Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$2,675,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 4,766 Sq. Ft.
  • 2 Car Garage
  • Updated 25 minutes ago
See This Home
Save This Home
See This Home
Save This Home
Set back and sited high on a hill overlooking 1.6 aces of estate-like grounds with seasonal views of Long Island Sound and Madison Country Club's 18-hole golf course, this residence was constructed by one of the town's most esteemed builders as his own home, and it shows in every detail. Nine-foot ceilings and abundant light define the first floor, which includes a living/dining room and elegant den, each with a woodburning fireplace, an office (currently a playroom), and a powder room. The living room opens to large veranda ideal for outdoor living and Fourth of July parties overlooking Madison's annual fireworks display. A spectacular top of the line kitchen has double ovens, A Sub-Zero refrigerator, counter and table seating, as well as an inviting sitting area. Upstairs, the vaulted primary suite offers a sitting area with yet another fireplace, two enormous walk-in closets sure to please, and a fabulous bathroom with double vanity, walk-in shower, and soaking tub. A bedroom with ensuite bath, a laundry room, and two other bedrooms that share a family bath complete the second floor. The finished lower level adds plenty of additional living space, a full bath, and a multi-purpose bonus room. A two-story carriage style garage has space for an office/studio above. Just minutes from Madison's center and the Surf Club, this is a very special, move-in ready property. Be prepared to act quickly!

Full Property Details for 373 Boston Post Rd

General

  • Price: $2,675,000
  • Taxes: (July 2026-June 2027)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24207210
  • Updated: Today (9/25/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 10
  • Rooms/Areas: Laundry Room
  • Interior Features: Auto Garage Door Opener, Cable - Available
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Appliances: Gas Range, Wall Oven, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4
  • Primary Suite: 2 Story Window(s), Balcony/Deck, Fireplace, Full Bath, 25 x 21, Upper
  • Bedroom 1: Bedroom - Hardwood Floor, 15 x 11, Upper
  • Bedroom 2: Bedroom - Built-Ins, Hardwood Floor, 15 x 15, Upper
  • Bedroom 3: Bedroom - Full Bath, Hardwood Floor, 24 x 13, Upper

Other Rooms

  • Living Room: Living Room - 9 ft+ Ceilings, Fireplace, French Doors, Hardwood Floor, 22 x 17, Main
  • Family Room: Family Room - 9 ft+ Ceilings, Fireplace, French Doors, Hardwood Floor, 15 x 15, Main
  • Eat In Kitchen: Eat-In Kitchen - Built-Ins, Dining Area, Island, Pantry, Hardwood Floor, 25 x 18, Main
  • Dining Room: Dining Room - 9 ft+ Ceilings, French Doors, Hardwood Floor, 17 x 11, Main
  • Office: Office - 9 ft+ Ceilings, Built-Ins, Hardwood Floor, 15 x 10, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - Wall/Wall Carpet, 23 x 24, Lower
  • Rec Room: Wall/Wall Carpet, 23 x 24, Lower
  • Laundry: Upper Level

Exterior

  • Exterior Features: Balcony, Underground Utilities, Porch, Stone Wall, French Doors, Underground Sprinkler

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 4
  • Parking: Detached Garage, Driveway

Location

  • County: New Haven
  • Driving Directions: Boston Post Road (Route 1) to #373, sits atop the hill

School Information

  • Elementary School: Per Board of Ed
  • Middle School: Per Board of Ed
  • Intermediate School: Per Board of Ed
  • High School: Per Board of Ed

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hydro Air, Zoned, Natural Gas
  • Heating Fuel: Natural Gas
  • Water Heater: Electric, Tankless Hotwater

Utilities

  • Sewer: Septic
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Wood
  • Basement Desc.: Full, Storage, Partially Finished, Liveable Space, Full With Hatchway
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 4,766
  • Above Ground: 4,142 Sq. Ft.
  • Below Ground: 624 Sq. Ft.
  • Year Built: 1997

Lot Features

  • Lot Size (Acres): 1.59
  • Driveway/Sidewalk: Private, Asphalt
  • Zoning: R1
  • Lot Description: Sloping Lot, Professionally Landscaped

Water Features

  • Water Front Desc.: View

Green Features

  • Energy Features: Generator

Financial Considerations

  • Assessment Amount: $1,344,600
  • Tax Year: July 2026-June 2027

Disclosures and Reports

  • Property ID: 1155668

Listed by William Pitt Sotheby's Int'l, The Margaret Muir Team, Margaret Muir

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 373 Boston Post Rd —

  • Margaret Muir

    William Pitt Sotheby's Int'l

Agent Contact: (203) 415-9187 Office Contact: (203) 245-6700

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 373 Boston Post Rd

School District:Madison School District
NameGradesDistance
J. Milton Jeffrey Elementary School
331 Copse Road, Madison, CT 06443
K-31.1 mi
Dr. Robert H. Brown Middle School
980 Durham Road, Madison, CT 06443
4-54.2 mi
Walter C. Polson Upper Middle School
302 Green Hill Road, Madison, CT 06443
6-81.1 mi
Daniel Hand High School
286 Green Hill Road, Madison, CT 06443
9-120.9 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 373 Boston Post Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/25/2026
Listed
$2,675,000
1683.33%
MLS
11/01/1995
Sold
$150,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 373 Boston Post Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$30,159
2%
$1,344,600
—
2023
$29,581
54%
$1,344,600
110%
2023
$19,214
2%
$641,100
—
2022
$18,855
5%
$641,100
3%
2021
$18,014
2%
$624,400
—
2020
$17,702
—
$624,400
—
2019
$17,702
9%
$624,400
7%
2018
$16,314
3%
$581,800
—
2017
$15,883
3%
$581,800
—
2016
$15,412
3%
$581,800
—
2015
$14,987
2%
$581,800
—
2014
$14,644
-12%
$581,800
-29%
2013
$16,595
—
$813,900
—
2010
$16,595
—
$813,900
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 373 Boston Post Rd

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by William Pitt Sotheby's Int'l, The Margaret Muir Team, Margaret Muir

Similar Properties near 373 Boston Post Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

24 Indigo Trail, Madison, CT 06443 - Photo 1 Price Reduced
-$100,000 (-3.77%)
$2,550,000
Open House

24 Indigo Trail  Madison, CT 06443

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 5
    Total Baths
  • 6,194
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l
17 Barberry Ln, Madison, CT 06443 - Photo 1 Price Reduced
-$300,000 (-10%)
$2,700,000
Open House

17 Barberry Ln  Madison, CT 06443

  • Single Family
  • Active
  • Updated 2 days ago
  • 4
    Beds
  • 6
    Total Baths
  • 4,833
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l
76 Sachem Head Rd, Guilford, CT 06437 - Photo 1
$2,650,000

76 Sachem Head Rd  Guilford, CT 06437

  • Single Family
  • Active
  • Updated 2 days ago
  • 4
    Beds
  • 5
    Total Baths
  • 5,620
    Sq. Ft.
Listed by Sunset Creek Realty, LLC
167 Shore Rd, Clinton, CT 06413 - Photo 1
$2,749,000

167 Shore Rd  Clinton, CT 06413

  • Single Family
  • Active
  • Updated 9 hours ago
  • 4
    Beds
  • 4
    Total Baths
  • 4,381
    Sq. Ft.
Listed by Houlihan Lawrence WD

Just Listed near 373 Boston Post Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

145 Beach Park Rd, Clinton, CT 06413 - Photo 1 Just Listed
$699,000

145 Beach Park Rd  Clinton, CT 06413

  • Single Family
  • Active
  • Updated 6 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,954
    Sq. Ft.
Listed by Cathy Lynch & Team (203) 627-2331
15 Happy Acres Rd, Clinton, CT 06413 - Photo 1 Just Listed
$430,000

15 Happy Acres Rd  Clinton, CT 06413

  • Single Family
  • Active
  • Updated 25 minutes ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,622
    Sq. Ft.
Listed by Preston Roth (860) 434-8600
17 Evergreen Park, Clinton, CT 06413 - Photo 1 Just Listed
$125,000
Open House

17 Evergreen Park  Clinton, CT 06413

  • Mobile Home
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,431
    Sq. Ft.
Listed by Mark Mnich (860) 681-1956
2 Silverbrook Ln, Clinton, CT 06413 - Photo 1 Just Listed
$465,000

2 Silverbrook Ln  #2  Clinton, CT 06413

  • Single Family
  • Active
  • Updated 4 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,549
    Sq. Ft.
Listed by Compass Connecticut, LLC

Price Reduced near 373 Boston Post Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

4 Pine Pl, Clinton, CT 06413 - Photo 1 Price Reduced
-$20,000 (-2.86%)
$679,900

4 Pine Pl  Clinton, CT 06413

  • Single Family
  • Active
  • Updated 6 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 1,833
    Sq. Ft.
Listed by Connecticut Real Estate Group LLC
82 Old Post Rd, Clinton, CT 06413 - Photo 1 Price Reduced
-$19,000 (-3.02%)
$610,000

82 Old Post Rd  Clinton, CT 06413

  • Single Family
  • Active
  • Updated 6 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,765
    Sq. Ft.
Listed by William Raveis Real Estate
3 Medley Ln, Clinton, CT 06413 - Photo 1 Price Reduced
-$10,000 (-1.66%)
$594,000

3 Medley Ln  Clinton, CT 06413

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,151
    Sq. Ft.
Listed by Great Estates, CT
[Address not provided], Killingworth, CT 06419 - Photo 1 Price Reduced
-$26,000 (-3.27%)
$769,000

[Address not provided]  Killingworth, CT 06419

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,547
    Sq. Ft.
Listed by Alison Perrelli (203) 641-5232

Recent Sales near 373 Boston Post Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

37 Lantern Hill Rd, Madison, CT 06443 - Photo 1 Sold
$2,700,000

37 Lantern Hill Rd  Madison, CT 06443

  • Single Family
  • Closed
  • 5
    Beds
  • 6
    Total Baths
  • 7,139
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l
Sold by Compass Connecticut, LLC
85 Garnet Park Rd, Madison, CT 06443 - Photo 1 Sold
$2,750,000

85 Garnet Park Rd  Madison, CT 06443

  • Single Family
  • Closed
  • 4
    Beds
  • 6
    Total Baths
  • 4,854
    Sq. Ft.
Listed by William Raveis Real Estate
Sold by RE/MAX on the Bay
36 Cedar Ln, Madison, CT 06443 - Photo 1 Sold
$2,310,000

36 Cedar Ln  Madison, CT 06443

  • Single Family
  • Closed
  • 4
    Beds
  • 4
    Total Baths
  • 3,926
    Sq. Ft.
Listed by William Raveis Real Estate
Sold by William Pitt Sotheby's Int'l
81A Middle Beach Rd, Madison, CT 06443 - Photo 1 Sold
$2,495,000

81A Middle Beach Rd  Madison, CT 06443

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 3,321
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l
Sold by William Pitt Sotheby's Int'l

373 Boston Post Road, Madison, CT 06443 (MLS# 24207210) is a Single Family property with 4 bedrooms, 4 full bathrooms and 1 partial bathroom. 373 Boston Post Road is currently listed for $2,675,000 and was received on September 25, 2026. Want to learn more about 373 Boston Post Road? Do you have questions about finding other Single Family real estate for sale in Madison? You can browse all Madison real estate or contact a Coldwell Banker agent to request more information.

Tour this property