Active

$475,000

2042 Winchester Avenue, Chicago, IL 60614
2 Beds2 Baths0 sqft1 days
2042 Winchester Avenue·Chicago, IL 60614
2Bedrooms
2Bathrooms
0Sq Ft
About This Home

SHORT TERM RENTAL AND AIRBNB FRIENDLY - RARE OPPORTUNITY! Sun-filled and full of character, this 2-bedroom, 2-bathroom duplex-up blends vintage Chicago charm with modern loft-style living in the heart of Bucktown. Soaring ceilings, exposed brick and beautiful hardwood floors create a warm, airy backdrop, while oversized windows and skylights fill the home with natural light. The updated kitchen features crisp white cabinetry, granite countertops, stainless steel appliances and a breakfast island that flows seamlessly into the living and dining space. A dramatic spiral staircase leads to the spacious lofted primary suite with vaulted ceilings and skylights. The second bedroom offers wonderful flexibility for guests or a home office, while two full baths and in-unit laundry add everyday convenience. Outside, a large private deck creates your own urban retreat. Central air, additional storage and deeded exterior parking complete this distinctive home in a prime Bucktown location steps from local retail shopping, restaurants, and the 606 trail. This fantastic home is perfect not only for owner-occupants but also presents an incredible investment opportunity, as this HOA allows short term and nightly vacation rentals. Ask for details and schedule your showing today!

MLS# 12758906Listed October 7, 2026ResidentialSubdivision: Bucktown
Property Details

Beds & Baths

Total Bedrooms2
Total Bathrooms2
Full Baths2
Half Baths0
Total Rooms5

Size & Structure

Living Area0 sqft
Stories3
Lot SizeCOMMON

Location

CountyCook
TownshipWest Chicago
SubdivisionBucktown
Zip Code60614

Financial

List Price$475,000
Annual Taxes (2025)$6,441
Monthly Tax Est.$537
Parcel #14312130461005
Interior Features

Appliances

RangeMicrowaveDishwasherRefrigeratorWasherDryerDisposal

Flooring

Hardwood

Heating

Natural GasForced Air

Cooling

Central Air

Basement

None

Laundry

In UnitIn Bathroom
Exterior & Lot

Construction

Brick

Roof

Asphalt

Patio & Porch

Patio
Utilities & Parking

Sewer

Public Sewer

Water Source

Lake Michigan

Parking

AssignedOff AlleyYesOwned
HOA & Community
HOA Fee
$195
Monthly

HOA Includes

WaterInsuranceExterior MaintenanceScavengerSnow Removal
Tax & Financial
Annual Taxes
$6,441
Tax Year 2025
Monthly Tax Est.
$537
per month
Property Location

2042 Winchester Avenue, Chicago, IL 60614 — Cook County

$475,000
2042 Winchester Avenue
2 bd2 ba0 sqft
VL
Vittoria Logli
Top Glenview Agent

IL License 475.178467 · (847) 810-8438

Quick Facts
1 days on market
COMMON
$6,441/yr taxes
$195 HOA (monthly)
$3,228
estimated monthly payment
Principal & Interest
$2,496/mo
Property Tax
$537/mo
HOA
$195/mo
$475,000
20% — $95,000
3%50%
6.875%
3%12%
Loan Amount
$380,000
Down Payment
$95,000

* Estimated payment only. Actual rates, taxes, and insurance may vary. Contact a lender for a personalized quote.

Listed by
Redfin Corporation
Agent: Daniel Close
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