365 Toilsome Hill Road

Closed 12/8/25
Closed 12/8/25
Gallery Image 1
Last Sold Price
$1,615,000
4 beds3,686 sqft$438/sqft
365 Toilsome Hill Rd, Fairfield, CT 06825

Description

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,...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, three working fireplaces, 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.
LISTING CLOSED: 12/08/2025 12:00 AM

Listing Agents

  1. Cindy Raney

    Cindy Raney

    Listing Agent

    Coldwell Banker Realty

    P: (203)-625-1820

    CallText
  2. Jess Christ

    Jess Christ

    Alternative Listing Agent

    Coldwell Banker Realty

    P: (203)-227-8424

    CallText

Property Details for 365 Toilsome Hill Road

Status
Closed
MLS #
24123685
Days on Market
33
Taxes
$17,061 / year
HOA Fees
-
Condo/Co-op Fees
-
Property Type
Single Family
MLS Type
Residential
Year Built
1914
Lot Size
0.95 AC / 41,382 SF
County
Fairfield County
Basement Description
Full, Unfinished, Storage, Interior Access, Concrete Floor, Full With Walk-Out
Direct Waterfront
No
Garages Number
2
Neighborhood
Stratfield
Style
Colonial, Tudor
Garage Parking Info
Attached Garage
Swimming Pool
No
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Location

Listing Courtesy of Coldwell Banker Realty, Cindy Raney; Coldwell Banker Realty, Jess Christ

Sold By Brown Harris Stevens, Kat L Gibbon

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Building Information for 365 Toilsome Hill Road

Stories-Year Built1914Building Size-Lot Size0.95 AC / 41,382 SF

Payment Calculator

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$9,631 per month

30 year fixed, 6.55% Interest

Principal and Interest

$8,209

Property Taxes

$1,422

HOA Dues

$0

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Property Information for 365 Toilsome Hill Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Stratfield Rd to Toilsome Hill Rd.
  • Elementary School: Stratfield
  • Flood Zone: No
  • High School: Fairfield Warde
  • Latitude: 41.19863
  • Longitude: -73.22796
  • Middle Jr High School: Tomlinson
  • Neighborhood Amenities: Golf Course, Health Club, Library, Medical Facilities, Playground/Tot Lot
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $17,061
Interior and Exterior Features
Exterior Features
  • Exterior Features: Balcony, Terrace, Gutters, Lighting, Stone Wall, French Doors
  • Waterfront Description: Beach Rights, Water Community
Interior Features
  • Appliances Included: Gas Range, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer
  • Attic Description: Storage Space, Access Via Hatch
  • Cooling System: Central Air
  • Heat Type: Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 3
  • Home Automation: Lighting
  • Laundry Room Info: Lower Level
  • Rooms Total: 9
Room 1
  • Room Entry Order: 1
  • Room Features: Beams,Built-Ins,Fireplace,Hardwood Floor
  • Room Level: Main
  • Room Type: Other
Room 2
  • Room Entry Order: 10
  • Room Features: Tile Floor
  • Room Level: Upper
  • Room Type: Full Bath
Room 3
  • Room Entry Order: 2
  • Room Features: 9 ft+ Ceilings,Fireplace,Hardwood Floor
  • Room Level: Main
  • Room Type: Living Room
Room 4
  • Room Entry Order: 3
  • Room Features: Beams,Combination Liv/Din Rm,Hardwood Floor
  • Room Level: Main
  • Room Type: Dining Room
Room 5
  • Listing Key: 3DE637176B2461ACE0631A01100A6516
  • Room Entry Order: 4
  • Room Features: Granite Counters,Dining Area,Limestone Floor
  • Room Level: Main
  • Room Type: Eat-In Kitchen
Room 6
  • Room Entry Order: 5
  • Room Features: Built-Ins,Ceiling Fan,Hardwood Floor
  • Room Level: Other
  • Room Type: Family Room
Room 7
  • Room Entry Order: 6
  • Room Features: Remodeled,Balcony/Deck,Gas Log Fireplace,Full Bath,Walk-In Closet,Hardwood Floor
  • Room Level: Upper
  • Room Type: Primary BR Suite
Room 8
  • Room Entry Order: 7
  • Room Features: Full Bath,Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 9
  • Listing Key: 3DE637176B2461ACE0631A01100A6516
  • Room Entry Order: 8
  • Room Features: Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 10
  • Room Entry Order: 9
  • Room Features: Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Property
Property and Assessments
  • Construction Description: Frame, Stucco
  • Exclusions: Please see attached Inclusion/Exclusion Addendum
  • Exterior Siding: Wood, Stucco
  • Foundation Type: Stone
  • New Construction Type: No/Resale
  • Roof: Slate
  • Year Built: 1914
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 3686
Lot Information
  • Lot Description: Dry, Level Lot
  • Parcel Number: 117958
  • Sq Ft Est Heated Above Grade: 3686.0
  • Sq Ft Total: 3686.0
  • Zoning: R3
Utilities
  • Energy Features: Programmable Thermostat, Thermopane Windows
  • Heat Fuel Type: Natural Gas
  • Hot Water Description: Domestic, Tankless Hotwater
  • Radon Mitigation Air: No
  • Sewage System: Public Sewer Connected
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 365 Toilsome Hill Road

DateEvent & SourcePriceAppreciation
Dec 1, 2023

Closed (Public Record)

Public Record #1523357255

$1,550,000

+4.5% / yr

Jun 7, 2005

Closed (Public Record)

Public Record #160993096

$690,000

+69490541190625.8% / yr

Apr 26, 2005

Closed (Public Record)

Public Record #159294942

$30,000—
DateEvent & SourcePrice
12/01/2023

Closed (Public Record)

Public Record #1523357255

$1,550,000

+4.5% / yr

06/07/2005

Closed (Public Record)

Public Record #160993096

$690,000

+69490541190625.8% / yr

04/26/2005

Closed (Public Record)

Public Record #159294942

$30,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 365 Toilsome Hill Road

Taxable ValueLand$283,430Additions$317,520Total$600,950
Tax Record2025$17,061 ($1,422 / month)
Home Facts
Beds4Baths3.5Total Finished SqFt3,686 SqFtAbove Grade Finished SqFt3,686 SqFtUnfinished Basement SqFt1,744 SqFtStories2Lot Size41,482 SqFtStyleSingle Family ResidenceYear Built1914Year Renovated1914ZoningR3CountyGREATER BRIDGEPORTAPNFFLD M:30 B:190

Schools near 365 Toilsome Hill Road

This home is within Fairfield School District.
Rating
School
Type
Grades
Distance
Stratfield School
Public - PK to 5
Tomlinson Middle School
Public - 6 to 8
Fairfield Warde High School
Public - 9 to 12
The Unquowa School
Private - PK to 8
Rating
School
Distance
Stratfield School
PublicPK to 5

Tomlinson Middle School
Public6 to 8

Fairfield Warde High School
Public9 to 12

The Unquowa School
PrivatePK to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 365 Toilsome Hill Road, Fairfield, CT 06825
$1,615,000
4
3,686
41,382
341 Toilsome Hill Road, Fairfield, CT 06825
$735,000
5
3,758
35,719
393 Toilsome Hill Road, Fairfield, CT 06825
$640,000
5
3,040
13,068
327 Toilsome Hill Road, Fairfield, CT 06825
$1,500,000
4
2,848
23,522
360 Toilsome Hill Road, Fairfield, CT 06825
–
4
2.5
2,621
10,400
407 Toilsome Hill Road, Fairfield, CT 06825
$635,000
4
3,292
14,374

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Coldwell Banker Realty, Cindy Raney; Coldwell Banker Realty, Jess Christ

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.