44 Pumpkin Hill Rd Westport, CT, 06880

single family home
$ 3,950,000 For Sale Coming Soon Mar 3, 2026
  • 5 beds
  • 9 baths
  • 7,040 sq ft
  • 1.07 acres
  • 2005 year built
  • in ground pool
  • 3 cars garage

About the Home

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.

Rooms & Interior

5 bedrooms beds
7 full + 2 half baths
7,040 square feet sq ft

Room Details

  • Living Room (Main Level)
  • Dining Room (Main Level)
  • Eat In Kitchen (Main Level) 9 ft+ Ceilings, Built-Ins, Dining Area, Fireplace, Island, Hardwood Floor
  • Office (Main Level)
  • Media Room (Lower Level)
  • Other (Upper Level) Full Bath, On 3rd Floor
  • Family Room (Upper Level) On 3rd Floor
  • Bedroom (Upper Level)
  • Bedroom (Upper Level)
  • Bedroom (Upper Level)
  • Rec/Play Room (Lower Level)
  • Other (Upper Level) On 3rd Floor
  • Primary Br Suite (Upper Level)
  • Bedroom (Upper Level)

Home Features

Heating

  • Fireplaces: 4
  • Heating: hot air
  • Heat fuel type: oil
  • Fuel tank: in basement

Cooling

  • Central air

Interior Features

  • Auto garage door opener
  • Cable - available

Appliances

  • Gas range
  • Microwave
  • Subzero
  • Washer
  • Dryer
  • Wine chiller

Attic

  • Finished
  • Walk-in

Basement

  • Full
  • Heated
  • Storage
  • Cooled
  • Interior access
  • Walk-out
  • Full with walk-out

Exterior Features

  • Grill
  • Terrace
  • Garden area
  • Lighting
  • Hot tub
  • French doors

Property Details

Parking

  • Garage spaces: 3
  • Attached garage

Swimming Pool

  • Gunite
  • Heated
  • Spa
  • Safety fence
  • In ground pool

Waterfront

  • Beach rights
  • Water community
Waterfront Homes in Westport

Lot Details

  • Lot surface: 1.07 acres
  • Level lot

Utilities

  • Water: public water connected
  • Sewage: pub. sewer connected

Construction Details

Style
colonial

Construction year
2005

Exterior Siding
clapboard

Foundation
concrete, masonry

Roof
asphalt shingle


Area & Town

This home is located in Roseville/North Avenue neighborhood, in the town of Westport.

Finance & Listing Info

Status Coming soon
Listing date March 03, 2026
List price $ 3,950,000
Current price $ 3,950,000
Tax amount $ 30,853
Tax year july 2025-june 2026
MLS ID #24156956
List Agent Christine Oleynick
List Office Keller Williams Realty

44 Pumpkin Hill Road Home Photos

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