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$2,550,000
2 Days On Site

4314 Middlesex Drive
San Diego, CA 92116

For Sale|Single Family Residence|Active
5
Beds
3
Total Baths
3
Full Baths
2,730
SqFt
$934
/SqFt
1938
Built
Subdivision:
KENSINGTON
County:
San Diego
Listed by Patrick H Mercer of Keller Williams La Jolla (619) 846-2083

Due to the health concerns created by Coronavirus we are offering personal 1-1 online video walkthough tours where possible.

Upcoming Open Houses
Due to COVID-19, we recommend you verify Open Houses before attending.
Sat, Mar 14, 12:00 PM - 2:00 PM
Sun, Mar 15, 2:00 PM - 4:00 PM
4314 Middlesex Drive4314 Middlesex Drive4314 Middlesex Drive4314 Middlesex Drive
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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.

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Listing Snapshot
Price 
$2,550,000
Days On Site 
2 Days
Bedrooms 
5
Inside Area (SqFt) 
2,730 sqft
Total Baths 
3
Full Baths 
3
Partial Baths 
N/A
Lot Size 
N/A
Year Built 
1938
MLS® Number 
260005611
Status 
Active
Property Tax 
N/A
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
4 hours agoListing updated with changes from the MLS®
2 days agoListing first seen on site
General Features
Attached Garage 
Yes
Energy Features 
Solar
Garage 
Yes
Garage Spaces 
2
Number Of Stories 
2
Parking 
Garage Door OpenerAttached
Parking Spaces 
4
Property Sub Type 
Single Family Residence
SqFt Total 
2730
Utilities 
Sewer Connected
Interior Features
Appliances 
DishwasherDisposalFree-Standing RangeGas OvenGas RangeMicrowaveRefrigeratorWasherGas CooktopRangeOven
Cooling 
Central Air
Fireplace 
Yes
Fireplace Features 
Living Room
Fireplaces 
1
Heating 
Forced AirNatural Gas
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Exterior Features
Construction Details 
Stucco
Fencing 
Full
Pool Features 
In Ground
Roof 
Composition
View 
Mountain(s)Valley
Waterview 
Mountain(s)Valley
Community Features
Financing Terms Available 
CashConventionalVA Loan
MLS Area 
Metro Uptown
Listed by Patrick H Mercer of Keller Williams La Jolla (619) 846-2083



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 San Diego MLS®. 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. Copyright © 2026 San Diego MLS®.

Last checked 2026

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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