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209 S Prospect Street, GALENA, IL 61036

Jo Daviess County

Key Facts

6Beds
2,304Sq Ft
1900Year Built
2Stories

Description

Rare opportunity to own one of Galena's most iconic historic properties, offering the perfect blend of owner occupancy, investment potential, and an exceedingly scarce City of Galena short-term rental license, all perched high atop prestigious Quality Hill with some of the most breathtaking panoramic views in town. Built by Asa Haile, a licensed riverboat captain and accomplished mason, this stately Federal-style brick duplex with elegant Greek Revival influences has remained in the same family since the 1970s, lovingly passed from one generation to the next, and now presents a once-in-a-generation opportunity for its next steward. Encompassing over 4,500 square feet between two beautifully maintained residences, the property offers exceptional flexibility with one side licensed and successfully operated as a highly coveted City of Galena short-term rental (licensed for four-person occupancy), while the adjoining residence is ideal for owner occupancy or long-term rental income. The licensed vacation rental features three bedrooms, three full baths, a nicely appointed kitchen, spacious dining area perfect for entertaining, inviting living room centered around a cozy wood stove, private paver patio, and expansive windows that perfectly frame the spectacular vistas beyond. The owner's residence offers an updated kitchen, generous living room overlooking the incredible scenery, dining area, three bedrooms, three baths, convenient upper-level laundry/mudroom, and private aggregate patio. Rich with character throughout, both residences showcase remarkable historic craftsmanship including gorgeous original woodwork, period built-ins, wide-plank wood flooring, handsome decorative fireplaces, soaring ceilings, oversized windows, and countless architectural details that celebrate the home's enduring heritage. While the home's rich history and architectural details are extraordinary, it is the expansive covered front porch that truly defines the experience of living here, offering a front-row seat to one of the most spectacular vistas in Galena. Whether enjoying a quiet morning coffee as the town awakens below, relaxing as the sun sets beyond Grant's Home and Horseshoe Mound, or taking in the twinkling lights of historic Main Street and the Park Avenue skyline after dusk, the ever-changing views create an unforgettable backdrop in every season. Few homes in Galena command a setting of this caliber, where sweeping panoramas stretch across the city's historic rooftops and church steeples to the rolling hills and scenic countryside beyond. Additional amenities include separate attic spaces above each residence, individual basement/cellar areas, an attached one-car open garage/carport, and a convenient pass-through storage shed providing easy rear access to both residences. Located just moments from Galena's renowned shopping, dining, entertainment, festivals, and historic attractions, this extraordinary property combines architectural significance, irreplaceable views, remarkable flexibility, and income potential into one exceptional offering. Whether you're seeking a legacy residence with supplemental income, a premier investment property, or an iconic piece of Galena history, 209/211 S. Prospect Street represents an opportunity that rarely comes to market and may not be seen again for another generation.

Property Information

Property Type

Residential Income

Sub-Type

Duplex

Style

2 Story

Year Built

1900

Stories

2

Living Area

2,304 sq ft

Parking Spaces

1

Days on Market

5

MLS® Listing#

202604033

Property Features

Appliances

DishwasherDryerMicrowaveRefrigeratorWasherGas Water Heater

Heating

Baseboard

Basement

Sump PumpPartial

Construction

Brick

Roof

Shingle

Schools

Elementary:
Galena
Middle:
Galena
High:
Galena
District:
Galena

Financial Details

Annual Taxes

$9,230

Tax year 2025

Parcel Number

2210058600

Affordability Calculator

$170,000

Estimated monthly payment

$4,524/mo

Principal $680,000 · Est. interest $948,661 over 30 yrs

Neighborhood Market Statistics

How this home compares to active listings in GALENA, IL

$364,151
Median Listing Price
82
Median Days on Market
1,972
Median Sq Ft
$199
Median Price / Sq Ft
117
Active Listings
  • This home’s price is 133% above the area median.
  • Its price per sq ft is 85% above the area median.

Market statistics compiled from active EXIT Realty® and MLS listings in GALENA, IL.

Location

Map showing the location of 209 S Prospect Street, GALENA, IL 61036

Points of Interest in GALENA, IL

Showing the GALENA area map.

Nearby Schools

  • Galena Primary School

    Elementary · 0.8 mi away

  • Galena High School

    Secondary · 0.8 mi away

  • Galena Unit School District #120

    School · 0.9 mi away

  • Galena Middle School

    Elementary · 1.0 mi away

  • Tri-State Christian School

    Secondary · 1.4 mi away

  • Nativity of BVM School

    School · 7.2 mi away

  • Southwestern Wisconsin High

    Elementary · 8.0 mi away

  • St Joseph's School

    School · 9.5 mi away

  • Scales Mound High School

    Secondary · 10.1 mi away

  • Benton School District

    Secondary · 10.7 mi away

  • Marquette High School

    Secondary · 10.8 mi away

  • River Ridge Elementary School

    Secondary · 10.9 mi away

  • Bellevue Elementary School

    Elementary · 11.0 mi away

  • Bellevue High School

    Secondary · 11.2 mi away

  • East Dubuque High School

    Secondary · 11.4 mi away

  • St Mary's School

    Elementary · 11.7 mi away

  • East Dubuque Elementary School

    Elementary · 11.9 mi away

  • Cuba City School District

    School · 13.1 mi away

  • Cuba City High School

    Secondary · 13.1 mi away

  • Central Alternative High School

    Secondary · 13.2 mi away

Commute Calculator

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Nearby Homes

Similar Homes Nearby

Similar Home Values

Comparable nearby listings and their asking prices.

AddressPriceBedsBathsSq Ft
7 Seneca Trail, GALENA, IL$749,90054,096
3 Laurel Court, GALENA, IL$769,00053,435
1004 Park Avenue, GALENA, IL$895,00085,152
5 Blue Ridge Court, GALENA, IL$995,00053,016
8 Trillium Lane, Galena, IL$1,069,00065,022
8 Trillium Lane, GALENA, IL$1,069,00065,022

Moving Cost Estimate

EXIT Agents in GALENA

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The data relating to real estate for sale on this website comes in part from the Internet Data exchange (IDX) program of the NorthWest Illinois Alliance of REALTORS®. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Real estate listings held by brokerage firms other than EXIT Realty, are indicated by detailed information about them such as the name of the listing firms. Information deemed reliable but not guaranteed. Copyright ©2026 NorthWest Illinois Alliance of REALTORS®. All Rights Reserved.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (IDX) program of one or more Multiple Listing Services (MLS). Listing information is deemed reliable but is not guaranteed accurate. Copyright © EXIT Realty® and respective MLS providers.

Data provided by RockfordIL. MLS® Listing#202604033. © 2026EXIT Realty®. All rights reserved.