Real Estate Investment Properties for Sale in Madison, VA

Looking for investment property in Madison, VA with high ROI ?

Explore a variety of short-term homes & houses in Madison, VA. Invest wisely with VRBO & Madison, VA Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Madison, VA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
984 OAK PARK MADISON, VA Welcome to this beautifully renovated home nestled on 1.6 private acres in Madison, VA. Mo...	3 beds \| 2 baths \| 1,942 sq.ft.	$420,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 4.02% Airbnb Rental Income: $1115 Traditional Rental Income: $2194 Airbnb ROI: 0.33% Traditional ROI: 4.02%
319 N Main St MADISON, VA Well maintained historical home in the heart of Madison. Home featured in the historic ho...	3 beds \| 1 baths \| 2,744 sq.ft.	$435,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 1.9% Airbnb Rental Income: $1115 Traditional Rental Income: $1440 Airbnb ROI: 0.18% Traditional ROI: 1.9%
17 RIDING TRAIL LN MADISON, VA Charming & Country Chic! Don't miss this beautiful 4 bedroom/3.5 bath Cape Cod on over 3.5...	4 beds \| 4 baths \| N/A	$524,900	Airbnb cash on cash: 1.75% Traditional cash on cash: 4.97% Airbnb Rental Income: $2212 Traditional Rental Income: $3235 Airbnb ROI: 1.75% Traditional ROI: 4.97%
205 N MAIN Street MADISON, VA Welcome to this rare 1836 Federal-style home set in Virginia's scenic countryside, with sw...	4 beds \| 3 baths \| 3,080 sq.ft.	$650,000	Airbnb cash on cash: 1.11% Traditional cash on cash: 3.59% Airbnb Rental Income: $2212 Traditional Rental Income: $3158 Airbnb ROI: 1.11% Traditional ROI: 3.59%
115 WASHINGTON Street MADISON, VA Experience the perfect blend of modern style and "in-town" convenience in this completely ...	4 beds \| 3 baths \| 1,692 sq.ft.	$395,000	Airbnb cash on cash: 2.7% Traditional cash on cash: 4.59% Airbnb Rental Income: $2212 Traditional Rental Income: $2353 Airbnb ROI: 2.7% Traditional ROI: 4.59%
399 SHELBY Road MADISON, VA This newly renovated 3-bed, 2-bath home in Madison County makes it easy to picture your li...	3 beds \| 2 baths \| 1,502 sq.ft.	$379,500	Airbnb cash on cash: N/A Traditional cash on cash: 2.98% Airbnb Rental Income: $1115 Traditional Rental Income: $1799 Airbnb ROI: N/A Traditional ROI: 2.98%
33 E CIRCLE Road MADISON, VA Available in May 2025 a modern two BR, two bath, central heat and A/C house situated on a ...	2 beds \| 2 baths \| 1,100 sq.ft.	$392,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 2.83% Airbnb Rental Income: $695 Traditional Rental Income: $1614 Airbnb ROI: -0.5% Traditional ROI: 2.83%
2004 TWYMANS MILL Road MADISON, VA Charming one-level home in Madison County with a perfect blend of country charm, yet just ...	3 beds \| 2 baths \| 1,708 sq.ft.	$359,999	Airbnb cash on cash: 0.44% Traditional cash on cash: 4.41% Airbnb Rental Income: $1115 Traditional Rental Income: $2083 Airbnb ROI: 0.44% Traditional ROI: 4.41%
Poorhouse Rd MADISON, VA Poorhouse Rd, MADISON, VA 22727 \| Other	N/A beds \| N/A baths \| N/A	$75,000	Airbnb cash on cash: -3.15% Traditional cash on cash: 3.73% Airbnb Rental Income: $219 Traditional Rental Income: $503 Airbnb ROI: -3.15% Traditional ROI: 3.73%
0 Main MADISON, VA 0 Main, MADISON, VA 22727 \| Other	N/A beds \| N/A baths \| N/A	$89,900	Airbnb cash on cash: -2.94% Traditional cash on cash: 2.86% Airbnb Rental Income: $219 Traditional Rental Income: $503 Airbnb ROI: -2.94% Traditional ROI: 2.86%
Jacks Shop Rd MADISON, VA Jacks Shop Rd, MADISON, VA 22727 \| Other	N/A beds \| N/A baths \| N/A	$149,000	Airbnb cash on cash: -2.51% Traditional cash on cash: 1.06% Airbnb Rental Income: $219 Traditional Rental Income: $503 Airbnb ROI: -2.51% Traditional ROI: 1.06%
Seminole MADISON, VA Seminole, MADISON, VA 22727 \| Other	N/A beds \| N/A baths \| N/A	$411,500	Airbnb cash on cash: -2.07% Traditional cash on cash: -0.75% Airbnb Rental Income: $219 Traditional Rental Income: $503 Airbnb ROI: -2.07% Traditional ROI: -0.75%
256 BLUE RIDGE MADISON, VA Public Open House Sunday May 3, 2026. There will be refreshments and Drawings for some pri...	4 beds \| 4 baths \| 2,290 sq.ft.	$599,000	Airbnb cash on cash: 1.31% Traditional cash on cash: 4.41% Airbnb Rental Income: $2212 Traditional Rental Income: $3386 Airbnb ROI: 1.31% Traditional ROI: 4.41%
453 LOST VALLEY Road MADISON, VA Mountain views, fresh air, and space to make it your own! Perched on a mountaintop in a pr...	3 beds \| 2 baths \| 1,486 sq.ft.	$375,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 3.9% Airbnb Rental Income: $1115 Traditional Rental Income: $1970 Airbnb ROI: 0.4% Traditional ROI: 3.9%
1830 Thrift Rd MADISON, VA 1830 Thrift Rd, MADISON, VA 22727 \| Single Family Residential	3 beds \| 2 baths \| 3,023 sq.ft.	$5,850,000	Airbnb cash on cash: -1.7% Traditional cash on cash: -1.49% Airbnb Rental Income: $1115 Traditional Rental Income: $1865 Airbnb ROI: -1.7% Traditional ROI: -1.49%
0 Tatum School Rd MADISON, VA 0 Tatum School Rd, MADISON, VA 22727 \| Other	N/A beds \| N/A baths \| N/A	$135,000	Airbnb cash on cash: -2.58% Traditional cash on cash: 1.46% Airbnb Rental Income: $219 Traditional Rental Income: $517 Airbnb ROI: -2.58% Traditional ROI: 1.46%
114 MARSHALL RD MADISON, VA Ranch style home in Madison County VA. This home features 3 bedrooms, 1 bath, an eat-in ki...	3 beds \| 1 baths \| 912 sq.ft.	$284,900	Airbnb cash on cash: 0.86% Traditional cash on cash: 3.91% Airbnb Rental Income: $1115 Traditional Rental Income: $1559 Airbnb ROI: 0.86% Traditional ROI: 3.91%
2123 OAK PARK MADISON, VA Escape the hustle and discover this rare, secluded gem nestled on over 10 private acres in...	3 beds \| 2 baths \| 1,344 sq.ft.	$540,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 2.26% Airbnb Rental Income: $1115 Traditional Rental Income: $1963 Airbnb ROI: -0.16% Traditional ROI: 2.26%
324 N Blue Ridge Tpke MADISON, VA 324 N Blue Ridge Tpke, MADISON, VA 22727 \| Single Family Residential	5 beds \| 2 baths \| 3,168 sq.ft.	$900,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 0.71% Airbnb Rental Income: $1455 Traditional Rental Income: $2210 Airbnb ROI: -0.7% Traditional ROI: 0.71%
114 Marshall MADISON, VA 114 Marshall, MADISON, VA 22727 \| Single Family Residential	3 beds \| 1 baths \| 912 sq.ft.	$284,900	Airbnb cash on cash: 0.6% Traditional cash on cash: 2.74% Airbnb Rental Income: $1115 Traditional Rental Income: $1316 Airbnb ROI: 0.6% Traditional ROI: 2.74%
359 Malvern Dr MADISON, VA 359 Malvern Dr, MADISON, VA 22727 \| Single Family Residential	4 beds \| 2 baths \| 1,812 sq.ft.	$465,000	Airbnb cash on cash: 1.65% Traditional cash on cash: 2.17% Airbnb Rental Income: $2212 Traditional Rental Income: $1881 Airbnb ROI: 1.65% Traditional ROI: 2.17%
1173 Aylor Rd MADISON, VA 1173 Aylor Rd, MADISON, VA 22727 \| Single Family Residential	4 beds \| 3 baths \| 2,280 sq.ft.	$390,000	Airbnb cash on cash: 2.45% Traditional cash on cash: 3.83% Airbnb Rental Income: $2212 Traditional Rental Income: $2158 Airbnb ROI: 2.45% Traditional ROI: 3.83%
LOT 2 S Ft Valley Rd MADISON, VA LOT 2 S Ft Valley Rd, MADISON, VA 22727 \| Other	N/A beds \| N/A baths \| N/A	$299,000	Airbnb cash on cash: -2.17% Traditional cash on cash: -0.06% Airbnb Rental Income: $219 Traditional Rental Income: $585 Airbnb ROI: -2.17% Traditional ROI: -0.06%
LOT 1 S Ft Valley Rd MADISON, VA LOT 1 S Ft Valley Rd, MADISON, VA 22727 \| Other	N/A beds \| N/A baths \| N/A	$309,000	Airbnb cash on cash: -2.16% Traditional cash on cash: -0.12% Airbnb Rental Income: $219 Traditional Rental Income: $585 Airbnb ROI: -2.16% Traditional ROI: -0.12%
850 OAK PARK MADISON, VA Enjoy your coffee with the sunrise on the back deck. Then take an afternoon break on the c...	2 beds \| 2 baths \| 897 sq.ft.	$387,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 3.06% Airbnb Rental Income: $695 Traditional Rental Income: $1630 Airbnb ROI: -0.36% Traditional ROI: 3.06%
298 COURTHOUSE MOUNTAIN LN MADISON, VA Woodhaven: an architectural sanctuary on 6.47 private acres in the Blue Ridge foothills. A...	3 beds \| 5 baths \| 4,993 sq.ft.	$885,000	Airbnb cash on cash: -0.55% Traditional cash on cash: 3.17% Airbnb Rental Income: $1115 Traditional Rental Income: $3805 Airbnb ROI: -0.55% Traditional ROI: 3.17%
Seminole Trl MADISON, VA Seminole Trl, MADISON, VA 22911 \| Other	N/A beds \| N/A baths \| N/A	$22,000,000	Airbnb cash on cash: -1.82% Traditional cash on cash: -1.79% Airbnb Rental Income: $219 Traditional Rental Income: $503 Airbnb ROI: -1.82% Traditional ROI: -1.79%
0 Mt Zion Church Rd MADISON, VA 0 Mt Zion Church Rd, MADISON, VA 22948 \| Other	N/A beds \| N/A baths \| N/A	$1,850,000	Airbnb cash on cash: -1.87% Traditional cash on cash: -1.33% Airbnb Rental Income: $219 Traditional Rental Income: $926 Airbnb ROI: -1.87% Traditional ROI: -1.33%

Real Estate investment in Madison, VA

There are 28 properties for sale in the city of Madison . The median list price in Madison is $417,900 and the average price per square foot is $226. In May 2026, the average monthly cash on cash return in Madison is 3.00%. The average monthly rental income in Madison is $1,707.

Madison, VA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 28 investment properties available for sale in Madison.

In 2026, the best neighborhood to buy investment property is MADISON.

The ROI for Short-Term is higher than the Long-Term in Madison with average rental income of $1,115.

Your search for investment property begins and ends here

Investment Property for Sale in Madison, VA

984 OAK PARK

MADISON, VA

3 beds | 2 baths | 1,942 sq.ft.

$420,000

Airbnb cash on cash: 0.33%

Traditional cash on cash: 4.02%

Airbnb Rental Income: $1115

Traditional Rental Income: $2194

Airbnb ROI: 0.33%

Traditional ROI: 4.02%

319 N Main St

MADISON, VA

3 beds | 1 baths | 2,744 sq.ft.

$435,000

Airbnb cash on cash: 0.18%

Traditional cash on cash: 1.9%

Airbnb Rental Income: $1115

Traditional Rental Income: $1440

Airbnb ROI: 0.18%

Traditional ROI: 1.9%

17 RIDING TRAIL LN

MADISON, VA

4 beds | 4 baths | N/A

$524,900

Airbnb cash on cash: 1.75%

Traditional cash on cash: 4.97%

Airbnb Rental Income: $2212

Traditional Rental Income: $3235

Airbnb ROI: 1.75%

Traditional ROI: 4.97%

205 N MAIN Street

MADISON, VA

4 beds | 3 baths | 3,080 sq.ft.

$650,000

Airbnb cash on cash: 1.11%

Traditional cash on cash: 3.59%

Airbnb Rental Income: $2212

Traditional Rental Income: $3158

Airbnb ROI: 1.11%

Traditional ROI: 3.59%

115 WASHINGTON Street

MADISON, VA

4 beds | 3 baths | 1,692 sq.ft.

$395,000

Airbnb cash on cash: 2.7%

Traditional cash on cash: 4.59%

Airbnb Rental Income: $2212

Traditional Rental Income: $2353

Airbnb ROI: 2.7%

Traditional ROI: 4.59%

399 SHELBY Road

MADISON, VA

3 beds | 2 baths | 1,502 sq.ft.

$379,500

Airbnb cash on cash: N/A

Traditional cash on cash: 2.98%

Airbnb Rental Income: $1115

Traditional Rental Income: $1799

Airbnb ROI: N/A

Traditional ROI: 2.98%

33 E CIRCLE Road

MADISON, VA

2 beds | 2 baths | 1,100 sq.ft.

$392,000

Airbnb cash on cash: -0.5%

Traditional cash on cash: 2.83%

Airbnb Rental Income: $695

Traditional Rental Income: $1614

Airbnb ROI: -0.5%

Traditional ROI: 2.83%

2004 TWYMANS MILL Road

MADISON, VA

3 beds | 2 baths | 1,708 sq.ft.

$359,999

Airbnb cash on cash: 0.44%

Traditional cash on cash: 4.41%

Airbnb Rental Income: $1115

Traditional Rental Income: $2083

Airbnb ROI: 0.44%