150 Race Hill Road
Madison, Connecticut 06443
- Beds
- 4
- Baths
- 3
- SqFt
- 2,792
- Acres
- 7.07
- Year Built
- 1764
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
A rare and remarkably charming Antique in one of Madison's most picturesque settings. Set on 7+ acres along quiet Race Hill Rd, this beautifully preserved circa-1764 Cape blends centuries of character with thoughtful updates and the ease of modern living. Originally restored to the studs in 1996, the 2,091 sq.ft. main house retains an extraordinary amount of its original character, including chestnut flooring, period hardware, exposed beams and other details that give the home a wonderful sense of history. The floor plan is warm and inviting. The dining area opens to a family room with rustic beams, one of the original fireplaces and windows overlooking the private grounds. The family room, which could also work as a 1st floor bedroom, is highlighted by a 2nd original fireplace, built-ins and a full bath. The formal living room is distinguished with a 3rd fireplace, loads of windows and original cabinetry. A charming kitchen with cathedral ceilings and exposed beams, and a terrific sun room with a stone floor and private entrance complete the main living spaces. Upstairs you'll find three bedrooms and a full bath. And then there is the guest cottage! A beautifully renovated, year-round 701 sq.ft. legal one-bedroom cottage, that is an exceptional addition to the property-ideal for guests, extended family, a private office or rental use. Thoughtfully refinished and entirely independent, the cottage adds a level of flexibility rarely found.
Key Facts
- City/Town
- Madison
- Neighborhood
- N/A
- Property / Style
- Single Family · Cape Cod,Antique
- Year Built
- 1764
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 3 full
- Living Area
- 2,792 sq ft
- Lot Size
- 7.07 acres
- Property Taxes
- $10,467 / Annually
Market Snapshot
The Madison Market
Single Family · trailing 12 months
Active Listings
35
28 under contract
Median List Price
$1.20M
35 active listings
Median Closed Price
$775,000
224 sales
Median Days on Market
56
35 active listings
Median $ / Sq Ft
$388
35 active listings
Sale-to-List Ratio
100.0%
224 sales
How this home compares
List Price
$849,000
vs $1.20M median
29.2% below median
Price / Sq Ft
$304
vs $388 median
21.6% below median
Days on Market
0 days
vs 56 days median
56 days fresher than median
Based on 35 active and 224 closed sales (trailing 12 mo) of single family in Madison. Source: SmartMLS · As of September 20, 2026.
Location
150 Race Hill Road, Madison, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 17, 2026per month
- Principal & Interest$4,496
- Property Taxes$872
- Insurance$283
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Madison
- Neighborhood
- N/A
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Cape Cod,Antique
- Year Built
- 1764
- New Construction
- No/Resale
- Living Area
- 2,792 sq ft
Schools
- Elementary
- Brown Elementary
- High
- Daniel Hand
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Window Unit
- Laundry
- Main Level
- Laundry Location
- In Kitchen
- Appliances
- Oven/RangeRefrigeratorFreezerDishwasherWasherDryer
- Basement
- FullUnfinishedDirt Floor
Exterior & Lot
- Lot Size
- 7.07 acres
- Zoning
- RU-1
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Clapboard
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Guest HouseStone WallPatio
- Lot Description
- Lightly WoodedLevel Lot
Listing & Financials
- Property Taxes
- $10,467 / Annually
- Days on Market
- 0
- MLS #
- 24208079
- MLS Status
- Coming Soon
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/20/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 9/20/2026 at 4:15 PM UTC.