$3,850,000 For sale

299 Maywood Drive

San Francisco, CA 94127

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Description

$3,850,000
299 Maywood Drive
San Francisco, CA 94127

Prominently presiding over an enclave of impressive homes, this rare Monterey Heights property delights the senses with its grandeur, architectural pedigree and spectacular views! As a stunning exemplar of Mediterranean revivalist architecture, this distinctive property combines Italian, Spanish & Colonial design influences. Quality materials and craftsmanship are hallmarks of this building era and are superbly displayed throughout this special home. Iconic arched windows, newer stucco siding, red clay tile roof and decorative wrought iron adorn the property’s exterior. Situated on a sizable lot, wrought iron trellises and a flourish of colorful flora merge with stone walkways & privacy hedges. Stunning period details throughout the interior imbue the home with authenticity. A dramatic two-story foyer with curved wrought iron railed staircase graces the entry. Grand spaces meet the eye from every direction – designed for expansive living and gracious entertainment. The elegant dining room adjoins a breakfast room and delightful sitting room bathed in natural light. A refreshed classic kitchen features custom designed Italian tile, newer stainless appliances and an eat-in nook. A spacious guest bedroom, perfectly separated from the public rooms, completes the main level of the home. The primary suite on the upper-level features two walk in closets, an ante room ideal as a nursery or quiet refuge, classic French doors & Juliette balconies which open to far-reaching vistas. A well-scaled second bedroom includes a private office/den area with breathtaking ocean views. The expansive lower level is comprised of a large family room with built-in bar, a flex room and finished storage room provide endless possibilities for re-imagination. Owned by the same family for 60 years, the recent and extensive capital improvements and structural upgrades of this extraordinary home provide an opportunity for its 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 access to 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 a welcoming atmosphere.

Listing Provided by:
Cece A. Doricko (DRE #01513516)
Compass
Cathy Truelove (DRE #01363591)
Compass
4/9/2026
Single Family Residence
299 Maywood Drive San Francisco, CA 94127
3
Bed
3
Bath
1
Parking
sqft
4,250
MLS#
426117107
Year built
1927
loft sqft
5771.7
DOM
5
price/sqft
$906
unit
N/A
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Location

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