4186 Hilldale Road
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4186 Hilldale Road

Dbottom 20%

San Diego, CA 92116

$2,100,000
STR-eligible · San Diego Tier 3 · TOT 12.75%

One license per person in San Diego: whether you can hold it depends on you, not only the home.

13 licensed short-term rentals within ½ mile (4 whole home), from the cities' license and permit lists of Nov 9, 2026.

Pass at asking: -$11,614/mo full cashflow at 20% down, 7.43% rate.

Works at $587,854 (72% under asking), or at all cash.

Rent $5,863/mo from 18 leases of 3–5 bed houses within 2 mi ($5,124–$6,095).

Beds

4

Baths

3

Sqft

2,587

Year Built

1927

Days on Market

47

Property Type

Single Family

HOA/mo

N/A

MLS ID

260023326SD

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

Virtual Tour

About This Property

Situated in an exceptional location in the heart of Kensington Heights, this 1927 Spanish-style home is elevated above the street, offering timeless character, with a spacious indoor-outdoor layout. Set on a generous lot, the home blends classic architectural details with comfortable everyday living. A covered front porch with panoramic views, welcomes you inside to original hardwood floors, arched openings, exposed wood beams, and a beautiful fireplace that anchors the main living room. The spacious kitchen offers abundant cabinetry and flows effortlessly into the adjoining dining and entertaining areas. The main-level primary suite features a large, dual-entrance walk-in closet, an updated bathroom, and direct backyard access. Upstairs features an expansive living area with two bedrooms, a full bath, and large bonus room with a kitchenette—creating a flexible space that offers rare independence and privacy for adult children, extended family, or long-term guests. Outside, the private backyard is built for enjoying San Diego’s year-round weather, showcasing a large, covered patio, mature landscaping, multiple seating areas, and a Spanish-style fountain as its centerpiece. Plantation shutters throughout and a detached two-car garage complete this unique property. Located just minutes from Kensington village's popular restaurants, boutiques, and tree-lined streets, you will enjoy a vibrant community atmosphere with convenient access to Normal Heights, North Park, Mission Valley and everything central San Diego has to offer.

Mortgage Calculator

Est. Monthly Payment

$14,379

Principal & Interest$11,666
Property Tax$2,100
Insurance$612
%($420,000)
%
Loan Term

Location

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Zoned Schools

  • Elementary

    Franklin Elementary · grades K-5 · San Diego Unified

  • Middle

    Lewis Middle · grades 6-8 · San Diego Unified

    or Wilson Middle · grades 6-8 · San Diego Unified

    Choice area: the district lets families here pick either school.

  • High

    Henry High · grades 9-12 · San Diego Unified

    or Hoover High · grades 9-12 · San Diego Unified

    Choice area: the district lets families here pick either school.

The district's assigned schools for this parcel, from its attendance boundaries and rules. Boundaries change: confirm with the district before you buy.

Investment Score

2D
Est. Monthly Rent
$5,863

18 leases of 3–5 bed houses within 2 mi · $5,124–$6,095

Blended 50/50 with a property-level estimate

Monthly Cashflow

Rent − PITIA

-$8,515
Full Cashflow

Incl. vacancy, PM, maint, capex

-$11,614

What would make this work?

$11,614/mo short at 20% down; 100% down or +$15,083/mo rent closes it.

Break-even price

72% under asking

$587,854
Break-even rent

$15,083/mo above the estimate

$20,946/mo
Cashflow at 35% down
−$9,426/mo
Down payment to break even

$2,100,000 cash

100%
Rate to break even

Negative even at a 0% loan

Not reachable

Mortgage (P+I)
$11,666
Cap Rate
0.20%
Cash-on-Cash
-33.18%
DSCR

Need ≥ 1.25 for DSCR loan

0.41

NOI (Annual)
$4,148
Price-to-Rent

Lower = better for investors

29.8

* Modelled at 20% down, 7.43% rate, 30yr · vacancy 8% · PM 10% · capex 5% · maintenance 1%/yr.

Estimates only. Not financial advice. Verify all figures independently with a licensed professional before making any investment decision.

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DCashflow−$11,614/mo