Shepherdstown, WV Homes for Sale with Acreage

Experience the charm of this immaculately preserved 1912 stone house, set on over 2 acres in close proximity to historic Shepherdstown. This spacious 4-bedroom, 2-bathroom home features tall ceilings, hardwood floors, and a wide center hall on the main level. You'll also find two large bedrooms, a study, a cozy living room, a full bath, and a convenient laundry area. At the back of the home, the

Bill Dixon Dandridge Realty Group, LLC

Lindal Cedar Home on 10.08 Acres of Peace & BeautyTucked away on over ten acres of rolling woodland, 105 Rabbits Rest Lane is where timeless architecture meets tranquil living. This striking Lindal Cedar Home captures the essence of peace, privacy, and craftsmanship, created for those who value beauty in both structure and setting.Experience serenity and sophistication just

Jennifer Fortson Charis Realty Group

Delivery date 2/2/2026! This home will have Sage Green Hardiboard siding. Enjoy the best of both worlds — peaceful country living with convenient access to everything you need. This new 2 +/- acre homesite is located in a new community that incorporates a desirable location and country feel! Your new home will be a beautifully built 4-bedroom, 4.5-bath Farmhouse ranch-style, designed with comfort

Rick Boswell Gain Realty

March 2 2026 delivery 2 +/- acres situated in the new community of Hallmark Glen!! Impressive homes in this community offers privacy and convenience for commuters and access to amenities. This home fits perfectly and will include the following: 4 bedrooms with 4.5 baths and an office or flex room. Ranch craftsman style home with Hardi board siding and includes a 2 car side load garage with

Rick Boswell Gain Realty

Home will be ready for delivery June 30 2026! This new home in the new community of Hallmark Glen will have almost 2 acres of level ground on a corner lot!! Cable available with Underground Utilities for your new home and will include the following: 3 bedrooms with 2.5 baths for the ranch craftsman style home. Quality construction with nicely upgraded full kitchen appliance package, quartz

Rick Boswell Gain Realty

Delivery 2/15/2026! Timeless Colonial Charm Meets Modern Comfort — in the New Community of Hallmark Glen! Discover a perfect fusion of classic elegance and contemporary luxury in this newly constructed Colonial home, nestled on 2 +/- acres. Offering unmatched privacy and peaceful surroundings, this refined retreat delivers the comfort of modern living without sacrificing timeless charm. A

Rick Boswell Gain Realty

Welcome to the Bonnymeed Farm, a circa 1883, historically accurate, 3 bedroom, 2 and a half bath, 3,232 square feet, brick colonial on 11.7 unrestricted acres. This home has been lovingly cared for by the same owners since 1995. They are ready to move on to greener pastures and leave the rest of the finishing touches to you. Two zone propane heat and air, propane hot water, 3 working

Brad Lewis Greentree Associates of Shepherdstown, Inc.

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.

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

New Listing in Shepherdstown, West Virginia!Welcome home to this charming rancher nestled on 1.8 acres in beautiful Shepherdstown. Enjoy the ease of one-level living with the added potential of a full, walk-out basement—perfect for future expansion or storage. Inside, you’ll find all NEW gorgeous LVP flooring, new carpets in bedrooms, Upgraded kitchen & new appliances, a cozy fireplace area

Kara Burnett Samson Properties

COMING SOON! Heads up on this over 4400 sq.ft. two story with a finished basement! Freshly painted throughout, almost all new carpeting and vinyl; and beautifully refinished hardwood floors. Few things left for your finishing touches. Celestory windows in great room with high ceilings beckon you in PLUS an eat-in kitchen and formal dining area or use as an office space. Lower level student or

Jacqueline Lewis Greentree Associates of Shepherdstown, Inc.

A Rare Historic Estate with Over 100 Acres in Scenic Jefferson County, WVTruly a one-of-a-kind gem with deep roots in history! Originally established in 1804, this remarkable property spans over 100 acres of rolling pastures and active Christmas tree fields, and is protected under the Jefferson County Farm Land Protection Easement. Managed by Dan and Bryan Holler, the Christmas tree farm adds

Terry Walker Coldwell Banker Premier

Beautifully Renovated Retreat on 3 Acres in Oakleigh Acres – A Rare Shepherdstown Find with four bedrooms and 3 bathrooms! Welcome to your dream home—a fully renovated, move-in-ready gem tucked away on three-level acres in the highly sought-after Oakleigh Acres community of Shepherdstown, WV. This property delivers the perfect fusion of sleek modern style and serene country living, just minutes

Lynn Ober Real Estate Innovations

Welcome to 185 Shepherd Lane, a charming and spacious home just minutes from downtown Shepherdstown, WV. Situated on 2.5076 acres in a peaceful, established neighborhood with large lots, this 4-bedroom, 2.5-bath home offers both comfort and opportunity. A covered front porch welcomes you into the main level, which features a formal living room and dining room (both with beautiful hardwood floors)

Liz McDonald Dandridge Realty Group, LLC

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

New 19 home Community in Shepherdstown! March 30 2026 delivery on this New Cape Cod Home on 2 +/- acres! As you approach the home, a paved driveway creates a welcoming sense of arrival. The Cape Cod's classic gabled roof, symmetrical façade, and dormer windows exude traditional elegance, while contemporary finishes lend a fresh and inviting aesthetic. Step inside to discover a thoughtfully

Rick Boswell Gain Realty

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

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

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.

***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

Come tour this fantastic move-in ready home located in Shepherdstown, WV. Boasting 4 bedrooms and 4.5 baths, this property sits on a corner lot with a partially fenced backyard and a new Trex deck. Numerous upgrades include a new upstairs A/C unit, fresh paint throughout all three floors, new basement carpeting, new washer and dryer, and professional landscaping. The main level features hardwood

Brandon Darr Samson Properties

Exceptional custom Cape Cod home is to be built on a scenic, level lot just outside Shepherdstown. It is filled with the kind of quality details that will elevate your living experience. Enter from the covered porch and find a secondary bedroom, bathroom, and a study with double glass doors to your left. The great room ahead features a fireplace and soaring cathedral ceilings, creating a warm and

Louise McDonald Dandridge Realty Group, LLC