4 The Fenway
Westport, CT 06880
Map
- 6 beds
- 5 baths
- 5,083 sqft
- ~2 acre lot
- $550 per sqft
- 1966 build
- – on site
Timeless elegance in Westport's prestigious Old Hill. First time on the market in 29 years! This expansive 5-6 bedroom, 4.5 bath farmhouse is gracefully set on 2.22 serene acres, featuring a heated gunite pool, picturesque pond, and a very rare blend of privacy and proximity to town. The sun-drenched primary suite is a true retreat with a fireplace, spa-like bath, and generous walk-in closet. A flexible floor plan includes a potential in-law suite-perfect for multi-generational living or guests. With four wood-burning fireplaces, the home radiates warmth and charm. Multiple living areas offer inviting spaces for relaxation, entertaining, or working from home. The renovated kitchen is the heart of the home, showcasing a large center island and a cozy, picturesque breakfast nook. Outdoors, enjoy beautifully landscaped grounds, the pool and spa, and peaceful natural surroundings. Additional highlights include a whole-house generator, city water, and sewer. A rare opportunity to own a special property in one of Westport's most sought after neighborhoods.
Last checked:
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Last updated Jun 14, 2025
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MLS# 24102844 —
The Building
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Year Built:1966
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Year Built Source:Public Records
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New Construction Type:No/Resale
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Style:Colonial
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Roof Information:Asphalt Shingle
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Attic:Yes
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Attic Description:Unfinished, Storage Space, Pull-Down Stairs
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Exterior Siding:Shingle, Cedar
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Foundation Type:Concrete
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Basement Description:Crawl Space, Unfinished, Sump Pump, Interior Access
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Exterior Features:Underground Utilities, Shed, Porch, Gutters, Lighting, Underground Sprinkler, Patio
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Energy Features:Generator, Storm Doors, Thermopane Windows
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In-Law Access:First Floor
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In-Law Apartment:Possible
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SqFt Total:5083
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SqFt Est Heated Above Grade:5083
Interior
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Interior Features:Auto Garage Door Opener, Cable - Available, Security System
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Fireplaces Total:4
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Laundry Room:Main Level
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Laundry Room Location:Laundry Room on Main Level
Room Dimensions
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Living Area SqFt Per Public Record:5083
Location
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Directions:Woodside to The Fenway
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Neighborhood:Old Hill
The Property
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Parcel Number:413641
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Property Type:Single Family For Sale
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Zoning:AA
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Acres:2.22
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Acres Source:Public Records
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Flood Zone:Yes
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Lot Description:Some Wetlands, Interior Lot, Lightly Wooded, Level Lot
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Elevation Certificate:No
Listing Agent
- Contact info:
- Agent phone:
- (203) 221-0666
Taxes
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Tax Year:July 2024-June 2025
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Property Taxes:21000
Beds
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Beds Total:6
Baths
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Total Baths:5
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Full Baths:4
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Half Baths:1
The Listing
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https://my.homediary.com/u/483498
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Home Warranty Offered:No
Heating & Cooling
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Heat Type:Hot Air, Zoned
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Heat Fuel Type:Oil
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Cooling System:Central Air, Zoned
Utilities
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Water Source:Public Water Connected
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Sewage System:Public Sewer Connected
Appliances
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Appliances Included:Gas Range, Microwave, Range Hood, Freezer, Subzero, Dishwasher, Disposal, Compactor, Washer, Dryer, Wine Chiller
Schools
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Elementary School:Kings Highway
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Middle Or Junior School:Coleytown
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High School:Staples
The Community
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Nearby Amenities:Golf Course, Library, Park, Public Transportation, Shopping/Mall
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Swimming Pool:Yes
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Pool Description:Gunite, Heated, Spa, In Ground Pool
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Direct Waterfront:Yes
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Waterfront Description:Pond, Beach Rights
Parking
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Garage & Parking:Attached Garage
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Garages Number:2
Monthly cost estimate
Asking price
$2,799,000
| Expense | Monthly cost |
|---|---|
|
Mortgage
This calculator is intended for planning and education purposes only. It relies on assumptions and information provided by you regarding your goals, expectations and financial situation, and should not be used as your sole source of information. The output of the tool is not a loan offer or solicitation, nor is it financial or legal advice. |
$14,987
|
| Taxes | N/A |
| Insurance | $769 |
| Utilities | $595 See report |
| Total | $16,351/mo.* |
| *This is an estimate |
Walk Score®
Provided by WalkScore® Inc.
Walk Score is the most well-known measure of walkability for any address. It is based on the distance to a variety of nearby services and pedestrian friendliness. Walk Scores range from 0 (Car-Dependent) to 100 (Walker’s Paradise).
Bike Score®
Provided by WalkScore® Inc.
Bike Score evaluates a location's bikeability. It is calculated by measuring bike infrastructure, hills, destinations and road connectivity, and the number of bike commuters. Bike Scores range from 0 (Somewhat Bikeable) to 100 (Biker’s Paradise).
Soundscore™
Provided by HowLoud
Soundscore is an overall score that accounts for traffic, airport activity, and local sources. A Soundscore rating is a number between 50 (very loud) and 100 (very quiet).
Air Pollution Index
Provided by ClearlyEnergy
The air pollution index is calculated by county or urban area using the past three years data. The index ranks the county or urban area on a scale of 0 (best) - 100 (worst) across the United Sates.
Sale history
| Date | Event | Source | Price | % Change |
|---|---|---|---|---|
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6/14/25
Jun 14, 2025
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Coming Soon | SMART_MLS | $2,799,000 | 229.7% (109.8% / YR) |
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5/12/23
May 12, 2023
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SMART_MLS | $849,000 | ||
|
7/29/96
Jul 29, 1996
|
SMART_MLS |
