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Back 109 Boston Post Rd
Off Market

109 Boston Post Rd

New Haven County CT 06443

3
3
4
2728 sq. ft.
1 ac.
Single-Family
Last sold for $935,570
John HillJohn Hill, last sold this property on 14 August 2025 after 49 days on market.

Overview

Built in 1854 for the Chittenden family, this historic Madison home sits on a beautifully landscaped, level one-acre lot and blends classic New England charm with modern upgrades. The main residence features three bedrooms on the second floor, plus a finished third-floor loft that serves as a fourth bedroom, office, or playroom. A highlight is the detached oversized garage with a connected studio suite and full bath-ideal as a guest house, gym, studio, or office. The interior has been meticulously restored, including windows, doors, and moldings, with fully updated HVAC, plumbing, and electrical systems. The formal living room includes hardwood floors, wood-burning fireplaces, and custom built-ins. The dramatic dining room boasts vaulted ceilings, exposed beams, a stone fireplace, and wide-plank floors. A sunlit kitchen features garden views on three sides, granite counters, stainless appliances, and opens to a deck overlooking the yard. A den with built-ins, family room, and full bath complete the first floor. Upstairs, the primary suite has vaulted ceilings with skylights, carpet, and a spa-style bath with sauna shower. Two additional bedrooms with hardwood floors share a tiled bath with claw-foot tub. A bonus room offers flex space. The finished third-floor loft adds even more. Just minutes from beaches, shops, dining, trails, trains, and highways-this is a rare chance to own a piece of Madison history with space to live, create, and entertain.

Features

3 bedrooms
3 bathrooms
4 carspaces
2 garage spaces
2728 sq. ft. floor area
1 ac. lot size
Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in New Haven County over the last 12 months, the estimated median property value of 109 Boston Post Rd is $637.5k.

Median value
$637.5k
Estimated value range
$205k - $1.93m
Median days on market
9
Estimated value trend
5%
increase over the last 12 months
Average days on market is based on recent, comparable sales in New Haven County. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 109 Boston Post Rd

2025
Sold
$935,570
14 Aug 2025 by John Hill, of Seabury-Hill REALTORS
2021
Sold
$750,000
28 Jun 2021 by Diane Popolizio, of William Raveis Real Estate

Happy sellers in New Haven County

87%
87% of sellers in New Haven County reported that their sale price either exceeded or met their price expectations.

New Haven County stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 3 reviews in New Haven County over the last 12 months.

Local market activity for 3 bedroom single-family properties in New Haven County

In the last 12 months, 76 three-bedroom single-family properties similar to 109 Boston Post Rd, have been sold.

This represents a 15% increase in three-bedroom single-family properties sales when compared to the previous 12 months.

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in New Haven County

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Kelly Whiteman

Kelly Whiteman is a recommended agent for New Haven County.  They have 3 local sales and collected 2 local reviews across the last 12 months.

  •   5   (8 reviews)
  •  2 Reviews in New Haven County
  •  3 Sales in New Haven County
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Rose Ciardiello

Rose Ciardiello is a recommended agent for New Haven County.  They have 12 local sales and collected 1 local review across the last 12 months.

  •   5   (10 reviews)
  •  1 Review in New Haven County
  •  12 Sales in New Haven County
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Rob McConville

Rob McConville is a recommended agent for New Haven County.  They have 6 local sales and collected 1 local review across the last 12 months.

  •   5   (3 reviews)
  •  1 Review in New Haven County
  •  6 Sales in New Haven County
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Cathy Lynch

Cathy Lynch is a recommended agent for New Haven County.  They have 31 local sales across the last 12 months.

  •  31 Sales in New Haven County
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