4391 Middlesex Drive, KENSINGTON, CA

$1,995,000

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3

Beds

3

Baths

2,100

Square feet

1.47

Acres

About 4391 Middlesex Drive

Set on a quiet cul-de-sac in the heart of north Kensington, this extraordinary canyon rim home sits on nearly 1.5 acres and offers a truly rare opportunity to own the 3rd largest lot in the entire neighborhood. This tastefully remodeled single level home delivers a level of privacy, tranquility, and natural beauty that is almost impossible to find while still being moments from the restaurants, coffee shops, and boutiques along Adams Avenue. . Mature landscaping and expansive grounds create an estate-like feel while the home embraces sweeping canyon views from nearly every room. Inside, you're welcomed by beautiful original hardwood floors, abundant natural light, and a warm living room anchored by a fireplace and oversized windows framing the breathtaking scenery beyond. Stunning archways guide you from room to room, blending timeless architectural charm with tasteful modern updates. Designed for both everyday living and entertaining, the remodeled kitchen serves as the heart of the home with a gorgeous center island, designer finishes, ample cabinetry, and effortless flow into the main living spaces. The primary suite feels like a private retreat with endless canyon vistas, French doors opening to a spacious view deck, and a beautifully remodeled ensuite. Additional bedrooms are generously sized and filled with natural light. Outside, multiple entertaining areas, sprawling grounds, and the unmatched canyon backdrop create an atmosphere rarely found in Metro San Diego. Opportunities to own a property of this size, setting, and caliber in Kensington are exceptionally rare.

Open House

Sat, Sep 12th, 2026 @ 11am - 1pm

Features of 4391 Middlesex Drive

MLS® # 260018434
Price $1,995,000
Bedrooms 3
Bathrooms 3.00
Full Baths 3
Square Footage 2,100
Acres 1.47
Year Built 1947
Type Residential
Sub-Type Detached
Status Active

Community Information

Address 4391 Middlesex Drive
Area SAN DIEGO (92116)
Subdivision Kensington
City KENSINGTON
County San Diego
State CA
Zip Code 92116

Amenities

Parking Spaces 4
Parking Detached
# of Garages 2
View City,Mountains/Hills
Is Waterfront No
Has Pool No
Pool N/K

Interior

Appliances Dishwasher,Disposal,Dryer,Garage Door Opener,Refrigerator,Washer,Freezer,Gas Stove,Gas Range,Counter Top
Heating Forced Air Unit
Cooling Central Forced Air
Fireplace Yes
# of Fireplaces 1
Fireplaces FP in Living Room
Stories 1 Story

Exterior

Roof Flat
Construction Stucco

Additional Information

Date Listed July 29th, 2026
Days on Market 37
Zoning R-1:SINGLE
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Details

OfficeKeller Williams La Jolla

Listing Map

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