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.
Property Details
Price:
$1,895,000
MLS #:
260024467SD
Status:
Active
Beds:
3
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Kensington
Neighborhood:
92116normalheights
Listed Date:
Oct 8, 2026
Finished Sq Ft:
1,841
Lot Size:
64,033 sqft / 1.47 acres (approx)
Year Built:
1947
See this Listing
Schools
Interior
Appliances
DW, GD, MW, RF, GR, HOD
Bathrooms
3 Full Bathrooms
Cooling
CA
Heating
FA, GAS
Laundry Features
ELC, GAS, IR
Levels
A
Exterior
Fencing
PTL
Garage Spaces
2
Parking Spots
6
Parking Total
6
Roof
FLTR
Financial
Map
Community
- Address4391 Middlesex San Diego CA
- SubdivisionKensington
- CitySan Diego
- CountySan Diego
- Zip Code92116
Subdivisions in San Diego
- Bay Park
- BP
- Carmel Mountain Ranch
- Carmel Valley
- Casa Dorado 32501
- CAV
- CH
- Chula Vista
- City Heights
- Civita CIVI
- Clairemont
- CLM
- College Grove
- Crown Point
- Del Cerro
- Downtown
- Downtown Area DOWN
- DWTN
- East San Diego
- Encanto
- ENCTO
- Escala ESCL
- Hillcrest
- Imperial Beach
- Kearny Mesa
- Kensington
- La Jolla
- La Mesa
- Linda Vista
- Logan Heights
- LV
- Middletown
- Mira Mesa
- Mirador MIRD
- Mirasol MIR
- Mission Beach
- Mission Hills
- Mission Valley
- Mission Village
- Mount Helix
- Normal Heights
- North Park
- NP
- Ocean Beach
- Old Town
- Pacific Beach
- Paradise Hills
- Park Villas PKVL
- Park Vista PV
- Point Loma
- Poway
- Rancho Bernardo
- Rancho Pacifica 1 261701
- Rancho Penasquitos
- Rancho Santa Fe
- Sabre Spr
- San Carlos
- San Diego
- San Ysidro
- SANT
- Santaluz
- Scripps Ranch
- SD
- Serra Mesa
- Smoke Tree SMTR
- South Sd
- Stonebridge 3700
- Talmadge
- The Lakes LK
- Tierrasanta
- Torrey Highlands
- University City
- University Heights
- Villa Portofino 32283
- Woodcrest WT
Market Summary
Current real estate data for Single Family in San Diego as of Oct 09, 2026
2,325
Single Family Listed
74
Avg DOM
574
Avg $ / SqFt
$1,211,760
Avg List Price
Property Summary
- Located in the Kensington subdivision, 4391 Middlesex San Diego CA is a Single Family for sale in San Diego, CA, 92116. It is listed for $1,895,000 and features 3 beds, 3 baths, and has approximately 1,841 square feet of living space, and was originally constructed in 1947. The current price per square foot is $1,029. The average price per square foot for Single Family listings in San Diego is $574. The average listing price for Single Family in San Diego is $1,211,760.
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