
San Diego, California 92116
This Stunning Colonial Revival Residence is a Prime Investment Opportunity listed at $2,550,000—positioned well below the $2,603,859 Fair Market Value by 2%. This valuation gap offers $53,859 in Instant Equity. Boasting a Move-In Ready Condition Rating, the home features sweeping canyon views, an elegant pool, and premium upgrades including fully paid solar with Tesla batteries. Located near top-rated Lewis Middle and Patrick Henry High, this iconic estate offers a rare blend of historic charm and modern efficiency. It is an ideal acquisition for lifestyle-oriented professionals or growing families seeking a prestigious San Diego sanctuary.
Comparables within 1 miles sold in recently
| Address | Sold Price | Beds | Baths | Sq Ft | $/Sqft | Distance |
|---|---|---|---|---|---|---|
★ 4314 Middlesex Drive Subject | $2,550,000* List Price | 5 | 3 | 2,730 | $954 | - |
A 4010 S Hempstead Circle Sold | $2,269,733 | 5 | 4 | 2,809 | $808 | 0.5 mi |
B 4965 Marlborough Drive Sold | $1,810,000 | 3 | 2 | 1,815 | $997 | 0.4 mi |
C 4736 38 Kensington Drive Pending | $2,250,000 List Price | 4 | 4 | 2,300 | $978 | 0.6 mi |
* Subject property listed price vs sold prices of comps.
Property is move-in ready.
The property is in move-in ready condition and has been exceptionally well-maintained. While originally built in 1938, it features major recent system upgrades including a brand new roof, fully paid solar, and Tesla backup batteries. The interior boasts classic hardwood flooring and elegant architectural details. The kitchen and bathrooms are clean and functional with updated stainless steel appliances, though they retain some older styling elements like tile countertops and traditional vanities that prevent an 'excellent' rating.
Situated on one of Kensington's most iconic and sought-after streets, this property offers rare, sweeping canyon views and exceptional privacy.
The home features significant high-value upgrades, including a brand-new roof, fully paid solar, and two Tesla backup batteries, providing modern efficiency in a classic residence.
The backyard serves as a private retreat with an elegant pool and professional landscaping by a renowned architect, perfectly designed for high-end entertaining.
Bedroom count discrepancy between mls listing and other public or private record. mls listing bedroom count = 5, other record bedroom count = 6.
Built in 1938, the property may require specialized ongoing maintenance or further updates to legacy systems typical of homes from this era.
The assigned elementary school has a lower rating (4/10) compared to the highly-rated middle and high schools in the district, which may be a concern for families with young children.
Set on one of the most prominent and sought-after streets in all of Kensington, this stunning Colonial Revival residence offers timeless architecture, sweeping canyon views, and an incredible sense of privacy. A Mediterranean-inspired courtyard welcomes you at the front of the home, creating a warm and inviting entry — the perfect setting for morning coffee or gathering with friends before heading out to enjoy the neighborhood. Inside, the home features a tremendous layout thoughtfully designed to maximize both comfort and views. One of the most striking spaces is the formal step-down living room, beautifully framed by a fireplace and two bifold windows that perfectly capture the canyon and courtyard views beyond. Natural light fills the home, while large windows throughout frame picturesque outlooks from many of the main living spaces and bedrooms. The floor plan flows effortlessly, offering a seamless balance of everyday livability and ideal spaces for entertaining. The backyard lives like a private retreat, complete with an elegant pool, generous outdoor living areas, and breathtaking canyon views that create a peaceful backdrop for relaxing or entertaining. The home has recently undergone a thoughtful transformation including a brand new roof, fully paid solar, two Tesla backup batteries, and new landscaping designed by a well-known local landscape architect. Located in highly desirable North Kensington just moments from Kensington Village and Adams Avenue, this is a rare opportunity to own a canyon-view home on one of the neighborhood’s most iconic streets.
No exterior & parking available.
Grades K-5 • 1.0 mi
Grades 6-8 • 1.4 mi
Grades 6-8 • 2.1 mi
No sensitive facilities data found.
| Feature | Subject | Average Home | Neighborhood Ranking (50 Listings) |
|---|---|---|---|
| Beds | 5.0 | 3.0 | 91% |
| Baths | 3.0 | 2.0 | 69% |
| Square foot | 2,730 | 1,515 | 91% |
| Lot Size | 8,982 | 5,251 | 82% |
| Price | $2.55M | $1.38M | 94% |
| Price per sq ft | $934 | $973 | 46% |
| Built year | 1938 | 1931 | 61% |
| HOA | $0 | $0 | 50% |
| Days on market | 42 | 158 | 13% |
Mar 11, 2026
$2,550,000
Initial Listing
Jul 14, 1999
$529,000
Public Record