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For sale
    • $3,950,000

    44 Pumpkin Hill Road, Westport, CT 06880

    5beds
    7,040sqft
    : 
    Single Family Residence
    Built in 2005
    1.07 Acres Lot
    $-- Zestimate®
    $561/sqft
    $-- HOA

    What's special

    Set in one of Westport's most sought-after central neighborhoods, this gracious 5+ bedroom custom Colonial with a stunning gunite pool and spa offers the perfect balance of timeless elegance and modern comfort. Sun-filled interiors and thoughtful design create seamless flow for both entertaining and everyday living. The main level features a private office, elegant dining room with butler's pantry, and a living room with fireplace and French doors opening to the patios and park-like yard. The expansive white gourmet kitchen with quartzite counters, brand new Wolf double oven and gas cooktop, warming drawer, and SubZero refrigerator flows into a welcoming family room with floor-to-ceiling stone fireplace. A mudroom, three-car garage, and two powder rooms complete the level. Upstairs, the luxurious primary suite spans front-to-back with high ceilings, dressing area, generous closet, fireplace and spa bath. Four additional en-suite bedrooms, an upstairs family room, and dual staircases offer comfort and flexibility. The finished 3rd floor has 2 BR & bathroom and lower level provide exceptional additional space including a home theater, wine cellar, gym, and game room. Enjoy summer afternoons by the pool, evenings by the outdoor fireplace, and effortless al fresco dining under the stars and enjoy the new retractable awning. Designed for gathering, relaxing, and celebrating, this home offers year-round resort-style living.
    23 days
    |
    6,857
    |
    221
    |

    Zillow last checked: 7 hours ago

    Listing updated: 20 hours ago

    Listed by:

    Christine F. Oleynick (203)912-9712,

    Keller Williams Realty 203-429-4020

    Source: Smart MLS,MLS#: 24156956MLS Logo

    Tour with a local agent

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 9
      • Full bathrooms: 7
      • 1/2 bathrooms: 2
      Primary bedroom
      • Level: Upper
      Bedroom
      • Level: Upper
      Bedroom
      • Level: Upper
      Bedroom
      • Level: Upper
      Bedroom
      • Level: Upper
      Dining room
      • Level: Main
      Family room
      • Level: Third,Upper
      Kitchen
      • Features: High Ceilings, Built-in Features, Dining Area, Fireplace, Kitchen Island, Hardwood Floor
      • Level: Main
      Living room
      • Level: Main
      Media room
      • Level: Lower
      Office
      • Level: Main
      Other
      • Features: Full Bath
      • Level: Third,Upper
      Other
      • Level: Third,Upper
      Rec play room
      • Level: Lower
      Heating
      • Forced Air, Oil
      Cooling
      • Central Air
      Appliances
      • Included: Gas Range, Microwave, Subzero, Washer, Dryer, Wine Cooler, Water Heater
      Features
      • Doors: French Doors
      • Basement: Full,Heated,Storage Space,Cooled,Interior Entry,Walk-Out Access
      • Attic: Finished
      • Number of fireplaces: 4
      Interior area
      • Total structure area: 7,040
      • Total interior livable area: 7,040 sqft
      • Finished area above ground: 7,040

      Property

      Parking
      • Total spaces: 3
      • Parking features: Attached, Garage Door Opener
      • Attached garage spaces: 3
      Features
      • Patio & porch: Terrace
      • Exterior features: Outdoor Grill, Garden, Lighting
      • Has private pool: Yes
      • Pool features: Gunite, Heated, Pool/Spa Combo, Fenced, In Ground
      • Spa features: Heated
      • Waterfront features: Beach Access, Water Community
      Lot
      • Size: 1.07 Acres
      • Features: Level
      Details
      • Parcel number: 412674
      • Zoning: AA

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial
      • Property subtype: Single Family Residence
      Materials
      • Clapboard
      • Foundation: Concrete Perimeter, Masonry
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 2005

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Cable Available

      Community & HOA

      Community
      • Subdivision: Long Lots
      HOA
      • Has HOA: No
      Location
      • Region: Westport

      Financial & listing details

      • Price per square foot: $561/sqft
      • Tax assessed value: $1,635,900
      • Annual tax amount: $30,853
      • Date on market: 3/3/2026
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        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        Price history
        DateEventPrice
        3/7/2026Listed for sale$3,950,000+16.2%$561/sqft
        Source: Smart MLS #24156956 Report a problem
        5/29/2024Sold$3,400,000-2.8%$483/sqft
        Source: Smart MLS #24008845 Report a problem
        4/30/2024Pending sale$3,499,000$497/sqft
        Source: Smart MLS #24008845 Report a problem
        4/11/2024Listed for sale$3,499,000$497/sqft
        Source: Smart MLS #24008845 Report a problem
        12/15/2023Listing removed--
        Source: Smart MLS #170604264 Report a problem
        10/19/2023Listed for sale$3,499,000+37.9%$497/sqft
        Source: Smart MLS #170604264 Report a problem
        1/16/2018Sold$2,537,500-16.8%$360/sqft
        Source: Smart MLS #99180436 Report a problem
        4/5/2006Sold$3,049,000+158.4%$433/sqft
        Source: Smart MLS #98267533 Report a problem
        5/17/2005Sold$1,180,000+33.3%$168/sqft
        Source: Public Record Report a problem
        9/5/2001Sold$885,000+7.9%$126/sqft
        Source: Public Record Report a problem
        7/14/2000Sold$820,000$116/sqft
        Source: Public Record Report a problem

        Public tax history

        Public tax history
        YearProperty taxesTax assessment
        2025$30,853 +1.3%$1,635,900
        2024$30,460 +1.5%$1,635,900
        2023$30,019 +1.5%$1,635,900
        2022$29,561 $1,635,900
        2021$29,561 -1.8%$1,635,900 -9.1%
        2020$30,088 -0.9%$1,800,600
        2019$30,358 $1,800,600
        2018$30,358 $1,800,600
        2017$30,358 $1,800,600
        2016$30,358 $1,800,600

        Find assessor info on the county website

        BuyAbility℠ payment

        Est. payment
        $26,282/mo
        Principal & interest
        $20719
        Property taxes
        $5563
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          Climate risks

          Neighborhood: Staples

          Getting around

          1 / 100
          Car-Dependent
          24 / 100
          Somewhat Bikeable

          Nearby schools

          GreatSchools rating
          Schools provided by the listing agent
          • Elementary: Long Lots
          • Middle: Bedford
          • High: Staples

          Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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