For Sale at Kensington: 4314 Middlesex Drive, San Diego, CA 92116. 5-bedroom 3-bath, 2730 sf, 1938 Kensington $2,550,000 begin new search
Click a button below to contact Buyers' Agent from Compass. Listing Office: Keller Williams La Jolla.
Schedule A Tour Ask A Question Save To Favorites Follow 4314 Middlesex Drive

Overview

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.

Address 4314 Middlesex Drive

San Diego, CA 92116
Listing Status Active
Asking Price $2,550,000
Original Listing $2,550,000 @ 2026-03-11
Rooms
Formal Entry, Walk-In Closet, Exercise Room, Primary Bedroom, Laundry, Bonus Room, Kitchen, Living Room, Main Floor Bedroom, Family Room, Galley Kitchen, Primary Bathroom
Square Footage 2730 sf
Bedrooms 5
Full Bathrooms 3
Location
Directions Cross Street: Hilldale Road.
Market Area 92116 - Normal Heights
Neighborhood Kensington
Complex Kensington
School District Not Listed
Ownership
Age Restriction 0
Property Type
Mello-Roos Fee $0
HOA Fee $0
Public Records
County San Diego
Assessor Parcel# 4650410800
Geographic Areas

Airport Compatibility Zone: Montgomery Field

Community College District: San Diego CC

School District: San Diego Unified

Zip Code: 92116

Highway Locator

East of I-15

East of I-5

South of I-8

East of I-805

East of SR-163

South of SR-52

South of SR-56

South of SR-78

Ocean Distance 8.5 miles
Exterior
Style Single Family Residence
Material Not Listed
Lot Size ~ 8,982 sf
Fencing Not Listed
Topography Not Listed
Roof Composition
Swimming Pool In Ground
Parking
Driveway - Brick
Total Spaces: 4
Garage Spaces: 2
Non-Garage Spaces: 0 - 2.00
View Mountain(s)
Features
Year Built 1938
Laundry Location Gas Dryer Hookup,Individual Room,Electric Dryer Hookup
Elevator Not Listed
Cooling Central Air
Heating Natural Gas, Forced Air
Fireplaces Living Room (1)
Additional Parcels No
Appliances Yes
Assessments No
Association No
Association Fee 2 0
Attached Garage Yes
Below Grade Finished Area 0
Carport Spaces 0
Construction Materials Stucco
Cooling Yes
Eating Area Dining Room, Area
Heating Yes
Land Lease No
Laundry Yes
Levels Two
Living Area Source Assessor
Lot Size Source Assessor
Lot Size Units Square Feet
Main Level Bathrooms 0
Main Level Bedrooms 0
New Construction No
Number Of Units Total 0
Number Remotes 0
Parking Yes
Patio No
Pool Private No
Property Attached No
Sprinklers No
View Yes
Well Depth 0
Well Gallons Per Minute 0
Well Pump Horsepower 0
Well Report No
Monthly Payment Calculator
Property Tax estimate of 1% of listing price does not include local voter-approved bonds/assessments, supplemental taxes for new construction or ownership changes, extra local fees, etc.
Listing Source
Platform CRMLS
AOR San Diego
MLS Number 260005611SD
Courtesy of Keller Williams La Jolla
Listing Agent Patrick Mercer