Real Estate Investment Properties for Sale in Madison, FL

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

Explore a variety of short-term homes & houses in Madison, FL. Invest wisely with VRBO & Madison, FL 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, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2271 SW Oregon Trl MADISON, FL 2271 SW Oregon Trl, MADISON, FL 32331 \| Other	N/A beds \| N/A baths \| 1,350 sq.ft.	$325,000	Airbnb cash on cash: 2.14% Traditional cash on cash: 0.52% Airbnb Rental Income: $1813 Traditional Rental Income: $827 Airbnb ROI: 2.14% Traditional ROI: 0.52%
000 W Us 90 MADISON, FL 000 W Us 90, MADISON, FL 32331 \| Other	N/A beds \| N/A baths \| N/A	$250,000	Airbnb cash on cash: 2.54% Traditional cash on cash: 0.03% Airbnb Rental Income: $1813 Traditional Rental Income: $625 Airbnb ROI: 2.54% Traditional ROI: 0.03%
1048 NE Duval Pond Rd MADISON, FL Welcome to this beautiful 57+ acre horse farm offering the perfect blend of country living...	3 beds \| 2 baths \| 1,596 sq.ft.	$790,000	Airbnb cash on cash: 2.74% Traditional cash on cash: 0.44% Airbnb Rental Income: $3846 Traditional Rental Income: $1322 Airbnb ROI: 2.74% Traditional ROI: 0.44%
479 NW Appaloosa Way MADISON, FL Experience exceptional craftsmanship in this custom-built home set on over five peaceful a...	4 beds \| 3 baths \| 3,809 sq.ft.	$685,500	Airbnb cash on cash: 3.96% Traditional cash on cash: 2.6% Airbnb Rental Income: $4757 Traditional Rental Income: $2906 Airbnb ROI: 3.96% Traditional ROI: 2.6%
370 NE Gardenia Way MADISON, FL Phenomenal 5 bedroom 3 1/2 bathroom home located in beautiful Madison County, FL! Embrace ...	5 beds \| 3 baths \| 2,836 sq.ft.	$585,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.44% Airbnb Rental Income: $null Traditional Rental Income: $3790 Airbnb ROI: N/A Traditional ROI: 5.44%
186 NW Whispering Pines Loop MADISON, FL Seller Motivated...New roof in 2024! This custom-built home offers exceptional space and c...	3 beds \| 3 baths \| 2,682 sq.ft.	$300,000	Airbnb cash on cash: 8.86% Traditional cash on cash: 8.17% Airbnb Rental Income: $3846 Traditional Rental Income: $2823 Airbnb ROI: 8.86% Traditional ROI: 8.17%
1983 E Us 90 Hwy MADISON, FL Brick Home on 3 Acres - Minutes from Downtown Madison, FL! Address: 1983 E US 90, Madison,...	3 beds \| 3 baths \| 1,959 sq.ft.	$399,900	Airbnb cash on cash: 5.89% Traditional cash on cash: 5.87% Airbnb Rental Income: $3846 Traditional Rental Income: $3008 Airbnb ROI: 5.89% Traditional ROI: 5.87%
396 NW Gadwall Way MADISON, FL Step Back in Time with This 1870 Florida Southern Dogtrot 5 Bedroom 2 1/2 bath home. His...	5 beds \| 3 baths \| 3,393 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.12% Airbnb Rental Income: $null Traditional Rental Income: $3541 Airbnb ROI: N/A Traditional ROI: 8.12%
9849 N Sr 53 MADISON, FL Imagine waking up to birdsong and sipping coffee as the morning mist rises over Elbow Pond...	2 beds \| 2 baths \| 2,008 sq.ft.	$360,000	Airbnb cash on cash: 4.68% Traditional cash on cash: 4.38% Airbnb Rental Income: $2856 Traditional Rental Income: $2089 Airbnb ROI: 4.68% Traditional ROI: 4.38%
916 SW Cr 360 MADISON, FL Expansive 50.5-Acre Estate with 4-Bedroom Home & Agricultural Potential Discover the perfe...	4 beds \| 3 baths \| 3,206 sq.ft.	$799,000	Airbnb cash on cash: 3.06% Traditional cash on cash: 2.99% Airbnb Rental Income: $4757 Traditional Rental Income: $3719 Airbnb ROI: 3.06% Traditional ROI: 2.99%
3704 NE Rocky Ford Rd MADISON, FL NEW LOWER PRICE!! Sitting upon a full acre this west facing 15-year young 5 BR, 3BA home, ...	5 beds \| 3 baths \| 3,452 sq.ft.	$468,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.67% Airbnb Rental Income: $null Traditional Rental Income: $3410 Airbnb ROI: N/A Traditional ROI: 4.67%
402 NW Cantey Ave MADISON, FL 402 NW Cantey Ave Prime Location - peaceful setting with the charm of country living while...	3 beds \| 3 baths \| 2,944 sq.ft.	$480,000	Airbnb cash on cash: 4.94% Traditional cash on cash: 4.08% Airbnb Rental Income: $3846 Traditional Rental Income: $2629 Airbnb ROI: 4.94% Traditional ROI: 4.08%
6175 NE Colin Kelly Hwy MADISON, FL Charming Brick Home on 1 Acre - Peaceful Country Living! Discover this beautiful 2-bedroom...	2 beds \| 2 baths \| 1,552 sq.ft.	$259,900	Airbnb cash on cash: 7.28% Traditional cash on cash: 5.97% Airbnb Rental Income: $2856 Traditional Rental Income: $1870 Airbnb ROI: 7.28% Traditional ROI: 5.97%
4339 NE Cherry Lake Cir MADISON, FL Water-lover's paradise! This lake home oasis is off the beaten path in the quaint county o...	3 beds \| 2 baths \| 1,586 sq.ft.	$799,000	Airbnb cash on cash: 2.4% Traditional cash on cash: 1.36% Airbnb Rental Income: $3846 Traditional Rental Income: $2247 Airbnb ROI: 2.4% Traditional ROI: 1.36%
3618 Country Kitchen Rd MADISON, FL 3618 Country Kitchen Rd, MADISON, FL 32340 \| Single Family Residential	3 beds \| 2 baths \| 2,853 sq.ft.	$549,900	Airbnb cash on cash: 3.81% Traditional cash on cash: 1.69% Airbnb Rental Income: $3846 Traditional Rental Income: $1928 Airbnb ROI: 3.81% Traditional ROI: 1.69%
241 SW Canopy Trl MADISON, FL 241 SW Canopy Trl, MADISON, FL 32340 \| Single Family Residential	3 beds \| 2 baths \| 1,898 sq.ft.	$389,000	Airbnb cash on cash: 6.13% Traditional cash on cash: 3.13% Airbnb Rental Income: $3846 Traditional Rental Income: $1924 Airbnb ROI: 6.13% Traditional ROI: 3.13%
983 NW St Thomas Church Rd MADISON, FL 983 NW St Thomas Church Rd, MADISON, FL 32340 \| Single Family Residential	4 beds \| 2 baths \| 2,384 sq.ft.	$399,000	Airbnb cash on cash: 7.96% Traditional cash on cash: 3.21% Airbnb Rental Income: $4757 Traditional Rental Income: $1998 Airbnb ROI: 7.96% Traditional ROI: 3.21%
319 SE Bunker St MADISON, FL 319 SE Bunker St, MADISON, FL 32340 \| Single Family Residential	3 beds \| 2 baths \| 1,612 sq.ft.	$299,000	Airbnb cash on cash: 7.68% Traditional cash on cash: 3.13% Airbnb Rental Income: $3846 Traditional Rental Income: $1626 Airbnb ROI: 7.68% Traditional ROI: 3.13%
1217 SW Caleb Ave MADISON, FL 1217 SW Caleb Ave, MADISON, FL 32340 \| Other	N/A beds \| N/A baths \| N/A	$450,000	Airbnb cash on cash: 1.03% Traditional cash on cash: -0.58% Airbnb Rental Income: $1813 Traditional Rental Income: $642 Airbnb ROI: 1.03% Traditional ROI: -0.58%
TBD SW Harvey Greene Dr MADISON, FL TBD SW Harvey Greene Dr, MADISON, FL 32340 \| Other	N/A beds \| N/A baths \| N/A	$135,000	Airbnb cash on cash: 7.6% Traditional cash on cash: 2.23% Airbnb Rental Income: $1813 Traditional Rental Income: $625 Airbnb ROI: 7.6% Traditional ROI: 2.23%
5001 NW Little Cat Rd MADISON, FL 5001 NW Little Cat Rd, MADISON, FL 32340 \| Other	N/A beds \| N/A baths \| N/A	$315,000	Airbnb cash on cash: 2.26% Traditional cash on cash: -0.09% Airbnb Rental Income: $1813 Traditional Rental Income: $625 Airbnb ROI: 2.26% Traditional ROI: -0.09%
183 SW Jim Clark Rd MADISON, FL 183 SW Jim Clark Rd, MADISON, FL 32340 \| Other	N/A beds \| N/A baths \| N/A	$197,000	Airbnb cash on cash: 4.69% Traditional cash on cash: 1.05% Airbnb Rental Income: $1813 Traditional Rental Income: $642 Airbnb ROI: 4.69% Traditional ROI: 1.05%
651 NW Flowers Rd MADISON, FL 651 NW Flowers Rd, MADISON, FL 32340 \| Other	N/A beds \| N/A baths \| N/A	$378,000	Airbnb cash on cash: 1.58% Traditional cash on cash: -0.38% Airbnb Rental Income: $1813 Traditional Rental Income: $625 Airbnb ROI: 1.58% Traditional ROI: -0.38%
SE Gunpowder Ave MADISON, FL SE Gunpowder Ave, MADISON, FL 32340 \| Other	N/A beds \| N/A baths \| N/A	$159,900	Airbnb cash on cash: 6.17% Traditional cash on cash: 1.86% Airbnb Rental Income: $1813 Traditional Rental Income: $664 Airbnb ROI: 6.17% Traditional ROI: 1.86%
1537 NE Cherry Lake Cir MADISON, FL 1537 NE Cherry Lake Cir, MADISON, FL 32340 \| Other	N/A beds \| N/A baths \| N/A	$375,000	Airbnb cash on cash: 1.61% Traditional cash on cash: -0.37% Airbnb Rental Income: $1813 Traditional Rental Income: $625 Airbnb ROI: 1.61% Traditional ROI: -0.37%
650 NW Florwers Rd Rd MADISON, FL 650 NW Florwers Rd Rd, MADISON, FL 32340 \| Other	N/A beds \| N/A baths \| N/A	$790,500	Airbnb cash on cash: -0.22% Traditional cash on cash: -1.16% Airbnb Rental Income: $1813 Traditional Rental Income: $625 Airbnb ROI: -0.22% Traditional ROI: -1.16%
1341 NE Cherry Lake Cir MADISON, FL 1341 NE Cherry Lake Cir, MADISON, FL 32340 \| Other	N/A beds \| N/A baths \| N/A	$425,000	Airbnb cash on cash: 1.2% Traditional cash on cash: -0.52% Airbnb Rental Income: $1813 Traditional Rental Income: $635 Airbnb ROI: 1.2% Traditional ROI: -0.52%
000 NE Delphinium Dr MADISON, FL 000 NE Delphinium Dr, MADISON, FL 32340 \| Other	N/A beds \| N/A baths \| N/A	$1,750,000	Airbnb cash on cash: -1.13% Traditional cash on cash: -1.54% Airbnb Rental Income: $1813 Traditional Rental Income: $647 Airbnb ROI: -1.13% Traditional ROI: -1.54%
0000 NE Dandelion St MADISON, FL 0000 NE Dandelion St, MADISON, FL 32340 \| Other	N/A beds \| N/A baths \| N/A	$335,000	Airbnb cash on cash: 2.02% Traditional cash on cash: -0.12% Airbnb Rental Income: $1813 Traditional Rental Income: $647 Airbnb ROI: 2.02% Traditional ROI: -0.12%
0 NW Cr 253 MADISON, FL 0 NW Cr 253, MADISON, FL 32340 \| Other	N/A beds \| N/A baths \| N/A	$265,000	Airbnb cash on cash: 3.03% Traditional cash on cash: 0.24% Airbnb Rental Income: $1813 Traditional Rental Income: $625 Airbnb ROI: 3.03% Traditional ROI: 0.24%
Vacant SW Hike Lake Rd MADISON, FL Vacant SW Hike Lake Rd, MADISON, FL 32340 \| Other	N/A beds \| N/A baths \| N/A	$1,551,000	Airbnb cash on cash: -1.03% Traditional cash on cash: -1.5% Airbnb Rental Income: $1813 Traditional Rental Income: $642 Airbnb ROI: -1.03% Traditional ROI: -1.5%
0 NW Cr 253 Lot 1 MADISON, FL 0 NW Cr 253 Lot 1, MADISON, FL 32340 \| Other	N/A beds \| N/A baths \| N/A	$139,500	Airbnb cash on cash: 7.31% Traditional cash on cash: 2.1% Airbnb Rental Income: $1813 Traditional Rental Income: $625 Airbnb ROI: 7.31% Traditional ROI: 2.1%
000 NW Cr 253 Lot 2 MADISON, FL 000 NW Cr 253 Lot 2, MADISON, FL 32340 \| Other	N/A beds \| N/A baths \| N/A	$135,000	Airbnb cash on cash: 7.6% Traditional cash on cash: 2.23% Airbnb Rental Income: $1813 Traditional Rental Income: $625 Airbnb ROI: 7.6% Traditional ROI: 2.23%
NE Bittersweet Trl MADISON, FL NE Bittersweet Trl, MADISON, FL 32340 \| Other	N/A beds \| N/A baths \| 616 sq.ft.	$375,000	Airbnb cash on cash: 1.61% Traditional cash on cash: -0.37% Airbnb Rental Income: $1813 Traditional Rental Income: $625 Airbnb ROI: 1.61% Traditional ROI: -0.37%
xxx NE Geranium St MADISON, FL xxx NE Geranium St, MADISON, FL 32340 \| Other	N/A beds \| N/A baths \| N/A	$760,000	Airbnb cash on cash: -0.15% Traditional cash on cash: -1.1% Airbnb Rental Income: $1813 Traditional Rental Income: $647 Airbnb ROI: -0.15% Traditional ROI: -1.1%
5000 NW Little Cat Rd MADISON, FL 5000 NW Little Cat Rd, MADISON, FL 32340 \| Other	N/A beds \| N/A baths \| N/A	$598,500	Airbnb cash on cash: 0.32% Traditional cash on cash: -0.93% Airbnb Rental Income: $1813 Traditional Rental Income: $625 Airbnb ROI: 0.32% Traditional ROI: -0.93%
TBD NE Daisy St MADISON, FL TBD NE Daisy St, MADISON, FL 32340 \| Other	N/A beds \| N/A baths \| 3,960 sq.ft.	$2,499,000	Airbnb cash on cash: -1.35% Traditional cash on cash: -1.65% Airbnb Rental Income: $1813 Traditional Rental Income: $647 Airbnb ROI: -1.35% Traditional ROI: -1.65%

Real Estate investment in Madison, FL

There are 44 properties for sale in the city of Madison . The median list price in Madison is $369,900 and the average price per square foot is $206. In March 2026, the average monthly cash on cash return in Madison is 4.00%. The average monthly rental income in Madison is $827.

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

There are 44 investment properties available for sale in Madison.

The ROI for Short-Term is higher than the Long-Term in Madison with average rental income of $1,813.

Your search for investment property begins and ends here

Investment Property for Sale in Madison, FL

2271 SW Oregon Trl

MADISON, FL

N/A beds | N/A baths | 1,350 sq.ft.

$325,000

Airbnb cash on cash: 2.14%

Traditional cash on cash: 0.52%

Airbnb Rental Income: $1813

Traditional Rental Income: $827

Airbnb ROI: 2.14%

Traditional ROI: 0.52%

000 W Us 90

MADISON, FL

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

$250,000

Airbnb cash on cash: 2.54%

Traditional cash on cash: 0.03%

Airbnb Rental Income: $1813

Traditional Rental Income: $625

Airbnb ROI: 2.54%

Traditional ROI: 0.03%

1048 NE Duval Pond Rd

MADISON, FL

3 beds | 2 baths | 1,596 sq.ft.

$790,000

Airbnb cash on cash: 2.74%

Traditional cash on cash: 0.44%

Airbnb Rental Income: $3846

Traditional Rental Income: $1322

Airbnb ROI: 2.74%

Traditional ROI: 0.44%

479 NW Appaloosa Way

MADISON, FL

4 beds | 3 baths | 3,809 sq.ft.

$685,500

Airbnb cash on cash: 3.96%

Traditional cash on cash: 2.6%

Airbnb Rental Income: $4757

Traditional Rental Income: $2906

Airbnb ROI: 3.96%

Traditional ROI: 2.6%

370 NE Gardenia Way

MADISON, FL

5 beds | 3 baths | 2,836 sq.ft.

$585,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.44%

Airbnb Rental Income: $null

Traditional Rental Income: $3790

Airbnb ROI: N/A

Traditional ROI: 5.44%

186 NW Whispering Pines Loop

MADISON, FL

3 beds | 3 baths | 2,682 sq.ft.

$300,000

Airbnb cash on cash: 8.86%

Traditional cash on cash: 8.17%

Airbnb Rental Income: $3846

Traditional Rental Income: $2823

Airbnb ROI: 8.86%

Traditional ROI: 8.17%

1983 E Us 90 Hwy

MADISON, FL

3 beds | 3 baths | 1,959 sq.ft.

$399,900

Airbnb cash on cash: 5.89%

Traditional cash on cash: 5.87%

Airbnb Rental Income: $3846

Traditional Rental Income: $3008

Airbnb ROI: 5.89%

Traditional ROI: 5.87%

396 NW Gadwall Way

MADISON, FL

5 beds | 3 baths | 3,393 sq.ft.

$399,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.12%

Airbnb Rental Income: $null

Traditional Rental Income: $3541

Airbnb ROI: N/A