2133 2nd Ave
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2133 2nd Ave

Dbottom 20%

San Diego, CA 92101

$4,500,000
STR-eligible · San Diego Tier 3 · TOT 13.75%

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

261 licensed short-term rentals within ½ mile (218 whole home), from the cities' license and permit lists of Nov 11, 2026.

Pass at asking: -$27,604/mo full cashflow at 20% down, 7.43% rate.

Works at $905,934 (80% under asking); even all cash loses money at asking.

Rent $9,036/mo from 19 leases of 3–5 bed houses within 2 mi ($8,074–$10,153).

Beds

4

Baths

5

Sqft

4,502

Year Built

1888

Days on Market

97

Property Type

Single Family

HOA/mo

N/A

MLS ID

260019114SD

This property is in San Diego (92101). View neighborhood stats →

Virtual Tour

About This Property

Steeped in history and overlooking the San Diego skyline, 2133 2nd Avenue is more than a residence—it is an architectural treasure and true collector's item. Built in 1888, this iconic Victorian masterpiece in the heart of Banker's Hill has been meticulously restored to honor its storied past while blending modern luxury. From the stately wrought iron gates to the intricate architectural details, every inch reflects timeless craftsmanship. Inside, more than 30 chandeliers and custom sconces illuminate beautifully curated interiors. A dramatic freestanding spiral staircase and reimagined vintage elevator create an unforgettable experience, while a hidden speakeasy and secluded backyard provide exceptional spaces for entertaining and relaxation. The home offers two elegant guest suites, an additional en suite bedroom, and an entire third-floor primary retreat with multiple view decks capturing panoramic views of the harbor, downtown skyline, Coronado Bridge, and breathtaking Pacific sunsets. Just moments from Balboa Park, Downtown, Little Italy, Petco Park, Coronado, La Jolla, and San Diego International Airport, the location is as exceptional as the home itself. Designated under the Mills Act, the property offers valuable property tax savings. Buyers may also purchase the home furnished and inquire about acquiring the adjacent three-unit building (2115 - 2119 2nd Ave), creating a rare opportunity for passive income, expansion, or a private compound. This is a once-in-a-generation opportunity to own one of San Diego's most extraordinary historic estates.

Mortgage Calculator

Est. Monthly Payment

$30,812

Principal & Interest$24,999
Property Tax$4,500
Insurance$1,312
%($900,000)
%
Loan Term

Location

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Zoned Schools

  • Elementary

    Washington Elementary · grades PK-5 · San Diego Unified

  • Middle

    Roosevelt International Middle · grades 6-8 · San Diego Unified

  • High

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

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

Comparable Properties

1 comp found

This Property

$9,036

vs

Comp Average

$7,520

Comps based on same zip code, similar beds (±1), price range (60-150%).

Investment Score

0D
Est. Monthly Rent
$9,036

19 leases of 3–5 bed houses within 2 mi · $8,074–$10,153

Monthly Cashflow

Rent − PITIA

-$21,775
Full Cashflow

Incl. vacancy, PM, maint, capex

-$27,604

What would make this work?

$27,604/mo short at 20% down; +$35,849/mo rent closes it.

Break-even price

80% under asking

$905,934
Break-even rent

$35,849/mo above the estimate

$44,885/mo
Cashflow at 35% down
−$22,916/mo
Down payment to break even

Negative even all-cash

Not reachable
Rate to break even

Negative even at a 0% loan

Not reachable

Mortgage (P+I)
$24,999
Cap Rate
-0.57%
Cash-on-Cash
-36.80%
DSCR

Need ≥ 1.25 for DSCR loan

0.29

NOI (Annual)
-$25,830
Price-to-Rent

Lower = better for investors

41.5

* 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.

Open Full Calculator
DCashflow−$27,604/mo