Winslow Street

Provincetown | Massachusetts

The Ultimate

Private Retreat

View Photos Watch Film 360° VTour Open House

Devin Coutu

Presented At

$2,350,000

Bedrooms

Bathrooms

Living

2,124

SQFT

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 1

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 2

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 3

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 4

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 5

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 6

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 7

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 8

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 9

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 10

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 11

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 12

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 13

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 14

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 15

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 16

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 17

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 18

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 19

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 20

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 21

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 22

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 23

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 24

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 25

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 26

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 27

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 28

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 29

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 30

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 31

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 32

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 33

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 34

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 35

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 36

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 37

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 38

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 39

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 40

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 41

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 42

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 43

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 44

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 45

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 46

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 47

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 48

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 49

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 50

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. - Photo 51

Winslow Street

Provincetown | Massachusetts

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States. , Provincetown , Massachusetts

Guesthouse With Parking & Solar In The Heart Of Provincetown

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.

Gallery

3D Street View Tour

Property Location

6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States., Provincetown Massachusetts

Local Weather & Climate

Provincetown, Massachusetts

Current Conditions Updated recently

27 °F

Clear sky

Feels Like 21°F

Humidity 93%

Wind 5 mph

Visibility 6.2 mi

Sunrise 11:29 AM

Sunset 10:19 PM

5-Day Forecast

Fri 20 Feb

Clouds

High 36°

Low 30°

Sat 21 Feb

Snow

High 36°

Low 32°

Sun 22 Feb

Clouds

High 36°

Low 32°

Mon 23 Feb

Snow

High 36°

Low 32°

Tue 24 Feb

Clouds

High 33°

Low 28°

Data from OpenWeatherMap

Walkability & Transit Scores

How easy is it to get around Provincetown?

Walkability and transit scores for this address come from the EPA National Walkability Index.

Mortgage Calculator

Estimate your monthly payments for this property

Home Price

Down Payment

$100,000

Interest Rate

Loan Term

Estimated Monthly Payment $3,160

Monthly Payment Breakdown

Principal & Interest $2,528

Loan Amount $400,000

Total Interest $337,621

Total Cost $737,621

Potential Tax Benefits (United States)

$0 Est. First Year Interest Deduction

$0 Est. Annual Tax Savings

*Based on post-2017 tax law. Actual deductions depend on filing status, itemization, and current tax laws.

Ready to explore financing?

Connect with trusted mortgage partners

Important Information

This calculator is for illustrative purposes only and does not constitute a loan offer, pre-approval, or commitment to lend.
Monthly payment estimates do not include property taxes, homeowner's insurance, HOA fees, or other applicable costs which may significantly increase your actual payment.
Interest rates shown are for demonstration only. Actual rates depend on your credit score, down payment, loan type, property location, and current market conditions.
This tool provides estimates only. Consult with a licensed mortgage professional for accurate quotes and personalized advice.
Tax benefit calculations are simplified estimates based on general assumptions for United States. Actual deductions depend on your specific tax situation, filing status, and current tax laws.
Tax Year Information: Tax data shown is based on United States tax year 2025 (fiscal year: January-December), rules effective from 2018 through 2025. Tax laws change frequently and may have been amended since this data was compiled.

Tax Information Disclaimer

The tax benefit information displayed on this page is provided for general informational and educational purposes only. This information:

Does not constitute tax advice and should not be relied upon as such. Tax laws are complex and vary by jurisdiction, individual circumstances, and are subject to change without notice.
May not be current or accurate for your specific situation. Tax rules are updated frequently by governments, and the information shown may not reflect the most recent changes.
Uses simplified assumptions that may not apply to your circumstances, including filing status, total income, other deductions, alternative minimum tax considerations, and local tax variations.
Should not be used as the basis for any tax planning decisions or financial strategies without consulting a qualified tax professional licensed in your jurisdiction.

Before making any decisions based on potential tax benefits, you should consult with a qualified tax advisor, certified public accountant (CPA), or licensed tax professional who can evaluate your specific circumstances and provide advice tailored to your situation.

Limitation of Liability: By using this calculator, you acknowledge that all results are approximations and should not be relied upon for financial, legal, or tax decisions. openluxe, its affiliates, officers, directors, employees, and agents expressly disclaim all liability for any damages, losses, or consequences arising from the use of or reliance on this calculator or the information provided herein. openluxe is not a lender, financial advisor, or tax professional and does not provide mortgage loans, financial advice, or tax advice. Use of this calculator does not create any professional relationship.

Frequently Asked Questions

Common questions about this property

How many bedrooms and bathrooms does 6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States have?

This house at 6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States features 10 bedrooms with 2,124 square feet of living space.

What is the size of 6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States?

This property offers 2,124 square feet of living space.

What is the listing price for 6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States?

This property is listed at $235,000,000, which equals $110640 per square foot.

What type of property is 6 Winslow Street , Provincetown, MA 02657, Provincetown, Massachusetts, United States?

This is a house located in Provincetown, Massachusetts. The property is situated in an established neighborhood with convenient access to local amenities and services.

Brokerage: