
San Francisco, CA 94127
This Grand Monterey Heights Estate is a Strong Value Opportunity, listed at $3,850,000—positioned well below the $4,086,377 Fair Market Value by 5%. This valuation gap provides $236,377 in Instant Equity for a residence in Move-in Ready Condition. Boasting breathtaking ocean views and 4,250 sqft of architectural pedigree, the home offers massive upside via a lower-level ADU conversion. Proximity to Lowell High School (10/10) and Chinese Immersion School (9/10) ensures long-term asset stability. This is a premier acquisition for Owner-Occupants seeking a legacy home or Luxury-Focused Investors looking for significant value-add potential.
Comparables within 1 miles sold in recently
| Address | Sold Price | Beds | Baths | Sq Ft | $/Sqft | Distance |
|---|---|---|---|---|---|---|
★ 299 Maywood Drive Subject | $3,850,000* List Price | 3 | 3 | 4,250 | $962 | - |
A 1475 Monterey Boulevard Sold | $3,500,000 | 4 | 5 | 3,435 | $1,019 | 0.2 mi |
B 850 Darien Way Sold | $2,950,000 | 5 | 6 | 4,105 | $719 | 0.2 mi |
C 154 Maywood Drive Sold | $3,706,000 | 5 | 3 | 3,811 | $972 | 0.2 mi |
D 130 San Pablo Avenue Sold | $3,750,000 | 4 | 3 | 3,460 | $1,084 | 0.4 mi |
E 1185 Monterey Boulevard Active | $3,725,000 List Price | 5 | 3 | 3,210 | $1,160 | 0.1 mi |
* Subject property listed price vs sold prices of comps.
Property is move-in ready.
This 1927 property is in move-in ready condition, benefiting from recent extensive capital improvements and structural upgrades. The kitchen has been refreshed with high-end stainless steel appliances (Wolf and Sub-Zero) and custom Italian tile. The interior features well-maintained architectural details, including pristine herringbone hardwood floors, dark wood trim, and original arched windows. While some bathrooms retain a vintage aesthetic and the kitchen cabinetry follows a more traditional 'refreshed' style rather than a full modern gut-renovation, the overall quality, scale, and maintenance of the home are exceptional for its age.
Elementary School: Chinese Immersion School At Deavila (9/10). Middle School: Lilienthal (Claire) Elementary School (9/10). High School: Lowell High School (10/10).
This 4,250 sqft 1927 estate features a dramatic two-story foyer and high-quality craftsmanship, offering a level of grandeur and expansive living space rarely found in San Francisco.
The property boasts spectacular, unobstructed ocean views from the primary suite and upper-level offices, significantly enhancing its luxury appeal and market value.
Despite the massive square footage, the upper level is currently configured as only two oversized bedrooms, which may require the buyer to undertake a costly reconfiguration to meet standard family needs.
At a $3.85M price point, the property represents a significant investment that likely requires additional capital for modernization to fully align its 1920s interiors with contemporary luxury standards.
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.
No exterior & parking available.
Grades K-5 • 0.5 mi
Grades K-5 • 0.7 mi
Grades K-5 • 0.8 mi
No sensitive facilities data found.
| Feature | Subject | Average Home | Neighborhood Ranking (50 Listings) |
|---|---|---|---|
| Beds | 3.0 | 4.0 | 45% |
| Baths | 3.0 | 3.0 | 50% |
| Square foot | 4,250 | 2,298 | 95% |
| Lot Size | 5,772 | 3,831.103 | 88% |
| Price | $3.85M | $2.44M | 89% |
| Price per sq ft | $906 | $1.1K | 18% |
| Built year | 1927 | 1929 | 39% |
| HOA | $27 | $0 | 83% |
| Days on market | 21 | 169 | 2% |
Apr 1, 2026
$3,850,000
Initial Listing
Dec 29, 1995
$1,350,000
Public Record