Home Homes for Sale Westport, CT 44 Pumpkin Hill Road

44 Pumpkin Hill Road, Westport, CT 06880

Single Family For Sale

$3,950,000
$561/sqft
44 Pumpkin Hill Road, Westport, CT Active
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5
Bedrooms
9
Bathrooms
7,040
Sq Ft
1.07
Acres
2005
Year Built

About This 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.

Listed by Christine Oleynick (203) 912-9712 with Keller Williams Realty (203) 429-4020

Listing Snapshot

Price $3,950,000 Days on Market 19 days
Property Tax $30,853/yr Style Colonial
Year Built 2005 Total Sq Ft 7,040
Lot Size 1.07 acres HOA Fees N/A
Bedrooms 5 Full Bathrooms 7
Total Rooms 16 Half Baths 2

Key Features

Interior
  • Auto Garage Door Opener
  • Cable - Available
Appliances
  • Gas Range
  • Microwave
  • Subzero
  • Washer
  • Dryer
  • Wine Chiller
Outdoor
  • Grill
  • Terrace
  • Garden Area
  • Lighting
  • Hot Tub
  • French Doors
  • Gunite
  • Heated
  • Spa
  • Safety Fence
  • In Ground Pool

Structure & Parking

Construction Frame,Masonry
Roof Asphalt Shingle
Garage Spaces 3
Garage Type Attached Garage

Systems & Utilities

Heat Hot Air
Fuel Oil
Cooling Central Air
Hot Water Oil, Domestic
Water Public Water Connected
Sewer Public Sewer Connected

Schools

Elem Long Lots
Middle Bedford
High Staples

Mortgage Calculator

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Est. Monthly Payment
Principal & Interest
Est. Property Tax $2,571/mo
Est. Home Insurance

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Mar 3, 2026 Listed $3,950,000

Frequently Asked Questions

How much does 44 Pumpkin Hill Road in Westport, CT cost?
This property is listed at $3,950,000, which works out to $561 per square foot.
How many bedrooms does 44 Pumpkin Hill Road have?
This home has 5 bedrooms and 9 bathrooms.
What is the square footage of 44 Pumpkin Hill Road?
The home is 7,040 square feet, situated on 1.07 acres.
When was 44 Pumpkin Hill Road in Westport built?
This property was built in 2005.
Is 44 Pumpkin Hill Road, Westport, CT still available?
The current MLS status of this property is "Active". Contact RYZE Realty Group for the latest availability.
What school district is 44 Pumpkin Hill Road, Westport in?
This home is served by the Westport public school system, with Long Lots as the elementary school and Staples as the high school.
How do I schedule a tour of 44 Pumpkin Hill Road, Westport, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Christine Oleynick · (203) 912-9712

Keller Williams Realty · (203) 429-4020

MLS# 24156956 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Mar 26, 2026 1:34 PM UTC