159

Talbot County MD 2-Story Homes for Sale

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  • /45

    $699,900

    • 3 Beds
    • 3 Baths
    • 2,660 Sq Ft

    4957 Bar Neck Rd, Tilghman, MD 21671

    If no contract by April 24, 2026, Seller will be removing home from market. Looking for a home with a private setting, water views, a pool, and no HOA — all within easy reach of the charm and activities of St. Michaels and Easton? Interested in a quiet home retreat or a short term rental?Look no further! Enjoy privacy, water views, and the freedom of no HOA at this tucked-away property located at

    Danny Martin Keller Williams Flagship

    4957 Bar Neck Rd, Tilghman, MD 21671
  • /48

    $1,995,000

    • 5 Beds
    • 3.5 Baths
    • 4,310 Sq Ft

    22707 Marshall Ln, Wittman, MD 21676

    Private Harris Creek waterfront with pool, pier boat lift and deep water access—ideal for boating kayaking and quiet days on the water. Five bedrooms and three-and-a-half baths designed for a relaxed yet refined Eastern Shore lifestyle. Featuring sun-filled interiors feature red oak floors custom built-ins multiple fireplaces and wide water views. The kitchen is designed for gathering with

    Kathy Christensen TTR Sotheby's International Realty

    22707 Marshall Ln, Wittman, MD 21676
  • /69

    $739,000

    • 4 Beds
    • 2.5 Baths
    • 2,876 Sq Ft

    28241 Knapps Lot St, Easton, MD 21601

    Ideally located in the highly sought-after waterfront community of Easton Village, this beautifully maintained home offers nearly 3,000 square feet of refined living just minutes from downtown Easton, St. Michaels, and Oxford, and conveniently close to Easton Airport with jet service—perfect for those seeking an effortless Eastern Shore lifestyle. Set on a premier, oversized corner lot, the

    Eddie Mangold Benson & Mangold, LLC

    28241 Knapps Lot St, Easton, MD 21601
  • /116

    $7,500,000

    • 6 Beds
    • 8 Baths
    • 8,476 Sq Ft

    7508 Cooper Point Rd, Bozman, MD 21612

    Set along the peaceful waters of Caulk Cove, this extraordinary waterfront estate offers luxury, privacy and natural beauty across more than 10 acres. The property features open farm fields and professionally landscaped, park-like grounds, with a tree-lined driveway creating a breathtaking approach to the residence. Built in 2013, the custom-designed home encompasses nearly 8,500 square feet of

    Kim Crouch Ozman Benson & Mangold, LLC

    7508 Cooper Point Rd, Bozman, MD 21612
  • /38

    $335,000

    • 4 Beds
    • 2.5 Baths
    • 1,916 Sq Ft

    505 Wheatley Dr, Easton, MD 21601

    Move-in ready, one-owner end-unit townhome built in 2022, proudly owner-occupied and meticulously maintained, located in the desirable Patriot Square community. This home offers 4 bedrooms and 2.5 bathrooms, with a primary suite and private bathroom on the main level, along with a convenient half bath—perfect for main-level living. The upper level features three additional bedrooms and one full

    Shay Prattis Keller Williams Realty

    505 Wheatley Dr, Easton, MD 21601
  • /105

    $1,295,000

    • 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
  • /35

    $524,000

    • 3 Beds
    • 2.5 Baths
    • 3,052 Sq Ft

    7459 Timothys Way, Easton, MD 21601

    Welcome to this 2-story McDaniel model in Easton Club East, perfectly situated on a spacious corner lot just moments from the clubhouse, pool, and tennis courts. Every inch of this home is drenched in sunlight from its southern exposure, enhanced by recessed lighting that makes the open floor plan glow from morning to evening. The freshly painted interiors, rebuilt fireplace insert, and enclosed

    Laura Anderson Coldwell Banker Realty

    7459 Timothys Way, Easton, MD 21601
  • /37

    $495,000 Open Sat 11AM - 12:30PM

    • 4 Beds
    • 2.5 Baths
    • 2,342 Sq Ft

    8800 Roundhouse Cir, Easton, MD 21601

    Move-In Ready Kensington Model in Mulberry Station. Welcome home to this spacious 4 bedroom, 2.5 bath residence offering over 2,300 sq. ft. of beautifully designed living space in the sought-after Mulberry Station community. Perfectly positioned on a large lot that backs to open farmland, this property combines modern upgrades with timeless charm. Key Features & Upgrades: 9’ ceilings on the main

    Stacie Luhrman Benson & Mangold, LLC

    8800 Roundhouse Cir, Easton, MD 21601
  • /71

    $700,000

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

    26698 Arcadia Shores Rd, Easton, MD 21601

    Charming 5-Bedroom Cape Cod on 4 Private Acres with Pool, Sunroom & Endless Outdoor BeautyWelcome to your dream retreat! Tucked away on 4 private, park-like acres, this beautifully maintained 5-bedroom, 3.5-bath Cape Cod blends timeless charm with thoughtful modern updates. Relax or entertain with ease—whether you're enjoying summer afternoons by the in-ground pool (with a 20-year liner, only

    Becky Wibberley Coldwell Banker Realty

    26698 Arcadia Shores Rd, Easton, MD 21601
  • /71

    $499,000

    • 3 Beds
    • 2.5 Baths
    • 2,138 Sq Ft

    3962 Main St, Trappe, MD 21673

    This unique and well maintained home is located in the heart of Trappe and has a lot to offer. Main home features formal living and dining areas, family room, kitchen, laundry, 1.5 baths on the first floor. 2nd floor has 3 spacious bedrooms and bath. Wood floors throughout home and all windows are currently being replaced (Dec. 2025). Warm radiator oil heat and mini-split units heat and cool the

    Judy Moore Benson & Mangold, LLC

    3962 Main St, Trappe, MD 21673
  • /39

    $385,000

    • 2 Beds
    • 1.5 Baths
    • 1,364 Sq Ft

    8805 Cummings Rd, Wittman, MD 21676

    Located in the waterfront village of Wittman, close to the public landing and county park, this beautifully crafted two-story cottage blends charm and character with thoughtful design. The home features 2 bedrooms, 1.5 baths, multiple living areas and 2 office spaces . Open beams, wood floors, and architectural details create a warm, inviting atmosphere throughout. Meticulous renovations by a

    Wink Cowee Benson & Mangold, LLC

    8805 Cummings Rd, Wittman, MD 21676
  • /58

    $4,395,000

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

    5084 Ferry Neck Rd, Royal Oak, MD 21662

    Tucked within a canopy of trees along Maryland’s Eastern Shore, this remarkable home rests quietly beside the Choptank River. The setting feels worlds away, eighty acres of meadows and woodland that open gently to more than 1,800 feet of private shoreline, where a western exposure captures breathtaking sunsets reflected across the water. The residence at 5084 Ferry Neck Road was shaped by owners

    Ron Mangas TTR Sothebys International Realty

    5084 Ferry Neck Rd, Royal Oak, MD 21662
  • /32

    $549,000

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

    21486 Mission Rd, Tilghman, MD 21671

    This historic property known as "The Elms" was built in 1900 and originally used as a fishing lodge for many years. The property sits on 2 acres, has public sewer and well water and consists of three buildings which are: The original main building, the detached garage and a shed/storage building. The buildings hold virtually no value unless an extensive historic renovation were completed, but the

    Monica Penwell TTR Sotheby's International Realty

    21486 Mission Rd, Tilghman, MD 21671
  • /83

    $1,950,000

    • 5 Beds
    • 4.5 Baths
    • 4,303 Sq Ft

    21485 Island Club Rd, Tilghman, MD 21671

    Discover the essence of refined Eastern Shore living in this meticulously renovated contemporary waterfront retreat, gracefully set along the tranquil shores of Harris Creek and looking out to the Choptank River. Every detail of this remarkable home exemplifies elegance. Step inside to a breathtaking panorama of water views framed by expansive windows that fill the home with ethereal lighting.

    Alicia Gannon Dulin Benson & Mangold, LLC

    21485 Island Club Rd, Tilghman, MD 21671
  • /66

    $795,000

    • 3 Beds
    • 2.5 Baths
    • 3,166 Sq Ft

    24912 Back Creek Dr, Saint Michaels, MD 21663

    Back Creek Landing home for sale in St. Michaels, MD — located in one of the town’s most desirable neighborhoods, known for its peaceful setting, friendly community, and proximity to downtown St. Michaels. This home is just minutes away by bike or golf cart, offering easy access to shops, restaurants, the harbor, and waterfront activities while still feeling private and serene. This beautifully

    Kathleen Coale Benson & Mangold, LLC

    24912 Back Creek Dr, Saint Michaels, MD 21663
  • /47

    $569,000

    • 4 Beds
    • 2.5 Baths
    • 3,429 Sq Ft

    2669 Ocean Gateway, Trappe, MD 21673

    Enjoy the serenity of country living just minutes from both downtown Easton and Cambridge! This spacious four bedroom, two and a half bath home offers over 3,400 square feet of living space and sits on nearly an acre (.96+/-) with covered front porch and nice rear deck with views of open fields/farmland. This solid house offers a comfortable layout on both levels and it's perfect for both

    Barbara Watkins Benson & Mangold, LLC

    2669 Ocean Gateway, Trappe, MD 21673
  • /38

    $749,000

    • 3 Beds
    • 2.5 Baths
    • 2,819 Sq Ft

    28959 Jasper Ln, Easton, MD 21601

    Totally renovated and in perfect move in condition this private end unit in The Galloways is available for immediate occupancy! Recently remodeled with a sun room addition and beautiful pergola and deck along with a new HVAC compressor in needs absolutely nothing. As an end unit with excellent privacy it offers a 2 car garage, spacious foyer, office with cherry cabinetry, half bath, new kitchen

    Bill Wieland Benson & Mangold, LLC

    28959 Jasper Ln, Easton, MD 21601
  • /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
  • /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
  • /87

    $5,500,000

    • 3 Beds
    • 4 Baths
    • 5,921 Sq Ft

    5499 Anderby Hall Rd, Royal Oak, MD 21662

    Royal Oak - escape to your own Eastern Shore estate. Anderby Hall is part of an original 1680 land grant. This 12 +/- acre parcel features 3,260' +/- of shoreline (mostly rip rapped) including a tidal pond and island (accessed by bridge)to a private peninsula and private cove. The gated driveway leads to the main house- a 3000 +/- sq.ft. Colonial featuring a great room with fireplace, charming

    Valerie Brown Coldwell Banker Realty

    5499 Anderby Hall Rd, Royal Oak, MD 21662
  • /31

    $770,000

    • 4 Beds
    • 3.5 Baths
    • 2,531 Sq Ft

    28933 Jasper Ln, Easton, MD 21601

    Back on market due to BUYER not being able to sell their house! Clean inspections so READY for YOU!This beautifully sited end-unit townhouse has serene field views, and offers 2,433 sq. ft. of elegant living with 4 bedrooms, 3 full baths, and 1 half bath. Designed with an open concept, the living room, dining room, and kitchen flow seamlessly together, creating a warm and inviting space for

    Laura Carney TTR Sotheby's International Realty

    28933 Jasper Ln, Easton, MD 21601
  • /32

    $275,000

    • 3 Beds
    • 1 Bath
    • 902 Sq Ft

    303 Market St Unit UT4, Oxford, MD 21654

    Hard to find condo in Oxford’s Historic District. Close to water, boat slips and marinas, shops, town park and restaurants. Living room with electric fireplace, kitchen, 3 bedrooms and 1 bath. Balcony. Heat pump.

    Ray Stevens Benson & Mangold, LLC

    303 Market St Unit UT4, Oxford, MD 21654
  • /70

    $3,095,000 Open Sat 1PM - 3PM

    • 4 Beds
    • 3.5 Baths
    • 3,088 Sq Ft

    5837 Irish Creek Rd, Royal Oak, MD 21662

    Absolutely stunning mid-century contemporary estate offering a private , park-like setting, with heated swimming pool, pavilion, luxurious fully equipped outdoor- kitchen, outdoor shower, in -ground hot tub ,tennis court, and maintenance -free Azek pier with new 30K lb. boat lift. Meticulously maintained inside and out! Professionally landscaped with WiFi controlled front/rear irrigation

    Robert Lacaze TTR Sotheby's International Realty

    5837 Irish Creek Rd, Royal Oak, MD 21662
  • /83

    $945,000

    • 3 Beds
    • 3 Baths
    • 3,130 Sq Ft

    29862 Paddock Ln, Easton, MD 21601

    Custom-built Cape Cod on 22.69 acres in the desirable McShell Glenn community! This charming home welcomes you with a full-length front porch and an inviting open floor plan. The gourmet kitchen is a true highlight, featuring stainless steel appliances, a breakfast bar, and a spacious walk-in pantry, seamlessly connecting to the dining room and family room—perfect for entertaining. The first

    Melissa Tippett TTR Sotheby's International Realty

    29862 Paddock Ln, Easton, MD 21601
  • /49

    $499,900

    • 4 Beds
    • 2.5 Baths
    • 2,094 Sq Ft

    8862 Roundhouse Cir, Easton, MD 21601

    Private backyard in Vibrant Community. Get lost in this backyard oasis close to downtown Easton in the very exciting neighborhood of Mulberry Station. Minutes from downtown Easton, you will get lost in all the special nooks and crannies hiding in your hidden paradise. Lose yourself in a book under the Crepe Myrtles, Zen out next to the manmade ponds with water features. Who needs a sound machine

    Juliet Wells Coldwell Banker Chesapeake Real Estate Company

    8862 Roundhouse Cir, Easton, MD 21601
  • /50

    $1,200,000

    • 4 Beds
    • 2.5 Baths
    • 3,040 Sq Ft

    21477 Island Club Rd, Tilghman, MD 21671

    Welcome to waterfront living at its finest on picturesque Tilghman Island! This beautifully maintained 3,040 sq ft Colonial offers stunning open water views and a lifestyle of comfort, elegance, and ease. Boasting four spacious bedrooms and two and a half baths, this home features a flowing floor plan with natural light, generous living spaces, and a perfect blend of indoor and outdoor

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    21477 Island Club Rd, Tilghman, MD 21671
  • /69

    $2,795,000

    • 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
  • /46

    $3,700,000

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

    21721 Heavenly Haven Rd, Sherwood, MD 21665

    GENEROUS PRICE REDUCTION!!!! 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

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    21721 Heavenly Haven Rd, Sherwood, MD 21665
  • /86

    $7,500,000

    • 5 Beds
    • 6 Baths
    • 10,000 Sq Ft

    7090 Cooper Point Rd, Bozman, MD 21612

    Welcome to this extraordinary waterfront estate, gracefully sited on 6.92 lush, landscaped acres with sweeping views of Leadenham Creek. Designed by architect Alan Meyers, constructed by Ilex Construction, and masterfully styled by interior designer Skip Sroka, this 10,000+/-sq. ft. residence is a showcase of timeless craftsmanship and elevated design. The custom brick exterior is crowned by a

    Laura Carney TTR Sotheby's International Realty

    7090 Cooper Point Rd, Bozman, MD 21612
  • /88

    $1,895,000 Open Fri 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
  • /46

    $685,000

    • 3 Beds
    • 3 Baths
    • 2,703 Sq Ft

    29414 Andrew Ln, Easton, MD 21601

    **PRICE IMPROVEMENT**PARK LIKE SETTING- MATURE TREES- CREEK- BRIDGE ALL ON 3.064 PRIVATE ACRES*** Meticulously Maintained 3/4 bedroom, 3 bath home, With Bonus Room or Possible in-law/Au Pair Suite with Wheelchair access doors and a Chairlift for easy upstairs living access. Private in ground Pool with Gazebo. Woods in back half of property with your own Creek and Bridge to access back half of

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    29414 Andrew Ln, Easton, MD 21601
  • /70

    $749,999

    • 4 Beds
    • 3.5 Baths
    • 3,010 Sq Ft

    24977 Back Creek Dr, Saint Michaels, MD 21663

    Discover a beautifully crafted custom home tucked within the peaceful St. Michaels community, where refined design meets everyday comfort. This exceptional residence offers 4 generously sized bedrooms and 3.5 thoughtfully designed bathrooms, filled with premium details throughout. The versatile gas fireplace anchors the inviting main living space, complemented by custom built-ins that add both

    Eddie Mangold Benson & Mangold, LLC

    24977 Back Creek Dr, Saint Michaels, MD 21663
  • /31

    $435,500

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

    6403 Bozman Neavitt Rd, Neavitt, MD 21652

    A great new price for a terrific property! Located in Neavitt, a charming village of +/-seventy houses located at the end of a peninsula, it's about 12 miles from the shops and restaurants of St Michaels but is in another, quieter world. The village has its own park and playground, a public landing with a launch for canoes, an active community association, AND there are no St Michaels

    Joan Wetmore TTR Sotheby's International Realty

    6403 Bozman Neavitt Rd, Neavitt, MD 21652
  • /27

    $12,000,000

    • 3 Beds
    • 2 Baths
    • 2,397 Sq Ft

    29587 Matthewstown Rd, Easton, MD 21601

    124 +/- acres on the edge of Easton Md town limits. Farm is currently in row crop production. Situated between Matthewstown Run and Waylands subdivisions, this property is ideal for development potential located in priority areas two and three of Easton's Comprehensive Plan Growth Map. BUYER'S RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

    Shawn Moore Meredith Fine Properties

    29587 Matthewstown Rd, Easton, MD 21601
  • /66

    $499,000

    • 3 Beds
    • 2.5 Baths
    • 3,052 Sq Ft

    29830 Hillary Ave, Easton, MD 21601

    Nestled in the serene Easton Club East/Chesapeake by Del Webb community, this exquisite 3-bedroom, 2.5-bathroom residence is designed for those seeking a refined lifestyle. With a minimum age requirement of 55, this vibrant community offers a perfect blend of comfort and luxury. Step inside to discover a spacious 3,052 sq. ft. layout adorned with elegant crown moldings and wood flooring. The

    Judy Moore Benson & Mangold, LLC

    29830 Hillary Ave, Easton, MD 21601
  • /2

    $519,000

    • 4 Beds
    • 4 Baths
    • 2,696 Sq Ft

    423 S Washington St, Easton, MD 21601

    DUPLEX. One side currently rented. New roof (architectural shingles) and new heat pump (natural gas).

    rachael harrison Coldwell Banker Realty

    423 S Washington St, Easton, MD 21601
  • /28

    $532,990 New Construction

    • 4 Beds
    • 3 Baths
    • 2,422 Sq Ft

    29885 Londyn Ln, Easton, MD 21601

    Come and see 29885 Londyn Lane in Easton, MD, a new two-story home under construction in Gannon Range. This Azalea home offers four bedrooms, three bathrooms, 9' ceilings, a loft, and a two-car garage. The welcoming foyer has two coat closets and separates to afford privacy to the two spacious guest bedrooms with closets and the secondary bathroom. The open floorplan features a well-designed

    Justin Wood D.R. Horton Realty of Virginia, LLC

    29885 Londyn Ln, Easton, MD 21601
  • /22

    $399,990 New Construction

    • 4 Beds
    • 3 Baths
    • 2,170 Sq Ft

    1684 Lake Placid Dr, Trappe, MD 21673

    This new two-story home showcases a well-planned layout designed for both space and functionality. The main level features an open Great Room, dining area, and kitchen, along with a versatile bedroom that can easily serve as a home office. Upstairs, three additional bedrooms are privately situated around a flexible loft, offering extra living space. The expansive owner’s suite includes a private

    Lennar Builder
    1684 Lake Placid Dr, Trappe, MD 21673
  • /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
  • /19

    $366,540 New Construction

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    1690 Lake Placid Dr, Trappe, MD 21673

    This newly built two-story home offers an expansive open-concept main level, where the kitchen, living, and dining areas come together to create a seamless and flexible living space. Upstairs, two secondary bedrooms and a luxurious owner’s suite are thoughtfully positioned around a versatile loft, ideal for a variety of uses. A two-car garage adds both convenience and functionality to complete

    Lennar Builder
    1690 Lake Placid Dr, Trappe, MD 21673

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