Pennington Gap Real Estate

Welcome to Pennington Gap, Virginia—a charming small town nestled in the heart of Lee County. Known for its rich history and picturesque landscapes, Pennington Gap offers a unique blend of rural charm and modern conveniences, making it an ideal place to call home.

As you stroll through the town, you’ll be captivated by its friendly atmosphere and tight-knit community. With a population that embraces Southern hospitality, Pennington Gap is the perfect setting for families, retirees, and anyone looking to escape the hustle and bustle of city life. The town is surrounded by the breathtaking beauty of the Appalachian Mountains, providing ample opportunities for outdoor enthusiasts to explore hiking trails, fishing spots, and scenic vistas.

Pennington Gap boasts a variety of local shops, restaurants, and community events that foster a vibrant local culture. Whether you’re savoring homemade Southern cuisine at a cozy diner or browsing unique boutiques, there’s always something to discover. The town’s commitment to preserving its history is evident in its charming architecture and community landmarks, which tell the story of its past.

Education is a priority in Pennington Gap, with access to quality schools that nurture young minds. The town also benefits from its proximity to larger cities, offering residents the best of both worlds—small-town living with convenient access to urban amenities.

If you’re seeking a peaceful, welcoming community with a strong sense of tradition and natural beauty, Pennington Gap is the perfect place to find your next home. Come experience the warmth and charm of this hidden gem in Virginia!

Newest Listings in Pennington Gap

$125,000

3 Beds ⋅ 1 Baths ⋅ 1355823 MLS

COUNTRY CHARMER WITH A BIG YARD JUST OUTSIDE THE HEART OF BEAUTIFUL PENNINGTON GAP VA! Home features: 3 bedrooms (optional 4th bedroom), 1 bathroom, living room, kitchen, laundry room, storage shed, original hardwood floors, covered front porch perfect for sipping sweet tea and enjoying the sunset, level yard, mountain views, country setting not far from all the shops and dining in Pennington and Jonesville. Call today to schedule your private tour.

245 Kelly Rd, Pennington Gap

Listing courtesy of D.J. Wilder of Century 21 Virginia Wilder Real Estate.

$159,900

3 Beds ⋅ 2 Baths ⋅ 1354906 MLS

4 BEDROOM HOME FOR SALE IN THE DESIRABLE HICKORY FLATS AREA OF PENNINGTON GAP VA! Take a look at this beautiful home featuring: 4 bedrooms (optional 5th), 2 bathrooms, living room, kitchen, LVP flooring, metal roof, fenced yard, covered porch, great location, and so much more! Call today to schedule your tour!

1110 Hickory Flats Rd, Pennington Gap

Listing courtesy of D.J. Wilder of Century 21 Virginia Wilder Real Estate.

$119,900

3 Beds ⋅ 1 Baths ⋅ 1351995 MLS

COME HOME TO THE MOUNTAINS! Nestled along Elk Knob Road in the beautiful Appalachian countryside of Pennington Gap, this inviting 3-bedroom, 1-bath home offers the kind of peaceful country setting buyers are searching for--without giving up the convenience of being close to town. This is the opportunity to slow down, breathe a little deeper, and enjoy the best of Southwest Virginia. Whether you're looking for a full-time residence, a starter home, a weekend retreat, or a place to put down roots, 1046 Elk Knob Road gives you a chance to own a piece of the mountain lifestyle that makes Lee County so special. Inside, you'll find a practical layout with three bedrooms and comfortable living spaces ready to make your own. Outside is where the setting really shines. Elk Knob Road puts you in the heart of the rugged beauty of far Southwest Virginia, where mountain roads, wildlife, fresh air, and wide-open country are part of everyday life. And when you're ready for adventure, you're in a community built for it. Pennington Gap is home to historic Leeman Field, a 33-acre recreation destination featuring sports fields, a swimming pool, playgrounds, pavilions, an amphitheater, horse facilities, pickleball and tennis courts, and a walking greenway along the Powell River. The park has a remarkable history--it was once the world's largest enclosed baseball field. Outdoor enthusiasts will love the area's access to Spearhead Trails Stone Mountain, with approximately 34 miles of challenging mountain trails, dramatic overlooks, and some of the best ATV/OHV riding in Southwest Virginia. Beyond Pennington Gap, Lee County offers easy access to an incredible collection of Appalachian destinations, including Wilderness Road State Park, Jefferson National Forest, Cumberland Gap National Historical Park, Cave Springs Recreation Area, and other outdoor and historical attractions. There's also something special about living in a place with genuine Appalachian character. Pennington Gap grew with the arrival of the Louisville & Nashville Railroad in the late 1800s and became an important gateway between Southwest Virginia and eastern Kentucky. Today, that heritage lives on through its historic downtown, community events, Leeman Field, the Lee Theatre, outdoor recreation, and the people who call this corner of Virginia home. 1046 Elk Knob Road isn't just an address--it's an invitation to experience mountain living at its most authentic. If you've been looking for a place where life feels a little quieter, the mountains feel a little closer, and home can be whatever you want it to become, this one deserves a look. Come see 1046 Elk Knob Road and discover why there's no place quite like home in the mountains of Lee County.

1046 Elk Knob Rd, Pennington Gap

Listing courtesy of D.J. Wilder of Century 21 Virginia Wilder Real Estate.

$247,500

1348143 MLS

Turnkey Multifamily Investment Opportunity - 6-Unit Apartment Building with a current 9.59% CAP rate (and lots of room to grow) Income-producing multifamily assets of this size rarely become available in the Lee County market. This 6-unit apartment building presents an outstanding opportunity for investors seeking immediate cash flow, long-term appreciation, and the stability that comes with multiple income streams. Whether you're expanding an established portfolio or purchasing your first multifamily investment, this property offers the scale to generate consistent rental income while reducing vacancy risk through diversified units. With six separate rental opportunities under one roof, investors can benefit from stronger cash flow potential than traditional single-family rentals. Conveniently located in Pennington Gap, the property offers easy access to local employers, schools, shopping, and everyday amenities, helping support continued tenant demand. As rental inventory remains limited throughout the region, well-positioned multifamily properties continue to be among the most sought-after investment opportunities. Opportunities like this don't stay on the market long. Add a proven income-producing asset to your portfolio, capitalize on the growing demand for quality rental housing, and position yourself for both immediate returns and long-term wealth creation. Schedule your private tour today and discover why multifamily investing remains one of the strongest paths to building lasting real estate wealth.

166 Warner Myers Rd, Pennington Gap

Listing courtesy of D.J. Wilder of Century 21 Virginia Wilder Real Estate.

$19,000

1345493 MLS

6.45 acre surveyed tract of land sitting in a nice area of Pennington Gap VA! Currently wooded but would be suitable for a home once cleared. Property has a nice level area for a homesite up front and the back part is very steep. Tax card states city water and sewer is available for hookup. Gorgeous views overlooking the town as well as mountain views! This property does have light restrictions such as; restricted against singlewide mobile homes, but doublewide and modular homes are to be permitted. No House or dwelling with less than 1100 sqft.

Shuler Drive, Pennington Gap

Listing courtesy of Lynzee Evans of Century 21 Virginia Wilder Real Estate.

$92,500

2 Beds ⋅ 2 Baths ⋅ 1341474 MLS

Nature lovers, take note! This affordable Move-In Ready Pennington Gap home combines practical single-level living with incredible outdoor features. Inside, you'll find a spacious kitchen equipped with endless cabinet space, plentiful countertops, a pantry, an eat-in dining area, and a wonderful screened-in porch perfect for enjoying your morning coffee and evening breeze. The layout includes 2 bedrooms with the potential to easily configure a 3rd bedroom, and 1.5 baths. The outdoor space is where this property truly shines--featuring a year-round freshwater creek running down the right side of property, a large level to rolling yard, and 2 functional storage outbuildings. 24-hour notice required for all showings.

509 Rogers Cemetery Rd, Pennington Gap

Listing courtesy of Emily Woods of Century 21 Virginia Wilder Real Estate.

$39,900

1306536 MLS

Seller will consider owner financing! Unrestricted 21.825 acres outside of city limits! This property has a natural spring for water. City water also available nearby. Hunting paradise or buy for seclusion. Close to town yet feels completely isolated when standing in the middle of the property. Wooded, mountainous land ready for some development!

00 Left Poor Valley Rd, Pennington Gap

Listing courtesy of Lynzee Evans of Century 21 Virginia Wilder Real Estate.

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Listings courtesy of Spartanburg Association of Realtors as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.