23 Highland Terrace
Madison, Connecticut 06443
- Beds
- 3
- Baths
- 2
- SqFt
- 2,270
- Acres
- 0.28
- Year Built
- 1950
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Welcome to this special property being offered in Highland Terrace Association, a sought after enclave of Madison, Connecticut. With expansive views of Long Island Sound, this 3-story contemporary styled home sits on a large double lot with a possibility for a pool. The fact that this home has been in the same family since 1977, is a testament to its enduring appeal and desirability of this area. The open entertaining floor plan, including a wet bar area and buffet, is perfect for hosting guests, and there is plenty of parking available for them when they arrive! After spending the day at your private beach, rinse off in the outdoor shower, and enjoy the evening ocean breeze on the second floor private covered deck.The master suite features a sitting room, loft and views of the ocean. In addition to the 3 existing bedrooms, there are more options to privately or semi-privately sleep extra guests, which seems to happen at a beach house! This home requires no flood insurance and is one of the few properties with a basement. Adding to the value are a newer roof, generator, and updated electrical. Additionally, Madison features fine dining and upscale shopping. The location is convenient, being only 2 hours to NY, just over an hour to Providence, and 2 hours to Boston. Overall, this property is an idyllic place to live year round or spend the summer enjoying the private beach. Too many desirable attractions to list on the shoreline.
Key Facts
- City/Town
- Madison
- Property / Style
- Single Family · Contemporary
- Year Built
- 1950
- Days on Market
- 1196 days
- Beds
- 3
- Baths
- 2 full
- Living Area
- 2,270 sq ft
- Lot Size
- 0.28 acres
- Property Taxes
- Not on file from MLS
- HOA Fee
- $400 / Annually
Market Snapshot
The Madison Market
Single Family · trailing 12 months
Active Listings
29
47 under contract
Median List Price
$1.30M
29 active listings
Median Closed Price
$729,000
223 sales
Median Days on Market
57
29 active listings
Median $ / Sq Ft
$434
29 active listings
Sale-to-List Ratio
100.0%
223 sales
How this home compares
List Price
$850,000
vs $1.30M median
34.6% below median
Price / Sq Ft
$374
vs $434 median
13.8% below median
Days on Market
1196 days
vs 57 days median
1139 days longer than median
Based on 29 active and 223 closed sales (trailing 12 mo) of single family in Madison. Source: SmartMLS · As of July 28, 2026.
Location
23 Highland Terrace, Madison, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$4,334
- Property Taxes$0
- Insurance$283
- HOA$33
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Madison
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Contemporary
- Year Built
- 1950
- Living Area
- 2,270 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Daniel Hand
Interior
- Heating
- Hot Air
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry
- Lower Level
- Interior Features
- Open Floor Plan
Exterior & Lot
- Lot Size
- 0.28 acres
- Garage / Parking
- Attached GaragePaved
- Waterfront
- Direct waterfront
- Waterfront Details
- L. I. Sound FrontageBeach RightsViewWalk to Water
- Construction
- ShingleWood
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- DeckGarden AreaPorch
- Lot Description
- Open LotDryWater ViewLevel Lot
HOA / Association
- Fee
- $400 / Annually
- Amenities
- Playground/Tot LotTennis Courts
Listing & Financials
- Days on Market
- 1196
- MLS #
- 170560852
- MLS Status
- Under Contract
- Financing
- Assumable,FHA,VA,CHFA
Similar Properties
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Buyer's Agent
Pamela Stephanie D'Arc
William Pitt Sotheby's Int'l
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 6:10 AM UTC.