299 Maywood Drive
$4,000,000

299 Maywood Drive

3 Beds 3 Baths 4,250 Sq.Ft. 5,771.7 Sq.Ft.

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.

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Location

299 Maywood Drive, San Francisco, CA 94127

Status

Sold

Date Sold

June 29, 2026

Property Amenities

Interior
Fireplace Wood Burning
Appliances Dishwasher, Disposal, Free-Standing Gas Range, Free-Standing Refrigerator, Dryer, Washer
Flooring Luxury Vinyl Plank, Tile, Wood
Total Bedrooms: 3
Half Bathrooms: 1
Full Bathrooms: 2
Other Interior Features Cathedral Ceiling(s), Formal Entry, Storage, Wet Bar
Area & Lot
Total area 4,250 Sq.Ft.
Lot Area 5,771.7 Sq.Ft.
Living area 4,250 Sq.Ft.
MLS® ID 426117107
Year Built 1927
View Description City,Hills,Ocean
Architecture Styles Mediterranean, Spanish
Type Residential
Status Sold
Exterior
Stories 2
Heat type Central
Water Source Public
Garage Space 1.0
Sewer Public Sewer
Other Exterior Features Wet Bar
Parking Attached, Garage Door Opener, Inside Entrance, Private, Independent, On Site (Single Family Only)
Lot Features Corner Lot, Landscape Front
Utilities Public
Finance
Sales Price $4,000,000
HOA Fees $27 yearly

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