365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
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365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
365 Toilsome Hill Road
For Sale

365 Toilsome Hill Road

365 Toilsome Hill Road, Fairfield, CT 06825

$1,695,000
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.

8/3/2025 1:00PM - 3:00PM EDT

4
beds

4
baths

3,686 Sq.Ft. LIVING AREA

0.95 Acres lot

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Schedule a Showing

We would love to show you our beautiful property. Please select your preferred date and time below. An agent will be in touch shortly to confirm your appointment.

Schedule a Showing

We would love to show you our beautiful property. Please select your preferred date and time below. An agent will be in touch shortly to confirm your appointment.

Thank you for your interest in 365 Toilsome Hill Road, Fairfield, CT 06825. We are reviewing your request and will be in touch shortly!
Cindy Raney

Cindy Raney

Features & Amenities

Interior

  • total bedrooms4
  • Total bathrooms4
  • full bathrooms3
  • half bathroom1
  • APPLIANCES Dishwasher, Dryer, Gas Range, Microwave, Washer, Range Hood

Area & Lot

  • Status For Sale
  • OPEN HOUSE

    8/3/2025 1:00PM - 3:00PM EDT

  • Living Area3,686 Sq.Ft.
  • Lot Area0.95 Acres
  • MLS® ID24107907
  • TypeResidential
  • YEAR BUILT1914
  • NeighborhoodFairfield
  • Architecture StylesColonial, Tudor
  • Water FrontageBeach Front
  • Elementary SchoolStratfield
  • Middle SchoolTomlinson
  • High SchoolFairfield Warde

Exterior

  • Garage Space2.0
  • water SourcePublic
  • lot featuresLevel
  • parkingAttached
  • HEAT TYPENatural Gas, Forced Air, Zoned
  • AIR CONDITIONINGCentral Air
  • sewerPublic Sewer
  • SubstructureStone
  • other exterior FeaturesBalcony

Financial

  • Sales Price$1,695,000
  • Buyer Agency Compensation 2%
  • Real Estate Tax $17,061/yr
  • Zoning R3

Fairfield

Fairfield, Connecticut is an affluent town located on the shoreline of the Long Island Sound.

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Work With Us

Cindy Raney & Team is the elite, boutique real estate team in Fairfield County. They are extremely well versed in the industry, having sold over half a billion dollars in luxury real estate. Cindy’s team is particularly focused on the client experience, helping them throughout the home buying or selling process to ensure that their experience with the team is exceptional.

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