$3,950,000

44 Pumpkin Hill Road, Westport, CT 06880

  • 5 beds |
  • 9 baths |
  • 7,040 sqft
  • Property Icon Single-Family Home
  • Property Year Built Icon Built in 2005
  • Property Lot Size Icon1.07acre lot
  • Property Parking Icon 3 car garage
  • Property Price Per Square Feet Icon $561/sqft
  • Property List Date Icon Listed 24 days ago

Property Description

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.

Listing Status:
Active
Date Added:
March 3, 2026
Data Last Updated:
March 27, 2026 at 4:50PM
Listing Office:
Keller Williams Realty : (203) 429-4020
Listing Agent:
Christine Oleynick : (203) 912-9712
MLS ID:
24156956
  • General: Auto Garage Door OpenerCable - Available
  • Appliances: Gas RangeMicrowaveSubzeroWasherDryerWine Chiller
  • Basement: FullHeatedStorageCooledInterior AccessWalk-outFull With Walk-Out
  • A/C: Central Air
  • Heating: Hot AirOil
  • Fireplace: Fireplaces: 4
  • General: GrillTerraceGarden AreaLightingHot TubFrench Doors
  • Style: Colonial
  • Pool: GuniteHeatedSpaSafety FenceIn Ground Pool
  • Roofing: Asphalt Shingle
  • County: Fairfield
  • Zoning: AA412674
  • Water: Public Water Connected
  • Sewer: Public Sewer Connected

This listing courtesy of Christine Oleynick , Keller Williams Realty

Monthly Payment

$Est. Payment
  • Principal & Interest $
  • Property Taxes $
  • Home Insurance $
  • VA Funding Fee $

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Location

Schools Nearby

L

Long Lots Elementary School

13 Hyde Ln, Westport, CT, 06880

Grades KG-5

1.50 miles away

B

Bedford Middle School

88 North Ave, Westport, CT, 06880

Grades 6-8

0.54 miles away

S

Staples High School

70 North Ave, Westport, CT, 06880

Grades 9-12

0.61 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.

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