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23 Highland Terrace

Madison, Connecticut 06443

PENDING$850,000
Beds
3
Baths
2
SqFt
2,270
Acres
0.28
Year Built
1950
Matt Caiola

Matt Caiola

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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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,650

per 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

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

Listed By

Teri Lewis

(860) 2277913

William Pitt Sotheby's Int'l

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.