Off Market Oct 2021 for $1.1M

$1,639,659

Est. refi paymentEst. refi $3,918/mo

•

4,716

sq ft

27 Chestnut Hill Rd, Madison, CT 06443

About this home

Exceptional detail throughout this custom colonial.Brazilian cherry floors,crown molding,antique tin ceiling in family room,3 fireplaces,media room, rec room, studio over 3 car garage, inground pool, large stone patio with outdoor cooking area. Close to town and beaches yet still offers very private grounds. The kitchen has a 10 foot long island/breakfast bar,wolf and sub zero appliances, large windows for plenty of natural light. Additional square footage not listed for office or guest bedroom. Tremendous layout for entertaining or just relaxing in your own hideaway

Single-familyProperty Type

2004Year Built

2.15 acresLot Size

$348Est. Price/Sq.Ft.

3 car garageParking

Listed by Bob Allison • William Pitt Sotheby's Int'l

Bought with Laurie Trulock • Compass Connecticut, LLC

Source:Smart MLS #170419996

Redfin Estimate

$1,639,659

$540K since sold in October 2021$38K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 47.2% higher than the average sale price ($1.11M) of 6 comparable homes.

SOLD AUG 18, 2026
$895,000
A
4 beds3.5 baths3,165 sq ft
10 Grace Ln, Killingworth, CT 06419
SOLD AUG 17, 2026
$1,250,000
B
4 beds3.5 baths4,806 sq ft
34 Beekman Pl, Madison, CT 06443
SOLD JUL 23, 2026
$1,200,000
C
4 beds3.5 baths4,250 sq ft
86 Nursery Ln, Madison, CT 06443
SOLD AUG 27, 2026
$1,550,000
D
4 beds3.5 baths4,673 sq ft
11 Timber Ln, Guilford, CT 06437
SOLD FEB 2, 2026
$855,000
E
4 beds3 baths3,972 sq ft
23 Horsebarn Ln, Madison, CT 06443
SOLD MAY 29, 2026
$931,500
F
4 beds3.5 baths3,581 sq ft
21 Running Brook Dr, Killingworth, CT 06419

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Earn from this home

Sell

$746,458

Est. take-home

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Refinance

Est. cash available

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Rent

$5,199/mo

Redfin rental estimate

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Market trends in 06443, CT

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

102.4%

+0.4% MoM

Median sale price

$797K

$2K MoM

Avg. days on market

43d

1 days MoM

Recently sold homes

6 MoM

New listings for sale

OPEN SUN, 2PM TO 4PM
$500,000
2 beds2 baths1,280 sq ft
14 Hampshire Rd #14, Madison, CT 06443
OPEN SUN, 10AM TO 12PM
$1,200,000
4 beds4 baths2,354 sq ft
148 Mungertown Rd, Madison, CT 06443
COMING SOON
$489,000
2 beds2.5 baths1,606 sq ft
23 Esterly Farms Rd #23, Madison, CT 06443
$500,000
3 beds2.5 baths1,824 sq ft
18 Saint Francis Woods Rd, Madison, CT 06443
$700,000
3 beds2.5 baths2,124 sq ft
67 Blakeman Rd, Madison, CT 06443
$579,900
3 beds1 bath1,077 sq ft
6 Bower Rd, Madison, CT 06443
$5,000,000
3 beds3 baths3,109 sq ft
118 River Rd, Madison, CT 06443
See all

Provided by Redfin

Sale history for 27 Chestnut Hill Rd

Date

Event

Price

Smart MLS #170419996

Oct 12, 2021

Sold

$1,100,000

$233/sq ft

Aug 24, 2021

Contingent

—

Jul 17, 2021

Listed

$1,250,000

$265/sq ft

Jul 15, 2021

Coming Soon

$1,250,000

$265/sq ft

Smart MLS #M9138793

Jul 12, 2013

Sold

$962,500

$204/sq ft

Feb 8, 2013

Listed

$1,150,000

$244/sq ft

Majestically situated on a hilltop this home offers exquisite attention to detail. This stately colonials foyer takes center stage w/granite floors, 2 story spiral staircase and crystal chandelier. Light filled rooms and open concept add an air of ease. The kitchen greets us with a 10 foot breakfast bar, built in buffet, sub zero refr, wolf ovens and warming tray. A pleasure to cook or casually entertain in.The sunroom offers a skylight, atrium to the outdoor living space and a cozy firplc. The kitchen opens to the family room through decorative pillars, a stone frplc and atrium doors to the patio are perfect for summer and winter entertaining. The finished basement is all about fun and relaxation. The 4 bedrooms are located on the 2nd level with 3 full bathrooms. A handsome guest suite adds the 5th bedroom, full bath and an office / sitting room and offers approx. 600 Additional square feet not inlcuded in total sf. Private patio, pool and spa add to the enjoyment this home offers.

Public Records

Sep 23, 2008

Sold

$1,200,000

$254/sq ft

Smart MLS #M9104601

Jun 5, 2007

Listed

$1,295,000

$275/sq ft

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Year

Property tax

Land + Additions

Assessment*

2023

$18,521 (+1.9%)

$89,400 + $528,600

$618,000

2022

$18,175 (+1.9%)

$89,400 + $528,600

$618,000

2021

$17,829 (+1.8%)

$89,400 + $528,600

$618,000

2020

$17,520

$89,400 + $528,600

$618,000

2019

$17,520 (−1.3%)

$89,400 + $528,600

$618,000

2018

$17,755 (+2.7%)

$92,000 + $541,200

$633,200

2017

$17,286 (+3.1%)

$92,000 + $541,200

$633,200

2016

$16,773 (+5.2%)

$92,000 + $541,200

$633,200

2014

$15,938 (+12.8%)

$92,000 + $541,200

$633,200

2010

$14,132

$151,600 + $541,500

$693,100

Tax history for 27 Chestnut Hill Rd

Year

Property tax

Land + Additions

Assessment*

2023

$18,521 (+1.9%)

$89,400 + $528,600

$618,000

2022

$18,175 (+1.9%)

$89,400 + $528,600

$618,000

2021

$17,829 (+1.8%)

$89,400 + $528,600

$618,000

2020

$17,520

$89,400 + $528,600

$618,000

2019

$17,520 (−1.3%)

$89,400 + $528,600

$618,000

2018

$17,755 (+2.7%)

$92,000 + $541,200

$633,200

2017

$17,286 (+3.1%)

$92,000 + $541,200

$633,200

2016

$16,773 (+5.2%)

$92,000 + $541,200

$633,200

2014

$15,938 (+12.8%)

$92,000 + $541,200

$633,200

2010

$14,132

$151,600 + $541,500

$693,100

*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

4.5

Stories

Lot width

—

Lot depth

—

Lot size

2.15 Acres

Year renovated

—

Sq. Ft.

4,716

Year built

2004

Style

Single Family Residential

County

New Haven County

APN

2467032

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 12, 2023.

Property details

Parking

Garage Information
Garage & Parking: Attached Garage, Security
Garages Number: 3

Interior

Virtual Tour Information
Has Virtual Tour

Interior Information
Total Rooms: 9
Laundry Room Info: Upper Level
Interior Features: Audio System, Auto Garage Door Opener, Cable - Pre-wired, Open Floor Plan, Security System
In-Law Apartment: Possible
In-Law Access: Over Garage
Security System, Thermostat(s)
Fireplaces Total: 3
Cooling System: Ceiling Fans, Central Air
Appliances Included: Oven/Range, Microwave, Range Hood, Refrigerator, Dishwasher, Disposal

Bathroom Information
# of Baths (Full): 4
# of Baths (Half): 1

Bedroom Information
Beds Total: 4

Room Information
Room Count: 12
Basement Description: Full With Walk-Out, Fully Finished, Heated, Cooled
Has Attic
Attic Description: Walk-up

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Stone, Wood
Exterior Features: Balcony, Cabana, French Doors, Garden Area, Gazebo, Grill, Lighting, Patio, Shed

Lot Information
Lot Description: Dry

Pool Information
Swimming Pool
Pool Description: In Ground Pool, Salt Water, Safety Fence

Building Information
Foundation Type: Concrete
Construction Description: Stone
Color: Stone

Property Information
Waterfront Description: Beach
Radon Mitigation Air
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 4716
Driveway Type: Private, Paved

Financial

Assessments Information
Assessed Value: $618,000

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: 50 Gallon Tank, Electric
Heat Type: Hot Air, Zoned
Heat Fuel Type: Oil
Fuel Tank Location: In Basement
Energy Features: Thermopane Windows

Location

School Information
Middle Jr High School: Per Board of Ed
Intermediate School: Per Board of Ed
High School: Daniel Hand
Elementary School: Per Board of Ed

Location Information
State: Connecticut
Nearby Amenities: Golf Course, Health Club, Library, Medical Facilities, Private School(s), Shopping/Mall, Stables/Riding, Tennis Courts
Directions: Route 79 to Chestnut Hill Rd--turn right--house is on the left
County: New Haven

Public facts

Beds: 4
Baths: 4.5
Sq. Ft.: 4,716
Stories: 2.0
Lot Size: 2.15 acres
Style: Single Family Residential
Year Built: 2004
Year Renovated: —
County: New Haven County
APN: 2467032

Home facts updated by county records on Jul 12, 2023

Other

Documents & Disclosures
Supplement Count Public: 2

Around this home

Schools

Dr. Robert H. Brown Middle School

Public 4-5 • Assigned • 1.2mi

9/10

Walter C. Polson Upper Middle School

Public 6-8 • Assigned • 2.1mi

9/10

Daniel Hand High School

Public 9-12 • Assigned • 2.3mi

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

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

6/10 Heat Factor

7 days above 93° expected this year, 17 days in 30 years

6/10 Wind Factor

71% chance of strong winds in next 30 years

5/10 Air Factor

5 unhealthy days expected this year, 8 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 9 hours in June and 4.5 hours in December, which is comparable to the U.S. average for solar exposure.

9 hrs

4.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.56M – $1.89M

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New listings for sale in 06443

OPEN SUN, 2PM TO 4PM

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COMING SOON

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Home values near 27 Chestnut Hill Rd

Data from public records.

Address	Redfin Estimate
41 Chestnut Hill Road, Madison, CT 4 Beds \| 3.5 Baths \| 3926 Sq. Ft.	$1,049,797
24 Chestnut Hill Road, Madison, CT 4 Beds \| 3.5 Baths \| 4026 Sq. Ft.	$953,428

Address	Redfin Estimate
10 Chestnut Hill Road, Madison, CT 4 Beds \| 2.5 Baths \| 2052 Sq. Ft.	$713,679
30 Chestnut Hill Road, Madison, CT 3 Beds \| 2.5 Baths \| 2071 Sq. Ft.	$714,929

Address	Redfin Estimate
40 Chestnut Hill Road, Madison, CT 3 Beds \| 3 Baths \| 2435 Sq. Ft.	$862,102
57 Chestnut Hill Road, Madison, CT 4 Beds \| 2.5 Baths \| 2335 Sq. Ft.	$656,106

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

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