This home's estimate is 23% higher than the average sale price ($1.79M) of 6 comparable homes.
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- Sale & tax history
- Property details
- Neighborhood
- Climate
385 Boston Post Rd, Madison, CT 06443
About this home
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.
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Market trends in 06443, CT
Last updated July 2026
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Sale history for 385 Boston Post Rd
$304/sq ft
$304/sq ft
$304/sq ft
$324/sq ft
$345/sq ft
$246/sq ft
$295/sq ft
$335/sq ft
Tax history for 385 Boston Post Rd
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Property details
Parking
- Garage Information
- Garage & Parking: Attached Garage, Detached Garage
- Garages Number: 4
Interior
- Interior Information
- Total Rooms: 12
- Laundry Room Info: Upper Level
- Interior Features: Audio System, Auto Garage Door Opener, Cable - Available, Cable - Pre-wired, Central Vacuum, Open Floor Plan, Security System
- Entertainment System, Lighting, Security System
- Fireplaces Total: 2
- Cooling System: Central Air
- Appliances Included: Gas Cooktop, Gas Range, Wall Oven, Microwave, Refrigerator, Dishwasher, Disposal, Compactor, Washer, Dryer
- Bathroom Information
- # of Baths (Full): 4
- # of Baths (Half): 1
- Bedroom Information
- Beds Total: 5
- Room Information
- Rooms Additional: Bonus Room, Foyer, Mud Room, Sitting Room
- Room Count: 13
- Basement Description: Crawl Space, None
- Has Attic
- Attic Description: Finished, Floored, Storage Space
Exterior
- Exterior Features
- Roof Information: Asphalt Shingle
- Exterior Siding: Stucco
- Exterior Features: Balcony, Deck, French Doors, Garden Area, Grill, Hot Tub, Lighting
- Lot Information
- Lot Description: On Cul-De-Sac, In Subdivision, Lightly Wooded, Fence - Full, Professionally Landscaped
- Pool Information
- Swimming Pool
- Pool Description: In Ground Pool, Heated, Safety Fence, Gunite
- Building Information
- Foundation Type: Concrete
- Construction Description: Masonry, Stucco
- Property Information
- Waterfront Description: Pond
- Property Type: Single Family For Sale
- Living Area SQFT Per Public Record: 4919
- Driveway Type: Private, Paved
Financial
- Assessments Information
- Assessed Value: $677,500
Utilities
- Utility Information
- Water Source: Public Water Connected
- Sewage System: Septic
- Hot Water Description: Natural Gas
- Heat Type: Gas on Gas, Hydro Air
- Heat Fuel Type: Natural Gas
Location
- HOA Information
- HOA Fee Frequency: Annually
- Association Fee Includes: Grounds Maintenance, Snow Removal, Road Maintenance
- School Information
- Middle Jr High School: Brown
- 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, Health Club, Medical Facilities, Private School(s), Shopping/Mall, Tennis Courts
- Directions: Route one to Leatherman's Hill to home on the right side next to pond
- County: New Haven
Public facts
- Beds: 5
- Baths: 5.0
- Sq. Ft.: 4,919
- Stories: 2.0
- Lot Size: 1.64 acres
- Style: Single Family Residential
- Year Built: 1997
- Year Renovated: —
- County: New Haven County
- APN: 1155674
Other
- Documents & Disclosures
- Supplement Count Public: 1
Around this home
Schools
Public K-3 • Assigned • 1.0mi
Public 6-8 • Assigned • 1.0mi
Public 9-12 • Assigned • 0.9mi
Lifestyle
Provided by Walk Score and Local Logic
Climate risks
Minimal risk of a flood reaching the building in the next 30 years
Unlikely to be in a wildfire in next 30 years
7 days above 93° expected this year, 18 days in 30 years
80% chance of strong winds in next 30 years
5 unhealthy days expected this year, 8 days in 30 years
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.
Nearby similar homes
New listings for sale in 06443
Home values near 385 Boston Post Rd
| Address | Redfin Estimate |
|---|---|
4 Beds | 5 Baths | 5918 Sq. Ft. | $1,908,501 |
5 Beds | 4.5 Baths | 4031 Sq. Ft. | $1,636,059 |
| Address | Redfin Estimate |
|---|---|
4 Beds | 4.5 Baths | 4892 Sq. Ft. | $2,447,042 |
4 Beds | 5 Baths | 3779 Sq. Ft. | $1,532,049 |
| Address | Redfin Estimate |
|---|---|
3 Beds | 3.5 Baths | 3091 Sq. Ft. | $1,238,193 |
4 Beds | 2.5 Baths | 2715 Sq. Ft. | $1,043,903 |
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