4391 Middlesex Drive
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4391 Middlesex Drive

D

San Diego, CA 92116

$2,375,000
NEW — 6d

Beds

3

Baths

3

Sqft

2,100

Year Built

1947

Days on Market

6

Property Type

Single Family

HOA/mo

N/A

MLS ID

260011908SD

This property is in San Diego (92116). View neighborhood stats →

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About This Property

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.

Mortgage Calculator

Est. Monthly Payment

$15,077

Principal & Interest$12,009
Property Tax$2,375
Insurance$693
%($475,000)
%

Location

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Investment Score

0D
Est. Monthly Rent
$5,370
Monthly Cashflow

Rent − PITIA

$-9,707
Full Cashflow

Incl. vacancy, PM, maint, capex

$-12,922

Mortgage (P+I)
$12,009
Cap Rate
-0.46%
Cash-on-Cash
-32.64%
DSCR

Need ≥ 1.25 for DSCR loan

0.36
Break-even Rent
$22,151

NOI (Annual)
$-10,947
Price-to-Rent

Lower = better for investors

36.9

* 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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