Set on one of the most prominent and sought-after streets in all of Kensington, this stunning Colonial Revival residence offers timeless architecture, sweeping canyon views, and an incredible sense of privacy. A Mediterranean-inspired courtyard welcomes you at the front of the home, creating a warm and inviting entry — the perfect setting for morning coffee or gathering with friends before heading out to enjoy the neighborhood. Inside, the home features a tremendous layout thoughtfully designed to maximize both comfort and views. One of the most striking spaces is the formal step-down living room, beautifully framed by a fireplace and two bifold windows that perfectly capture the canyon and courtyard views beyond. Natural light fills the home, while large windows throughout frame picturesque outlooks from many of the main living spaces and bedrooms. The floor plan flows effortlessly, offering a seamless balance of everyday livability and ideal spaces for entertaining. The backyard lives like a private retreat, complete with an elegant pool, generous outdoor living areas, and breathtaking canyon views that create a peaceful backdrop for relaxing or entertaining. The home has recently undergone a thoughtful transformation including a brand new roof, fully paid solar, two Tesla backup batteries, and new landscaping designed by a well-known local landscape architect. Located in highly desirable North Kensington just moments from Kensington Village and Adams Avenue, this is a rare opportunity to own a canyon-view home on one of the neighborhood’s most iconic streets.
Property Details
Price:
$2,550,000
MLS #:
260005611SD
Status:
Active
Beds:
5
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
Kensington
Neighborhood:
92116normalheights
Listed Date:
Mar 10, 2026
Finished Sq Ft:
2,730
Lot Size:
8,982 sqft / 0.21 acres (approx)
Year Built:
1938
See this Listing
Schools
Interior
Appliances
DW, GD, MW, RF, GO, GR, GS, FSR, GAS
Bathrooms
3 Full Bathrooms
Cooling
CA
Heating
FA, GAS
Laundry Features
ELC, GAS, IR
Levels
U
Exterior
Attached Garage YN
1
Construction Materials
STC
Garage Spaces
2
Parking Spots
4
Parking Total
4
Roof
CMP
View
MT
Financial
Map
Community
- Address4314 Middlesex Drive San Diego CA
- SubdivisionKensington
- CitySan Diego
- CountySan Diego
- Zip Code92116
Subdivisions in San Diego
- Bay Park
- BP
- Campo
- Carmel Mountain Ranch
- Carmel Valley
- CAV
- Chula Vista
- City Heights
- Civita CIVI
- Clairemont
- Clifton Heights CLFH
- COL
- College Grove
- Coronado Shores
- Coronado Village
- Crown Point
- Del Cerro
- Del Mar
- Downtown
- Downtown DT
- DWTN
- East Del Mar
- East Escondido
- East San Diego
- El Cajon
- Emerald Hills EMER
- Encanto
- ENCTO
- ESD
- Hampton Place HAMP
- HI
- High Country 780
- Hillcrest
- Horizon HORZ
- Imperial Beach
- Kearny Mesa
- Kensington
- Knightsbridge KBRG
- La Jolla
- La Mesa
- Lemon Grove
- Linda Vista
- Logan Heights
- LV
- MB
- Middletown
- Mira Mesa
- Mirador MIRD
- Mission Beach
- Mission Greens R1 MG
- Mission Hills
- Mission Valley
- Mission Village
- MV
- National City
- Normal Heights
- North Park
- NP
- OB
- Ocean Beach
- Ocean View Terrace OVTR
- Old Town
- Pacific Beach
- PalaciMaPD
- Paradise Hills
- PH
- Point Loma
- Poway
- Presidio PRES
- Rancho Bernardo
- Rancho Pacifica 1 261701
- Rancho Penasquitos
- Rancho Santa Fe
- RB
- Regency Villas RGVL
- Sabre Spr
- San Carlos
- San Diego
- San Ysidro
- SANT
- Santaluz
- Scripps Ranch
- SD
- Serra Mesa
- Solana Beach
- South Sd
- Spring Valley
- Stonecrest 892
- Talmadge
- The Heights
- TheBluffs2
- Tierrasanta
- Torrey Highlands
- Trails of Rancho Bernardo
- UC
- University City
- University Heights
Market Summary
Current real estate data for Single Family in San Diego as of Apr 23, 2026
2,440
Single Family Listed
69
Avg DOM
569
Avg $ / SqFt
$1,223,128
Avg List Price
Property Summary
- Located in the Kensington subdivision, 4314 Middlesex Drive San Diego CA is a Single Family for sale in San Diego, CA, 92116. It is listed for $2,550,000 and features 5 beds, 3 baths, and has approximately 2,730 square feet of living space, and was originally constructed in 1938. The current price per square foot is $934. The average price per square foot for Single Family listings in San Diego is $569. The average listing price for Single Family in San Diego is $1,223,128. To schedule a showing of MLS#260005611sd at 4314 Middlesex Drive in San Diego, CA, contact your Pacific Sotheby’s International Realty agent at 6193633000.
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4314 Middlesex Drive
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