4314 Middlesex Drive
DSan Diego, CA 92116
Beds
5
Baths
3
Sqft
2,730
Year Built
1938
Days on Market
0
Property Type
Single Family
HOA/mo
N/A
MLS ID
260005611SD
Description
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.
Mortgage Calculator
Est. Monthly Payment
$16,188
Comparable Properties
4 comps foundThis Property
$7,461
Comp Average
$7,387
4778 Panorama Drive
6bd / 2ba · 2,320 sqft · Single Family
$1.90M
Est. $6,196/mo
4811 Alder Drive
5bd / 4ba · 3,222 sqft · Single Family
$2.50M
Est. $7,854/mo
1414 Franciscan Way
5bd / 3.5ba · 3,826 sqft · Single Family
$2.79M
Est. $7,559/mo
4136 Palisades Road
5bd / 3.5ba · 3,647 sqft · Single Family
$3.73M
Est. $7,937/mo
Comps based on same zip code, similar beds (±1), price range (60-150%).
Investment Score
Rent − PITI − HOA
Incl. vacancy, PM, maint, capex
⚠️ Need ≥ 1.25 for DSCR loan
Lower = better for investors
* Defaults: 20% down, 6.5% rate, 30yr.
Estimates only. Not financial advice. Verify all figures independently with a licensed professional before making any investment decision.
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