$2,550,000

4314 Middlesex Drive, San Diego, CA 92116

5 beds |
3 baths |
2,730 sqft

Single-Family Home
Built in 1938
9,148sqft lot
2 car garage
$934/sqft
Listed 22 days ago

Property 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.

Listing Status:: Active
Date Added:: March 10, 2026
Data Last Updated:: April 1, 2026 at 7:11PM
Listing Office:: Keller Williams La Jolla : 858-457-9400
Listing Agent:: Patrick H Mercer : 619-846-2083
MLS ID:: 260005611

Appliances: DishwasherDisposalFree Standing RangeGarage Door OpenerGas CookingGas OvenGas RangeGas StoveMicrowavePool/Spa/EquipmentRange/OvenRefrigeratorSolar PanelsWasher
Laundry: ElectricGas
A/C: Central Forced Air
Heating: Forced Air UnitNatural Gas
Fireplace: FP in Living RoomFireplaces: 1

Pool: Below Ground
Parking: AttachedParking spaces: 4

Roofing: Composition
General: Stucco2 Story

HOA Amenities: 0.0
Originating MLS: SDMLS
County: San Diego

Zoning: 465-041-08-00
View: Evening LightsMountains/HillsValley/Canyon
Fencing: Full
Restrictions: None Known

Water: Meter on Property
Sewer: Sewer Connected

Source: SDMLS

This listing courtesy of Patrick H Mercer , Keller Williams La Jolla

Monthly Payment

$Est. Payment

Principal & Interest $
Property Taxes $
Home Insurance $
VA Funding Fee $

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Location

Schools Nearby

Franklin Elementary School

4481 Copeland Ave, San Diego, CA, 92116

Grades KG-5

0.95 miles away

Wilson Middle School

3838 Orange Ave, San Diego, CA, 92105

Grades 6-8

1.36 miles away

Hoover High School

4474 El Cajon Blvd, San Diego, CA, 92115

Grades 9-12

1.13 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.