Vintage homes for sale & real estate in Jefferson County, IN

43 homes

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ABOUT THIS HOME
Vintage Home for sale in Jefferson County, IN:
Location is key, and this property sits between two of the "Best Small Midwest Towns in America, " according to USA Today. Conveniently located between Madison and Vevay, this versatile 10 acre tract offers a mix of residential, recreational, and small business potential. The parcel features about 1,100 feet of State Road 56 frontage and roughly 100 feet on E Splinter Ridge Road. A paved road that once served as the main highway now winds privately through the property, creating a unique paved drive for walking, biking, or vehicle access. Originally built in 1900, the historic home reflects craftsmanship from its era, still visible in portions of the rafters and framing. The resid

$300,000

4 beds2 baths2,708 sq ft

8273 E State Road 56, Madison, IN 47250

New furnace • 10 acre tract • New roof

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, IN:
Open to interpretation!! How shall this property be finished? The preservation organization succeeded in stabilizing and beatifying its original footprint! This cottage needs to be made cozy by an individual ready to give it its layout and design. There are preservation covenants, held by Indiana Landmarks, with this property.

$129,000

0 beds— baths903 sq ft

707 Walnut St, Madison, IN 47250

2,482 sq ft lot • Built 1880 • Listed 10 days

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, IN:
Charming 2-bedroom, 1-bath cottage in the heart of historic downtown Madison! This beautifully updated home blends classic character with modern style and comfort. Enjoy relaxing on the inviting front or back covered porches surrounded by lovely landscaping. The backyard features a yard barn, off-street parking, and plenty of space to unwind. Just a short walk to shopping, dining, and the scenic Ohio River — the perfect downtown retreat!

$209,900

2 beds1 bath1,020 sq ft

906 W Main St, Madison, IN 47250

Covered porches • Backyard features • Historic downtown

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, IN:
Warm and Cozy feeling, just like Grandma's Home!! Live in Madison and ENJOY All the Fun Festivities Within Walking Distance! Sitting in Madison's Historical District, just 2 Blocks from the Ohio River Bridge Sits this Lovely SOLID 2 Story Brick Home! Hardwood Floors w Rugs, 3 Bedrooms, 2 1/2 Baths, (2 full baths newly remodeled!), Laundry is Upstairs, Electric Fireplace Insert with Heat in Liv Rm & Extra LARGE Rooms! Relax on the Front Porch or BBQ Out Side Patio! CIRCLE DRIVEWAY in Back Yard! Outside entrance to basement Workshop Area and Playrooms! Recent upgrades: Furnace and Central Air, Thermopane Windows and Roof! At list price could be purchased Furnished with the Antiques for

$299,000

3 beds2.5 baths4,740 sq ft

910 E 2nd St, Madison, IN 47250

Recent upgrades • Historical district • Circle driveway

ABOUT THIS HOME
Vintage Home for sale in Jefferson County, IN:
Discover this Italianate two-part in a commercial block, constructed circa 1870, brimming with potential for various business ventures or investment opportunities! * * Property Highlights * * Spacious first floor - Enjoy approximately 3140 sq ft of versatile space, perfect for retail or office use. Flexible Second Floor - Currently utilized for storage, this level can easily be transformed to suit your needs, whether it be additional office space or even more retail opportunities. Third Floor Comfort - A welcoming apartment provides both convenience and potential rental income, making this property a smart investment. Property runs from Main Street to the back alley. Don't miss out on a

$369,900

1 bed1 bath6,337 sq ft

316 W Main St, Madison, IN 47250

Second floor • Third floor • First floor

Property at 212 St Michaels Ave, Madison, IN 47250, 3 beds, 1.5 baths

$289,900

3 beds1.5 baths1,152 sq ft

212 St Michaels Ave, Madison, IN 47250

Property at 410 Baltimore St, Madison, IN 47250, 3 beds, 3.5 baths

$329,999

3 beds3.5 baths2,154 sq ft

410 Baltimore St, Madison, IN 47250

Property at 626 W Third St, Madison, IN 47250, 2 beds, 1.5 baths

$189,900

2 beds1.5 baths1,816 sq ft

626 W Third St, Madison, IN 47250

Property at 2705 Lanier Dr, Madison, IN 47250, 2 beds, 1 bath

$189,000

2 beds1 bath1,024 sq ft

2705 Lanier Dr, Madison, IN 47250

Property at 5756 N Sr 62, Madison, IN 47250, 4 beds, 2 baths

$399,900

4 beds2 baths1,584 sq ft

5756 N Sr 62, Madison, IN 47250

Property at 410 Mill St, Madison, IN 47250, 4 beds, 2 baths

$399,000

4 beds2 baths2,984 sq ft

410 Mill St, Madison, IN 47250

Property at 14266 W Mulberry St, Deputy, IN 47230, 1 bath

$215,000

0 beds1 bath4,419 sq ft

14266 W Mulberry St, Deputy, IN 47230

Property at 1122 W Second St, Madison, IN 47250, 2 beds, 1.5 baths

$295,000

2 beds1.5 baths1,021 sq ft

1122 W Second St, Madison, IN 47250

Property at 14209 W Main St, Deputy, IN 47230, 5 beds, 1.5 baths

$139,900

5 beds1.5 baths1,700 sq ft

14209 W Main St, Deputy, IN 47230

Property at 1127 S Thompson Rd, Lexington, IN 47138, 3 beds, 1.5 baths

$192,500

3 beds1.5 baths1,917 sq ft

1127 S Thompson Rd, Lexington, IN 47138

Property at 716 W 2nd St, Madison, IN 47250, 2 beds, 1.5 baths

$339,900

2 beds1.5 baths1,584 sq ft

716 W 2nd St, Madison, IN 47250

Property at 215 W Main St, Madison, IN 47250, 1 bed, 1.5 baths

$299,000

1 bed1.5 baths2,038 sq ft

215 W Main St, Madison, IN 47250

Property at 204 W Third St, Madison, IN 47250, 3 beds, 2.5 baths

$639,900

3 beds2.5 baths2,608 sq ft

204 W Third St, Madison, IN 47250

Property at 9408 N State Road 7, Dupont, IN 47231, 4 beds, 1 bath

$469,000

4 beds1 bath2,126 sq ft

9408 N State Road 7, Dupont, IN 47231

EXP Realty LLC

Property at 3990 Richard Cart Rd, Deputy, IN 47230, 2 beds, 1 bath

$39,900

2 beds1 bath966 sq ft

3990 Richard Cart Rd, Deputy, IN 47230

Property at 957 W Main St, Madison, IN 47250, 2 beds, 2 baths

$276,900

2 beds2 baths1,624 sq ft

957 W Main St, Madison, IN 47250

Property at 2945 N Greenbrier Rd, Madison, IN 47250, 1 bed, 1 bath

$500,000

1 bed1 bath1,233 sq ft

2945 N Greenbrier Rd, Madison, IN 47250

Trueblood Real Estate

Property at 1207 W Main St, Madison, IN 47250, 2 beds, 1 bath

$224,900

2 beds1 bath1,248 sq ft

1207 W Main St, Madison, IN 47250

Property at 506 Jefferson St, Madison, IN 47250, 3 beds, 2 baths

$350,000

3 beds2 baths2,124 sq ft

506 Jefferson St, Madison, IN 47250

Property at 130 Jessup Ln, Madison, IN 47250, 3 beds, 1.5 baths

$229,900

3 beds1.5 baths1,266 sq ft

130 Jessup Ln, Madison, IN 47250

Property at 958 Walnut St, Madison, IN 47250, 3 beds, 2 baths

$199,900

3 beds2 baths1,280 sq ft

958 Walnut St, Madison, IN 47250

Property at 1912 Locust St, Madison, IN 47250, 3 beds, 1.5 baths

$209,900

3 beds1.5 baths1,216 sq ft

1912 Locust St, Madison, IN 47250

Property at 3490 N Rykers Ridge Rd, Madison, IN 47250, 3 beds, 1 bath

$199,900

3 beds1 bath1,148 sq ft

3490 N Rykers Ridge Rd, Madison, IN 47250

Property at 128 West St, Madison, IN 47250, 3 beds, 2 baths

$414,900

3 beds2 baths1,127 sq ft

128 West St, Madison, IN 47250

Property at 708 E Main St, Madison, IN 47250, 5 beds, 5.5 baths

$799,900

5 beds5.5 baths4,404 sq ft

708 E Main St, Madison, IN 47250

Property at 313 E First St, Madison, IN 47250, 1 bed, 2.5 baths

$750,000

1 bed2.5 baths4,030 sq ft

313 E First St, Madison, IN 47250

Property at 2921 Ohio Ave, Madison, IN 47250, 3 beds, 1 bath

$194,900

3 beds1 bath1,008 sq ft

2921 Ohio Ave, Madison, IN 47250

Property at 1127 Walnut St, Madison, IN 47250, 2 beds, 1 bath

$295,000

2 beds1 bath1,623 sq ft

1127 Walnut St, Madison, IN 47250

Property at 413 Mill St, Madison, IN 47250, 4 beds, 1.5 baths

$329,900

4 beds1.5 baths2,180 sq ft

413 Mill St, Madison, IN 47250

Property at 416 E Second St, Madison, IN 47250, 5 beds, 4 baths

$675,000

5 beds4 baths4,296 sq ft

416 E Second St, Madison, IN 47250

Property at 332 W Lagrange Rd, Hanover, IN 47243, 4 beds, 2.5 baths

$199,900

4 beds2.5 baths1,626 sq ft

332 W Lagrange Rd, Hanover, IN 47243

Property at 109 Central Ave, Madison, IN 47250, 2 beds, 1 bath

$425,000

2 beds1 bath1,082 sq ft

109 Central Ave, Madison, IN 47250

Property at 111 N Main Cross St, Hanover, IN 47243, 4 beds, 2 baths

$254,999

4 beds2 baths2,182 sq ft

111 N Main Cross St, Hanover, IN 47243

Property at 4146 W State Road 56, Hanover, IN 47243, 3 beds, 2 baths

$498,500

3 beds2 baths2,088 sq ft

4146 W State Road 56, Hanover, IN 47243

Property at 121 Presbyterian Ave, Hanover, IN 47243, 4 beds, 4 baths

$449,900

4 beds4 baths5,790 sq ft

121 Presbyterian Ave, Hanover, IN 47243

Property at 5934 W Woodspirit Way, Dupont, IN 47231, 2 beds, 1 bath

$589,000

2 beds1 bath2,808 sq ft

5934 W Woodspirit Way, Dupont, IN 47231

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Based on information submitted to the MLS GRID as of Sun Nov 30 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Vintage Homes for Sale in Jefferson County

There are currently 43 vintage homes for sale in Jefferson County at a median listing price of $275K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Jefferson County stay on the market for 63 days. This map is refreshed with the newest listings in Jefferson County every 15 minutes.

In the past month, 29 homes have been sold in Jefferson County. In addition to houses in Jefferson County, there was also 1 condo, 1 townhouse, and 1 multi-family unit for sale in Jefferson County last month. Find your dream home in Jefferson 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 Jefferson County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Jefferson County. If you're looking to sell your home in the Jefferson County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Jefferson 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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