365 Toilsome Hill Road
Courtesy of Coldwell Banker Realty
Sold

365 Toilsome Hill Road

365 Toilsome Hill Road, Fairfield, Connecticut 06825

$1,615,000
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.

4
beds

4
baths

3,686 Sq.Ft. LIVING AREA

0.95 Acres lot

Cindy Raney

Cindy Raney

Features & Amenities

Interior

  • total bedrooms4
  • Total bathrooms4
  • full bathrooms3
  • half bathroom1
  • Laundry room Lower Level
  • APPLIANCES Gas Range, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer

Area & Lot

  • Status Sold
  • Date Sold December 8, 2025
  • Living Area3,686 Sq.Ft.
  • Total Area3,686 Sq.Ft.
  • Lot Area0.95 Acres
  • MLS® ID24123685
  • TypeResidential
  • YEAR BUILT1914
  • Architecture StylesColonial, Tudor
  • Water FrontageBeach Rights, Water Community
  • Elementary SchoolStratfield
  • Middle SchoolTomlinson
  • High SchoolFairfield Warde

Exterior

  • Garage Space2.0
  • water SourcePublic Water Connected
  • roofSlate
  • lot featuresDry, Level Lot
  • parkingAttached Garage
  • HEAT TYPEHot Water
  • AIR CONDITIONINGCentral Air
  • sewerPublic Sewer Connected
  • SubstructureStone
  • other exterior FeaturesBalcony, Terrace, Gutters, Lighting, Stone Wall, French Doors

Financial

  • Sales Price$1,615,000
  • Real Estate Tax $17,061/yr
  • Zoning R3

Work With Us

Cindy Raney & Team is an elite boutique real estate team in Fairfield County with extensive industry expertise, having sold over $800 million in luxury real estate. Cindy’s team is deeply focused on the client experience, guiding clients through every step of the home buying or selling process to ensure an exceptional experience from start to finish.

Follow Us on Instagram