
209 S Prospect Street, GALENA, IL 61036
Jo Daviess County
Key Facts
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
Heating
Basement
Construction
Roof
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
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
Nearby Homes
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Similar Home Values
Comparable nearby listings and their asking prices.
| Address | Price | Beds | Baths | Sq Ft |
|---|---|---|---|---|
| 7 Seneca Trail, GALENA, IL | $749,900 | 5 | — | 4,096 |
| 3 Laurel Court, GALENA, IL | $769,000 | 5 | — | 3,435 |
| 1004 Park Avenue, GALENA, IL | $895,000 | 8 | — | 5,152 |
| 5 Blue Ridge Court, GALENA, IL | $995,000 | 5 | — | 3,016 |
| 8 Trillium Lane, Galena, IL | $1,069,000 | 6 | — | 5,022 |
| 8 Trillium Lane, GALENA, IL | $1,069,000 | 6 | — | 5,022 |
Moving Cost Estimate
EXIT Agents in GALENA
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