Real Estate Investment Properties for Sale in San Mateo, FL

Looking for investment property in San Mateo, FL with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
143 Pinecrest Circle SAN MATEO, FL Tucked Away on 2.16 Acres Backing Up to a Preserve, this 3610 SF, 4 Bed/2.5 Bath Home Offe...	4 beds \| 3 baths \| 3,610 sq.ft.	$474,900	Airbnb cash on cash: 1.92% Traditional cash on cash: 5.01% Airbnb Rental Income: $2206 Traditional Rental Income: $3022 Airbnb ROI: 1.92% Traditional ROI: 5.01%
134 Weerts Road SAN MATEO, FL Welcome to your brand-new home in peaceful San Mateo! This beautiful 3-bedroom, 2-bath man...	3 beds \| 2 baths \| 1,248 sq.ft.	$199,900	Airbnb cash on cash: 4.17% Traditional cash on cash: 8.75% Airbnb Rental Income: $1678 Traditional Rental Income: $2078 Airbnb ROI: 4.17% Traditional ROI: 8.75%
106 BREEZEWOOD Circle SAN MATEO, FL Nice 3 Bed 2 Ba Canal front DWMH leading to the St. Johns River. Has a new Metal Roof, New...	3 beds \| 2 baths \| 1,510 sq.ft.	$215,000	Airbnb cash on cash: 3.4% Traditional cash on cash: 9.41% Airbnb Rental Income: $1678 Traditional Rental Income: $2433 Airbnb ROI: 3.4% Traditional ROI: 9.41%
105 Breezewood Cir SAN MATEO, FL Welcome to this beautiful canal-front home in San Mateo, offering approximately canal fron...	3 beds \| 2 baths \| 1,620 sq.ft.	$225,000	Airbnb cash on cash: 2.9% Traditional cash on cash: 7.09% Airbnb Rental Income: $1678 Traditional Rental Income: $2101 Airbnb ROI: 2.9% Traditional ROI: 7.09%
108 N Bartram Trail SAN MATEO, FL Experience the ultimate riverfront lifestyle in this expansive 4-bedroom, 3.5-bathroom hom...	4 beds \| 4 baths \| 3,772 sq.ft.	$1,100,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 2.53% Airbnb Rental Income: $2206 Traditional Rental Income: $4989 Airbnb ROI: -0.73% Traditional ROI: 2.53%
126 EAST END Road SAN MATEO, FL Escape to the perfect blend of modern comfort and country charm with this beautifully upda...	3 beds \| 2 baths \| 1,400 sq.ft.	$309,900	Airbnb cash on cash: 2.3% Traditional cash on cash: 4.85% Airbnb Rental Income: $1678 Traditional Rental Income: $1953 Airbnb ROI: 2.3% Traditional ROI: 4.85%
132 PALMETTO POINT Lane SAN MATEO, FL Location, Location, Location! Experience peaceful country living in this charming San Mate...	3 beds \| 2 baths \| 1,320 sq.ft.	$183,995	Airbnb cash on cash: 3.92% Traditional cash on cash: 6.86% Airbnb Rental Income: $1678 Traditional Rental Income: $1723 Airbnb ROI: 3.92% Traditional ROI: 6.86%
123 KYTE Road SAN MATEO, FL Build your dream home on a full acre in the highly desirable San Mateo area! This thoughtf...	4 beds \| 2 baths \| 1,720 sq.ft.	$385,000	Airbnb cash on cash: 3.24% Traditional cash on cash: 4.93% Airbnb Rental Income: $2206 Traditional Rental Income: $2258 Airbnb ROI: 3.24% Traditional ROI: 4.93%

Real Estate investment in San-mateo, FL

There are 8 properties for sale in the city of San Mateo . The median list price in San Mateo is $1,488,890 and the average price per square foot is $852. In September 2026, the average monthly cash on cash return in San Mateo is 7.00%. The average monthly rental income in San Mateo is $2,101.

San-mateo, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 8 investment properties available for sale in San-mateo.

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

The ROI for Long-Term is higher than the Short-Term in San-mateo with average rental income of $2,101.

Your search for investment property begins and ends here

Investment Property for Sale in San Mateo, FL

143 Pinecrest Circle

SAN MATEO, FL

4 beds | 3 baths | 3,610 sq.ft.

$474,900

Airbnb cash on cash: 1.92%

Traditional cash on cash: 5.01%

Airbnb Rental Income: $2206

Traditional Rental Income: $3022

Airbnb ROI: 1.92%

Traditional ROI: 5.01%

134 Weerts Road

SAN MATEO, FL

3 beds | 2 baths | 1,248 sq.ft.

$199,900

Airbnb cash on cash: 4.17%

Traditional cash on cash: 8.75%

Airbnb Rental Income: $1678

Traditional Rental Income: $2078

Airbnb ROI: 4.17%

Traditional ROI: 8.75%

106 BREEZEWOOD Circle

SAN MATEO, FL

3 beds | 2 baths | 1,510 sq.ft.

$215,000

Airbnb cash on cash: 3.4%

Traditional cash on cash: 9.41%

Airbnb Rental Income: $1678

Traditional Rental Income: $2433

Airbnb ROI: 3.4%

Traditional ROI: 9.41%

105 Breezewood Cir

SAN MATEO, FL

3 beds | 2 baths | 1,620 sq.ft.

$225,000

Airbnb cash on cash: 2.9%

Traditional cash on cash: 7.09%

Airbnb Rental Income: $1678

Traditional Rental Income: $2101

Airbnb ROI: 2.9%

Traditional ROI: 7.09%

108 N Bartram Trail

SAN MATEO, FL

4 beds | 4 baths | 3,772 sq.ft.

$1,100,000

Airbnb cash on cash: -0.73%

Traditional cash on cash: 2.53%

Airbnb Rental Income: $2206

Traditional Rental Income: $4989

Airbnb ROI: -0.73%

Traditional ROI: 2.53%

126 EAST END Road

SAN MATEO, FL

3 beds | 2 baths | 1,400 sq.ft.

$309,900

Airbnb cash on cash: 2.3%

Traditional cash on cash: 4.85%

Airbnb Rental Income: $1678

Traditional Rental Income: $1953

Airbnb ROI: 2.3%

Traditional ROI: 4.85%

132 PALMETTO POINT Lane

SAN MATEO, FL

3 beds | 2 baths | 1,320 sq.ft.

$183,995

Airbnb cash on cash: 3.92%

Traditional cash on cash: 6.86%

Airbnb Rental Income: $1678

Traditional Rental Income: $1723

Airbnb ROI: 3.92%

Traditional ROI: 6.86%

123 KYTE Road

SAN MATEO, FL

4 beds | 2 baths | 1,720 sq.ft.

$385,000

Airbnb cash on cash: 3.24%

Traditional cash on cash: 4.93%

Airbnb Rental Income: $2206

Traditional Rental Income: $2258

Airbnb ROI: 3.24%