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150 Race Hill Road

Madison, Connecticut 06443

COMING SOON - NEW$849,000
Beds
4
Baths
3
SqFt
2,792
Acres
7.07
Year Built
1764
Matt Caiola

Matt Caiola

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Guest House

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

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

Property + 11 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,651

per 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

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Phoebe Finch

(617) 645-3907

William Pitt Sotheby's Int'l

(203) 245-6700

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.