Shepherdstown, WV Homes

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  /40

  Est $1,265,288 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,584 Sq Ft

  1901 Trough Rd, Shepherdstown, WV 25443

  1901 Trough Rd, Shepherdstown, WV 25443
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  /78

  $599,900

  • 4 Beds
  • 3.5 Baths
  • 4,128 Sq Ft

  55 Hidden Valley Cir, Shepherdstown, WV 25443

  What a home and property! Nearly one-and-a-half park-like acres in Shepherdstown set the stage for this stately colonial-style home. A fenced rear yard is great for two-legged and four-legged friends and a mixture of mature trees and open spaces in all directions provides a magical and private sensation. Despite this far, far away feeling, modern conveniences are readily at hand. Comcast Xfinity

  Nicholas Palkovic Touchstone Realty, LLC

  55 Hidden Valley Cir, Shepherdstown, WV 25443
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  /84

  $300,000 Sold Oct 30, 2025

  • 1,658 Sq Ft
  • $181/SF
  • 102 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1968

  838 Billmyer Mill Rd, Shepherdstown, WV 25443

  MUST SEE! Enjoy country living sitting on the large front porch of this brick raised rancher overlooking beautiful farmland near historic Shepherdstown and Shepherd University. Home features two (2) bedrooms, kitchen, living room, dining room w/exit to a large tiered deck, full bathroom, breezeway w/laundry, plus a large partially finished basement w/woodstore, storage and 2 car attached garage.

  Densil Nibert Nibert Realty & Auctions, LLC

  838 Billmyer Mill Rd, Shepherdstown, WV 25443
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  /39

  Est $735,238 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,350 Sq Ft

  101 N Princess St, Shepherdstown, WV 25443

  101 N Princess St, Shepherdstown, WV 25443
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  /63

  $849,900

  • 5 Beds
  • 3.5 Baths
  • 3,147 Sq Ft

  1132 Terrapin Neck Rd, Shepherdstown, WV 25443

  MAJOR PRICE IMPROVEMENT! Seller is in the process of relocating. Welcome home to Shepherdstown - West Virginia’s oldest town full of immeasurable history, arts, charm, and uniqueness! This is your chance to escape all the hustle and bustle to discover this exceptional timber frame retreat-style property located in historic Shepherdstown! With almost 3,200 square feet of meticulously crafted

  Andrew Lowe Path Realty

  1132 Terrapin Neck Rd, Shepherdstown, WV 25443
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  /49

  $465,000 Sold Oct 30, 2025

  • 3,858 Sq Ft
  • $121/SF
  • 13 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2005

  79 Maddex Farm Dr, Shepherdstown, WV 25443

  Welcome to the beautiful community of Maddex Farm! This home offers the space you covet with a location you will love! The main level is perfect for entertaining, featuring formal living and dining areas, a morning room, and spacious family room. The kitchen offers plenty of cabinets and counter space and is open to the family room and morning room so you can enjoy every moment. A half bath is

  Gavin Washington Weichert Realtors - Blue Ribbon

  79 Maddex Farm Dr, Shepherdstown, WV 25443
• 

  

  /18

  Est $402,923 Not Listed For Sale

  • 1 Bed
  • 1.5 Baths
  • 1,552 Sq Ft

  306 W German St, Shepherdstown, WV 25443

  306 W German St, Shepherdstown, WV 25443
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  /71

  $649,900

  • 3 Beds
  • 2.5 Baths
  • 2,945 Sq Ft

  63 Hackberry Cir, Shepherdstown, WV 25443

  Welcome to Fernbank at Cress Creek, a neighborhood just down the road from Cress Creek Golf Club, and the well known Bavarian Inn of historic Shepherdstown. Enjoy the Cress Creek community complete with plenty of amenities not just catering to the golfer, with a swimming pool, tennis/pickle ball courts, 18 hole golf course, clubhouse, restaurant/bar facilities and wedding venue. This home was

  Laurel Murray Samson Properties

  63 Hackberry Cir, Shepherdstown, WV 25443
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  /77

  $544,900 Sold Oct 30, 2025

  • 4,527 Sq Ft
  • $120/SF
  • 23 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 2006

  339 Maddex Farm Dr, Shepherdstown, WV 25443

  JUST 50 MINS TO LEESBURG · 13 MINS TO COMMUTER TRAIN · Over 4,500 finished sqft across 3 levels, offering plenty of space to spread out. Expansive rooms, open floor plan, soaring 2-story foyer, catwalk & elegant columns create an impressive feel. Fresh paint with transferable warranty and brand-new carpet throughout. Main-level in-law suite with door to full bath adds flexibility. Major updates

  Steph Mitchell Samson Properties

  339 Maddex Farm Dr, Shepherdstown, WV 25443
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  /15

  Est $282,667 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,288 Sq Ft

  310 W German St, Shepherdstown, WV 25443

  310 W German St, Shepherdstown, WV 25443
• 

  

  /95

  $729,000

  • 4 Beds
  • 4.5 Baths
  • 5,485 Sq Ft

  11 Marsh Hawk Way, Shepherdstown, WV 25443

  NEW AND IMPROVED PRICE!!! SCHEDULE YOUR TOUR TODAY! This beautifully maintained all-brick home rests on a lush, landscaped 1-acre lot in the coveted Springs of Shepherdstown community. With 4 bedrooms, 4.5 bathrooms, and a 2-car garage, the home blends timeless charm with thoughtful upgrades throughout. Gleaming hardwood floors and a marble-floored foyer welcome you inside. The living room

  Lauren Seaton Charis Realty Group

  11 Marsh Hawk Way, Shepherdstown, WV 25443
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  /39

  $622,000 Sold Oct 24, 2025

  • 3,300 Sq Ft
  • $188/SF
  • 96 Days On Market

  • 6 Beds
  • 4.5 Baths
  • Built 2002

  927 Persimmon Ln, Shepherdstown, WV 25443

  NEW PRICE $622,222 | Nestled in the tranquil setting of Shepherdstown, this beautiful Colonial home offers a serene retreat with tons of amenities! Boasting 6 bedrooms and 4.5 bathrooms, it sits on nearly 4 acres of picturesque land. The partially fenced property includes a charming chicken coop, as well as other livestock included areas, perfect for fulfilling your farm dreams. Enjoy leisurely

  Brianna Goetting Pearson Smith Realty, LLC

  927 Persimmon Ln, Shepherdstown, WV 25443
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  /60

  Est $446,578 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,924 Sq Ft

  15 Shaw Place, Shepherdstown, WV 25443

  15 Shaw Place, Shepherdstown, WV 25443
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  /68

  $650,000

  • 4 Beds
  • 3 Baths
  • 2,878 Sq Ft

  89 Morgan Grove Rd, Shepherdstown, WV 25443

  Absolutely gorgeous 4-bedroom, 3-bathroom, home with approximately 2878 total finished square feet, sitting on 8 UNRESTRICTED, PRIVATE ACRES in Shepherdstown. This property is in a great location, only 2.5 miles from Shepherd University and about 5 minutes from downtown Shepherdstown. Updates include: a NEW ROOF, NEW HVAC, new hot water heater, new siding, fresh paint from top to bottom, new wide

  Sheldon Everhart Freedom Real Estate Group, LLC.

  89 Morgan Grove Rd, Shepherdstown, WV 25443
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  /7

  $90,000 Sold Oct 21, 2025

  • Land
  • 1.27 Acres
  • $70,866 per Acre

  • 4 Days On Market

  4004 Scrabble Rd, Shepherdstown, WV 25443

  Build Your Dream Home on 1.27 Acres with Well & Septic Already in Place!Located between historic Shepherdstown and the growing Martinsburg/Spring Mills area, this 1.27-acre lot offers the perfect blend of privacy and convenience. The property is mostly cleared, level, and ready for your custom home. With a well and septic system already installed, much of the prep work is done—saving you

  Chris Ross Samson Properties

  4004 Scrabble Rd, Shepherdstown, WV 25443
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  /53

  Est $405,609 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,290 Sq Ft

  527 Maddex Farm Dr, Shepherdstown, WV 25443

  527 Maddex Farm Dr, Shepherdstown, WV 25443
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  /61

  $724,990

  • 5 Beds
  • 2.5 Baths
  • 2,721 Sq Ft

  4781 Scrabble Rd, Shepherdstown, WV 25443

  ***PRICED BELOW CURRENT APPRAISAL***The George Washington Hollida House | 4781 Scrabble Rd, Shepherdstown, WV 254435 Beds | 2.5 Baths | 2,721 Sq Ft | 5 Unrestricted Acres Step into a piece of West Virginia history with the George Washington Hollida House, a stunning c.1840 brick Colonial I-House nestled on 5 UNRESTRICTED acres in scenic Scrabble, just minutes from historic

  Susan Wathen EXP Realty, LLC

  4781 Scrabble Rd, Shepherdstown, WV 25443
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  /59

  $560,000 Sold Oct 17, 2025

  • 2,144 Sq Ft
  • $261/SF
  • 17 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1987

  278 Chandler Dr, Shepherdstown, WV 25443

  Nestled on a private lot in the serene Oakleigh subdivision, this charming contemporary home offers a perfect blend of lifestyle and functionality. Set on three acres with several outbuildings, including a greenhouse, the expansive garden beds, babbling koi pond, and colorful foliage spread across the property are simply beautiful. The home features four spacious bedrooms and three full

  Adam Miller Coldwell Banker Premier

  278 Chandler Dr, Shepherdstown, WV 25443
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  /68

  Est $518,391 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 4,185 Sq Ft

  182 Maddex Square Dr, Shepherdstown, WV 25443

  182 Maddex Square Dr, Shepherdstown, WV 25443
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  /30

  $450,000

  • 2 Beds
  • 2 Baths
  • 1,530 Sq Ft

  8709 Shepherdstown Pike, Shepherdstown, WV 25443

  Welcome home to this beautiful colonial right in the heart of Shepherdstown, but just outside of city limits. This home features the perfect blend of historic charm and modern living , where every detail invites you to call it home. This charming, well maintained 1920 Colonial-style home boasts two bedrooms, two full baths and over 1,500 sq. ft. of living space! Featuring stunning wood floors

  Nadine Kennedy Coldwell Banker Premier

  8709 Shepherdstown Pike, Shepherdstown, WV 25443
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  /39

  $325,000 Sold Oct 15, 2025

  • 2,466 Sq Ft
  • $132/SF
  • 16 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1986

  53 Stonehouse Ln, Shepherdstown, WV 25443

  Welcome to your private retreat in Shepherdstown! Nestled on 2 acres with surrounding area being newly declared protected parkland. This contemporary home is filled with character and architectural charm. The layout features a main-level bedroom and an inviting design that blends beautifully with its natural surroundings. NEW ROOF & NEW SKYLIGHTS in last couple of years. Wildlife and privacy

  Kara Burnett Samson Properties

  53 Stonehouse Ln, Shepherdstown, WV 25443
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  /19

  Est $247,824 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft

  15 Raven Way, Shepherdstown, WV 25443

  15 Raven Way, Shepherdstown, WV 25443
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  /51

  $359,900

  • 3 Beds
  • 2.5 Baths
  • 1,169 Sq Ft

  99 Exeter Ct, Shepherdstown, WV 25443

  This charming split-level home rests on nearly half of an acre at the end of a cul-de-sac within five minutes of downtown, historic Shepherdstown! Hardwood flooring runs throughout the living areas on the main floor including the living, dining and kitchen spaces. Large windows throughout provide an abundance of natural light. The main level flows into three bedrooms along with one full and one

  Errika Best Greentree Associates of Shepherdstown, Inc.

  99 Exeter Ct, Shepherdstown, WV 25443
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  /62

  $725,000 Sold Oct 15, 2025

  • 4,910 Sq Ft
  • $148/SF
  • 3 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2003

  22 Reachcliff Cir, Shepherdstown, WV 25443

  Welcome home to 22 Reachcliff Circle—a meticulously maintained 4-bedroom, 4.5-bath home in the sought-after Fernbank at Cress Creek community in historic Shepherdstown. Situated just minutes from downtown Shepherdstown and Shepherd University, this location offers the perfect balance of peaceful living with easy access to dining, shopping, and cultural experiences.From the moment you step

  Sara Duncan RE/MAX Distinctive Real Estate

  22 Reachcliff Cir, Shepherdstown, WV 25443
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  /50

  Est $267,932 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  392 Persimmon Ln, Shepherdstown, WV 25443

  392 Persimmon Ln, Shepherdstown, WV 25443
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  /73

  $1,600,000

  • Studio
  • 3,692 Sq Ft

  1585 Gardners Ln, Shepherdstown, WV 25443

  1585 Gardners Lane: Circa 1850 Farmhouse converted into 6 apartments, 2 cottages and 1 duplex totaling 10 units on 13.2 acres with huge bank barn and fencing/pasture for horses. 100% occupancy, great rental history over past 20 years of ownership. Roughly $11k per month totaling a potential yearly income of $132,910 (2025). Current owner operated and managed these units as short term rentals on

  Brad Lewis Greentree Associates of Shepherdstown, Inc.

  1585 Gardners Ln, Shepherdstown, WV 25443
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  /35

  $649,999 Sold Oct 14, 2025

  • 2,231 Sq Ft
  • $291/SF
  • 114 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  21 Steamboat Run Rd, Shepherdstown, WV 25443

  Ready for October 6th 2025 delivery!! Rare opportunity to own a new home with river access in Steamboat Run!! 1.55 +/- acres of level ground. Underground Utilities for your new home. Your home will fit in perfectly and will include the following: 4 bedrooms with 2.5 baths for the ranch craftsman style home. Quality construction with nicely upgraded full kitchen appliance package, granite or

  Rick Boswell Gain Realty

  21 Steamboat Run Rd, Shepherdstown, WV 25443
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  /43

  Est $452,584 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,466 Sq Ft

  841 Persimmon Ln, Shepherdstown, WV 25443

  841 Persimmon Ln, Shepherdstown, WV 25443
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  /86

  $1,599,999

  • 5 Beds
  • 4.5 Baths
  • 5,641 Sq Ft

  414 Mcmurran Farm Ln, Shepherdstown, WV 25443

  Welcome to 414 McMurran Farm Lane, this remarkable property was built for comfort, leisure, and everyday ease. Offering over 5,600 square feet of beautifully designed living space and an adjoining lot (Lot 6) for a total of 18+ acres, this property delivers a rare combination of luxury, functionality, and rural tranquility. From the moment you arrive, the mature tree lined driveway and expansive

  Jessica Smith Roberts Realty Group, LLC

  414 Mcmurran Farm Ln, Shepherdstown, WV 25443
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  /104

  $990,000 Sold Oct 14, 2025

  • 4,390 Sq Ft
  • $226/SF
  • 12 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1759

  211 E High St, Shepherdstown, WV 25443

  The Abraham Shepherd Home – A Rare Blend of History, Elegance & Modern ComfortBuilt in 1759, the Abraham Shepherd Home is one of the oldest and most iconic residences in West Virginia. Tucked into the heart of Shepherdstown—West Virginia’s oldest town—this distinguished property offers a seamless blend of historic grandeur and thoughtful modern updates, including rare off-street parking—a

  Meghan Pachas Realty ONE Group Old Towne

  211 E High St, Shepherdstown, WV 25443
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  /74

  Est $569,694 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 4,108 Sq Ft

  564 Steamboat Run Rd, Shepherdstown, WV 25443

  564 Steamboat Run Rd, Shepherdstown, WV 25443
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  /37

  $339,000

  • 3 Beds
  • 2.5 Baths
  • 2,680 Sq Ft

  286 Starkeys Landing, Shepherdstown, WV 25443

  Welcome to 286 Starkeys Landing, a spacious 3-bedroom, 2.5-bath townhome quietly set within the established Starkeys Landing community of Shepherdstown, West Virginia. Offering just over 2,100 square feet of finished living space, this home blends warmth, comfort, and light in a way that feels immediately like home. The lower level opens through a bright two-story foyer where sunlight filters

  Carolyn Young Samson Properties

  286 Starkeys Landing, Shepherdstown, WV 25443
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  /48

  $605,000 Sold Oct 10, 2025

  • 2,540 Sq Ft
  • $238/SF
  • 2 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1988

  306 Tinsley Cir, Shepherdstown, WV 25443

  Welcome to 306 Tinsley Circle, a beautifully renovated home tucked away in one of Shepherdstown’s most desirable neighborhoods. The seller is relocating for work, offering you the rare opportunity to own a freshly updated property that combines modern elegance with timeless charm. Stunning Sunroom AdditionThe centerpiece of this home is the enormous sunroom, showcasing soaring

  Tara Lowe Samson Properties

  306 Tinsley Cir, Shepherdstown, WV 25443
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  /106

  Est $611,061 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 4,184 Sq Ft

  977 Turner Rd, Shepherdstown, WV 25443

  977 Turner Rd, Shepherdstown, WV 25443
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  /42

  $975,000

  • 3 Beds
  • 2.5 Baths
  • 2,500 Sq Ft

  105 Rabbits Rest Ln, Shepherdstown, WV 25443

  **** Update*****This home comes with unique financing opportunities! The seller is willing to offer partial owner financing, creating additional flexibility for well-qualified buyers. Plus, our preferred lender offers special financing solutions designed to help buyers explore more accessible loan programs. Ask for details Lindal Cedar Home on 10.08 Acres of Peace & BeautyTucked away on

  Jennifer Fortson Charis Realty Group

  105 Rabbits Rest Ln, Shepherdstown, WV 25443
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  /6

  $67,102 Sold Oct 03, 2025

  • Land
  • 0.13 Acre
  • $516,169 per Acre

  • 4 Days On Market

  110 College St, Shepherdstown, WV 25443

  Unique buildable lot only blooks to Shepherd University and downtown Shepherdstown. Quiet street located in the Historic Distric of Shepherdstown. Well established neighborhood. Possibility of 2 townhomes could be built on lot. Please contact the City of Shepherdstown to verify possibilities. Go and Show

  Robert Bir Samson Properties

  110 College St, Shepherdstown, WV 25443
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  /96

  Est $1,112,603 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,427 Sq Ft

  1827 Terrapin Neck Rd, Shepherdstown, WV 25443

  1827 Terrapin Neck Rd, Shepherdstown, WV 25443
• 

  

  /63

  $549,000

  • 3 Beds
  • 3 Baths
  • 2,446 Sq Ft

  200 Meadow Ridge Dr, Shepherdstown, WV 25443

  Rare Villa Opportunity in Sought-After Cress Creek Golf CommunityA rare find in one of Shepherdstown’s most desirable neighborhoods—only three double villa units like these were ever built in Cress Creek, and the last one sold nine years ago! Perfectly sited on a beautiful .344-acre lot with golf course views, this home offers refined comfort and effortless living.Step inside to an

  Paula Miller Coldwell Banker Premier

  200 Meadow Ridge Dr, Shepherdstown, WV 25443
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  /32

  $387,500 Sold Oct 01, 2025

  • 1,288 Sq Ft
  • $301/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1981

  59 Shade Ln, Shepherdstown, WV 25443

  ***OPEN HOUSE*** Saturday, August 30th from 12-2pm ***OPEN HOUSE*** Enjoy the best of country living in this charming and spacious rancher, perfectly situated on 2.17 acres of scenic land. Featuring 3 bedrooms and 2 full baths, this freshly painted home offers a bright, welcoming atmosphere. The 2-car garage and unfinished basement provide ample storage and room to customize to your needs. Recent

  Ronald Wolfe Charis Realty Group

  59 Shade Ln, Shepherdstown, WV 25443
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  /41

  Est $672,276 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 5,204 Sq Ft

  60 Pathfinder Ct, Shepherdstown, WV 25443

  60 Pathfinder Ct, Shepherdstown, WV 25443

Showing Results 41 - 80, Page 2 of 18