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Chester, MD Homes for Sale

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  • /38

    $495,000

    • 3 Beds
    • 2 Baths
    • 1,804 Sq Ft

    1848 Harbor Dr, Chester, MD 21619

    Don’t miss this charming Cape Cod-style home in the highly desirable Harbor View neighborhood of Chester. Thoughtfully designed and move-in ready, this home offers the perfect blend of comfort, style, and functionality. The main level features luxury vinyl plank flooring and a bright, open-concept layout ideal for everyday living and entertaining. The spacious kitchen boasts granite countertops,

    Colleen Smith EXP Realty, LLC

    1848 Harbor Dr, Chester, MD 21619
  • /7

    $230,000

    • Land
    • 1.68 Acres
    • $136,905 per Acre

    0 Newtown Rd, Chester, MD 21619

    ***Recent development, there is an expired Perk with the county. Buyer must verify and renew with the county health dept!!!*** Looking for peace and serenity, look no further! You won't find a better opportunity on the eastern shore, total of just over 1.10 acres (per the tax record)! This acreage is a total of 2 tax ID numbers being sold as a package. Buyer to verify perc, well, engineering,

    Rob Carter Douglas Realty, LLC

    0 Newtown Rd, Chester, MD 21619
  • /21

    $349,900

    • 1 Bed
    • 1 Bath
    • 724 Sq Ft

    34 Queen Anne Way Unit F, Chester, MD 21619

    Rare Opportunity in Queen’s Landing with Stunning Chester River Views Welcome to one of the few oversized one-bedroom condos in the highly desirable Queen’s Landing community. Immaculately maintained and thoughtfully designed, this larger-than-average unit offers gorgeous views of the Chester River and the added benefit of expanded living space rarely found in one-bedroom layouts. The larger

    Joelle Dolch Cross Street Realtors LLC

    34 Queen Anne Way Unit F, Chester, MD 21619
  • /20

    $299,500

    • 2 Beds
    • 2 Baths
    • 1,069 Sq Ft

    114 Merganser Ct, Chester, MD 21619

    Nestled in the charming Bayside Marina community, this 2nd floor condo offers a perfect blend of comfort and modern living. Built in 1999, this contemporary gem features an open floor plan that seamlessly connects the living with vaulted ceilings, dining, and kitchen areas, creating an inviting space for relaxation and entertaining. The kitchen boasts ENERGY STAR appliances, including a

    Beverly Sloane Benson & Mangold, LLC

    114 Merganser Ct, Chester, MD 21619
  • /2

    $19,500

    • 2 Beds
    • 1 Bath
    • 764 Sq Ft

    1405 Little Creek Rd, Chester, MD 21619

    This property, situated on a 0.17-acre lot, offers a blank canvas for your vision. Located in Queen Anne's County, the existing structure presents endless possibilities for the right buyer. Take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details.Please note that

    Dustin Parker The Parker Group

    1405 Little Creek Rd, Chester, MD 21619
  • /64

    $550,000

    • 3 Beds
    • 3.5 Baths
    • 2,100 Sq Ft

    200 Schooner Way, Chester, MD 21619

    Just minutes over the Chesapeake Bay Bridge, this beautifully maintained end-unit townhome in Bayside offers the perfect Eastern Shore escape. Spectacular water views overlooking Castle Harbor Marina, the home features multiple decks, updated finishes, and, if you choose Castle Harbor Marina, easy access to your boat slip, only steps away. With approximately 2,100 square feet on three finished

    Michele Cordle Long & Foster Real Estate, Inc.

    200 Schooner Way, Chester, MD 21619
  • /52

    $549,000

    • 2 Beds
    • 2.5 Baths
    • 1,586 Sq Ft

    34 Queen Anne Way, Chester, MD 21619

    Open House Saturday April 4th 12:15- 1:30. Fully Remodeled Chester River Waterfront Condo! This gem won't last long! Beautifully renovated 2BR/2.5BA waterfront condominium located in the sought-after Queen’s Landing resort-style community on the scenic Chester River, just off the Chesapeake Bay. This move-in-ready home showcases a stunning top-to-bottom remodel, including new luxury vinyl plank

    Lona Todd Taylor Properties

    34 Queen Anne Way, Chester, MD 21619
  • /13

    $649,990 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    102 Boatswain Way Unit 11, Chester, MD 21619

    Open home office just off the main living space. Gourmet kitchen with central island for everyday cooking & gathering. Dining area with dry bar for easy entertaining. Electric fireplace adds warmth to the great room. Patio connects seamlessly to the great room & owner’s suite. Owner’s suite with dual closets for added storage. Owner’s bath with dual sinks & glass shower enclosure. Bedroom 2 with

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 11, Chester, MD 21619
  • /20

    $889,990 New Construction

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

    102 Boatswain Way Unit 21, Chester, MD 21619

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

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 21, Chester, MD 21619
  • /30

    $247,000

    • 1 Bed
    • 1 Bath
    • 724 Sq Ft

    8F Queen Victoria Way, Chester, MD 21619

    Queens Landing - One bedroom condo with living room overlooking kitchen, good for entertaining. Private patio off bedroom with secured storage. Laundry is stackable located in bedroom. You will enjoy the Queen's Landing community clubhouse, marina, tennis court and pool and well as the trails in the community.Call today for your private showing.

    Linda Austin Long & Foster Real Estate, Inc.

    8F Queen Victoria Way, Chester, MD 21619
  • /68

    $599,000

    • 2 Beds
    • 2.5 Baths
    • 1,425 Sq Ft

    29A Queen Mary Ct, Chester, MD 21619

    Experience "Paradise" in Queen’s Landing. This rare, end-unit waterfront gem offers an unparalleled livingexperience overlooking the serene Lake Amleto. Boasting a 2019 full-gut renovation by a customcontractor, this 1,425 sq. ft. residence (including a 145 sq. ft. sunroom) blends sophisticated design withresort-style tranquility. The interior showcases master-level craftsmanship:

    Jorge Zea Jorge A. Zea

    29A Queen Mary Ct, Chester, MD 21619
  • /50

    $445,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 2.5 Baths
    • 1,296 Sq Ft

    200 Newtown Rd, Chester, MD 21619

    Buyer's Financing Fell Through - No Fault of the home or seller! Welcome to 200 Newtown Road, a charming home perfectly suited for those looking to enjoy Eastern Shore living. The inviting front porch offers the perfect spot to relax and unwind, while the screened porch provides additional space to enjoy the outdoors in comfort. Inside, you’ll find a generously sized kitchen with room for a table

    Kathleen Higginbotham Samson Properties

    200 Newtown Rd, Chester, MD 21619
  • /56

    $488,000

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

    1000 Herons Nest Way Unit 22, Chester, MD 21619

    BACK on the MARKET. GREAT OPPORTUNITY at THIS PRICE.This Chester model has scenic, seasonal views of Macum Creek, beautiful sunrises, and an incredible display of wildlife in all seasons. Easy walk to Kayak launch and creek. With nearly 2000 square feet of open living space this home has a great layout for entertaining family and friends. The spacious great room, adjacent to the dining area

    Ralph Kennedy RE/MAX Executive

    1000 Herons Nest Way Unit 22, Chester, MD 21619
  • /54

    $599,000

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

    1000 Herons Nest Way Unit 402, Chester, MD 21619

    Rarely on the market Penthouse level Chester model available immediately! Balcony views from the top floor leftside provide view of the Chester River, Macum Creek and the Community Kayak's. Located within the serene and vibrant community of Four Seasons at Kent Island, this exquisite 2-bedroom, 2.5 bath Built in 2020, this elegant unit combines modern design with high-end finishes, creating a

    Dan Judge RE/MAX United Real Estate

    1000 Herons Nest Way Unit 402, Chester, MD 21619
  • /40

    $339,000

    • 2 Beds
    • 2.5 Baths
    • 1,280 Sq Ft

    54H Queen Caroline Ct, Chester, MD 21619

    OPEN HOUSE...Sunday, May 3rd, 11:30-1:30!! Owners have lowered the price by $10,000 and are willing to look at offers! Nothing to do but move in! Be in this spring to enjoy all that summer offers on the shore!! This roomy 2 bedroom, 2.5 bathroom end unit has been completely painted in a beautiful neutral shade and has new carpet throughout the living areas and new vinyl flooring in the kitchen. A

    Mary Stevens Long & Foster Real Estate, Inc.

    54H Queen Caroline Ct, Chester, MD 21619
  • /44

    $889,990 New Construction

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

    102 Warbler Way Unit 2921, Chester, MD 21619

    Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting

    Mary Anne Kowalewski KOVO Realty

    102 Warbler Way Unit 2921, Chester, MD 21619
  • /74

    $799,900

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    132 Wheelhouse Way Unit 11, Chester, MD 21619

    Experience refined coastal living at 132 Wheelhouse Way #11, where the highly desirable Magothy floor plan offers sweeping water views and an unparalleled setting just steps from the clubhouse and Eastern Shore-inspired amenities. Perfectly positioned in one of the community’s most sought-after buildings, this residence has been meticulously maintained and reflects true pride of ownership

    Veronica Lawson Real Broker, LLC

    132 Wheelhouse Way Unit 11, Chester, MD 21619
  • /2

    $369,900 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    54 D Queen Caroline Ct, Chester, MD 21619

    Rare opportunity to own a 3-bedroom, 2.5-bath condo in the highly sought-after Queen’s Landing community! Beautifully updated and move-in ready, this spacious unit features fresh paint, a thoughtfully designed layout, and a stylish kitchen with quartz countertops that opens to comfortable living and dining spaces—perfect for everyday living and entertaining. Enjoy the lifestyle everyone wants

    Michelle DiDonato Island Realty, LLC

    54 D Queen Caroline Ct, Chester, MD 21619
  • /34

    $949,990 New Construction

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

    102 Boatswain Way Unit 42, Chester, MD 21619

    Home office with lighted French doors creates a private workspace. Gourmet kitchen with spacious central island anchors the layout. Dining area with dry bar keeps entertaining within easy reach. Great room with electric fireplace draws the space together. Balcony just off the great room offers easy outdoor access. Owner’s suite also connects to the balcony for a private outdoor retreat. Owner’s

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 42, Chester, MD 21619
  • /13

    $701,990 New Construction

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

    Simone Plan at K. Hovnanian’s® Four Seasons at Kent Island - 35' River Series, Chester, MD 21619

    Private bedroom 2 located off foyer for overnight guests. Striking kitchen with large island and plenty of counter space. Open and airy great room with slider to covered patio. Convenient covered patio with screened patio option. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with split vanities. Versatile loft on second floor with 2 secondary bedrooms and full bath.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36464519, Chester, MD 21619
  • /24

    $1,400,000 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,930 Sq Ft

    117 Flycatcher Way, Chester, MD 21619

    Formal dining room off the foyer for hosting celebrations. Breathtaking kitchen with stacked grey cabinetry & glass uppers. Sprawling quartz island perfect for prep & dining. Vaulted ceiling with ceiling beams connects dining area and great room. Elegant fireplace and sliding door to screened patio in great room. Private home office for working remotely. Primary suite & bath with dual vanities

    K. Hovnanian Homes Builder
    117 Flycatcher Way, Chester, MD 21619
  • /44

    $649,900

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

    200 Harrier Way Unit 21, Chester, MD 21619

    Welcome to Luxury Condo Living at The Four Seasons at Kent Island, An active 55+ Community packed with tons of amenities . Move -in to this turn key luxury condo with plenty of natural light with "Perfect Fit" planation shutters and ample privacy on all windows and doors. The kitchen has a gourmet package including quartz countertops and a large island with space for barstool eating, subway tile

    shannon Gompers Long & Foster Real Estate, Inc.

    200 Harrier Way Unit 21, Chester, MD 21619
  • /32

    $434,900

    • 3 Beds
    • 4 Baths
    • 1,899 Sq Ft

    208 Blenny Ln Unit 100, Chester, MD 21619

    PRICE REDUCTION! Just like NEW! Welcome Home to this beautifully upgraded 4BR END UNIT Townhome with 2 full and 2 half baths, thoughtfully refreshed from top to bottom! Step inside to find the main level that boasts new carpet and new LVP flooring, a new half bath, new paint, a spacious laundry room and a large bedroom that could be used as another family room, toy/game room, den space, home

    Pamela Ackermann-Doll RE/MAX Executive

    208 Blenny Ln Unit 100, Chester, MD 21619
  • /21

    $1,139,990 New Construction

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

    102 Boatswain Way Unit 41, Chester, MD 21619

    Stylish gourmet kitchen centered around a large island. Dining space with convenient dry bar keeps hosting within easy reach. Open great room with electric fireplace anchors the main living area. Balcony extends directly from the living space for easy outdoor access. Owner’s suite with two spacious walk-in closets offers room to spread out. Private sitting area in the owner’s suite connects to

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 41, Chester, MD 21619
  • /73

    $712,000 Open Sat 12PM - 2PM

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

    266 Peregrine Dr, Stevensville, MD 21666

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

    Edward Beres RE/MAX Executive

    266 Peregrine Dr, Stevensville, MD 21666
  • /27

    $439,900

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    1340 Queen Anne Dr, Chester, MD 21619

    PRICE Improvement...Discover the charm of this fully updated ranch in a serene, water-privileged community! With a spacious yard and an inviting open floor plan, this home features a stunning new kitchen complete with a large white granite island, sleek white cabinets, and stainless steel appliances. Sunlight floods the dining area through new sliding doors, while the generous living room is

    Darlene Winegardner RE/MAX Executive

    1340 Queen Anne Dr, Chester, MD 21619
  • /41

    $474,900

    • 4 Beds
    • 2 Baths
    • 1,750 Sq Ft

    1906 Harbor Dr, Chester, MD 21619

    *PRICE IMPROVEMENT!* Welcome to this beautifully renovated ranch-style home offering 4 bedrooms, 2 full bathrooms, and a spacious open floor plan designed for modern living. Completely remodeled from top to bottom, this move-in ready property combines style, comfort, and functionality in every detail. The stunning kitchen features sleek quartz countertops, stainless steel appliances, and a large

    Gregory Bennett Jr. Five Star Real Estate

    1906 Harbor Dr, Chester, MD 21619
  • /102

    $529,900

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

    111 Marshgrass Way Unit 22, Chester, MD 21619

    Rare resale condo, turnkey! Your dream retreat awaits in this stunning luxury condo, where modern elegance meets breathtaking natural beauty. This exquisite residence features two spacious bedrooms, each with its own en-suite bath, and an additional half bath for guests. The thoughtfully designed office boasts custom built-in cabinets, providing both functionality and style.--Step into the heart

    Sharon Blaszczak Long & Foster Real Estate, Inc.

    111 Marshgrass Way Unit 22, Chester, MD 21619
  • /52

    $849,990 New Construction

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

    102 Boatswain Way Unit 2933, Chester, MD 21619

    Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office

    Mary Anne Kowalewski KOVO Realty

    102 Boatswain Way Unit 2933, Chester, MD 21619
  • /49

    $464,000 Open Sat 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 2,016 Sq Ft

    1906 Stevens Dr, Chester, MD 21619

    Spacious and beautifully updated ranch-style home offering over 2,000 square feet of comfortable one-level living. This versatile layout features 3 bedrooms and 2 full baths, including a large bonus room that can easily function as a fourth bedroom, home office, or second living area. A welcoming front porch sets the tone, while the screened back porch provides the perfect space to relax or

    Terri Murray RE/MAX Executive

    1906 Stevens Dr, Chester, MD 21619
  • /13

    $649,990 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    102 Boatswain Way Unit 12, Chester, MD 21619

    Open home office for flexible work or study. Gourmet kitchen with central island at the heart of the home. Dining area with dry bar for easy entertaining. Great room with electric fireplace for a cozy focal point. Patio off the great room with direct access to the owner's suite. Owner's suite with dual closets for added storage. Owner's bath with dual sinks & glass shower enclosure. Bedroom 2

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 12, Chester, MD 21619
  • /64

    $1,167,890 New Construction

    • 4 Beds
    • 3.5 Baths

    1757 Harbor Dr, Chester, MD 21619

    *****Immediate Delivery*****WATERFRONT DEEP WATER ****Schedule showoing today! The Blue Heron is a new home design offered by Lacrosse Homes. The single family design features now one but TWO decks -- one from the second floor great room and the second from the third level primary bedroom suite. Take in all the beautiful sights and sounds of a Coastal Maryland lifestyle in this home built for

    George Bailey Keller Williams Flagship

    1757 Harbor Dr, Chester, MD 21619
  • /40

    $475,000

    • 3 Beds
    • 2.5 Baths
    • 1,728 Sq Ft

    1916 Stevens Dr, Chester, MD 21619

    Now offered at a new and improved price, this beautifully updated and meticulously maintained home delivers exceptional value in the highly desirable Harbor View community—just two miles east of the Chesapeake Bay Bridge. Set on a picturesque 0.35‐acre corner lot, this 3‐bedroom, 2 full and 1 half bath home blends comfort, quality, and an unbeatable location.Inside, you’ll love the bright,

    Kimberly O'Connor Coldwell Banker Realty

    1916 Stevens Dr, Chester, MD 21619
  • /21

    $989,990 New Construction

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

    102 Boatswain Way Unit 34, Chester, MD 21619

    Stylish gourmet kitchen centered around a large island. Dining space with convenient dry bar for hosting. Open great room featuring an electric fireplace. Balcony extending from the main living area. Owner’s suite with two spacious walk-in closets. Private sitting area in owner’s suite with balcony connection. Owner’s bath with dual sinks & glass shower enclosure.

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 34, Chester, MD 21619
  • /35

    $849,990 New Construction

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

    102 Boatswain Way Unit 32, Chester, MD 21619

    Elegant gourmet kitchen with designer cabinetry & center island. Spacious great room featuring electric fireplace. Charming dining area with dry bar for efficient serving. Serene owner's suite & spa bath with frameless shower door. Convenient home office for working remotely. Peaceful balcony for outdoor relaxation.

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 32, Chester, MD 21619
  • /52

    $799,990 New Construction

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

    110 Boatswain Way Unit 3042, Chester, MD 21619

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

    Mary Anne Kowalewski KOVO Realty

    110 Boatswain Way Unit 3042, Chester, MD 21619
  • /61

    $765,000

    • 2 Beds
    • 2.5 Baths

    111 Marshgrass Way Unit 43, Chester, MD 21619

    Rare penthouse unit with year-round water views perfectly positioned to capture stunning sunrises every morning. This home has been owned and meticulously maintained by the original owner who spared no expense and opted for every builder upgrade that was offered, over $60,000.00 in options. The open concept design seamlessly connects the living room, dining area, and kitchen areas, all enhanced

    John Freeman Coldwell Banker Realty

    111 Marshgrass Way Unit 43, Chester, MD 21619
  • /21

    $589,990 New Construction

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

    Severn Plan at K. Hovnanian’s® Four Seasons at Kent Island - Luxury Condos, Chester, MD 21619

    Expansive end home condominium with 3 bedrooms. Lavish gourmet kitchen and formal dining area. Huge great room with large corner balcony. Fantastic owner’s suite and sitting room with access to balcony. Extravagant owner’s spa bath with two walk-in closets. Large secondary bedrooms for all of your company. Pricing is inclusive of an average location premium.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36503530, Chester, MD 21619
  • /32

    $494,900 Open Sat 11AM - 1PM

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    1000 Herons Nest Way Unit 23, Chester, MD 21619

    Welcome to 1000 Herons Nest Way, where you can live the good life at an great price. This immaculate two bedroom condo, with two and a half baths and additional flex space, provides turn key convenience and resort style amenities. This home is a MUST SEE! This FORMER MODEL is like new and includes features that other condos won’t - including decorator upgrades, custom designed closets, plantation

    Nola Meyers EXP Realty, LLC

    1000 Herons Nest Way Unit 23, Chester, MD 21619
  • /63

    $649,990 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    102 Warbler Way Unit 2911, Chester, MD 21619

    Welcome to the Magothy, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office

    Mary Anne Kowalewski KOVO Realty

    102 Warbler Way Unit 2911, Chester, MD 21619

Showing Results 41 - 80, Page 2 of 3

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