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138 E. German Street

Shepherdstown, WV 25443

304-876-3737

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Welcome to Greentree Realty

of Shepherdstown, Inc.

Established in December of 1990, Greentree Realty serves the Shepherdstown Corporation (Historic District), as well as Berkeley and Jefferson Counties.

Our office is located in downtown Shepherdstown, West Virginia adjacent to the campus of Shepherd University. Greentree is just a little more than an hours drive from the Washington and Baltimore metropolitan areas, 45 minutes from Dulles Airport, or an hour and a half by train from Washington´s Union Station.

The area abounds with recreational opportunities from white water rafting and canoeing to horse racing and golf. There are many fine places to stay locally if you choose to make a weekend of it while house searching. Find out why West Virginia is “Almost Heaven!”

Featured Properties

Throughout the region

Welcome to 213 W High Street! Showings begin 5/2 to experience this simply stunning property! This beautifully preserved 2-story residence rests on a double, corner lot in the Historic District. The charming home showcases original architectural elements and offers the perfect balance of comfort, style, and history. Its plaster walls, wood floors and double-hung wood windows have been lovingly maintained. It exudes historical character as you enter through the original front door and into an open foyer with fireplace. A set of original glass paneled doors with transoms lead out to a light-filled sunroom with 12 original six-foot-tall windows! The wainscoting and pickled floorboards encompass this space. The formal dining room creates a gracious space for memorable meals and celebrations. Here a built-in custom bar coordinates with the original fireplace mantle trim while the original, diamond pattern lead glass windows create a distinctive focal point. The dual alcoves provide closet or hutch space. (This area could be renovated to a 1st floor bedroom as the adjacent half bath was once a full bath!) To the left of the entry an elegant, yet comfortable living room is flanked by a grand fireplace and floor to ceiling built-in bookcases. Music played from here can be piped to speakers around the main floor. A standout feature in the kitchen is the custom-built cabinetry with abundant storage space, recycling center, kitchen desk, and display shelves which were all thoughtfully integrated. Beautiful schoolhouse lights were carefully repurposed from a local church remodel while the striking black and white tile floors add a bold, graphic touch. Kitchen finishes include stainless-steel appliances, Corian countertops, and a Kohler farmhouse sink. A powder room is tucked behind a discreet pocket door in the butler’s pantry. An additional flex space lends itself to endless possibilities with floor to ceiling built-in shelves and wondrous natural light (office, guest room, playroom, craft room or even a small home business). The functional mudroom, with sizable utility closet, hosts a walk-in pet shower/cleaning room along with a second small stairway and a hidden cellar door. The rear screened porch leads to a lovely deck path where you will find your very own hidden spa with a hot tub, private changing area and outdoor shower! Adjacent is a custom stone patio with a thoughtfully arranged fire ring and planters that create a harmonious outdoor retreat! Upstairs, the four bedrooms boast historic charm with built-in shelves and aspects of the original fireplaces. The soaking tub in the remodeled full bath is also original to the house. The primary bedroom is a cozy retreat with transom stained-glass art, leaded glass diamond window, an en suite primary bathroom and entry to the second floor sleeping porch. The stairway to the full-house attic is also located off of the sleeping porch. Followed by a cozy second floor TV room (or bedroom) with a built-in desk for homework or gaming! This space flows into the laundry room with separate Kohler deep utility sink and a unique ductless dryer. The next room is currently used as a home office, but could function as a bedroom or be converted back to a kitchenette space. Cabinets along one full wall once outfitted a sink & small fridge! Outside, immerse yourself in the enchanting gardens, where nature and history seamlessly intertwine. The historic rock walls, meandering stone paths, and two custom-built sheds add charm, character as well as utility. The fenced vegetable garden is a true highlight, providing a protected space to grow fresh produce and herbs. The many species of native trees support birds & butterflies while shading the house in the heat of summer. Immerse yourself in the splendor of this historic, small town. Conveniently stroll to the C&O Canal, restaurants, shops, or Shepherd University. Schedule a personal tour to explore this stunning piece of history! $830,000 COMING SOON

213 W High Street Shepherdstown, West Virginia

4 Beds 3 Baths 3,459 SqFt 0.76 Acres

Terrific floor plan for the buyers that need a bedroom on the first floor, but then more bedrooms and areas Terrific floor plan for the buyers that need a bedroom on the first floor, but then more bedrooms and areas for visitors and family available! This beautiful stucco home is sited up high on a corner lot. Lots of nice landscaping surrounds the house. Architectural shingled roof is only two years old. Inside, the two story foyer beckons you to an open, bright (also two story) great room accented by a beautiful Palladian window. Wood burning gas fireplace (gas pipe there for an easy conversion) and the balcony overlook highlight the room! An easy flow to the large eat in gourmet kitchen and formal dining room on one side and then the master suite is off to the right on the other. Large master bath was just redone a few years ago. A living room (or future office) is also off the foyer entrance. The great room opens to the deck and the kitchen opens to a beautiful screened porch. Laundry is on the first floor off the kitchen and garage. A surprise back stairway off the kitchen leads to a really nice finished bonus room upstairs plus two more bedrooms and a bath! Another stairway is off the foyer, making this a fun adventure for children and grandchildren. to run and hide in circles! This home offers lots of light and has many updates besides the roof, from some heat pumps to some new floors. Located in the beautiful golf course community of Cress Creek. See "The Club" at Cress Creek, Shepherdstown online! All different kinds of memberships available from a full membership to just swimming, golf, or tennis. $710,000 ACTIVE

44 N Tamarac Drive Shepherdstown, West Virginia

3 Beds 3 Baths 2,975 SqFt 0.58 Acres

Rare opportunity to find an all brick home situated on a quiet cul de sac in the Fernbank neighborhood! This all brick two story colonial features a master suite on the first floor...if desired...with a 2nd master suite on the second floor! The room downstairs would also make a great FR! Open floor plan, bright and airy, beautiful wood floors, Fr off kitchen highlighted by gas fireplace. Upstairs are three more bedrooms (or office/playroom use) and two full baths. Kitchen leads to a large deck for easy entertaining. In the summertime, you barely know this house is there when the leaves are on the trees! New roof in 2024. Attached two car garage. Solar panels on roof really cut down on electricity costs and warranty will transfer at closing. Located in the beautiful golf course community of Cress Creek. Go online to see info at The Club, Cress Creek, Shepherdstown. The Club offers single memberships for golf, tennis, or swimming! We are only 5 minutes from downtown Shepherdstown which has some incredible restaurants and shopping. Antietam Battlefield, walking trails, C &O canal, Potomac River, and so many historic areas including Harpers Ferry are only minutes away! $625,000 ACTIVE

75 Juniper Circle Shepherdstown, West Virginia

4 Beds 4 Baths 2,589 SqFt 0.5 Acres

This property has so many layers and facets that appeal to many types of buyers. For the outdoorsmen and adventurer, the property sits on approx. 14 unrestricted acres adjacent to 50 wooded acres. 2.2 miles from Cacapon State Park, a 6000 acres park with unlimited outdoor opportunities( Robert Trent Jones golf course, a planned $3.5M bike park, newly renovated lodge, cabins.. the list goes on and on!). 20 minutes from the C&O Canal, a 185 mile canal that follows to Potomac River from Cumberland to Washington DC., perfect for walking or biking. For the entertainer: This one level open concept home was totally renovated with entertaining in mind. Easy care wide plank flooring is carried out through the home. The dining, living and kitchen opens to 1300 square feet of outdoor living. Create meals in your indoor gourmet kitchen or use the outdoor kitchen with custom concrete counter tops. Serve on the custom buffet which is covered with red oak butcher block that is carried throughout the home. Guests can have movie nights on a 65 inch tv housed in a custom cabinet. Relax by the pool fully incased with deep decking. Owners had outlets installed throughout the outdoor area. Evenings can be spent around the fire pit surrounded by the peacefulness of the woods. The indoor outdoor space can easily accommodate gatherings of 75+ people. For the gardener/farmer: Enjoy a deer proofed garden with raised beds and irrigation system covered with outdoor string lighting. A 26x8ft chicken coop area with a 8x10ft house previously housed 13 chickens and 1 turkey that produced 10 eggs a day. The house can hold 30 chickens. After a long day , use the outdoor shower just off the garden. For the art lover: The inside of the home was carefully planned by an artist to provide a gallery vibe. Overhead lighting , dimmers, oversized window sills of 1 1/2 inch red oak to show case art. Woodworking throughout the home was designed by a master woodworker. The grounds are peppered with outdoor art to enhance the green space. 7 miles away the town of Berkeley Springs is filled with artists and galleries. For those looking to relax: Wake up to the sun rising on the east filling the living with light. Enjoy reading and relaxing on screened in porch just off the main living area. Find peace on the screen porch or quiet time on the many decks around the home. If working from home, the property is served with Starlink and fiber installation should be completed in the fall. The owners thought of storage when renovating the home. The front deck contains a hydraulic hatch to a small basement area. Also on the property is a 22x24 garage with new door and separate 20x12 storage building .Inside houses a 12x6 pantry/laundry room. Property has commercial opportunity as a short term rental(VRBO, Air BnB). Land can be subdivided one more time, please contact Morgan County Planning department for more information. Just an 1 hr 45 min from Baltimore, 2hrs from Washington DC, and 45 minutes from Winchester, come visit this piece of heaven in West Virginia. ***Grill, Blackstone ,outdoor black table and chairs, deck umbrellas and TVs do not convey but willing to sell. Screened porch furniture, pool furniture and deck storage boxes DO convey with the property. $499,000 ACTIVE

1395 Rock Gap Road Berkeley Springs, West Virginia

2 Beds 2 Baths 1,344 SqFt 13.69 Acres

Welcome to this amazing home in the highly desirable Maddex Farm! Conveniently located near restaurants and shopping, as well as being a short distance from downtown Historic Shepherdstown and Shepherd University campus. This spacious 4 bedroom, 2 full bath and 2 half bath home boasts an open floor plan design on the main level featuring a morning room off the kitchen, a large family room, formal living room and a half bath. The second level of the home has 4 bedrooms and 2 full baths, boasting a master suite: Spacious master bath with separate ceramic shower and soaking tub, dual vanity and a large walk in closet. Unique to most models in Maddex Farm, this home as the laundry room is conveniently located in the hallway near all the bedrooms on the second floor. The walk-out basement has approximately 700 square feet finished as recreation/play/ rooms and a half bath leaving approximately 250 square feet of unfinished storage/utility room. New in 2023 is the large, rear Trex deck for entertaining, barbecuing, and family events. Relax knowing the pets can run free in the nice fenced in back yard. Come see before you miss out on this one! $445,000 COMING SOON

424 Maddex Farm Drive Shepherdstown, West Virginia

4 Beds 4 Baths 3,054 SqFt 0.25 Acres

Coming soon.....May 15th! This adorable home is nestled just hop, skip and a jump from Historic Shepherdstown and Shepherd University campus. 60 Killdeer Avenue has been lovingly cared for by the same owner for almost two decades and has just recently been updated for your future enjoyment. This brick front rancher has 3 Bedrooms and 1 & 1/2 baths all on one level. A brand new roof was just installed March of 2025. With updated stainless appliances, a new washer and dryer set off the kitchen, new flooring, new fixtures and fresh paint, this home will feel new again and be ready for your immediate occupancy. The sunken living room leads you to a side patio perfect for morning coffees or sunset dinners. There's also a nice, spacious, privacy-fenced back yard for play and entertaining . The block shed has a wood stove and is perfect for the gardener and hobbyist. Come see for yourself before its too late! Professional photos will be uploaded prior to going live May 15th! $349,900 COMING SOON

60 Killdeer Avenue Shepherdstown, West Virginia

3 Beds 2 Baths 1,296 SqFt 0.4 Acres

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