4314 Middlesex Drive
San Diego, CA 92116 • 5 Bed • 3 Bath • 2,730 sq.ft.

Property summary

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.

Days on market: 1

Listing updated: March 11, 2026 - 11:01:03

Property details

Property ID
260005611SD
Size
2730 sq.ft.
Home Type
Residential
Year Built
1938
Property Size
0.2062 acre
Garage
2
Levels
2
Spa
No
Patio
No
Basement
No
View
Mountain(s)
Pool
In Ground

Listed by: Patrick Mercer DRE #01964971 858-457-9400, Keller Williams La Jolla - San Diego

Source: San Diego, MLS#: SAND-69375 Originating MLS: CRMLS

Interior information

Rooms
Bonus Room, Bedroom, Entry/Foyer, Exercise Room, Family Room, Kitchen, Laundry, Living Room, Primary Bathroom, Primary Bedroom, Other, Dining Room
Bathrooms
3
Kitchen
Dishwasher, Free-Standing Range, Gas Cooking, Gas Cooktop, Disposal, Gas Oven, Gas Range, Microwave, Refrigerator
Cooling
Central Air
Heating
Forced Air, Natural Gas
Flooring
N/A
Laundry
Electric Dryer Hookup, Gas Dryer Hookup, Laundry Room
$2,550,000
Property price
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Revesty savings: $87K
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Est.: $10,200/mo
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Working hours: Monday to Friday 9:00am - 6:00pm (PST)

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The multiple listing data appearing on this website, or contained in reports produced therefrom, is owned and copyrighted by California Regional Multiple Listing Service, Inc. ("CRMLS") and is protected by all applicable copyright laws. Information provided is for viewer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the viewer may be interested in purchasing. All listing data, including but not limited to square footage and lot size is believed to be accurate, but the listing Agent, listing Broker and CRMLS and its affiliates do not warrant or guarantee such accuracy. The viewer should independently verify the listed data prior to making any decisions based on such information by personal inspection and/or contacting a real estate professional. Based on information from California Regional Multiple Listing Service, Inc. as of 2026-03-15 16:24:52 PST and /or other sources. All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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