4391 Middlesex DriveSan Diego, CA 92116

Single Family · 3 Beds · 3 Full Baths · 2,100 Sq. ft. | 1.47 Acres
$2,275,000 Active

4391 Middlesex Drive Overview

Time on Site:
45 days
Visits:
0

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.

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4391 Middlesex Drive Facts & Features

  • Type Single Family
  • Sq. ft. 2,100
  • Price/Sq.ft. $1,083
  • Lot 1.47 Acres

Details

General

Association/HOA

  • Association: No

Building Information

  • New Construction: No
  • Year Built: 1947

Location/Region

  • Country: US
  • County Or Parish: San Diego
  • MLS Area Major: 92116 - Normal Heights
  • Postal City: SAN DIEGO
  • Subdivision Name: Kensington

Rent/Lease Information

  • Land Lease: No

General Information

  • Listing Terms: Cash,Conventional,FHA,VA Loan
  • Parcel Number: 4650201000
  • Property Sub Type: Single Family Residence
  • Property Type: Residential
  • Senior Community: No
  • Zoning: R-1:SINGLE

Interior

Parking Information

  • Garage Spaces: 2.0
  • Garage: Yes

Beds/Baths

  • Bathrooms Full: 3
  • Bathrooms Half: 0
  • Bathrooms Total: 3
  • Bedrooms Total: 3

General Information

  • Appliances: Counter Top,Dishwasher,Freezer,Gas Cooktop,Disposal,Gas Range,Refrigerator
  • Fireplace Features: Living Room
  • Fireplace: Yes
  • Interior Features: Separate/Formal Dining Room,Eat-in Kitchen,Bedroom on Main Level,Walk-In Pantry
  • Laundry Features: Electric Dryer Hookup,Gas Dryer Hookup,Laundry Room
  • Levels: One
  • Living Area: 2100.0
  • Living Area Source: Assessor
  • Spa: No
  • Stories: 1
  • Stories Total: 1

Exterior

Parking Information

  • Open Parking Spaces: 2.0
  • Parking Features: Driveway
  • Parking Total: 4.0

Lot Information

  • Lot Size Acres: 1.47
  • Lot Size Area: 64033.0
  • Lot Size Source: Assessor
  • Lot Size Square Feet: 64033.0
  • Lot Size Units: Square Feet

Waterfront/View

    Building Exterior/Construction

    • Attached Garage: No
    • Construction Materials: Stucco
    • Property Attached: No
    • Roof: Flat

    General Information

    • Fencing: Partial
    • Pool Features: None
    • Pool Private: No

    4391 Middlesex Drive Neighborhood

    Community

    92116 (San Diego) Demographics

    36
    Median Age
    9,423
    Population Density (per sq. mile)
    64%
    College Educated
    $78,697
    Estimated Median Income
    5,406
    Estimated Total Home Owners
    10,854
    Estimated Total Renters
    33% / 67%
    Estimated Owner / Renter Divide
    2
    Estimated Average Household Size
    Community data courtesy of LiveBy, Inc.

    Schools

    School data courtesy of LiveBy, Inc. School ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating.

    4391 Middlesex Drive Monthly Cost

    $
    $ %
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    $
    $
    * All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

    4391 Middlesex Drive Market Data

    Based on the last 30 days in this zip code

    $1,260,067
    Average List Price
    $913
    Average Price per Square Foot
    18
    Properties Sold
    37
    Average Days on Market
    61
    Properties for Sale
    Calculations provided by Reliance Network

    4391 Middlesex Drive History

    Date Event Value Agent
    6/15/2026Source: CRMLS Price Reduction
    $2,275,000 -4.2%
    5/15/2026Source: CRMLS Added to Database
    May 15, 2026
    Listing provided courtesy of Keller Williams La JollaPatrick Mercer- MLS# 260011908SDMLS ProviderContact Information: [email protected] - 858-457-9400