Pittsylvania County Real Estate

Pittsylvania County Real Estate

Welcome to Pittsylvania County, Virginia, a hidden gem nestled in the heart of the Old Dominion. Known for its picturesque landscapes and rich history, Pittsylvania County offers a unique blend of rural charm and modern conveniences, making it an ideal place to call home.

Spanning over 1,000 square miles, Pittsylvania County is the largest county in Virginia, boasting a diverse range of natural beauty—from rolling hills and lush forests to serene lakes and rivers. The Dan River and Smith River meander through the area, providing ample opportunities for fishing, kayaking, and enjoying the great outdoors. For those who appreciate hiking and nature walks, the nearby Blue Ridge Mountains are just a short drive away, offering breathtaking views and trails for all skill levels.

Pittsylvania County is steeped in history, with numerous historic sites and charming small towns that showcase its rich heritage. The county seat, Chatham, features quaint shops, delightful eateries, and a welcoming community atmosphere. The annual events, such as the Pittsylvania County Fair and various farmers' markets, bring residents together, fostering a strong sense of community.

Families will appreciate the county's commitment to education, with a variety of public and private schools that prioritize student achievement and well-being. Additionally, the affordable real estate market here allows for a range of housing options, from cozy cottages to spacious family homes, all set against the backdrop of stunning Virginia landscapes.

Whether you’re seeking a peaceful retreat or an active lifestyle, Pittsylvania County offers the perfect blend of rural tranquility and vibrant community life. Discover your new home in this beautiful corner of Virginia!

Newest Listings in Pittsylvania County

$1,950,000
368567 MLS
Two of the prettiest lots on Smith Mountain Lake! Gorgeous wide water and mountain views with 1.45 total acres across both lots and 320 feet of rip-rap shoreline. A custom boathouse with cabana is already in place, along with well and septic. Absolutely Gorgeous!

365 Hardy Rd, Penhook
$359,000
3 Beds ⋅ 3 Baths ⋅ 368533 MLS
Five wooded acres, a setting that feels miles from anywhere, and you're still only minutes from town. This 2,600+ sqft ranch was built around the way people actually live everything you need on one floor, with room to spread out when company comes. Wake up in the primary suite, pour coffee in the

111 Oaklawn Ter, Gretna
$157,000
3 Beds ⋅ 1 Baths ⋅ 368451 MLS
Welcome to 1197 Straightstone Rd! A cute home nestled in the country in Gretna, VA. Coming with a front porch and deck as well as just over an acre of land, this home provides comfortable space to enjoy the outdoors. This home is conveniently located between Lynchburg and Danville, with options for any of your needs. Whether you are looking for a rental, a family looking for your first home, or even someone wanting one-level living, this is a great opportunity for you.

1197 Straightstone Rd, Gretna
$12,000
368415 MLS
Discover the opportunity to build your vision on this .68-acre undeveloped residential lot located on Hill Crest Lane in Chatham, Virginia. Situated on a quiet no-outlet road with minimal traffic, this property offers a peaceful setting while still providing convenient access to everyday amenities and major routes. With approximately 100 feet of road frontage and a depth of approximately 300 feet, the lot provides a manageable homesite opportunity with room for privacy, outdoor space, and future improvements. The property is zoned residential and offers easy access to Route 29, located less than one mile away, making commuting and travel throughout the region convenient. Whether you're looking to build a primary residence, downsize, or secure land in a growing area, Lot 11 Hill Crest Lane provides an affordable opportunity to own residential acreage in Pittsylvania County.

11 Hill Crest Ln, Chatham
$229,900
3 Beds ⋅ 2 Baths ⋅ 368421 MLS
Don't miss this well-maintained 3-bedroom, 2-bath just outside the Town of Gretna. This home offers comfortable living with room to make it your own, needing only a few finishing touches. The metal roof is approximately 6 years old, and new gutter guards were installed in 2025 for added peace of mind. Relax on the spacious back deck overlooking the yard, while a small creek borders the front of the property, adding to its peaceful setting. A rare bonus is the detached 3-car garage with electric, providing plenty of space for vehicles, a workshop, hobbies, or extra storage. Whether you're looking for your first home, downsizing, or simply want country living with convenience, this property checks all the boxes. Conveniently located just off US-29 near the Town of Gretna, offering an easy commute while enjoying a quiet setting.

120 Windy Rd, Gretna
$15,000
368419 MLS
This could be your view! Build your dream home, vacation get-a-way, or somewhere to get away from it all! Peace and tranquility! Perfectly positioned to capture breathtaking views, elevated to maximize the stunning scenery. Within minutes to Leesville Lake. Quiet enjoyment nestled between Danville and Lynchburg. Enjoy big city amenities in less than an hour or take in small town comfort of nearby Gretna and Altavista communities. Sounds like a perfect place to "just be"!

Sunset Bay Rd, Gretna
$135,000
368358 MLS
Enjoy breathtaking mountain views from both the front and back of this 17+ acre property, creating the perfect backdrop for your future home. A natural tree buffer remains along the neighboring property, adding to the privacy. Toward the rear of the land, you'll find a small creek and several natural springs, enhancing the property's charm and appeal. The front of this property featuring 450 feet of state paved road and a level homesite area. Whether you're looking to build now or invest for the future, this exceptional parcel offers the ideal combination of convenience, natural beauty, and seclusion all with only a short drive into the town of Gretna and access to 29. Back Mountain view is of Smith Mountain.

Weatherford Dr, Gretna
$375,000
4 Beds ⋅ 3 Baths ⋅ 368285 MLS
Picture this: morning coffee in the 34-foot sunroom, evenings on the 24x20 deck with the grill going, and a level 1-acre backyard just waiting for its next chapter string lights over a fire pit, a pergola-covered dining spot, raised garden beds bursting with tomatoes, maybe even a pool one day. A blank canvas ready for the vision. Inside, 3,367 sqft of easy living, with the primary suite, den, and main living all on a single accessible level. The kitchen anchors the great room with a center island and custom cabinetry, while a gas-log fireplace warms the den and a whirlpool tub anchors the owner's retreat. Upstairs is its own world a private bedroom, full bath, and bonus flex space with a kitchenette already roughed in, making it ideal for an in-law suite, guest quarters, or future rental. Teak and birch hardwoods, 9-ft ceilings, crown molding, paved drive, storage outbuilding, Gretna schools. Move-in ready inside dream big outside.

4501 Old Mine Rd, Gretna
$269,900
3 Beds ⋅ 2 Baths ⋅ 368215 MLS
Discover exceptional value in Pittsylvania County! This beautifully updated ranch home offers the perfect combination of peaceful country living and modern convenience. Nestled on 2.90 acres, you'll enjoy the tranquility of rural life while being just 15 minutes from Family Dollar and 20 minutes from Food Lion. Renovated just a few years ago, the home features a newer roof, windows, HVAC system, cabinetry, granite countertops, luxury vinyl plank flooring, tiled bathrooms, interior doors, recessed lighting, ceiling fans, and more. Relax or entertain on the custom oversized front porch that stretches the entire length of the home, creating the perfect outdoor living space. Don't miss this move-in-ready propertyschedule your private showing today!

1553 Hubbard Rd, Long Island
$175,000
3 Beds ⋅ 1 Baths ⋅ 368156 MLS
Welcome to 410 S Franklin Blvd, a charming 3-bedroom, 1-bath home offering nearly 1,500 square feet of comfortable living space right in the heart of Gretna. Set on a spacious corner lot, this home enjoys a prime central location with easy access to local shops, dining, schools, and everything the town has to offer. The generous square footage provides plenty of room to spread out, entertain, or make it your own, while the corner setting brings extra yard space and great curb appeal. Whether you're a first-time buyer, looking to downsize, or searching for a solid investment in a well-established community, this Gretna gem checks all the boxes. Don't miss your chance to own a piece of small-town charm with unbeatable convenienceschedule your showing today!

410 S Franklin Blvd, Gretna
$95,000
368085 MLS
Escape to the beauty of Leesville Lake with this stunning 2.3-acre waterfront homesite in the desirable Hernon Pointe community. Offering a peaceful setting with mature hardwoods and plenty of privacy, this property provides the perfect backdrop for your custom dream home or weekend retreat. Enjoy direct lake frontage, breathtaking natural surroundings, and the freedom to build when you're ready. Hernon Pointe offers a welcoming lake lifestyle with convenient access to boating, fishing, swimming, and all that Leesville Lake has to offer. Whether you're seeking a quiet getaway or a place to create lasting family memories, this exceptional lot combines space, serenity, and waterfront living in one incredible opportunity. Schedule your private tour today and start envisioning life at the lake!

52 Heron Pointe Rd, Gretna
$24,650
368046 MLS
Come enjoy land in an established lake community! Property offers tons of privacy with mature trees from start to end. The front of the lot has steeper terrain, with the back of the lot offering an elevated flat. The elevated flat could be a possible build site. In the bottom, you can find North America's largest native fruit trees, the custardy Pawpaw. Whether looking for a place for a cabin, a tent camping get away, or your primary residence and a piece of nature- take a look.

Leesville Lake Dr, Pittsville
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