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.

Single Family Homes for Sale in San Mateo, FL

Search for Single Family Residential for Sale in San Mateo, Florida. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 4 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
129 Divi Divi Dr SAN MATEO, FL Welcome To This Inviting,3-bedroom,3-bath Retreat On 1+ Acre Estate Lot Nestled Within A P...	3 beds \| 3 baths \| 3,189 sq.ft.	$529,000	Airbnb cash on cash: 3.3% Traditional cash on cash: 4.09% Airbnb Rental Income: $3571 Traditional Rental Income: $3177 Airbnb ROI: 3.3% Traditional ROI: 4.09%
143 Pinecrest Circle SAN MATEO, FL Luxurious 4 BR/2.5 BA, 3876 sf home on 2.16 acres near St. Augustine, blending rural charm...	4 beds \| 3 baths \| 3,876 sq.ft.	$524,900	Airbnb cash on cash: 5.49% Traditional cash on cash: 4.49% Airbnb Rental Income: $4441 Traditional Rental Income: $3022 Airbnb ROI: 5.49% Traditional ROI: 4.49%
689 S HIGHWAY17 SAN MATEO, FL Back on the market due to no fault of its own. Open House 4/18/2026 from 12-2. Have you be...	3 beds \| 2 baths \| 1,668 sq.ft.	$650,000	Airbnb cash on cash: 2.9% Traditional cash on cash: 2.51% Airbnb Rental Income: $3571 Traditional Rental Income: $2548 Airbnb ROI: 2.9% Traditional ROI: 2.51%
156 Crosby Rd SAN MATEO, FL Purchase this home, if YOU Are Not Satisfied, We'll SELL IT FOR FREE! *First Responders an...	4 beds \| 3 baths \| 3,233 sq.ft.	$549,900	Airbnb cash on cash: 4.77% Traditional cash on cash: 6.35% Airbnb Rental Income: $4441 Traditional Rental Income: $4324 Airbnb ROI: 4.77% Traditional ROI: 6.35%
Other Single Family Residential Investment Properties for Sale in Florida
14825 Front Beach Rd #511 Panama City Beach , FL BIGGEST AND BEST IN SUNRISE BEACH! HANDS DOWN THE NICEST UNIT IN THE DEVELOPMENT. BEST FLO...	3 beds \| 3 baths \| 1,565 sq.ft.	$777,000	Airbnb cash on cash: -1.81% Traditional cash on cash: -0.08% Airbnb Rental Income: $1279 Traditional Rental Income: $2128 Airbnb ROI: -1.81% Traditional ROI: -0.08%
9492 Buck Haven Trail Tallahassee , FL Located in the desirable Killearn Lakes subdivision, this home is within walking distance ...	3 beds \| 2 baths \| 1,562 sq.ft.	$339,500	Airbnb cash on cash: -0.2% Traditional cash on cash: 3.44% Airbnb Rental Income: $993 Traditional Rental Income: $1799 Airbnb ROI: -0.2% Traditional ROI: 3.44%
2661 HAWKS LANDING BOULEVARD Palm Harbor , FL Located within the gated community of Hawks Landing, 2661 Hawks Landing Blvd offers a comb...	5 beds \| 4 baths \| 5,114 sq.ft.	$2,200,000	Airbnb cash on cash: -0.96% Traditional cash on cash: 3.51% Airbnb Rental Income: $2668 Traditional Rental Income: $11171 Airbnb ROI: -0.96% Traditional ROI: 3.51%
8345 SW 200TH COURT Dunnellon , FL Welcome to Your Half-Acre Florida Retreat! Set on a beautiful half-acre lot, this charmin...	2 beds \| 2 baths \| 1,249 sq.ft.	$315,000	Airbnb cash on cash: 4.53% Traditional cash on cash: 5.04% Airbnb Rental Income: $2729 Traditional Rental Income: $2237 Airbnb ROI: 4.53% Traditional ROI: 5.04%
7806 N VAN DYKE PLACE Tampa , FL Under contract-accepting backup offers. Qualified buyers gets 1% credit with preferred len...	3 beds \| 3 baths \| 1,604 sq.ft.	$350,000	Airbnb cash on cash: 0% Traditional cash on cash: 8.07% Airbnb Rental Income: $925 Traditional Rental Income: $3234 Airbnb ROI: 0% Traditional ROI: 8.07%
8419 N OLA AVENUE Tampa , FL Move-in ready and fully upgraded! This stunning Tampa home boasts a new roof and stylish u...	3 beds \| 2 baths \| 1,120 sq.ft.	$379,000	Airbnb cash on cash: 0.26% Traditional cash on cash: 6.25% Airbnb Rental Income: $991 Traditional Rental Income: $2767 Airbnb ROI: 0.26% Traditional ROI: 6.25%
7211 N TALIAFERRO AVENUE Tampa , FL Welcome to a truly special Seminole Heights bungalow where timeless character meets though...	3 beds \| 2 baths \| 1,090 sq.ft.	$390,000	Airbnb cash on cash: -1.19% Traditional cash on cash: 4.76% Airbnb Rental Income: $902 Traditional Rental Income: $2740 Airbnb ROI: -1.19% Traditional ROI: 4.76%
375 Plymouth Road West Palm Beach , FL Welcome to 375 Plymouth Road, a turnkey residence in West Palm Beachâs coveted SoSo neig...	3 beds \| 3 baths \| 1,967 sq.ft.	$2,265,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 1.01% Airbnb Rental Income: $1088 Traditional Rental Income: $4721 Airbnb ROI: -0.9% Traditional ROI: 1.01%
7308 Hager Way Orlando , FL 7308 Hager Way, Orlando, FL 32822 \| Single Family Residential	3 beds \| 1 baths \| 1,152 sq.ft.	$360,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 3.91% Airbnb Rental Income: $1099 Traditional Rental Income: $2050 Airbnb ROI: -0.01% Traditional ROI: 3.91%
155 S Court Ave #1013 Orlando , FL 155 S Court Ave #1013, Orlando, FL 32801 \| Condo/Coop	1 beds \| 1 baths \| 772 sq.ft.	$269,000	Airbnb cash on cash: -2.31% Traditional cash on cash: 0.28% Airbnb Rental Income: $1318 Traditional Rental Income: $1565 Airbnb ROI: -2.31% Traditional ROI: 0.28%
322 E Central Blvd #1205 Orlando , FL 322 E Central Blvd #1205, Orlando, FL 32801 \| Condo/Coop	2 beds \| 2 baths \| 1,150 sq.ft.	$419,000	Airbnb cash on cash: -1.69% Traditional cash on cash: -0.22% Airbnb Rental Income: $1680 Traditional Rental Income: $1786 Airbnb ROI: -1.69% Traditional ROI: -0.22%
150 E ROBINSON STREET #1612 Orlando , FL This Distinguished Condo speaks for itself! No expense was spared on the new finishes. Uni...	2 beds \| 2 baths \| 1,285 sq.ft.	$689,000	Airbnb cash on cash: -2.48% Traditional cash on cash: -0.46% Airbnb Rental Income: $1693 Traditional Rental Income: $2523 Airbnb ROI: -2.48% Traditional ROI: -0.46%
155 S Court Ave #1603 Orlando , FL 155 S Court Ave #1603, Orlando, FL 32801 \| Condo/Coop	1 beds \| 1 baths \| 615 sq.ft.	$205,000	Airbnb cash on cash: -1.36% Traditional cash on cash: 1.85% Airbnb Rental Income: $1318 Traditional Rental Income: $1535 Airbnb ROI: -1.36% Traditional ROI: 1.85%
300 E SOUTH STREET #6004 Orlando , FL Location, location, ...Charming one bedroom one bath on top 6th floor with Balcony overloo...	1 beds \| 1 baths \| 744 sq.ft.	$187,000	Airbnb cash on cash: -1.36% Traditional cash on cash: 3.62% Airbnb Rental Income: $1318 Traditional Rental Income: $1795 Airbnb ROI: -1.36% Traditional ROI: 3.62%
155 S Court Ave #2716 Orlando , FL 155 S Court Ave #2716, Orlando, FL 32801 \| Condo/Coop	2 beds \| 2 baths \| 1,212 sq.ft.	$427,000	Airbnb cash on cash: -2.81% Traditional cash on cash: -0.59% Airbnb Rental Income: $1680 Traditional Rental Income: $2099 Airbnb ROI: -2.81% Traditional ROI: -0.59%

Your search for investment property begins and ends here

Single Family Homes for Sale in San Mateo, FL

129 Divi Divi Dr

SAN MATEO, FL

3 beds | 3 baths | 3,189 sq.ft.

$529,000

Airbnb cash on cash: 3.3%

Traditional cash on cash: 4.09%

Airbnb Rental Income: $3571

Traditional Rental Income: $3177

Airbnb ROI: 3.3%

Traditional ROI: 4.09%

143 Pinecrest Circle

SAN MATEO, FL

4 beds | 3 baths | 3,876 sq.ft.

$524,900

Airbnb cash on cash: 5.49%

Traditional cash on cash: 4.49%

Airbnb Rental Income: $4441

Traditional Rental Income: $3022

Airbnb ROI: 5.49%

Traditional ROI: 4.49%

689 S HIGHWAY17

SAN MATEO, FL

3 beds | 2 baths | 1,668 sq.ft.

$650,000

Airbnb cash on cash: 2.9%

Traditional cash on cash: 2.51%

Airbnb Rental Income: $3571

Traditional Rental Income: $2548

Airbnb ROI: 2.9%

Traditional ROI: 2.51%

156 Crosby Rd

SAN MATEO, FL

4 beds | 3 baths | 3,233 sq.ft.

$549,900

Airbnb cash on cash: 4.77%

Traditional cash on cash: 6.35%

Airbnb Rental Income: $4441

Traditional Rental Income: $4324

Airbnb ROI: 4.77%

Traditional ROI: 6.35%

Other Single Family Residential Investment Properties for Sale in Florida

Panama City Beach , FL

3 beds | 3 baths | 1,565 sq.ft.

$777,000

Airbnb cash on cash: -1.81%

Traditional cash on cash: -0.08%

Airbnb Rental Income: $1279

Traditional Rental Income: $2128

Airbnb ROI: -1.81%

Traditional ROI: -0.08%

Tallahassee , FL

3 beds | 2 baths | 1,562 sq.ft.

$339,500

Airbnb cash on cash: -0.2%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $993

Traditional Rental Income: $1799

Airbnb ROI: -0.2%

Traditional ROI: 3.44%

Palm Harbor , FL

5 beds | 4 baths | 5,114 sq.ft.

$2,200,000

Airbnb cash on cash: -0.96%

Traditional cash on cash: 3.51%

Airbnb Rental Income: $2668

Traditional Rental Income: $11171

Airbnb ROI: -0.96%

Traditional ROI: 3.51%

Dunnellon , FL

2 beds | 2 baths | 1,249 sq.ft.

$315,000

Airbnb cash on cash: 4.53%

Traditional cash on cash: 5.04%

Airbnb Rental Income: $2729

Traditional Rental Income: $2237

Airbnb ROI: 4.53%

Traditional ROI: 5.04%

Tampa , FL

3 beds | 3 baths | 1,604 sq.ft.