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 Over $1,000,000
215 Prague St, SAN MATEO
  • Single Family Residential
  • 3 Beds
  • 2 Baths
  • 1,340 SqFt

215 Prague St, SAN MATEO

$1,268,000
932 Peninsula Ave 406, SAN MATEO
  • Condo / Townhome
  • 2 Beds
  • 1 Baths
  • 894 SqFt

932 Peninsula Ave 406, SAN MATEO

$699,000
222 8th Ave 216, SAN MATEO
  • Condo / Townhome
  • 2 Beds
  • 2 Baths
  • 1,202 SqFt

222 8th Ave 216, SAN MATEO

$1,198,000
437 Turner Ter, SAN MATEO
  • Single Family Residential
  • 4 Beds
  • 4 Baths
  • 2,430 SqFt

437 Turner Ter, SAN MATEO

$1,950,000
1504 York Ave, SAN MATEO
  • Single Family Residential
  • 3 Beds
  • 3 Baths
  • 1,650 SqFt

1504 York Ave, SAN MATEO

$1,688,000 ↑ $8,000
127 N Delaware St, SAN MATEO
  • Multi-Residential
  • 0 Beds
  • 0 Baths
  • 2,042 SqFt

127 N Delaware St, SAN MATEO

$1,600,000
133 N Delaware St, SAN MATEO
  • Multi-Residential
  • 0 Beds
  • 0 Baths
  • 2,042 SqFt

133 N Delaware St, SAN MATEO

$1,600,000
127 & 133 N Delaware St, SAN MATEO
  • Multi-Residential
  • 0 Beds
  • 0 Baths
  • 4,084 SqFt

127 & 133 N Delaware St, SAN MATEO

$3,200,000
847 Woodside Way 218, SAN MATEO
  • Condo / Townhome
  • 2 Beds
  • 1 Baths
  • 847 SqFt

847 Woodside Way 218, SAN MATEO

$595,000
177 N El Camino Real 34, SAN MATEO
  • Condo / Townhome
  • 1 Beds
  • 1 Baths
  • 710 SqFt

177 N El Camino Real 34, SAN MATEO

$500,000
1 Baldwin Ave 503, SAN MATEO
  • Condo / Townhome
  • 2 Beds
  • 2 Baths
  • 1,425 SqFt

1 Baldwin Ave 503, SAN MATEO

$695,000
211 Monte Diablo Ave, SAN MATEO
  • Single Family Residential
  • 3 Beds
  • 2 Baths
  • 1,290 SqFt

211 Monte Diablo Ave, SAN MATEO

$1,368,000

MLSListings Inc Logo Based on information from MLSListings MLS as of September 1st, 2025 at 5:42am 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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