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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.
| Address |
4314 Middlesex Drive
San Diego, CA 92116 |
| Listing Status | Active |
| Asking Price | $2,550,000 |
| Original Listing | $2,550,000 @ 2026-03-11 |
| Square Footage | 2730 sf |
| Bedrooms | 5 |
| Full Bathrooms | 3 |
| Directions | Cross Street: Hilldale Road. |
| Market Area | 92116 - Normal Heights |
| Neighborhood | Kensington |
| Complex | Kensington |
| School District | Not Listed |
| Age Restriction | 0 |
| Property Type | |
| Mello-Roos Fee | $0 |
| HOA Fee | $0 |
| County | San Diego |
| Assessor Parcel# | 4650410800 |
| Geographic Areas |
Airport Compatibility Zone: Montgomery Field Community College District: San Diego CC |
| 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 |
| 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) |
| 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 |
| Platform | CRMLS |
| AOR | San Diego |
| MLS Number | 260005611SD |
| Courtesy of | Keller Williams La Jolla |
| Listing Agent | Patrick Mercer |
https://www.californiatophomes.com/260005611SD