4314 Middlesex Drive

4314 Middlesex Drive

D

San Diego, CA 92116

$2,550,000
NEW — 0d on market

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

View on MLS

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

Principal & Interest$12,894
Property Tax$2,550
Insurance$744
%($510,000)
%

Investment Score

0D
Est. Monthly Rent
$7,461
Monthly Cashflow

Rent − PITI − HOA

$-8,727
Full Cashflow

Incl. vacancy, PM, maint, capex

$-12,568

Mortgage (P+I)
$12,894
Cap Rate
0.15%
Cash-on-Cash
-20.53%
DSCR

⚠️ Need ≥ 1.25 for DSCR loan

0.46
Break-even Rent
$16,188

NOI (Annual)
$3,912
Price-to-Rent

Lower = better for investors

28.5

* 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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