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About This Home

This 5-bedroom, 3-bathroom single family at 4314 Middlesex Drive in San Diego, CA is listed for $2,550,000 ($934 per sqft). Built in 1938, the home offers 2,730 sqft of living space on a 0.21 acres lot.

Agent 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.

Key Features

  • Built in 1938
  • 0.21 acre lot
  • 2 stories
  • 4 parking spaces
  • Fireplace

Property Details

2 stories
3 full
4 spaces
1938

Amenities

FireplaceViewA/C

Monthly Cost Estimate

$13,638/mo

20% down · 6.5% · 30 years

Principal$1,844
Interest$11,050
Insurance$744

Estimates only. Actual payments may vary.

Location

4314 Middlesex Drive

San Diego, CA 92116

KENSINGTON

Property Details

Views

HillsCanyon

Heating

Forced Air

Cooling

Central Air

Appliances

DishwasherDisposalGarage Door OpenerMicrowavePool/Spa/EquipmentRange/OvenRefrigeratorSolar PanelsWasherFree Standing RangeGas OvenGas StoveGas RangeGas Cooking

Questions & Answers

This 5-bedroom, 3-bathroom single family at 4314 Middlesex Drive is listed at $2,550,000 ($934/sqft). The estimated monthly payment is $11,050 based on 20% down at 6.5% interest.

Key features include: Built in 1938, 0.21 acre lot, 2 stories, 4 parking spaces, Fireplace.

This property is listed by Patrick H Mercer and can be reached at 6198462083 or Patrick@Mercergrouprealestate.com.

PM

Patrick H Mercer

Agent at Keller Williams La Jolla

(619) 846-2083

Listed by Keller Williams La Jolla

MLS# 260005611· Source: listhub· Updated 31 days ago

Copyright © 2026 San Diego MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

4314 Middlesex Drive, San Diego, CA 92116

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