Welcome to 375 Boston Post Road; also known as Leatherman’s Hill Rd; possibly named after the legendary “Leatherman” who predictably traveled the same 365 mile route every 34 days; welcomed at each stop with a hot meal and a smile before he continued his journey. The private road meanders past a small pond and iconic red barn to this stately residence nestled on two acres; affording privacy rarely enjoyed so close to a town center. Situated in the heart of Madison, CT, the home is within walking distance of the Town Beach, Golf Club, Beach Club and Town Green. The environment is spectacular. Enjoy a morning cup of coffee poolside in complete privacy. Or, an evening cocktail, again by the pool while prepping the grill; or, relax a few steps away in the home’s gazebo. Step inside sliding doors, by the pool, and into the home’s generous family room adorned with a gas fireplace, beautiful hardwood floors, and embellished with numerous built-ins, and impressive crown molding; obvious throughout the residence and a symbol of opulence and attention to architectural detail. Adjacent to the Family room is the Chef’s kitchen complete with granite countertops, top of the line appliances, oversized island, and informal dining area overlooking the pool and professionally landscaped backyard. Pass through the wet bar and prepping area and into a large formal dining room enhanced by a wood burning fireplace, hardwood floors and more impressive moldings. The two story foyer boasts beautiful chevron design hardwood floors and beckons you to the second floor which embraces a master suite with full bath and three additional generous bedrooms including a second suite. Oh, and yes, the home’s lower level. Descend the stairs and be prepared to be transported to a classic Irish Pub complete with oak bar, pool table and small alcove in which to play a few hands of poker. On the other side of the stairs enjoy an evening of wine tasting, opening a few of the 180 bottles you’ve stored away for special occasions. And yes, there’s more. The home is protected by a full house generator, and offers both security and irrigation systems. The three car garage is heated and large enough for three oversized cars. 375 Boston Post Road offers the complete “self-contained environment” offering a spectacular location and an impressive, but extremely comfortable home.
Sold for $1,875,000 on 11/02/22
$1,875,000
375 Boston Post Road, Madison, CT 06443
4beds
5,007sqft
Single Family Residence
Built in 1997
2.09 Acres Lot
$2,255,300 Zestimate®
$374/sqft
$6,796 Estimated rent
What's special
Zillow last checked: 7 hours ago
Listing updated: November 02, 2022 at 12:30pm
Listed by:
John Campbell,
Compass Connecticut, LLC
Bought with:
Clint Rodenberg, RES.0784088
William Pitt Sotheby's Int'l
Source: Smart MLS,MLS#: 170504786

Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 5
- Full bathrooms: 3
- 1/2 bathrooms: 2
Primary bedroom
- Features: Fireplace, Full Bath, Hardwood Floor, Walk-In Closet(s)
- Level: Upper
- Area: 396 Square Feet
- Dimensions: 22 x 18
Bedroom
- Features: Full Bath, Wall/Wall Carpet
- Level: Upper
- Area: 144 Square Feet
- Dimensions: 12 x 12
Bedroom
- Features: Wall/Wall Carpet
- Level: Upper
- Area: 156 Square Feet
- Dimensions: 13 x 12
Bedroom
- Features: Wall/Wall Carpet
- Level: Upper
- Area: 144 Square Feet
- Dimensions: 12 x 12
Den
- Features: Wall/Wall Carpet
- Level: Main
- Area: 140 Square Feet
- Dimensions: 14 x 10
Dining room
- Features: High Ceilings, Fireplace, Hardwood Floor
- Level: Main
- Area: 285 Square Feet
- Dimensions: 19 x 15
Family room
- Features: High Ceilings, Entertainment Center, Fireplace, French Doors, Hardwood Floor
- Level: Main
- Area: 380 Square Feet
- Dimensions: 20 x 19
Kitchen
- Features: High Ceilings, Breakfast Nook, Granite Counters, Kitchen Island, Pantry
- Level: Main
- Area: 360 Square Feet
- Dimensions: 20 x 18
Living room
- Features: Hardwood Floor
- Level: Main
- Area: 285 Square Feet
- Dimensions: 19 x 15
Rec play room
- Features: Built-in Features, Dining Area, Wall/Wall Carpet, Wet Bar
- Level: Lower
- Area: 1120 Square Feet
- Dimensions: 28 x 40
Heating
- Hydro Air, Natural Gas
Cooling
- Central Air
Appliances
- Included: Oven/Range, Oven, Range Hood, Subzero, Dishwasher, Washer, Dryer, Gas Water Heater
- Laundry: Main Level, Mud Room
Features
- Sound System, Wired for Data, Entrance Foyer
- Doors: French Doors
- Windows: Thermopane Windows
- Basement: Full,Partially Finished,Heated,Cooled,Liveable Space
- Attic: Walk-up
- Number of fireplaces: 3
Interior area
- Total structure area: 5,007
- Total interior livable area: 5,007 sqft
- Finished area above ground: 3,867
- Finished area below ground: 1,140
Property
Parking
- Total spaces: 3
- Parking features: Attached, Garage Door Opener, Asphalt
- Attached garage spaces: 3
- Has uncovered spaces: Yes
Features
- Patio & porch: Patio
- Exterior features: Garden, Rain Gutters, Lighting, Stone Wall
- Has private pool: Yes
- Pool features: In Ground, Heated, Fenced
- Fencing: Partial
- Waterfront features: Walk to Water
Lot
- Size: 2.09 Acres
- Features: Cul-De-Sac, Subdivided, Dry, Wooded, Landscaped
Details
- Additional structures: Gazebo
- Parcel number: 1155671
- Zoning: R-1
- Other equipment: Generator
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Clapboard, Wood Siding
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1997
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: Underground Utilities
Green energy
- Energy efficient items: Thermostat, Windows
Community & neighborhood
Security
- Security features: Security System
Community
- Community features: Near Public Transport, Golf, Library, Playground, Public Rec Facilities
Location
- Region: Madison
Services availability

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