Property Details
Property Details
Property Details
4314 Middlesex Drive, San Diego, CA 92116
$2,550,000 LOGIN TO SAVE
4314 Middlesex Drive, San Diego, CA 92116
Bedrooms: 5
Bathrooms: 3
Area: 2730 SqFt.
Description
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.
Features
Listing provided courtesy of Patrick Mercer of Keller Williams La Jolla. Last updated . Listing information © 2025 Sandicor.
Work with Us
Under the Compass brand, Ramon and his team take great pride in having the ability to utilize today's cutting edge technology, marketing resources, and local and global connections to perfectly unite extraordinary places with the extraordinary buyers who will cherish them as we do.
Contact Us
North County Office
12275 El Camino Real, Suite 100
San Diego, CA 92130
858.345.4514
La Jolla Office
7863 Girard Avenue, Suite 208
La Jolla, CA, 92037
858.277.3325
San Diego Office
655 W Broadway
San Diego, CA 92101
619.317.1875

This information is deemed reliable but not guaranteed. You should rely on this information only to decide whether or not to further investigate a particular property. BEFORE MAKING ANY OTHER DECISION, YOU SHOULD PERSONALLY INVESTIGATE THE FACTS (e.g. square footage and lot size) with the assistance of an appropriate professional. You may use this information only to identify properties you may be interested in investigating further. All uses except for personal, non-commercial use in accordance with the foregoing purpose are prohibited. Redistribution or copying of this information, any photographs or video tours is strictly prohibited. This information is derived from the Internet Data Exchange (IDX) service provided by Sandicor®. Displayed property listings may be held by a brokerage firm other than the broker and/or agent responsible for this display. The information and any photographs and video tours and the compilation from which they are derived is protected by copyright. Compilation © 2025 Sandicor®, Inc.
Copyright © 2025 Maldonado Team. All Rights Reserved.
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This information is deemed reliable but not guaranteed. You should rely on this information only to decide whether or not to further investigate a particular property. BEFORE MAKING ANY OTHER DECISION, YOU SHOULD PERSONALLY INVESTIGATE THE FACTS (e.g. square footage and lot size) with the assistance of an appropriate professional. You may use this information only to identify properties you may be interested in investigating further. All uses except for personal, non-commercial use in accordance with the foregoing purpose are prohibited. Redistribution or copying of this information, any photographs or video tours is strictly prohibited. This information is derived from the Internet Data Exchange (IDX) service provided by Sandicor®. Displayed property listings may be held by a brokerage firm other than the broker and/or agent responsible for this display. The information and any photographs and video tours and the compilation from which they are derived is protected by copyright. Compilation © 2025 Sandicor®, Inc.
Copyright © 2025 Maldonado Team. All Rights Reserved.
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