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365 Toilsome Hill Road, 
Fairfield, CT 06825

$1,695,000


4

Beds


4

Baths


3,686

Sq Ft


Single Family

Coming Soon

Listed by

Cindy Raney

Last updated:

July 3, 2025, 04:43 PM

MLS#

24107907

Source:

CT

Company Logo

About This Home

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.

Home Facts

Single Family

4 Baths

4 Bedrooms

Built in 1914

Price Summary

1,695,000

$459 per Sq. Ft.

MLS #:

24107907

Last Updated:

July 3, 2025, 04:43 PM

Added:

4 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

4

Full Bathrooms:

3

Interior

Living Area:

3,686 Sq. Ft.


Structure

Structure

Architectural Style:

Colonial, Tudor

Building Area:

3,686 Sq. Ft.

Year Built:

1914


Lot

Lot Size (Sq. Ft):

41,382


Finances & Disclosures

Finances

Price:

$1,695,000

Price per Sq. Ft:

$459 per Sq. Ft.

365 Toilsome Hill Road
Source:CT
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