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4391 Middlesex DRSan Diego, CA 92116

For Sale

$1,895,000

Smart Buyer Rebate $18,950

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.

Listed by Brian Aarestad

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License #01839557

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Berkshire Hathaway HomeServices California Properties

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8585253262

Last updated October 08, 2026

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Source: CRMLS #260024467SD

Listing Facts

  • TypeSingle-family
  • NeighborhoodKensington
  • Bedrooms3
  • Bathrooms3
  • Days on Prevu23
  • Size1,841 sqft
  • Price per sqft$1,029

Amenities

  • Dishwasher
  • Air Conditioning
  • Parking

Location

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Listing History

10/08/2026
Listed by Berkshire Hathaway HomeServices California Properties
$1,895,000
  1. 10/08/2026$1,895,000
    Listed by Berkshire Hathaway HomeServices California Properties

Property Details for 4391 Middlesex DR

Exterior

Construction

  • Roof: Flat
  • Stories: 1
  • Stories Total: 1
  • Year Built: 1947

Features

  • Fencing: Partial

Measurements

  • Lot Size Acres: 1.47
  • Lot Size Area: 64,033
  • Lot Size Source: Assessor
  • Lot Size Square Feet: 64,033
  • Lot Size Units: Square Feet

Financial

Taxes

  • Parcel Number: 4650201000

Interior

Features

  • Appliances: Dishwasher, Disposal, Gas Range, Microwave, Refrigerator, Range Hood
  • Fireplace Features: Family Room
  • Fireplace: Yes
  • Interior Features: Pantry

Measurements

  • Living Area: 1,841
  • Living Area Source: Assessor

Rooms

  • Bathrooms Full: 3
  • Bathrooms Total Integer: 3
  • Bedrooms Total: 3

Other

Location

  • Subdivision Name: Kensington

Parking

Parking

  • Garage Spaces: 2
  • Garage: Yes
  • Open Parking Spaces: 4
  • Parking Features: Garage, Paved
  • Parking Total: 6

Utilities

Equipment

  • Cooling: Central Air
  • Has Cooling: Yes
  • Heating: Forced Air, Natural Gas
  • Has Heating: Yes
  • Laundry Features: Electric Dryer Hookup, Gas Dryer Hookup, Laundry Room

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 3 bedrooms and 3 bathrooms in this single-family home at 4391 Middlesex DR.

Does this single-family home have parking?

Yes, there are 2 parking spaces available for 4391 Middlesex DR.

How does 4391 Middlesex DR compare to other single-family homes in Kensington?

This single-family home is listed 6% above the average price for single-family homes in Kensington and has been on the market for 81 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 1,841 sqft.

4391 Middlesex DR is a 3-bedroom, 3-bath single-family home for sale in San Diego CA 92116. Available on Prevu for 23 days at $1,895,000. This residence features 1,841 square feet of living space, located in Kensington. The median listing price for single-family homes in this area is $1,543,750. Additional amenities include dishwasher, air conditioning, and parking. Explore more single-family home listings in San Diego.

Based on information from California Regional Multiple Listing Service, Inc. and/or other sources. All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by Prevu or the MLS. Information is provided exclusively for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.