Nestled on a charming side street in the heart of Provincetown, this delightful 10-bedroom 8 bathroom property, currently operating as the popular Chicago House guesthouse, is a hidden gem. The main level boasts a delightful parlor room, a fully renovated kitchen, and the owner's quarters complete with a private bath. There are two beautifully appointed guests rooms, each featuring its own private bath. On the second level, you'll find seven inviting guest rooms, serviced by four private and three shared baths. Guests love the covered porch--a perfect spot for sipping morning coffee or unwinding with an afternoon cocktail while soaking in the vibrant atmosphere of the town. A standout feature of this property is the ability to accommodate nine parking spaces, a rare find in such a central location! Additionally, solar panels are installed, generating enough electricity to nearly eliminate the electric bill. With over 2,100 square feet of living space and soon-to-be connection to the sewer for 10 bedrooms, this property presents endless possibilities for its next owner, whether you're looking to continue its successful guesthouse operation or explore new ventures. Reviews highlight the warm hospitality and personalized service that make each stay special. Guests often rave about the peaceful ambiance, impeccable cleanliness, and the delightful breakfast offerings. Many visitors return year after year, drawn by the sense of home and the exceptional experiences shared at The Chicago House. Whether you're seeking a romantic getaway, a family vacation, or a solo retreat, The Chicago House Guesthouse offers an unforgettable experience that captures the essence of Provincetown's charm and history. Seller welcomes offers with requests for buyer concessions.
For sale
Price cut: $100K (9/15)
$2,350,000
6 Winslow Street, Provincetown, MA 02657
10beds
2,124sqft
Est.:
Single Family Residence
Built in 1810
3,049.2 Square Feet Lot
$-- Zestimate®
$1,106/sqft
$-- HOA
What's special
Covered porchPrivate bathDelightful parlor roomNine parking spacesCharming side streetFully renovated kitchen
- 440 days |
- 425 |
- 9 |
Zillow last checked: 8 hours ago
Listing updated: September 16, 2025 at 04:58am
Listed by:
The Beach Buoys 508-296-5459,
Gibson Sotheby's International Realty
Source: CCIMLS,MLS#: 22404793
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 10
- Bathrooms: 8
- Full bathrooms: 8
Heating
- Has Heating (Unspecified Type)
Cooling
- Has cooling: Yes
Appliances
- Included: Electric Water Heater
Features
- Flooring: Hardwood, Carpet, Wood
- Basement: Crawl Space
- Number of fireplaces: 1
Interior area
- Total structure area: 2,124
- Total interior livable area: 2,124 sqft
Property
Parking
- Total spaces: 9
Features
- Stories: 2
- Patio & porch: Porch
- Exterior features: Garden
Lot
- Size: 3,049.2 Square Feet
Details
- Parcel number: 113710
- Zoning: R3
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape Cod
- Property subtype: Single Family Residence
Materials
- Shingle Siding
- Foundation: Slab
- Roof: Shingle
Condition
- Approximate
- New construction: No
- Year built: 1810
Utilities & green energy
- Sewer: Public Sewer
Community & HOA
HOA
- Has HOA: No
Location
- Region: Provincetown
Financial & listing details
- Price per square foot: $1,106/sqft
- Tax assessed value: $1,789,400
- Annual tax amount: $13,578
- Date on market: 9/30/2024
- Cumulative days on market: 440 days
- Road surface type: Paved
Estimated market value
Not available
Estimated sales range
Not available
$3,886/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 9/15/2025 | Price change | $2,350,000-4.1%$1,106/sqft |
Source: | ||
| 1/13/2025 | Price change | $2,450,000-5.8%$1,153/sqft |
Source: | ||
| 9/30/2024 | Listed for sale | $2,600,000+184.2%$1,224/sqft |
Source: | ||
| 6/21/2016 | Sold | $915,000+139.2%$431/sqft |
Source: CCIMLS #21511268 Report a problem | ||
| 9/18/2001 | Sold | $382,500+24.4%$180/sqft |
Source: Public Record Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $1,789,400 +23.2% |
| 2024 | -- | $1,452,200 +22.1% |
| 2023 | -- | $1,189,800 +21.4% |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$14,047/mo
Principal & interest
$11971
Property taxes
$1253
Home insurance
$823
Climate risks
Neighborhood: 02657
Nearby schools
GreatSchools rating
- 3/10Provincetown SchoolsGrades: PK-8Distance: 0.1 mi
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