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$1,615,000

  • Sold
  • Closed
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,686 Sq. Ft.
  • 2 Car Garage
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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.

Full Property Details for 365 Toilsome Hill Rd

General

  • Sold For: $1,615,000
  • Taxes: (July 2025-June 2026)
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24123685
  • Added to Site: 170 day(s) ago

Interior

  • Number of Rooms: 9
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Appliances: Gas Range, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Full Bath: Tile Floor, Upper

Bedrooms

  • Total Bedrooms: 4
  • Primary Suite: Remodeled, Balcony/Deck, Gas Log Fireplace, Full Bath, Upper
  • Bedroom 1: Bedroom - Hardwood Floor, Upper
  • Bedroom 2: Bedroom - Full Bath, Hardwood Floor, Upper
  • Bedroom 3: Bedroom - Hardwood Floor, Upper

Other Rooms

  • Living Room: Living Room - 9 ft+ Ceilings, Fireplace, Hardwood Floor, Main
  • Family Room: Family Room - Built-Ins, Ceiling Fan, Hardwood Floor, Other
  • Eat In Kitchen: Eat-In Kitchen - Granite Counters, Dining Area, Limestone Floor, Main
  • Dining Room: Dining Room - Beams, Combination Liv/Din Rm, Hardwood Floor, Main
  • Laundry: Lower Level
  • Other Room 1: Other - Beams, Built-Ins, Fireplace, Hardwood Floor, Main

Exterior

  • Exterior Features: Balcony, Terrace, Gutters, Lighting, Stone Wall, French Doors

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking: Attached Garage

Location

  • County: Fairfield
  • Neighborhood: Stratfield
  • Driving Directions: Stratfield Rd to Toilsome Hill Rd.

School Information

  • Elementary School: Stratfield
  • Middle School: Tomlinson
  • High School: Fairfield Warde

Community

  • Community Name: Stratfield

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Water, Natural Gas
  • Heating Fuel: Natural Gas
  • Water Heater: Domestic, Tankless Hotwater

Utilities

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

Structural Information

  • Architectural Style: Colonial, Tudor
  • Construction Status: No/Resale
  • Exterior Const.: Wood, Stucco
  • Basement Desc.: Full, Unfinished, Storage, Interior Access, Concrete Floor, Full With Walk-Out
  • Roof: Slate
  • Attic: Yes
  • Square Feet: 3,686
  • Above Ground: 3,686 Sq. Ft.
  • Year Built: 1914

Lot Features

  • Lot Size (Acres): 0.95
  • Zoning: R3
  • Lot Description: Dry, Level Lot

Water Features

  • Water Front Desc.: Beach Rights, Water Community

Green Features

  • Energy Features: Programmable Thermostat, Thermopane Windows

Financial Considerations

  • Assessment Amount: $600,950
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Exclusions: Please see attached Inclusion/Exclusion Addendum
  • Property ID: 117958

Meet the listing agent

Meet the listing agent
— 365 Toilsome Hill Rd —

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NMLS#: 1598647

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Schools serving 365 Toilsome Hill Rd

School District:Fairfield School District
NameGradesDistance
Stratfield School
1407 Melville Avenue, Fairfield, CT 06825
K-50.5 mi
Tomlinson Middle School
200 Unquowa Road, Fairfield, CT 06824
6-84.1 mi
Fairfield Warde High School
755 Melville Avenue, Fairfield, CT 06825
9-120.9 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 365 Toilsome Hill Rd

Date
Details
Price
Change
Source
12/08/2025
Sold
$1,615,000
-4.72%
MLS
9/03/2025
Listed
$1,695,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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365 Toilsome Hill Road, Fairfield, CT 06825 (MLS# 24123685) is a Single Family property that was sold at $1,615,000 on December 08, 2025. This property was listed by Cindy Raney & Team from our Westport Office.Want to learn more about 365 Toilsome Hill Road? Do you have questions about finding other Single Family real estate for sale in Fairfield? You can browse all Fairfield real estate or contact a Coldwell Banker agent to request more information.