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Tamsin Enos, DRE#02152651, REALTOR®
(805) 234-1337

4314 Middlesex Drive, San Diego, CA 92116

$2,550,000
  • 4314 Middlesex Drive, San Diego, CA 92116 Main Photo

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Active
BEDS5 BATHS3 full SQUARE FEET2,730 MLS#260005611SD
STATUSActive PROPERTY TYPEResidential - Single Family SUBDIVISIONKensington

Listing Courtesy of: Keller Williams La Jolla
Agency Phone: 858-457-9400
Associate Name: Patrick Mercer
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Listing Shown by: Farrell Smyth, Inc.
Associate Name: Tamsin Enos, DRE#02152651, REALTOR®


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 neighborhoods most iconic streets.

4314 Middlesex Drive | MLS# 260005611SD

This single family home located at 4314 Middlesex Drive, San Diego, CA 92116 is currently listed for sale with an asking price of $2,550,000. This property was built in 1938 and has 5 bedrooms and 3 full baths with 2730 sq. ft. Middlesex Drive is located in the Kensington subdivision. Search Kensington real estate on tamsinenos.farrellsmyth.com today.

Property Features

Property Type: Residential - Single Family
Cooling: Central Air
Garage: 2 car attached
Heating: Forced Air, Natural Gas
Lot Size: 0.21 Acres
Roof Type: Composition
Stories: 2.0
Year Built: 1938

Amenities

Separate/Formal Dining Room
Bedroom on Main Level
Galley Kitchen
Walk-In Closet(s)
Brick Driveway

Feature Descriptions

Appliances: Dishwasher, Free-Standing Range, Gas Cooking, Gas Cooktop, Disposal, Gas Oven, Gas Range, Microwave, Refrigerator
Days on Site: 27
Exterior: Stucco
Fireplace: Living Room
Laundry: Electric Dryer Hookup, Gas Dryer Hookup, Laundry Room
Parcel#: 4650410800
Pool: In Ground
Special View Info: Mountain(s)

Listed By / Shown By

Listed By

Agency Name: Keller Williams La Jolla
Agency Phone: 858-457-9400
Agent Name: Patrick Mercer

agent picture

Shown By

Agent Name: Tamsin Enos, DRE#02152651, REALTOR®
Agent Phone: (805) 234-1337
Agency Title: Farrell Smyth, Inc.

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Estimate Your Payment

Estimated Payment

$ 6,418.94 per month $5,675.19 Principal & Interest $0.00 Property Tax (data not provided by mls) $743.75 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 04/06/2026. The listing information on this page last changed on 04/06/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Mon 04/06/2026 4:35:15 AM EST) or CRMLS (last updated Mon 04/06/2026 12:27:22 AM EST). Real estate listings held by brokerage firms other than Farrell Smyth, Inc. may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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