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$1,800,000

Sold
1239 N Dearborn St, Chicago, IL 60610
8 Beds
7 Baths
0 Square Feet
0.00 Acres Lot
Built in 1897
Sold
5 Units
Checked: 17 hours ago
Updated: Aug 19, 2025 at 10:50AM

Investment Summary


Monthly Cash Flow
-$10,244
Cap Rate
-1.2%
Cash-on-Cash Return
-29.7%
Debt Coverage Ratio
-0.20
Internal Rate of Return (5 years)
-24.6%

Property Description


0.00 Acres Lot
Built in 1897
Sold
5 Units

Once home to great American author Ernest Hemingway and walking distance to Chicago's amazing lakefront, 1239 N. Dearborn St. is a 7 bed/6.5 bath, historic brownstone in the heart of the Gold Coast with three decks, a patio, a coach house and a two-car garage. Originally built in 1898 and located on a 3,300-square-foot lot that sits on a lovely, tree-lined stretch of Dearborn, amid some of Chicago's finest homes, the literary history here is enchanting: After their honeymoon in 1921, Hemingway and his wife Hadley lived in an apartment on the fourth floor before moving to Paris, where he wrote "The Sun Also Rises," "A Farewell to Arms," and his memoir, "A Moveable Feast." Most recently situated as a multifamily divided up into rentals, the entire brownstone plus coach house is now for sale, presenting endless possibilities as an investment property including the option to renovate to transform its beautiful bones into a multilevel, single-family home. The brick and limestone exterior has been maintained to uphold its stately, turn-of-the-century character, including tall arched windows and decorative stonework. Inside, the main level flaunts high ceilings, original hardwood floors and millwork details across a foyer, a light-filled formal living room, a dining room with fireplace, a back-of-the-house kitchen, and a bonus space that links to two decks (9'4" x 15'2" and 12'7" x 7'4"). Upstairs, the second level is perfect for a deluxe primary suite and currently features three bedrooms (two that are ensuite, one with a balcony and another with a walk-in closet), two full baths, and upstairs laundry. The top level reveals three additional bedrooms, two more full baths, and a bonus space that's ideal for a den or office. Downstairs, the ground level features two studio spaces (one with a kitchenette) that connect to a large outdoor patio (23'5" x 24'10"). Plus, there's a basement level with more bonus space, yet another full bath, a laundry room, utilities, and abundant storage. Situated above the detached garage, the bi-level coach house features a foyer, a living room, a kitchen, three bedrooms and a full bath, and has the potential to be a fabulous standalone apartment for in-laws, extended-stay guests or an au pair. With a spectacular location that's steps from the 3 Arts Club and Green City Market's outdoor farmers market, not to mention Chicago's most prestigious schools and world-class dining and shopping along the Mag Mile and Oak Street, 1239 N. Dearborn St. is a truly one-of-a-kind property with untapped potential and incredible value built right in.

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Location


Property Details


Parking

  • Description: Attached Garage
  • Details: Garage, On Site, Detached
  • Garage Spaces: 2
  • Spaces Total: 2

Bedroom Information

  • # of Bedrooms: 8

Bathroom Information

  • # of Baths (Full): 1
  • # of Baths (Partial): 0
  • # of Baths (Total): 7.0

Interior Features

  • # of Rooms: 20
  • # of Stories: 1
  • Basement: Yes
  • Basement Description: Unfinished, Partial

Exterior Features

  • Exterior Walls Materials: Masonry

Land Information

  • Land Use: Residential Income
  • Land Use Subtype: Apartments (general)

Lot Information

  • Parcel ID: 1704224009
  • Lot Size: 0 sqft

Property Information

  • Property Type: Multi Family
  • Year Built: 1897

Tax Information

  • Annual Tax: $46,381

Utilities

  • Heating: Natural Gas

Location

  • County: Cook

Listing Details


Listed by:
Timothy Salm
Jameson Sotheby's Intl Realty
(312) 929-1564

Source:
Midwest Real Estate Data (MRED)
MLS#: 12382487
Midwest Real Estate Data (MRED)

Investment Summary


Monthly Cash Flow
-$10,244
Cap Rate
-1.2%
Cash-on-Cash Return
-29.7%
Debt Coverage Ratio
-0.20
Internal Rate of Return (5 years)
-24.6%

Purchase Details

Find an Agent

Purchase price:
$1,800,000
Amount financed:
-$1,440,000
Down payment:
$360,000
Closing costs:
$54,000
Rehab costs:
$0
Initial cash invested:
$414,000
Square feet:
0
Cost per square foot:
n/a
Monthly rent per square foot:
n/a

Financing Details

Find a Lender

Loan amount:
$1,440,000
Loan to value ratio:
80.0%
Loan type:
Amortizing
Term:
30 years
Interest rate:
5.875%
Principal & interest:
$8,518
Property tax:
$3,865
Insurance:
$217
Private mortgage insurance (PMI):
$0
Monthly payment:
$12,600

Operating Income

Find a Property Manager

% Rent Monthly Yearly
Gross rent:
$3,100 $37,200
Vacancy loss: (6%)
6% -$186 -$2,232
Operating income:
$2,914 $34,968

Operating Expenses


% Rent Monthly Yearly
Property taxes: (125%)
125%-$3,865-$46,382
Insurance: (7%)
7%-$217-$2,604
Property management: (8%)
8%-$248-$2,976
Repairs & maintenance: (5%)
5%-$155-$1,860
Capital expenditures: (5%)
5%-$155-$1,860
HOA fees: (n/a)
n/an/an/a
Total operating expenses: (150%)
150%-$4,640-$55,682

Cash Flow


Monthly Yearly
Net operating income:
-$1,726 -$20,712
Mortgage payments:
-$8,518 -$102,216
Cash flow:
$10,244 $122,928