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44 Pumpkin Hill Road, 
Westport, CT 06880

$3,950,000


5

Beds


9

Baths


7,040

Sq Ft


Single Family

Coming Soon

Listed by

Christine Oleynick, (203) 912-9712

Keller Williams Realty, (203) 429-4020

Last updated:

March 5, 2026, 11:49 PM

MLS#

24156956

Source:

CT

About This Home

44 Pumpkin Hill Road

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.

Home Facts

Single Family

9 Baths

5 Bedrooms

Built in 2005

Price Summary

3,950,000

$561 per Sq. Ft.

MLS #:

24156956

Last Updated:

March 5, 2026, 11:49 PM

Added:

3 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

9

Full Bathrooms:

7

Interior

Living Area:

7,040 Sq. Ft.


Structure

Structure

Architectural Style:

Colonial

Building Area:

7,040 Sq. Ft.

Year Built:

2005


Lot

Lot Size (Sq. Ft):

46,609


Finances & Disclosures

Finances

Price:

$3,950,000

Price per Sq. Ft:

$561 per Sq. Ft.

Source:CT
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44 Pumpkin Hill Road
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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.