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Kent County MD Homes for Sale

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  • /135

    $487,000

    $62K PRICE INCREASE
    • 3 Beds
    • 2.5 Baths
    • 1,948 Sq Ft

    16 Howell Point Rd, Betterton, MD 21610

    Seller is super motivated and may have found their next home so this must go! All offers welcomed! Home recently appraised for $501,000.Welcome to 16 Howell Point Road in Betterton, Maryland, where small-town Eastern Shore charm meets comfortable living just a few blocks from beautiful Betterton Beach!This inviting 3-bedroom, 3-bath home offers plenty of space inside and out. The

    Agent Photo

    Kristina Hyland

    Coldwell Banker Chesapeake Real Estate Company

    16 Howell Point Rd, Betterton, MD 21610
  • /21

    $269,000

    Open Sat 11AM - 1PM $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft

    10540 Tonopah Rd, Chestertown, MD 21620

    Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge master bath, open concept, plenty of closet space, laminate flooring, and a private secluded fenced lot. Located in a water oriented neighborhood with community boat ramp and pier and nearby restaurants and marina. Move here and enjoy all the Eastern Shore has to offer!

    Michele Palmer Doug Ashley Realtors, LLC

    10540 Tonopah Rd, Chestertown, MD 21620
  • /45

    $424,900

    $20K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 1,936 Sq Ft

    8630 Elm Rd, Chestertown, MD 21620

    Located in a beautiful waterfront community, this refreshed 5-bedroom, 2.5-bath home offers approximately 1,936 square feet of comfortable living space on approximately 0.38 acres. The property combines updated interiors, flexible living spaces, and the relaxed lifestyle of Maryland’s Eastern Shore.The home offers five generously sized bedrooms, providing comfortable space for family,

    Lawrence Lessin Save 6, Incorporated

    8630 Elm Rd, Chestertown, MD 21620
  • /37

    $455,000

    $23K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,904 Sq Ft

    7982 Radcliffe Rd, Chestertown, MD 21620

    Welcome home to 7982 Radcliffe Road! This charming corner-lot offers a perfect blend of character and modern comfort. Built in 1978- this well maintained 2 bedroom, 2 bathroom home feels more of a newer era. Inside you'll find a spacious living room with plenty of room to relax by the fireplace or entertain! The oversized garage offers amazing storage and features an office space that is closed

    Abigail Usilton Doug Ashley Realtors, LLC

    7982 Radcliffe Rd, Chestertown, MD 21620
  • /35

    $357,997

    $2K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,208 Sq Ft

    25133 Smithville Rd, Worton, MD 21678

    Welcome to 25133 Smithville Rd.! This spacious 4-bedroom, 3-bath traditional Colonial offers comfortable living with plenty of room to spread out. The main level features a desirable primary suite with a private full bath, along with an inviting eat-in kitchen and formal dining room perfect for everyday living and entertaining.Step outside to enjoy the spacious, level backyard with

    Alyson Anderson Allfirst Realty, Inc.

    25133 Smithville Rd, Worton, MD 21678
  • /9

    $450,000

    • Land
    • 12,477 Sq Ft
    • $1,570,925 per Acre

    0 Cannon St Unit MDKE2006944, Chestertown, MD 21620

    Package offering for two adjacent lots in historic Chestertown. The combined package is for over a quarter of an acre, zoned R-5, within walking distance of downtown Chestertown. The convenient in-town location offers excellent potential for development, with the opportunity to build a single family home, townhouses or apartments. Plans available for proposed townhouses. Backing up to the Rail

    Julie Santoboni Taylor Properties

    0 Cannon St Unit MDKE2006944, Chestertown, MD 21620
  • /9

    $350,000

    • Land
    • 9,380 Sq Ft
    • $1,625,200 per Acre

    0 Cannon St Unit MDKE2006940, Chestertown, MD 21620

    Rare opportunity to own a cleared 9,381 sq. ft, nearly a quarter acre, lot within walking distance of downtown Chestertown. The convenient in-town location offers excellent potential for development, with the opportunity to build a single family home, townhouses or apartments. Plans available for proposed townhouses. Backing up to the Rail Trail, this lot enjoys easy access to local shops,

    Julie Santoboni Taylor Properties

    0 Cannon St Unit MDKE2006940, Chestertown, MD 21620
  • /35

    $585,000

    • 4 Beds
    • 2.5 Baths
    • 2,322 Sq Ft

    12118 Still Pond Creek Rd, Worton, MD 21678

    Welcome to your dream home in Worton, MD! This stunning center hall Colonial-style property boasts 4 bedrooms, 2.5 bathrooms, and sits on over 6 acres of picturesque land. As you approach the home, you'll be greeted by a charming circular driveway and an oversized detached 2 car garage, perfect for storing all your vehicles and outdoor equipment. Inside, the home features beautiful hardwood

    Angela Allen Patterson-Schwartz-Hockessin

    12118 Still Pond Creek Rd, Worton, MD 21678
  • /15

    $480,000

    • 3 Beds
    • 2.5 Baths
    • 3,176 Sq Ft

    129 Trafford Dr, Chestertown, MD 21620

    PICTURES COMING SOON Welcome home to this beautiful 3-bedroom, 2.5-bath residence in the charming town of Chestertown, MD. Designed for both comfortable living and effortless entertaining, this home offers spacious interiors filled with abundant natural light.The main level features a bright kitchen with Breakfast Bar that flows seamlessly into a sunny Florida room, creating the perfect space

    Teresa Queen Elevated Real Estate Solutions

    129 Trafford Dr, Chestertown, MD 21620
  • /9

    $99,999

    • Land
    • 3,096 Sq Ft
    • $1,406,963 per Acre

    620 Cannon St, Chestertown, MD 21620

    Here is your chance to get one of the last vacant lots in downtown Chestertown. And as an added bonus, the lot backs up to the Rail Trail for easy access to the Chester River waterfront and downtown Chestertown. Situated at the corner of Lynchburg and Cannon Streets, this 3,096 sq ft lot can be purchased alone, or along with the recently subdivided adjacent lot. Water and sewer hookups available.

    Julie Santoboni Taylor Properties

    620 Cannon St, Chestertown, MD 21620
  • /26

    $725,000

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

    32745 Hunt Ln, Galena, MD 21635

    Set on a moderate bluff along the upper Sassafras River, this inviting waterfront property offers pristine, natural down river views and exceptional access to the water. Enjoy your private dock, boat lift, and plenty of space for kayaks, paddleboards, and other water toys. The home features three bedrooms plus a walkout basement ready for your vision—ideal for creating additional living space, a

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    32745 Hunt Ln, Galena, MD 21635
  • /33

    $345,000

    $4K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,381 Sq Ft

    5862 N Main St, Rock Hall, MD 21661

    Adorable 3BR/2BA expanded Farm style home located on a spacious lot in the desirable neighborhood of the Town of Rock Hall. Make your way to the country style covered front porch and the door to your forever home. Step inside a home filled with original charm and character throughout offering an abundance of natural light, crown moldings, luxury flooring, and an open main floor plan. The main

    Jordan Larigan LPT Realty, LLC

    5862 N Main St, Rock Hall, MD 21661
  • /53

    $515,000

    • 7 Beds
    • 5 Baths
    • 3,836 Sq Ft

    11960 Flour Mill St, Kennedyville, MD 21645

    Welcome to 11960 Flour Mill Street. This is the perfect house for a growing family or a multi-generational household. Main House has 6 full bedrooms and 4 full bathrooms while the second floor above the garage is a spacious mother-in-law suite with a separate entrance, efficiency kitchen, full bath and walk-in closet. First floor has a bedroom and full bath and wide open floor plan in the kitchen

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    11960 Flour Mill St, Kennedyville, MD 21645
  • /39

    $249,000

    $11K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    6179 Dorlon Dr, Rock Hall, MD 21661

    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, this home is one you’ll

    Crystal Smith RE/MAX Executive

    6179 Dorlon Dr, Rock Hall, MD 21661
  • /35

    $599,900

    $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,920 Sq Ft

    20714 Wilkins Ave, Rock Hall, MD 21661

    Welcome to 20714 Wilkins Avenue, a rare opportunity in the heart of charming Rock Hall. Perfectly positioned less than two blocks from the beach, this home is within walking distance of local favorites including Blue Heron Oyster House, Muskrat Alley Café, and the marinas at Osprey Point and Haven Harbour, making it easy to enjoy everything this beloved Chesapeake Bay town offers.Situated

    Sarah Ulrick Rock Hall Properties Real Estate

    20714 Wilkins Ave, Rock Hall, MD 21661
  • /68

    $799,000

    • 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
  • /25

    $330,000

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

    21352 Allens Ln, Rock Hall, MD 21661

    Adorable arts & craft style home with many upgrades and amenities. The original wood floors are warm and welcoming, wile the custom cabinetry and concrete countertops and sinks add an elegant modern touch. Two plus bedrooms and a custom built sleeping loft provide enough room for occasional guests. Fixed stairs to the attic offer room to expand. The Chesapeake Bay is a short walk to the end of

    Robin Fithian Rock Hall Properties Real Estate

    21352 Allens Ln, Rock Hall, MD 21661
  • /25

    $289,900

    $10K PRICE DROP
    • 6 Beds
    • 1.5 Baths
    • 3,270 Sq Ft

    12733 Still Pond Rd, Still Pond, MD 21667

    Charming historic home offers 6 bedrooms and plenty of space to make your own. Located in the quaint village of Still Pond, it combines timeless character with modern updates and is just a short drive from the Chesapeake Bay and Betterton Beach. A wonderful opportunity to enjoy small-town living in Kent County.

    Daniel Demers Sell Your Home Services

    12733 Still Pond Rd, Still Pond, MD 21667
  • /25

    $375,000

    • 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
  • /24

    $699,000

    • 4 Beds
    • 3 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
  • /74

    $824,900

    • 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
  • /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
  • /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 6PM - 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
  • /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
  • /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
  • /69

    $1,395,000

    • 4 Beds
    • 2.5 Baths
    • 3,626 Sq Ft

    12555 Coopers Ln, Worton, MD 21678

    Beautiful waterfront on nearly 7 acres. Spacious composite deck overlooking Still Pond Creek. Private dock with 3 ft MLW (buyer to verify). Large living room with gleaming hardwood floors and huge sliders looking onto the deck and Still Pond Creek. 2 woodburning fireplaces. Updated kitchen with high-end stainless steel appliances. Laundry room off the kitchen. Steps down to your private

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    12555 Coopers Ln, Worton, MD 21678
  • /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. 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 9/15/2026, 10:00 AM. Bidding ends 9/17/2026, 12:45 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

    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 9/15/2026, 10:00 AM. Bidding ends 9/17/2026, 12:40 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

    Adam Shpritz Ashland Auction Group LLC

    10520 Worton Rd, Worton, MD 21678
  • /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 10/2/2026, 10:00 AM. Bidding ends 10/6/2026, 12:40 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

    Adam Shpritz Ashland Auction Group LLC

    316 Middle St, Millington, MD 21651
  • /7

    $199,000

    $26K PRICE DROP
    • 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
  • /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 9/11/2026, 10:00 AM. Bidding ends 9/15/2026, 11:50 AM. 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

    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
  • /25

    $334,900

    $10K 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

Showing Results 41 - 80, Page 2 of 6

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