299 Toilsome Hill Rd, Fairfield, CT 06825

Off market jul 2019 for $775K

$1,539,711

Est. refi paymentEst. refi $5,139/mo

•

3,475

sq ft

299 Toilsome Hill Rd, Fairfield, CT 06825

About this home

Welcome to 299 Toilsome Hill Rd! Quintessential 1930 Colonial full of charm in the Stratfield section of Fairfield. Situated on tree lined street, you will find this beautiful home set back behind stone walls on a half acre creating a private oasis. Recently remodeled and tastefully decorated this 5 bedroom, 3.5 bath home boasting over 3400 sq ft has all you are looking for. Expansive living room with hard wood floors, fireplace, floor to ceiling built-ins and bow window is the place to host your next party. Updated classic white and grey kitchen with marble center island, stainless steel 6 burner stove and granite counters offers a place to be creative. Large dining room filled with light and a cozy ship- lapped family room completes the first floor. Master suite has walk in closets, new full bathroom and 2nd floor laundry and office. Three more gracious sized bedrooms and hallway full bath to are all updated. Located on the third floor is the 5th bedroom with second staircase, full bath and a play room for all ages. Back staircase once used for servants now offers an easy flow that leads right into the kitchen. End your day in the backyard on the bluestone patio with nature surrounding you. This is a home not to be missed!

Single-familyProperty Type

1930Year Built

0.54 acresLot Size

$443Est. Price/Sq.Ft.

2 car garageParking

Listed by Robert Manware • William Raveis Real Estate

Listed by Al Filippone • William Raveis Real Estate

Bought with Michelle Hennessey • William Raveis Real Estate

Bought with Al Filippone • William Raveis Real Estate

Source:Smart MLS #170173630

Redfin Estimate

$1,539,711

$765K since sold in July 2019$8,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 28.5% higher than the average sale price ($1.20M) of 6 comparable homes.

SOLD OCT 9, 2026
$1,389,000
A
6 beds3.5 baths2,982 sq ft
594 Stratfield Rd, Fairfield, CT 06825
SOLD AUG 6, 2026
$1,375,000
B
6 beds3.5 baths3,655 sq ft
73 Inwood Rd, Fairfield, CT 06825
SOLD JAN 23, 2026
$1,230,000
C
5 beds3.5 baths2,976 sq ft
112 Eastwood Rd, Fairfield, CT 06825
SOLD AUG 28, 2026
$1,090,000
D
4 beds3 baths2,228 sq ft
1146 Valley Rd, Fairfield, CT 06825
SOLD SEP 16, 2026
$1,121,500
E
4 beds2.5 baths2,212 sq ft
400 Buena Vista Rd, Fairfield, CT 06825
SOLD OCT 2, 2026
$985,000
F
4 beds2.5 baths3,306 sq ft
205 Stoneleigh Sq, Fairfield, CT 06825

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$921,247

Est. take-home

List your home with Redfin and save $15,397

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$5,507/mo

Redfin rental estimate

List your home for rent

Market trends in 06825, CT

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

104.3%

+0.1% MoM

Median sale price

$800K

$50K MoM

Avg. days on market

42d

3 days MoM

Recently sold homes

23 MoM

New listings for sale

NEW 2 HRS AGO
$524,900
2 beds2 baths1,384 sq ft
85 Gate Ridge Rd #85, Fairfield, CT 06825
OPEN SUN, 12PM TO 2PM
$700,000
3 beds2.5 baths1,766 sq ft
71 Nichols Ave, Fairfield, CT 06825
OPEN TODAY, 11AM TO 2PM
$1,075,000
3 beds2.5 baths2,609 sq ft
292 Bullard St #292, Fairfield, CT 06825
OPEN SUN, 12PM TO 2PM
$649,900
3 beds3.5 baths2,002 sq ft
55 Blackmount Ct #55, Fairfield, CT 06825
OPEN SUN, 1PM TO 3PM
$1,199,000
4 beds2.5 baths3,786 sq ft
160 Brookview Ave, Fairfield, CT 06825
OPEN SUN, 1PM TO 4PM
$1,299,000
4 beds2.5 baths3,407 sq ft
285 Primrose Ln, Fairfield, CT 06825
COMING SOON
$585,000
3 beds1 bath912 sq ft
2105 Stratfield Rd, Fairfield, CT 06825
COMING SOON
$824,900
3 beds2 baths1,736 sq ft
50 Pansy Rd, Fairfield, CT 06824
$399,999
2 beds1 bath780 sq ft
14 Campfield Dr, Fairfield, CT 06825
$529,000
3 beds2 baths1,357 sq ft
2261 Easton Tpke, Fairfield, CT 06825
See all

Provided by Redfin

Sale history for 299 Toilsome Hill Rd

Join or sign in to view all info

Year

Property tax

Land + Additions

Assessment*

2023

$14,886 (+1.0%)

$254,940 + $286,160

$541,100

2022

$14,740 (+1.0%)

$254,940 + $286,160

$541,100

2021

$14,599 (−4.1%)

$254,940 + $286,160

$541,100

2020

$15,222 (+4.5%)

$256,690 + $311,500

$568,190

2019

$14,573 (+1.6%)

$256,690 + $287,280

$543,970

2018

$14,339 (+2.1%)

$256,690 + $287,280

$543,970

2017

$14,045 (+1.5%)

$256,690 + $287,280

$543,970

2016

$13,844 (+11.3%)

$256,690 + $287,280

$543,970

2014

$12,436

$282,380 + $227,290

$509,670

Tax history for 299 Toilsome Hill Rd

Year

Property tax

Land + Additions

Assessment*

2023

$14,886 (+1.0%)

$254,940 + $286,160

$541,100

2022

$14,740 (+1.0%)

$254,940 + $286,160

$541,100

2021

$14,599 (−4.1%)

$254,940 + $286,160

$541,100

2020

$15,222 (+4.5%)

$256,690 + $311,500

$568,190

2019

$14,573 (+1.6%)

$256,690 + $287,280

$543,970

2018

$14,339 (+2.1%)

$256,690 + $287,280

$543,970

2017

$14,045 (+1.5%)

$256,690 + $287,280

$543,970

2016

$13,844 (+11.3%)

$256,690 + $287,280

$543,970

2014

$12,436

$282,380 + $227,290

$509,670

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

3.5

Stories

Lot width

—

Lot depth

—

Lot size

0.54 Acres

Year renovated

—

Sq. Ft.

3,475

Year built

1930

Style

Single Family Residential

County

Fairfield County

APN

117961

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, Paved
Garages Number: 2

Interior

Interior Information
Total Rooms: 9
Laundry Room Info: Upper Level
In-Law Apartment: No
Fireplaces Total: 1
Cooling System: Central Air
Appliances Included: Gas Cooktop, Oven/Range, Range Hood, Refrigerator, Freezer, Dishwasher, Washer, Dryer

Bathroom Information
# of Baths (Full): 3
# of Baths (Half): 1

Bedroom Information
Beds Total: 5

Room Information
Room Count: 14
Basement Description: Unfinished, Concrete Floor, Hatchway Access
Has Attic

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Shake, Wood
Exterior Features: Gutters, Patio, Shed

Lot Information
Lot Description: Cleared, Level Lot, Lightly Wooded

Building Information
Foundation Type: Stone
Construction Description: Frame
Color: Tan

Property Information
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 3475
Driveway Type: Private, Paved

Financial

Assessments Information
Assessed Value: $543,970

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Public Sewer Connected
Hot Water Description: Tankless Hotwater
Heat Type: Hot Air
Heat Fuel Type: Natural Gas

Location

School Information
Middle Jr High School: Tomlinson
High School: Fairfield Warde
Elementary School: Stratfield

Location Information
State: Connecticut
Nearby Amenities: Basketball Court, Golf Course, Library, Park, Playground/Tot Lot, Public Transportation, Tennis Courts
Directions: Stratfield Rd to Toilsome Hill Rd
County: Fairfield

Public facts

Beds: 5
Baths: 3.5
Sq. Ft.: 3,475
Stories: 2.0
Lot Size: 0.54 acres
Style: Single Family Residential
Year Built: 1930
Year Renovated: —
County: Fairfield County
APN: 117961

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 1

Around this home

Schools

K - 12
Preschool & daycare

Stratfield School

Public PreK-5 • Assigned • 0.6mi

8/10

Tomlinson Middle School

Public 6-8 • Assigned • 4.1mi

7/10

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

5/10 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)

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

$1.46M – $1.77M

Reach more buyers when you sell with Redfin. Save up to $15,397 in fees. 3 minutes to get started.

Get a free, detailed breakdown of how we calculated your estimate.

Nearby similar homes

OPEN TODAY, 11AM TO 2PM

$1,075,000

3 beds2.5 baths2,609 sq ft

292 Bullard St #292, Fairfield, CT 06825

Hardwood floors • Quartz countertops • Large center island

$419,000

2 beds1 bath984 sq ft

43 Breyer Ave, Bridgeport, CT 06606

Remodeled • Crown moldings • Hardwood floors

$549,900

3 beds1.5 baths1,090 sq ft

33 Melville Ave, Fairfield, CT 06825

5,227 sq ft lot • 2 garage spots • Built 1924

3D WALKTHROUGH

$749,900

2 beds2 baths2,324 sq ft

1 Campfield Dr, Fairfield, CT 06825

Modern colonial • Chef's kitchen • Covered porch

$974,000

4 beds2.5 baths3,013 sq ft

211 Old Farm Rd, Fairfield, CT 06825

Updated kitchen • En-suite bath • New roof

$399,999

2 beds1 bath780 sq ft

14 Campfield Dr, Fairfield, CT 06825

Tiled shower • Grassy yard • Two storage sheds

New listings for sale in 06825

NEW 2 HRS AGO

$524,900

2 beds2 baths1,384 sq ft

85 Gate Ridge Rd #85, Fairfield, CT 06825

Ranch-style condo • Oversized windows • Eat-in kitchen

OPEN SUN, 12PM TO 2PM

$700,000

3 beds2.5 baths1,766 sq ft

71 Nichols Ave, Fairfield, CT 06825

New roof • New windows • 4,356 sq ft lot

OPEN TODAY, 11AM TO 2PM

$1,075,000

3 beds2.5 baths2,609 sq ft

292 Bullard St #292, Fairfield, CT 06825

Hardwood floors • Quartz countertops • Large center island

OPEN SUN, 12PM TO 2PM3D & VIDEO TOUR

$649,900

3 beds3.5 baths2,002 sq ft

55 Blackmount Ct #55, Fairfield, CT 06825

Brand-new roof • Sliders to balcony • $670 HOA

OPEN SUN, 1PM TO 3PM

$1,199,000

4 beds2.5 baths3,786 sq ft

160 Brookview Ave, Fairfield, CT 06825

Custom moldings • Mudroom addition • Brick floor

OPEN SUN, 1PM TO 4PM

$1,299,000

4 beds2.5 baths3,407 sq ft

285 Primrose Ln, Fairfield, CT 06825

Eat-in kitchen • Great room • Vaulted ceilings

COMING SOON

$585,000

3 beds1 bath912 sq ft

2105 Stratfield Rd, Fairfield, CT 06825

Huge lot • 4000 sf home • 0.71 acre lot

COMING SOON

$824,900

3 beds2 baths1,736 sq ft

50 Pansy Rd, Fairfield, CT 06824

Hardwood flooring • Bay window • Exposed beams

$399,999

2 beds1 bath780 sq ft

14 Campfield Dr, Fairfield, CT 06825

Tiled shower • Grassy yard • Two storage sheds

Home values near 299 Toilsome Hill Rd

Data from public records.

Address	Redfin Estimate
365 Toilsome Hill Rd, Fairfield, CT 4 Beds \| 3.5 Baths \| 3686 Sq. Ft.	$1,765,561
294 Toilsome Hill Rd, Fairfield, CT 4 Beds \| 3.5 Baths \| 2678 Sq. Ft.	$1,045,108
327 Toilsome Hill Rd, Fairfield, CT 4 Beds \| 2.5 Baths \| 2848 Sq. Ft.	$1,581,317
328 Toilsome Hill Rd, Fairfield, CT 5 Beds \| 4.5 Baths \| 3548 Sq. Ft.	$1,357,743
230 Toilsome Hill Rd, Fairfield, CT 4 Beds \| 2.5 Baths \| 2548 Sq. Ft.	$960,995
214 Inwood Rd, Fairfield, CT 4 Beds \| 3.5 Baths \| 3602 Sq. Ft.	$1,575,331
31 Brookridge Ave, Fairfield, CT 3 Beds \| 3 Baths \| 2066 Sq. Ft.	$594,334

Address	Redfin Estimate
298 Toilsome Hill Rd, Fairfield, CT 3 Beds \| 2.5 Baths \| 2010 Sq. Ft.	$1,060,136
370 Toilsome Hill Rd, Fairfield, CT 4 Beds \| 2.5 Baths \| 3440 Sq. Ft.	$1,363,199
258 Toilsome Hill Rd, Fairfield, CT 3 Beds \| 3.5 Baths \| 2219 Sq. Ft.	$1,041,714
360 Toilsome Hill Rd, Fairfield, CT 4 Beds \| 2.5 Baths \| 2621 Sq. Ft.	$950,308
219 Toilsome Hill Rd, Fairfield, CT 5 Beds \| 3 Baths \| 3125 Sq. Ft.	$1,437,160
227 Windermere St, Fairfield, CT 3 Beds \| 2.5 Baths \| 1936 Sq. Ft.	$862,412
230 Inwood Rd, Fairfield, CT 4 Beds \| 3 Baths \| 2119 Sq. Ft.	$1,425,612

Address	Redfin Estimate
393 Toilsome Hill Rd, Fairfield, CT 5 Beds \| 2.5 Baths \| 3040 Sq. Ft.	$1,258,260
341 Toilsome Hill Rd, Fairfield, CT 5 Beds \| 3.5 Baths \| 3758 Sq. Ft.	$1,569,672
261 Toilsome Hill Rd, Fairfield, CT 4 Beds \| 2.5 Baths \| 2856 Sq. Ft.	$1,213,405
279 Toilsome Hill Rd, Fairfield, CT 3 Beds \| 3 Baths \| 2940 Sq. Ft.	$1,250,365
239 Toilsome Hill Rd, Fairfield, CT 5 Beds \| 3.5 Baths \| 3609 Sq. Ft.	$1,413,021
215 Windermere St, Fairfield, CT 3 Beds \| 1 Baths \| 1085 Sq. Ft.	$645,923
180 Inwood Rd, Fairfield, CT 5 Beds \| 6 Baths \| 4966 Sq. Ft.	$1,706,720

Property information provided by Smart MLS when last listed in 2019. This data may not match . Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

Redfin Brokerage Licenses

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

Houses for rent in Fairfield County	Agents near me	Westport, CT homes for sale	Fairfield County Housing Market
Houses for sale near me	Greenwich, CT homes for sale	New Haven, CT homes for sale
Land for sale near me	Stamford, CT homes for sale	Milford, CT homes for sale
Open Houses near me	West Hartford, CT homes for sale	Fairfield County Property Records
Condos for sale near me	Norwalk, CT homes for sale	CT New Listings

Westchester County homes for sale
Bergen County homes for sale
Nassau County homes for sale

Greenwich homes for sale
Milford homes for sale
Stamford homes for sale

About this home

Redfin Estimate

Earn from this home

Market trends in 06825, CT

Sale history for 299 Toilsome Hill Rd

Tax history for 299 Toilsome Hill Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06825

Home values near 299 Toilsome Hill Rd

More real estate resources