365 Toilsome Hill Road, Fairfield, CT 06825
Local realty services provided by:ERA Hart Sargis-Breen Real Estate
365 Toilsome Hill Road,Fairfield, CT 06825
$1,695,000
- 4 Beds
- 4 Baths
- 3,686 sq. ft.
- Single family
- Pending
Listed by: cindy raney
Office: coldwell banker realty
MLS#:24123685
Source:CT
Price summary
- Price:$1,695,000
- Price per sq. ft.:$459.85
About this home
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.
Contact an agent
Home facts
- Year built:1914
- Listing ID #:24123685
- Added:137 day(s) ago
- Updated:November 15, 2025 at 08:40 PM
Rooms and interior
- Bedrooms:4
- Total bathrooms:4
- Full bathrooms:3
- Half bathrooms:1
- Living area:3,686 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Hot Water
Structure and exterior
- Roof:Slate
- Year built:1914
- Building area:3,686 sq. ft.
- Lot area:0.95 Acres
Schools
- High school:Fairfield Warde
- Middle school:Tomlinson
- Elementary school:Stratfield
Utilities
- Water:Public Water Connected
Finances and disclosures
- Price:$1,695,000
- Price per sq. ft.:$459.85
- Tax amount:$17,061 (July 2025-June 2026)
New listings near 365 Toilsome Hill Road
- New
$999,000Active4 beds 4 baths3,134 sq. ft.66 Wynn Wood Drive, Fairfield, CT 06825
MLS# 24139970Listed by: Higgins Group Real Estate - Open Sun, 1 to 3pmNew
$985,000Active3 beds 3 baths2,308 sq. ft.97 Field Point Drive #97, Fairfield, CT 06824
MLS# 24139297Listed by: William Raveis Real Estate - Open Sun, 12 to 2pmNew
$509,500Active3 beds 2 baths1,510 sq. ft.155 Moody Avenue, Fairfield, CT 06825
MLS# 24139177Listed by: William Raveis Real Estate - New
$435,000Active1 beds 1 baths902 sq. ft.245 Unquowa Road #APT 33, Fairfield, CT 06824
MLS# 24140237Listed by: William Raveis Real Estate - Open Sun, 12 to 2pmNew
$749,000Active3 beds 2 baths1,737 sq. ft.476 Mill Hill Terrace, Fairfield, CT 06890
MLS# 24140193Listed by: William Raveis Real Estate - Open Sun, 1 to 4pmNew
$1,449,000Active4 beds 4 baths2,944 sq. ft.85 Patrick Drive, Fairfield, CT 06824
MLS# 24139153Listed by: William Raveis Real Estate
$2,498,000Active5 beds 8 baths8,136 sq. ft.88 Merry Meet Circle, Fairfield, CT 06824
MLS# 24132125Listed by: The Agency- Open Sun, 12 to 2pmNew
$1,950,000Active5 beds 6 baths4,239 sq. ft.309 Hunyadi Avenue, Fairfield, CT 06824
MLS# 24138639Listed by: Higgins Group Real Estate - New
$565,000Active3 beds 2 baths1,291 sq. ft.101 Soundview Avenue, Fairfield, CT 06825
MLS# 24139102Listed by: Coldwell Banker Realty - Open Sun, 11am to 1pmNew
$1,599,000Active4 beds 3 baths3,867 sq. ft.338 Orchard Hill Lane, Fairfield, CT 06824
MLS# 24139227Listed by: Coldwell Banker Realty