44 Chamberlain Hill Road
Middletown, Connecticut 06457
- Beds
- 6
- Baths
- 3 | 1
- SqFt
- 3,199
- Acres
- 7.02
- Year Built
- 1980
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
49
47 under contract
Median List Price
$437,000
49 active listings
Median Closed Price
$406,500
322 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 22, 2026per 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
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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 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.