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
104 Half Penny Ln MADISON, VA Welcome to this beautifully maintained home in the desirable Malvern of Madison community,...	3 beds \| 3 baths \| 3,512 sq.ft.	$535,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 2.99% Airbnb Rental Income: $1800 Traditional Rental Income: $2391 Airbnb ROI: 0.83% Traditional ROI: 2.99%
399 Shelby Rd 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.	$350,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 3.38% Airbnb Rental Income: $1800 Traditional Rental Income: $1799 Airbnb ROI: 1.89% Traditional ROI: 3.38%
4578 Ruth Rd MADISON, VA Set amidst 17 beautifully landscaped acres, Monte Ventoso is an extraordinary Italian-insp...	5 beds \| 4 baths \| 5,153 sq.ft.	$4,450,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 0.03% Airbnb Rental Income: $3682 Traditional Rental Income: $5690 Airbnb ROI: -0.65% Traditional ROI: 0.03%
0 Main MADISON, VA 0 Main, MADISON, VA 22727 \| Other	N/A beds \| N/A baths \| N/A	$89,900	Airbnb cash on cash: 0.58% Traditional cash on cash: 2.86% Airbnb Rental Income: $590 Traditional Rental Income: $503 Airbnb ROI: 0.58% 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: -0.34% Traditional cash on cash: 1.06% Airbnb Rental Income: $590 Traditional Rental Income: $503 Airbnb ROI: -0.34% Traditional ROI: 1.06%
TBD Duet Rd MADISON, VA TBD Duet Rd, MADISON, VA 22727 \| Other	N/A beds \| N/A baths \| 1,728 sq.ft.	$165,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 3.47% Airbnb Rental Income: $590 Traditional Rental Income: $925 Airbnb ROI: -0.48% Traditional ROI: 3.47%
TBD Seminole Trl MADISON, VA TBD Seminole Trl, MADISON, VA 22727 \| Other	N/A beds \| N/A baths \| 1,120 sq.ft.	$1,100,000	Airbnb cash on cash: -1.61% Traditional cash on cash: -1.41% Airbnb Rental Income: $590 Traditional Rental Income: $503 Airbnb ROI: -1.61% Traditional ROI: -1.41%
Seminole MADISON, VA Seminole, MADISON, VA 22727 \| Other	N/A beds \| N/A baths \| N/A	$312,000	Airbnb cash on cash: -1.1% Traditional cash on cash: -0.42% Airbnb Rental Income: $590 Traditional Rental Income: $503 Airbnb ROI: -1.1% Traditional ROI: -0.42%
453 Lost Valley Rd 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.	$325,000	Airbnb cash on cash: 2.48% Traditional cash on cash: 4.64% Airbnb Rental Income: $1800 Traditional Rental Income: $1970 Airbnb ROI: 2.48% Traditional ROI: 4.64%
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: -1.59% Traditional cash on cash: -1.49% Airbnb Rental Income: $1800 Traditional Rental Income: $1865 Airbnb ROI: -1.59% 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	$125,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 1.71% Airbnb Rental Income: $590 Traditional Rental Income: $517 Airbnb ROI: -0.07% Traditional ROI: 1.71%
359 Malvern Dr MADISON, VA 359 Malvern Dr, MADISON, VA 22727 \| Single Family Residential	4 beds \| 2 baths \| 1,812 sq.ft.	$449,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 2.31% Airbnb Rental Income: $2317 Traditional Rental Income: $1881 Airbnb ROI: 1.98% Traditional ROI: 2.31%
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: -1.07% Traditional cash on cash: -0.06% Airbnb Rental Income: $590 Traditional Rental Income: $585 Airbnb ROI: -1.07% 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: -1.09% Traditional cash on cash: -0.12% Airbnb Rental Income: $590 Traditional Rental Income: $585 Airbnb ROI: -1.09% 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 \| 1 baths \| 897 sq.ft.	$375,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 3.26% Airbnb Rental Income: $1140 Traditional Rental Income: $1630 Airbnb ROI: 0.79% Traditional ROI: 3.26%
0 Goods Ln MADISON, VA 0 Goods Ln, MADISON, VA 22727 \| Other	N/A beds \| N/A baths \| N/A	$285,000	Airbnb cash on cash: -1.03% Traditional cash on cash: 0.02% Airbnb Rental Income: $590 Traditional Rental Income: $585 Airbnb ROI: -1.03% Traditional ROI: 0.02%
14 Surrey MADISON, VA Welcome home to three generously sized, light filled bedrooms on the main floor, with 2-1/...	3 beds \| 2 baths \| 2,404 sq.ft.	$498,999	Airbnb cash on cash: 0.99% Traditional cash on cash: 3.7% Airbnb Rental Income: $1800 Traditional Rental Income: $2576 Airbnb ROI: 0.99% Traditional ROI: 3.7%
221 S Honeysuckle Ln MADISON, VA 221 S Honeysuckle Ln, MADISON, VA 22727 \| Single Family Residential	2 beds \| 1 baths \| 874 sq.ft.	$286,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 1.58% Airbnb Rental Income: $1140 Traditional Rental Income: $1011 Airbnb ROI: 0.65% Traditional ROI: 1.58%
64 56a S Blueridge Tpke MADISON, VA 64 56a S Blueridge Tpke, MADISON, VA 22727 \| Other	N/A beds \| N/A baths \| N/A	$125,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 2.28% Airbnb Rental Income: $590 Traditional Rental Income: $585 Airbnb ROI: -0.07% Traditional ROI: 2.28%
TM 39-31&33b 31 & 33b Thrift Rd MADISON, VA TM 39-31&33b 31 & 33b Thrift Rd, MADISON, VA 22727 \| Other	N/A beds \| N/A baths \| N/A	$715,000	Airbnb cash on cash: -1.5% Traditional cash on cash: -1.08% Airbnb Rental Income: $590 Traditional Rental Income: $585 Airbnb ROI: -1.5% Traditional ROI: -1.08%
48-13o,13v&13u Tm 48-13o, 48-13u & 48-13v Courthouse Mountain Rd MADISON, VA 48-13o,13v&13u Tm 48-13o, 48-13u & 48-13v Courthouse Mountain Rd, MADISON, VA 22727 \| Othe...	N/A beds \| N/A baths \| N/A	$458,000	Airbnb cash on cash: -1.33% Traditional cash on cash: 0.03% Airbnb Rental Income: $590 Traditional Rental Income: $884 Airbnb ROI: -1.33% Traditional ROI: 0.03%
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.	$264,900	Airbnb cash on cash: 3.28% Traditional cash on cash: 4.27% Airbnb Rental Income: $1800 Traditional Rental Income: $1559 Airbnb ROI: 3.28% Traditional ROI: 4.27%
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: -1.8% Traditional cash on cash: -1.79% Airbnb Rental Income: $590 Traditional Rental Income: $503 Airbnb ROI: -1.8% 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	$1,450,000	Airbnb cash on cash: -1.66% Traditional cash on cash: -1.2% Airbnb Rental Income: $590 Traditional Rental Income: $926 Airbnb ROI: -1.66% Traditional ROI: -1.2%

Real Estate investment in Madison, VA

There are 29 properties for sale in the city of Madison . The median list price in Madison is $422,500 and the average price per square foot is $227. In July 2026, the average monthly cash on cash return in Madison is 2.00%. The average monthly rental income in Madison is $1,011.

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

There are 29 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 $1,140.

Your search for investment property begins and ends here

Investment Property for Sale in Madison, VA

104 Half Penny Ln

MADISON, VA

3 beds | 3 baths | 3,512 sq.ft.

$535,000

Airbnb cash on cash: 0.83%

Traditional cash on cash: 2.99%

Airbnb Rental Income: $1800

Traditional Rental Income: $2391

Airbnb ROI: 0.83%

Traditional ROI: 2.99%

399 Shelby Rd

MADISON, VA

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

$350,000

Airbnb cash on cash: 1.89%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $1800

Traditional Rental Income: $1799

Airbnb ROI: 1.89%

Traditional ROI: 3.38%

4578 Ruth Rd

MADISON, VA

5 beds | 4 baths | 5,153 sq.ft.

$4,450,000

Airbnb cash on cash: -0.65%

Traditional cash on cash: 0.03%

Airbnb Rental Income: $3682

Traditional Rental Income: $5690

Airbnb ROI: -0.65%

Traditional ROI: 0.03%

0 Main

MADISON, VA

N/A beds | N/A baths | N/A

$89,900

Airbnb cash on cash: 0.58%

Traditional cash on cash: 2.86%

Airbnb Rental Income: $590

Traditional Rental Income: $503

Airbnb ROI: 0.58%

Traditional ROI: 2.86%

Jacks Shop Rd

MADISON, VA

N/A beds | N/A baths | N/A

$149,000

Airbnb cash on cash: -0.34%

Traditional cash on cash: 1.06%

Airbnb Rental Income: $590

Traditional Rental Income: $503

Airbnb ROI: -0.34%

Traditional ROI: 1.06%

TBD Duet Rd

MADISON, VA

N/A beds | N/A baths | 1,728 sq.ft.

$165,000

Airbnb cash on cash: -0.48%

Traditional cash on cash: 3.47%

Airbnb Rental Income: $590

Traditional Rental Income: $925

Airbnb ROI: -0.48%

Traditional ROI: 3.47%

TBD Seminole Trl

MADISON, VA

N/A beds | N/A baths | 1,120 sq.ft.

$1,100,000

Airbnb cash on cash: -1.61%

Traditional cash on cash: -1.41%

Airbnb Rental Income: $590

Traditional Rental Income: $503

Airbnb ROI: -1.61%

Traditional ROI: -1.41%

Seminole

MADISON, VA

N/A beds | N/A baths | N/A

$312,000

Airbnb cash on cash: -1.1%

Traditional cash on cash: -0.42%

Airbnb Rental Income: $590

Traditional Rental Income: $503

Airbnb ROI: -1.1%