Off Market Nov 2022 for $1.8M

$2,054,534

Est. refi paymentEst. refi $11,680/mo

•

4,956

sq ft

383 Boston Post Rd, Madison, CT 06443

About this home

SEEKING A PRIVATE 5 BEDROOM HOME CLOSE TO TOWN? Situated in one of the nicest enclaves in Madison, complete with natural gas heat and public water, this Peter Smith built home offers an open floor plan with over 5000sf of living space. The first floor hosts a stylish Kitchen with granite counters, stainless appliances and island. The inviting Family Room overlooks the backyard and offers a gas fireplace with filed stone surround. Adjacent to the Kitchen, is the elegant and oversized Dining Room. To complete the 1st floor, there is a bedroom (with full bath) for those that seek one level living. The 2nd floor is home to 4 other bedrooms, including the an immaculate Master Suite. The bonus room, over the garage, is perfect for any combination of play space, gym, office or even movie theater! The 3 acre "rectangular" lot offers tons of privacy. Additional features include: a new eco finish gunite heated pool, with spa feature, upgraded surround patio (cleaned, stained and resealed), new roof, new driveway, fenced in pool area, full house generator and professional landscaping. This home provides LOADS of privacy, but is close to downtown Madison, the Madison Country Club and the Madison Surf Club. The house has all the bells and whistles and offers the discerning Buyer everything they may be seeking. Come see.

Single-familyProperty Type

1999Year Built

3 acresLot Size

$415Est. Price/Sq.Ft.

3 garage spacesParking

Listed by Kirsten Adams • William Pitt Sotheby's Int'l

Bought with Kevin Geysen • William Pitt Sotheby's Int'l

Source:Smart MLS #170526688

Redfin Estimate

$2,054,534

$255K since sold in November 2022$19K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 26.7% higher than the average sale price ($1.62M) of 6 comparable homes.

SOLD JUL 15, 2026
$2,310,000
A
4 beds4 baths3,926 sq ft
36 Cedar Ln, Madison, CT 06443
SOLD FEB 19, 2026
$1,024,400
B
5 beds4.5 baths4,829 sq ft
214 Nortontown Rd, Guilford, CT 06437
SOLD MAY 18, 2026
$1,310,000
C
4 beds2.5 baths4,910 sq ft
11 Kachina Way, Madison, CT 06443
SOLD MAR 24, 2026
$925,000
D
4 beds3 baths5,624 sq ft
38 Sportsman Hill Rd, Madison, CT 06443
SOLD AUG 17, 2026
$2,495,000
E
4 beds2.5 baths3,321 sq ft
81A Middle Beach Rd, Madison, CT 06443
SOLD JUL 7, 2026
$1,665,000
F
5 beds5.5 baths5,380 sq ft
34 Wildcat Springs Dr, Madison, CT 06443

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Earn from this home

Sell

$597,519

Est. take-home

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Refinance

Est. cash available

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Rent

$5,078/mo

Redfin rental estimate

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Market trends in 06443, CT

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

100.6%

+0.1% MoM

Median sale price

$731K

$26K MoM

Avg. days on market

45d

6 days MoM

Recently sold homes

15 MoM

New listings for sale

OPEN SUN, 12PM TO 2PM
$735,000
4 beds2.5 baths2,614 sq ft
450 County Rd, Madison, CT 06443
$1,700,000
3 beds3 baths2,674 sq ft
50 Webster Point Rd, Madison, CT 06443
COMING SOON
$700,000
3 beds2.5 baths2,124 sq ft
67 Blakeman Rd, Madison, CT 06443
COMING SOON
$5,000,000
3 beds3 baths3,109 sq ft
Madison, CT 06443
OPEN SUN, 1PM TO 3PM
$524,000
3 beds2 baths1,288 sq ft
35 Aileen Dr, Madison, CT 06443
$500,000
2 beds2 baths1,280 sq ft
22 Thelbridge St #22, Madison, CT 06443
COMING SOON
$4,499,000
6 beds6.5 baths5,817 sq ft
14 Middle Beach Rd W, Madison, CT 06443
$3,000,000
4 beds5 baths4,833 sq ft
17 Barberry Ln, Madison, CT 06443
See all

Provided by Redfin

Sale history for 383 Boston Post Rd

Date

Event

Price

Smart MLS #170526688

Nov 18, 2022

Sold

$1,800,000

$363/sq ft

Oct 20, 2022

Contingent

—

Oct 2, 2022

Listed

$2,000,000

$404/sq ft

Sep 28, 2022

Coming Soon

$2,000,000

$404/sq ft

Smart MLS #170276580

May 19, 2020

Listing Removed

—

Feb 28, 2020

Listed

$1,149,000

$232/sq ft

Smart MLS #170201209

Jan 18, 2020

Listing Removed

—

May 31, 2019

Listed

$1,200,000

$242/sq ft

Smart MLS #170157494

May 31, 2019

Listing Removed

—

Jan 21, 2019

Listed

$1,225,000

$247/sq ft

Public Records

Dec 3, 2012

Sold

$1,050,000

$212/sq ft

Smart MLS #M9136459

Aug 21, 2012

Listed

$1,100,000

$222/sq ft

Smart MLS #M9126822

Aug 8, 2011

Listing Removed

—

Mar 14, 2011

Listed

$1,579,000

$319/sq ft

Smart MLS #M9120615

Nov 9, 2010

Listing Removed

—

Feb 9, 2010

Listed

$1,800,000

$363/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$22,013 (+1.9%)

$197,700 + $536,800

$734,500

2022

$21,602 (+1.9%)

$197,700 + $536,800

$734,500

2021

$21,190 (+1.8%)

$197,700 + $536,800

$734,500

2020

$20,823

$197,700 + $536,800

$734,500

2019

$20,823 (+7.6%)

$197,700 + $536,800

$734,500

2018

$19,350 (+2.7%)

$157,700 + $532,400

$690,100

2017

$18,840 (+3.1%)

$157,700 + $532,400

$690,100

2016

$18,281 (+5.2%)

$157,700 + $532,400

$690,100

2014

$17,370 (−28.6%)

$157,700 + $532,400

$690,100

2010

$24,344

$447,700 + $746,200

$1,193,900

Tax history for 383 Boston Post Rd

Year

Property tax

Land + Additions

Assessment*

2023

$22,013 (+1.9%)

$197,700 + $536,800

$734,500

2022

$21,602 (+1.9%)

$197,700 + $536,800

$734,500

2021

$21,190 (+1.8%)

$197,700 + $536,800

$734,500

2020

$20,823

$197,700 + $536,800

$734,500

2019

$20,823 (+7.6%)

$197,700 + $536,800

$734,500

2018

$19,350 (+2.7%)

$157,700 + $532,400

$690,100

2017

$18,840 (+3.1%)

$157,700 + $532,400

$690,100

2016

$18,281 (+5.2%)

$157,700 + $532,400

$690,100

2014

$17,370 (−28.6%)

$157,700 + $532,400

$690,100

2010

$24,344

$447,700 + $746,200

$1,193,900

*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

3 Acres

Year renovated

—

Sq. Ft.

4,956

Year built

1999

Style

Single Family Residential

County

New Haven County

APN

1155673

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: 3

Parking Information
Parking Total Spaces: 8

Interior

Virtual Tour Information
Has Virtual Tour

Interior Information
Total Rooms: 10
Laundry Room Location: 2nd floor
Laundry Room Info: Upper Level
Interior Features: Auto Garage Door Opener, Cable - Available, Security System
Fireplaces Total: 1
Cooling System: Central Air
Appliances Included: Gas Cooktop, Oven/Range, Microwave, Subzero, Dishwasher, Compactor, Washer, Dryer, Wine Chiller

Bathroom Information
# of Baths (Full): 4

Bedroom Information
Beds Total: 5

Room Information
Rooms Additional: Foyer, Laundry Room, Mud Room
Room Count: 9
Basement Description: Full With Hatchway, Unfinished, Concrete Floor, Garage Access, Storage
Has Attic
Attic Description: Pull-Down Stairs

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Wood
Exterior Features: Deck, French Doors, Garden Area, Gutters, Patio, Stone Wall, Underground Sprinkler

Lot Information
Lot Description: On Cul-De-Sac, In Subdivision, Lightly Wooded, Sloping Lot, Fence - Full, Professionally Landscaped

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

Building Information
Foundation Type: Concrete
Construction Description: Frame, Concrete
Color: Taupe

Property Information
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 4956
Driveway Type: Private, Paved

Financial

Assessments Information
Assessed Value: $734,500

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Septic
Hot Water Description: Natural Gas
Heat Type: Hot Air, Zoned
Heat Fuel Type: Natural Gas
Fuel Tank Location: In Basement
Energy Features: Generator, Thermopane Windows

Location

HOA Information
Has Home Owner's Assocation
HOA Fee Frequency: Annually
HOA Fee Amount: $1,000
Association Fee Includes: Grounds Maintenance, Snow Removal

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

Location Information
Subdivision: Leatherman's Hill
State: Connecticut
Nearby Amenities: Golf Course, Library, Medical Facilities, Private School(s), Public Transportation, Shopping/Mall
Directions: Rt 1 / Boston Post Road to Leatherman's Hill (across from Lowery Field) #383 is the last one at the end of the street.
County: New Haven

Public facts

Beds: 5
Baths: 4.0
Sq. Ft.: 4,956
Stories: 2.0
Lot Size: 3 acres
Style: Single Family Residential
Year Built: 1999
Year Renovated: —
County: New Haven County
APN: 1155673

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 4

Around this home

Schools

J. Milton Jeffrey Elementary School

Public K-3 • Assigned • 1.0mi

10/10

Walter C. Polson Upper Middle School

Public 6-8 • Assigned • 1.0mi

9/10

Daniel Hand High School

Public 9-12 • Assigned • 0.9mi

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, 18 days in 30 years

8/10 Wind Factor

80% 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

$1.95M – $2.36M

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New listings for sale in 06443

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Home values near 383 Boston Post Rd

Data from public records.

Address	Redfin Estimate
381 Boston Post Rd, Madison, CT 4 Beds \| 5 Baths \| 5918 Sq. Ft.	$1,908,501
395 Boston Post Rd, Madison, CT 4 Beds \| 5 Baths \| 3779 Sq. Ft.	$1,532,049

Address	Redfin Estimate
373 Boston Post Rd, Madison, CT 4 Beds \| 4.5 Baths \| 4892 Sq. Ft.	$2,447,042
401 Boston Post Rd, Madison, CT 4 Beds \| 2.5 Baths \| 2715 Sq. Ft.	$1,043,903

Address	Redfin Estimate
371 Boston Post Rd, Madison, CT 3 Beds \| 3.5 Baths \| 3091 Sq. Ft.	$1,238,193
391 Boston Post Rd, Madison, CT 9 Beds \| - Baths \| 8894 Sq. Ft.	$2,385,120

Property information provided by Smart MLS when last listed in 2022. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 06443, CT

Sale history for 383 Boston Post Rd

Tax history for 383 Boston Post Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06443

Home values near 383 Boston Post Rd

More real estate resources