299 Maywood Drive

San Francisco CA 94127

4250 sq. ft.

5771.7 sq. ft.

Single-Family

Last sold for $4,000,000

Cece Doricko, last sold this property on 29 June 2026 after 80 days on market.

Overview

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.

Features

3 bedrooms

3 bathrooms

1 carspace

1 garage space

4250 sq. ft. floor area

5771.7 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in San Francisco over the last 12 months, the estimated median property value of 299 Maywood Drive is $2.11m.

Median value

$2.11m

Estimated value range

$1m - $4.31m

Median days on market

Estimated value trend

10%

increase over the last 12 months

Average days on market is based on recent, comparable sales in San Francisco. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 299 Maywood Drive

2026

Sold

$4,000,000

29 Jun 2026 by Cece Doricko, of Compass

Happy sellers in San Francisco

We have insufficient information to provide an overview of customer satisfaction for San Francisco. Viewing the agent profiles, reviews and sales for San Francisco can provide insights for this location.