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$3,950,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 7 Full Baths
  • 2 Partial Baths
  • 7,040 Sq. Ft.
  • 3 Car Garage
  • Updated 2 hours ago

Next open house:

Open House: 2:00 PM - 4:00 PM

Sunday 3/8 2:00 PM - 4:00 PM

44 Pumpkin Hill Road,Westport, CT 06880

44 Pumpkin Hill RoadWestportCT06880

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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.

Full Property Details for 44 Pumpkin Hill Rd

General

  • Price: $3,950,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24156956
  • Updated: Today (3/7/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 16
  • Interior Features: Auto Garage Door Opener, Cable - Available
  • Fireplace: Yes
  • Number of Fireplaces: 4
  • Appliances: Gas Range, Microwave, Subzero, Washer, Dryer, Wine Chiller

Rooms

Bathrooms

  • Total Bathrooms: 9
  • Full Bathrooms: 7
  • Half Bathrooms: 2

Bedrooms

  • Total Bedrooms: 5
  • Primary Suite: Upper
  • Bedroom 1: Bedroom, Upper
  • Bedroom 2: Bedroom, Upper
  • Bedroom 3: Bedroom, Upper
  • Bedroom 4: Bedroom, Upper

Other Rooms

  • Living Room: Living Room, Main
  • Family Room: Family Room - On 3rd Floor, Upper
  • Eat In Kitchen: Eat-In Kitchen - 9 ft+ Ceilings, Built-Ins, Dining Area, Fireplace, Island, Hard, Main
  • Dining Room: Dining Room, Main
  • Office: Office, Main
  • Game room: Yes
  • Game Room: Rec/Play Room, Lower
  • Rec Room: Lower
  • Theater/Media: Media Room, Lower
  • Other Room 1: Other - Full Bath, On 3rd Floor, Upper
  • Other Room 2: Other - On 3rd Floor, Upper

Additional Information

  • Pool: Yes
  • Pool Description: Gunite, Heated, Spa, Safety Fence, In Ground Pool

Exterior

  • Exterior Features: Grill, Terrace, Garden Area, Lighting, Hot Tub, French Doors
  • Color: White

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Parking: Attached Garage

Location

  • County: Fairfield
  • Neighborhood: Long Lots
  • Driving Directions: Per GPS

School Information

  • Elementary School: Long Lots
  • Middle School: Bedford
  • High School: Staples

Community

  • Community Name: Long Lots

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Oil
  • Heating Fuel: Oil
  • Water Heater: Oil, Domestic

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard
  • Basement Desc.: Full, Heated, Storage, Cooled, Interior Access, Walk-out, Full With Walk-Out
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 7,040
  • Above Ground: 7,040 Sq. Ft.
  • Year Built: 2005

Lot Features

  • Lot Size (Acres): 1.07
  • Zoning: AA
  • Lot Description: Level Lot

Water Features

  • Water Front Desc.: Beach Rights, Water Community

Financial Considerations

  • Assessment Amount: $1,635,900
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 412674

Listed by Keller Williams Realty, Christine Oleynick

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Listing agent

— 44 Pumpkin Hill Rd —

  • Christine Oleynick

    Keller Williams Realty

Agent Contact: (203) 912-9712 Office Contact: (203) 429-4020

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 44 Pumpkin Hill Rd

School District:Westport School District
NameGradesDistance
Long Lots School
13 Hyde Lane, Westport, CT 06880
K-51.5 mi
Bedford Middle School
88 North Avenue, Westport, CT 06880
6-80.5 mi
Staples High School
70 North Avenue, Westport, CT 06880
9-120.6 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 44 Pumpkin Hill Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/07/2026
Listed
$3,950,000
132.35%
MLS
5/28/2024
Sold
$1,700,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 44 Pumpkin Hill Rd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$30,853
1%
$1,635,900
—
2023
$30,460
1%
$1,635,900
—
2023
$30,019
2%
$1,635,900
—
2022
$29,561
—
$1,635,900
—
2021
$29,561
-2%
$1,635,900
-9%
2020
$30,088
-1%
$1,800,600
—
2019
$30,358
—
$1,800,600
—
2018
$30,358
—
$1,800,600
—
2017
$30,358
—
$1,800,600
—
2016
$30,358
-12%
$1,800,600
-5%
2015
$34,358
1%
$1,899,300
—
2014
$34,073
-1%
$1,899,300
—
2011
$34,320
—
$1,899,300
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

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Listed by Keller Williams Realty, Christine Oleynick

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44 Pumpkin Hill Road, Westport, CT 06880 (MLS# 24156956) is a Single Family property with 5 bedrooms, 7 full bathrooms and 2 partial bathrooms. 44 Pumpkin Hill Road is currently listed for $3,950,000 and was received on March 07, 2026. Want to learn more about 44 Pumpkin Hill Road? Do you have questions about finding other Single Family real estate for sale in Westport? You can browse all Westport real estate or contact a Coldwell Banker agent to request more information.

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