About 365 Toilsome Hill Road
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.
Features of 365 Toilsome Hill Road
| MLS® # | 24123685 |
|---|---|
| Price | $1,695,000 |
| Bedrooms | 4 |
| Bathrooms | 4.00 |
| Full Baths | 3 |
| Half Baths | 1 |
| Square Footage | 3,686 |
| Acres | 0.95 |
| Type | Single Family For Sale |
| Style | Colonial, Tudor |
| Status | Under Contract - Continue to Show |
Community Information
| Address | 365 Toilsome Hill Road |
|---|---|
| Area | Stratfield |
| City | Fairfield |
| County | Fairfield |
| State | Connecticut |
| Zip Code | 06825 |
Amenities
| Features | Programmable Thermostat, Thermopane Windows |
|---|---|
| Parking | Attached Garage |
| # of Garages | 2 |
| Is Waterfront | No |
| Waterfront | Beach Rights, Water Community |
| Has Pool | No |
Interior
| Appliances | Gas Range, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer |
|---|---|
| Heating | Hot Water, Natural Gas |
| Cooling | Central Air |
| Fireplace | Yes |
| # of Fireplaces | 3 |
| Has Basement | Yes |
| Basement | Full, Unfinished, Storage, Interior Access, Concrete Floor, Full With Walk-Out |
Exterior
| Exterior | Wood, Stucco |
|---|---|
| Exterior Features | Balcony, Terrace, Gutters, Lighting, Stone Wall, French Doors |
| Lot Description | Dry, Level Lot |
| Roof | Slate |
| Foundation | Stone |
School Information
| Elementary | Stratfield |
|---|---|
| Middle | Tomlinson |
| High | Fairfield Warde |
Additional Information
| Date Listed | September 3rd, 2025 |
|---|---|
| Days on Market | 35 |
| Zoning | R3 |
| RE / Bank Owned | No |
Listing Details
| Office | Coldwell Banker Realty |
|---|