#22304001, The Beach Buoys, Listing Office: Gibson Sothebys International Realty
6 Winslow St Provincetown, MA 02657
Property details
About 6 Winslow St
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.
Highlights
Summary
- Full Bathrooms: 8
- Appliances: Water Heater, Electric Water Heater
- Flooring Type: Hardwood, Carpet, Wood
- Total Bedroom Count: 10
- Exterior: Garden, Porch
- Architectural Style: Cape
- Heating: Forced Air
- Cooling: Wall Unit(s)
- List Price: $2,450,000
- Annual Tax Amount: $7,238
- Tax Year: 2024
- Directions: Bradford Street to 6 Winslow, Chicago House. or Webster Place to the end toward the right which will bring you to the 9 parking spaces in the back of The Chicago House.
- Year Built: 1810
- Stories: 2
- Lot Size: 0.07 Acres
- MLS Number: 22404793
- MLS Name: CapeCod
- Office Name: Gibson Sothebys International Realty
- Office Phone: (508) 487-2430
- Listing Agent: The Beach Buoys
The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. (CCIMLS). Real estate listings provided by CCIMLS and held by other brokerage firms are marked with the CCIMLS BR Logo and detailed information includes, at minimum, the name of the listing agent and broker attribution assigned by the listing broker. Neither the listing broker nor this broker shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. All properties are subject to prior sale, changes, or withdrawal. The Broker providing this data believes it to be correct but advises interested parties to confirm any item before relying on it in a purchase decision.
Copyright 2025© Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 5/5/2025, 3:01:00 AM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
Get an agent. Get a mortgage. Save big.¹

$2,450,000
6 Winslow St
$10,000
closing credit¹
Sell your home with Rocket and save even more!
Seller rebate
0.5% sale price²
Price information
Property sales
Date | Event | Price |
---|---|---|
Jun 21, 2016 | Home Sold | $915,000 |
Sep 18, 2001 | Home Sold | $382,500 |
Jun 28, 1999 | Home Sold | $307,500 |
Sep 21, 1988 | Home Sold | $237,000 |
Tax history
Year | Assessment | Property Tax |
---|---|---|
2024 | $1,452,200 | $7,238 |
2023 | $1,189,800 | $7,238 |
2022 | $1,023,100 | $7,238 |
2021 | $979,700 | $7,238 |
2019 | $959,300 | $- |
History based on county public records data.
Nearby schools
6
Eastham Elementary School
Public District PK-5
18.2 mi
•200 School House Rd
8
Manomet Elementary School
Public District KG-5
20.8 mi
•70 Manomet Point Rd
5
Eddy Elementary School
Public District 3-5
20.9 mi
•2298 Main St
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $46,538. Most Provincetown, MA residents have annual incomes less than $<35k. The majority of families are single, no kids. Typical level of education for residents in this area is post secondary degree.
Similar homes for sale
Frequently asked questions
About 6 Winslow St
The listing price of 6 Winslow St property is $2,450,000.
The property 6 Winslow St is a house located in Provincetown, Massachusetts, 02657.
Active Listing: 6 Winslow St is For Sale (Active/New) which means the seller is accepting offers.
The nearby schools for 6 Winslow St are: Eastham Elementary School (GreatSchools Rating 6/10), Manomet Elementary School (GreatSchools Rating 8/10), Eddy Elementary School (GreatSchools Rating 5/10), Provincetown IB School (GreatSchools Rating 6/10), Nauset Regional Middle School (GreatSchools Rating 4/10), Plymouth South Middle School (GreatSchools Rating 5/10), Nauset Regional High School (GreatSchools Rating 6/10), Cape Cod Region Vocational Technical (GreatSchools Rating 7/10), Plymouth South High School (GreatSchools Rating 4/10).
According to the records, the last property tax for 2024 is $7,238 (source: MLS/based on county public records data).
The last sale was on June 21, 2016 for $915,000 (source: MLS/tax record).
The property at 6 Winslow St has 10 bedrooms and 8 bathrooms.
The year of construction for 6 Winslow St is 1810.
This home is located at 6 Winslow St in Provincetown, MA and zip code 02657. Features: 10 bedrooms, 8 bathrooms. It has been listed on Rocket Homes since January 23, 2025 and is currently priced at $2,450,000.
In April 2025 more than 0 listings in Provincetown, MA were sold above the asking price. During the same period more than 1 listings were sold at asking price, while more than 14 were sold below. The number of listings in Provincetown, MA increased by 4.3% between March and April 2025. While the average time on the market in April 2025 was 85 days, the median list price was $1,250,000.