1. Connecticut
2. Fairfield
3. 365 Toilsome Hill Road

365 Toilsome Hill Road, Fairfield, CT 06825

• 4 beds |
• 4 baths |
• 3,686 sqft

Property 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, 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 Status:

Active

Date Added:

July 1, 2025 at 09:50PM

Listing Office:

Coldwell Banker Realty : (203) 227-8424

Listing Agent:

Cindy Raney : (203) 257-8320

MLS ID:

24107907

Interior

• Appliances: Gas RangeMicrowaveRange HoodSubzeroDishwasherWasherDryer
• Laundry: Lower Level
• Basement: FullUnfinishedStorageConcrete FloorFull With Walk-Out
• A/C: Central AirSplit System
• Heating: Hot AirZonedNatural Gas
• Fireplace: Fireplaces: 4

Exterior

Construction

Location

Lot

Utilities

Financial

This listing courtesy of Cindy Raney, Coldwell Banker Realty