#24106721, Carmen Desiato, Listing office: Higgins Group Real Estate
#24107907·
Listing office: Coldwell Banker Realty·
Listing agent: Cindy Raney·
Listing office phone: (203) 227-8424
$1,695,000 List price
365 Toilsome Hill Rd Fairfield, CT 06825
4 beds
3 full, 1 partial
3,686 sqft
0.9 acres
$460 / sqft
House
Property details
About 365 Toilsome Hill Rd
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.
Highlights
Home typeOther
HeatingForced Air, Zoned
StatusActive
CoolingCentral Air, Split System
Size3,686 sqft
BasementYes
Lot size0.95 Acres
Year built1914
ParkingAttached Garage
MLS #24107907
Attached garage2 spaces
WaterfrontBeach, Water Access
Summary
- Partial Bathrooms: 1
- Full Bathrooms: 3
- Appliances: Gas Range, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer
- Basement: Yes
- Total Bedroom Count: 4
- Garage Space: 2 spaces
- Attached Garage: Yes
- Private Pool: No
- Parking: Attached Garage
- Waterfront: Beach, Water Access
- Exterior: Balcony, Terrace, Gutters, Lighting, Stone Wall, French Doors
- Architectural Style: Colonial, Tudor
- Heating: Forced Air, Zoned
- Cooling: Central Air, Split System
- List Price: $1,695,000
- Price/SqFt: $459
- Annual Tax Amount: $16,767
- Tax Year: 2024
- Lot: Level
- Directions: Stratfield Rd to Toilsome Hill Rd.
- Year Built: 1914
- Living Area: 3,686 SqFt
- Lot Size: 0.95 Acres
- MLS Number: 24107907
- Office Name: Coldwell Banker Realty
- Office Phone: (203) 227-8424
- Office Email: cindy@cindyraney.com
- Listing Agent: Cindy Raney
Copyright © 2025 Smart MLS. The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 7/23/2025, 2:45:30 AM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
Price information
Property sales
| Date | Event | Price |
|---|---|---|
| Dec 06, 2023 | Home Sold | $1,550,000 |
| Jun 07, 2005 | Home Sold | $690,000 |
| Apr 26, 2005 | Home Sold | $30,000 |
Tax history
| Year | Assessment | Property Tax |
|---|---|---|
| 2024 | $600,950 | $16,767 |
| 2023 | $600,950 | $16,532 |
| 2022 | $600,950 | $16,370 |
| 2021 | $600,950 | $16,214 |
| 2020 | $651,630 | $17,457 |
| 2019 | $651,630 | $17,457 |
History based on county public records data.
Nearby schools
7
Stratfield School
Public District KG-5
0.5 mi
•1407 Melville Ave
2
Madison School
Public District KG-6
1.0 mi
•376 Wayne St
8
Jennings School
Public District KG-5
1.2 mi
•31 Palm Dr
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $161,742. The most common annual income of people living in Fairfield, CT is $200k+. The most common type of family is married, with kids. The majority of residents in this area have post secondary degree education.
How much money do the neighbors make?
9%
<35k
27%
35k-100k
30%
100k-200k
34%
200k+
What level of education do the neighbors have?
High School Diploma
Post Secondary Degree
Masters Degree
Doctorate
What types of families live nearby?
18%
Single, No Kids
6%
Single, with Kids
28%
Married, No Kids
48%
Married, with Kids
Are the neighbors home owners or renters?
Home Owners
Renters
How old are people in this area?
22%
<11 yrs old
14%
12-17 yrs old
9%
18-34 yrs old
46%
35-64 yrs old
9%
65+ yrs old
What do the neighbors do for fun?
Skiing/snowboarding
Tennis- Men's Tennis
Where do the neighbors shop?
Nordstrom
Brooks Brothers
Bloomingdales
Where do the neighbors go to eat?
California Pizza Kitchen
Qdoba
Bonefish Grill
What do the neighbors drive?
BMW
Acura
Lexus
What do the neighbors listen to?
Talk/Personality
Sports
News
All data provided by Home Junction and Claritas
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Frequently asked questions
Living in Fairfield, CT
Fairfield features a solid transportation infrastructure, with a variety of public transit options that connect residents to nearby cities and amenities. The town's walkability varies by area, with the downtown district being particularly pedestrian-friendly. A network of roads and highways, including the I-95, facilitates commuting and travel. While specific ride-sharing services are available, their presence complements the existing transportation options, ensuring residents and visitors can navigate the town with ease.
The community benefits from a robust educational system, including multiple public schools at the elementary, middle, and high school levels, as well as private educational institutions that cater to a range of learning preferences. Healthcare services are comprehensive, with facilities offering urgent care, primary care, and specialized medical services. The public library system is well-established, providing residents with access to a wealth of resources and programs. Retail and dining options abound, showcasing the local culture and cuisine, with city initiatives in place to continually enhance these services.
Fairfield is celebrated for its coastal charm and community-oriented atmosphere. The town prides itself on its beautiful beaches, abundant green spaces, and a vibrant downtown area that hosts various seasonal events, reflecting the residents' pride in their town and its heritage. The community's character is further enriched by its commitment to preserving historical landmarks and promoting local arts and culture.
Fairfield's housing market is diverse, offering a range of options from charming colonial homes to contemporary condominiums. Single-family homes are prevalent, making up a significant portion of the housing stock, while apartments and townhouses provide alternatives for those seeking a more compact living space. The architectural styles reflect the town's rich history and modern growth, with many homes dating back to the early 20th century, complemented by newer developments.
About 365 Toilsome Hill Rd
The listing price of 365 Toilsome Hill Rd property is $1,695,000.
The property 365 Toilsome Hill Rd is a house located in Fairfield, Connecticut, 06825.
Active Listing: 365 Toilsome Hill Rd is For Sale (Active/New) which means the seller is accepting offers.
The nearby schools for 365 Toilsome Hill Rd are: Stratfield School (GreatSchools Rating 7/10), Madison School (GreatSchools Rating 2/10), Jennings School (GreatSchools Rating 8/10), Blackham School (GreatSchools Rating 2/10), Interdistrict Discovery Magnet School (GreatSchools Rating 3/10), Fairfield Woods Middle School (GreatSchools Rating 6/10), Fairfield Warde High School (GreatSchools Rating 7/10), Central High School (GreatSchools Rating 2/10), Bassick High School (GreatSchools Rating 1/10).
According to the records, the last property tax for 2024 is $16,767 (source: MLS/based on county public records data).
The last sale was on December 6, 2023 for $1,550,000 (source: MLS/tax record).
The property at 365 Toilsome Hill Rd has 4 bedrooms and 3 full and 1 half bathrooms.
The property 365 Toilsome Hill Rd is 3,686 SqFt (source: MLS/tax record).
The year of construction for 365 Toilsome Hill Rd is 1914.
This home is located at 365 Toilsome Hill Rd in Fairfield, CT and zip code 06825. This 3,686 square foot home, which was built in 1914, sits on a 0.95 acre lot. Features: 4 bedrooms, 4 bathrooms. It has been listed on Rocket Homes since July 1, 2025 and is currently priced at $1,695,000.
While more than 38 listings in Fairfield, CT in June 2025 were sold above asking price, there were more than 11 listings sold at asking price, and more than 20 were sold below. The number of homes for sale in Fairfield, CT decreased by 0.4% between May and June 2025.
From Rocket Homes Real Estate and based on county public records data.