Properties

San Diego, CA 92116 4314 Middlesex Drive

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Presented By: Patrick Mercer with Keller Williams La Jolla;
  • MLS# 260005611SD
  • 03/10/2026
  • Get pre-approved
  • Request Tour
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  • Beds • 5
  • Baths • 3
  • SQFT • 2,730
  • Garage • 2

Home Details

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 โ€” 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 neighborhoodโ€™s most iconic streets.
Presented By: Patrick Mercer with Keller Williams La Jolla;

Interior Features for 4314 Middlesex Drive

Bedrooms

Total Bedrooms5

Bathrooms

Half Baths0
Total Baths3

Other Interior Features

LivingAreaSourceAssessor
Air Conditioning Y/NYes
Fireplace FeaturesLiving Room
Fireplace Y/NYes
Heating Y/NYes
Interior AmenitiesSeparate/Formal Dining Room, Bedroom on Main Level, Galley Kitchen, Walk-In Closet(s)
Laundry FeaturesElectric Dryer Hookup, Gas Dryer Hookup, Laundry Room
Total Stories2

General for 4314 Middlesex Drive

AppliancesDishwasher, Free-Standing Range, Gas Cooking, Gas Cooktop, Disposal, Gas Oven, Gas Range, Microwave, Refrigerator
Attached Garage Yes
CitySan Diego
Construction MaterialsStucco
CoolingCentral Air
CountySan Diego
DirectionsCross Street: Hilldale Road.
Full Baths3
Garage Spaces2
Garage Y/NYes
HOANo
HeatingForced Air, Natural Gas
Land Lease Y/NNo
LevelsTwo
Listing TermsCash, Conventional, VA Loan
Living Area2730
Lot Size Square Feet8982
Lot Size UnitsSquare Feet
MLS Area92116 - Normal Heights
New ConstructionNo
Occupancy TypeOwner
Open Parking Spaces2
Pool FeaturesIn Ground
PostalCitySAN DIEGO
Property Attached Y/NNo
Property Sub Type AdditionalSingle Family Residence
Property SubtypeSingle Family Residence
Property TypeResidential
RoofComposition
Senior Community Y/NNo
Standard StatusActive
StatusActive
Stories Count2
Subdivision NameKensington
ViewMountain(s)
Virtual TourClick here
Year Built1938

Exterior for 4314 Middlesex Drive

Exterior AmenitiesBrick Driveway
Lot Size Acres0.2062
Lot Size Area8982
Lot Size SourceAssessor
Private PoolNo
SpaNo
Total Parking4

Additional Details

Price History

Schools

High School Hubert H Humphrey Middle School
Middle School N/A
Elementary School Big Hollow Elementary School

Connect Realty

Price $2,550,000
MLS#260005611SD
List Date 03/10/2026
Property Type Single Family
Phone 888.795.6274
Get pre-approved
Request Tour
Request Info
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