299 Maywood Drive, San Francisco, CA 94127

$4,000,000
3
BD
3
BA
4,250
SqFt

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Sold Price
$4,000,000
List Price
$3,850,000
Days on Market
89
Closing Date
Jun 29, 2026
MLS#
426117107
Building / Subdivision
Monterey Heights
Bedrooms
3
Bathrooms
3
Living Sq. Ft
4,250
Lot Size
5,771
Type
Single Family Residential
Zip
94127
City
San Francisco

Property Description

Prominently presiding over an enclave of impressive homes, this rare Monterey Heights property delights the senses with its grandeur, architectural pedigree and spectacular views! The incredible scale of the home offers the new owner an opportunity to reconfigure to meet their specific lifestyle needs. Quality materials and craftsmanship are hallmarks of this building era and are superbly displayed throughout the home. Situated on a sizable lot, wrought iron trellises and a flourish of colorful flora merge with stone walkways & privacy hedges. Designed for expansive living and gracious entertainment, a dramatic two-story foyer with curved wrought iron railed staircase graces the entry. The elegant dining room adjoins a peaceful den/office bathed in natural light. The refreshed classic eat-in kitchen features custom designed Italian tile, newer stainless appliances and a sunny breakfast room for casual dining. A spacious guest bedroom and hall bath, perfectly separated from the public rooms, completes the main level. Measuring at over 1,600sqft, the private upper level and was originally designed for 3 sizable bedrooms but is currently configured as 2 oversized bedrooms w/offices, with the opportunity to reconfigure these rooms, as needed. The grand primary suite features two walk in closets, Juliette balconies and a large adjoining room, ideal as an office or nursery with breathtaking ocean views. A well-scaled second bedroom also features a private office/den area with more ocean views! The expansive lower level is comprised of a casual family room with built-in bar. This level also includes a laundry room, 1/2 bath and several add'l rooms that could be utilized as a home gym, private office space and/or for sporting goods storage. This level has endless development possibilities such as an in-law, ADU or another primary suite. Owned by the same family for 60 years, the recent and extensive capital improvements and structural upgrades create the backdrop for the next stewards to begin their own legacy. Monterey Heights is a serene residential neighborhood known for its tree-lined streets and breathtaking hillside and ocean views. Residents enjoy nearby hiking trails and the wonderful shops and cafes of the popular West Portal shopping corridor. With a quick commute to SFO, Monterey Heights provides the perfect blend of convenience, natural beauty, and community.

Additional Information

View
City, Hills, Ocean
Possession
Close Of Escrow
Fireplaces
Wood Burning
Neighborhood
Monterey Heights
Heating
Central
Year Built
1927
Acres
0.13
Garage Spaces
1
Hoa
Yes
Style
Mediterranean, Spanish
Parking Spaces
1
Stories
2

Mortgage Calculator

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Calculator source: Real Geeks

Listing courtesy of Cece Doricko from Compass.

Selling Office: Engel & Voelkers Mill Valley.