Step into a piece of history with this charming Colonial home, originally built in the 1840's, nestled in the heart of the vibrant Shepherdstown community. This beautifully maintained residence boasts 3 spacious bedrooms (4th bedroom option) and 3 full bathrooms, offering a perfect blend of classic elegance and modern comfort across more than 2,300 sq. ft. of living space. Inside, the traditional floor plan welcomes you with rich hardwood floors and an inviting eat-in gourmet kitchen, ideal for culinary enthusiasts. Enjoy cozy evenings in the cozy living spaces or entertain guests in the combination kitchen/dining area, enhanced by ample natural light. The main floor laundry adds convenience to your daily routine. Step outside to discover a private oasis on a generous 0.46-acre lot, beautifully landscaped and backing to serene trees. The outdoor space features a charming brick patio and porch, perfect for summer BBQs or quiet mornings with a cup of coffee. Additional structures, including a shed, provide extra storage for your gardening tools or hobbies. Located in downtown Shepherdstown, you'll enjoy easy access to local shops, restaurants, and cultural attractions, making this home not just a residence but a lifestyle. With off-street parking and an attached carport, convenience is at your fingertips. Experience the perfect blend of historic charm and modern amenities in this delightful home-your dream awaits!

COMING SOON - SHOWN BY APPOINTMENT ONLY - Escape to peaceful wooded living without sacrificing convenience in this beautifully upgraded Insight Home located just minutes from Historic Downtown Milton, Lewes, Millsboro, and Delaware's award-winning beaches. Backing to mature woods and a community buffer, this property offers exceptional privacy while placing shopping, dining, breweries, healthcare, and coastal attractions within easy reach.Designed for easy one-level living, the bright open floor plan features luxury vinyl plank flooring throughout with no carpet, abundant natural light, custom built-in bookcases, and quality finishes that make this home truly move-in ready. The gourmet kitchen is the centerpiece of the home, featuring White Ice granite countertops, stainless steel appliances, a glass tile backsplash, under-cabinet lighting, and generous cabinet and prep space perfect for everyday living or entertaining family and friends.The private owner's suite continues the home's luxury feel with an upgraded bath showcasing quartz countertops, a custom tiled shower, rainfall shower head, and built-in bench. Additional bedrooms and living spaces provide flexibility for guests, a home office, or hobbies.Step outside to your own private backyard retreat where a low-maintenance Trex deck overlooks mature trees and protected community green space, creating a peaceful setting rarely found in today's market. Raised garden beds, professional landscaping, and a five-zone irrigation system complete the outdoor experience.Built by Insight Homes with Green Home energy-efficient construction, this home offers long-term value with a conditioned crawl space, dual-zone heat pump with propane backup, tankless on-demand water heater, central vacuum system, floored attic storage, extra laundry room cabinetry, garage pulley storage system, and Delaware Electric Cooperative electric service.If you've been searching for a move-in-ready home that combines modern upgrades, energy efficiency, one-level living, wooded privacy, and a central location close to Milton, Lewes, Millsboro, beaches, restaurants, shopping, and everyday conveniences, this home is one you won't want to miss. Schedule your private showing today.

This home is READY! With over 20 years building experience, Highland Ridge Builders welcomes you to your fresh start in the heart of Virginia's countryside. This brand-new construction home offers 1,850 square feet of thoughtfully designed living space on a sprawling 5.25-acre lot — room to roam, room to grow, and room to make it truly yours. Step inside to an open-concept floor plan that fills the home with natural light and effortless flow, perfect for everyday living and entertaining alike. Generously sized bedrooms with ample closet space provides comfortable retreats for the whole family, while the modern layout keeps kitchen, living, and dining spaces connected and welcoming. You'll appreciate numerous upgrades throughout: granite counters including bathrooms, 36 kitchen cabinets with soft-close hardware, ceiling fans in all bedrooms and living areas, ceramic tile in baths and laundry, just to name a few. The oversized poured concrete porch will certainly delight with plenty of room for chairs. Let's not forget the 12x16 deck off the back overlooking the private wooded lot! Downstairs, a full unfinished walkout basement with full bath rough-in offers endless potential — envision a home gym, media room, additional bedrooms, or the ultimate rec space, all designed to your vision. Outside, over five acres of land offer privacy, space for gardens, animals, a workshop, or simply room to breathe — all while being brand new from the ground up, so you can move in with zero deferred maintenance and complete peace of mind. The well and septic locations were thoughtfully placed to allow for a pool if desired. Whether you're looking for a peaceful homestead, room for hobbies, or simply a quiet slice of Virginia to call your own, 150 E Four Seasons Drive delivers new construction quality with the acreage and flexibility today's buyers are searching for. Built on quality and crafted for life, don't miss this rare combination of brand-new construction and generous acreage — schedule your showing today. Contact listing agent for a walk-through video if you are unable to visit in person. Some photos have been virtually staged

Wake up to sweeping mountain views, peaceful surroundings, and the comfort of knowing everyday conveniences are only minutes away. Set on 2.06 acres in Orchard View Estates, this two-story Colonial-style home offers 4 bedrooms, 3 full bathrooms, 1 half bathroom, a finished walkout basement, and space to enjoy the outdoors in every direction. From the rear deck, start the day watching the sunrise over the mountains. In the evening, settle onto the covered front porch and take in the sunset across the surrounding landscape.Inside, the home provides multiple levels of flexible living space. The finished walkout basement expands the usable footprint and offers direct access to the outdoors. A pellet stove installed in 2018 provides an additional heat source and a comfortable gathering point during cooler months. Fiber optic internet is available, helping you stay connected while enjoying a quieter setting away from more congested areas.The property also includes a two-car attached garage, paved road frontage, and a large storage shed added in 2022. The acreage provides breathing room without creating the feeling of being far removed from town. Whether you are looking for additional living space, mountain scenery, outdoor recreation, or a more relaxed pace, this property offers a practical balance of privacy and convenience.Several major updates and improvements have already been completed. The roof was replaced in 2022, followed by a new dishwasher in 2023 and a new refrigerator with ice maker in 2024. A new water heater was installed in 2025. The furnace received a new motor and additional repairs in 2025.Daily necessities are close at hand, with grocery stores, restaurants, gas stations, and other shopping reported to be approximately 5 minutes away. WVU Medicine Grant Memorial Hospital with a cancer treatment center is approximately a 10 minute drive. Walmart, Tractor Supply, and additional shopping in Moorefield are approximately 25 minutes away.A local park and public access to the South Branch of the Potomac River are reported to be about 7 minutes away, while the public swimming pool is approximately 8 minutes away.For those who enjoy exploring the Potomac Highlands, the location provides convenient access to well-known regional destinations, including Seneca Rocks, Blackwater Falls State Park, Dolly Sods Wilderness, and other mountain recreation areas. Winchester, Virginia, is approximately 1 hour and 20 minutes away, offering expanded options for shopping, dining, entertainment, and day trips.This is the kind of setting that feels tucked away while keeping healthcare, groceries, dining, shopping, river access, and recreation within practical reach. Enjoy mountain views from morning to evening, generous indoor and outdoor space, and the ability to experience a quieter pace without being disconnected from the places you need to go.