204

Kent County MD Homes for Sale

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  • /24

    $699,000

    • 3 Beds
    • 2.5 Baths
    • 2,185 Sq Ft

    21610 Hidden Creek Dr, Rock Hall, MD 21661

    Enjoy a long, secluded driveway to a 2,185 sq ft home sitting on 7.9 acres of mature, heavily-forested woods with waterfront views of Grey’s Inn Creek. The home features vaulted ceilings and has access to a private pier and dock; it’s perfect for boating, fishing, crabbing, or just enjoying the outdoors. Located in Rock Hall, Maryland, known for hunting, fishing, and Chesapeake Bay boating, this

    Mike Arajakis Whitetail Properties Real Estate, LLC

    21610 Hidden Creek Dr, Rock Hall, MD 21661
  • /24

    $240,000

    • 3 Beds
    • 1 Bath
    • 1,140 Sq Ft

    107 Conley Dr, Chestertown, MD 21620

    Welcome to easy, move in ready living in the heart of Chestertown! This fully renovated townhouse offers modern updates, low maintenance living, and an unbeatable location just minutes from local shops, restaurants, grocery stores, the YMCA, and everything Chestertown has to offer. Step inside to find a beautifully updated interior featuring fresh paint throughout and durable oak luxury vinyl

    Taylor Leaverton Benson & Mangold, LLC

    107 Conley Dr, Chestertown, MD 21620
  • /14

    $375,000

    Coming Soon
    • 4 Beds
    • 2 Baths
    • 1,476 Sq Ft

    1010 Twin Ct, Chestertown, MD 21620

    Adorable 4 bedroom 2 bathroom Cape Cod in the quiet Crestview neighborhood in Chestertown close to Restaurants, Shopping, the brand new YMCA and the Historic Downtown. Eat in kitchen with back deck overlooking a beautiful yard that backs up to farm land that is preserved forever. Freshly painted with new carpet! Washer & dryer in unit. Extra storage in knee walls upstairs. In Chestertown but

    Jason Dey Kevin Dey Realty

    1010 Twin Ct, Chestertown, MD 21620
  • /56

    $289,900

    • 2 Beds
    • 1.5 Baths
    • 1,500 Sq Ft

    21146 Montana Ave, Chestertown, MD 21620

    Escape to the Eastern Shore! Nestled among mature trees on a .41 acre wooded lot, this charming Cape Cod-style home offers the perfect blend of privacy, comfort, and Eastern Shore living. Located in the desirable waterfront community of Tolchester Estates, this home features approximately 1,500 square feet with 2 bedrooms, 1.5 baths, and a spacious loft that can easily serve as a third bedroom,

    Jody Baker Cross Street Realtors LLC

    21146 Montana Ave, Chestertown, MD 21620
  • /30

    $415,000

    Open House 8/08 Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 1,947 Sq Ft

    189 Birchwood Ln, Galena, MD 21635

    Beautifully updated and maintained Colonial home in Dogwood Village. This spacious home offers nearly 2000 square feet of living plus a basement area. There is an attached 2 car garage and both a screened porch and open deck at the rear of the home. A fireplace in the living room adds warmth to cool fall and winter days. The rear of the home is accented by both spacious screened porch and an open

    Steve Parker L. C. Parker Real Estate

    189 Birchwood Ln, Galena, MD 21635
  • /47

    $380,000

    • 3 Beds
    • 1.5 Baths
    • 3,292 Sq Ft

    8312 Broad Neck Rd, Chestertown, MD 21620

    Bring your vision and transform this unique property into the home of your dreams. Situated on 3.79 picturesque acres, the property features a beautiful one-acre stocked pond, offering a peaceful setting with endless possibilities for outdoor enjoyment.A spacious 40' x 60' outbuilding equipped with three-phase electric provides exceptional flexibility for a workshop, home-based business,

    Darrel Reel Pearson Smith Realty, LLC

    8312 Broad Neck Rd, Chestertown, MD 21620
  • /28

    $325,000

    • 3 Beds
    • 2.5 Baths
    • 1,520 Sq Ft

    21128 Striper Run, Rock Hall, MD 21661

    Welcome to 21128 Striper Run, a charming 3-bedroom, 2.5-bath home nestled in the heart of Rock Hall. Offering an exceptional opportunity to own in one of Maryland's most sought-after waterfront communities, this home combines classic charm, quality features, and outstanding value. Step inside to find beautiful real hardwood flooring throughout the main level, creating warmth and character from

    ETHAN HARVEY EXP Realty, LLC

    21128 Striper Run, Rock Hall, MD 21661
  • /74

    $824,900

    Open Sat 11AM - 1PM
    • 5 Beds
    • 3.5 Baths
    • 4,353 Sq Ft

    8999 Orchard Dr, Chestertown, MD 21620

    Welcome to a breathtaking country estate where modern elegance, architectural grandeur, and total sanctuary converge across 2.23 serene acres. Spanning over 4,000 square feet of meticulously refined living space, this extraordinary five-bedroom residence has been thoughtfully crafted to offer both lavish entertaining possibilities and effortless multi-generational comfort.Upon arrival, the

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    8999 Orchard Dr, Chestertown, MD 21620
  • /64

    $740,000

    • 3 Beds
    • 3 Baths
    • 3,388 Sq Ft

    14540 Stirrup Ln, Galena, MD 21635

    Welcome to your Eastern Shore oasis, an impressive nearly 3,700-square-foot home offering river access on almost 2 acres, a boat slip, stunning water views, and beautifully established grounds surrounded by mature trees. Inside, you’ll find a dramatic two-story foyer, hardwood floors, a designer kitchen with granite countertops and an oversized walk-in pantry, multiple living spaces, a

    Luke Schlabach Keller Williams Flagship

    14540 Stirrup Ln, Galena, MD 21635
  • /3

    $300,000

    • Land
    • 4,356 Sq Ft
    • $3,000,000 per Acre

    201 N Lynchburg St, Chestertown, MD 21620

    4 Vacant Lots with many possiblilites. The project has the potential for a density change for 10 or more units. Buyer should do all necessary due diligency. Can also be sold with mls MDKE2006844

    John Ford RE/MAX Associates-Hockessin

    201 N Lynchburg St, Chestertown, MD 21620
  • /5

    $259,900

    Open House 8/08 Coming Soon
    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    6179 Dorlon Dr, Rock Hall, MD 21661

    Coming Soon in Rock Hall! Freshly renovated and ready to welcome you home. This property offers a bright new feel from the moment you step inside. Thoughtful updates and beautiful finishes create an inviting interior, while the spacious yard and mature trees provide plenty of room to enjoy the outdoors. Whether you’re searching for your first home, looking to downsize or low maintenance living,

    Crystal Smith RE/MAX Executive

    6179 Dorlon Dr, Rock Hall, MD 21661
  • /54

    $1,595,000

    • 4 Beds
    • 2 Baths
    • 2,538 Sq Ft

    14046 Tockwogh Ln, Galena, MD 21635

    Enjoy sweeping water views, a bulkheaded shoreline, and a lawn extending to the water's edge—an exceptional and hard-to-find combination. Boating enthusiasts will appreciate the private dock, complete with a boat lift and Jet Ski lift and the location on the river. This charming four-bedroom home blends timeless character with everyday functionality. The thoughtfully designed floor plan features

    Christopher McClary Gunther-McClary Real Estate

    14046 Tockwogh Ln, Galena, MD 21635
  • /10

    $259,900

    New Construction Open Thu 5PM - 7PM
    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    115 Metcalf Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in now. This interior unit features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with

    David Moore Real Broker, LLC

    115 Metcalf Rd, Chestertown, MD 21620
  • /4

    $289,000

    Coming Soon
    • 2 Beds
    • 1.5 Baths
    • 1,386 Sq Ft

    6022 N Main St, Rock Hall, MD 21661

    This charming cottage on the outskirts of town is full of character, thoughtful updates, and endless potential to make it your own. Step inside to find beautiful wide-plank flooring in the living room, creating a warm and welcoming atmosphere. The laundry room and convenient half bath feature brand-new luxury vinyl plank flooring, with the half bath offering enough space to easily add a full-size

    Michele Palmer Doug Ashley Realtors, LLC

    6022 N Main St, Rock Hall, MD 21661
  • /21

    $199,000

    • 2 Beds
    • 1 Bath
    • 1,232 Sq Ft

    21324 Persimmon Dr, Chestertown, MD 21620

    Welcome to this beautifully renovated 2-bedroom, 1-bath townhome offering the perfect blend of comfort, style, and convenience. Completely updated from top to bottom, this move-in-ready home features brand-new luxury vinyl plank flooring, fresh paint throughout, quartz countertops, an updated bathroom, and several new appliances. The fully equipped kitchen opens to a comfortable living and dining

    Taylor Leaverton Benson & Mangold, LLC

    21324 Persimmon Dr, Chestertown, MD 21620
  • /16

    $369,000

    • 3 Beds
    • 2 Baths
    • 1,458 Sq Ft

    20725 Wilkins Ave, Rock Hall, MD 21661

    Charming 3-bedroom, 2-bath rancher situated on a 0.4-acre lot in Ferry Park, just one block from Rock Hall Beach. This 1,458 sq. ft. home features an open-concept kitchen and dining area, creating a bright and inviting space for everyday living and entertaining. Located on a quiet street, yet within walking distance of local restaurants, marinas, and all that downtown Rock Hall has to offer.

    Robin Fithian Rock Hall Properties Real Estate

    20725 Wilkins Ave, Rock Hall, MD 21661
  • /68

    $799,000

    Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 2,857 Sq Ft

    7828 Country Club Ln, Chestertown, MD 21620

    Welcome to this spacious brick rancher located in the desirable Country Club Estates neighborhood, offering over 2,800 square feet of beautifully updated living space in a peaceful, park-like setting. Designed for both comfort and elegance, this home features expansive, light-filled interiors and timeless architectural details throughout. The heart of the home is a large, luxurious living room

    Sarah King Cross Street Realtors LLC

    7828 Country Club Ln, Chestertown, MD 21620
  • /34

    $325,000

    • 4 Beds
    • 2 Baths
    • 2,198 Sq Ft

    200 Manor Ave, Chestertown, MD 21620

    A rare opportunity to own a classic two-story split-level home in Chestertown — set on a large, shaded corner lot just a few miles to Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, and only steps to locally loved restaurants and everyday conveniences. This is the kind of home that simply isn't built anymore: classic lines, original details, and

    Liddy Campbell TTR Sotheby's International Realty

    200 Manor Ave, Chestertown, MD 21620
  • /19

    $339,900

    • 3 Beds
    • 2 Baths
    • 1,568 Sq Ft

    5925 Williams St, Rock Hall, MD 21661

    Welcome to this charming 3-bedroom, 2-bath rancher in the heart of Rock Hall! Freshly painted and move-in ready, this well-maintained home offers comfortable one-level living with a spacious and functional layout. The attached 2-car garage provides plenty of room for parking, storage, or a workshop. Whether you're looking for a year-round residence, a weekend retreat, or a place to enjoy

    Gina Gargeu Century 21 Downtown

    5925 Williams St, Rock Hall, MD 21661
  • /10

    $264,900

    New Construction
    • 3 Beds
    • 1.5 Baths

    121 Metcalf Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized bedrooms including a large primary suite with walk-in

    David Moore Real Broker, LLC

    121 Metcalf Rd, Chestertown, MD 21620
  • /2

    $60,000

    • Land
    • 26,571 Sq Ft
    • $98,361 per Acre

    305 Roosevelt Dr, Chestertown, MD 21620

    Nice cleared building lot in an established community. Public water and sewer available. Property recently acquired through tax sale foreclosure, recording is in process. Law Firm of Shaw and Crowson P.A. in Salisbury preferred for settlement.

    Agent Photo

    Joe Howerton

    Taylor Properties

    305 Roosevelt Dr, Chestertown, MD 21620
  • /28

    $90,000

    $35K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft

    10540 Worton Rd, Worton, MD 21678

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/4/2026, 10:00 AM. Bidding ends 8/6/2026, 1:00 PM. The list price is the suggested opening bid. Deposit: $15,000. This auction takes place on the Ashland Auction Group Website Bidding Platform. Pre-auction offers may be accepted. Located along Maryland’s Eastern Shore in Kent County,

    Adam Shpritz Ashland Auction Group LLC

    10540 Worton Rd, Worton, MD 21678
  • /43

    $100,000

    $25K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,896 Sq Ft

    10520 Worton Rd, Worton, MD 21678

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/4/2026, 10:00 AM. Bidding ends 8/6/2026, 12:50 PM. The list price is the suggested opening bid. Deposit: $15,000. This auction takes place on the Ashland Auction Group Website Bidding Platform. Pre-auction offers may be accepted. Located along Maryland’s Eastern Shore in Kent County,

    Adam Shpritz Ashland Auction Group LLC

    10520 Worton Rd, Worton, MD 21678
  • /31

    $449,000

    Open Sat 1PM - 3PM
    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    21120 Green Ln, Rock Hall, MD 21661

    BACK ON THE MARKET - DUE TO NO FAULT OF THE SELLER! COMING SOON - NEW ROOF!!! Your Chesapeake Bay getaway just steps from Haven Harbour South Marina. Launch your boat, dine on the waterfront, stroll to the beach, and enjoy resort-style living from this beautifully updated home. This updated 3-bedroom, 2-bath rancher situated on an expansive lot with glimpses of the water and room to relax,

    Laurie Renshaw Coldwell Banker Chesapeake Real Estate Company

    21120 Green Ln, Rock Hall, MD 21661
  • /35

    $565,000

    • 3 Beds
    • 2.5 Baths
    • 2,187 Sq Ft

    25124 E Kentfield Rd, Worton, MD 21678

    Light-filled home with glowing wood floors, exposed beams, skylights, and open living space. This one-level home is nestled on just under two acres! The expansive yard offers room for many activities and provides scenic views from the home. Inside, the open living space is bright and airy, with skylights, bay windows, and vaulted ceilings with exposed beams. The large kitchen has beautiful

    Julia Hilfiker Gunther-McClary Real Estate

    25124 E Kentfield Rd, Worton, MD 21678
  • /11

    $25,000

    • 672 Sq Ft

    316 Middle St, Millington, MD 21651

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/3/2026, 10:00 AM. Bidding ends 8/5/2026, 12:20 PM. The list price is the suggested opening bid. Deposit: $5,000. This two-story detached house is located in Millington, MD within Kent County. Residents can enjoy the nearby attractions and facilities such as the Waterfront Park, Rob

    Adam Shpritz Ashland Auction Group LLC

    316 Middle St, Millington, MD 21651
  • /36

    $325,000

    • 3 Beds
    • 1.5 Baths
    • 1,840 Sq Ft

    136 N Main St, Galena, MD 21635

    136 N Main St is Coming Soon in Galena! Your next home may be closer than you think. This inviting Colonial combines classic character with thoughtful updates across nearly 1,900 square feet of living space. Inside, you'll find three comfortable bedrooms, one full bath upstairs, a convenient main-level half bath, a bright kitchen with an easy flow into the main living areas, and a dedicated

    Matt Rhine Keller Williams Legacy

    136 N Main St, Galena, MD 21635
  • /7

    $225,000

    • 5,558 Sq Ft

    5804 Downey Ave, Rock Hall, MD 21661

    Unique opportunity to restore and customize the historic former "Rock Hall Shirt Factory!" This 5,558± sq. ft. building is situated on a 0.31± acre in-town lot and offers endless potential for investors, developers, or buyers looking for a one-of-a-kind project. The interior has been framed and studded for rooms, providing a head start on the renovation process while allowing you to complete the

    Cindy Genther Rock Hall Properties Real Estate

    5804 Downey Ave, Rock Hall, MD 21661
  • /26

    $480,000

    • 5 Beds
    • 2 Baths
    • 1,664 Sq Ft

    21251 Chesapeake Ave, Rock Hall, MD 21661

    Beautifully updated while preserving its character, this charming home is ideally located just a short distance from the Rock Hall Harbor and Chesapeake Bay, offering easy access to waterfront dining, boating, and all the coastal charm Rock Hall has to offer.Relax on the spacious front porch, or entertain on the screened porch, complete with electricity and plenty of space for outdoor

    Julia Hilfiker Gunther-McClary Real Estate

    21251 Chesapeake Ave, Rock Hall, MD 21661
  • /42

    $335,000

    Open Sun 11AM - 1PM
    • 3 Beds
    • 2 Baths
    • 1,412 Sq Ft

    10720 Foreston Rd, Chestertown, MD 21620

    Welcome to 10720 Foreston Rd, a charming and inviting home situated in the peaceful surroundings of Chesapeake Landing in Chestertown, MD. 3 bedrooms and 2 full bathrooms with a spacious eat-in kitchen and generous living room provides ample room for comfortable living. Move-in ready condition. Inside, you'll immediately notice the warmth and character of the stunning hardwood floors that flow

    Kathleen Eder Compass

    10720 Foreston Rd, Chestertown, MD 21620
  • /2

    $289,000

    • 1,874 Sq Ft

    31001 Chesterville Bridge Rd, Millington, MD 21651

    Bring your vision to this rare 15-acre property offering privacy, natural beauty, and endless possibilities. Mostly wooded with a picturesque pond, this property is an ideal setting for those seeking a private retreat, recreational getaway, or future homesite. An original structure dating back to 1980 remains on the property and includes a full basement. The condition existing home is believed

    Terri Murray RE/MAX Executive

    31001 Chesterville Bridge Rd, Millington, MD 21651
  • /37

    $140,000

    • 3 Beds
    • 2 Baths
    • 1,424 Sq Ft

    25028 Heather Ln, Worton, MD 21678

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 7/30/2026, 10:00 AM. Bidding ends 8/3/2026, 1:00 PM. The list price is the suggested opening bid. Deposit: $25,000. This auction takes place on the Ashland Auction Group Website Bidding Platform. 1,184± SF ranch-style single family home located in the Knights Landing area of Worton,

    Adam Shpritz Ashland Auction Group LLC

    25028 Heather Ln, Worton, MD 21678
  • /8

    $550,000

    $49K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    5666 Walnut St, Rock Hall, MD 21661

    Rare opportunity to purchase five contiguous parcels totaling 3.765± acres in a prime location near Rock Hall Harbor. Parcel 505 features an older manufactured home situated on approximately 1.27± water-view acres with scenic views of North Point Marina and Rock Hall Harbor. The additional parcels include Parcel 504 (0.853± acres), Parcel 503 (1.04± acres), Parcel 502 (0.258± acres), and Parcel

    Cindy Genther Rock Hall Properties Real Estate

    5666 Walnut St, Rock Hall, MD 21661
  • /28

    $279,900

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,398 Sq Ft

    25003 Heather Ln, Worton, MD 21678

    Welcome to 25003 Heather Ln! This well maintained 3 bedroom, 2 full bath home offers the ease of first floor living in a quiet neighborhood. Inside, you'll find an open concept layout with high ceilings that create a bright, spacious feel, along with modern finishes throughout. Outside, the huge yard provides plenty of room for entertaining, gardening, pets, or simply enjoying the outdoors. Move

    Grace Casella Crown Homes Real Estate

    25003 Heather Ln, Worton, MD 21678
  • /9

    $155,000

    • 3 Beds
    • 1.5 Baths
    • 1,192 Sq Ft

    409 Calvert St, Chestertown, MD 21620

    Affordable opportunity in the heart of downtown Chestertown! This 3-bedroom, 1.5-bath townhome is ideally located just minutes from Washington College, shops, restaurants, parks, and the waterfront. Offering a functional floor plan with spacious living areas, generously sized bedrooms, and a back yard with additional rear parking, this home is ready for its next owner to make it their own. This

    Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    409 Calvert St, Chestertown, MD 21620
  • /25

    $339,900

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,366 Sq Ft

    321 West St, Millington, MD 21651

    321 West Street in Millington, Maryland is now available for you. This lovely 5-year-old home features vinyl siding, three bedrooms and 2 full bathrooms; Inside, you'll find a formal living room, a dining area, and a fully equipped kitchen with stainless steel appliances, along with a nicely sized island that offers additional space for dining. The main level also includes a laundry room with

    Anne Menaquale RE/MAX Associates - Newark

    321 West St, Millington, MD 21651
  • /43

    $885,000

    • 5 Beds
    • 4 Baths
    • 2,639 Sq Ft

    7680 Country Club Ln, Chestertown, MD 21620

    Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natural light! Enjoy time on the large screened porch, finished with Ipe hardwood, overlooking the peaceful creek, woods and park like setting. Five bedrooms and 4 full bathrooms, nicely designed with privacy in mind. There's an

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    7680 Country Club Ln, Chestertown, MD 21620
  • /28

    $435,000

    • 3 Beds
    • 1.5 Baths
    • 1,160 Sq Ft

    31923 River Park Rd, Millington, MD 21651

    Charming waterfront rancher on the Chester River! This move-in ready home features 3 bedrooms, 1.5 baths, and luxury viny plank flooring throughout. Recent upgrades include all-new appliances (2021), a 12' x 20' shed/workshop (2023), and new HVAC and viny siding (2024).Step outside to a spacious deck overlooking the river and your private dock--perfect for fishing, launching kayaks, or

    Wendy Wilson RE/MAX Chesapeake

    31923 River Park Rd, Millington, MD 21651
  • /3

    $750,000

    • Land
    • 41,817 Sq Ft
    • $781,250 per Acre

    5738 Beach Rd, Rock Hall, MD 21661

    Imagine building your dream luxury waterfront home on one of the most spectacular homesites the Chesapeake Bay has to offer. This exceptional waterfront lot boasts breathtaking panoramic views stretching across the Chesapeake Bay to the iconic Bay Bridge and the distant Baltimore skyline, creating an ever-changing backdrop of stunning sunrises, sailboats, and shimmering waterfront

    Agent Photo

    Anthony Borleis

    RE/MAX Point Realty

    5738 Beach Rd, Rock Hall, MD 21661
  • /20

    $344,000

    • 3 Beds
    • 1.5 Baths
    • 1,216 Sq Ft

    9126 Fairlee Rd, Chestertown, MD 21620

    Looking for peaceful country living? The search is over! Nestled on 1.66 acres, this beautifully renovated 3-bedroom, 1.5-bath home offers the perfect blend of comfort, functionality, and privacy with NO HOA! In addition, there's a versatile bonus/flex room that is ideal for a home office, hobby area, or even a potential 4th bedroom to suit your needs - all on the convenience of one-level living.

    Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    9126 Fairlee Rd, Chestertown, MD 21620

Showing Results 1 - 40, Page 1 of 6

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