Charlottesville 20th Century Homes for Sale

Awesome Valley View Farm

Year Built: 1900

AWESOME well maintained farmhouse sits on over 86 expansive acres! This property embodies the idyllic farm setting you've always envisioned, complete with stunning Blue Ridge Mountain views. Farmhouse features 2600+ sqft, spacious detached garage with bonus room, silo, barn, wooded areas, lush pastures with tree-lined fencing, ponds, and abundant wildlife for hunting enthusiasts. The main house welcomes you with a broad front porch offering a perfect vantage point for enjoying sunsets. Inside, you'll find soaring ceilings, generously sized rooms, and mountain views from nearly every room. Foyer leads to cozy living room that seamlessly transitions into an eat-in kitchen. Formal dining room showcases views of Massanutten, while a first-floor bedroom and bathroom add convenience. The mudroom, also on first level, includes laundry closet, and a back staircase leading to the primary bedroom upstairs. The second floor houses a total of 3 bedrooms, including a primary bedroom en-suite. Relax in the evenings in the hot tub or by the firepit on the back patio to unwind. This property is conveniently located near various outdoor activities, wineries, and Massanutten Resort. FULLY FURNISHED & TURN KEY. Owner financing possible.

Details about Awesome Valley View Farm

$1,295,000.

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

Five Petals

Year Built: 1900

Renovated TRIPLEX on large/main house PLUS A DETACHED furnished 650sqft COTTAGE built in 2015. COTTAGE is tucked on the back of the .20 acre landscaped lot, offers great privacy, all one level living, laundry room, off street parking. Cottage and 2 or 3 units in triplex are nicely furnished short term rentals,(will convey furnished) been successful short term rentals for travel nurses/UVA professors (30-90 day leases),working professionals. The 4th unit a 2 bed/1 bath is rented unfurnished offers a nice large front porch, updated bath/kitchen, HVAC. All three FURNISHED rentals convey FULLY furnished and have one off street deeded parking spot. Property is in excellent condition and leases in place into spring 2025. New City zoning, property can have 6 units By-Right, OR reconfigure to a single family keeping the Cottage as a rental/STR. Walk to DT, Belmont Restaurants, all units have porches/decks/privacy. Cottage was built in 2015 by Class A contractor, with permit. Lots of Updates and improvements. Lot is .20 and nicely landscaped, all units have great privacy, their own entrances and porches, no shared mechanicals. Has been successfully rented since 2014, guaranteed income into spring 2025.

Details about Five Petals

$1,595,000.

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

Cedar Springs Farm

Year Built: 1900

Cedar Springs Farm is located in one of the most desirable and scenic areas of Central Virginia. There are several local wineries and brewery's close by. Graves Mountain Lodge and the Shenandoah National Park are within a few minutes drive. It is a rarity that such an uniquely exceptional property is available to the market. Nestled in Dulaney Hollow, and adjacent to a spring, is a circa 1900 two story farmhouse, in good condition. The five bedroom, one bath, house has a standing seam metal roof, wood siding, stone foundation and patio. In addition there are two wood burning fireplaces. A natural spring provides water to the house, and there is a septic system drainfield. Being strictly sold in "AS IS" condition. Frontage on two State roads. Property is in Forestal and Agricultural Land Use Taxation. Several small creeks, springs and pond on property. Very private yet accessible farm with un-paralleled rolling pastures and views of Old Rag Mountain, from several potential building sites.

Details about Cedar Springs Farm

$2,250,000.

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

Sedwick

Year Built: 1900

Recorded as 100 acres. Sellers selling as recorded without any adjustment for acres and houses and buildings being sold "as is" There is a small pond on the property as well as sheds and other buildings. Showings only by appointment with agent. Most all wooded with trail up the ridge. Hunting rights are leased. Ideal retreat or private living with state maintained road much of which has been recently paved.

Details about Sedwick

$525,000.

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

Awesome Valley View Farm

Year Built: 1900

AWESOME well maintained farmhouse with mountain views on 1.7 acres. This property embodies the idyllic farm setting you've always envisioned, complete with stunning Blue Ridge Mountain views. Farmhouse features 2600+ sqft, spacious detached garage with bonus room and barn. The main house welcomes you with a broad front porch offering a perfect vantage point for enjoying sunsets. Inside, you'll find soaring ceilings, generously sized rooms, and mountain views from nearly every room. Foyer leads to cozy living room that seamlessly transitions into an eat-in kitchen. Formal dining room showcases views of Massanutten, while a first-floor bedroom and bathroom add convenience. The mudroom, also on first level, includes laundry closet, and a back staircase leading to the primary bedroom upstairs. The second floor houses a total of 3 bedrooms, including a primary bedroom en-suite. Relax in the evenings in the hot tub or by the firepit on the back patio to unwind. This property is conveniently located near various outdoor activities, wineries, and Massanutten Resort. FULLY FURNISHED & TURN KEY. Owner financing possible. Additional 85 acres adjoins property and is available as well.

Details about Awesome Valley View Farm

$584,900.

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

Belmont Ave

Year Built: 1900

Great house in an optimal location! A flagship victorian on one of the best blocks of the desirable neighborhood of North Belmont. The 3 bedroom 2 bath house has wonderful sunny rooms and spaces, and features a copper roof with integral gutters, metal siding, paved driveway, rear deck, wrap around porch, attic and basement space, and dual fuel zoned central AC/heat. Freshly renovated by architect owner with new floor plan, features, appliances and fixtures. New storm windows for the entire house. Extra upstairs room can be a small bedroom, office, nursery, or an additional or ensuite bathroom next to the primary bedroom. Walk around the tree lined block to the popular downtown Belmont, neighborhood parks, and local schools and churches, or stroll just several more blocks to downtown Charlottesville. Rare opportunity for an exceptional property. The real deal!

Details about Belmont Ave

$825,000.

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

Greenfields Farm

Year Built: 1904

Greenfields is an historic Southern Albemarle hunting & farming estate ideally suited to outdoor enthusiasts incl' equestrians, wing shooters (turkey, dove, ducks, released quail), deer hunters & anyone who might want to take advantage of the fertile croplands. The centerpiece of this storied property is a c.1905 manor home offering 12ft ceilings, incredible woodwork, massive windows, endless fireplaces & also modern luxuries incl' his & per primary suite bathrooms & an expansive, modern kitchen. There are 3 modern, 1 bedroom aprtmnts in excellent cond. for guests or staff. In an area of noted farms & estates 25 mins from Charlottesville. Along Ballenger Creek sits the remains of Boiling Springs Grist Mill (photos in slide show), constructed in 1780 to grind local landowners' corn & whole wheat w/ millstones imported from Italy. During the Civil War Sherman's troops intended to burn the mill down however then owner WH 'Buck' Langhorne's slave Peter Jefferson poignantly & successfully pleaded that it be spared. The mill & Greenfields Farm have been owned or visited by many prominent Virginians well into the mid 1900's incl. Nancy Astor, 1st female member of the English House of Commons. 2 div. rights. Add'l 258 acres avail.

Details about Greenfields Farm

$4,250,000.

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

Advance Mills Rd

Year Built: 1905

OPEN HOUSE. SAT. MAY 11th. 12-3 PM! Step into a world of living history within this meticulously updated and renovated classic farmhouse. Surrounding the home is a haven of privacy & stunning hardwoods, and a rich variety of plantings. The expansive porches, decking & patios embrace the residence, affording multiple vistas of the lush yards & glimpses of the shared pond nestled just beyond the rear yard. The detached garage is accessible to house by patio. Upon entering the home via the covered front porch, the sense of history is evident by the fireplaces and the charm of historic homes. The kitchen merges w/the dining area & sunroom that offers a view of the backyard. The 1st floor is the primary bedroom and is joined by an updated bath. The main staircase leads to the 2nd floor foyer & opens the way to 3 additional bedrooms and a full bath. The largest of these could easily double as an upstairs family room for more living space. An additional staircase connects the larger bedroom to the kitchen area at the rear of the home, adding a touch of character. Exceptional upkeep and profound care; the current owners have meticulously maintained the property. The grounds also feature multiple outbuildings.

Details about Advance Mills Rd

$799,500.

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

High Fields

Year Built: 1908

Discover the charm of this picturesque 42-acre farm, just a scenic 10-mile drive from Charlottesville. Nestled amidst rolling pastures and tranquil woodlands, this property boasts a serene creek meandering through its expanse, alongside an enchanting antique farmhouse (c.1908). Step inside to find a tastefully updated kitchen, featuring modern wood cabinets and stainless steel appliances, complemented by three beautifully renovated bathrooms and four generously-sized bedrooms. Breathtaking elevated plateau, offering panoramic vistas of the Blue Ridge Mountains. Wake up to awe-inspiring sunrises and winding down with stunning sunsets from your future dream home perched on this majestic vantage point. Additionally, the property features a substantial barn, perfect for various agricultural pursuits, making it an ideal setting for those seeking a manageable-sized farm with the convenience of close proximity to town.

Details about High Fields

$1,695,000.

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

La Abra Farm

Year Built: 1910

La Abra Farm, an 80 acre family farm offered for the first time in 50 years. Site of Virginia's oldest winery, Mountain Cove (winery business sold separately), La Abra is well situated to meet your farming needs. In addition, the property has a Special Use Permit for 20 self-contained RV farm stay sites! The land is composed of three distinct parcels with approximately 28 acres of woodland, 44 acres of pasture and 8 acres of fenced vineyard. The farm is well watered by streams including Dillard Creek. The 4 bedroom, 2 bath renovated farmhouse is complemented by a full array of farm outbuildings. You'll find a 27 x 72 stone "wine cellar" with room for farm events that's accompanied by a 17 x 25 farm office/visitor center, a significant 18 x 40 building used by the winery for production, as well as a variety of vintage farm buildings such as a corn crib, tobacco barn, two story office and more.

Details about La Abra Farm

$1,395,000.

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

Hillcrest Mansion & Inn

Year Built: 1910

Imagine waking up to stunning mountain view? Embrace history and opportunity at the Hillcrest Mansion Inn, a turn-of-the-century gem in Virginia's breathtaking mountains. This versatile property thrives as a successful B&B with 7 ensuite guest rooms, each promising an unforgettable stay. Imagine inheriting a turnkey operation boasting excellent reviews and a loyal clientele. But the possibilities extend beyond hospitality. Convert the mansion into a luxurious private residence, unwinding in a bygone era while enjoying modern comforts like high-speed Wi-Fi. A separate owner's quarters in the carriage house ensures privacy. The true star? The location. Hillcrest boasts mesmerizing mountain views, while charming Clifton Forge offers a vibrant small-town atmosphere. Adventure awaits just moments away: explore the George Washington National Forest, delve into history at the C&O Railway Heritage Center, or soak in the Warm Springs Pools. Hillcrest Mansion Inn – your chance to own a piece of Virginia's legacy. Live in a luxurious mountain setting, operate a thriving B&B, or create a private haven. Contact us today to explore the possibilities! Ask for improvement list - ~300K in noted renovations!

Details about Hillcrest Mansion & Inn

$2,000,000.

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

1st St

Year Built: 1910

Welcome to this charming historical home nestled 3 blocks from the Downtown Mall! This cute gem has captivating features and is ready for move in. It presents a fantastic opportunity for those seeking a prime location and the chance to customize their dream space. Step onto the private deck and soak in the serene surroundings. The Craftsman style and delightful coke bottle door windows exude unparalleled charm that will make you fall in love at first sight. Embrace the cozy atmosphere and appreciate the elegant moldings and stunning hardwood floors that grace the interior. With so much to offer, this home eagerly awaits your personal touch.

Details about 1st St

$625,000.

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

Hillview Farm

Year Built: 1911

Step back in time and experience the charm and beauty of this 1911 farmhouse that has been fully renovated in 2000. This picturesque home boasts three bedrooms, two bathrooms, and is surrounded by mature trees and landscape that will take your breath away. The equine facility is fully equipped and ready for horses with 15 matted stalls featuring rubber brick aisle, PVC safety bars, and six laned paddocks. Riders choose between a river bottom sand surface in the arena, or the turf jump field. The property offers unbelievable 365° mountain views of North Mountain, Green Hill, and the “saddle” between the House Mountains. Whether you're sipping your morning coffee on the back patio, or enjoying the sunset from the front porch, you'll never tire of the natural beauty that surrounds you. The original milking barn was renovated into a 1 bedroom 1 bath apartment that also has an attached lounge and half bath. Don't miss out on this one-of-a-kind property that perfectly blends history, modern amenities, and natural beauty. Come see for yourself and make this farmhouse your own piece of paradise.

Details about Hillview Farm

$1,200,000.

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

The Boone-white House

Year Built: 1914

One of Charlottesville's premier properties, tucked away on a private .28 acres, a few blocks to UVA main grounds, hospital & Scott Stadium. This historic property includes a flawlessly renovated c. 1914 Tudor Revival home, designed by noted architect Eugene Bradbury AND a fabulous 1,100 square foot, 2 bedroom, 1.5 bath guest cottage. Exquisite details include: expertly re-plastered & painted interior walls, arched openings, painted hardwood floors, restored exterior (stucco, trim, paint), 4 fireplaces, true divided light windows, elegant dining & living spaces including an all-glass "conservatory" overlooking the gardens. Impressive landscaping features numerous stone walls, terraces, mature plantings & trees (don't miss the towering redwood!) designed by Orland E. White, who bought the home in 1928 & also designed the VA State Arboretum. The chic, c. 1930 guest cottage features a full kitchen, open living /dining spaces & delightful stone-walled courtyard. Spoil your guests or generate substantial income through long or short term rentals. Unique opportunity to own a remarkable property right in the middle of all things UVA!

Details about The Boone-white House

$1,485,000.

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

Valley St

Year Built: 1916

Exquisite Historic Residence in Downtown Scottsville. Impressive double porches, spacious rooms, and a potential guest cottage in the carriage house. Built by renowned Dr. Stinson, showcasing classic architectural details and hardwood floors. Reflecting the area's historic charm, Scottsville offers a blend of history and modern convenience. Enjoy a tranquil retreat within walking distance to the James River for kayaking, tubing, fishing and other outdoor adventures. Whether seeking a permanent residence, weekend escape, or investment opportunity, 550 Valley Street in Scottsville offers an ideal setting of a quaint small town in close proximity to Charlottesville and the University of Virginia.

Details about Valley St

$790,000.

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

Buck Rd

Year Built: 1920

It's about the land. These three parcels comprise an amazing opportunity close to downtown Crozet! Build your dream home on land that has not been on the market in decades. Walking distance to Downtown Crozet, Mint Springs and so much more! The house itself needs work, and could be a great spot to fix up and live in while building your dream home, or fix up and rent as an income property

Details about Buck Rd

$1,000,000.

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

Park St

Year Built: 1920

Discover an unparalleled opportunity on prestigious Park Street, mere steps from Charlottesville’s vibrant Pedestrian Mall. This unique property offers versatile possibilities: transform it into an elegant private residence, maintain its current use as legal or office space, or envision an innovative mixed-use development. Boasting expansive rooms, lofty ceilings, architectural detailing, and ample rear space, this historical gem beckons a transformative vision. A private parking area for approximately 16 vehicles complements the property, while a covered front porch affords views of Park Street and immediate access to renowned dining, cultural amenities, and boutique shops. Situated less than two miles from the University of Virginia.

Details about Park St

$1,195,000.

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

Stunning Historic Home In Downtown Charlottesville

Year Built: 1920

Extremely rare opportunity to live on one of Downtown Charlottesville’s premiere streets just a few scenic blocks from city parks, restaurants and shopping. 1920’s character abounds in this charming light-filled home that offers original woodwork, moldings and hardwood floors, dramatic foyer with fireplace, tall ceilings, deep welcoming front porch, and a truly remarkable backyard oasis with swimming pool and wonderful entertaining spaces. 5 bedrooms and 3.5 baths, including a first floor primary suite/bath, and an elevator that services the main level and partially finished basement. With a little creativity, the walk out basement could become an in-law suite, nanny space, or teen hang out. Beautifully landscaped yard features large shade trees, mature plantings, plenty of lawn, and three off-street parking spaces! So much to love about this gorgeous home as it is, with endless opportunities awaiting a new owner’s personal touches. Offered for sale for the first time in over 40 years, this stunning residence presents a unique opportunity in an unbeatable location. Easy access to Main Street, UVA Hospital, UVA Grounds, Interstate 64, and the 250 corridor.

Details about Stunning Historic Home In Downtown Charlottesville

$1,395,000.

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

Batesville Rd

Year Built: 1920

Great small home, 1920's vintage, currently leased through 6/15/2024; the property consist of 123.13 acres. 120.13 acres in conservation easement with the potential for 2 dwellings and associated allowed dependencies. 8233 Batesville Road is a adjacent parcel, TM 84, parcel 11 containing 3 acres. Great woodland and creek area reaches up the mountain ridge behind the property. Two gorgeous knolls behind the existing home can accommodate new construction. 24 hours notice needed to show. Good timber value on the property in a forestry lease. See documents for additional information. See MLS # 650773 for additional information and photos.

Details about Batesville Rd

$1,750,000.

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

Howardsville Rd

Year Built: 1920

Welcome to your dream country estate! Nestled on 23 sprawling acres, this charming property offers the perfect blend of modern amenities and rustic charm. As you approach the house, you'll be greeted by the grandeur of a magnificent magnolia tree and a majestic maple tree adorning the front yard, setting a picturesque scene. Step inside to discover a meticulously maintained 4-bedroom, 2-bathroom home that's sure to impress. The spacious living room boasts elegant plantation shutters, inviting you to relax in style, while the warm wood floors add a touch of sophistication. Adjacent to the living room is a cozy dining room featuring a charming bumpout, ceiling fan, and more of those beautiful wood floors. Prepare to be wowed by the recently renovated kitchen, a chef's delight with granite countertops, a massive center island equipped with a wine fridge and rack, stainless steel appliances, and a convenient gas stove. Whether you're hosting a dinner party or whipping up a quick meal, this kitchen has everything you need. For those cozy evenings in, retreat to the den or unwind on the covered deck complete with fans and access to the hot tub and fenced dog yard, where your furry friends can roam freely.

Details about Howardsville Rd

$674,999.

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

New Antique Home Listing in Rappahannock!

Lee Hwy

Year Built: 1920

Restored farmhouse on 4+ acres in beautiful Rappahannock Co. Features main level gallery style living and dining rooms, 4 season sunroom, entry hall, and farmhouse style kitchen. Upper floor features 2 spacious bedrooms and newly renovated bathroom. Terrace level features Bedroom, Bath/Laundry, sunroom, large den/rec room. Owner/Licensee.

Details about Lee Hwy

$715,000.

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

Cherry Ave

Year Built: 1925

An exciting investment opportunity to own a property with side street access that allows up to 6 units in the new R-B zoning. Due to its excellent location, the property has been a very successful rental. Walking distance to downtown, UVA, West Main and Smith Aquatic Fitness Center. Cherry Ave is located on a bus route. It is a short drive to I-64 and 5th street station. There are four, potentially five(smaller vehicles) off-street parking spaces, making this a very desirable rental. Home has been well maintained and loved by long-term tenants. This spacious downtown home features hardwood floors, a metal roof, AC, updated windows, large bedrooms and a master bedroom on the first floor. This home has a large backyard and a garage/workshop/storage area with power.

Details about Cherry Ave

$475,000.

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

9th St

Year Built: 1925

Great development opportunity with RN-A zoning which allows a property owner to get up to FIVE units on one lot by preserving the existing building on the site while building a new one with 3 additional units. Curb cut out already in place. Could get possibly more units on the lot if the bonus units are affordable to households at 60% of the local Area Median Income. Walking distance to Dairy Market makes this a great opportunity! Home remodeled in 2005 and new tin roof installed at that time. Has been used as a rental for University students.

Details about 9th St

$549,000.

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

7th St

Year Built: 1925

**Rare Find in Charlottesville!** Welcome to the perfect blend of charm and convenience in this beautiful 1925 home located between Downtown Mall and UVA offering a short walk to the train station, and restaurants.. 3 Bedrooms, 2.5 Bathrooms, Hardwood Floors Throughout, Mature Cherry Trees in the Front Yard, Fully Fenced Yard for Privacy. Incredible Zoning Potential for Additional Building on the Lot Don't miss this rare opportunity to own a piece of history with modern amenities and endless possibilities.

Details about 7th St

$649,900.

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

Lexington Ave

Year Built: 1928

Nestled in walkable North Downtown, this renovated historic gem boasts of charm and modern amenities. Situated on an elevated, professionally landscaped lot, the allure of this property is evident from the moment you step onto the inviting front porch. As you enter the foyer, you're greeted by the grandeur of nine and a half-foot ceilings, original hardwood floors, and the abundant natural light streaming through large windows. This meticulously crafted 3-bedroom residence offers a rare and luxurious first-floor owner's suite, complete with a generously-sized walk-in closet, a rejuvenating walk-in shower, and the cozy ambiance of a gas fireplace. The main living space boasts a desirable open floor plan and a newly renovated kitchen, providing the perfect setting for both intimate gatherings and lively entertaining. The converted porch offers a versatile flex space for an office, play nook, or hobby corner. Additionally, ample walk-in attic storage provides convenience and practicality, ensuring that every inch of space is utilized efficiently. Ample off street parking with Tesla charger in place. *R-B zoning. The unseen systems have not been forgotten with brand new HVAC (2023), water heater (2019), boiler (2016) and newer roof.

Details about Lexington Ave

$965,000.

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

Locust Ave

Year Built: 1929

Unbeatable location and move-in ready home on coveted Locust Ave in North Downtown Charlottesville. This classic brick home with great natural lighting on three levels has all the charm and character of an older home, beautifully balanced with renovated kitchen, baths, and energy efficient upgrades. Original woodwork, crown moldings, 9 foot ceilings, and built-in bookshelves. Professionally landscaped yard with mature plantings offers room for relaxation and entertaining. The home is perfectly situated on the lot for a thoughtful expansion. Exceptional primary suite with French doors easily convertible into two separate bedrooms if desired. A separate entrance and full basement bath are perfect for an in-law suite or convertible to a separate rental unit. Four private, off-street parking spots. Home is set up for Xfinity WiFi and Ting fiber internet is hardwired with connections & raceways for ethernet cables between cabinets on all three floors. Friendly and accessible community with wide streets and sidewalks. Quick access to UVA close proximity to Downtown. Recent upgrades: Energy efficient insulation (2024), New Roof (2022), replacement windows, Renovated Bathrooms (2023 and 2019), Exterior Painted (2022), new custom exterior

Details about Locust Ave

$949,900.

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