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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.
Listed by The Beach Buoys of Gibson Sotheby's International Realty (508-296-5459)

More Info

Location Information

  • 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.

Basic Information

  • Parcel Number 113710
  • Road Frontage DescriptionPaved

Tax Information

  • Tax Assessed Value $1,789,400
  • Tax Year 2025
  • Taxes$13,578

Parking

  • Parking Spaces9

Rooms

  • Bathroom8
  • Bathrooms Total Decimal 8
  • Bedrooms10
  • Full Bath8

Basic Information

  • List Price$2,450,000
  • MLS Number22404793
  • Modification Date05/05/2025
  • Property SubTypeSingle Family Residence

Location

  • Address6 Winslow Street
  • Building Number6
  • CountyBarnstable
  • StateMA
  • StreetWinslow Street
  • TownProvincetown
  • Zip02657

Building

  • BasementCrawl Space
  • Building Area Units Square Feet
  • Construction Materials Shingle Siding
  • Fireplace YN Yes
  • Fireplaces Total 1
  • FoundationSlab
  • Rooms14
  • Year Built1810

Property

  • Acreage0.07

Interior

  • Flooring Hardwood, Carpet, Wood

Exterior

  • Exterior Features Garden
  • RoofShingle

Utilities

  • Cooling YN Yes
  • Heating YN Yes
  • Sewer Public Sewer

Property Information

  • Living Area Units Square Feet
  • Lot Size Square Feet 3,049
  • Lot Size Units Acres
  • Property Condition Approximate
  • Square Feet2,124

Amenities

  • Appliances IncludedWater Heater, Electric Water Heater
  • Other AmenitiesBasement, Fireplace, Garden

Other

  • Date Listed09/30/2024
  • Special Listing Conditions Standard
  • View Count4

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This site was last updated May 23, 2025 9:52 AM EDT. All properties are subject to prior sale, changes, or withdrawal.

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