Vintage homes for sale & real estate in Madison County, VA

11 homes

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ABOUT THIS HOME
Vintage Home for sale in Madison County, VA:
A rare piece of history bordering Shenandoah National Park on one side and the Robinson River on the other, “Old Rag Homeplace” is a stunning 36.90+ acre retreat offered for the first time in over 50 years. The charming home boasts a main cabin built in 1865 from hand-hewn chestnut logs and a native stone fireplace. The house includes an open kitchen-dining area, 3 bedrooms, a loft, and 2 baths. Endless outdoor recreation awaits right at your doorstep. Located just minutes from the White Oak Canyon and Old Rag Mountain trailheads, you can easily access spectacular waterfalls and panoramic summit views. Spend your days fly fishing on the renowned Robinson, Hughes and Rose trou

$995,000

3 beds2 baths1,612 sq ft

2042 Weakley Hollow Rd, Syria, VA 22743

Fly fishing streams • Access to waterfalls • Historic main cabin

ABOUT THIS HOME
Vintage Home for sale in Madison County, VA:
Spacious 4-bedroom, 2-bath home on 6.35 private acres in Rochelle. This 2,409 sq ft property offers a functional layout with large living areas and plenty of natural light. This property provides a foundation for customization. Features include a screened‑in porch, detached garage, and a mix of open yard space and mature trees. Quiet rural setting with room for gardening, animals, or outdoor recreation. Convenient location just minutes from Route 29 with easy access to Madison, Culpeper, and Charlottesville. Roof is 20 years old, windows have been updated vinyl siding, hot water heater 3 months old, gas propane tank is owned, the detached garage does have electricity.

$299,999

4 beds2 baths2,409 sq ft

92 Buggy, Rochelle, VA 22738

Private acres • Screened in porch • Quiet rural setting

(540) 812-3233

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Madison County, VA:
Recently renovated with the intention of being a forever home, this charming 1940s farmhouse was lovingly transformed while preserving the character, warmth, and timeless appeal that make it so special. Each project was completed with quality, durability, and longevity in mind. With 1,144 square feet, the home offers just enough space to get away to the extraordinarily scenic countryside of Madison County, Virginia…without all the maintenance. It is ideal as a full-time residence, weekend getaway, or second home near Shenandoah National Park. Sited for privacy on a lovely knoll, the house sits quietly among trees on this 4.2-acre lot. It is nearly invisible from the state-maintained

$475,000

2 beds1 bath1,144 sq ft

2303 W Hoover Rd, Haywood, VA 22722

4.2 acre lot • Turnkey farmhouse • 4.2 acre lot

(703) 790-1850

ABOUT THIS HOME
Vintage Home for sale in Madison County, VA:
Come see this 3 bedroom 1 bath home on 3 recently surveyed acres in beautiful Aroda in Madison County. It features hardwood floors, double pane windows, and a heat pump for efficient heating and cooling. The bathroom has a tub as well as a separate fiberglass shower. Washer and dryer hookups are conveniently located on the main floor and also in the basement. A turned metal roof along with the freshly painted interior and exterior make this a must-see home. The home has an enclosed front porch, a partial basement and a barn/garage with electricity. The home is located on a private gravel road and has a shared well. Owner financing is available with $12,000 down and $2260 per month for a 30

$275,000

3 beds1 bath1,550 sq ft

219 Skyview Ln, Aroda, VA 22709

Heat pump • Partial basement • Double pane windows

(888) 838-9044

OPEN SAT, 2PM TO 4PM

ABOUT THIS HOME
Vintage Home for sale in Madison County, VA:
This newly renovated 3-bed, 2-bath home in Madison County makes it easy to picture your life here, waking up to panoramic mountain views, sipping coffee on your deck, and coming back to a space that feels warm and effortless. Inside, the granite countertops and luxury vinyl plank flooring throughout add a clean, modern feel that’s both beautiful and practical for everyday living. The open layout provides you with ample space to breathe, relax, and make the home your own from the very start. With a new roof, HVAC, appliances, insulation, deck, sidewalk, doors, and flooring. This beautiful home features spacious rooms and incredible views right outside your door. This is the kind of pla

$345,000

3 beds2 baths1,502 sq ft

399 Shelby Rd, Madison, VA 22727

New hvac • Open layout • Granite countertops

(703) 378-8810

Property at 481 Race Ground Rd, Rochelle, VA 22738, 4 beds, 5 baths

$4,750,000

4 beds5 baths5,636 sq ft

481 Race Ground Rd, Rochelle, VA 22738

Property at 575 Arcadian Way, Orange, VA 22960, 5 beds, 4.5 baths

$5,575,000

5 beds4.5 baths13,455 sq ft

575 Arcadian Way, Orange, VA 22960

Property at 1830 Thrift Rd, Madison, VA 22727, 3 beds, 2 baths

$5,850,000

3 beds2 baths3,023 sq ft

1830 Thrift Rd, Madison, VA 22727

(434) 296-1234

Property at TBD Mount Pisgah Church Dr, Orange, VA 22960, 3 beds, 1 bath

$129,000

3 beds1 bath— sq ft

TBD Mount Pisgah Church Dr, Orange, VA 22960

(540) 825-1613

$1,500,000

4 beds2 baths1,500 sq ft

4408 Seminole Trl, Brightwood, VA 22715

(301) 445-1395

Property at 1165 S F T Valley Rd, Madison, VA 22727

$135,000

Land2.00 acres (lot)

1165 S F T Valley Rd, Madison, VA 22727

(540) 371-7653

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NEW 21 HRS AGOFLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Madison County, VA:
Rare opportunity to own a beautifully renovated historic Main Street property in the heart of Luray! Dating to circa 1800, Briar Laine House combines the character and presence of a historic home with extensive updates and an exceptionally versatile floor plan offering 7 total bedrooms, 4.5 full bathrooms, and two separate living spaces with private entrances. The main residence features 5 bedrooms and 3 full baths, while the adjoining second living space offers 2 bedrooms and 1.5 baths—providing tremendous flexibility for use as a substantial single residence, multi-generational living, an owner-occupant arrangement, or potential income-producing property. Each living space is design

$624,800

7 beds4.5 baths3,413 sq ft

146 E Main St, Luray, VA 22835

Full kitchen • Private entrances • Extensive updates

(540) 743-4545

OPEN SAT, 11AM TO 12PMVIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Madison County, VA:
There’s simply not another property quite like the Milton House. Set in downtown Stanley, this distinctive home offers more than 3,100 square feet in the main residence, plus a separate two-story cottage that adds even more flexibility to the property. Inside the main home, four second-level bedrooms all have direct access to a full bath, while the main level provides plenty of room to gather with a spacious kitchen, dining room, multiple living areas, and a sunroom leading outdoors. A large deck, hot tub, and fire pit area create even more space to enjoy the property beyond the walls of the home. The cottage features two updated suites and has been part of the property’s succes

$560,000

4 beds4 baths3,173 sq ft

113 W Main St, Stanley, VA 22851

Large deck • Hot tub • Spacious kitchen

(540) 820-5183

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Madison County, VA:
Here's a classic home with all of its period charm preserved. Handsome original features include board siding, tall windows with wavy glass, a broad front porch with turned railings and columns, and an embossed tin roof. Quality updates, including a fabulous kitchen, blend perfectly with the vintage vibe of large rooms with tall ceilings, original wood floors, pocket doors, and crown moulding throughout. The walk-up attic would be wonderful finished space. The pleasures of a tranquil backyard with a private patio and ample offstreet parking complete this lovely residence. Banks, post office, restaurants, pharmacy, churches, shops, the arts center, a pocket park are literally steps away, wit

$565,000

3 beds3 baths2,770 sq ft

189 Main St W, Orange, VA 22960

Wainscoting • Tall windows • Crown moulding

ABOUT THIS HOME
Vintage Home for sale in Madison County, VA:
Charming home located in scenic Rappahannock County with local breweries and wineries, restaurants including the The Inn at Little Washington. A short drive to Shenandoah National Park. Numerous updates include updated kitchen with new cabinets and countertops, stainless steel appliances including new range and dishwasher, freshly painted interior and new carpet in bedrooms. New roof with dimensional shingles. Bath with tiled shower/stub. Utility room features washer and dryer, laundry sink, and toilet. Detached outbuilding which is perfect for the hobbyist, additional storage area, etc. Additional storage sheds convey.

$419,000

3 beds1.5 baths1,196 sq ft

531 Richmond Rd, Castleton, VA 22716

0.81 acre lot • Built 1940 • Listed 5 days

(540) 349-1400

$299,888

3 beds1 bath1,629 sq ft

354 Berry St, Orange, VA 22960

Built 1958 • Listed 5 days

(571) 386-1075

ABOUT THIS HOME
Vintage Home for sale in Madison County, VA:
Location, character, convenience, and a home that has been well cared for! Welcome to 255 Montevista Ave, a charming and well-maintained one-level ranch nestled in the established Johnson Village neighborhood in the heart of Orange. This inviting 3-bedroom home offers the ease of single-level living along with the character buyers appreciate, including beautiful original hardwood floors and a bright, welcoming living area. The updated kitchen is a true highlight, featuring granite countertops, custom cabinetry, stainless steel appliances, and a movable butcher-block island that provides excellent workspace and storage. A convenient rear mudroom adds practical everyday living space and inclu

$274,900

3 beds1 bath1,018 sq ft

255 Montevista Ave, Orange, VA 22960

Custom cabinetry • Updated kitchen • Granite countertops

(703) 539-7062

Property at 10226 Glebe Rd, Orange, VA 22960, 3 beds, 2 baths

$395,000

3 beds2 baths2,574 sq ft

10226 Glebe Rd, Orange, VA 22960

(540) 948-6655

Property at 467 Vista View Rd, Stanley, VA 22851, 4 beds, 3 baths

$645,000

4 beds3 baths2,661 sq ft

467 Vista View Rd, Stanley, VA 22851

Property at 18235 Lahore Rd, Orange, VA 22960, 2 beds, 1 bath

$199,900

2 beds1 bath832 sq ft

18235 Lahore Rd, Orange, VA 22960

(888) 838-9044

Property at 9196 Sperryville Pike, Culpeper, VA 22701, 3 beds, 1 bath

$379,900

3 beds1 bath1,000 sq ft

9196 Sperryville Pike, Culpeper, VA 22701

(540) 825-1800

Property at 11 Bristol Ave, Luray, VA 22835, 4 beds, 2 baths

$309,990

4 beds2 baths1,700 sq ft

11 Bristol Ave, Luray, VA 22835

(540) 341-1000

Property at 9083 Caynor Pl, Culpeper, VA 22701, 3 beds, 2 baths

$550,000

3 beds2 baths2,095 sq ft

9083 Caynor Pl, Culpeper, VA 22701

(703) 754-1770

Property at 146 & 178 Main St, Stanardsville, VA 22973, 8 beds, 8.5 baths

$2,200,000

8 beds8.5 baths8,396 sq ft

146 & 178 Main St, Stanardsville, VA 22973

Property at 19424 River Rd, Rapidan, VA 22733, 3 beds, 3 baths

$2,700,000

3 beds3 baths5,464 sq ft

19424 River Rd, Rapidan, VA 22733

Property at 114 Celt Rd, Stanardsville, VA 22973, 3 beds, 2 baths

$184,900

3 beds2 baths1,260 sq ft

114 Celt Rd, Stanardsville, VA 22973

Property at 2646 Frays Mill Rd, Charlottesville, VA 22968, 3 beds, 3 baths

$1,795,000

3 beds3 baths2,776 sq ft

2646 Frays Mill Rd, Charlottesville, VA 22968

Property at 9406 Obannons Mill Rd, Boston, VA 22713, 3 beds, 2 baths

$750,000

3 beds2 baths2,054 sq ft

9406 Obannons Mill Rd, Boston, VA 22713

(540) 675-1200

Property at 236 Caroline St, Orange, VA 22960, 7 beds, 6 baths

$999,000

7 beds6 baths3,765 sq ft

236 Caroline St, Orange, VA 22960

(540) 388-2541

Property at 189 Newton St, Orange, VA 22960, 4 beds, 3 baths

$365,000

4 beds3 baths2,030 sq ft

189 Newton St, Orange, VA 22960

Property at 9034 Spotswood Trl, Stanardsville, VA 22973, 2 beds, 1 bath

$329,000

2 beds1 bath1,262 sq ft

9034 Spotswood Trl, Stanardsville, VA 22973

Vintage Homes for Sale in Madison County

There are currently 11 vintage homes for sale in Madison County at a median listing price of $480K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Madison County stay on the market for 52 days and receive 1 offers. This map is refreshed with the newest listings in Madison County every 15 minutes.

In the past month, 14 homes have been sold in Madison County. Find your dream home in Madison County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Madison County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Madison County. If you're looking to sell your home in the Madison County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Madison County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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