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5 Beds
3 Baths
2,730 sqft

$2,550,000

4314 Middlesex Drive, San Diego CA, 92116

Price per sqft$934.07
Built in1938
Property size2,730 sqft
Property typeResidential
test courtesy

Overview

Active

Listed Mar 11, 2026

Updated Apr 10

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.

$16,965/mo

Est. mortgage payment based on a $2,550,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
260005611SD

Interior Features

Bedrooms
5
Bathrooms
3

Exterior Features

Lot Size
0.21 Acres

Other Property Details

55+/Senior Community
No
MLS provider logo

Broker Reciprocity Courtesy of Keller Williams La Jolla, Patrick Mercer

Riff Rifferson - Full Name

- Phone Number

[email protected] - Email

- Brokerage Name

78108 - MLS License Number

 

Data last updated 6:15 AM UTC, 4/10/2026

 

Based on information from California Regional Multiple Listing Service, Inc. as of 4/10/2026. This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing.  Display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent.

 

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