NEW HOME! Extensively, tastefully and professionally renovated 1965 rancher located on a quiet residential street, just 2 blocks from downtown St. Michaels. Nearly everything is brand new, including roof shingles, siding, windows, HVAC system and new deck. New off-street parking area, sized for 2 vehicles. Inside, everything looks (and is) new, too, including attractive luxury vinyl

    Tom Crouch Benson & Mangold, LLC

    111 Gloria Ave, Saint Michaels, MD 21663
  • 24700 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663
    24700 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663
    24700 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663
    /47

    $369,000

    • 2 Beds
    • 2.5 Baths
    • 1,486 Sq Ft

    24700 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663

    Price improvement! Inviting townhouse in the St. Michaels Martingham community with views across the Links at Perry Cabin fairway, offering easy Eastern Shore living. From the upstairs living areas, enjoy lovely, elevated views, abundant natural light, and a sense of openness that enhances the home’s warm, inviting feel. The upper-level living area features shining hardwood floors, and the home

    Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    24700 Deepwater Point Dr Unit 1, Saint Michaels, MD 21663
  • 107 W Chestnut St, Saint Michaels, MD 21663
    107 W Chestnut St, Saint Michaels, MD 21663
    107 W Chestnut St, Saint Michaels, MD 21663
    /105

    $1,225,000

    • 3 Beds
    • 2 Baths
    • 1,914 Sq Ft

    107 W Chestnut St, Saint Michaels, MD 21663

    Your picture-perfect St. Michaels Bungalow on the coveted W. Chestnut Street. The owners completed a full renovation in 2023. Designer finishes throughout. Attention to detail, light placement and thoughtful preservation of its original style. The screened front porch welcomes you in with it's beautiful woodwork and sets the pace for this Chic, move-in ready Shore Home. Situated on a double lot

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    107 W Chestnut St, Saint Michaels, MD 21663
  • 216 E Chew Ave, Saint Michaels, MD 21663
    216 E Chew Ave, Saint Michaels, MD 21663
    216 E Chew Ave, Saint Michaels, MD 21663
    /144

    $1,795,000 Open Sat 12PM - 2PM

    • 1 Bath
    • 3,575 Sq Ft

    216 E Chew Ave, Saint Michaels, MD 21663

    Don't miss this rare opportunity. This special home offers spectacular and picturesque views of the Saint Michaels Harbor in addition to its prime location on one of Saint Michaels most desirable streets. Conveniently located near all of the in-town amenities and walkable to great restaurants, shops, brewery, winery, gallery, seasonal farmer's market, museums and more. This home has received a

    Agent Photo

    Christopher Clinton

    Coldwell Banker Chesapeake Real Estate Company

    (855) 940-3395

    216 E Chew Ave, Saint Michaels, MD 21663
  • 105 Seymour Ave, Saint Michaels, MD 21663
    105 Seymour Ave, Saint Michaels, MD 21663
    105 Seymour Ave, Saint Michaels, MD 21663
    /39

    $474,000

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

    105 Seymour Ave, Saint Michaels, MD 21663

    SAINT MICHAELS CHARMING COTTAGE! Welcome Home to this Adorable Cottage perfectly situated in the desirable and walkable Historic Waterfront Town of Saint Michaels! Full of natural light and warmth, this inviting home offers comfortable living spaces and thoughtful updates. A sizable .25 Acre lot with mature trees to include a pecan and walnut tree, mature flower gardens, zoysia grass and an

    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
    /25

    $779,000 New Construction

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

    108 Miles, Saint Michaels, MD 21663

    A rare opportunity to pair a half-acre+ wooded in-town parcel with a thoughtfully designed single-level home concept in the heart of St. Michaels. This Concept A plan illustrates a 3-bedroom, 2-bath residence totaling approximately 1,710 square feet, featuring one-level living and an attached one-car garage. Designed to maximize functionality and flow, the concept offers flexible living spaces

    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
    /25

    $999,000 New Construction

    • 3 Beds
    • 2.5 Baths

    108 Miles, Saint Michaels, MD 21663

    A rare opportunity to combine a half-acre+ wooded in-town setting with a classic Cape Cod–style home concept in the heart of St. Michaels. Concept B illustrates a two-story design featuring 3 bedrooms, 2 full baths, and 1 half bath, along with an attached two-car garage. The proposed layout offers a timeless architectural style with flexible living spaces that can be customized to suit individual

    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
    /27

    $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
  • 23961 Lynnewood Dr, Saint Michaels, MD 21663
    23961 Lynnewood Dr, Saint Michaels, MD 21663
    23961 Lynnewood Dr, Saint Michaels, MD 21663
    /71

    $3,100,000 Open Sun 11AM - 1PM

    • 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

    $1,679,000

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

    24390 Oakwood Park Rd, Saint Michaels, MD 21663

    Price Improvement! 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

    Janet Larson Benson & Mangold, LLC

    24390 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 dining

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    9545 Quail Hollow Dr Unit 205, 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

    $219,000

    • Land
    • 0.25 Acre
    • $876,000 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
  • 23857 Ebb Point Rd, Bozman, MD 21612
    23857 Ebb Point Rd, Bozman, MD 21612
    23857 Ebb Point Rd, Bozman, MD 21612
    /88

    $1,895,000 Open Sat 1PM - 3PM

    • 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

    Tiffany Cloud Meredith Fine Properties

    23857 Ebb Point Rd, Bozman, MD 21612

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