44 Pumpkin Hill Road
Westport, CT, 06880 $ 3,950,000
Bedrooms5 Baths7.2 Sq 7,040 Monthly Estimate*
$ 24,321
for $3,950,000 with 5 bedrooms and 7 full baths, 2 half baths. This 7,040 square foot home was built in 2005 on a lot size of 1.07.
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.
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Single Family Coming Soon
FeaturesGeneralZoning AA
Neighborhood Long Lots
County Fairfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Coming Soon
Acres 1.07
Directions Per GPS
High School Staples
City Westport
Elementary School Long Lots
Sq Ft Total 7040
Year Built 2005
Style Colonial
Year Built Source Public Records
Pool Description Gunite Heated Spa Safety Fence In Ground Pool
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InteriorCooling System Central Air
Total Rooms 16
Basement Description Full Heated Storage Cooled Interior Access Walk-out Full With Walk-Out
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ExteriorWater Source Public Water Connected
Lot Description Level Lot
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* Excluded FeaturesList ByChristine OleynickListing Agent
Keller Williams RealtyBroker
Affordability Calculator
- Monthly Principal & Interest
- $24,321
- Monthly Property Taxes
- $2,571
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Westport, CT
Average List Price $3,837,590
Percent of Sale Price 3%
About Westport, CT 26,742 Population
4% Since 2002
$ 169,979 Median Income
48.33 Median Age
40% Households with Children
Trends Information provided by ATTOM Data Solutions.
3041933 Elementary School
1967866 Middle School
Staples High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 3/3/2026 | $3,950,000 | | Listed Price |