157

Kent County MD Homes for Sale

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  • /15

    $150,000

    • Land
    • 1.18 Acres
    • $127,119 per Acre

    Lot 3 Muirfield Dr, Chestertown, MD 21620

    Lot 3 located at the midway point of Fairway #10, a perfect spot to enter the back nine and head to the club house for lunch or dinner (membership required) Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool,

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 331-9489

    Lot 3 Muirfield Dr, Chestertown, MD 21620
  • /28

    $399,000

    • 2 Beds
    • 1 Bath
    • 787 Sq Ft

    117 N Water St Unit 2A, Chestertown, MD 21620

    A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. This unit offers a 2 Bed 1 bath has a brand new kitchen, with island and upgraded bathroom along with up and down river views. Enjoy all the amenities of living waterfront--Community

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 824-5609

    117 N Water St Unit 2A, Chestertown, MD 21620
  • /24

    $299,900

    • 1 Bed
    • 1 Bath
    • 652 Sq Ft

    117 N Water St Unit 3B, Chestertown, MD 21620

    A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 453-1375

    117 N Water St Unit 3B, Chestertown, MD 21620
  • /45

    $334,000

    • 3 Beds
    • 1 Bath
    • 1,104 Sq Ft

    24095 Chestertown Rd, Chestertown, MD 21620

    This gem just outside of Chestertown will be active mid-April. New HVAC, new roof, new flooring and other upgrades! Great living space with a front porch and back patio. Large backyard that overlooks beautiful farm fields. There is a one car detached insulated garage. This home offers close proximity to Rock Hall and all downtown Chestertown amenities, schools, and parks and is only 25 minutes

    Agent Photo

    Lona Todd

    Taylor Properties

    (410) 724-1462

    24095 Chestertown Rd, Chestertown, MD 21620
  • /41

    $579,000 Open Sat 11AM - 2PM

    • 2 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    103 Landing Ln, Chestertown, MD 21620

    Step into this nearly new, impeccably maintained two-bedroom townhouse located in the highly desirable Chester River Landing community. Recent upgrades make this home truly turn-key, perfect for those seeking comfort and style. Relax and entertain all summer long on the beautifully designed screened-in porch, ideal for enjoying warm evenings and gentle breezes.On the second floor, the spacious

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 981-2534

    103 Landing Ln, Chestertown, MD 21620
  • /28

    $725,000

    • 3 Beds
    • 3 Baths

    117 N Water St Unit 1A, Chestertown, MD 21620

    Completely remodeled, this three-bedroom waterfront home boasts a charming front porch and enormous back porch - your private space overlooking the river - along with an enclosed sunroom featuring gorgeous river views through walls of windows. Enjoy abundant outdoor areas and stunning water views from nearly every room. The dock features 3+ feel MLW, with slips available for purchase. This

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 589-6299

    117 N Water St Unit 1A, Chestertown, MD 21620
  • /20

    $212,000

    • Land
    • 1.95 Acres
    • $108,718 per Acre

    Lot 9 Prestwick Dr, Chestertown, MD 21620

    Lot 9 overlooks the 5th hole tee box and the picturesque par 3 water hole # 4. Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 806-9518

    Lot 9 Prestwick Dr, Chestertown, MD 21620
  • /8

    $790,000 New Construction

    • 3 Beds
    • 2.5 Baths

    Lot 3 Muirfield Dr, Chestertown, MD 21620

    Spec home located in small 12 home development (to be built). Prestwick offers the best in eastern shore living with the small town charm of Chestertown, MD, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington, DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or kayak at the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 966-6341

    Lot 3 Muirfield Dr, Chestertown, MD 21620
  • /24

    $950,000 New Construction

    • 3 Beds
    • 3.5 Baths

    228 S Water St, Chestertown, MD 21620

    Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away.

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 230-5332

    228 S Water St, Chestertown, MD 21620
  • /31

    $995,000 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,490 Sq Ft

    230 S Water St Unit 1, Chestertown, MD 21620

    Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away. Available Jan 2025

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 849-6629

    230 S Water St Unit 1, Chestertown, MD 21620
  • /19

    $1,459,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,315 Sq Ft

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620

    Do your investments offer these dividends? A premier waterfront location in a premier condominium community and one of the few remaining to-be-built homes! Enjoy broad water views from this new construction two story, free-standing home which offers all of the sought after amenities of waterfront living including breathtaking sunrises over the Chester River, first floor porch and

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 249-2840

    0 Little Harbor Way Unit 1 MDKE2004992, Chestertown, MD 21620
  • /21

    $998,000 New Construction

    • 3 Beds
    • 3.5 Baths

    226 S Water St, Chestertown, MD 21620

    Newly finished 3 Bedroom townhouses with nearly all the desired attributes of town living, with harbor and marina views and access from the marina on one side and waterfront park on the other. A short walk to downtown shops and restaurants. No short term rental restrictions.

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 376-5375

    226 S Water St, Chestertown, MD 21620
  • /36

    $779,000 Open Sat 11AM - 2PM

    • 3 Beds
    • 3.5 Baths

    212 Landing Ln, Chestertown, MD 21620

    Nestled along the tranquil western shore of the Chester River, this beautiful townhome in Chester River Landing offers an unparalleled waterfront living experience with direct water access and captivating water views. Just a short stroll from the historic heart of Chestertown, MD, it combines modern luxury with timeless charm.This elegant 3-bedroom, 2.5-bath residence is designed to maximize

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 883-7032

    212 Landing Ln, Chestertown, MD 21620
  • /22

    $549,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 2 Baths
    • 1,961 Sq Ft

    101 Birch Run Rd, Chestertown, MD 21620

    A sleek, thoughtfully executed renovation with clean lines and a minimalist aesthetic—sure to impress even the most discerning buyer... Located in Chestertown's coveted Mile Tree Village community, this newly updated 3-bedroom, 2-bath rancher with oversized 2-car garage features a new roof with 50-year shingles and a transferable warranty, new water and sewer lines to the street (2022), EV

    Stacy Kendall Cross Street Realtors LLC

    101 Birch Run Rd, Chestertown, MD 21620
  • /49

    $495,000

    • 4 Beds
    • 3 Baths
    • 2,184 Sq Ft

    28743 Anglewood Rd, Kennedyville, MD 21645

    A MILE FROM ORDINARY. A waterfront Community. Looking for a forever home or a dream retreat? Kentmore Park is a community dating back almost 80 years. Designed to be a place of peace and tranquility along the shores of the Sassafras river. Home of primary residents and part time friends and family. As in CHEERS, everyone knows your name. Come and enjoy. Short distance to the Community beach,

    Patricia Kern Gunther-McClary Real Estate

    28743 Anglewood Rd, Kennedyville, MD 21645
  • /57

    $725,000 Open Sat 11AM - 2PM

    • 2 Beds
    • 2.5 Baths
    • 2,204 Sq Ft

    100 Little Harbor Way, Chestertown, MD 21620

    Welcome to 100 Little Harbor Way, a charming home nestled in the desirable Chestertown community of Chester River Landing. This 2 bedroom, 2 bath home offers the perfect blend of comfort and modern living and is ideal for quiet relaxation and entertaining alike. Situated in a tranquil neighborhood, you'll find yourself within easy reach of local amenities, including parks and trails, the Chester

    Jeannette Westcott Keller Williams Realty Centre

    100 Little Harbor Way, Chestertown, MD 21620
  • /38

    $649,000

    • 3 Beds
    • 2.5 Baths
    • 2,296 Sq Ft

    129 N Queen St, Chestertown, MD 21620

    Welcome to 129 N. Queen Street situated in one of Historic Chestertown's most desirable and sought after locations. Nestled among multiple other restored and renovated residences, this home itself has undergone a tasteful and remarkable transformation. The entire interior has been completely renovated over the past several years utilizing many new modern materials blended with some original

    William Norris Select Land & Homes, LLC

    129 N Queen St, Chestertown, MD 21620
  • /48

    $579,900

    • 1 Bath
    • 1,148 Sq Ft

    5179 Quaker Neck Rd, Chestertown, MD 21620

    A One-of-a-Kind Historic Treasure Reimagined for Modern LivingStep into history with this extraordinary Greek Revival chapel, originally built in 1865 as Walton Chapel and later renamed Mowbray Chapel. Nestled on 3.22 picturesque acres in Chestertown’s serene Quaker Neck community, this stunning brick structure has been thoughtfully restored and modernized, seamlessly blending old-world charm

    Jonathan Taylor Hyatt & Company Real Estate, LLC

    5179 Quaker Neck Rd, Chestertown, MD 21620
  • /72

    $499,000

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft

    1 Bayview Rd, Betterton, MD 21610

    Rigbie Bluff is the perfect maintenance-free community in the quiet waterfront town of Betterton; known as the Jewel of the Chesapeake. Located at the confluence of the Sassafras River and Chesapeake Bay, Betterton got its reputation for its picturesque sunsets and wonderful public beach. Embrace the waterfront lifestyle and so much more without the waterfront taxes. This 3 bedroom, 2 bathroom

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    1 Bayview Rd, Betterton, MD 21610
  • /16

    $374,900

    • 3 Beds
    • 2 Baths
    • 1,464 Sq Ft

    11219 Station Rd, Worton, MD 21678

    This country charmer is the best of all worlds- 1.2 acres out in the country but just minutes away from the historic county seat of Kent County- beautiful Chestertown. There are 3 very spacious bedrooms, 2 baths and a Great Room with vaulted ceilings. The Main Bedroom has a luxurious bathroom with a jetted tub and an enormous walk-in closet. There is new paint and carpet....nothing to do but move

    Scott Saunders Coldwell Banker Waterman Realty

    11219 Station Rd, Worton, MD 21678
  • /34

    $410,000

    • 4 Beds
    • 3 Baths
    • 2,130 Sq Ft

    5311 Elburn Ln, Rock Hall, MD 21661

    Nestled at the end of a quiet road, this beautifully renovated 2,130 sq ft 4-bedroom, 3-bathroom home sits on 1.83 acres, offering a perfect blend of privacy and convenience—just 2 miles from Rock Hall’s dining, shopping, and waterfront attractions. A thoughtful renovation and addition bring modern comfort, featuring an open floor plan, a cozy fireplace, and updated systems, including a new roof

    Robin Fithian Rock Hall Properties Real Estate

    5311 Elburn Ln, Rock Hall, MD 21661
  • /26

    $439,000

    • 4 Beds
    • 2 Baths
    • 1,247 Sq Ft

    21424 Catholic Ave, Rock Hall, MD 21661

    Welcoming to the newly renovated 21424 Catholic Ave! Situated on a large in-town parcel, the largest residential lot on Catholic Ave. Spacious open living space with a beautifully renovated kitchen, custom wood cabinets, new LVT and engineered hardwood flooring. The welcoming living space contains original wood accents, adding much charm to this newly updated home. There are three bedrooms,

    Lynn Hilfiker Gunther-McClary Real Estate

    21424 Catholic Ave, Rock Hall, MD 21661
  • /25

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,326 Sq Ft

    5686 S Main St, Rock Hall, MD 21661

    Sweet corner property in downtown Rock Hall, right on the "parade route," and just two blocks from the Rock Hall Harbor/ Chesapeake Bay. Welcoming home with a first floor primary bedroom, and large living room with a woodstove. There is a formal dining room, or you could enjoy meals outside in the fenced in back yard! Upstairs offers two more bedrooms, a full bath and an additional room, perfect

    Lynn Hilfiker Gunther-McClary Real Estate

    5686 S Main St, Rock Hall, MD 21661
  • /29

    $375,000

    • 3 Beds
    • 1.5 Baths
    • 1,731 Sq Ft

    21201 Rock Hall Ave, Rock Hall, MD 21661

    This quintessential classic Rock Hall home has loads of nostalgic appeal. Comfortably appointed and currently used as a vacation rental, being sold turn-key. Located in the heart of Rock Hall - walk, bike, or take the shuttle to multiple attractions, including restaurants, shops, marinas, a performing arts venue, and Rock Hall's sweet beach. This would make a fantastic second home, and yet cozy

    Lynn Hilfiker Gunther-McClary Real Estate

    21201 Rock Hall Ave, Rock Hall, MD 21661
  • /2

    $150,000

    • Land
    • 2.00 Acres
    • $75,000 per Acre

    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620

    Beautiful 2-Acre Lot – Build Your Dream Home!Come and experience the charm of this picturesque 2-acre lot, perfectly priced and ready for your dream home. Nestled among scenic farms and mature trees, this serene setting offers the perfect blend of privacy and natural beauty.Located just minutes from the water, you'll enjoy easy access to nearby Tolchester Beach—only about 2 miles west—and the

    Sebrin Adem RE/MAX Allegiance

    0 Georgetown Rd SE Unit MDKE2005076, Chestertown, MD 21620
  • /3

    $7,500

    • Land
    • 0.86 Acre
    • $8,721 per Acre

    0 Medders Rd, Still Pond, MD 21667

    Priced to sell! 0.86 acres of non-buildable, recreational land in the quaint town of Still Pond, MD. Just down the road from Betterton beach and boat ramp. The neighboring lot is also for sale MDKE2004176 so you could buy two lots next door to each other. Buyer responsible for due diligence.

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Medders Rd, Still Pond, MD 21667
  • /10

    $99,900

    • 2 Beds
    • 1 Bath
    • 910 Sq Ft

    132 Prospect St, Chestertown, MD 21620

    Priced To Sell Fast! Renovate & Resell or Buy & Hold, Desirable 2 Level Colonial, Spacious Kitchen, Spacious Bedrooms, Covered Front Porch, Much More!! Just Waiting For Your Personal Cosmetics and Renovations to Make it Shine. Close to Schools, Shopping and Commuter Routes. This Will Not Last! Sold As-Is.

    Matthew Altizer ANR Realty, LLC

    132 Prospect St, Chestertown, MD 21620
  • /32

    $865,000 Open Sat 12PM - 2PM

    • 2 Beds
    • 2 Baths
    • 1,966 Sq Ft

    26889 Morgnec Rd, Chestertown, MD 21620

    This waterfront farmette is a rare find just a few minutes from downtown Chestertown and features extensive updating. The new kitchen, 2 new full bathrooms, and new roof all from 2024 just to name a few have you set up for many years to come. Most of the property is cleared and grassy making it perfect for your equestrian retreat on the water. A detached 2 car garage is perfect for vehicles or

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    26889 Morgnec Rd, Chestertown, MD 21620
  • /22

    $277,000 Open Sun 1:30PM - 3PM

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    25241 Porters Grove Rd, Worton, MD 21678

    Move right in and make yourself at home! Located just a stones throw from Worton Park, Kent County Community Center and Kent County High School, this 3 bedroom 1 bathroom home has been updated, well maintained and nicely landscaped. The property is on town water and sewer and is .87 acres comprised of 3 lots zoned village. There are sewer allocations available in the area so subdivision may be

    Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    25241 Porters Grove Rd, Worton, MD 21678
  • /23

    $289,000

    • 3 Beds
    • 2 Baths
    • 1,062 Sq Ft

    314 Cypress St, Millington, MD 21651

    Welcome to Millington. This home features 3 bedrooms and 2 full baths, a screened in porch, and oversized detached garage. The primary hosts an en-suite. The kitchen has good space and can be an eat in, double wall ovens for all that extra cooking. A laundry room is conveniently off the kitchen with a separate entrance outside where you will find a charging station for an electric car. A spacious

    Sue Bisbee Village Real Estate Company LLC

    314 Cypress St, Millington, MD 21651
  • /3

    $15,000

    • Land
    • 0.69 Acre
    • $21,739 per Acre

    23683 L Rd, Chestertown, MD 21620

    This wooded property offers a peaceful, rural setting while still being close to local amenities and waterfront attractions just minutes from the town of Chestertown, Worton Creek Marina, and Great Oak Landing.

    Alyson Anderson Allfirst Realty, Inc.

    23683 L Rd, Chestertown, MD 21620
  • /24

    $309,000

    • 4 Beds
    • 2 Baths
    • 1,000 Sq Ft

    6374 Rock Hall Rd, Rock Hall, MD 21661

    Looking for your first place or a weekend stay to enjoy Marylands beautiful eastern shore, look no more! Located just outside of Rock Hall, this charming ranch-style residence offers the convenience of one-level living, perfectly situated on a spacious, treed lot just minutes from downtown. Recently remodeled from top to bottom, this home features sleek stainless steel appliances, stunning

    Dee Dee Miller Long & Foster Real Estate, Inc.

    6374 Rock Hall Rd, Rock Hall, MD 21661
  • /87

    $1,200,000

    • 5 Beds
    • 6 Baths
    • 3,078 Sq Ft

    22153 1st Point Rd, Chestertown, MD 21620

    Experience the waterfront lifestyle like never before in this stunning mid-century modern home, which seamlessly hangs cliffside over the serene waters of the Chesapeake Bay's Fairlee Creek. Offering unparalleled privacy and exclusivity, this extraordinary residence evokes the sensation of floating on a boat, where every moment feels like an escape to a tranquil paradise. The unique design and

    Liddy Campbell TTR Sotheby's International Realty

    22153 1st Point Rd, Chestertown, MD 21620
  • /70

    $945,000

    • 8 Beds
    • 5.5 Baths
    • 6,215 Sq Ft

    5961 Rock Hall Rd, Rock Hall, MD 21661

    Exceptional Multi-Generational Estate This one of kind property, built in 2015, offers an extraordinary opportunity for multi-generational living, guest accommodations, or an income-producing residence. Encompassing over 6,000+ square feet, this estate includes two distinct homes connected with a 2 car garage and designed to provide both privacy and convenience. Situated on the front of

    Joelle Dolch Cross Street Realtors LLC

    5961 Rock Hall Rd, Rock Hall, MD 21661
  • /32

    $364,900

    • 3 Beds
    • 2.5 Baths
    • 1,724 Sq Ft

    216 Silver Heel Rd, Chestertown, MD 21620

    Welcome to this move-in ready home, situated on a premium corner lot in The Village at Chestertown! This charming 1,742 square foot, two-story home offers the perfect blend of comfort and style. The inviting front porch is an ideal spot to unwind with your morning coffee, enjoy the view of the open fields, and watch the clouds drift by.Inside, the well-designed layout begins with a foyer and

    Cynthia Gardner CENTURY 21 New Millennium

    216 Silver Heel Rd, Chestertown, MD 21620
  • /46

    $300,000

    • 3 Beds
    • 2 Baths
    • 1,374 Sq Ft

    21314 Haven Rd, Rock Hall, MD 21661

    Welcome to this beautifully updated 3-bedroom, 2-bath rancher in the heart of Rock Hall, Maryland! Renovated in 2020, this home shines with modern updates while maintaining its cozy charm. The spacious floor plan is filled with natural light, enhanced by large windows and a lovely sunroom—perfect for enjoying your morning coffee or unwinding in the evening. The updated kitchen features

    Jeremey Weiss Keller Williams Flagship

    21314 Haven Rd, Rock Hall, MD 21661
  • /3

    $210,000

    • Land
    • 3.96 Acres
    • $53,030 per Acre

    14134 Cornus Ct, Galena, MD 21635

    Welcome to Gentle Winds! Nestled in a serene and pristine neighborhood near the Sassafras River, this nearly 4-acre parcel of vacant residential land offers the perfect opportunity to build your dream home in a tranquil rural setting. Surrounded by lush greenery and natural beauty, this property provides ample space for both privacy and outdoor activities. Plus, no builder tie, making your dream

    Kim Simpson Thyme Real Estate Co LLC

    14134 Cornus Ct, Galena, MD 21635
  • /68

    $1,650,000

    • 5 Beds
    • 3 Baths
    • 3,317 Sq Ft

    6581 Elizabeths Ln, Rock Hall, MD 21661

    Private Eastern Shore Waterfront RetreatTucked away on a serene, wooded 5-acre waterfront peninsula, 6581 Elizabeth’s Lane offers an unparalleled private escape on West Fork Langford Creek, feeding into the Chester River. With over 1,000 feet of deep water shoreline and three sides of water frontage, this secluded retreat provides easy access by boat to Rock Hall, Kent Island, Annapolis,

    Carol Snyder Monument Sotheby's International Realty

    6581 Elizabeths Ln, Rock Hall, MD 21661
  • /47

    $229,000

    • 3 Beds
    • 3 Baths
    • 2,050 Sq Ft

    14 3rd Ave, Betterton, MD 21610

    A home finished your way with what could be over 3,078 square feet of living space! Complete your new Victorian style home with the finishes & colors you enjoy! Located within a .3 mile walk to Betterton Beach and the Town Dock! Public showers, rest rooms and transient boat slips are all at your disposal! The interior of the home is a blank slate and has been protected from the elements. The

    Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    14 3rd Ave, Betterton, MD 21610
  • /20

    $235,000 Open House 5/03

    • 3 Beds
    • 2.5 Baths
    • 1,200 Sq Ft

    300 Hilltop Ln, Chestertown, MD 21620

    Welcome to this beautifully updated end-unit townhouse in the heart of Chestertown! Featuring 3 bedrooms and 2.5 bathrooms, this home is fresh, bright, and ready for you to move right in. The kitchen shines with freshly painted cabinets and brand-new appliances, while new flooring throughout adds a modern touch.Enjoy the convenience of a patio out back—perfect for relaxing or entertaining.

    William Sutton Coldwell Banker Chesapeake Real Estate Company

    300 Hilltop Ln, Chestertown, MD 21620

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