Off market aug 2021 for $500K

$755,236

Est. refi paymentEst. refi $3,825/mo

•

2,576

sq ft

299 Old Toll Rd, Madison, CT 06443

About this home

This spacious home is tucked back from route 80 making commuting a dream. For the busy individuals you are close to commuting roads whether heading to New Haven or Middletown. You are also close to Chatfield Hollow State Park for hiking, picnics, swimming, and fishing. Roberts Food Center; a well respected grocery store with recipes of the week to help break up the weekly grind of meal preparation along with several restaurants within a stones throw. The home offers an expansive floor plan while providing definition of space. There are plenty of quiet spaces giving one the ability to work from home or home school. The kitchen has an oversized granite island; spacious for entertaining. The first floor is also equipped with a generously sized bedroom with double closets and an accessible full bath across the hallway. There is hardwood flooring throughout the first floor. The family room has doors of glass giving a view of the oversized concrete pool; a serene vista which is both inviting and refreshing. The pool receives direct sunlight. There is also a gas heater to warm the temperature to extend seasonal use. The second floor is accessed by double staircases on either end of the home. The expansive second floor hallway offers tidy spaces for reading, artwork, or additional space as you envision. There are four bedrooms, one being an ensuite master bedroom. The roof line and dormered windows add to the architectural details of the second floor.

Single-familyProperty Type

1977Year Built

1.5 acresLot Size

$293Est. Price/Sq.Ft.

2 car garageParking

Listed by Heather Clinton • Berkshire Hathaway NE Prop.

Bought with Phoebe Finch • William Pitt Sotheby's Int'l

Source:Smart MLS #170408052

Redfin Estimate

$755,236

$255K since sold in August 2021$12K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 6.8% lower than the average sale price ($811K) of 6 comparable homes.

SOLD OCT 15, 2026
$660,000
A
4 beds2.5 baths2,536 sq ft
320 Summer Hill Rd, Madison, CT 06443
SOLD AUG 20, 2026
$769,000
B
4 beds2.5 baths2,647 sq ft
89 Summer Hill Rd, Madison, CT 06443
SOLD JUL 10, 2026
$635,000
C
4 beds2.5 baths2,108 sq ft
112 Barnshed Ln, Guilford, CT 06437
SOLD JUL 24, 2026
$850,000
D
4 beds2.5 baths2,665 sq ft
51 Country Way, Madison, CT 06443
SOLD SEP 1, 2026
$1,250,000
E
4 beds3 baths3,816 sq ft
128 Concord Dr, Madison, CT 06443
SOLD AUG 10, 2026
$700,000
F
4 beds2.5 baths2,057 sq ft
476 Summer Hill Rd, Madison, CT 06443

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Sell

$349,801

Est. take-home

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Est. cash available

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Rent

$3,936/mo

Redfin rental estimate

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Market trends in 06443, CT

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

102.7%

+0.4% MoM

Median sale price

$799K

$6K MoM

Avg. days on market

38d

5 days MoM

Recently sold homes

2 MoM

New listings for sale

$1,779,000
3 beds2.5 baths2,566 sq ft
16 North Ave, Madison, CT 06443
$499,900
3 beds2 baths1,994 sq ft
8 Stephanie Ct, Madison, CT 06443
OPEN SUN, 12PM TO 1:30PM
$499,900
3 beds3 baths1,944 sq ft
25 Samantha Ln, Madison, CT 06443
COMING SOON
$1,299,000
5 beds3.5 baths4,723 sq ft
37 Silo Hl, Madison, CT 06443
$549,900
4 beds2 baths1,728 sq ft
252 Boston Post Rd, Madison, CT 06443
$275,000
2 beds1 bath751 sq ft
59 EAST St, Madison, CT 06434
$550,000
2 beds2 baths1,316 sq ft
91 Neck Rd, Madison, CT 06443
$550,000
2 beds2 baths1,280 sq ft
23 Wilshire Rd Unit A, Madison, CT 06443
$665,000
3 beds2.5 baths2,237 sq ft
3 Poole Rd, Madison, CT 06443
See all

Provided by Redfin

Sale history for 299 Old Toll Rd

Date

Event

Price

Smart MLS #170408052

Aug 30, 2021

Sold

$500,000

$194/sq ft

Jun 23, 2021

Contingent

—

Jun 10, 2021

Listed

$525,000

$204/sq ft

Smart MLS #170383323

Jun 8, 2021

Listing Removed

—

May 17, 2021

Price Changed

$549,000

$213/sq ft

Apr 5, 2021

Listed

$599,000

$233/sq ft

Smart MLS #170017493

Jan 31, 2018

Sold

$315,000

$122/sq ft

Dec 21, 2017

Pending

—

Dec 18, 2017

Listed

—

Sep 27, 2017

Listed

$339,000

$132/sq ft

Priced to sell! Custom from top to bottom 4-5 bed 2.0 bath home is a spectacular built cape/farm house style home w/high end features throughout that is truly a special property. Gleaming refinished hardwood floors, jetted & heated tub, separate stand up shower, double vanities, separate toilet including bidet. The spacious & light filled brand new open concept eat in kitchen w/new cabinets w/self closing drawers, granite, new high end stainless steel appliances including VIKING stove, huge central island w/built in cook top & hood along w/ breakfast bar, cabinets and seating. The kitchen flows into the dining area and living room with fireplace. A door leads to the large back deck overlooking the private yard which features a INGROUND POOL with new pool system and filter. The first floor features a bedroom & renovated full bathroom, an office nook/library & then a second family/living room w/sliders to the pool. The Second floor features 4 more bedrooms, including a large master bedroom with walk in closet and another renovated full bathroom. Additionally, home features a new roof, gleaming refinished hardwood flooring w/an attached 2/3 car garage & a huge basement w/separate room & plumbing for a full bathroom. You will be impressed with how this home has been impeccably re-designed. Not a thing to do but enjoy your better than new home. This luxury home conveniently located w/easy access to shopping, highways, restaurants, parks, downtown New Haven, Yale, Southern & more.

Smart MLS #M9136081

Apr 10, 2013

Sold

$228,000

$89/sq ft

Aug 1, 2012

Listed

$250,000

$97/sq ft

Smart MLS #N300272

Sep 17, 2010

Listing Removed

—

Mar 17, 2010

Listed

$325,000

$126/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$7,328 (+1.9%)

$85,200 + $159,300

$244,500

2022

$7,191 (+1.9%)

$85,200 + $159,300

$244,500

2021

$7,054 (+1.8%)

$85,200 + $159,300

$244,500

2020

$6,932

$85,200 + $159,300

$244,500

2019

$6,932 (−1.3%)

$85,200 + $159,300

$244,500

2018

$7,021 (+2.7%)

$83,500 + $166,900

$250,400

2017

$6,836 (+3.1%)

$83,500 + $166,900

$250,400

2016

$6,633 (+5.2%)

$83,500 + $166,900

$250,400

2014

$6,303 (+15.3%)

$83,500 + $166,900

$250,400

2010

$5,465

$113,900 + $154,100

$268,000

Tax history for 299 Old Toll Rd

Year

Property tax

Land + Additions

Assessment*

2023

$7,328 (+1.9%)

$85,200 + $159,300

$244,500

2022

$7,191 (+1.9%)

$85,200 + $159,300

$244,500

2021

$7,054 (+1.8%)

$85,200 + $159,300

$244,500

2020

$6,932

$85,200 + $159,300

$244,500

2019

$6,932 (−1.3%)

$85,200 + $159,300

$244,500

2018

$7,021 (+2.7%)

$83,500 + $166,900

$250,400

2017

$6,836 (+3.1%)

$83,500 + $166,900

$250,400

2016

$6,633 (+5.2%)

$83,500 + $166,900

$250,400

2014

$6,303 (+15.3%)

$83,500 + $166,900

$250,400

2010

$5,465

$113,900 + $154,100

$268,000

*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

Stories

Lot width

—

Lot depth

—

Lot size

1.5 Acres

Year renovated

—

Sq. Ft.

2,576

Year built

1977

Style

Single Family Residential

County

New Haven County

APN

1160651

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Parking

Garage Information
Garage & Parking: Under House Garage
Garages Number: 2

Interior

Virtual Tour Information
Has Virtual Tour

Interior Information
Total Rooms: 8
Laundry Room Info: Lower Level
Interior Features: Cable - Pre-wired, Open Floor Plan
Fireplaces Total: 1
Cooling System: Ceiling Fans, Window Unit
Appliances Included: Electric Cooktop, Electric Range, Range Hood, Refrigerator, Freezer, Icemaker, Dishwasher, Washer, Electric Dryer

Bathroom Information
# of Baths (Full): 3

Bedroom Information
Beds Total: 5

Room Information
Room Count: 11
Basement Description: Unfinished, Concrete Floor

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Wood
Exterior Features: Deck, Garden Area, Patio, Shed

Lot Information
Lot Description: Lightly Wooded, Sloping Lot, Fence - Partial

Pool Information
Swimming Pool
Pool Description: In Ground Pool, Heated, Concrete

Building Information
Foundation Type: Block
Construction Description: Frame, Block
Color: Blue

Property Information
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 2576

Financial

Assessments Information
Assessed Value: $244,500

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Oil
Heat Type: Baseboard, Hot Water
Heat Fuel Type: Oil
Fuel Tank Location: In Basement
Energy Features: Ridge Vents, Storm Doors, Thermopane Windows

Location

School Information
Middle Jr High School: Polson
Intermediate School: Per Board of Ed
High School: Daniel Hand
Elementary School: Kathleen H. Ryerson

Location Information
State: Connecticut
Nearby Amenities: Basketball Court, Golf Course, Library, Medical Facilities, Playground/Tot Lot, Private School(s), Shopping/Mall, Stables/Riding
Directions: From I95 take Rt 79(Durham Rd) North to rotary. Take route 80 towards Guilford. Home is on the right, hidden, across from Hickory Lane on the left. From Durham Rd North head South to rotary. Take rt. 80 towards Guilford.
County: New Haven

Public facts

Beds: 5
Baths: 2.0
Sq. Ft.: 2,576
Stories: 1.0
Lot Size: 1.5 acres
Style: Single Family Residential
Year Built: 1977
Year Renovated: —
County: New Haven County
APN: 1160651

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

Kathleen H. Ryerson Elementary School

Public K-3 • Assigned • 1.8mi

Walter C. Polson Upper Middle School

Public 6-8 • Assigned • 4.6mi

10/10

Daniel Hand High School

Public 9-12 • Assigned • 4.7mi

10/10

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

3/10 Fire Factor

0.62% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 days above 94° expected this year, 17 days in 30 years

6/10 Wind Factor

67% chance of strong winds in next 30 years

4/10 Air Factor

4 unhealthy days expected this year, 5 days in 30 years

Provided by First Street

Historical weather

Madison, CT • 06443

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 8.9 hours in June and 4.5 hours in December, which is comparable to the U.S. average for solar exposure.

8.9 hrs

4.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$718,000 – $869,000

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Home values near 299 Old Toll Rd

Data from public records.

Address	Redfin Estimate
331 Old Toll Rd, Madison, CT 4 Beds \| 2 Baths \| 2528 Sq. Ft.	$668,544
283 Old Toll Rd, Madison, CT 6 Beds \| 4 Baths \| 4466 Sq. Ft.	$759,437
271 Old Toll Rd, Madison, CT 3 Beds \| 2 Baths \| 2478 Sq. Ft.	$609,059
293 Old Toll Rd, Madison, CT 4 Beds \| 2 Baths \| 1150 Sq. Ft.	$662,269
26 Walnut Hill Rd, Madison, CT 3 Beds \| 2.5 Baths \| 1899 Sq. Ft.	$634,592
10 Walnut Hill Rd, Madison, CT 5 Beds \| 3.5 Baths \| 3500 Sq. Ft.	$1,048,718
15 Hickory Ln, Madison, CT 3 Beds \| 3 Baths \| 1902 Sq. Ft.	$597,411

Address	Redfin Estimate
305 Old Toll Rd, Madison, CT 3 Beds \| 1 Baths \| 1414 Sq. Ft.	$455,764
281 Old Toll Rd, Madison, CT 2 Beds \| 1 Baths \| 950 Sq. Ft.	$377,064
295 Old Toll Rd, Madison, CT 4 Beds \| 3 Baths \| 2440 Sq. Ft.	$501,830
247B Old Toll Rd, Madison, CT 3 Beds \| 1 Baths \| 1340 Sq. Ft.	$508,149
20 Walnut Hill Rd, Madison, CT 4 Beds \| 2.5 Baths \| 2758 Sq. Ft.	$717,011
22 Walnut Hill Rd, Madison, CT 4 Beds \| 5.5 Baths \| 2712 Sq. Ft.	$950,137
6 Hickory Ln, Madison, CT 3 Beds \| 1.5 Baths \| 1356 Sq. Ft.	$594,064

Address	Redfin Estimate
267 Old Toll Rd, Madison, CT 2 Beds \| 2 Baths \| 1505 Sq. Ft.	$479,844
269 Old Toll Rd, Madison, CT 2 Beds \| 2.5 Baths \| 3254 Sq. Ft.	$802,229
289 Old Toll Rd, Madison, CT 10 Beds \| 3 Baths \| 3039 Sq. Ft.	—
31 Hickory Ln, Madison, CT 3 Beds \| 2 Baths \| 1224 Sq. Ft.	$592,671
18 Walnut Hill Rd, Madison, CT 4 Beds \| 2.5 Baths \| 2840 Sq. Ft.	$921,022
5 Hickory Ln, Madison, CT 3 Beds \| 1.5 Baths \| 1132 Sq. Ft.	$466,079
3 Walnut Hill Rd, Madison, CT 3 Beds \| 1.5 Baths \| 1368 Sq. Ft.	$481,933

Property information provided by Smart MLS when last listed in 2021. This data may not match . Learn more.

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