385 Boston Post Rd
Madison, CT 06443
Madison Center
5 Beds
4.5 Baths
4,919 sqft (on 1.64 acres)
$2,247,700
as of Jun 4, 2026
$2,247,700
as of Jun 4, 2026
5 Beds
4.5 Baths
4,919 sqft
(on 1.64 acres)
Local Information
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Description
Stunning One of a kind, Mediterranean style home located in the desirable and private neighborhood of Leatherman's Hill, conveniently close to Madison town, beaches and train. The property is situated on a cul de sac, with park like grounds and custom designed outside lighting, giving it a serene estate like feeling. The home features luxurious finishes and many architectural details, including coffered ceilings, built- in book shelves, family/media room, high ceilings and sun filled rooms, all leading to the secluded outside oasis. The outdoor sanctuary includes an in ground Gunite pool with a waterfall and hot tub, along with a garden area to use for entertaining or as your own retreat. The home offers an open floor plan with spacious rooms, exquisite detailing and numerous banks of windows, a light filled center hall that has 12 ft ceilings and graceful curving stairway, making this an unparalleled estate. This 5 bedroom, 4.1 bath home, has a 3rd floor bonus room, which provides ample space for family and guests. The master suite has cathedral ceilings, luxurious bath and its own private balcony overlooking the grounds and pool area. There is a 4 car garage with custom designed cedar doors with chrome inlay and a unique storage area all specifically designed for the car enthusiast.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.
Home Highlights
Parking
Garage
Outdoor
Porch, Patio, Deck, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago
Home Details for 385 Boston Post Rd
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Interior Details BasementAtticNumber of Rooms: 12Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Library, Master Bath, Office, Pantry, Recreation Room, Sun RoomWet BarCeiling Fan |
Heating & Cooling Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air |
Levels, Entrance, & Accessibility Stories: 3Floors: Tile, Hardwood |
Appliances & Utilities Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher |
Fireplace & Spa FireplaceHot Tub or SpaJetted Bath Tub |
Security Security System |
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Exterior Home Features Roof: AsphaltDeckExterior: StuccoGardenLawnPatioPorchSprinkler System |
Pool Pool |
Parking & Garage GarageParking Spaces: 4Parking: Garage Attached, Garage Detached |
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Year Built Year Built: 1997Year Updated: 1997 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
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Lot Area: 1.64 acres |
Price History for 385 Boston Post Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 08/21/2020 | $1,495,000 | Sold | Smart MLS #170309280 |
| 06/30/2020 | $1,495,000 | Pending | Agent Provided |
| 06/24/2020 | $1,495,000 | Listed For Sale | Agent Provided |
| 11/30/2019 | $1,495,000 | ListingRemoved | Agent Provided |
| 09/11/2019 | $1,495,000 | PriceChange | Agent Provided |
| 06/21/2019 | $1,595,000 | PriceChange | Agent Provided |
| 08/12/2018 | $1,695,000 | Listed For Sale | Agent Provided |
| 09/21/2012 | $1,212,500 | Sold | Smart MLS #M9136875 |
| 10/13/2010 | $1,650,000 | ListingRemoved | Agent Provided |
| 06/11/2010 | $1,650,000 | Listed For Sale | Agent Provided |
| 11/09/1998 | $826,000 | Sold | N/A |
Market trends in Madison
Last updated April 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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Available listings
73 19MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $25,220 |
| Assessment | $1,124,400 |
Home facts updated by county records
Comparable Sales for 385 Boston Post Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.09 | Single-Family Home | $1,400,000 | 05/01/26 | 4 | 5 | 3,779 | |
0.17 | Single-Family Home | $2,001,250 | 01/28/26 | 4 | 3.5 | 3,400 | |
0.53 | Single-Family Home | $1,667,000 | 06/17/25 | 3 | 3 | 2,724 | |
0.38 | Single-Family Home | $1,225,000 | 06/19/25 | 4 | 3 | 2,340 | |
0.36 | Single-Family Home | $941,000 | 10/01/25 | 3 | 3 | 2,393 | |
0.82 | Single-Family Home | $1,585,000 | 08/22/25 | 4 | 4 | 6,010 | |
0.84 | Single-Family Home | $1,365,000 | 08/26/25 | 4 | 4 | 4,145 | |
0.52 | Single-Family Home | $1,453,000 | 08/29/25 | 5 | 3.5 | 2,647 | |
0.84 | Single-Family Home | $1,525,000 | 10/01/25 | 5 | 5.5 | 6,278 | |
0.53 | Single-Family Home | $1,100,000 | 12/18/25 | 4 | 2.5 | 3,031 |
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Assigned Schools
These are the assigned schools for 385 Boston Post Rd.
- J. Milton Jeffrey Elementary School
- K-3
- Public
- 362 Students
10/10GreatSchools RatingParent Rating AverageExcellent. Jeffrey school IS the place to be!Parent Review8y ago - Daniel Hand High School
- 9-12
- Public
- 828 Students
10/10GreatSchools RatingParent Rating AverageI feel very unsafe when in the presence of many school administrators. I wouldn’t wish the experience I’ve had here on my worst enemy. I feel constantly harassed by some teachers but more namely the school administrators, including the Vice principal. Every day I try to come in with a positive attitude about this place, but someone has to ruin it. There are however some teachers that do a great job teaching and making everyone feel safe, but the negatives outweigh this way too much.Student Review1y ago - Dr. Robert H. Brown Middle School
- 4-5
- Public
- 354 Students
9/10GreatSchools RatingParent Rating AverageThe school is great. The teachers help you as much as they can and they want you to have as much fun as possible. At the end of every trimester some related arts classes let parents come to the school to watch there kid (in Xylorythems, Theater arts, Music and Art.) There is some bullying but you can quicky report if someone is bullying you and they will quickly handle it.Student Review2y ago - Walter C. Polson Upper Middle School
- 6-8
- Public
- 520 Students
9/10GreatSchools RatingParent Rating AverageMy kids are currently attending Polson MS and are receiving an excellent education that is preparing them for high school and beyond. The course work is challenging and homework is not lacking, however, the teachers are readily available to the students for extra help before and after school. But even with all the hard work the school has great spirit and the kids have fun either in sports, theater, music or what ever their area of interest is. The schools drew us to Madison and the location has kept us! GREAT TOWN! I believe the parent involvement in the school system is a primary driver for why the school system is so successful.Parent Review14y ago 
Check out schools near 385 Boston Post Rd.
Neighborhood Overview
Neighborhood stats provided by third party data sources.
What Locals Say about Madison Center
At least 1 Trulia users voted on each feature.
100 % Say it's walkable to grocery stores
100 % Say it's walkable to restaurants
100 % Say it's dog friendly
100 % Say there's wildlife
100 % Say neighbors are friendly
50 % Say there are community events
50 % Say streets are well-lit
Sourced by Trulia users. Learn more about our methodology.
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Off Market Homes Near 385 Boston Post Rd
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385 Boston Post Rd, Madison, CT 06443 is a 5 bedroom, 5 bathroom, 4,919 sqft single-family home built in 1997. 385 Boston Post Rd is located in Madison Center, Madison. This property is not currently available for sale. 385 Boston Post Rd was last sold on Aug 21, 2020 for $1,495,000. The current Trulia Estimate for 385 Boston Post Rd is $2,247,700.