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  • 4391 Middlesex

4391 Middlesex, San Diego, CA 92116

$1,895,000 Approx. USD 3 beds, 3 baths
1,841 sqft
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Photo of Mark Shaffer

Mark Shaffer REALTOR® - Sales Associate 619-885-0988 m
619-294-3113 o
Lic#: 01375507
NRDS ID: 196521887
mark@smoothridehome.com Text Me
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Lic#: 01375507
NRDS ID: 196521887
mark@smoothridehome.com San Diego Central Office
2355 Northside Drive, Suite 180
San Diego, CA 92108
Phone: 619-294-3113
Fax: 619-521-0100
 San Diego Central 2355 Northside Drive, Suite 180
San Diego, CA 92108
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Fax: 619-521-0100
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Listing Agent


Brian J Aarestad | baarestad@bhhscal.com
Lic#: 01839557
Broker: Courtesy of Berkshire Hathaway HomeServices California Properties

Agent Remarks

Perched along the canyon rim in North Kensington, this beautifully updated home pairs classic architectural character with expansive views and exceptional indoor-outdoor living. Original hardwood floors, graceful archways, and a fireplace preserve its warmth and charm. At the heart of the home, the newly remodeled kitchen features an oversized waterfall-edge island, walk-in pantry, abundant cabinetry, stainless steel appliances, and brass accents. An adjoining dining room is ideal for everyday meals or entertaining, while the spacious living room offers an inviting, light-filled gathering space. Wake up to canyon views in a primary suite that embraces the setting. French doors open to the deck for morning coffee or unwinding at day's end. Two additional bedrooms welcome family and guests, while a dedicated office offers a quiet retreat for working from home. Outside is where the property truly distinguishes itself. An expansive view deck offers room for dining, lounging, and entertaining beneath market lights, overlooking the canyon and surrounding hills. Meandering paths lead through mature landscaping to outdoor spaces below, creating privacy and a connection to nature. Located in one of San Diego's most beloved neighborhoods, 4391 Middlesex Drive offers a remarkable combination of privacy, sweeping canyon views, and a peaceful retreat from the city, all within minutes of the restaurants, shops, and neighborhood charm that make Kensington so desirable.

Listing Details

Property type: Detached (Single Family)
Status: ACTIVE
MLS# 260024467
Price: $1,895,000
HOA Fee is $0.00
Beds: 3
Baths: 3 (3 full)
FP in Family Room fireplaces
Built in 1947
1,841 sqft
1 story
1.47 acres
Subdivision: KENSINGTON
County: San Diego
Zoning: R-1:SINGLE
Parking type: Detached,Garage - Two Door
Construction: Wood/Stucco
Appliances: Dishwasher,Disposal,Dryer,Microwave,Refrigerator,Washer,Range/Stove Hood,Gas Range
Parking description: Detached,Garage - Two Door
Heating description: Forced Air Unit
MLS area: Metro Uptown

Last Updated: 10/9/2026

 Days On Market (DOM): 20

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This listing belongs to the Metro Uptown MLS area

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Lat/Long: 32.773217, -117.099626.
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DISCLAIMER: There is NO WARRANTY, expressed or implied, for the accuracy of this information or its applicability to your financial situation. Please consult your financial and/or tax advisor. GET PRE-APPROVED The loan's interest rate will depend upon the specific characteristics of the loan transaction and credit profile up to the time of closing.

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Photo of Mark Shaffer

Mark Shaffer REALTOR® - Sales Associate 619-885-0988 m
619-294-3113 o
Lic#: 01375507
NRDS ID: 196521887
mark@smoothridehome.com Text Me
Call My Cell
Call My Office
Lic#: 01375507
NRDS ID: 196521887
mark@smoothridehome.com
San Diego Central Office
2355 Northside Drive, Suite 180
San Diego, CA 92108
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