Charlottesville 20th Century Homes for Sale

Five Petals

Year Built: 1900

LOCATION! Three separate units in LARGE house PLUS A SEPARATE COTTAGE a total of 4 RENTALS. Cottage plus 2 of the 3 rentals in the main house are furnished rentals, will convey furnished, each furnished has a an off street parking spot. Cottage offers privacy, one level living, laundry room, hardwoods, central HVAC. A 30 day minimum lease for the STR- furnished units, AIRBNB allowed if owner lives on property. Furnished rentals popular with Travel Nurses/UVA professors. All units have excellent rental history, never vacant. One of the units in the main house is rented unfurnished offers a nice large front porch, 2 beds/1 bath a good size unit, updated bath, HVAC, large front porch and large living room. New City zoning, allows up to 6 units By-Right, OR reconfigure to a single family keep Cottage as a rental. OR live in the cottage and have 3 successful rentals. Cottage built in 2015 by Class A contractor w/permit. Many Updates & improvements in all units, all units have private entrances/porches, no shared systems or hallways. One water meter(landlord pays water/sewer) separate electric meters. Furnished rentals have leases into August 2025, unfurnished has lease until June 2026. Decade of rental history.

Details about Five Petals

$1,259,000.

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

New Antique Home Listing in Albemarle!

Greentree Farm

Year Built: 1900

On the market for the first time in nearly 50 years, this remarkable 130-acre property offers a rare opportunity to own a diverse and scenic piece of Central Virginia. Spanning 2 distinct parcels, the land features rolling pastures, hardwood forests, two ponds, & breathtaking views of Southwest Mountain—all anchored by a picturesque c. 1900 farmhouse. Perfectly suited for horses, cattle, hay, or even a vineyard, the property is an excellent candidate for conservation easement. Surrounded by protected farms and estates, it offers both privacy & long-term preservation potential. The character-rich farmhouse could serve as a primary residence, weekend retreat, or guesthouse—leaving open the option to build on one of several exceptional homesites with mountain views. Additional improvements include a 2nd home overlooking a pond, a small barn, an equipment shed, & gently rolling acreage ready for agricultural or recreational use. Located in a region rich with history and natural beauty, this special offering is priced $400,000 below the 2025 assessment—an incredible value for land of this caliber. Just 25 min to Charlottesville, 1 hr to Richmond, 2 hrs to D.C., and only moments to the conveniences of historic Gordonsville.

Details about Greentree Farm

$2,800,000.

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

Churchville Ave

Year Built: 1900

This charming and spacious home is looking for its next owner! Within walking distance to historic downtown Staunton AND Gypsy Hill Park, this property is super conveniently located. Walk to Shenanarts plays~which are right across the street, Blackfriars playhouse, the farmers market, Art in the Park, hear music from the park on your front porch, including a front row seat to the Independence Day fireworks! When you step inside, embrace the charm of yesteryear with the modern conveniences of today. The kitchen is nicely updated, central air conditioning, a full bath on each level, fresh paint, beautifully maintained heart pine floors, spacious bedrooms, multiple common areas which could be used as an office, sunroom or potentially a 4th bedroom and a Valor gas direct vent fireplace. The side yard is fenced so bring the pup (and the chickens)!!! Looking for outdoor spaces? We have them! Front, back, side...take your pick! Did I mention there is off and on street parking-perfect for entertaining! The views from the front porch are breathtaking, come see for yourself!

Details about Churchville Ave

$475,000.

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

Locust Ave

Year Built: 1900

JUST LISTED! Historic Craftsman in Downtown Charlottesville – A Visionary’s Dream! Located in the highly sought-after Martha Jefferson neighborhood of Downtown Charlottesville with alley access, this historic Craftsman-style home is waiting to be reimagined! Just moments from restaurants, live music, coffee shops, and all the charm of downtown, this property is an incredible opportunity for those looking to create something special. Step inside to find soaring 10’ ceilings (remove paneling with potential for even more height!), grand foyer, expansive room sizes, solid hardwood floors and vintage sliding doors that once led to a parlor—a true nod to its historic character. The home also boasts a metal roof, a welcoming front porch, and a yard that was once fully fenced (partially fenced now) for added privacy. With tons of off-street parking via alley access and space to build your own garage, the potential here is endless! This property needs a total remodel, and the seller has no knowledge of its condition—bring your vision and your offers! Location. Character. Unlimited Possibilities. Don’t miss your chance to transform this historic gem! Sold as is.

Details about Locust Ave

$695,000.

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

New Antique Home Listing in Charlottesville!

Altamont Cir

Year Built: 1908

Own a piece of history! Among the most prestigious homes on coveted Altamont Circle on large, landscaped lot, this fine brick residence welcomes visitors w/ an expansive front porch. Step into a grand foyer anchoring the home, leading to LR & DR, each with fireplace, as well as a 21st century lavish Owner’s Suite w/ generously sized BR, 2 WICs & custom bath with soaking tub, separate vanities, zero clearance shower & extra laundry stack. Upstairs find four sizeable BRs, one with its own fireplace, another with a walk-up attic, and another that serves perfectly as a home office and features views of the city. At the rear of the home a kitchen & sunroom open to a deck with covered portico for dining and overlooking the city. Charming, fenced gardens below feature a patio, stone wall & koi pond. The elevated lot shows off a western view of urban landscape, framed by distant mountains! Terrace level includes separate laundry, full bath, storage, and a bonus room with access to back yard. Bonus space ideal for a rec room or home gym. Off street parking for several cars. Easy access to downtown shops, restaurants & venues. Priced under assessment for expected kitchen updates and floor plan alterations at rear of home. OPEN SAT 5/3 12-2

Details about Altamont Cir

$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!

James River Rd

Year Built: 1914

HISTORIC SCOTTSVILLE GEM READY FOR RENEWAL! Just minutes from the James River, this 1914 Greek Revival-style home sits on over five acres, offering endless potential. Classic architectural details include a grand double-columned portico, high ceilings, wood flooring, and multiple fireplaces. The spacious kitchen is a blank slate, ready for customization, while original outbuildings—including a garden house with a working pump—add to the home’s historic charm. With 5 bedrooms and 3.5 bathrooms, this property is perfect for those looking to restore a timeless estate or create a unique bed & breakfast. Located in a serene setting, this property combines the charm of early 20th-century architecture with the tranquility of rural living, all while being conveniently close to local amenities in Albemarle County and Charlottesville. Expand into the large unfinished attic and basement for additional living space.

Details about James River Rd

$699,500.

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

Fernwood

Year Built: 1915

Fernwood--c.1915 brick Federalist manor home, built using lumber, stone, and brick sourced from the property and surrounding area. From an initial restoration by the current owners over 50 years ago, Fernwood has been lovingly and painstakingly renovated and enlarged, creating a one-of-a-kind property designed for comfortable living and gracious entertaining. 5 bedrooms, country kitchen with antique beams, stunning great room with 14ft ceilings and stone FP, English bsmt with exposed stone walls, original oak floors, huge patio with outdoor FP, extensive brick hardscaping, pool, formal gardens, 4 car garage, guest cottage, the list goes on and on. Fernwood has hosted numerous weddings, parties, and family events. 22 acres with mature forest, spring-fed stream, and walking trails Nestled at the foot of a small mountain in a valley of fine homes and estates just 10 minutes south of Charlottesville and UVA, and in close proximity to diverse recreation opportunities and vineyards, this is a rare opportunity to assume the stewardship of a remarkable southern Albemarle estate property.

Details about Fernwood

$2,478,000.

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

Buck Mountain Rd

Year Built: 1915

This charming Earlysville Farmhouse rests on two pastural acres with a sprinkling of hardwoods for summer shade. Lovingly maintained, restored and modernized, this four bed, two bath home checks every box, offering tremendous flexibility as one bedroom and one full bath are located on the ground floor -as is the generously sized living room, dining room and remodeled kitchen with newer countertops and sink. Outside you'll find park-like yard space, and a barn/garage but you'll likely spend your evenings on the deep western facing front porch, the perfect spot to enjoy stunning sunset mountain views over the neighboring farmland.

Details about Buck Mountain Rd

$465,000.

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

Valley St

Year Built: 1916

OPEN HOUSE- SUNDAY, 3/30, NOON-2:00 Amazing opportunity to own a piece of Scottsville history. This stunning residence has unlimited possibilities, including a grand downtown home. Showcasing original period architectural details, original hardwood floors, and double porches that overlook the downtown area. Finish the spacious walk-up attic into a private owners suite. Beautiful mature landscaping. The unfinished, original carriage house provides potential for expansion and/or a Main Street office space. Enjoy being able to walk to everything Scottsville has to offer, local brewery, bakery, coffee shop, restaurants, library, Van Clief nature area/walking trails, and the James River public access.

Details about Valley St

$699,000.

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

Rugby Rd

Year Built: 1917

Stunning C. 1917 Rugby Road compound available for the first time in nearly 50 years. The main house features a deep full front porch, inviting foyer, living room, library, apartment/office/main level primary option, generous dining room, expanded renovated kitchen. The second level features a four-room ensuite primary suite plus additional bedrooms and bath. The third floor offers a large open room, bedroom and bath. The covered back porch steps down to the lush expansive landscaping with stone terrace, stone steps to the cottage and writers/art studio. The renovated cottage features a spacious living room with fireplace, kitchen, 2 bedrooms and bath. The lower level offers a large open space, laundry and half bath. The studio boasts a vaulted ceiling, skylight, oversized window, sleeping loft. There's also a detached garage/workshop. Two separate parcels total 1.25 acres offering privacy and room to enjoy the beautiful mature park like landscape. Fresh paint inside and out. Staging in process. Professional photos will be posted on May 1st.

Details about Rugby Rd

$2,500,000.

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. Gorgeous heart pine flooring on the main level has recently been restored to it's original natural finish. 5 BRs and 3.5 baths, including a 1st floor primary suite/bath, & an elevator that services the main level and partially finished basement that has the potential for 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

$1,175,000.

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

10 1/2 St

Year Built: 1920

This fantastic two-story farmhouse is ideally situated just minutes from UVA in downtown Charlottesville, offering great value. The home features a living room, a remodeled eat-in kitchen. In 2006, a new addition was added, featuring a first-floor bedroom, half bath, and laundry room. Upstairs, you'll find two additional bedrooms that share a full bath. Enjoy the charm of the front porch, off-street parking, and a very private rear backyard complete with a large storage shed. This home is in good condition and ready for its new owner!

Details about 10 1/2 St

$449,900.

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

New Antique Home Listing in Charlottesville!

Valley Rd

Year Built: 1920

Wonderful opportunity to live near the Grounds of UVA. This charming cottage affords one level living and has built-in bookshelves and a pitched ceiling in the living room. The home is currently rented through May of 2026. Walk to UVA and UVA hospital.

Details about Valley Rd

$450,000.

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

Lee Hwy

Year Built: 1920

Nicely restored farmhouse on 4+ acres in 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. Renovated kitchen, updated appliances. New furnace 2024. Terrace level features Bedroom, Bath/Laundry, sunroom, large den/rec room. Property is zoned Agriculture and is located in the Commercial District. Previous commercial uses include corporate offices, healing center, distribution center and most recently a Fine Art Gallery. Great opportunity to live and work on site. DSL available. Shown by appointment only. Call Agent for showings and directions. Tenant Occupied. Owner/Licensee.

Details about Lee Hwy

$680,000.

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

Belmont Ave

Year Built: 1920

Set squarely in the center of a unique three-lot parcel in Belmont, one of the city's most coveted walkable downtown neighborhoods, this timeless 1920s farmhouse is rich in historic charm. A welcoming front porch and an expansive 12 x 24 screened-in back porch provide ideal spaces to relax and take in the beauty of the spacious, landscaped yard, which offers plenty of room for gardening and outdoor enjoyment. Inside, the classic layout features three bedrooms—one on the main level and two upstairs—along with two full baths, a cozy eat-in kitchen, a formal dining room with a striking Palladian window, an inviting living room, and a dedicated laundry room. Just a short stroll from the lively downtown mall, this home places you in the heart of the city’s best amenities—catch live music at the outdoor pavilion, see a performance at Live Arts, or dine at one of the many beloved local restaurants. The IX Art Park, local farmers markets, and ACAC fitness center are also nearby. On the market for the first time in 35 years, this is a rare opportunity to own a piece of history in an unbeatable location! RA Zoning allows for up to 3 structures to be built offering great investment opportunities for income producing potential! A rare find.

Details about Belmont Ave

$798,000.

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

Monticello Ave

Year Built: 1920

This remarkable and spacious Belmont gem finds the perfect balance of historic Charlottesville charm and modern living and is not to be missed. Fronted by a classic wraparound porch, the opened and expanded entry level boasts numerous windows, high ceilings & a variety of sitting and mixing spaces which flow easily into the central kitchen. Close at hand is the breakfast nook, cozy under skylights and vaulted ceiling as well as the walk in pantry, sunroom, powder room and rear patio area. The second floor offers a large, many windowed bedroom, full hall bath with laundry and a second ensuite bedroom bath combination. The third floor features two additional bedrooms, each with dedicated modern baths, large walk in closets, additional storage and commanding southwestern views of the city and mountains beyond. Among the numerous improvements and updates are solar panels mini-splits & heat pump, modern windows, plumbing, electrical & lighting, 6 year old roof and freshly painted siding while exposed beams, high ceilings and original doors & moldings harken to times past.

Details about Monticello Ave

$999,000.

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

Storybook Cottage

Year Built: 1925

Truly, this is a storybook home on one of the city's most coveted, quiet streets. Beautifully renovated in recent years, this c.1925 stone gem offers period charms and modern luxuries throughout. From exposed, interior stone walls, to marble bathrooms, endless built-ins and a chef's kitchen drenched with natural light, 1840 Fendall Avenue delights at every turn. The home is set well off Fendall Avenue and the 0.3 acre parcel is dead level. There is an expansive stone patio that flanks the entire rear of the home, with plenty of seating and dining areas, as well as a soapstone outdoor fireplace. This neighborhood is tucked away off of Rugby Road and with wide streets and sidewalks, is ideal for walking to UVA, JPJ and Barracks Road amenities.

Details about Storybook Cottage

$1,495,000.

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

Castalia St

Year Built: 1925

A charming Belmont home on a quiet street, walking distance to the neighborhood restaurants and the downtown mall. The house retains much of its original character and, while livable, is a perfect candidate for restoration. Original hardwood floors and architectural detail. Useful side porch for storage. The exterior envelope is in good condition. While just off Monticello Avenue, the home is surprisingly protected from road noise.

Details about Castalia St

$405,000.

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

High St

Year Built: 1925

Unique opportunity to own a true piece of Charlottesville's history. This 3-bedroom condominium offers incredible charm with the original hardwood floors, arched doorways and built-in shelves. This home is located on the first floor and is a corner unit which enhances the natural light. The location is ideal! Just three blocks from the Historic Downtown Mall, Live Arts, the Paramount and a multitude of restaurants and shops. The large back deck is a perfect place to relax. The HOA dues include Water/Sewer, Heat, Ext. Maintenance and Landscaping. There is also a community laundry facility on the same level. This Condominium can also be used as Commercial Space (perfect office).

Details about High St

$425,000.

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

Charming Fifeville Cottage

Year Built: 1925

Charming Fifeville Cottage ---A Rare Opportunity--- Don’t miss this rare chance to own a beautifully renovated home on one of Fifeville’s most delightful streets. Step onto the newly rebuilt front porch and into a light-filled, open floor plan that blends classic charm with modern comfort. Thoughtfully reimagined in 2009 from the studs out, this cottage was redesigned to offer generously sized rooms and exceptional livability. Enjoy a private backyard retreat, off-street parking, and a location that offers walkability with room to breathe. Whether your clients are seeking character, convenience, or space to unwind, this home is a must-see.

Details about Charming Fifeville Cottage

$515,000.

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

5th Street Farm House

Year Built: 1925

Unique Farm house styled home in prime location just ~1 mile from the University of Virginia Hospital, Downtown Mall, or Wegman's shopping center! Featuring original hardwood floors and an expansive floorpan, this home has everything you need to make your own. This home was thoughtfully renovated in 2005 and all major systems were replaced and updated. There is a bright and open living room adjacent to the kitchen and a bedroom and full bathroom on the first floor, along with three additional bedrooms upstairs. The bedroom on the main level could also be utilized as a home office/study or as a main floor primary with attached full bathroom.

Details about 5th Street Farm House

$550,000.

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

High St

Year Built: 1925

Charming Boutique Building in coveted downtown location...Unique, light-filled condo located just one block off Court Square...Opportunity to have an office and/or residence in this immaculate property...Bright, large rooms with a tremendous amount of flexibility of how to use the space...Front and rear entrances with cute deck in the back...

Details about High St

$565,000.

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

7th St

Year Built: 1925

**Rare Find in Historic Charlottesville! Step into timeless elegance with this meticulously maintained 1925 gem, perfectly positioned between Downtown Mall’s vibrant energy and UVA’s academic prestige. Walk just minutes to boutique shops, acclaimed restaurants, and the Amtrak station—urban convenience meets classic charm. Inside, discover 3 bedrooms and 2.5 baths complemented by original hardwood floors, blending historic character with modern comfort. The fully fenced backyard offers a private oasis, while mature cherry trees frame the inviting front yard. Zoned for expansion, this property is a goldmine for investors or visionaries seeking to build additional units or create a custom compound. Whether you crave a turnkey home or a strategic investment with limitless potential, this rare offering delivers both. Seize the chance to own a piece of Charlottesville’s legacy while shaping its future—act fast before this unparalleled opportunity slips away!

Details about 7th St

$610,000.

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

Chestnut St

Year Built: 1925

Stunning Belmont farmhouse w/ comprehensive renovation. Award winning architecture & construction team has transformed & expanded this character-rich historic home into a light & inviting modern dwelling. All new electrical, plumbing, HVAC & more. Restored wood floors & moldings throughout, w/ elegant modern detailing in the addition. The full front porch leads into a generous foyer which opens to the living & dining rooms. The dining room opens to the amazing new family room & kitchen featuring cascading quartz countertops, abundant cabinetry, & expansive island. The family room & kitchen bring the outdoors in, w/ a picture window & generous sliding doors to the oversized deck w/ cable railing. The main level also offers a mudroom, powder room, & laundry room. The second level boasts four bedrooms, two full baths, including the new ensuite primary bedroom w/ dressing room, abundant closet space, light-filled bathroom, & mountain views. Off street parking. Clean, dry storage space is found in the freshly encapsulated conditioned crawl space. Inviting fenced backyard with garden space & lawn & landscaping to enjoy the outdoors. Friendly neighborhood, a short walk to the amazing restaurants & shops in Belmont & the Downtown Mall.

Details about Chestnut St

$969,900.

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

Court Sq

Year Built: 1926

Rare opportunity available in the historical Court Square Condos building to own an 8th Floor, 2 bedroom/2 full bath Condo with Amazing Panaramic Views of the Central City and Blue Ridge Mountains. This was originally 2 separate suites at the old Monticello Hotel (801 & 807) converted to one condo on the Corner End of Building with 3 exterior walls to Capture the Views! See Floorplan in Photos. Washer/Dryer in each floor common area. Located across from the beautiful Courthouse grounds and 2 blocks from the Downtown Mall, with restaurants, shopping, galleries, theatres, etc. The monthly Condo fees cover water, sewer, electric, trash, lobby attendant and internet. Come and put your personal finishing touches on this piece of history and make it your own! Priced to sell at the current APPRAISAL VALUE! SOLD "As Is, Where Is!" See 8th Floor Planplan in Docs!

Details about Court Sq

$499,000.

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

Parkway St

Year Built: 1929

Downtown Charlottesville with commercial potential. A story-book home with charm and character rumored to be one of the Sears Roebuck houses. From the moment you walk into the entry hall, you will fall in love. The owners added a 2-story addition in 1999 to make this 1920's classic perfect for today. Thoughtful details, spacious rooms, a delightful rear yard with a garage. Live upstairs and have your public offices on the main level! Zoning allows many possibilites.

Details about Parkway St

$1,100,000.

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

Locust Ave

Year Built: 1929

Totally charming, 1929, classic brick home located in north downtown...Tastefully renovated and updated without losing the original character...9' ceilings, built-in bookcases, beautiful woodwork, trim and crown moldings...Sun filled spaces on three levels...Phenomenal, professionally landscaped yard with mature plantings offers room for relaxation, play, and entertaining...private, off-street parking...Walkable community with wide streets and sidewalks...Quick access to major roadways, UVa and Downtown ...Recent upgrades include: new roof 2022, replacement windows, renovated bathrooms, exterior painted 2022, and new Plantation shutters...

Details about Locust Ave

$850,000.

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