299 Maywood Drive, San Francisco, CA 94127

$3,850,000

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… Read More 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. Read Less

Courtesy of Cece Doricko, Compass, .

Listing Snapshot

Days Online

Last Updated

May 28, 2026

Property Type

Single Family

Beds

Full Baths

Partial Baths

Square Ft.

4,250

Lot Size

0.13 Acres

Year Built

1927

MLS Number

426117107

30 Days Snapshot Of 94127

$3.54M

+26%

(avg) sold price

-33%

homes sold

+42%

(avg) days on market

Snapshot

Area Map

Additional Details

Appliances & Equipment

"Dishwasher", "Disposal", "Free-Standing Gas Range", "Free-Standing Refrigerator", "Dryer", "Washer"

Building

Built in 1927, Living area: 4,250, Architectural style: "Mediterranean", "Spanish", Construction materials: "Stucco", 2 stories

Dining Room

Dining room level: Main, Dining room features: "Formal Room"

Exterior Features

"Wet Bar"

Fireplaces

"Wood Burning"

Family Room

Level: Lower

Garage

1 space

Heating

"Central"

Home Owner's Association

Association fee: $27

Interior Features

"Cathedral Ceiling(s)", "Formal Entry", "Storage", "Wet Bar"

Kitchen

Level: Main

Lot

0.1325 acres, 5,772 square feet, "Corner Lot", "Landscape Front"

Living Room

Level: Main

Parking

1 covered space, 1 total parking, "Attached", "Garage Door Opener", "Inside Entrance", "Private", "Independent", "On Site (Single Family Only)"

Property

Patio and porch features: "Front Porch", "Uncovered Patio"

Sewer

"Public Sewer"

Utilities

"Public"

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