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.
Listed by Cindy Raney
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Coldwell Banker Realty
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(203) 257-8320
Last updated September 04, 2025
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Source: SmartMLS #24123685
Listing Facts
TypeSingle-family
NeighborhoodStratfield Village
Bedrooms4
Bathrooms4
Days on Prevu3
Taxes$17,061/year
Size3,686 sqft
Price per sqft$460
Location
Mortgage Calculator
Listing History
09/03/2025
Listed by Coldwell Banker Realty
$1,695,000
Property Details for 365 Toilsome Hill Road
Exterior
Construction
New Construction: No/Resale
Roof: Slate
Year Built: 1914
Year Built Details: Public Records
Architectural Style: Colonial, Tudor
Construction Materials: Frame, Stucco
Exterior Features: Balcony, Terrace, Gutters, Lighting, Stone Wall, French Doors
Features
Waterfront Features: Beach Rights, Water Community
Measurements
Lot Features: Dry, Level Lot
Lot Size Acres: 0.95
Financial
Taxes
Parcel Number: 117958
Tax Annual Amount: $17,061.00
Tax Year: 25
Interior
Features
Appliances: Gas Range, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer
Fireplaces Total: 3
Measurements
Living Area: 3,686
Rooms
Basement: Full, Unfinished, Storage, Interior Access, Concrete Floor, Full With Walk-Out
Bathrooms Full: 3
Bathrooms Half: 1
Bathrooms Total Integer: 4
Bedrooms Total: 4
Rooms Total: 9
Other
General
Exclusions: Please see attached Inclusion/Exclusion Addendum
Parking
Parking
Attached Garage: Attached Garage
Garage Spaces: 2
Schools
Elementary School
Elementary School: Stratfield
High School
High School: Fairfield Warde
Middle or Junior School
Middle Or Junior School: Tomlinson
Utilities
Equipment
Cooling: Central Air
Heating: Hot Water
Laundry Features: Lower Level
Sewer: Public Sewer Connected
Water Source: Public Water Connected
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