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For sale
  • Price cut: $100K (9/15)
    $2,350,000

    6 Winslow Street, Provincetown, MA 02657

    10beds
    2,124sqft
    : 
    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
    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.
    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#: 22404793MLS Logo

    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
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    Estimated market value

    Not available

    Estimated sales range

    Not available

    $3,886/mo

    Price history

    Price history
    DateEventPrice
    9/15/2025Price change$2,350,000-4.1%$1,106/sqft
    Source: CCIMLS #22404793 Report a problem
    1/13/2025Price change$2,450,000-5.8%$1,153/sqft
    Source: CCIMLS #22404793 Report a problem
    9/30/2024Listed for sale$2,600,000+184.2%$1,224/sqft
    Source: CCIMLS #22404793 Report a problem
    6/21/2016Sold$915,000+139.2%$431/sqft
    Source: CCIMLS #21511268 Report a problem
    9/18/2001Sold$382,500+24.4%$180/sqft
    Source: Public Record Report a problem

    Public tax history

    Public tax history
    YearProperty taxesTax 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
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