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44 Chamberlain Hill Road

Middletown, Connecticut 06457

PENDING$779,000
Beds
6
Baths
3 | 1
SqFt
3,199
Acres
7.02
Year Built
1980
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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1-Car Garage2 Fireplaces

About This Home

A truly extraordinary residence where distinctive architecture, exceptional privacy and sophisticated design come together to create a home unlike any other. Privately set on 3.5 acres, this beautifully renovated contemporary offers more than 5,500 square feet of impressive living space, with soaring interiors, walls of windows and an abundance of natural light creating a seamless connection to the surrounding landscape. The beautifully designed kitchen features quartz countertops, stainless steel appliances, double ovens, and generous space for gathering and entertaining. Two striking stone fireplaces serve as dramatic focal points, adding warmth, texture and character to the home's expansive living spaces. Offering six bedrooms and three-and-a-half beautifully renovated baths, the versatile floor plan provides exceptional flexibility for today's lifestyle. With its generous proportions and abundance of private and flexible spaces, the home is ideally suited for multigenerational living, extended family, guests, or those seeking dedicated space for a home office or home-based business. A fabulous loft provides yet another versatile area for a family room, office or game room. The spacious primary suite offers a walk-in closet, beautifully updated bath and private patio overlooking the peaceful surroundings. Throughout the home, meticulous details, interesting architectural elements and thoughtfully designed spaces create a sense of character rarely found in

Key Facts

City/Town
Middletown
Neighborhood
N/A
Property / Style
Single Family · Contemporary
Year Built
1980
Days on Market
63 days
Beds
6
Baths
3 full · 1 half
Living Area
3,199 sq ft
Lot Size
7.02 acres
Garage / Parking
1 garage
Property Taxes
$18,783 / Annually

Market Snapshot

The Middletown Market

Single Family · trailing 12 months

Median Days on Market

34

49 active listings

Median $ / Sq Ft

$247

49 active listings

Sale-to-List Ratio

102.4%

322 sales

How this home compares

List Price

$779,000

vs $437,000 median

78.3% above median

Price / Sq Ft

$244

vs $247 median

In line with median

Days on Market

63 days

vs 34 days median

29 days longer than median

Based on 49 active and 322 closed sales (trailing 12 mo) of single family in Middletown. Source: SmartMLS · As of October 22, 2026.

Location

44 Chamberlain Hill Road, Middletown, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$6,106

per month

  • Principal & Interest$4,281
  • Property Taxes$1,565
  • Insurance$260
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Middletown
Neighborhood
N/A
County
Middlesex

Residence

Property Type
Single Family
Style
Contemporary
Year Built
1980
New Construction
No/Resale
Living Area
3,199 sq ft

Schools

Elementary
Per Board of Ed
High
Middletown

Interior

Heating
Hot Air
Heat Fuel
Electric
Cooling
Ceiling FansCentral AirSplit System
Fireplaces
2
Laundry
Lower Level
Appliances
Oven/RangeRefrigeratorFreezerDishwasher
Basement
FullInterior AccessPartially FinishedWalk-outLiveable Space
In-Law Apartment
PossibleLower LevelFirst Floor
Interior Features
Cable - AvailableOpen Floor Plan

Exterior & Lot

Lot Size
7.02 acres
Zoning
R-60
Garage / Parking
1 garage spaceAttached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
Wood
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
BalconyDeckGuttersLightingPatio
Lot Description
Lightly WoodedDrySloping Lot

Listing & Financials

Property Taxes
$18,783 / Annually
Days on Market
63
MLS #
24199581
MLS Status
Under Contract - Continue to Show

Similar Properties

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

Listed By

Sharon Linder

(860) 460-8862

Berkshire Hathaway NE Prop.

(860) 388-3411

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 10/22/2026. 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 10/22/2026 at 6:00 PM UTC.