365 Toilsome Hill
Fairfield, CT 06825
Map
- 4 beds
- 4 baths
- 3,686 sqft
- ~1 acre lot
- $459 per sqft
- 1914 build
- – on site
Truly One-of-a-Kind. This iconic Fairfield Tudor Revival blends rich architectural heritage with elevated modern luxury. Set on just under an acre, it offers the quiet elegance of a private estate-yet just beyond the drive, sidewalks lead to playgrounds, friendly neighbors, and the charm of a walkable community. Built in stone and stucco with a polychromatic slate roof, copper gutters, and fieldstone details, this home has presence and soul. Inside, original beams, arched doorways, deep sills, wainscoting, and a soaring tin ceiling bring warmth and character. Thick stone walls keep it cool in summer, warm in winter, and quiet all year. The reimagined primary suite feels like a five-star spa: radiant stone floors, steam shower, soaking tub, towel warmer, skylight, instant hot water and its own climate zone. All bathrooms and the kitchen feature radiant heat floors. Outside, entertain under the stars with a wood-burning hearth and pizza oven. Full plans available for future kitchen expansion. 10 mins to train, Whole Foods, and just 5 miles to the beach. This is turnkey luxury-timeless, stylish, unforgettable.
Last checked:
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Last updated Jul 2, 2025
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MLS# 24107907 —
The Building
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Year Built:1914
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Year Built Source:Public Records
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New Construction Type:No/Resale
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Style:Colonial, Tudor
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Roof Information:Slate
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Attic:Yes
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Attic Description:Storage Space, Access Via Hatch
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Exterior Siding:Wood, Stucco
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Foundation Type:Stone
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Basement Description:Full, Unfinished, Storage, Concrete Floor, Full With Walk-Out
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Exterior Features:Balcony, Terrace, Gutters, Lighting, Stone Wall, French Doors
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Energy Features:Programmable Thermostat, Thermopane Windows
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SqFt Total:3686
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SqFt Est Heated Above Grade:3686
Interior
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Fireplaces Total:4
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Laundry Room:Lower Level
Room Dimensions
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Living Area SqFt Per Public Record:3686
Location
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Directions:Stratfield Rd to Toilsome Hill Rd.
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Neighborhood:Stratfield
The Property
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Parcel Number:117958
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Property Type:Single Family For Sale
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Zoning:R3
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Acres:0.95
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Acres Source:Public Records
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Flood Zone:No
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Lot Description:Dry, Level Lot
Listing Agent
- Contact info:
- Agent phone:
- (203) 227-8424
Taxes
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Tax Year:July 2024-June 2025
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Property Taxes:16767
Beds
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Beds Total:4
Baths
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Total Baths:4
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Full Baths:3
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Half Baths:1
The Listing
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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:Natural Gas
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Cooling System:Central Air
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, Subzero, Dishwasher, Washer, Dryer
Schools
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Elementary School:Stratfield
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Middle Or Junior School:Tomlinson
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High School:Fairfield Warde
The Community
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Nearby Amenities:Golf Course, Health Club, Library, Medical Facilities, Playground/Tot Lot
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Swimming Pool:No
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Direct Waterfront:No
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Waterfront Description:Beach Rights, Water Community
Parking
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Garage & Parking:Attached Garage
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Garages Number:2
Monthly cost estimate
Asking price
$1,695,000
| 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. |
$9,076
|
| Taxes | N/A |
| Insurance | $466 |
| Utilities | $568 See report |
| Total | $10,110/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 |
|---|---|---|---|---|
|
7/1/25
Jul 1, 2025
|
Coming Soon | SMART_MLS | $1,695,000 | 9.4% (5.9% / YR) |
|
12/2/23
Dec 2, 2023
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SMART_MLS | $1,550,000 | ||
|
10/11/23
Oct 11, 2023
|
SMART_MLS | $1,550,000 |
