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308 Reese Drive, Pennington Gap
$275,000
4 Beds ⋅ 2 Baths ⋅ 1327008 MLS
Don't miss this beautiful 4 bedroom, 2 bath, brick home on 11.77 acres. This property is mostly fenced with pasture and woods! This lovely and spacious split level home has so much to offer. It was remodeled in 2022 with a ton of upgrades.... Including a new kitchen with quartz counter tops, a butcher block island counter top, an expanted doorway that gives the kitchen, dining room, and upstairs family room a more open floor plan design, an updated upstairs bathroom, tankless water heater, and new flooring in most of the home. You can cozy up to the wood stove in the finished basement on those cold winter nights for a family movie. Outside you'll find stunning views of the mountains that can be enjoyed from the sunny front porch and just about anywhere in the yard. Enter in to the basement from the outside on the newly built cascading steps. Let the kids enjoy the new playground area with playset that conveys. This spacious yard with amazing views will definitely be a family favorite! And to continue your tour take a stroll to the large metal shop that has electric and a concrete floor. As a bonus, in the field next to the shop, is a second home site with electric and septic already in place. Don't wait! Call today to view this beautiful home and property!

308 Reese Drive, Pennington Gap

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

Selling Office: .

285 Noahs Ridge Rd, Pennington Gap
$185,000
4 Beds ⋅ 2 Baths ⋅ 1349361 MLS
Perched above the scenic Powell River in the heart of Southwest Virginia, 285 Noah's Ridge Road offers the perfect blend of luxury, privacy, and Appalachian beauty. Tucked away in a peaceful setting with a meticulously manicured lawn and beautiful river views, this spacious split-foyer home is designed for those who appreciate generous living spaces, and the tranquility of mountain living. Step inside to discover expansive rooms filled with natural light, beautiful real hardwood floors, and a thoughtfully designed floor plan that offers both comfort and functionality. The home has been tastefully updated with newer appliances, numerous modern upgrades, and the peace of mind that comes with a brand-new HVAC system installed in February 2026. Whether you're entertaining family and friends or enjoying a quiet evening overlooking the river, every space has been designed to feel warm, inviting, and effortlessly livable. Outside, the beautifully maintained grounds create your own private retreat. Sip your morning coffee while watching the sun rise over the Powell River, host summer cookouts in the spacious yard, or simply enjoy the serenity that only this remarkable setting can provide. The location is equally impressive. Situated in historic Lee County, you'll be surrounded by some of Virginia's most spectacular outdoor recreation and rich Appalachian heritage. Spend weekends fishing, kayaking, or floating the Powell River Blueway, explore the miles of trails at Cumberland Gap National Historical Park, experience frontier history at Wilderness Road State Park, ride the renowned Spearhead Trails, or catch a live performance at the beautifully restored Lee Theatre. Historic Leeman Field, once known as the world's largest enclosed baseball park, and the iconic Stone Face Rock are just minutes away. Steeped in history, this region played a pivotal role in America's westward expansion. The nearby Wilderness Road, forged by pioneers including Daniel Boone, carried thousands of settlers through the mountains, while Pennington Gap later flourished as a railroad, timber, coal, and agricultural hub in the Powell Valley. Today, that rich heritage blends seamlessly with the area's stunning natural beauty, creating one of Southwest Virginia's most desirable places to call home. Properties that combine exceptional privacy, modern updates, timeless hardwood floors, spacious interiors, and unforgettable Powell River views are rarely available. 285 Noah's Ridge Road isn't simply a home--it's a lifestyle. Schedule your private tour today and experience one of Lee County's hidden gems before someone else calls it home.

285 Noahs Ridge Rd, Pennington Gap

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

Selling Office: .

1106 Smyth Chapel Rd, Pennington Gap
$170,000
3 Beds ⋅ 2 Baths ⋅ 1306675 MLS
✨ Country Charm on 2+ Acres! ✨ Step into comfort with this welcoming 3-bedroom, 1.5-bath home tucked away on just over 2 acres. Recent updates, including a new roof and new appliances, mean you can move right in and start enjoying the space. Outside, you'll find a barn and two additional outbuildings—perfect for hobbies, storage, or animals. There's room to garden, play, or simply soak up the peace and quiet of country living. This property offers the best of both worlds: a cozy home filled with potential and the land you've been dreaming of. All that's missing is you!

1106 Smyth Chapel Rd, Pennington Gap

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

Selling Office: .

1046 Elk Knob Rd, Pennington Gap
$110,000
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.

Selling Office: .

487 Right Poor Valley Rd, Pennington Gap
$100,000
2 Beds ⋅ 1 Baths ⋅ 1323318 MLS
YOUR NEXT ADVENTURE AWAITS!! Take a look at this beautiful 2 bedroom 1 bathroom all BRICK home in the perfect setting!! The home sits on 9 ( NINE ) ACRES of unrestricted land with gorgeous mountain views and joins the SPEARHEAD ATV TRAIL!! Pack your snacks and head out on the trail right outside your backyard! The adventure doesn't stop there- look out the front door you'll see LEEMAN FIELD where annual CHRISTMAS LIGHT Displays, Summer Concerts, LEE COUNTY FAIR, WALKING TRAILS, RIVER Walk, POOL, PLAYGROUNDS, & PAVILLIONS are sure to amaze!! Inside the home you'll find a nice living room, newly remodeled Kitchen, Updated Bathroom, 2 Large Bedrooms(Could be divided into 3 smaller rooms). Speaking of upgrades- Think about turning the covered carport into additional living space- maybe a huge master suite?! The possibilities are endless!! Call today to schedule your private tour!!

487 Right Poor Valley Rd, Pennington Gap

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

Selling Office: .

168 Tomlinson Rd, Pennington Gap
$90,000
3 Beds ⋅ 1 Baths ⋅ 1331573 MLS
Adorable 3 bedroom, 1 bath home sitting on approx 1 acre just outside of Pennington Gap city limits. This house has a fresh coat of paint inside and out. New heatpump and hot water heater. Roof is approximately 5 years old. This would make a great rental property or starter home! Handicap accessible with a ramp to the back door/patio. Basement with plenty of storage area and one car garage. 2 storage buildings convey. Schedule a tour today!

168 Tomlinson Rd, Pennington Gap

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

Selling Office: .

319 Main St, Pennington Gap
$90,000
3 Beds ⋅ 1 Baths ⋅ 1316258 MLS
Welcome to 319 Main Street, a cozy and well-loved home in the quaint town of Pennington Gap, Virginia! This three-bedroom, one-bath home offers nearly 1,800 square feet of comfortable living space on a 0.31 acre lot. Built in 1950, it carries plenty of charm and character, while updates like a dual heating and cooling system add modern convenience. The system even switches automatically between electric and gas when the temperature drops, keeping utility bills manageable. The roof and windows are in excellent condition, so you can move in with peace of mind. Outside, you'll love the fenced-in yard, perfect for pets or a garden, along with a handy storage building for your tools and extras. Located right in the heart of Pennington Gap, this home gives you easy access to local shops, restaurants, and everything this friendly small town has to offer. As the largest town in Lee County, Pennington Gap is known for its scenic beauty, historic character, and welcoming community. With a list price under 100k, this home is a wonderful opportunity whether you're a first-time buyer, a small family, or simply someone looking to enjoy the charm of Southwest Virginia living! Located in the heart of Pennington Gap giving you convenient access to everything the adorable town has to offer: local shops like Locals Coffee; Stone Mountain yogurt, the Rooster's Pub. Also within walking distance of the LEE Theater and Leeman Feild Park! Pennington Gap is full of history such and we celebrate our rich farming culture with the yearly Tobacco Festival, local farming work shops and more! Call today to learn more about this incredible property before it's gone!

319 Main St, Pennington Gap

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

Selling Office: .

345 U.S. 421, Pennington Gap
$57,000
3 Beds ⋅ 2 Baths ⋅ 1333390 MLS
Opportunity awaits in Pennington Gap! This fixer-upper doublewide offers 3 bedrooms and 2 bathrooms on approximately 3 acres, giving you plenty of space to make it your own. Whether you're looking for an investment property or a place to customize and call home, this property has great potential. Enjoy a peaceful setting while still being just minutes from town for shopping, dining, and everyday conveniences. Bring your vision and turn this property into something special!

345 U.S. 421, Pennington Gap

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

Selling Office: .

3682 Left Poor Valley Rd, Pennington Gap
$53,000
3 Beds ⋅ 1 Baths ⋅ 1331019 MLS
DIAMOND IN THE ROUGH!! This could be the true Virginian Homestead you've been looking for! This nice fixer upper on 5+/- acres sits out in the country but not too far from schools, shopping, dining, and medical facilities. Features include: living room, kitchen, big bathroom, tall crawlspace/basement for storage, covered front porch, seasonal creek in the front that you can hear from the porch, very private back yard, space for gardening and keeping chickens, goats, sheep, etc! The home has been in the family for a long time and lovingly cared for through the years but has set empty for a while and will need a few repairs. Home will need a septic system, roof, and a section of the floor replaced. The property offers incredible opportunity for those willing to take on the challenge! Call today to schedule your tour!

3682 Left Poor Valley Rd, Pennington Gap

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

Selling Office: .

Horseshoe Bend Rd, Pennington Gap
$52,000
1320085 MLS
Wonderful land for sale! This 14.7 acre plot is wooded and level, requiring estimated minimal groundwork for your new home! Easy walkable land with road frontage on a paved road. City water available. Tax card lists a septic tank (buyer to verify). This could be a hunters dream as well! There is a cemetery excepted out of this property with a road bordering this property for access.

Horseshoe Bend Rd, Pennington Gap

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

Selling Office: .

920 Left Poor Valley Rd, Pennington Gap
$37,000
2 Beds ⋅ 2 Baths ⋅ 1351364 MLS
APPALACHIAN ADVENTURE MEETS OPPORTUNITY -- A PROPERTY WITH CHARACTER, LAND & A GARAGE THAT MEANS BUSINESS! Some properties are simply houses. Others are opportunities waiting for the right person to see what they can become. 920 Left Poor Valley Road offers exactly that kind of opportunity. Set in the beautiful Appalachian landscape of Pennington Gap, this property combines the charm and freedom of country living with an incredibly convenient location close to some of Lee County's most sought-after recreational and cultural attractions. At the heart of the property is an older single-wide home, offering a practical place to live while you transform the property into something uniquely your own. But the real showstopper is the huge professional-quality two-car garage, formerly used as a mechanic shop. Whether you're a mechanic, contractor, tradesman, outdoor enthusiast, collector, entrepreneur, or simply someone who needs serious workspace, this building opens the door to possibilities that are hard to find at this price point. Imagine having room for your vehicles, ATVs, motorcycles, tools, equipment, recreational toys and projects--all under one roof. The garage provides the kind of workspace that can make a property exceptionally valuable to the right buyer. And then there is the land. A creek runs along the back of the property, adding that unmistakable Appalachian touch of moving water, natural beauty and outdoor potential. Picture relaxing beside the creek after a long day, creating a firepit area, letting the kids explore, or simply enjoying the sounds of nature. This is the kind of feature that gives a property personality--and makes it feel like more than just an address. Location is another major advantage. Outdoor enthusiasts will love being near Historic Leeman Field Recreation Park, one of Pennington Gap's signature attractions. The 33-acre recreation complex offers an impressive collection of amenities including a swimming pool, playgrounds, sports fields, picnic areas, horse arena and stables, amphitheater, tennis and pickleball courts, walking trails and access to the Pennington Gap Greenway. Leeman Field also hosts community celebrations and seasonal events throughout the year. For the ATV and off-road crowd, the location becomes even more exciting. Spearhead Trails' Stone Mountain Trail system is right in the Pennington Gap area, with the Leeman Field campground serving as a trailhead location. The trail system is a major draw for riders looking to experience the mountains of Southwest Virginia from behind the handlebars. And when it's time to trade the trails for an evening out, the historic Lee Theatre is nearby in downtown Pennington Gap. Originally built in the 1940s and later restored, the theater now serves as a community entertainment hub featuring concerts, plays, movies and other events. This is Appalachian living with access to adventure--mountains, trails, recreation, local entertainment and the unmistakable character of a small Southwest Virginia community. Whether you're looking for a place to establish a home base, a property with room for your hobbies and equipment, a mechanic's dream workshop, or an opportunity to create something special, 920 Left Poor Valley Road deserves your attention. The older home may be modest--but the opportunity is anything but. Properties offering this combination of location, workspace, creek frontage and Appalachian lifestyle don't come along every day. Come see the garage. Walk the land. Listen to the creek. Imagine what you could build here. Call today to schedule your private showing before someone else sees the potential first.

920 Left Poor Valley Rd, Pennington Gap

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

Selling Office: .

00 Left Poor Valley Rd, Pennington Gap
$35,000
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.

Selling Office: .

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.

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