The Boyenga Team | Silicon Valley REALTORS®

San Mateo Real Estate

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came to San Mateo in 1849. De Peyster created what would be the first business enterprise in San Mateo when he opened a stagecoach stop in the now abandoned mission outpost. By opening this business, de Peyster established what would be the main road through San Mateo. In May 1861, under the direction of Charles B. Polhemus, the construction of a railroad to link San Francisco with San Jose began. The track was completed in January 1864 and the first service through San Mateo was on October 17, 1863. The train made the trip from San Francisco to San Mateo in thirty-seven minutes. With Polhemus in the role of director of railroad construction, the decision about where the central business district would be located lay in his hands. The first building to be erected near the tracks was the train station, but it wasn't long before buildings began springing up in the area of Main Street and Railroad Avenue. This was the beginning of downtown San Mateo. The opening of railroad service in San Mateo attracted many wealthy San Franciscans to the area. San Mateo became an ideal place for building summer and weekend homes for people who worked in San Francisco. These estates were built for some of the most powerful people in the West. The resulting population that developed in San Mateo was largely made up of people employed in the service of these great mansions. During this period, the wealthy estate owners bought up large parcels of land, keeping the majority of San Mateo property owned by a few families. During this period, there were some families that established their own wealth through enterprises in the area. One of the most successful of these businesses was the building company owned by the Wisnom family. Robert Wisnom became the best known builder during this era and he is credited for erecting many buildings in San Mateo.

San Mateo Homes for Sale

All Listings $500,000 - $600,000 $600,000 - $700,000
$700,000 - $800,000 $800,000 - $900,000 $900,000 - $1,000,000
Over $1,000,000
New
409 Tilton Ave, SAN MATEO
  • Single Family Residential
  • 5 Beds
  • 3 Baths
  • 1,647 SqFt

409 Tilton Ave, SAN MATEO

$1,290,000
New
1639 Cypress Ave, San Mateo
  • Single Family Residential
  • 3 Beds
  • 2 Baths
  • 1,140 SqFt

1639 Cypress Ave, San Mateo

$1,499,000
New
996 Patricia Ave, San Mateo
  • Single Family Residential
  • 3 Beds
  • 2 Baths
  • 1,395 SqFt

996 Patricia Ave, San Mateo

$1,649,000
New
819 N Humboldt St 407, SAN MATEO
  • Condo / Townhome
  • 1 Beds
  • 1 Baths
  • 693 SqFt

819 N Humboldt St 407, SAN MATEO

$540,000
New
934 Peninsula Ave 411, SAN MATEO
  • Condo / Townhome
  • 1 Beds
  • 1 Baths
  • 693 SqFt

934 Peninsula Ave 411, SAN MATEO

$540,000
New
239 Prague St, SAN MATEO
  • Single Family Residential
  • 3 Beds
  • 2 Baths
  • 1,740 SqFt

239 Prague St, SAN MATEO

$1,548,000
316 N El Camino Real 217, SAN MATEO
  • Condo / Townhome
  • 2 Beds
  • 2 Baths
  • 990 SqFt

316 N El Camino Real 217, SAN MATEO

$785,000
1537 Cypress Ave, SAN MATEO
  • Single Family Residential
  • 4 Beds
  • 2 Baths
  • 1,440 SqFt

1537 Cypress Ave, SAN MATEO

$999,000
709 S B St, SAN MATEO
  • Common Interest
  • 0 Beds
  • 0 Baths
  • 5,005 SqFt

709 S B St, SAN MATEO

$2,200,000
871 Woodside Way, SAN MATEO
  • Multi-Residential
  • 0 Beds
  • 0 Baths
  • 2,242 SqFt

871 Woodside Way, SAN MATEO

$1,880,000
800 N Delaware St 310, SAN MATEO
  • Condo / Townhome
  • 1 Beds
  • 1 Baths
  • 693 SqFt

800 N Delaware St 310, SAN MATEO

$548,000 ↓ $40,000
115 N Kingston St, SAN MATEO
  • Multi-Residential
  • 0 Beds
  • 0 Baths
  • 1,960 SqFt

115 N Kingston St, SAN MATEO

$1,398,000 ↓ $40,888

MLSListings Inc Logo Based on information from MLSListings MLS as of March 20th, 2026 at 4:40am PDT.
All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS.
All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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