299 Maywood Dr

• Sun Apr 12, 1:00 pm - 4:00 pm

  1st Sunday Open! Majestic Spanish Mediterranean with Spectacular Architectural Detail!

• Tue Apr 14, 1:00 pm - 3:00 pm

  Majestic Spanish Mediterranean with Spectacular Architectural Detail!

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.

Days on Market

1 day

Current Status

Active

Original Price

$3,850,000

List Price

$3,850,000

On Market Date

Apr 9, 2026

Property Type

Single Family Residence

District

4 - Monterey Heights

Zip Code

94127

MLS ID

426117107

APN

3045-009

Year Built

1927

Stories in Building

2

Possession

Close Of Escrow

Data Source

SFAR

Origin MLS System

Bed

3

Bath

2.5

Shower Stall(s), Tub, Tub w/Shower Over

Parking

1

Attached, Garage Door Opener, Interior Access, Private

SQ FT

4,250

SQ FT Source

Unavailable

Lot SQ FT

5,771.0

Lot Acres

0.1325 Acres

Kitchen

Breakfast Room, Pantry Closet, Tile Counter

Dining Room

Formal Room

Exterior Details

Wet Bar

Living Room

Open Beam Ceiling, Sunken, View

Flooring

Luxury Vinyl Plank, Tile, Wood

Fire Place

Wood Burning

Heating

Central

Laundry

Dryer Included, Washer Included

Upper Level

Bedroom(s), Full Bath(s), Primary Bedroom

Main Level

Bedroom(s), Dining Room, Full Bath(s), Kitchen, Living Room, Street Entrance

Views

City, Hills, Ocean

Possession

Close Of Escrow

Architectural Style

Mediterranean, Spanish

Special Listing Conditions

Trust

Fee

$27

Name

Monterey Heights HOA

MLS and other Information regarding properties for sale as shown in Theo have been obtained from various sources such as sellers, public records, agents and other third parties. This information may relate to the condition of the property, permitted or unpermitted uses, zoning, square footage, lot size/acreage or other matters affecting value or desirability. Unless otherwise indicated in writing, neither brokers, agents nor Theo have verified, or will verify, such information. If any such information is important to buyer in determining whether to buy, the price to pay or intended use of the property, buyer is urged to conduct their own investigation with qualified professionals, satisfy themselves with respect to that information, and to rely solely on the results of that investigation.

School data provided by GreatSchools. School service boundaries are intended to be used as reference only. To verify enrollment eligibility for a property, contact the school directly.