This mid-century modern Joseph Eichler home has been masterfully renovated while preserving & enhancing what Eichler called boldness, change, and optimism through indoor/outdoor living. The clean-lined & flowing floor plan showcases signatures of the original Eichler design with slightly vaulted and paneled ceilings, white globe pendant lights, radiant-heated floors, and floor-to-ceiling walls of glass. New white oak floors unify every room with updated stylish elegance. Reimagined with an open concept and expanded for even more natural light, both the main living area and the primary suite seamlessly connect with the outdoors. The kitchen is sleek and modern, there are 3 total bedrooms, and the garage has been fully finished offering options for play and/or fitness space if needed. Perfectly located in the sought-after Highlands neighborhood, this premier location is just blocks to both the elementary school and the recreation center with pool, tennis, and playground. Welcome home!
Single-familyProperty Type
1956Year Built
7,171 sq ftLot Size
$1,976Est. Price/Sq.Ft.
2 car garageParking
Listed by Sternsmith Sternsmith Group•DRE #70016718• Compass
Contact: 650-678-5455
Bought with Catherine Gortner•DRE #01370537• Catherine Gortner Properties
First time on market! Lovingly owned and maintained by the same family for over 60 years. Classic San Mateo Highlands Eichler. Stunning Mid Century modern details of post and beam construction, tongue/groove ceiling. This home features a seperate living room with fireplace, a wall of glass that leads to patio for entertaining, large kitchen with adjacent eat-in area and family room, Master en-suite and two extra bedrooms that share a hall bath. Home has new exterior/interior paint and new carpet throughout. Ideal location, walk to the Rec center for swimming, tennis, playground, community programs, and located right down the street from the Highlands elementary school. Easy access to Hwys 92, 280 and SFO! Trust Sale, Property to be sold As-Is. No preemptive offers.
Year
Property tax
Land + Additions
Assessment*
2025
$31,471 (+7.3%)
$2,031,500 + $568,500
$2,600,000
2024
$29,334 (+18.4%)
$2,031,500 + $568,500
$2,600,000
2023
$24,779 (−2.2%)
$2,455,344 + $686,664
$3,142,008
2022
$25,333 (+1.7%)
$1,560,000 + $440,000
$2,000,000
2021
$24,918 (+3.4%)
$1,929,963 + $114,724
$2,044,687
2020
$24,090 (+2.6%)
$1,892,121 + $112,475
$2,004,596
2019
$23,477 (+701.5%)
$1,872,720 + $111,322
$1,984,042
2018
$2,929 (+2.9%)
$1,836,000 + $109,140
$1,945,140
2017
$2,847 (−5.6%)
$27,448 + $88,593
$116,041
2016
$3,015 (+4.0%)
$27,448 + $88,593
$116,041
2015
$2,898 (+1.4%)
$26,910 + $86,856
$113,766
2014
$2,858 (+0.8%)
$25,987 + $83,877
$109,864
2012
$2,836 (+6.8%)
$25,870 + $83,498
$109,368
2011
$2,656 (+0.8%)
$25,363 + $81,861
$107,224
2010
$2,637 (+14.4%)
$24,866 + $80,256
$105,122
2009
$2,304 (+5.8%)
$24,681 + $79,657
$104,338
2008
$2,177
$24,740 + $79,847
$104,587
Tax history for 1744 Monticello Rd
Year
Property tax
Land + Additions
Assessment*
2025
$31,471 (+7.3%)
$2,031,500 + $568,500
$2,600,000
2024
$29,334 (+18.4%)
$2,031,500 + $568,500
$2,600,000
2023
$24,779 (−2.2%)
$2,455,344 + $686,664
$3,142,008
2022
$25,333 (+1.7%)
$1,560,000 + $440,000
$2,000,000
2021
$24,918 (+3.4%)
$1,929,963 + $114,724
$2,044,687
2020
$24,090 (+2.6%)
$1,892,121 + $112,475
$2,004,596
2019
$23,477 (+701.5%)
$1,872,720 + $111,322
$1,984,042
2018
$2,929 (+2.9%)
$1,836,000 + $109,140
$1,945,140
2017
$2,847 (−5.6%)
$27,448 + $88,593
$116,041
2016
$3,015 (+4.0%)
$27,448 + $88,593
$116,041
2015
$2,898 (+1.4%)
$26,910 + $86,856
$113,766
2014
$2,858 (+0.8%)
$25,987 + $83,877
$109,864
2012
$2,836 (+6.8%)
$25,870 + $83,498
$109,368
2011
$2,656 (+0.8%)
$25,363 + $81,861
$107,224
2010
$2,637 (+14.4%)
$24,866 + $80,256
$105,122
2009
$2,304 (+5.8%)
$24,681 + $79,657
$104,338
2008
$2,177
$24,740 + $79,847
$104,587
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Public record
Permits
Beds
3
Baths
2
Stories
1
Lot width
—
Lot depth
—
Lot size
7,531 Sq. Ft.
Year renovated
1956
Sq. Ft.
1,440
Year built
1956
Style
Single Family Residential
County
San Mateo County
APN
041083060
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Sep 2, 2026.
Dec 6, 2013 • Final
Building
Remove and replace a sliding door in the living room.
Remodel
Dec 6, 2013 • Final
Building
Overlay one layer of tar and gravel with a foam roofing system.
Roofing
Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.
Property details
Parking
Parking Information
Garage (Minimum): 2
Garage (Maximum): 2
Parking Description: Attached Garage
Garage Spaces: 2
Interior
Virtual Tour
Bedroom Information
# of Bedrooms (Minimum): 3
# of Bedrooms (Maximum): 3
Bedrooms: Primary Suite/Retreat
Bathroom Information
# of Baths (Full): 2
Bathroom Description: 2+ Showers Over Tubs, Skylight, Tile, Tub in Master Bedroom
Room Information
Dining Room Description: Breakfast Bar, Dining Area, Skylight(s)