Charlottesville 19th Century Homes for Sale

The Jordan Gilmer House

Year Built: 1806

Fabulous Historic Victorian home in the North Downtown mixed use corridor, currently used as a residence, with offices. With its gracious double front porches, and views to Monticello, it was built for Jordan Gilmer by an apprentice to Thomas Jefferson, and is so close to the Historic Downton Mall. With the historic crown-molding and door/window trims, rooms have the original exposed beams, and 10' ceilings. The location is perfect for easy access to Downtown, The University, UVA Medical Center & all N, S, W & E routes to/from town. Built in 1806, w/renovations in 1885, 1907 (and in more recent years!). Ample parking in the rear of the property. There are 12 spacious rooms to be configured in many ways, and four charming interior staircases.

Details about The Jordan Gilmer House

$1,390,000.

For more information contact Gayle Harvey Real Estate at 434-220-0256 or E-mail us!

Darby Rd

Year Built: 1820

Darby’s Homestead If these walls could talk…nestled adjacent the “Great Valley Road”, which is now called US Rt 11. The main homestead was built around the 1820 era. A vintage framework with newer “fixins”. Ie roof, septic, plumbing, electrical, HVAC, paint, windows, trim, cabinetry & fixtures. US 11 separates the homestead into 2 parcels. Total over 4.5 acres. Garden space & year round creek. Large red barn currently used for storage. 2 separate paddocks, each with automatic waterers. This homestead exudes a country flare while still offering close proximity to town amenities, the Appalachian Trail & National Forest.

Details about Darby Rd

$449,000.

For more information contact Gayle Harvey Real Estate at 434-220-0256 or E-mail us!

Frascati

Year Built: 1823

Frascati, c. 1823. Here is an exceedingly rare opportunity to acquire a national landmark perfectly located on 62.74 acres in the Somerset estate area of Orange County. Frascati was built for Philip Barbour, Associate Justice for the Supreme Court by John Perry, known for his work for Thomas Jefferson in building the University of Virginia and Monticello. Frascati is on the National Register of Historic Places and is a Virginia Historic Landmark. For a full history and architectural details about Frascati please see the Wikipedia listing in the documents section. In addition to the manor home the restored summer kitchen now serves as a charming guest cottage, the original formal gardens still exist with magnificent 200 year old boxwoods and extraordinary specimen trees. A lovely gunnite swimming pool is tucked away in a "secret garden" The 62 acres with Frascati is mostly open in high quality pasture and is suitable for any agricultural pursuit. There are several useful barns and sheds. The gently rolling land boasts superb views of the Blue Ridge mountains and is surrounded by large farms. Frascati is protected with a conservation easement with the VOF and The Virginia Board of Historic Resources. (See Documents).

Details about Frascati

$2,750,000.

For more information contact Gayle Harvey Real Estate at 434-220-0256 or E-mail us!

Orchard Rd

Year Built: 1825

Discover an extraordinary 35-acre property nestled within walking distance of historic Lovingston, VA in picturesque Nelson County. An easy 30 drive to both Charlottesville and Lynchburg, UVA, Wintergreen Resort, and the most beautiful wine country on the East Coast. This unique property is a canvas for limitless possibilities: turn it into a beautiful venue, a glamping retreat, or even subdivide for future development. Recent upgrades have laid the groundwork, making it ready for your vision. Including a 2024 Timberwolf Camper for a turn key short term rental, Permited 50 amp Electrical Panel, cleared walking trails to the top of the property with natural springs and heavenly views!

Details about Orchard Rd

$449,000.

For more information contact Gayle Harvey Real Estate at 434-220-0256 or E-mail us!

Glen Haven Farm

Year Built: 1832

Discover Glen Haven Farm, a 49.03-acre estate established in 1832, set along the Cowpasture River, one of the cleanest rivers on the East Coast. Once home to the Jordan family, this historic property offers modern amenities, including a 4,824 sq ft farmhouse with 4 bedrooms, 3 baths, and a one-bedroom apartment. The property features a rustic, industrial-chic 3,500 sq ft event barn, a river pavilion, a performance stage, a 5,000 sq ft industrial workshop, a 1-acre commercial hop yard, and low-light conditions ideal for stargazing. Operating as a venue since 2017, Glen Haven hosts 20+ weddings and events annually, including fireworks shows. The property comes fully furnished, includes farm equipment, and a primitive campground with potential for expansion. Located within 3 hours of D.C. and 1.5 hours from Charlottesville, Glen Haven Farm blends historical charm, business success, and natural beauty, ready for its next chapter.

Details about Glen Haven Farm

$3,900,000.

For more information contact Gayle Harvey Real Estate at 434-220-0256 or E-mail us!

Spring Hill Farm

Year Built: 1837

Welcome to Spring Hill Farm, an exceptional 294-acre farm located in Virginia's horse country in Culpeper County. Just an hour’s drive from Dulles International Airport, this property is perfect for those seeking country living with close proximity to city amenities. The town of Culpeper with its wonderful restaurants is a quick 15 minute drive. Spring Hill consists of mostly open pastures with 93+/- acres in productive cropland. While the farm is currently utilized for livestock & crops, it has the potential to be an incredible horse farm located near several foxhunts. Should you prefer to enjoy the farm lifestyle without the work, the current farmer would love to continue to lease the farm & help to maintain its current low real estate taxes. The historic circa 1837 farmhouse blends old home charm with modern comforts, including 3 bedrooms, 2 updated bathrooms & a spacious country kitchen. You’ll love the stunning Blue Ridge Mountain views while relaxing on the front porch & the peaceful setting overlooking the rolling pastures from the rear deck. If you have been dreaming of a beautiful farm, Spring Hill is a must see!

Details about Spring Hill Farm

$3,850,000.

For more information contact Gayle Harvey Real Estate at 434-220-0256 or E-mail us!

Brownsville Rd

Year Built: 1839

Welcome to this charming historic home in Crozet, built in 1839 and set on 1.38 acres. Enjoy stunning Blue Ridge Mountain views from the fully fenced yard, complete with a greenhouse/workshop and a peaceful Koi pond. Conveniently located just 25 minutes from Charlottesville and 7 minutes from downtown Crozet, you’ll also find breweries and a grocery store just 5 minutes away. The home features a spacious front deck ideal for relaxation, a primary bedroom with impressive 12-foot ceilings, and an updated kitchen with modern flooring. This unique property beautifully blends historic charm with modern conveniences—don’t miss your chance to make it yours!

Details about Brownsville Rd

$565,000.

For more information contact Gayle Harvey Real Estate at 434-220-0256 or E-mail us!

Anwesen

Year Built: 1846

Escape to Virginia's Piedmont, the Madison-Barbour Historic District & live in Orange County horse country. 294 acres of pasture & timber (protected by Virginia Outdoors Foundation easements) surround our 1850's Italianate 4 bedroom home w/ few modifications (ready for a new owner to personalize). The front & rear porch views of the lawn/gardens, pasture, woods & mountains remain breathtaking. The English basement opens to a patio garden w/ Blue Ridge Mountain views. Come see the large rooms, intricate woodwork, fireplaces, wood floors, handmade peg doors, & 1850's craftsmanship throughout the home. Old farm buildings & horse barn have potential for repurposing to meet your needs. Showings by appointment only.

Details about Anwesen

$1,999,797.

For more information contact Gayle Harvey Real Estate at 434-220-0256 or E-mail us!

Greenville

Year Built: 1854

One of the State’s finest examples of Classical Revival/Neoclassical architecture, sited on 716-acres of rolling, highly productive crop land and pasture land with nearly 1.5 miles of frontage on the Rapidan River. The home is instantly recognizable with its 4 massive Doric columns and “M” shaped copper roof. Built in 1854, the well-proportioned residence with 11+ foot ceilings was meticulously restored by high-end contractor, Alexander Nicholson, to its present condition. The restoration kept the original doors, mantels, woodwork, and most of the heart pine floors intact. Listed on the National Register and VA Landmarks Register. The Rapidan River and its lowlands offer endless recreation including canoeing/kayaking, fishing and some of the area’s best duck hunting (enhanced by duck impoundment pond). Additional improvements include a restored, period summer kitchen/office, guest cottage, conservatory, pool and pool house, stables, managers cottage and farm infrastructure.

Details about Greenville

$6,995,000.

For more information contact Gayle Harvey Real Estate at 434-220-0256 or E-mail us!

Upper Stony Run

Year Built: 1875

Very charming home built sometime mid to late 1800's, retaining the original wavy glass windows, heart pine floors and clapboard siding. Situated near the base of the Blue Ridge Mountains in WAlbe, the views are stunning and sunrises and sunsets are spectacular. The 9.44 acres has Stony Run at the rear as well as a spring that historically provided water to numerous homes in the area via a ram pump and then stored in a concrete cistern that is still on the property. There is an old partially log structure in disrepair and we ask that no one goes into the structure because of it's condition. The adjoining homes in the area are of very high quality. There is a possibility that this land could be divided and two more building sites developed if all the county approvals are met. The metal roof was replaced in 2013 and the forced air furnace around 2013. An addition in 2004 added a large mud room, full bath, laundry area, side deck. The entire interior has been painted and plaster repaired. None of the fireplaces are in working order. The chimney tops were re-pointed in 2013 prior to the new roof going on. The home, all appliances & outside structures are sold in "as is" condition. The home needs continued restoration but worth it.

Details about Upper Stony Run

$750,000.

For more information contact Gayle Harvey Real Estate at 434-220-0256 or E-mail us!

New St

Year Built: 1880

Available for the first time since being meticulously renovated and restored to its historic grandeur. Built in 1880 and completely overhauled in 2018, this National Historic Register five bedroom home provides wonderful modern day amenities coupled with charm, luxury, and excellent proximity to town. Walking through the front gate you are greeted by a covered porch and a light filled foyer that showcases common themes throughout: tall ceilings, beautifully restored hardwood floors and mantels, stained glass windows, detailed trim work & moldings, updated systems, lovely chandeliers, and attention to detail. The eat-in kitchen features quartz counters, new appliances & cabinets, a charming bay window, and pocket doors to the elegant dining room. The curved staircase sweeps you up to the remarkable primary bedroom suite with soaking tub, dual vanity, and walk-in closet. Two additional bedrooms and easy access to the private rear porch complete the second floor. The bedroom suite on the main level, and the terrace level apartment offer flexibility as rental income or family use. Attractive garden space, private parking court, and a detached garage behind the house. A significant offering in the heart of storybook Staunton, VA.

Details about New St

$1,195,000.

For more information contact Gayle Harvey Real Estate at 434-220-0256 or E-mail us!

Shenandoah Manor Bed & Breakfast

Year Built: 1883

Presenting Shenandoah Manor, a historic Bed & Breakfast poised near vibrant downtown Lexington in the sought-after Shenandoah Valley. Nestled on 10 serene acres with rolling meadows, a scenic pond, and a creek, this property is perfect for a hospitality business, offering modern amenities like fiber internet and reliable cell service. The main house features three guest rooms, each with private bathrooms and balconies, expansive owners' quarters, two versatile studio spaces, a cozy library/music room, and a well-equipped kitchen. A separate guest house adds five more guest rooms with private bathrooms, a kitchenette, and a living room. A stone patio connects both houses, offering a perfect outdoor setting for gatherings, complete with a campfire area. The estate is ideal for various ventures, from vineyards and wedding venues to hosting events with its flat area for tents, a gazebo by the pond, and ample parking. Suitable for any kind of retreat—yoga, wellness, corporate, or artistic—the property is ready for new ownership, with the option to purchase furnishings. Own and operate a distinguished venue in a desirable location.

Details about Shenandoah Manor Bed & Breakfast

$998,900.

For more information contact Gayle Harvey Real Estate at 434-220-0256 or E-mail us!

Old Spring Hill

Year Built: 1888

Private estate minutes from Charlottesville and the University with wonderful Blue Ridge views. The 1888 traditional farm house has been completely renovated and decorated by well known interior decorator, yet retains the charm and woodwork of the original house. The main house includes 3 bedrooms with private baths, large kitchen with high end appliances, family room, large living room with fireplace. Other improvements include a new guest / pool house, pool, and 2 car detached garage with a charming office. Also includes a small tenant / manager cottage. All improvements are beautifully situated on the 21 acres with complete privacy.

Details about Old Spring Hill

$3,950,000.

For more information contact Gayle Harvey Real Estate at 434-220-0256 or E-mail us!

Zinks Mill School Rd

Year Built: 1890

Come and enjoy the cool and picturesque mountains of Montebello! Once a thriving family farm, (with fruit trees still remaining), the land is flat and rolling, so there's no worry about steep mountain roads. The long drive from the state maintained road takes you to the original farmhouse that has been lovingly restored and renovated inside and out. The renovations over the last ten years, from the hardie plank siding, new deck, new kitchen, new windows, HVAC, just to name only a few, are very extensive, so please see the enclosed addendum. The character of the home, with original heart pine floors throughout and shiplap siding in the living room, for example, speaks of another time. Please note that there is a full attic that can be utilized for renovation. The home is surrounded by a creek, with natural, preserved habitat on one side, and lovely yard and fields. There's also a garage, carport and shed. The location here is minutes from the Montebello store, and the Blue Ridge Parkway, and the Tye River and the Crabtree Falls National Park are close by. With this NEW PRICE, the owners' recognize that the new purchasers may want to continue the renovations to suit their taste.

Details about Zinks Mill School Rd

$495,000.

For more information contact Gayle Harvey Real Estate at 434-220-0256 or E-mail us!

Historic Hemlock House

Year Built: 1890

Renovated 4 bedroom 2 bathroom Historic Hemlock House located in North Garden. This home has a spacious living room with a fireplace, formal dining room, eat-in kitchen with island, granite countertops, and back stairwell leading upstairs to the bonus room. The master bedroom and 2nd bedroom upstairs both have a fireplaces. There is an open foyer, original hardwood floors throughout, ceramic tile in both bathrooms, and a newly added laundry room. There is a mudroom at the back entrance and a mini wine pantry area off of the kitchen. Includes a 200 amp electrical service (2020), heat pump (2020), well pump (2022), appliances, light fixtures, and ceiling fans in most rooms. Large country front porch with hanging swing and Piedmont mountain views. Outdoor sitting area. This is the perfect area for an Airbnb or Bed & Breakfast surrounded by mountain views and vineyards. Seller will provide home warranty through AHS for 1 year.

Details about Historic Hemlock House

$585,000.

For more information contact Gayle Harvey Real Estate at 434-220-0256 or E-mail us!

James River Rd

Year Built: 1890

A rare opportunity to unlock the door to history with this captivating Circa 1890 estate that offers more than just a home; it provides an opportunity to own a piece of the past. Nestled on sprawling acreage with lots of road frontage, this property boasts an exceptional combination of old-world charm and modern convenience. Wake up to the awe-inspiring beauty of the Blue Ridge Mountains every morning. The unobstructed views from this estate are truly a sight to behold. Experience the tranquility of life by the water with the convenience of walking to the nearby James River. Perfect for fishing, kayaking, and relaxation. Nature enthusiasts will appreciate the abundance of wildlife on this estate. You will have a front-row seat to the wonders of the natural world. A new roof has been put on home.

Details about James River Rd

$950,000.

For more information contact Gayle Harvey Real Estate at 434-220-0256 or E-mail us!

501 W Frederick St

Year Built: 1892

****Charming Historic Home in Prime Staunton Location**** Discover timeless elegance in this circa 1900s home, built in 1892, nestled in the heart of Staunton, VA. This beautifully preserved residence seamlessly blends historic charm with modern conveniences, creating an inviting and versatile living space. The heart of the home, the kitchen, boasts new smart appliances, ensuring your culinary adventures are both efficient and enjoyable. Recent updates include a new roof, gutters, and gutter guards installed in 2023, offering peace of mind for years to come. The encapsulated basement, also completed in 2023, provides a clean and dry space, ideal for storage or future expansion. Step inside to find freshly painted walls that breathe new life into every room. The freshly sanded hardwood floors add a touch of sophistication, leading you through the spacious and light-filled interiors. The newly renovated master bathroom offers a serene retreat with modern fixtures and finishes. This home’s versatility is a standout feature. Canbe utilized as an Airbnb, it can effortlessly transition back into a lucrative rental property.

Details about 501 W Frederick St

$535,000.

For more information contact Gayle Harvey Real Estate at 434-220-0256 or E-mail us!

Brownsburg Tpke

Year Built: 1893

Charming 86-Acre Farmstead with Stunning Views Welcome to your dream retreat! This beautiful 86-acre small farm offers a perfect blend of tranquility and convenience. Nestled in a serene setting, this property features an exquisite 1893 farmhouse, boasting five spacious bedrooms and three full bathrooms, ideal for family living or entertaining guests. The farmhouse exudes classic charm with modern comforts, making it a cozy sanctuary. Enjoy breathtaking views from every angle, whether you're relaxing on the porch or exploring the expansive grounds. This property is equipped with multiple outbuildings and barns, providing ample space for storage, hobbies, or even livestock. Dive into relaxation with your very own heated swimming pool, perfect for summer days and entertaining friends and family. While this idyllic farm offers peace and privacy, it remains conveniently located near essential amenities. Experience the best of both worlds—a serene lifestyle with easy access to shopping, dining, and recreational activities. Don't miss out on this rare opportunity to own a piece of paradise! Schedule your private tour today and start envisioning your life on this incredible property.

Details about Brownsburg Tpke

$1,399,000.

For more information contact Gayle Harvey Real Estate at 434-220-0256 or E-mail us!

Rugby Rd

Year Built: 1896

Located on historic Rugby Road, this stately circa 1896 home offers timeless elegance and modern convenience, all within an easy walk to The Corner, UVA Grounds, Downtown, and Barracks Road Shopping Center. Set on a large lot framed by mature trees and landscaping, the home features flowing, light-filled rooms that capture its rich history and charm. Pocket doors, built-in bookshelves, and crown moldings are just a few of the intricate design details that make this home truly special. With 5 bedrooms, 4 baths, and a beautiful library, this residence is a rare find and a must-see.

Details about Rugby Rd

$1,995,000.

For more information contact Gayle Harvey Real Estate at 434-220-0256 or E-mail us!