$4,995,000
4348 Middlesex
San Diego, CA, 92116
Welcome to the most spectacular estate to ever come to market in Kensington. A once in a lifetime opportunity to own a stunning Spanish-style residence with the coveted Mills Act in place! This rare offering represents a masterful blend of architectural heritage and modern luxury. Spanning over 6,000 sq. ft. total, the main residence includes 4 bedrooms and 5 bathrooms, complemented by a detached guesthouse. Designed for elevated living and unforgettable entertaining, the home rests on a rare flat, and fully usable double lot just under 20,000 sq. ft. Fully pocketing retractable glass doors in the living room open to a sweeping green lawn, an infinity-edge pool with grotto and unobstructed jaw-dropping views- creating a truly magical backdrop day and night. The chef’s kitchen is outfitted with high-end appliances including an Italian ILVE Range, Wolf Oven and Sub-Zero Refrigerator and is complemented by a separate dedicated bar-ideal for hosting at any scale.The Primary suite is a standout, featuring a remarkable dual steam walk-in shower with integrated touchscreen controls and built-in speakers along with two exceptionally large walk-in closets-an uncommon luxury for a property of this age and location. Executed to the highest standard, this estate sets a new benchmark for historic luxury living in Kensington.
Property Details
Price:
$4,995,000
MLS #:
2601054SD
Status:
Pending
Beds:
5
Baths:
6
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Kensington
Neighborhood:
92116normalheights
Listed Date:
Jan 14, 2026
Finished Sq Ft:
6,078
Lot Size:
19,846 sqft / 0.46 acres (approx)
Year Built:
1929
Schools
Interior
Appliances
DW, GD, IM, RF, BBQ, BI
Bathrooms
6 Full Bathrooms
Cooling
CA, ZN
Flooring
TILE, WOOD
Heating
FA, GAS, ZN
Laundry Features
GE, IR
Exterior
Other Structures
GHD
Parking Spots
4
Financial
Get Out There, A Simply Outgoing Approach to Life. James Outland Jr. is one of those rare people who simply has an outgoing approach to life. No matter the activity… from dune buggy riding to skydiving to motorcycling to riding the local Pismo Beach waves… James Outland Jr. approaches life with a “just get out there and do it” kind of attitude. A zest for Life. James’ zest for life is obviously apparent in his many exciting hobbies. In his spare time, he loves riding dune buggies or hi…
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Map
Current real estate data for Single Family in San Diego as of Feb 13, 2026
1,541
Single Family Listed
70
Avg DOM
538
Avg $ / SqFt
$1,172,298
Avg List Price
Community
- Address4348 Middlesex San Diego CA
- SubdivisionKensington
- CitySan Diego
- CountySan Diego
- Zip Code92116
Similar Listings Nearby
Property Summary
- Located in the Kensington subdivision, 4348 Middlesex San Diego CA is a Single Family for sale in San Diego, CA, 92116. It is listed for $4,995,000 and features 5 beds, 6 baths, and has approximately 6,078 square feet of living space, and was originally constructed in 1929. The current price per square foot is $822. The average price per square foot for Single Family listings in San Diego is $538. The average listing price for Single Family in San Diego is $1,172,298. To schedule a showing of MLS#2601054sd at 4348 Middlesex in San Diego, CA, contact your James Outland agent at 8057482262.
Courtesy of Red Rhino Realty, Inc.. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the California Regional Multiple Listing Service. Detailed information about real estate listings held by brokerage firms other than James Outland include the name of the listing broker. Neither the listing company nor James Outland shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. California Regional Multiple Listing Service. All rights reserved. 4348 Middlesex
San Diego, CA













































































