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.
Public Records
Jun 7, 2005
Sold
$690,000
$187/sq ft
Smart MLS #98221319
Jun 1, 2005
Listing Removed
—
Jan 3, 2005
Listed
$775,000
$210/sq ft
Smart MLS #98226356
Feb 20, 2005
Listed
$775,000
$210/sq ft
Smart MLS #98222422
Feb 19, 2005
Listing Removed
—
Jan 12, 2005
Listed
$799,000
$217/sq ft
Smart MLS #98211370
Jan 12, 2005
Listing Removed
—
Sep 9, 2004
Listed
$799,900
$217/sq ft
Year
Property tax
Land + Additions
Assessment*
2023
$16,532 (+1.0%)
$283,430 + $317,520
$600,950
2022
$16,370 (+1.0%)
$283,430 + $317,520
$600,950
2021
$16,214 (−7.1%)
$283,430 + $317,520
$600,950
2020
$17,457
$285,250 + $366,380
$651,630
2019
$17,457 (+1.6%)
$285,250 + $366,380
$651,630
2018
$17,177 (+2.1%)
$285,250 + $366,380
$651,630
2017
$16,825 (+1.5%)
$285,250 + $366,380
$651,630
2016
$16,584 (+9.7%)
$285,250 + $366,380
$651,630
2014
$15,118
$319,130 + $300,440
$619,570
Tax history for 365 Toilsome Hill Rd
Year
Property tax
Land + Additions
Assessment*
2023
$16,532 (+1.0%)
$283,430 + $317,520
$600,950
2022
$16,370 (+1.0%)
$283,430 + $317,520
$600,950
2021
$16,214 (−7.1%)
$283,430 + $317,520
$600,950
2020
$17,457
$285,250 + $366,380
$651,630
2019
$17,457 (+1.6%)
$285,250 + $366,380
$651,630
2018
$17,177 (+2.1%)
$285,250 + $366,380
$651,630
2017
$16,825 (+1.5%)
$285,250 + $366,380
$651,630
2016
$16,584 (+9.7%)
$285,250 + $366,380
$651,630
2014
$15,118
$319,130 + $300,440
$619,570
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Beds
4
Baths
3.5
Stories
2
Lot width
—
Lot depth
—
Lot size
0.95 Acres
Year renovated
—
Sq. Ft.
3,686
Year built
1914
Style
Single Family Residential
County
Fairfield County
APN
117958
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 13, 2023.
Property details
Parking
Garage Information
Garage & Parking: Attached Garage
Garages Number: 2
Interior
Interior Information
Total Rooms: 9
Laundry Room Info: Lower Level
Lighting
Fireplaces Total: 3
Cooling System: Central Air
Appliances Included: Gas Range, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer
Bathroom Information
# of Baths (Full): 3
# of Baths (Half): 1
Bedroom Information
Beds Total: 4
Room Information
Basement Description: Full, Unfinished, Storage, Interior Access, Concrete Floor, Full With Walk-Out
Has Attic
Attic Description: Storage Space, Access Via Hatch
Exterior
Exterior Features
Roof Information: Slate
Exterior Siding: Wood, Stucco
Exterior Features: Balcony, Terrace, Gutters, Lighting, Stone Wall, French Doors
Lot Information
Lot Description: Dry, Level Lot
Building Information
Foundation Type: Stone
Construction Description: Frame, Stucco
Property Information
Waterfront Description: Beach Rights, Water Community
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 3686
Financial
Assessments Information
Assessed Value: $600,950
Utilities
Utility Information
Water Source: Public Water Connected
Sewage System: Public Sewer Connected
Hot Water Description: Domestic, Tankless Hotwater
Heat Type: Hot Water
Heat Fuel Type: Natural Gas
Energy Features: Programmable Thermostat, Thermopane Windows
Location
School Information
Middle Jr High School: Tomlinson
High School: Fairfield Warde
Elementary School: Stratfield
Location Information
State: Connecticut
Nearby Amenities: Golf Course, Health Club, Library, Medical Facilities, Playground/Tot Lot
Directions: Stratfield Rd to Toilsome Hill Rd.
County: Fairfield
Public facts
Beds: 4
Baths: 3.5
Sq. Ft.: 3,686
Stories: 2.0
Lot Size: 0.95 acres
Style: Single Family Residential
Year Built: 1914
Year Renovated: —
County: Fairfield County
APN: 117958
Home facts updated by county records on Jul 13, 2023
Other
Documents & Disclosures
Supplement Count Public: 4
Around this home
Schools
Stratfield School
Public PreK-5 • Assigned • 0.6mi
7/10
Tomlinson Middle School
Public 6-8 • Assigned • 4.1mi
8/10
Fairfield Warde High School
Public 9-12 • Assigned • 0.9mi
9/10
Provided by GreatSchools
Lifestyle
Provided by Walk Score and Local Logic
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
6/10 Heat Factor
7 days above 97° expected this year, 15 days in 30 years
6/10 Wind Factor
27% chance of strong winds in next 30 years
4/10 Air Factor
5 unhealthy days expected this year, 7 days in 30 years
Provided by First Street
Historical weather
Fairfield, CT • 06825
Average low and high temperatures (°F)
35
22
37
24
52
34
61
44
69
53
80
63
84
68
82
62
77
59
66
48
55
39
40
27
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
In this area, properties receive around 8.8 hours in
June and 4.4 hours in December, placing it below the
U.S. average for solar exposure.
8.8 hrs
4.4 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$1.67M – $2.02M
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