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Homes for Sale in 21666

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  • /44

    $579,000

    • 3 Beds
    • 3 Baths
    • 1,536 Sq Ft

    126 Watermans Cove Ln, Chester, MD 21619

    Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom home in the Waterman’s Cove community in Chester. Nestled on a quiet street along scenic Cox Creek, this charming property offers the perfect blend of comfort, style, and convenience. An inviting front porch welcomes you home, while water views greet you upon arrival and can also be enjoyed from the spacious rear composite deck, built

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 222-1760

    126 Watermans Cove Ln, Chester, MD 21619
  • /47

    $2,695,000 Open Sun 12PM - 2PM

    • 5 Beds
    • 3.5 Baths
    • 4,897 Sq Ft

    137 Tanners Point Dr, Stevensville, MD 21666

    Welcome home to this stunning waterfront property in Cove Creek Club on Kent Island. This remarkable five bedroom, four bathroom home offers an unparalleled blend of privacy, elegance, and panoramic coastal beauty all located on your very own private peninsula. With an impressive 566 feet of protected shoreline where Tanner’s Creek converges with Cove Creek, opening directly to the Eastern Bay,

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (410) 824-5374

    137 Tanners Point Dr, Stevensville, MD 21666
  • /44

    $719,000

    • 3 Beds
    • 2 Baths
    • 1,538 Sq Ft

    102 Golf Ct, Stevensville, MD 21666

    Tucked on a private 1-acre corner lot in the desirable Cove Creek community, this home offers 3 bedrooms, 2 baths, and 1,538 square feet of single-level living. Following a complete renovation, every detail has been refreshed—pairing modern updates with a light-filled open floor plan. Expansive windows and vaulted ceilings create a bright, airy feel, while the family room’s wood-burning fireplace

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (410) 517-7406

    102 Golf Ct, Stevensville, MD 21666
  • /58

    $1,397,500

    • 5 Beds
    • 4.5 Baths
    • 4,529 Sq Ft

    208 Tower Dr, Stevensville, MD 21666

    This stunning 4,500+ sq ft home with 5 bedrooms and 4.5 baths is set on a private 1.25-acre lot in the sought-after water-privileged Tower Gardens community—just minutes from the Bay Bridge. Ideal for generational living, the home features primary suites on both the first and second floors, offering flexibility for a variety of lifestyles. At the heart of the home, the gourmet kitchen boasts a

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (410) 205-1360

    208 Tower Dr, Stevensville, MD 21666
  • /80

    $869,900

    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft

    122 N Lake Dr, Stevensville, MD 21666

    New Price! Experience refined coastal living at 122 N. Lake Drive—a nearly new waterfront residence nestled along the tranquil waters of Carter Creek in Stevensville’s sought-after Tower Gardens community. With exclusive community beach access, a private boat launch, and close proximity to Romancoke Fishing Pier, this home is perfectly positioned to embrace the best of Eastern Shore living.

    Agent Photo

    Gretchen Wichlinski

    Compass

    (443) 272-4197

    122 N Lake Dr, Stevensville, MD 21666
  • /16

    $174,900

    • Land
    • 24,393 Sq Ft
    • $312,321 per Acre

    0 Touhey Dr Unit MDQA2016822, Kent Island, MD 21666

    This prime residential land parcel, located in the desirable ROMANCOKE ON THE BAY subdivision in Stevensville, MD, offers a unique investment or building opportunity with significant potential for appreciation. Spanning 0.56 acres, this corner lot features wooded areas, providing both privacy and a natural aesthetic that enhances the property's overall appeal. Strategically positioned just about

    Agent Photo

    Petra Quinn

    Realty Navigator

    (410) 883-7500

    0 Touhey Dr Unit MDQA2016822, Kent Island, MD 21666
  • /84

    $699,000

    • 4 Beds
    • 3.5 Baths
    • 3,536 Sq Ft

    109 Chesapeake Bay Dr, Stevensville, MD 21666

    Imagine your summer on Kent Island with views of the Chesapeake Bay! Welcome to this beautiful home offering two full living spaces — a spacious main level and a private in-law suite — perfect for multigenerational living, guest accommodations or an Airbnb. No HOA! The main living area, located on the second floor, features vaulted ceilings with exposed cross-beams, creating an open and airy

    Agent Photo

    Dustin Oldfather

    Compass

    (410) 883-9155

    109 Chesapeake Bay Dr, Stevensville, MD 21666
  • /40

    $799,990 New Construction

    • 3 Beds
    • 3 Baths
    • 2,230 Sq Ft

    313 Columbia Ln, Stevensville, MD 21666

    Experience the exceptional craftsmanship of Schaefer Homes with the Raleigh floorplan, now offered in the highly desirable water-access community of Queen Anne’s Colony. This thoughtfully designed new construction home offers the ease of single-level living, blending timeless coastal style with modern functionality—perfect for both everyday living and effortless entertaining. The heart of the

    Agent Photo

    Jamie Richardson

    RE/MAX United Real Estate

    (443) 806-7943

    313 Columbia Ln, Stevensville, MD 21666
  • /27

    $589,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,091 Sq Ft

    103 Worcester Rd, Stevensville, MD 21666

    THIS IS A TO BE BUILT HOME - Welcome to the Monroe—where timeless style meets modern living. This thoughtfully designed new construction home offers the perfect blend of comfort, functionality, and charm.From the moment you step inside, you’re greeted by a bright, open-concept layout with 9-foot ceilings and recessed lighting throughout, enhancing the home’s airy and inviting feel. The great

    Agent Photo

    Jamie Richardson

    RE/MAX United Real Estate

    (410) 453-8861

    103 Worcester Rd, Stevensville, MD 21666
  • /32

    $609,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,258 Sq Ft

    108 Lagorce Dr, Stevensville, MD 21666

    Brand new completed 2-story home offering 4 bedrooms, 2.5 baths, and glimpses of the Chesapeake Bay right down the street, NO HOA! This thoughtfully designed home features a spacious open layout highlighted by a large kitchen island with quartz countertops, full quartz backsplash, and stainless steel appliances—perfect for everyday living and entertaining.The primary suite includes a

    Agent Photo

    Jim Davidson

    Coldwell Banker Waterman Realty

    (410) 216-5726

    108 Lagorce Dr, Stevensville, MD 21666
  • /6

    $569,000 Open House 5/24

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

    107 Chestnut Rd, Stevensville, MD 21666

    Location, Location , Location - this gorgeous new custom 4BR home is just 2 blocks from the Bay and convenient to route 50 & the Bay Bridge for quicker commute. Walk to the waterfront community playground/rec area or put your boat in or fish at several nearby ramps/piers/parks. Lots of room and charm in this large home featuring a separate large freezer and refrigerator in the kitchen, granite

    Agent Photo

    Brenda Fornos

    Taylor Properties

    (410) 642-5631

    107 Chestnut Rd, Stevensville, MD 21666
  • /56

    $659,900

    • 2 Beds
    • 3 Baths
    • 2,074 Sq Ft

    784 Moorings Cir, Stevensville, MD 21666

    This beautifully maintained 2-bedroom, 3-bath home is located in a desirable 55 community and offers comfort, style, and convenience. Enter through a charming courtyard into a bright, open floor plan featuring cathedral ceilings and a spacious great room with a gas fireplace, perfect for relaxing or entertaining. The kitchen features granite countertops, ample cabinetry, and flows seamlessly into

    Deb Trombley Core Partners Realty LLC

    784 Moorings Cir, Stevensville, MD 21666
  • /45

    $429,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 3 Baths
    • 1,419 Sq Ft

    932 Kimberly Way, Stevensville, MD 21666

    Welcome to this charming and beautifully updated rancher located in the sought-after, water-access community of Cloverfields. This thoughtfully renovated home offers three bedrooms and three full bathrooms, with tasteful updates throughout the remodeled kitchen, great room, and baths. The light-filled great room is a true centerpiece, featuring vaulted ceilings with exposed rafters and an

    Barbara McCaffrey Redfin Corp

    932 Kimberly Way, Stevensville, MD 21666
  • /25

    $140,000

    • Land
    • 2.72 Acres
    • $51,471 per Acre

    000 St Marys Rd, Stevensville, MD 21666

    Located approximately 8 miles south of Stevensville in Queen Anne's County, this 2.72 acre wooded property consists of eight separate parcels, each approximately 0.34 acres in size. The parcels are situated in a quiet setting at the end of a cul-de-sac, offering limited through traffic and a more secluded access point via a private driveway. The property is predominantly wooded, providing natural

    Mike Arajakis Whitetail Properties Real Estate

    000 St Marys Rd, Stevensville, MD 21666
  • /24

    $349,900

    • Land
    • 22.49 Acres
    • $15,558 per Acre

    000 Romancoke Rd, Stevensville, MD 21666

    Located on Romancoke Road in Queen Annes County, this 22.49 acre wooded parcel offers a combination of privacy, natural surroundings, and accessibility. Situated approximately 8 miles south of Stevensville, the property is positioned in a primarily residential area with convenient access to nearby towns and regional travel routes. The land is predominantly wooded with mature pine trees that

    Mike Arajakis Whitetail Properties Real Estate

    000 Romancoke Rd, Stevensville, MD 21666
  • /48

    $650,000

    • 4 Beds
    • 3 Baths
    • 3,027 Sq Ft

    1024 Avalon Ct, Stevensville, MD 21666

    Privacy, Space, and Coastal CharmTucked away at the end of a peaceful cul-de-sac, this magnificent property offers the perfect blend of privacy and accessibility. With over 3,000 sq. ft. of thoughtfully designed living space, this home invites you to slow down and enjoy the finer things. Imagine crisp autumn evenings by the stone-accented fireplace in your light-filled living room, or hosting

    Michele Monti CENTURY 21 New Millennium

    1024 Avalon Ct, Stevensville, MD 21666
  • /69

    $975,000

    • 3 Beds
    • 2.5 Baths
    • 1,716 Sq Ft

    604 Broadcreek Dr, Stevensville, MD 21666

    This charming Colonial home in the desirable Bay City community offers a perfect blend of comfort and convenience. With 1,716 sq. ft. of well-designed space, the open floor plan features a cozy living area with a propane fireplace, a bright breakfast area, and a kitchen island ideal for gatherings. Enjoy the luxury of a primary bath with a jetted tub and stand alone shower. Step outside to a

    Tricia Wilson Wilson Realty & Staging LLC

    604 Broadcreek Dr, Stevensville, MD 21666
  • /30

    $799,990 New Construction

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    110 Boatswain Way Unit 42, Chester, MD 21619

    Gourmet kitchen with designer cabinetry & vast center island. Inviting great room featuring a cozy electric fireplace. Dry bar creates a polished space for serving & entertaining. Peaceful owner's suite with stylish tray ceiling & private bath. Home office with double doors offers a quiet, flexible workspace. Balcony extends the living space outdoors for relaxing or unwinding.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 42, Chester, MD 21619
  • /38

    $859,990 New Construction

    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft

    719 Warbler Way, Stevensville, MD 21666

    Welcome to the Simone, a beautifully designed home offering 4 bedrooms, 3 baths, and a 2-car garage. Scheduled for settlement in July 2026, this home combines thoughtful design with comfortable living spaces ideal for both everyday life and entertaining. The main living area features a cozy one-story fireplace, creating a warm and inviting focal point. A dedicated home office provides a private

    Mary Anne Kowalewski KOVO Realty

    719 Warbler Way, Stevensville, MD 21666
  • /24

    $799,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,150 Sq Ft

    0 Queens Colony High Rd, Stevensville, MD 21666

    To be built, brand new colonial featuring 4 bedrooms, 2.5 baths, two car garage. STANDARD FEATURES include LVP flooring, quartz countertops, stainless steel appliances, and more! Model home can be seen at 307 Columbia (different model but same builder). Pictures do show options

    DJ Dauses Coldwell Banker Waterman Realty

    0 Queens Colony High Rd, Stevensville, MD 21666
  • /47

    $670,000

    • 3 Beds
    • 2 Baths
    • 1,976 Sq Ft

    116 Mallard Dr, Stevensville, MD 21666

    Priced below Market!! Recently appraised at $690,000. Truly a Rare Find on Kent Island’s Eastern Shore.Welcome to your private retreat on beautiful Kent Island, where nature, comfort, and timeless design come together effortlessly. From the moment you arrive, you’ll be captivated by serene views of Mallard Pond, best enjoyed from the expansive front porch or the charming screened-in side

    Stephanie Smith Select Premium Properties, Inc

    116 Mallard Dr, Stevensville, MD 21666
  • /21

    $889,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    102 Boatswain Way Unit 21, Chester, MD 21619

    Gourmet kitchen with spacious central island & sleek finishes. Dining area with built-in dry bar for easy entertaining. Bright great room with electric fireplace & open layout. Private balcony just off the great room. Owner’s suite with dual walk-in closets for added storage. Sitting room in owner’s suite with direct balcony access. Spa-inspired owner’s bath with dual sinks & glass-enclosed

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 21, Chester, MD 21619
  • /29

    $774,900 New Construction

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

    101 Placek's Ln, Stevensville, MD 21666

    This two-story, two-car garage center hall design is a great multi-generational home option for families looking to accommodate lots of varying needs under one roof! The Congressional features a formal dining room, breakfast area, main level owner’s suite and laundry room, 4 bedrooms, 2.5 baths, mud room access from the garage, and much more. This plan offers numerous customization opportunities

    George Bailey Keller Williams Flagship

    101 Placek's Ln, Stevensville, MD 21666
  • /27

    $615,000

    • 3 Beds
    • 3 Baths
    • 1,906 Sq Ft

    324 Moorings Cir Unit 108, Stevensville, MD 21666

    Welcome to Bay Bridge Cove, an active adult 55+ community designed for comfort, convenience, and low-maintenance living. Residents enjoy exceptional amenities including a clubhouse with outdoor pool, fitness center, lounge, library, meeting space, and game room, along with walking trails, scenic ponds, pickleball and bocce courts, a crab shack, and community vegetable and herb gardens. Ideally

    Verna Downey Clark & Co Realty, LLC

    324 Moorings Cir Unit 108, Stevensville, MD 21666
  • /59

    $704,990

    • 4 Beds
    • 3 Baths
    • 2,400 Sq Ft

    201 Beachside Dr, Stevensville, MD 21666

    This home offers flexible living space in a water-privileged community and a lifestyle that’s hard to beat. Set on a generous 0.8 acre corner lot directly across from the Bay, this 4-bedroom, 3-bath home delivers space, scenery, and access to the water in one great package.The upper level features bright main living areas with a functional layout for everyday living and entertaining. The

    Marti McGinty Chesapeake Real Estate Associates, LLC

    201 Beachside Dr, Stevensville, MD 21666
  • /54

    $694,500 Coming Soon

    • 3 Beds
    • 3 Baths
    • 2,591 Sq Ft

    352 Topside Dr Unit 229, Stevensville, MD 21666

    Tucked away in one of the most private settings in Bay Bridge Cove, this beautifully maintained end-unit townhome offers the perfect blend of space, light, and peaceful surroundings. Backing to a tranquil pond and positioned at the rear of the community, this home delivers the kind of quiet retreat that is rarely available. Inside, you’ll find a thoughtfully designed layout featuring 3 bedrooms

    Kathleen Higginbotham Samson Properties

    352 Topside Dr Unit 229, Stevensville, MD 21666
  • /26

    $649,900

    • 3 Beds
    • 2.5 Baths
    • 2,843 Sq Ft

    438 Web Foot Ln, Stevensville, MD 21666

    Now vacant, refreshed, move-in ready, and available for immediate occupancy in sought-after Mallard Run. This beautifully maintained 3-bedroom, 2 full and 1 half bath home offers a hard-to-find layout with a main-level primary suite featuring vaulted ceilings, walk-in closet, and private ensuite bath — ideal for buyers seeking long-term main-level living with additional bedrooms and flex space

    Jill Rudiger Berkshire Hathaway HomeServices PenFed Realty

    438 Web Foot Ln, Stevensville, MD 21666
  • /45

    $679,000

    • 4 Beds
    • 2.5 Baths
    • 2,679 Sq Ft

    404 Queens Colony High Rd, Stevensville, MD 21666

    PRICE IMPROVED!! Welcome to 404 Queens Colony High Road, a beautifully situated home in the sought-after waterfront community of Queen Anne Colony. Nestled in Stevensville on Kent Island, this property offers the perfect blend of comfort, convenience, and coastal charm. Enjoy stunning views of the Chesapeake Bay and breathtaking sunsets right from your deck—creating the perfect backdrop for

    Jen Kenney Keller Williams Flagship

    404 Queens Colony High Rd, Stevensville, MD 21666
  • /40

    $699,800 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,300 Sq Ft

    233 Nichols Manor Dr, Stevensville, MD 21666

    One of our most popular designs, The New Doral offers formal and informal living areas with lots of room for the whole family to spread out. Your main level features a dining/den/flex space as well as a spacious family room and kitchen, breakfast area that flows to the spacious family room.. Add a light-filled morning room off the rear or expand your space with plan extensions. . Upstairs

    George Bailey Keller Williams Flagship

    233 Nichols Manor Dr, Stevensville, MD 21666
  • /46

    $665,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,564 Sq Ft

    303 Creeks End Ln, Stevensville, MD 21666

    Welcome to life on Kent Island in the sought-after Cox Creek Landing community—where coastal charm meets everyday convenience. With water access and a community pier, this neighborhood is perfect for embracing the Chesapeake Bay lifestyle, all just minutes from shopping, dining, and local amenities.From the moment you arrive, the inviting front porch sets the tone—an ideal spot to relax with

    Dee Dee Miller Paul Wesley Real Estate

    303 Creeks End Ln, Stevensville, MD 21666
  • /73

    $712,000

    • 4 Beds
    • 3 Baths
    • 2,870 Sq Ft

    266 Peregrine Dr, Stevensville, MD 21666

    Huge Price Reduction on this beautiful, less than 1 year old home in the sought after community of Four Seasons at Kent Island. This Simone model home with loft features 4 bedrooms and 3 full baths is awaiting it's next owner and priced well below the new construction models. With recent improvements including paint and Plantation Shutters, this home is move in ready so that you can enjoy this

    Edward Beres RE/MAX Executive

    266 Peregrine Dr, Stevensville, MD 21666
  • /57

    $723,400 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,210 Sq Ft

    109 Placek's Ln, Stevensville, MD 21666

    One of our most popular designs, the Doral offers formal and informal living areas with lots of room for the whole family to spread out. Your main level features a dining/den/flex space as well as a spacious family room and kitchen, breakfast area that flows to the spacious family room.. Add a light-filled morning room off the rear or expand your space with plan extensions. . Upstairs

    George Bailey Keller Williams Flagship

    109 Placek's Ln, Stevensville, MD 21666
  • /106

    $749,000

    • 3 Beds
    • 2 Baths
    • 2,230 Sq Ft

    301 Penny Dr, Stevensville, MD 21666

    Welcome to refined coastal living in the highly sought-after Cove Creek Club on Kent Island. Situated on approximately one acre, this beautifully maintained 3-bedroom, 2-bath home offers space, comfort, and an effortless Eastern Shore lifestyle. Upon entry, you’re greeted by a formal living room, while a second living area flows seamlessly into the open-concept kitchen and dining space, perfect

    Jarnell Foster Benson & Mangold, LLC

    301 Penny Dr, Stevensville, MD 21666
  • /59

    $624,900 Open Sat 1PM - 3PM

    • 3 Beds
    • 3 Baths
    • 2,074 Sq Ft

    222 Moorings Cir Unit 126, Stevensville, MD 21666

    Welcome home to refined coastal living on Maryland’s Eastern Shore in this beautifully designed 3-bedroom, 3-bath home located in the premier 55+ community of Bay Bridge Cove in Stevensville, Maryland.This lovely and well-maintained home was built in 2022 and offers 2,074 square feet over two levels. The home blends light-filled spaces with effortless, low-maintenance living just minutes from

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    222 Moorings Cir Unit 126, Stevensville, MD 21666
  • /52

    $799,990 New Construction

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    110 Boatswain Way Unit 3042, Chester, MD 21619

    Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home combines modern comfort with functional living spaces. The heart of the home features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. A dedicated home office with lited French doors provides a stylish and private

    Mary Anne Kowalewski KOVO Realty

    110 Boatswain Way Unit 3042, Chester, MD 21619
  • /2

    $699,000 Coming Soon

    • 5 Beds
    • 3.5 Baths
    • 3,582 Sq Ft

    335 Anna Carol Dr, Stevensville, MD 21666

    Professional photos will be added soon!

    Kelly Coward Keller Williams Flagship

    335 Anna Carol Dr, Stevensville, MD 21666
  • /38

    $689,900 New Construction

    • 4 Beds
    • 2.5 Baths

    114 Queens Colony High Rd, Stevensville, MD 21666

    One of our most popular designs, the Doral offers formal and informal living areas with lots of room for the whole family to spread out. Your main level features a dining/den/flex space as well as a spacious family room and kitchen, breakfast area that flows to the spacious family room.. Add a light-filled morning room off the rear or expand your space with plan extensions. . Upstairs

    George Bailey Keller Williams Flagship

    114 Queens Colony High Rd, Stevensville, MD 21666
  • /41

    $650,000

    • 4 Beds
    • 4 Baths
    • 2,630 Sq Ft

    322 Allison Jane Dr Unit H-4, Stevensville, MD 21666

    Welcome to Ellendale—where modern comfort meets Eastern Shore charm. This beautifully maintained 4-bedroom, 4 full bath townhome, built in 2023 by Baldwin Homes, offers a new feel with a spacious, light-filled layout and a 2-car garage. Designed for both everyday living and effortless entertaining, the home features stylish finishes throughout, plus a top-floor retreat complete with a private

    Max Burton Mr. Lister Realty

    322 Allison Jane Dr Unit H-4, Stevensville, MD 21666
  • /41

    $672,800 New Construction

    • 4 Beds
    • 2.5 Baths

    323 Chenowith Dr, Stevensville, MD 21666

    One of our most popular designs, the Doral offers formal and informal living areas with lots of room for the whole family to spread out. Your main level features a dining/den/flex space as well as a spacious family room and kitchen, breakfast area that flows to the spacious family room.. Add a light-filled morning room off the rear or expand your space with plan extensions. . Upstairs

    George Bailey Keller Williams Flagship

    323 Chenowith Dr, Stevensville, MD 21666
  • /82

    $715,000

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

    917 Moorings Cir Unit 131, Stevensville, MD 21666

    Welcome to this exceptional model home, fully loaded with upgrades and offering over 2,200 square feet of luxurious living space. The main level showcases beautiful luxury plank flooring and an open-concept design that seamlessly connects the dining room, kitchen, and great room—ideal for both everyday living and entertaining. Stylish shiplap wall accents and a whole-house sound system add to the

    Deborah Savoie Long & Foster Real Estate, Inc.

    917 Moorings Cir Unit 131, Stevensville, MD 21666

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