Toilsome Hill Rd

4 Bedroom House has been listed for sale at 365 Toilsome Hill Rd in Fairfield for $1,695,000. Chat with a local expert, book a tour.

Fairfield

Stratfield

365 Toilsome Hill Rd

365 Toilsome Hill Rd, For Sale in Fairfield - eXp Commercial Brokerage

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.

Lift the Lion's head bronze door knocker and enter a Timeless Masterpiece nestled on a sprawling one-acre property. Vintage charm meets modern comforts in this enchanting English Tudor Revival, with stunning Fieldstone exterior, Arched windows, Wood Beams, and gorgeous Wide Plank Oak Floors. Main living areas feature original details and Exquisite Craftsmanship at every turn. Living Room with Wood Burning Fireplace and charming built-in Dry Bar, Family Room with soaring Tin Ceiling, abundant light and cozy fireplace, perfect spaces for relaxing and entertaining. A Spacious Dining Room accommodates all your guests, while intimate enough for everyday dinners. Updated Gourmet Kitchen with Sub Zero, Miele, Mahogany Cabinets, and radiant Limestone Floors, crowned with an AGA Gas Range, ready for your culinary creations. Enjoy morning coffee at the Breakfast Bar overlooking the front garden, or slip into the Dining Nook for casual meals. The Playroom is steps from the kitchen, or ideal for Home Office or 5th Bedroom. Second Level offers a luxurious Primary En Suite Bedroom with Stone Fireplace, Walk-In Closets and Balcony overlooking the patio and gardens, plus three additional Bedrooms and two Full Baths. Park-like grounds for parties, play and gardening, with peaceful evenings by the Outdoor Fireplace and Pizza Oven. Room for a Pool! With spacious living areas, updated features and picturesque grounds, this is an exceptional opportunity to own a piece of architectural history.

365 Toilsome Hill Rd, Fairfield, CT

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