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.
Property Details
Price:
$2,375,000
MLS #:
260011908SD
Status:
Active
Beds:
3
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Kensington
Neighborhood:
92116normalheights
Listed Date:
May 15, 2026
Finished Sq Ft:
2,100
Lot Size:
64,033 sqft / 1.47 acres (approx)
Year Built:
1947
See this Listing
Schools
Interior
Appliances
DW, FZ, GD, RF, GR, GS, CT
Bathrooms
3 Full Bathrooms
Cooling
CA
Heating
FA, GAS
Laundry Features
ELC, GAS, IR
Levels
A
Exterior
Construction Materials
STC
Fencing
PTL
Garage Spaces
2
Parking Spots
4
Parking Total
4
Roof
FLTR
View
MT
Financial
Map
Community
- Address4391 Middlesex Drive 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 May 20, 2026
1,906
Single Family Listed
64
Avg DOM
616
Avg $ / SqFt
$1,340,547
Avg List Price
Property Summary
- Located in the Kensington subdivision, 4391 Middlesex Drive San Diego CA is a Single Family for sale in San Diego, CA, 92116. It is listed for $2,375,000 and features 3 beds, 3 baths, and has approximately 2,100 square feet of living space, and was originally constructed in 1947. The current price per square foot is $1,131. The average price per square foot for Single Family listings in San Diego is $616. The average listing price for Single Family in San Diego is $1,340,547.
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4391 Middlesex Drive
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