About this home

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.

Facts and features

Schools

• Franklin Elementary School

  elementary · K-5 · 1.0 mi

  5

• Hoover High School

  high · 9-12 · 1.1 mi

  4

• Wilson Middle School

  middle · 6-8 · 1.5 mi

  3

• Children's Workshop School

  elementary · K-8 · 0.6 mi

• Lewis Middle School

  middle · 6-8 · 2.0 mi

  7

• Patrick Henry High School

  high · 9-12 · 3.3 mi

  9

Price history

• Oct 8, 2026 · Listed$1,895,000
• Sep 26, 2026 · Listing Removed—
• Sep 3, 2026 · Price Changed$1,995,000
• Jul 30, 2026 · Listing Removed—
• Jul 29, 2026 · Listed$2,150,000
• Jun 15, 2026 · Price Changed$2,275,000
• May 15, 2026 · Listed$2,375,000
• Jul 19, 2018 · Listing Removed$1,345,000

Tax history

• 2025$12,555 tax · $967,153 assessed
• 2024$11,579 tax · $948,190 assessed
• 2023$11,322 tax · $911,372 assessed
• 2022$11,016 tax · $893,503 assessed
• 2021$10,849 tax · $875,984 assessed
• 2020$10,717 tax · $867,002 assessed
• 2019$10,524 tax · $850,003 assessed
• 2018$9,841 tax · $833,337 assessed

Home value

$1,954,700

• Cotality$1,954,700
• Quantarium$1,889,043
• Collateral Analytics$1,975,000

Where it is