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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
2271 SW Oregon TrlMADISON, FL2271 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%
|
1048 NE Duval Pond RoadMADISON, FLWelcome 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%
|
1262 N State Road 53MADISON, FLThere's something special about finding a home that offers both space to breathe and comfo... |
3 beds | 2 baths | 2,032 sq.ft. |
$439,000 |
Airbnb cash on cash: 5.23%
|
542 NE Horry AveMADISON, FLWelcome to your dream home in the heart of downtown Madison! Nestled on a spacious corner ... |
3 beds | 2 baths | 3,057 sq.ft. |
$532,000 |
Airbnb cash on cash: 3.99%
|
1983 E US 90 HighwayMADISON, FLBrick 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%
|
916 SW Cr 360MADISON, FLExpansive 50.5-Acre Estate with 4-Bedroom Home & Agricultural Potential Discover the perfe... |
N/A beds | N/A baths | 3,206 sq.ft. |
$340,000 |
Airbnb cash on cash: 1.96%
|
3704 NE ROCKY FORD RoadMADISON, FLSitting upon a full acre this west facing 15-year young 5 BR, 3BA home, features timeless ... |
5 beds | 3 baths | 3,452 sq.ft. |
$449,900 |
Airbnb cash on cash: N/A
|
6175 NE Colin Kelly HighwayMADISON, FLCharming 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%
|
3500 NE Rocky Ford RdMADISON, FL3500 NE Rocky Ford Rd, MADISON, FL 32340 | Other |
N/A beds | N/A baths | N/A |
$512,400 |
Airbnb cash on cash: 0.68%
|
VACANT88 NE Rocky Ford RdMADISON, FLVACANT88 NE Rocky Ford Rd, MADISON, FL 32340 | Other |
N/A beds | N/A baths | N/A |
$882,000 |
Airbnb cash on cash: -0.39%
|
3600 NE Rocky Ford RdMADISON, FL3600 NE Rocky Ford Rd, MADISON, FL 32340 | Other |
N/A beds | N/A baths | N/A |
$413,700 |
Airbnb cash on cash: 1.29%
|
241 SW Canopy TrlMADISON, FL241 SW Canopy Trl, MADISON, FL 32340 | Single Family Residential |
3 beds | 2 baths | 1,898 sq.ft. |
$399,900 |
Airbnb cash on cash: 5.91%
|
1055 NE Cherry Lake CirMADISON, FLEnjoy the beauty of lakefront living with this newly renovated 3 bedroom, 3 bathroom home ... |
3 beds | 3 baths | 2,040 sq.ft. |
$675,000 |
Airbnb cash on cash: 2.76%
|
1217 SW Caleb AveMADISON, FL1217 SW Caleb Ave, MADISON, FL 32340 | Other |
N/A beds | N/A baths | N/A |
$450,000 |
Airbnb cash on cash: 1.03%
|
TBD SW Harvey Greene DrMADISON, FLTBD SW Harvey Greene Dr, MADISON, FL 32340 | Other |
N/A beds | N/A baths | N/A |
$120,000 |
Airbnb cash on cash: 8.74%
|
5001 NW Little Cat RdMADISON, FL5001 NW Little Cat Rd, MADISON, FL 32340 | Other |
N/A beds | N/A baths | N/A |
$315,000 |
Airbnb cash on cash: 2.26%
|
651 NW Flowers RdMADISON, FL651 NW Flowers Rd, MADISON, FL 32340 | Other |
N/A beds | N/A baths | N/A |
$234,000 |
Airbnb cash on cash: 3.67%
|
1537 NE Cherry Lake CirMADISON, FL1537 NE Cherry Lake Cir, MADISON, FL 32340 | Other |
N/A beds | N/A baths | N/A |
$375,000 |
Airbnb cash on cash: 1.61%
|
4900 NW Florwers Rd RdMADISON, FL650 NW Florwers Rd Rd, MADISON, FL 32340 | Other |
N/A beds | N/A baths | N/A |
$550,000 |
Airbnb cash on cash: 0.51%
|
1341 NE Cherry Lake CirMADISON, FL1341 NE Cherry Lake Cir, MADISON, FL 32340 | Other |
N/A beds | N/A baths | N/A |
$425,000 |
Airbnb cash on cash: 1.2%
|
Vacant SW Hike Lake RdMADISON, FLVacant 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%
|
5000 NW Little Cat RdMADISON, FL5000 NW Little Cat Rd, MADISON, FL 32340 | Other |
N/A beds | N/A baths | N/A |
$370,500 |
Airbnb cash on cash: 1.65%
|
8412 SW Tower RdMADISON, FL8412 SW Tower Rd, MADISON, FL 32340 | Other |
N/A beds | N/A baths | N/A |
$499,000 |
Airbnb cash on cash: 0.75%
|
3639 N SR 53MADISON, FLSpacious, beautifully renovated 3 bedroom, 2 bathroom home situated on 8.63 acres on paved... |
3 beds | 2 baths | 2,899 sq.ft. |
$475,000 |
Airbnb cash on cash: 4.69%
|
TBD NE Duval Pond RdMADISON, FLTBD NE Duval Pond Rd, MADISON, FL 32340 | Other |
N/A beds | N/A baths | N/A |
$875,000 |
Airbnb cash on cash: -0.38%
|
511 SW Sundown Creek RdMADISON, FLNestled in the rolling countryside of Madison County, FL, this stunning 40-acre property o... |
3 beds | 2 baths | 1,938 sq.ft. |
$657,500 |
Airbnb cash on cash: 2.88%
|
1914 SW JIm Clark RdMADISON, FLTurnkey 40.23-Acre Livestock & Recreational Property with Home, Cross-Fencing & Cypress Po... |
3 beds | 2 baths | 2,079 sq.ft. |
$350,000 |
Airbnb cash on cash: 7.01%
|
4219 NE Cherry Lake CircleMADISON, FLWake up to breathtaking sunrises and unwind with unforgettable sunsets on Cherry Lake-one ... |
3 beds | 2 baths | 1,655 sq.ft. |
$649,000 |
Airbnb cash on cash: 2.86%
|
231 SW Rutledge StMADISON, FLStep into timeless charm with this beautifully maintained Folk Victorian-era home in the h... |
4 beds | 3 baths | 3,910 sq.ft. |
$500,000 |
Airbnb cash on cash: 5.99%
|
870 SW San Pedro RdMADISON, FL870 SW San Pedro Rd, MADISON, FL 32340 | Other |
N/A beds | N/A baths | N/A |
$244,500 |
Airbnb cash on cash: 3.44%
|
652 NW Flowers RdMADISON, FL652 NW Flowers Rd, MADISON, FL 32340 | Other |
N/A beds | N/A baths | N/A |
$130,000 |
Airbnb cash on cash: 7.96%
|
324 NE Fraleigh DriveMADISON, FLLivingston Springs Subdivision - Madison, FL 4 Bedroom / 4 Bathroom Home located in the hi... |
4 beds | 4 baths | 2,869 sq.ft. |
$449,000 |
Airbnb cash on cash: 7.2%
|
1752 SE ROGERS SINK RoadMADISON, FLWelcome to your own private slice of North Florida paradise mini farm -where timeless char... |
3 beds | 2 baths | 2,864 sq.ft. |
$789,000 |
Airbnb cash on cash: 2.66%
|
6511 NW Flowers RdMADISON, FL6511 NW Flowers Rd, MADISON, FL 32340 | Other |
N/A beds | N/A baths | N/A |
$120,000 |
Airbnb cash on cash: 8.74%
|
2432 SW Sr 14MADISON, FL2432 SW Sr 14, MADISON, FL 32340 | Single Family Residential |
3 beds | 2 baths | 2,016 sq.ft. |
$390,000 |
Airbnb cash on cash: 6.11%
|
1404 NE Duval Pond RdMADISON, FL1404 NE Duval Pond Rd, MADISON, FL 32340 | Other |
N/A beds | N/A baths | N/A |
$150,000 |
Airbnb cash on cash: 6.68%
|
402 NW CanteyMADISON, FLNestled on 2.44 private acres surrounded by abundant wildlife, this beautifully maintained... |
3 beds | 3 baths | 2,944 sq.ft. |
$470,000 |
Airbnb cash on cash: 4.76%
|
153 SW Canopy TrlMADISON, FL153 SW Canopy Trl, MADISON, FL 32340 | Single Family Residential |
3 beds | 2 baths | 2,002 sq.ft. |
$559,000 |
Airbnb cash on cash: 3.71%
|
Vacant SW Captain Brown RdMADISON, FLVacant SW Captain Brown Rd, MADISON, FL 32340 | Other |
N/A beds | N/A baths | N/A |
$115,000 |
Airbnb cash on cash: 9.18%
|
422 NW College LoopMADISON, FL422 NW College Loop, MADISON, FL 32340 | Single Family Residential |
4 beds | 3 baths | 2,241 sq.ft. |
$442,000 |
Airbnb cash on cash: 7.01%
|
Real Estate investment in Madison, FL
There are 47 properties for sale in the city of Madison . The median list price in Madison is $145,363 and the average price per square foot is $78. In July 2026, the average monthly cash on cash return in Madison is 5.00%. The average monthly rental income in Madison is $1,609.